Light-emitting devices, light-emitting apparatus, electronic equipment and lighting apparatus

Abstract

To provide a light-emitting device with high luminous efficiency and low driving voltage. [Solution] Having an arylamine structure, the ordinary refraction of the deposited film to light with a wavelength of 458 nm The ratio is between 1.50 and 1.75, and the birefringence Δn of the deposited film for light with a wavelength of 458 nm is 0 or greater than or equal to 0.008 or the wavelength of the absorption peak located at the longest wavelength in the absorption spectrum Organic Provides compounds.

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, a display module, and lighting. This relates to lighting modules, display devices, light-emitting devices, electronic equipment, lighting devices, and electronic devices. Furthermore, one aspect of the present invention is not limited to the above-mentioned technical field. One aspect of the technical field relates to a product, method, or method of manufacture. Or, the present invention. One aspect of this is a process, machine, manufacture, or composition. This relates to matter. Therefore, the invention disclosed more specifically in this specification One aspect of the technical field is semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, and lighting devices. A device, an energy storage device, a memory device, an imaging device, a method for driving them, or a method for manufacturing them. This can be given as an example. [Background technology]

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting devices (organic EL devices) that utilize these (ence) is progressing. The basic configuration of a light-emitting device is an organic compound layer (EL layer) containing light-emitting material between a pair of electrodes. It is sandwiched in between. A voltage is applied to this device to inject a carrier, and the carrier By utilizing the recombination energy, light emission can be obtained from light-emitting materials.

[0003] Since such light-emitting devices are self-emissive, when used as pixels in a display, they become liquid crystals. Compared to other displays, it has advantages such as higher visibility and the elimination of the need for a backlight, and flat panel displays. It is particularly suitable for displays. Furthermore, displays using such light-emitting devices are Another major advantage is that it can be manufactured to be thin and lightweight. Furthermore, it is characterized by its extremely fast response speed. It is one of them.

[0004] Furthermore, these light-emitting devices allow for the continuous formation of a light-emitting layer in a planar manner. This allows for the emission of light in a planar manner. This is possible with incandescent bulbs and LEDs (Light-Emitting Bulbs). It is difficult to obtain with point light sources such as diodes, or line light sources such as fluorescent lamps. Because of its distinctive characteristics, it has high potential as a surface light source that can be applied to lighting and other applications.

[0005] Display and lighting devices using light-emitting devices in this manner are suitable for a variety of electronic devices. However, research and development are underway to find light-emitting devices with even better characteristics.

[0006] One of the issues often raised when discussing OLED devices is light extraction. It has low efficiency. By forming a layer made of a low refractive index material inside the EL layer, the light extraction effect can be improved. Configurations have been proposed to improve the rate and enhance the external quantum efficiency (see, for example, Patent Document 1). ). [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] U.S. Patent Application Publication No. 2020 / 0176692 [Overview of the Initiative] [Problems that the invention aims to solve]

[0008] As described above, by providing a low refractive index layer inside the organic EL device, light extraction is possible. While it is possible to improve efficiency, high carrier transportability and low refractive index are usually not compatible. They are in a red-off relationship. This is because carrier transport in organic compounds is related to unsaturated bonds. This is largely due to the presence of unsaturated bonds, and organic compounds with many unsaturated bonds have a high refractive index. Because there is a tendency.

[0009] Furthermore, in order to obtain organic compounds with a low refractive index, substituents with low molecular refraction (e.g.) are added to the molecule. For example, it is preferable to introduce saturated hydrocarbon groups or cyclic saturated hydrocarbon groups, but these substitutions are preferable. This can sometimes hinder carrier movement and reduce carrier transportability.

[0010] When an organic EL device is fabricated using a material with low carrier transport properties, the EL device The driving voltage becomes high, resulting in high power consumption. Organic EL devices are thin and light Due to its large size, it is often used in applications that require batteries for operation, and therefore has high power consumption. This is extremely important.

[0011] Therefore, in one aspect of the present invention, the refractive index is low, and even when used in an EL device, the driving power The objective is to provide an organic compound that can suppress the rise in pressure.

[0012] Alternatively, in one aspect of the present invention, a light-emitting device with high luminous efficiency and low driving voltage is fabricated. The objective is to provide an organic compound that can do so. Alternatively, in one aspect of the present invention, The objective is to provide a light-emitting device with high light efficiency and low driving voltage. In one embodiment, a light-emitting device, light-emitting apparatus, electronic device, display device with low power consumption, and The aim is to provide one of the electronic devices.

[0013] The present invention only needs to solve one of the above-mentioned problems. [Means for solving the problem]

[0014] One aspect of the present invention comprises an anode, a cathode, and an EL layer located between the anode and the cathode. The EL layer has an emissive layer and a hole transport region, and the hole transport region is connected to the anode and Located between the light-emitting layer and the hole transport region, it has an arylamine structure and a wavelength of 45 The ordinary refractive index of the deposited film for 8nm light is 1.50 or higher and 1.75 or lower, and the wavelength is 458nm. Emissions of organic compounds containing luminescent materials, where the birefringence Δn of the deposited film for m-level light is between 0 and 0.008. It is a device.

[0015] Alternatively, another aspect of the present invention comprises an anode, a cathode, and a position located between the anode and the cathode. The EL layer has an EL layer, and the EL layer has a light-emitting layer and a hole transport region, and the hole transport region is , located between the anode and the light-emitting layer, the hole transport region has an arylamine structure Furthermore, the ordinary refractive index of the deposited film for light with a wavelength of 458 nm is 1.50 or more and 1.75 or less, The orientation order of the deposited film relative to the wavelength of the absorption peak located at the longest wavelength in the absorption spectrum. This is a light-emitting device having an organic compound with a parameter between 0.07 and 0.00. .

[0016] Alternatively, in another aspect of the present invention, in the above configuration, the ally in the organic compound A group containing a parabiphenyl structure is bonded to at least one nitrogen atom of the amine in the amine structure. It is a light-emitting device.

[0017] Alternatively, another aspect of the present invention comprises an anode, a cathode, and a position located between the anode and the cathode. The EL layer has an EL layer, and the EL layer has a light-emitting layer and a hole transport region, and the hole transport region is , located between the anode and the light-emitting layer, the hole transport region has an arylamine structure Furthermore, the refractive index of the deposited film for light with a wavelength of 458 nm is 1.50 or more and 1.75 or less, and wavelength The birefringence Δn of the deposited film for light at 458 nm is between 0 and 0.04, and 1,1'-bi This is a light-emitting device containing an organic compound in which a phenyl-4-yl group is bonded to the nitrogen atom of an amine.

[0018] Alternatively, another aspect of the present invention comprises an anode, a cathode, and a position located between the anode and the cathode. The EL layer has an EL layer, and the EL layer has a light-emitting layer and a hole transport region, and the hole transport region is The hole transport region is located between the anode and the light-emitting layer and has an arylamine structure. Furthermore, the ordinary refractive index of the deposited film for light with a wavelength of 458 nm is 1.50 or more and 1.75 or less, The orientation of the deposited film with respect to light at the wavelength of the absorption peak located at the longest wavelength in the absorption spectrum. The der parameter is between -0.10 and 0.00, and 1,1'-biphenyl-4-I This is a light-emitting device containing an organic compound in which a luminescent group is bonded to the nitrogen atom of an amine.

[0019] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the 1,1'- At least one of the 2', 3', 4', or 5' positions of the biphenyl-4-yl group has 3 carbon atoms. Having at least one alkyl group with 8 carbon atoms and a cycloalkyl group with 6 to 12 carbon atoms. It is a light-emitting device.

[0020] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the 1,1'- A light-emitting device having tert-butyl groups at the 3',5' positions of a biphenyl-4-yl group. be.

[0021] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the aryl a A hydrogen atom is bonded to the meta carbon in one or more aniline structures contained in the mine structure. It is a light-emitting device.

[0022] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the aryl a In the amine structure, one or more benzene rings in the aniline structure are independently... This is a light-emitting device having substituents at the L position.

[0023] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the aryl a In the amine structure, one of the benzene rings in the aniline structure has a cyclohe in the para position. This is a light-emitting device containing xyl groups.

[0024] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the aryl a In the amine structure, one of the benzene rings in the multiple aniline structures is phenyl at the ortho position. It is a light-emitting device having a lu group.

[0025] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is a triarylamine. It is a light-emitting device having a n structure.

[0026] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is the aryl a This is a light-emitting device in which a fluorenyl group is bonded to the nitrogen atom of an amine with a mine structure.

[0027] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is a monoamine compound It is a light-emitting device.

[0028] Alternatively, in another aspect of the present invention, in the above configuration, the hole transport region is a hole injection layer and The anode has a hole transport layer, and the hole injection layer is located between the anode and the hole transport layer. The organic compound is a light-emitting device contained in the hole transport layer.

[0029] Alternatively, in another aspect of the present invention, in the above configuration, the hole transport region is a hole injection layer and The anode has a hole transport layer, and the hole injection layer is located between the anode and the hole transport layer. The light-emitting device contains the organic compound in both the hole injection layer and the hole transport layer. ru.

[0030] Alternatively, in another aspect of the present invention, in the above configuration, the hole injection layer contains the organic compound This is a light-emitting device that contains a substance that exhibits acceptability.

[0031] Alternatively, in another aspect of the present invention, in the above configuration, the substance exhibiting the acceptability is organic It is a light-emitting device made of a compound.

[0032] One aspect of the present invention relates to a vapor-deposited film having an arylamine structure and the normal behavior of a vapor-deposited film in response to light at a wavelength of 458 nm. Birefringence of a deposited film for light with a refractive index of 1.50 to 1.75 and a wavelength of 458 nm This is an organic compound whose Δn is between 0 and 0.008.

[0033] Alternatively, another aspect of the present invention relates to a material having an arylamine structure and reacting to light with a wavelength of 458 nm The ordinary refractive index of the deposited film is 1.50 or more and 1.75 or less, and the longest wavelength of the absorption spectrum is The orientation order parameter of the deposited film with respect to light at the wavelength of the absorption peak is -0.07 These are organic compounds with a value of 0.00 or less.

[0034] Alternatively, in another aspect of the present invention, in the above configuration, the amine of the arylamine structure It is an organic compound in which a group containing at least one parabiphenyl structure is bonded to a nitrogen atom.

[0035] Alternatively, another aspect of the present invention relates to a material having an arylamine structure and reacting to light with a wavelength of 458 nm The vapor-deposited film has an ordinary refractive index of 1.50 or more and 1.75 or less, and is vapor-deposited to light with a wavelength of 458 nm. The birefringence Δn of the film is 0 or greater and 0.04 or less, and the 1,1'-biphenyl-4-yl group is It is an organic compound bonded to the nitrogen atom of mine.

[0036] Alternatively, another aspect of the present invention relates to a material having an arylamine structure and reacting to light with a wavelength of 458 nm The ordinary refractive index of the deposited film is 1.50 or more and 1.75 or less, and the longest wavelength of the absorption spectrum is The orientation order parameter of the deposited film with respect to light at the wavelength of the absorption peak located is -0.10. The value is 0.00 or less, and the 1,1'-biphenyl-4-yl group is bonded to the nitrogen of the amine. It is an organic compound.

[0037] Alternatively, in another aspect of the present invention, in the above configuration, the 1,1'-biphenyl-4-i At least one of the 2', 3', 4', or 5' positions of the group is an alkyl group having 3 to 8 carbon atoms. and an organic compound having at least one cycloalkyl group having 6 to 12 carbon atoms. .

[0038] Alternatively, in another aspect of the present invention, in the above configuration, the 1,1'-biphenyl-4-i It is an organic compound having tert-butyl groups at the 3',5' positions of the butyl group.

[0039] Alternatively, in another aspect of the present invention, in the above configuration, the arylamine structure is included A hydrogen atom is bonded to the meta carbon atom of the benzene ring in one or more aniline structures. It is an organic compound.

[0040] Alternatively, in another aspect of the present invention, in the above configuration, the arylamine structure is included In one or more aniline structures, each benzene ring independently has a substituent at the para position. It is an organic compound.

[0041] Alternatively, in another aspect of the present invention, in the above configuration, the arylamine structure is included In multiple aniline structures, one of the benzene rings has a cyclohexyl group at the para position. It is an organic compound.

[0042] Alternatively, in another aspect of the present invention, in the above configuration, the arylamine structure is included In multiple aniline structures, one of the benzene rings has a phenyl group in the ortho position. It is a hybrid.

[0043] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is a triarylamine. It is an organic compound having a n structure.

[0044] Alternatively, in another aspect of the present invention, in the above configuration, a fluorenyl group is bonded to the nitrogen. It is an organic compound.

[0045] Alternatively, in another aspect of the present invention, in the above configuration, the organic compound is a monoamine compound It is an organic compound.

[0046] Alternatively, another aspect of the present invention is a hole transport layer material comprising the organic compound described in any of the above. It is a fee.

[0047] Alternatively, another aspect of the present invention is a hole injection layer material comprising the organic compound described in any of the above. It is a fee.

[0048] Alternatively, another aspect of the present invention is a light-emitting device comprising the organic compound described in any of the above. ru.

[0049] Alternatively, another aspect of the present invention is a light-emitting device as described above, and a sensor, an operating box It is an electronic device having a tongue, speaker, or microphone.

[0050] Alternatively, another aspect of the present invention is a light-emitting device as described above, and a transistor, Alternatively, it is a light-emitting device having a substrate.

[0051] Alternatively, another aspect of the present invention comprises the light-emitting device described in any of the above descriptions and a housing. It is a lighting device.

[0052] In this specification, the term "light-emitting device" includes image display devices that use light-emitting devices. Also, connectors, such as anisotropic conductive film or TCP (Tape) may be attached to the light-emitting device. Module with Carrier Package attached, print to TCP destination. A module equipped with a wiring board, or a light-emitting device, with COG (Chip On Glas Modules with ICs (integrated circuits) directly mounted using the s) method may also be included as light-emitting devices. Furthermore, lighting fixtures and the like may have light-emitting devices. [Effects of the Invention]

[0053] In one aspect of the present invention, it is possible to fabricate a light-emitting device with high luminous efficiency and low driving voltage. It is possible to provide an organic compound with high luminescence efficiency. Alternatively, in one aspect of the present invention, a high luminescence efficiency can be provided. This makes it possible to provide a light-emitting device with a low driving voltage. Alternatively, in one aspect of the present invention, Low power consumption light-emitting devices, light-emitting apparatus, electronic devices, display devices, or electronic devices We can provide either one.

[0054] Furthermore, the description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. Furthermore, other effects are... This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings Furthermore, it is possible to extract other effects from the descriptions in the claims and other documents. [Brief explanation of the drawing]

[0055] [Figure 1] Figure 1 is a graph showing the difference in driving voltage (ΔV) between a conventional light-emitting device and a light-emitting device using an organic compound with a low refractive index, with respect to the birefringence Δn of the deposited film of the organic compound. [Figure 2] Figure 2 is a graph showing the difference (ΔV) in driving voltage between a conventional light-emitting device and a light-emitting device using an organic compound with a low refractive index, with respect to the orientation order parameter S of the deposited film of the organic compound. [Figure 3] Figures 3(A), 3(B), and 3(C) are schematic diagrams of the light-emitting device. [Figure 4] Figures 4(A) and 4(B) are diagrams representing an active matrix type light-emitting device. [Figure 5] Figures 5(A) and 5(B) are diagrams representing an active matrix type light-emitting device. [Figure 6] Figure 6 is a diagram representing an active matrix type light-emitting device. [Figure 7] Figures 7(A) and 7(B) are diagrams representing passive matrix type light-emitting devices. [Figure 8]Figures 8(A) and 8(B) are diagrams representing lighting devices. [Figure 9] Figures 9(A), 9(B1), 9(B2), and 9(C) are diagrams representing electronic devices. [Figure 10] Figures 10(A), 10(B), and 10(C) are diagrams representing electronic devices. [Figure 11] Figure 11 is a diagram representing a lighting device. [Figure 12] Figure 12 is a diagram representing a lighting device. [Figure 13] Figure 13 is a diagram representing an in-vehicle display device and lighting system. [Figure 14] Figures 14(A) and 14(B) are diagrams representing electronic devices. [Figure 15] Figures 15(A), 15(B), and 15(C) are diagrams representing electronic devices. [Figure 16] Figure 16 is a graph showing the difference (ΔV) in driving voltage between light-emitting devices 1 to 7 and conventional light-emitting devices, with respect to the birefringence Δn of the deposited film of the low refractive index organic compound possessed by each light-emitting device. [Figure 17] Figure 17 is a graph showing the difference (ΔV) in driving voltage between light-emitting devices 1 to 7 and conventional light-emitting devices with respect to the orientation order parameter S of the deposited film of the low refractive index organic compound possessed by the light-emitting device. [Figure 18] Figure 18 shows the luminance-current density characteristics of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 19] Figure 19 shows the luminance-voltage characteristics of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 20] Figure 20 shows the current efficiency-luminance characteristics of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 21] Figure 21 shows the current density-voltage characteristics of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 22] Figure 22 shows the power efficiency-luminance characteristics of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 23] Figure 23 shows the external quantum efficiency-luminance characteristics of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 24] Figure 24 shows the emission spectra of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 25] Figure 25 is a graph showing the change in brightness with respect to the operating time of light-emitting devices 1-2, 2-4, 3-3, and comparative light-emitting device 10. [Figure 26] Figure 26 shows the absorption spectrum of the low-n HTM used. [Figure 27] Figure 27 shows the current density-voltage characteristics of a measurement element using mmtBuBioFBi with only holes as carriers. [Figure 28] Figure 28 shows the hole mobility of mmtBuBioFBi. [Figure 29] Figure 29 shows the luminance-current density characteristics of the light-emitting device 20 and the comparison light-emitting device 20. [Figure 30] Figure 30 shows the luminance-voltage characteristics of the light-emitting device 20 and the comparison light-emitting device 20. [Figure 31] Figure 31 shows the current efficiency-luminance characteristics of the light-emitting device 20 and the comparative light-emitting device 20. [Figure 32] Figure 32 shows the current density-voltage characteristics of the light-emitting device 20 and the comparison light-emitting device 20. [Figure 33] Figure 33 shows the blue index-luminance characteristics of the light-emitting device 20 and the comparison light-emitting device 20. [Figure 34] Figure 34 shows the emission spectra of the light-emitting device 20 and the comparison light-emitting device 20. [Figure 35]Figure 35 shows the normalized luminance-time variation characteristics of the light-emitting device 20 and the comparative light-emitting device 20. [Figure 36] Figure 36 shows the luminance-current density characteristics of light-emitting device 30, light-emitting device 31, and comparative light-emitting device 30 and comparative light-emitting device 31. [Figure 37] Figure 37 shows the luminance-voltage characteristics of light-emitting device 30, light-emitting device 31, and reference light-emitting device 30 and reference light-emitting device 31. [Figure 38] Figure 38 shows the current efficiency-luminance characteristics of light-emitting device 30, light-emitting device 31, and comparative light-emitting device 30 and comparative light-emitting device 31. [Figure 39] Figure 39 shows the current density-voltage characteristics of light-emitting device 30, light-emitting device 31, and comparison light-emitting device 30 and comparison light-emitting device 31. [Figure 40] Figure 40 shows the blue index-luminance characteristics of light-emitting device 30, light-emitting device 31, and reference light-emitting device 30 and reference light-emitting device 31. [Figure 41] Figure 41 shows the emission spectra of light-emitting device 30, light-emitting device 31, reference light-emitting device 30, and reference light-emitting device 31. [Figure 42] Figure 42 shows the normalized luminance-time variation characteristics of light-emitting device 30, light-emitting device 31, and comparative light-emitting device 30 and comparative light-emitting device 31. [Modes for carrying out the invention]

[0056] The embodiments of the present invention will be described in detail below with reference to the drawings. However, the present invention is as follows Not limited to the description, the form and details thereof may be described without departing from the spirit and scope of the present invention. Those skilled in the art will readily understand that the invention can be modified in various ways. Therefore, the present invention is as follows: This should not be interpreted as being limited to the contents described in the embodiments.

[0057] (Embodiment 1) When light is incident perpendicularly to the optical axis of a certain material, light having a vibration plane perpendicular to the optical axis is referred to as ordinary light (ordin ary ray), and light having a vibration plane parallel to the optical axis is referred to as extraordinary light (extraordinary ray). The ordinary refractive index n o and the extraordinary refractive index n e are respectively the refractive indices corresponding to the ordinary light and extraordinary light of the material to be measured. The ordinary refractive inde x n o and the extraordinary refractive index n e can each be calculated by performing anisotropy analysis. Birefringence Δn is represented by the difference between this ordinary refractive index n o and the extraordinary refractive index n e (Δn=|n o -n e | ). When anisotropy occurs in a material, the refractive index n for ordinary light o and the refractive index n for extraordinary ligh t may differ, and birefringence Δn represents this difference. e is different. This difference is expressed as birefringence Δn.

[0058] The organic compound according to one embodiment of the present invention has an arylamine structure, and for a vapor-deposited film thereof with respect to light having a wavelength of 458 nm the ordinary refractive index of the vapor-deposited film is 1.50 or more and 1.75 or less, and the birefringence Δn of the vapor-deposited film with respect to light having a wavelength of 458 nm is 0 or more and 0.008 or less.

[0059] FIG. 1 is a graph showing the relationship between the birefringence Δn of an organic compound used in a hole transport region (hole injection layer, hole transport layer) and the driving voltage of a light-emitting device.

[0060] In FIG. 1, the vertical axis represents the difference (ΔV, at 1 mA) between the driving voltage of a light-emitting device using an organic compound with a low refractive index in the hole transport region and the driving voltage of a reference light-emitting device. In the hole transport region of the reference light-emitting device, the refractive index of an organic compound commonly used in light-emitting devices is 1.8 ​Materials with a ratio of approximately 1.9 are used. Regarding the device structure, other than the organic compound in question... They are almost identical. Also, in Figure 1, the horizontal axis is used for the hole transport region of the above-mentioned light-emitting device. This is the birefringence Δn of the organic compound. Note that in Figure 1, except for the cross-shaped plots, the same applies. The plots of light-emitting devices using organic compounds are represented using the same symbols.

[0061] Light-emitting devices containing organic compounds with a low refractive index, as mentioned above, have a base with a low molecular refraction. Due to these properties, the driving power is lower than that of light-emitting devices using organic compounds that exhibit a normal refractive index. The pressure can sometimes become too high. In fact, as shown in Figure 1, many light-emitting devices are at 0.3V. In summary, the driving voltage was higher than that of the reference light-emitting device that does not use low refractive index materials. It is.

[0062] However, as shown in Figure 1, the birefringence Δn at a wavelength of 458 nm is less than 0.008. Organic EL devices using materials that consistently exhibit small values ​​use materials with a large birefringence Δn. The results showed a significantly lower driving voltage compared to the device. This suggests that the refraction of the deposited film is... The ratio is low (the ordinary refractive index of the deposited film for light with a wavelength of 458 nm is 1.50 or more and 1.75 or less). ) and the birefringence Δn of the deposited film is small (the birefringence Δn of the deposited film for light with a wavelength of 458 nm is By using organic compounds (0 to 0.008), the driving voltage is small, and the EL To fabricate a light-emitting device with high external quantum efficiency that has a layer with a low refractive index inside the main layer. It becomes possible.

[0063] Furthermore, a small birefringence Δn indicates that the optical shadow that the material casts on both ordinary and extraordinary light is small. This means there is not much difference in resonance. Therefore, Figure 2 shows a similar device structure with a smaller refractive index. The orientation order parameter S of the organic compound applied to a light-emitting device. The relationship between this and the difference in driving voltage (ΔV, at 1mA) compared to a light-emitting device using conventional materials is shown. The graph is shown. The orientation order parameter S is given by S=(k e -k o ) / (k e +2k o )(However, k o k represents the extinction coefficient for light perpendicular to the optical axis, e This is light parallel to the optical axis. It is expressed as the extinction coefficient (representing the relative to the current state) and is used as an index to represent the orientation state of a certain material. The direction order parameter S takes a value in the range of -0.5 to +1 relative to the substrate. Perfect horizontal orientation = -0.5, perfect perpendicular orientation to the substrate = +1, random orientation In this case, the result is 0.

[0064] In Figures 1 and 2, the results for light-emitting devices using the same organic compound are represented by the same symbols. As shown in Figure 2, materials with a small birefringence Δn also have a small orientation order parameter S. There was a tendency for this to occur, and a correlation with ΔV was observed. Specifically, the refractive index of the deposited film was low (wavelength 458n The ordinary refractive index of the deposited film for light m is 1.50 or more and 1.75 or less, and the absorption spectrum is Orientation order parameter of the deposited film with respect to light at the wavelength of the absorption peak located at the longest wavelength. By using an organic compound in which S has a value of -0.07 or more and 0.00 or less, the driving voltage A light-emitting device with a small size and a low refractive index layer inside the EL layer, and high external quantum efficiency. It becomes possible to create a s. This value is close to 0, and the orientation is close to random orientation. By using this material, it is possible to lower the driving voltage of the light-emitting device. It is showing.

[0065] The ordinary refractive index of the deposited film for light with a wavelength of 458 nm used in the light-emitting device is 1.5 Organic compounds with a value between 0 and 1.75 have an amine structure, which indicates that they have carrier transport properties. This is preferable because it results in a good outcome. The amine structure is an arylamine structure, Furthermore, it is more preferable because it provides better carrier transport. Also, the arylamine structure is particularly For the same reason, a triarylamine structure is even more preferable.

[0066] Furthermore, the nitrogen atom in the amine structure may have one or more groups containing a biphenyl structure bonded to it. It is preferable that the above biphenyl structure is used as a group containing the biphenyl structure. Organic compounds to which the included groups are bonded are preferred because they have good carrier transport properties. Organic compounds in which a group having a fluorene structure is bonded to a group containing a biphenyl structure are, This is preferable because it results in good carrier transportability. Furthermore, as a group containing the above biphenyl structure, para Organic compounds to which a biphenyl structure is bonded exhibit good carrier transport properties, and glass transfer This is preferable because it improves the transition temperature (Tg).

[0067] Furthermore, in the above amine structure, a 1,1'-biphenyl-4-yl group is bonded to the nitrogen atom. The compound has a birefringence Δn of the deposited film for light at a wavelength of 458 nm of 0.008 or more and 0.04 or more. For light within the following range, or the wavelength of the absorption peak located at the longest wavelength in the absorption spectrum: If the orientation order parameter S of the deposited film is between -0.10 and 0.00, the driving voltage This configuration is preferable because it allows for the creation of a small light-emitting device.

[0068] That is, an organic compound having an arylamine structure, which reacts to light with a wavelength of 458 nm The vapor-deposited film has an ordinary refractive index of 1.50 or more and 1.75 or less, and is vapor-deposited to light with a wavelength of 458 nm. The birefringence Δn of the film is 0 or greater and 0.04 or less, and the 1,1'-biphenyl-4-yl group An organic compound having, or an organic compound having an arylamine structure, with a wavelength of 4 The ordinary refractive index of the deposited film for 58nm light is 1.50 or more and 1.75 or less, and the absorption spectrum is The orientation order parameter of the deposited film with respect to light at the wavelength of the absorption peak located at the longest wavelength of the Toll The molecule S is between -0.10 and 0.00, and the molecule has a 1,1'-biphenyl-4-yl group. Organic compounds having the above characteristics are preferred. A light-emitting device using the above organic compound has an external quantum efficiency. It is possible to create a device with high performance, low drive voltage, and low power consumption.

[0069] Furthermore, the organic compound may contain either or both saturated hydrocarbon groups and cyclic saturated hydrocarbon groups. Multiple bonding is preferable to achieve a low refractive index. The cyclic saturated hydrocarbon group is preferably a group having 1 to 12 carbon atoms, and more preferably More preferably alkyl groups having 3 to 8 carbon atoms, and cycloalkyl groups having 6 to 12 carbon atoms. The most common groups are the tert-butyl group and the cyclohexyl group. However, these groups are a When the benzene ring is directly bonded to the nitrogen of the mine skeleton, it significantly increases carrier transport. To prevent this, it is preferable that the bond is not formed in such a position. That is, the aniline structure It is preferable that the above-mentioned saturated hydrocarbon group and cyclic saturated hydrocarbon group are not bonded to the meta position of the structure. It seems so.

[0070] Furthermore, the aforementioned 1,1'-biphenyl-4-yl group has a small portion at its 2',3',4',5' positions. At the very least, alkyl groups having 3 to 8 carbon atoms and cycloalkyl groups having 6 to 12 carbon atoms. It is preferable that a tert-butyl group is bonded to the 3',5' position. It is preferable to do so.

[0071] Furthermore, all carbon atoms in the saturated hydrocarbon group and cyclic saturated hydrocarbon group described above have sp3 hybrid orbitals. Although bonds are formed, the bonds are formed using sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule. The proportion of the raw material is preferably between 23% and 55%.

[0072] Also, 1 The results of measuring the organic compound in question using 1H NMR showed that the sigma concentration was less than 4 ppm. It is preferable that the integral value of Nal exceeds the integral value of signals of 4 ppm or higher. It seems so.

[0073] Furthermore, the above organic compound has a group containing at least one fluorene structure. This is preferable because it results in good carrier transportability.

[0074] Examples of organic compounds having hole transport properties as described above include those with the following general formula (G h1 1) ~(G h1 4), general formula (G h2 1)~(G h2 3) Organic compounds having a structure like that Examples can be given. Organic compounds having such a composition are available at a wavelength of 458 nm. These are organic compounds whose deposited film has an ordinary refractive index of 1.50 or more and 1.75 or less. From among them, the birefringence Δn or the longest wavelength of the absorption spectrum for light with a wavelength of 458 nm The orientation order parameter S for light of the wavelength of the absorption peak located is within the range described above. Organic compounds can be selected and used.

[0075] [ka]

[0076] The above general formula (G h1 1) In Ar 1 Ar 2 Each of them independently represents a benzene ring or This represents a substituent in which two or three benzene rings are bonded to each other. However, Ar 1 Ar 2 of One or both are carbon atoms with 1 to 12 carbon atoms, where the carbon atoms form bonds only in sp3 hybrid orbitals. Having one or more hydrogenated groups, Ar 1 and Ar 2 All of the aforementioned hydrocarbon groups bonded to The total amount of carbon contained is 8 or more, and Ar 1 and Ar 2 Connect to one of the two The total number of carbon atoms in all of the aforementioned hydrocarbon groups is 6 or more. 1 or Ar 2 When multiple linear alkyl groups having 1 or 2 carbon atoms are bonded to the hydrocarbon group, The linear alkyl groups may be bonded together to form a ring.

[0077] [ka]

[0078] The above general formula (G h1 2) In this case, m and r each independently represent 1 or 2, and m+r is It is 2 or 3. Also, t represents an integer from 0 to 4, and is preferably 0. 5 teeth It represents any hydrocarbon group having 1 to 3 carbon atoms, and when t is an integer from 2 to 4, multiple R 5 Each of them may be the same or different, and R 5 If there are multiple, adjacent ones Group (R 5 ) may be joined to each other to form a ring. Note that if m is 2, two Even if the type of substituents, number of substituents, and bond positions of the phenylene group are the same, They may be different, and if r is 2, the types of substituents on the two phenyl groups, substituents The number of bonds and the positions of the connecting hands may be the same or different.

[0079] [ka]

[0080] The above general formula (G h1 2) and (G h1 3) In this case, n and p are each independently 1 or It represents 2, and n+p is either 2 or 3. Also, s represents an integer from 0 to 4, and is 0. R is preferable. 4 represents any hydrocarbon group having 1 to 3 carbon atoms, and s is an integer from 2 to 4. If so, multiple R 4 Each of them may be the same or different, and R 4 multiple In some cases, adjacent bases (R 4 ) may be joined to each other to form a ring. If the value is 2, the types of substituents, the number of substituents, and the bond positions of the two phenylene groups. The positions may be the same or different, and when p is 2, the positions of the two phenyl groups The type of substitution group, the number of substituents, and the position of the bonds may be the same or different.

[0081] [ka]

[0082] The above general formula (G h1 2)~(G h1 In 4), R 10 ~R 14 and R 20 ~ R 24 Each of these independently represents the number of carbon atoms that form bonds using only sp3 hybrid orbitals, either hydrogen or carbon. Represents 1 to 12 hydrocarbon groups. Note that R 10 ~R 14 At least 3 of and R 20 ~R 24 Preferably, at least 3 of the atoms are hydrogen. The carbon atoms are bonded only with sp3 hybrid orbitals. Examples of hydrocarbon groups with 1 to 12 carbon atoms that make up the compound include the tert-butyl group and the cyclamate. A lohexyl group is preferred. However, R 10 ~R 14 and R 20 ~R 24 Included The total number of carbon atoms is 8 or more, and R 10 ~R 14 or R 20 ~R 24 one of the following The total number of carbon atoms contained in one of the elements must be 6 or more. 10 ~R 14 and R 20 ~R 24 In this case, adjacent groups may be bonded to each other to form a ring.

[0083] Also, the above general formula (G h1 1)~(G h1 4) In this case, u is an integer from 0 to 4, each independently. It represents a number, preferably 0. If u is an integer between 2 and 4, multiple R 3 Each is the same They can be the same or different. Also, R 1 , R 2 and R 3 Each of them independently has 1 carbon atom. Represents alkyl groups up to 4, R 1 and R 2 They may be joined to each other to form a ring.

[0084] Furthermore, one of the materials having hole transport properties is the following (G h2 1)~(G h2 3) As shown above, it has at least one aromatic group, and the aromatic group is connected to the first to third benzene rings It is preferable that the compound is an arylamine compound having at least three alkyl groups. The first to third benzene rings are bonded in this order, and the first benzene ring is amine. Assume that it is directly bonded to the nitrogen in the molecule.

[0085] Furthermore, the first benzene ring may have a substituted or unsubstituted phenyl group. It is preferable to have a substituted phenyl group. Also, the second benzene ring or the The third benzene ring may have a phenyl group substituted with an alkyl group.

[0086] Furthermore, of the first to third benzene rings, two or more benzene rings, preferably all Hydrogen is not directly bonded to the carbon atoms at positions 1 and 3 of the benzene ring, and the above-mentioned first to A third benzene ring, a phenyl group substituted with the alkyl group described above, and at least three of the above It is assumed to be bonded to either an alkyl group or the nitrogen atom of the amine mentioned above.

[0087] Furthermore, it is preferable that the above arylamine compound further has a second aromatic group. The aromatic group of 2 is an unsubstituted monocycle, or a fused ring of three or fewer rings, substituted or unsubstituted. It is preferable that the group is a substituted or unsubstituted fused ring of three or fewer rings. The fused ring is a group having a fused ring with 6 to 13 carbon atoms forming the ring. Preferably, the group has a fluorene ring. A dimethylfluorenyl group is preferred as the component.

[0088] Furthermore, it is preferable that the above arylamine compound further has a third aromatic group. Aromatic group 3 is a group having 1 to 3 substituted or unsubstituted benzene rings.

[0089] The above-mentioned at least three alkyl groups, and alkyl groups substituted on the phenyl group, have 2 or more carbon atoms. It is preferable that the alkyl group is a chain-type alkyl group having 5 carbon atoms. In particular, the alkyl group has a number of carbon atoms A branched chain alkyl group having 3 to 5 carbon atoms is preferred, and a t-butyl group is even more preferred. stomach.

[0090] [ka]

[0091] Note that the above general formula (G h2 1) In Ar 101 is a substituted or unsubstituted benzene ring, Alternatively, it represents a substituent consisting of two or three substituted or unsubstituted benzene rings bonded to each other. .

[0092] [ka]

[0093] Note that the above general formula (G h2 2) In this case, x and y each independently represent either 1 or 2, and x +y is either 2 or 3. Also, R 109 w represents an alkyl group having 1 to 4 carbon atoms, and w is 0 It represents an integer from 4 to 4. Also, R 141and R 145 each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms. When w is 2 or more, a plurality of R 109 may each be the same or different. In addition, when x is 2, the types, the number and the bonding positions of substituents on the two phenylene groups may be the same or different. In addition, when y is 2, the types of substituents and the number of substituents on the two phenyl groups each having R 141 to R 145 may be the same or different.

[0094]

Chemical Formula

[0095] Furthermore, in the above general formula (G h2 3), R 101 to R 105 each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms , a cycloalkyl group having 6 to 12 carbon atoms, and a substituted or unsubstituted phenyl group.

[0096] In addition, in the above general formulas (G h2 1) to (G h2 3), R 106 , R 107 and R 108 each independently represent an alkyl group having 1 to 4 carbon atoms, v represents an integer of 0 to 4, and when v is 2 or more, a plurality of R 108 may each be the same or different. In addition, one of R 111 to R 115 is a substituent represented by the above general formula (g1), and the remainder ​​each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted ph enyl group. Further, in the above general formula (g1), R 121 to R 12 5 , one is a substituent represented by the above general formula (g2), and the remainder are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and substituted with an alkyl group having 1 to 6 carbon atoms any one of a phenyl group. Further, in the above general formula (g2), R to R 131 to R 1 35 are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms. Provided that R to R 111 to R 1 15 , R 121 to R 125 and R 131 to R 135 , at least 3 or more of them are alky l groups having 1 to 6 carbon atoms, the number of substituted or unsubstituted phenyl groups in R 111 to R 115 is 1 or less, and the number of phenyl groups substituted with an alkyl group having 1 to 6 carbon atoms in R to R 121 to R 125 and R 131 to R 135 is 1 or less. Further, among the three combinations of R and R , R 112 and R 114 , and R 122 and R 124 , in at least two of these three combinations, at least one R 132 and R 134 is other than hydrogen.

[0097] is a group other than hydrogen.In the present specification, the expressions "substituted or unsubstituted" or "substituted or unsubstituted" when stated, in the case where the group to which these expressions are attached has a substituent, the substituent may be an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 5 to 12 carbon atoms. can be used.

[0098] As described above, the organic compound according to one embodiment of the present invention has a low refractive index, and when used in a light-emitting device , the increase in driving voltage is small. Therefore, a light-emitting device using the organic compound according to one embodiment of the present invention can be a light-emitting device having high external quantum efficiency and low driving voltage .

[0099] (Embodiment 2)

[0100] FIG. 3(A) is a diagram illustrating a light-emitting device according to one embodiment of the present invention. The light-emitting device according to one embodiment of the present invention includes a first electrode 101, a second electrode 102, and an EL layer 103, and the EL layer uses the organic compound described in Embodiment 1.

[0101] The EL layer 103 includes a light-emitting layer 113, and may include one or both of a hole injection layer 111 and a hole transport layer 112. The light-emitting layer 113 contains a light-emitting material, and the light-emitting device according to one embodiment of the present invention obtains light emission from the light-emitting material. The light-emitting layer 113 may further contain a host material and other materials. The organic compound according to one embodiment of the present invention described in Embodiment 1 may be contained in the light-emitting layer 113, the hole transport layer 112, or the hole injection layer, or may be contained in any of these layers.

[0102] Note that in addition to these layers, an electron transport layer 114 and an electron injection layer 115 are illustrated in FIG. 3(A) However, the configuration of light-emitting devices is not limited to these.

[0103] Because this organic compound has good hole transport properties, it is effective to use it in the hole transport layer 112. Furthermore, in one embodiment of the present invention, an organic compound is mixed with an acceptor substance. The resulting film can be used as a hole injection layer 111.

[0104] Furthermore, an organic compound according to one embodiment of the present invention can also be used as a host material. Furthermore, by co-depositing an electron transport material within the light-emitting layer, the electron transport material The configuration may also involve forming an excited complex with the above-mentioned hole transport material. By forming an excitation complex, effective energy transfer to the luminescent material is achieved, and high This makes it possible to provide light-emitting devices with high efficiency and a good lifespan.

[0105] The organic compound in one aspect of the present invention is an organic compound with a low refractive index, and therefore it is placed within the EL layer By using it in the part, a light-emitting device with good external quantum efficiency can be obtained. In one aspect of the present invention, when used in a light-emitting device, the organic compound is compared with other low refractive index organic compounds. Compared to the case where the drive voltage is used, it is possible to suppress the rise in the drive voltage. Therefore, the present invention One embodiment of a light-emitting device using an organic compound has high external quantum efficiency and low driving voltage. This makes it possible to use it as an optical device.

[0106] Next, we will describe the detailed structure and material examples of the light-emitting device described above. The light-emitting device of this embodiment has a pair of electrodes, a first electrode 101 and a second electrode 102, as described above. It has an EL layer 103 consisting of multiple layers in between, and any part of the EL layer 103 contains the organic compound disclosed in Embodiment 1.

[0107] The first electrode 101 is preferably formed using a metal, an alloy, a conductive compound, a mixture thereof, or the like, which has a large work function (specifically, 4.0 eV or more). Specifically, for ex ample, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium tungsten oxide (IWZO) containing tungsten oxide and zinc oxide, and the like can be given . These conductive metal oxide films are usually formed by a sputtering method, but may also be produced by applying a sol-gel method or the like. As an example of the production method, indium zinc oxide is formed by sputtering using a target obtained by adding 1 to 20 wt% of zinc oxide to indium oxide by sputtering using a target obtained by adding 1 to 20 wt% of zinc oxide to indium oxide There is a method of forming by a sputtering method. Further, for indium tungsten oxide (IWZO) containing tungsten oxide and zinc oxide indium tungsten oxide (IWZO) contains 0. 5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide with respect to indium oxide, and can also be formed by sputtering using a target containing the above components by sputtering. In addition, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Co), copper (Cu), palladium (Pd), or nitrides of metal materials (e.g., titanium titani um nitride) and the like. Graphene can also be used. Note that by using a composite material described later for a layer in contact with the first electrode 101 in the EL layer 103 that is in contact with the first electrode 101, an electrode material can be selected regardless of the work function . This makes it possible to select an electrode material regardless of the work function.

[0108] The EL layer 103 preferably has a laminated structure, but the laminated structure is not particularly limited. There is no fixed structure, and it consists of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier block layer, and an excitation layer. Various layer structures can be applied, such as a riser block layer and a charge generation layer. Then, as shown in Figure 3(A), the hole injection layer 111, hole transport layer 112, and light-emitting layer 113 In addition, a configuration having an electron transport layer 114 and an electron injection layer 115, as shown in Figure 3(B) In addition to the hole injection layer 111, hole transport layer 112, and light emission layer 113, there is also an electron transport layer 114 Two types of configurations will be described, one having an electron injection layer 115 and a charge generation layer 116. The materials that make up each layer are described below in detail.

[0109] The hole injection layer 111 is a layer containing a substance having acceptor properties. Both organic and inorganic compounds can be used as materials.

[0110] Substances that exhibit acceptor properties include those containing electron-withdrawing groups (halogen groups, cyano groups, etc.). Compounds can be used, such as 7,7,8,8-tetracyano-2,3,5,6-tetraph Luoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,1 1-Hexacyano-1,4,5,8,9,12-Hexazatriphenylene (abbreviation: HA) T-CN), 1,3,4,5,7,8-Hexafluorotetracyano-naphthoquinodyne n (abbreviation: F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8 Examples include 9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile. This is possible, especially with electron-withdrawing in condensed aromatic rings containing multiple complex atoms, such as HAT-CN. Compounds to which the group is bonded are preferably thermally stable. Also, electron-withdrawing groups (especially fluorine) Radialene derivatives having halogen groups such as ₁ groups, cyano groups, etc. [3] are electron acceptors. It is preferred because it has very high properties, specifically α,α',α''-1,2,3-cyclopropane Centriylidenes[4-cyano-2,3,5,6-tetrafluorobenzeneaceton [Trill], α,α',α''-1,2,3-cyclopropanetriylidentris[2,6 -Dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile ], α,α',α''-1,2,3-cyclopropanetriylidentris[2,3,4, Examples include [5,6-pentafluorobenzeneacetonitrile]. It has acceptor properties. In addition to the organic compounds mentioned above, other substances that can be used include molybdenum oxide and vanadium oxide. Materials such as ruthenium oxide, tungsten oxide, and manganese oxide can be used. In addition, there are phthalocyanines such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc). Cyanine-based complex compounds, 4,4'-bis[N-(4-diphenylaminophenyl)-N -phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3- Methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl Aromatic amine compounds such as )-4,4'-diamine (abbreviation: DNTPD), or poly(3 ,4-ethylenedioxythiophene) / poly(styrenesulfonic acid)(PEDOT / PS The hole injection layer 111 can also be formed by polymers such as S. A material containing a hole transport layer (or hole transport material) receives an electric field from an adjacent hole transport layer (or hole transport material) upon application of an electric field. The offspring can be pulled out.

[0111] Furthermore, the hole injection layer 111 contains the above-mentioned acceptor substance in a material having hole transport properties. Composite materials can also be used that have been modified to include acceptor properties. By using composite materials containing certain properties, the material used to form electrodes can be selected regardless of the work function. This means that, as the first electrode 101, not only materials with a large work function, but also... This allows us to use materials with small function values.

[0112] Examples of hole-transporting materials used in composite materials include aromatic amine compounds and carbazoles. Derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.) Various organic compounds can be used. The materials include 1 x 10 -6 cm 2 It is preferable that the material has a hole mobility of / Vs or higher. It seems so. Below, we will discuss materials that can be used as hole transport materials in composite materials. List the organic compounds specifically.

[0113] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl )-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated) Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenyl Examples include carbazole derivatives such as [Duaminobenzene] (abbreviation: DPA3B). Specifically, 3-[N-(9-phenylcarbazole-3-yl)-N-phenylcarbazole-3-yl] [Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole Bazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri Su[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenylanthracene-9-yl)phenyl]-9H-carbazole (abbreviation: CzP) A) 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraph Phenylbenzene and the like can be used. As aromatic hydrocarbons, for example, 2-ter t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2 -tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3 ,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl- 9,10-Bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9, 10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylant Helical (abbreviation: DPA Anth), 2-tert-butylanthracene (abbreviation: t-BuA nth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) ), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthra Sen, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7 -Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetra Methyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10, 10'-Diphenyl-9,9'-biantryl, 10,10'-bis(2-phenylphenyl Nil)-9,9'-biantril, 10,10'-bis[(2,3,4,5,6-penta Phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene Examples include perylene and 2,5,8,11-tetra(tert-butyl)perylene. In addition, pentacene, coronene, etc. can also be used. It has a vinyl skeleton. This is also good. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2, 2-Diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2, Examples include 2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA). Furthermore, an organic compound according to one embodiment of the present invention can also be used.

[0114] Also, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenyl (Abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine) [Phenylamino(N'-phenylamino)phenyl(N'-phenylamino)phenyl(methacrylamide) (abbreviated) Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( High molecular weight compounds such as phenyl(benzidine) (abbreviated as Poly-TPD) can also be used. Cut.

[0115] Examples of hole-transporting materials used in composite materials include carbazole skeletons and dibenzof It must have one of the following skeletons: a ranic skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. More preferably, having substituents including a dibenzofuran ring or a dibenzothiophene ring. Aromatic amines, aromatic monoamines having a naphthalene ring, or 9-fluorenyl group It may also be an aromatic monoamine to which the nitrogen of the amine is bonded via an arylene group. These hole-transporting materials have an N,N-bis(4-biphenyl)amino group. Using a material is preferable because it allows for the creation of light-emitting devices with a good lifespan. Examples of materials with such hole transport properties include N-(4-biphenyl)-6,N -Diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfAB) P), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d ]Furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[ b)Naphtho[1,2-d]furan-8-yl-4''-phenyltriphenylamine (abbreviated) Name: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2 -d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphen (Lu)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)) ), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-a Min (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4) -yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N- [4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-biphenyl Min (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltri Phenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4' ,4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl Nyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA) αNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl) Riphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4''- (7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03) ), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenyl Amine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-bi Naphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4 '-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviated) Name: BBAβNαNB), 4,4'-diphenyl-4''-(5;2'-binaphthyl-1 -yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenyl (Lu)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBi) AβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4 ''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-bife Niryl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenyl Min (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenyl Luamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (Abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazole -9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tris(1, 1'-Biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'- (Carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4'' -Phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl -9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl ]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis(4-biphenylyl)-9,9'-spirobio[9H-fluorene]-2-a Min (abbreviation: BBASF), N,N-bis(1,1'-biphenyl-4-yl)-9,9 '-Spirobi[9H-Fluorene]-4-amine (abbreviation: BBASF(4)), N-(1 ,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl) Lu)-9,9'-spirobio(9H-fluorene)-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibe Nzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl] -N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine n (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluorene-9) -yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenyl Nylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl Lu-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (Abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole) -3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4 ''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: P CBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole) -3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl )-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated) Name: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole- 3-yl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[ 4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9H-fluorene- 2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluore) N-2-yl)-9,9'-spirobio-9H-fluoren-4-amine, N,N-bis( 9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren(2-yl) Len-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)- 9,9'-Spirobi-9H-Fluorene-2-amine, N,N-Bis(9,9-dimethyl -9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine Examples include:

[0116] Furthermore, hole-transporting materials used in composite materials must have a hole voltage of -5.7 eV or higher and -5.4 eV or lower. It is even more preferable that the material has a relatively deep HOMO level below. Materials that have hole transport properties have relatively deep HOMO levels, which allows for hole transport. This facilitates the injection of holes into the feeding layer 112 and allows for the creation of a light-emitting device with a good lifetime. It will become easier.

[0117] Furthermore, the organic compound described in Embodiment 1 is also a material that has hole transport properties, and the composite material It can be suitably used as a hole injection layer material for the material. By using organic compounds, a layer with a low refractive index can be formed inside the EL layer 103. This can improve the external quantum efficiency of light-emitting devices.

[0118] Furthermore, alkali metal or alkaline earth metal fluorides are preferably mixed into the above composite material. Alternatively, by increasing the atomic ratio of fluorine atoms in the layer to 20% or more, the refraction of the layer The ratio can be reduced. This also allows a layer with a lower refractive index to form inside the EL layer 103. This can be achieved, and the external quantum efficiency of light-emitting devices can be improved.

[0119] By forming the hole injection layer 111, the hole injection performance is improved, and the driving voltage is reduced. A light-emitting device can be obtained. In addition, organic compounds with acceptability can be deposited. Because it is easy to process and readily forms thin films, it is a user-friendly material.

[0120] The hole transport layer 112 is formed by including a material that has hole transport properties. The materials include 1 x 10 -6 cm 2 It is preferable to have a hole mobility of / Vs or higher. The organic compound described in Embodiment 1 is a material having hole transport properties, and is a material for a hole transport layer. It can be suitably used as a material. Therefore, the hole transport layer 112 is described in Embodiment 1. It is preferable that the specified organic compound is included, and the hole transport layer 112 is described in Embodiment 1. It is more preferable that it is composed of the specified organic compound. The organic compound described in Embodiment 1 By including the compound in the hole transport layer 112, a layer with a low refractive index is formed inside the EL layer 103. This makes it possible to improve the external quantum efficiency of light-emitting devices.

[0121] When a material other than the organic compound described in Embodiment 1 is used for the hole transport layer 112, the above positive Materials with pore transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenyl [Amino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N '-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4 ,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamine [no]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene- 9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-f Phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-Fe Nyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated) Name: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carb Zole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl (Lu)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated) Name: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H- Carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethicone L-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl [Fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-fluorene-2-amine), N-phenyl-N-[4-(9-fluorene-2-amine) [phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-full Compounds having an aromatic amine skeleton, such as olen-2-amine (abbreviation: PCBASF), 1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)benzene Bazolyl biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H Compounds having a carbazole skeleton, such as -carbazole (abbreviation: PCCP), 4,4' ,4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: D BT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene -9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4 -(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds containing a thiophene skeleton, such as Ophene (abbreviation: DBTFLP-IV), 4,4' ,4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF) 3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl The furan skeleton, such as phenyl dibenzofuran (abbreviation: mmDBFFLBi-II), Examples of compounds containing this include compounds having an aromatic amine skeleton, and carba. Compounds with a zole skeleton have good reliability and high hole transport properties, and the driving voltage This is preferable as it also contributes to reduction. Furthermore, the hole channel used in the composite material of the hole injection layer 111 is also preferable. The materials listed as having transporting properties can also be suitably used as materials constituting the hole transport layer 112. It is possible.

[0122] The light-emitting layer 113 has a light-emitting substance and a host material. It is acceptable for the materials to be included simultaneously. Furthermore, it is also acceptable for it to be a laminate of two layers with different compositions.

[0123] Whether the luminescent material is a fluorescent material or a phosphorescent material, it exhibits thermally activated delayed fluorescence (T The substance may be any other luminescent substance, even if it exhibits ADF (Active Deposition Factor). One embodiment is a layer that exhibits fluorescence emission, particularly a layer that exhibits blue fluorescence emission. It can be suitably applied depending on the circumstances.

[0124] In the light-emitting layer 113, possible materials that can be used as fluorescent light-emitting materials include, for example, Examples include those listed below. Other fluorescent materials can also be used.

[0125] 5,6-Bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyri Zin (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antri [Lu)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi Su(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene- 9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) ), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-di Phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazo (Abbreviated) 4'-(10-phenyl-9-anthryl)triphenylamine ( Name: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-dife Nyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl Nyl-N-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole -3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert- Butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-( 9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAP) A) N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1 -phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine]( Abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2- Anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-to Riphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N ',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene -2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9,1 0-Diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazole-3-A Min (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl] )-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N' -Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10 -Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis( 1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl) [Nyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N, 9-Triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 545 T,N,N'-diphenylquinacridone (abbreviation: DPQd), rubren, 5,12-bi Su(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP) T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-meth Ru-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidi [-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-Tetrakis(4-methylphenyl)tetracene-5, 11-Diamine (abbreviation: p-mPhTD), 7,14-Diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]Quinolysin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitol Lu (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidine [-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6 Trahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-p Lan-4-ylidene propanedinitrile (abbreviation: BisDCJ™), N,N'-diph Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naph [1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3, 10-Bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamine [no]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2N) bf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-fe [nylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10F) Examples include rA2Nbf(IV)-02). In particular, 1,6FLPAPrn, 1,6 Pyridine compounds such as mMemFLPAPrn and 1,6BnfAPrn-03 Representative condensed aromatic diamine compounds have high hole-trapping properties and offer high luminescence efficiency and reliability. It is preferable because it is superior.

[0126] In the light-emitting layer 113, if a phosphorescent material is used as the light-emitting material, it is possible to use it. Examples of suitable materials include the following:

[0127] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazole-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphen) Iridium(III) (abbreviation: [Ir(Mpt) z)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-Triazolat] Iridium(III) (Abbreviation: [Ir(iPrptz-3 b)3)Organometallic iridium complexes having a 4H-triazole skeleton, such as Tris[ 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazo [Lat] 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]) 1H-triazole skeleton organometallic iridium complex having fac-tris[(1-2,6-diisopropyl fer [Ir(i)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(i) Prpmi)3]), Tris[3-(2,6-dimethylphenyl)-7-methylimidazo [1,2-f]Phenantridina] Iridium(III) (Abbreviation: [Ir(dmpim) Organometallic iridium complexes having an imidazole skeleton such as pt-Me)3]), bis[ 2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium (III )Tetrakis(1-pyrazolyl)borate (abbreviation: Fir6), bis[2-(4',6' -Difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolinate Abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl ] Pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir(CF3 ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate -N,C 2’ Iridium(III) acetylacetonate (abbreviation: FIracac) Organometallic iridium complex with a phenylpyridine derivative having an electron-withdrawing group as a ligand These are compounds that exhibit blue phosphorescence, from 440 nm to 520 nm. This compound has an emission peak at nm.

[0128] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)yli Dium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp) pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidina) Iridium(III) (Abbreviation: [Ir(tBuppm)2(ac (ac)), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylp Limiginato Iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato] Iridium(III) (Abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II) I) (abbreviation: [Ir(dppm)2(acac)]) has a pyrimidine skeleton iridium metal complex, (acetylacetonato)bis(3,5-dimethyl-2-phenyl Pyrazinate iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) ), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine) Sodium iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) iridium organometallic complexes having a pyrazine skeleton, such as tris(2-phenylpyridinate) -N,C 2’ Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-Fe) Nilpyridinate-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [I r(ppy)2(acac)]), bis(benzo[h]quinolinate) iridium(III Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris (benzo) [h] Quinolinato) Iridium (III) (abbreviation: [Ir(bzq)3]), Tris (2 -phenylquinolinato-N,C 2’ Iridium(III) (abbreviation: [Ir(pq)3]) ), bis(2-phenylquinolinato-N,C 2’ Iridium(III) acetylacetate Organometallic metals with a pyridine skeleton, such as Naat (abbreviation: [Ir(pq)2(acac)]). In addition to iridium complexes, tris(acetylacetonate)(monophenanthroline) terbit Rare earth metal complexes such as um(III) (abbreviation: [Tb(acac)3(Phen)]) These are examples. These are compounds that mainly exhibit green phosphorescence, ranging from 500 nm to 60 It has an emission peak at 0 nm. Note that it is an organometallic iridium complex with a pyrimidine skeleton. This is particularly preferable because it is outstanding in terms of reliability and luminous efficiency.

[0129] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimid Sodium iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis(Ir(5mdppm)2(dibm)]), [4,6-Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridi Um(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organometallic gold with a pyrimidine skeleton, such as (abbreviation: [Ir(d1npm)2(dpm)]) Iridium complex, (acetylacetonato)bis(2,3,5-triphenylpyradinate Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3) ,5-triphenylpyrazinate)(dipivaloylmethanato) iridium(III) (abbreviation) :[Ir(tppr)2(dpm)]), (acetylacetonate)bis[2,3-bis( 4-Fluorophenyl)quinoxalinato]Iridium(III) (Abbreviation: [Ir(Fdp Organometallic iridium complexes having a pyrazine skeleton such as q)2(acac)]) Tris (1-Phenylisoquinolinato-N,C 2’ ) Iridium(III) (Abbreviation: [Ir(p iq)3]), bis(1-phenylisoquinolinato-N,C 2’ Iridium (III) Pyridine bones like acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with a specific classification, there are also 2,3,7,8,12,13,17,18-O Like kutaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complex, Tris(1,3-diphenyl-1,3-propanedionato)(monophenant Lorin) Europium (III) (abbreviation: [Eu(DBM)3(Phen)]), Tris [1-(2-tenoyl)-3,3,3-trifluoroacetonate](monophenantrolyl (e) Rare earth elements such as europium(III) (abbreviation: [Eu(TTA)3(Phen)]) Examples include metal-type complexes. These are compounds that exhibit red phosphorescence, at 600 nm. It has an emission peak from 700 nm. Also, organometallic iridium with a pyrazine skeleton. The complex yields a red emission with good chromaticity.

[0130] In addition to the phosphorescent compounds described above, other known phosphorescent substances may also be selected and used. stomach.

[0131] TADF materials include fullerenes and their derivatives, acridines and their derivatives, and eosin. Derivatives can be used. Also, magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P Examples of metal-containing porphyrins include those described in d). For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), copropol Filinetetramethyl ester-tin fluoride complex (SnF2(Copro III-4M) e) Octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiopropyl Rufirin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin - Examples include platinum chloride complexes (PtCl2OEP), etc.

[0132] [ka]

[0133] Furthermore, the following structural formula shows 2-(biphenyl-4-yl)-4,6-bis(12-) Enylindoro[2,3-a]carbazole-11-yl)-1,3,5-triazine( Abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazine-2-) (Lu)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTz) n), 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl ]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPTz) n), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl Nyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl- 5,10-Dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2 ,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acrylate) Lysine-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4 -(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: D MAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9' -Anthracene]-10'-one (abbreviation: ACRSA), and other π-electron-rich heteroaromatic rings Heterocyclic compounds having one or both of the π-electron-deficient heteroaromatic rings can also be used. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, It is preferable because it has high electron transport and hole transport properties. In particular, it has a π-electron-deficient heteroaromatic ring. Among the skeletons, the pyridine skeleton and the diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyrida The din skeleton and triazine skeleton are preferred because they are stable and reliable. In particular, ben Zoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, benzo The thienopyrazine skeleton is preferred because it has high acceptability and good reliability. Furthermore, π electrons Among skeletons with excess heteroaromatic rings, the acridine skeleton, the phenoxazine skeleton, and phenoxazine are particularly noteworthy. The thiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable. Therefore, it is preferable to have at least one of the said skeletons. The benzofuran skeleton is preferred, and the dibenzothiophene skeleton is preferred as the thiophene skeleton. Also, pyrrole skeletons include indole skeletons, carbazole skeletons, and indolocal Bazole skeleton, bicarbazole skeleton, 3-(9-phenyl-9H-carbazole-3-I) The (L)-9H-carbazole skeleton is particularly preferred. Substances in which a deficiency-type heteroaromatic ring is directly bonded to a π-electron-rich heteroaromatic ring exhibit electron-donating properties and π-electron-rich properties. The electron-deficient heteroatom rings both become stronger in electron-accepting capacity, and the energy difference between the S1 and T1 levels becomes Because it becomes smaller, it is particularly preferable because thermally activated delayed fluorescence can be obtained efficiently. Instead of electron-deficient heteroaromatic rings, aromatic rings with electron-withdrawing groups such as cyano groups are used. It is also acceptable to use aromatic amine skeletons, phenazine skeletons, etc., as π-electron-rich skeletons. It is possible to do so. In addition, as π-electron-deficient skeletons, xanthene skeletons and thioxanthenesio skeletons can be used. Catalyst skeleton, oxadiazole skeleton, triazole skeleton, imidazole skeleton, anthracite Quinone skeleton, phenylborane, volanthrene and other boron-containing skeletons, benzonitrile or cyanoacrylate Aromatic rings, heteroaromatic rings, and benzophenobenzenes that have nitrile or cyano groups. Carbonyl skeletons such as phosphate, phosphine oxide skeletons, sulfone skeletons, etc. can be used. Thus, at least one of a π-electron-deficient heteroaromatic ring and a π-electron-excess heteroaromatic ring Instead, π-electron-deficient and π-electron-excess skeletons can be used.

[0134] [ka]

[0135] TADF materials are characterized by a small difference between the S1 and T1 levels, and triple intersystem crossing occurs due to reverse intersystem crossing. A function that can convert energy from singlet excitation energy to singlet excitation energy. It is a material that possesses this property. Therefore, the triplet excitation energy is obtained by a small amount of thermal energy. Upconversion to the multiplet excitation energy (reverse intersystem crossing) is possible, and the singlet excited state can be efficiently converted. It can be generated easily. Furthermore, the triplet excitation energy can be converted into luminescence. .

[0136] Furthermore, an excited complex (exciplex) is formed by two different substances forming an excited state. Exciplex (also called 'x' or 'exciplex') is a state where the difference between the S1 level and the T1 level is extremely small. As a TADF material capable of converting triplet excitation energy to singlet excitation energy, It has the function of being functional.

[0137] Furthermore, phosphorescence observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. A vector can be used. For TADF materials, the short-wavelength tail of its fluorescence spectrum is Draw a tangent line, and set the energy at the wavelength of the extrapolation line as the S1 level, and the phosphorescence spectrum When a tangent is drawn at the tail on the short wavelength side, and the energy at the wavelength of the extrapolation is taken as the T1 level, Preferably, the difference between S1 and T1 is 0.3 eV or less, and preferably 0.2 eV or less. And is even more preferable.

[0138] Furthermore, when using TADF material as a light-emitting material, the S1 level of the host material is the TADF material. It is preferable that the T1 level of the host material is higher than the S1 level of the TADF material. A higher rank is preferable.

[0139] The host material for the light-emitting layer may be an electron-transporting material, a hole-transporting material, or the above. Various carrier transport materials, such as TADF materials, can be used.

[0140] Materials with hole transport properties include those having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. A compound such as 4,4'-bis[N-(1-naphthyl)-N-phen [Nuamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N, N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl Mino-biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene -9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9- Phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-F Phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine ( Abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-cal Bazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthol (Tyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine ( Abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H -Carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethylamine Tyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl [Nyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9- Phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H- Compounds having an aromatic amine skeleton, such as ruolene]-2-amine (abbreviated as PCBASF) , 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene Luvazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl) )-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9 Compounds having a carbazole skeleton, such as H-carbazole (abbreviated as PCCP), 4,4 ',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluore] [-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds containing a thiophene skeleton, such as thiophene (abbreviation: DBTFLP-IV), 4,4 ',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DB) F3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl [nyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan skeletons Examples of compounds having the above include compounds having an aromatic amine skeleton, and Compounds with a basol skeleton are reliable, have high hole transport properties, and are suitable for driving electric currents. This is preferable because it also contributes to pressure reduction. Furthermore, the organic compounds described in Embodiment 1 can also be used. It is possible.

[0141] Examples of materials with electron transport properties include bis(10-hydroxybenzo[h]quinoli Sodium beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolate) )(4-phenylphenolate)aluminum(III) (abbreviation: BAlq), bis(8- Zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) [Phenolate]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolate zinc(II) (abbreviation: ZnBTZ), π-electron-deficient heteroatoms Organic compounds having a ring skeleton are preferred. Organic compounds having a π-electron-deficient heteroaromatic ring skeleton. For example, 2-(4-biphenylyl)-5-(4-tert-butylphenyl) -1,3,4-Oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4- Phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: T AZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadi Azole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1, 3,4-Oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviation: CO1 1) 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1 H-benzoimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene-4- [Iyl)phenyl]-1-phenyl-1H-benzoimidazole (abbreviation: mDBTBIm- II) Heterocyclic compounds having a polyazole skeleton, such as 2-[3-(dibenzothiophene -4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq- II) 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]diben Zo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H -Carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline ( Abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)pheni [Lu]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothi] Diazines such as enyl(phenyl)pyrimidine (abbreviation: 4,6mDBTP2Pm-II) Heterocyclic compounds with a skeleton, 2-[3'-(9,9-dimethyl-9H-fluorene-2- [Iyl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triyl Zin (abbreviation: mFBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-f Enyl-6-[9,9'-Spirobi(9H-Fluorene)-2-yl]-1,3,5-T Liazin (abbreviation: BP-SFTzn), 2-{3-[3-(benzo"b"naphtho[1,2 -d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-to Liazin (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo"b"naphtho[1, 2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5- Triazine (abbreviation: mBnfBPTzn-02), and other heterocycles having a triazine skeleton. Compound, 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviated) Name: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene Examples include heterocyclic compounds having a pyridine skeleton, such as (abbreviation: TmPyPB). Among them, heterocyclic compounds having a diazine skeleton, heterocyclic compounds having a triazine skeleton, Heterocyclic compounds having a pyridine skeleton are reliable and preferred. In particular, diazines ( Heterocyclic compounds with a pyrimidine or pyrazine skeleton have high electron transport properties and drive voltage It also contributes to reduction.

[0142] As for TADF materials that can be used as host materials, the previously mentioned TADF materials are... The same material can be used. When TADF material is used as the host material, TA The triplet excitation energy generated in the DF material is converted to a singlet excitation energy through reverse intersystem crossing. It is converted into a substance, and then energy is transferred to the light-emitting material, thereby increasing the luminescence efficiency of the light-emitting device. This can be achieved. At this time, the TADF material functions as an energy donor, and the luminescent substance It functions as an energy acceptor.

[0143] This is very effective when the above-mentioned light-emitting material is a fluorescent material. In order to obtain high luminescence efficiency, the S1 level of the TADF material is higher than the S1 level of the fluorescent material. It is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent material. A high level is preferable. Therefore, the T1 level of the TADF material is the same as the T1 level of the fluorescent material. A higher value is preferable.

[0144] Furthermore, T exhibits emission that overlaps with the wavelength of the lowest energy absorption band of the fluorescent material. It is preferable to use ADF material. This allows the fluorescent material to be converted from TADF material. This is preferable because it allows for smoother transfer of excitation energy and efficient emission.

[0145] Furthermore, singlet excitation energy is efficiently generated from triplet excitation energy through reverse intersystem crossing. For this to occur, it is preferable that carrier recombination occurs in the TADF material. The triplet excitation energy generated by the DF material is transferred to the triplet excitation energy of the fluorescent material. It is preferable not to do so. To that end, the fluorescent material has a luminescent phosphodiolus ( It is preferable to have a protecting group around the skeleton that causes light emission. The protecting group is a π bond. Substituents that do not have a substituent are preferred, saturated hydrocarbons are preferred, specifically those having 3 to 10 carbon atoms. The alkyl group below, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, carbon Examples include trialkylsilyl groups with a number between 3 and 10, and it is even preferable if there are multiple protecting groups. Substituents that do not have a π bond have poor carrier transport function, therefore carrier transport And with little effect on carrier recombination, the luminescent phosphodiphorus of the TADF material and the fluorescent material The distance can be increased. Here, the luminescent group is the cause of light emission in a fluorescent substance. This refers to an atomic group (skeleton) that has such a structure. The luminescent group preferably has a skeleton with π bonds and contains an aromatic ring. It is preferable that it has a condensed aromatic ring or a condensed heteroaromatic ring. As condensed heteroaromatic rings, they include the phenanthrene skeleton, stilbene skeleton, acridone skeleton, and f Examples include the enoxazine skeleton and the phenothiazine skeleton. In particular, the naphthalene skeleton and anthracite. Cene skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene n skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, naphthobisbenzofuran skeleton Fluorescent materials having this property are preferred because they have a high fluorescence quantum yield.

[0146] When using a fluorescent material as the light-emitting material, the host material should have an anthracene skeleton. Materials that are suitable for this purpose are used as host materials for fluorescent materials. When used in this way, it is possible to realize a light-emitting layer with good luminescence efficiency and durability. Host material Substances having an anthracene skeleton that can be used as a material include diphenylanthracene skeletons, In particular, substances having a 9,10-diphenylanthracene skeleton are preferred because they are chemically stable. Furthermore, if the host material has a carbazole skeleton, hole injection and transport properties are enhanced. Therefore, it is preferable, but a benzocarbazole skeleton in which a benzene ring is further condensed on carbazole is preferable. When included, the HOMO becomes about 0.1 eV shallower than that of carbazole, making it easier for holes to enter. Therefore, it is preferable. In particular, when the host material contains a dibenzocarbazole skeleton, The HOMO becomes about 0.1 eV shallower than in zole, making it easier for holes to enter, and also for hole transport. It is also excellent in terms of properties and has high heat resistance, making it suitable. Therefore, it is even more suitable as a host material. What is interesting is the 9,10-diphenylanthracene skeleton and the carbazole skeleton (or It is a substance that simultaneously possesses a benzocarbazole skeleton and a dibenzocarbazole skeleton. From the viewpoint of hole injection and transport as described above, the carbazole skeleton was replaced with a benzofluorene skeleton. A 9-fluorene or dibenzofluorene skeleton may also be used. An example of such a substance is 9-fluorene. phenyl-3-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole PCzPA (abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9 H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthraceni [Phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl] -9-Anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgD BCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-ben Zo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10 -{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}an Tracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl) Examples include phenylanthracene (abbreviation: αN-βNPAnth), and in particular, CzP A, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good characteristics, This is a favorable choice.

[0147] Furthermore, the host material may be a mixture of multiple substances, and the mixed host material When used, a mixture of electron-transporting material and hole-transporting material is used. Preferably, by mixing an electron-transporting material with a hole-transporting material. Furthermore, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. This is possible. The weight ratio of the content of hole-transporting material to electron-transporting material is positive. The ratio of materials with pore transport properties to materials with electron transport properties should be 1:19 to 19:1.

[0148] Furthermore, phosphorescent materials can be used as part of the above-mentioned mixed materials. When using a fluorescent material as a light-emitting material, excitation energy is supplied to the fluorescent material. It can be used as an energy donor.

[0149] Furthermore, these mixed materials may form excited complexes. These excited complexes are luminescent substances. It forms an excited complex that emits light that overlaps with the wavelength of the lowest energy absorption band. By selecting the right combination, energy transfer becomes smoother, and luminescence is obtained more efficiently. This is preferable because it allows for a reduction in the drive voltage.

[0150] Furthermore, at least one of the materials forming the excitation complex may be a phosphorescent material. By doing so, the triplet excitation energy is efficiently converted to the singlet excitation energy through reverse intersystem crossing. It can be converted to -.

[0151] As a combination of materials that efficiently form excited complexes, HO is a material with hole transport properties. It is preferable that the MO level is above the HOMO level of the electron-transporting material. If the LUMO level of a material with electron-transporting properties is higher than or equal to the LUMO level of a material with electron-transporting properties Preferred. Note that the LUMO and HOMO levels of the material are controlled by cyclic voltammetry. From the electrochemical properties (reduction potential and oxidation potential) of the material measured by CV (coefficient of variation) It can be derived.

[0152] Furthermore, the formation of excited complexes is related to, for example, the emission spectrum of hole-transporting materials and electron-transporting properties. The emission spectrum of a material having the above properties, and the emission spectrum of a mixed film obtained by mixing these materials. In comparison, the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each individual material. Alternatively, this can be confirmed by observing a phenomenon (which has a new peak on the longer wavelength side). Alternatively, transient photoluminescence (PL) and electron transport of materials with hole transport properties. The transient PL of materials possessing certain properties and the transient PL of a mixed film obtained by mixing these materials are compared, and the mixing The transient PL lifetime of the film has a longer lifetime component than the transient PL lifetime of each material, or a delayed lifetime component. This can be confirmed by observing differences in transient responses, such as an increase in the proportion of the time. Furthermore, the transient PL mentioned above can be interpreted as transient electroluminescence (EL). No. That is, transient EL for hole-transporting materials, transient E for electron-transporting materials. By comparing the transient EL of L and mixed films and observing the differences in transient response, Excitation complex formation can be confirmed.

[0153] The electron transport layer 114 is a layer containing a substance that has electron transport properties. As examples, the above-mentioned materials are electron-transporting substances that can be used as host materials. You can use this.

[0154] Furthermore, the electron transport layer consists of an electron-transporting material and an alkali metal or alkaline earth metal. It is preferable that it contains elements, compounds, or complexes. Also, the electron transport layer 114 has an electric field strength [ The electron mobility at which the square root of [V / cm] is 600 is 1 × 10⁻¹⁰ -7 cm 2 / Vs or more 5×1 0 -5 cm 2 It is preferable that it is less than or equal to / Vs. Electron transport properties in electron transport layer 114 By reducing the amount of electrons injected into the light-emitting layer, the amount of electrons injected into the light-emitting layer can be controlled, and the light-emitting layer can become electron-rich. This prevents the condition from occurring. This configuration, in particular, forms the hole injection layer as a composite material. Furthermore, the HOMO level of the hole-transporting material in the composite material is -5.7 eV or higher. Materials with relatively deep HOMO levels of 5.4 eV or less tend to have a good lifetime. Therefore, it is particularly preferable. In this case, the electron-transporting material has a HOMO level of -6 It is preferable that the electron transport voltage is 0.0 eV or higher. Furthermore, the material having electron transport properties is anthracene. Preferably, it is an organic compound having a skeleton, and both an anthracene skeleton and a heterocyclic skeleton are present. It is more preferable that the compound is an organic compound. The heterocyclic skeleton is a nitrogen-containing five-membered ring skeleton. Alternatively, a nitrogen-containing six-membered ring skeleton is preferred, and these heterocyclic skeletons include pyrazole rings, imida Zole ring, oxazole ring, thiazole ring, pyrazine ring, pyrimidine ring, pyridazine ring, etc. How to have a nitrogen-containing 5-membered ring skeleton or a nitrogen-containing 6-membered ring skeleton that includes two complex atoms in the ring It is particularly preferable that alkali metals or alkaline earth metals are in elemental form or compound or The complex preferably contains an 8-hydroxyquinolinate structure. Specifically, for example, For example, 8-hydroxyquinolinatolithium (abbreviation: Liq), 8-hydroxyquinolinato Examples include sodium (abbreviated as Naq). In particular, complexes of monovalent metal ions. The form, among which lithium complexes are preferred, is more preferred, and Liq is more preferred. If it contains a nolinate structure, its methyl-substituted form (e.g., 2-methyl-substituted or 5-methyl-substituted) Substitutes can also be used. In addition, alkali metals or other materials can be used in the electron transport layer. The elemental, compound, or complex of earth metal rutile has a concentration difference (0) in the thickness direction. It is preferable that the following exists (including cases where this is the case).

[0155] Between the electron transport layer 114 and the second electrode 102, an electron injection layer 115 is provided, which is lithium fluoride. LiF (LiF), Cesium Fluoride (CsF), Calcium Fluoride (CaF2), 8-Hydrogen Alkali metals or alkaline earth metals such as xikinolinatolithium (abbreviation: Liq) A layer containing the genus or compounds thereof may be provided. The electron injection layer 115 has electron transport properties. A layer made of a substance contains alkali metals, alkaline earth metals, or compounds thereof. A substance or an electride may be used. For example, a carbohydrate may be used as an electride. Examples include materials obtained by adding a high concentration of electrons to a mixed oxide of cium and aluminum.

[0156] Furthermore, the electron injection layer 115 is made of a substance having electron transport properties (preferably a bipyridine skeleton). (An organic compound containing) the above alkali metal or alkaline earth metal fluoride in a microcrystalline state It is also possible to use a layer containing a concentration of 50 wt% or more. This layer is refraction Because it is a low-efficiency layer, it is possible to provide a light-emitting device with better external quantum efficiency. It becomes Noh.

[0157] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 3(B)). The charge generation layer 116 generates holes in the layer in contact with the cathode side of the layer when an electric potential is applied, and in the anode side. This refers to a layer that can inject electrons into the adjacent layer. The charge generation layer 116 has a small amount of At the very least, a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form it using the composite materials listed as materials that can be used. Also, the P-type layer 1 17 is a composite material comprising a film containing the acceptor material described above and a hole transport material It may also be constructed by stacking films containing the P-type layer 117. By applying a potential to the P-type layer 117, electrons Electrons are injected into the transport layer 114 and holes are injected into the second electrode 102, which is the cathode, and the light-emitting device It works. Furthermore, the organic compound in one aspect of the present invention is an organic compound with a low refractive index. By using it in the P-type layer 117, it is possible to obtain a light-emitting device with good external quantum efficiency. can.

[0158] In addition to the P-type layer 117, the charge generation layer 116 also includes an electron relay layer 118 and an electron injection buffer. It is preferable that one or both of the layers 119 are provided.

[0159] The electron relay layer 118 contains at least an electron-transporting material, and the electron injection buffer layer 1 It has the function of preventing interaction between 19 and the P-type layer 117, thereby enabling smooth electron transfer. The LUMO level of the electron-transporting material contained in the relay layer 118 is in the P-type layer 117. The LUMO level of the acceptor material and the charge generation layer 116 in the electron transport layer 114 It is preferable that the LUMO level is between the LUMO level of the material contained in the contacting layer. Electron relay layer 11 Specific energy levels of the LUMO level in electron-transporting materials used in 8 The voltage should be -5.0 eV or higher, preferably -5.0 eV to -3.0 eV. As for electron-transporting materials used in the electron relay layer 118, phthalocyanine-based materials are used. It is preferable to use a material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0160] The electron injection buffer layer 119 contains alkali metals, alkaline earth metals, rare earth metals, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, and carbonates) (including carbonates such as thium and cesium carbonate), alkaline earth metal compounds (oxides, halogens) Compounds of rare earth metals (including oxides, halides, and carbonates), or compounds of rare earth metals (including oxides, halides, and carbonates) It is possible to use materials with high electron injection capabilities, such as (m)).

[0161] Furthermore, the electron injection buffer layer 119 contains an electron transporting substance and a donor substance, and If performed, alkali metals, alkaline earth metals, and rare earth metals will be used as donor substances. , and these compounds (alkali metal compounds (oxides and halides such as lithium oxide) , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, (including halides and carbonates), or compounds of rare earth metals (oxides, halides, carbon In addition to salts, tetratianaphthacene (abbreviated as TTN), nickerosene, decametine Organic compounds such as runicerosene can also be used. Therefore, it is formed using the same material as the material that constitutes the electron transport layer 114 described earlier. It is possible.

[0162] The material forming the second electrode 102 has a small work function (specifically, 3.8 eV or less). (Below) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkaline materials such as lithium (Li) and cesium (Cs). Metallic compounds, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or Group 2 of the periodic table, and alloys containing these elements (MgAg, Rare earth metals such as AlLi, europium (Eu), ytterbium (Yb), and this Examples include alloys containing these. However, between the second electrode 102 and the electron transport layer, By providing an electron injection layer, regardless of the magnitude of the work function, Al, Ag, ITO, and silica can be used. Various conductive materials such as indium oxide-tin oxide containing silicon dioxide or silicon dioxide are used as the second... It can be used as electrode 102. These conductive materials are produced using dry methods such as vacuum deposition and sputtering, as well as inkjet methods. It is possible to deposit films using methods such as spin coating. Furthermore, wet deposition can be performed using the sol-gel method. It may be formed by a mold, or by a wet process using a paste of a metallic material.

[0163] Furthermore, various methods can be used to form the EL layer 103, regardless of whether they are dry or wet methods. This can be done using methods such as vacuum deposition, gravure printing, offset printing, and screen printing. You may use methods such as printing, inkjet printing, or spin coating.

[0164] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0165] The configuration of the layer provided between the first electrode 101 and the second electrode 102 is as described above. It is not limited to the above. However, the metal used in the light-emitting region and the electrode or carrier injection layer To suppress quenching caused by proximity, the first electrode 101 and the second electrode A configuration is preferred in which a light-emitting region is provided at a location away from pole 102 where holes and electrons recombine.

[0166] Furthermore, the hole transport layer and electron transport layer in contact with the light-emitting layer 113, and especially the recombination in the light-emitting layer 113 The carrier transport layer near the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is the light-emitting material that makes up the light-emitting layer or the light contained in the light-emitting layer. It is preferable to use materials with a band gap larger than the band gap of the material itself. It seems so.

[0167] Next, we have a light-emitting device (multilayer element, tandem element) with a configuration in which multiple light-emitting units are stacked. The form of the (also called the child) will be explained with reference to Figure 3(C). This light-emitting device is This is a light-emitting device having multiple light-emitting units between the electrode and the cathode. The structure of the EL layer 103 shown in Figure 3(A) is almost the same as that of the EL layer 103 shown in Figure 3(C). The light-emitting device shown is a light-emitting device having multiple light-emitting units, as shown in Figure 3(A) or The light-emitting device shown in Figure 3(B) is a light-emitting device having one light-emitting unit. It can be said that.

[0168] In Figure 3(C), a first light-emitting unit 511 and a cathode 502 are located between the anode 501 and the cathode 502. A second light-emitting unit 512 is stacked with the first light-emitting unit 511 and the second light-emitting unit A charge generation layer 513 is provided between the knit 512 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in Figure 3(A), respectively. The same thing described in the explanation can be applied. Also, the first light-emitting unit 51 The first and second light-emitting units 512 may have the same configuration or different configurations.

[0169] When a voltage is applied to the anode 501 and cathode 502, the charge generation layer 513 generates a light from one of the light-emitting units. It has the function of injecting electrons into one unit and holes into the other light-emitting unit. That is, Figure In 3(C), when a voltage is applied such that the potential of the anode is higher than the potential of the cathode... In addition, the charge generation layer 513 injects electrons into the first light-emitting unit 511 and the second light-emitting unit Any method that injects a hole into T512 will suffice.

[0170] The charge generation layer 513 is formed with the same configuration as the charge generation layer 116 described in Figure 3(B). Preferably, composite materials of organic compounds and metal oxides have good carrier implantation and carrier transport properties. Due to its superior performance, it can achieve low-voltage and low-current operation. If the anode side of the net is in contact with the charge generation layer 513, the charge generation layer 513 will light up the unit. Since it can also serve as the hole injection layer of the net, the light-emitting unit does not require a hole injection layer. That's fine.

[0171] Furthermore, if an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since layer 119 plays the role of an electron injection layer in the anode-side light-emitting unit, the anode-side light emission The unit does not necessarily need to have an electron injection layer.

[0172] Figure 3(C) illustrates a light-emitting device having two light-emitting units, but there are also devices with three or more units. The same method can be applied to light-emitting devices that stack the above light-emitting units. As in the light-emitting device according to this embodiment, multiple light-emitting units are charged between a pair of electrodes. By separating and arranging the elements with the generation layer 513, high-brightness light emission is possible while maintaining a low current density. This enables the realization of even longer-lasting elements. Furthermore, it allows for low-voltage operation and low power consumption of light-emitting elements. The device can be realized.

[0173] Furthermore, by making the light-emitting color of each light-emitting unit different, the entire light-emitting device... This allows you to obtain light emission of the desired color. For example, a light emission device having two light emission units In the vise, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. By obtaining color, it is also possible to obtain a light-emitting device that emits white light as a whole. be.

[0174] Furthermore, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512 and Each layer, such as the charge generation layer, and the electrodes are manufactured using methods such as vapor deposition (including vacuum deposition) and droplet ejection. Formed using methods such as (also called inkjet printing), coating, or gravure printing. This can be done. Furthermore, these can be low-molecular-weight materials and medium-molecular-weight materials (including oligomers and dendrimers). or may include polymer materials.

[0175] (Embodiment 3) This embodiment describes a light-emitting device using the light-emitting device described in Embodiment 2. ru.

[0176] In this embodiment, a light-emitting device made using the light-emitting device described in Embodiment 2 is used. Let's explain using Figure 4. Figure 4(A) is a top view showing the light-emitting device, and Figure 4(B) is Figure 4(A) is a cross-sectional view taken at AB and CD. This light-emitting device is a light-emitting device The drive circuit section (source line drive circuit) 601, indicated by the dotted line, controls the emission of light. It includes a pixel section 602 and a drive circuit section (gate line drive circuit) 603. Also, 604 The sealing substrate, 605 is a sealing material, and the area inside the sealing material 605 is a space 607. It is.

[0177] The routing wire 608 is input to the source line drive circuit 601 and the gate line drive circuit 603. FPC (Flexible Printed Circuit) is a wiring system for transmitting signals and serves as an external input terminal. (Input circuit) 609 receives video signals, clock signals, start signals, reset signals, etc. Receive. Note that only the FPC is shown in the diagram here, but this FPC has a print distribution A wire substrate (PWB) may be attached. The light-emitting device in this specification is a light-emitting device This includes not only the main unit but also the state in which the FPC or PWB is attached to it. ru.

[0178] Next, the cross-sectional structure will be explained using Figure 4(B). The drive circuit section is located on the element substrate 610. And a pixel section is formed, but here, the source line drive circuit 601 which is the drive circuit section and One pixel in the pixel section 602 is shown.

[0179] The element substrate 610 is a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fiber) Made using a plastic substrate made of fluoride, polyester, or acrylic resin. Just make it.

[0180] The structure of the transistors used in the pixels and driving circuits is not particularly limited. For example, reverse transistors It may be a hoop-type transistor or a stagger-type transistor. Either a top-gate or bottom-gate transistor is acceptable. The semiconductor material used is not particularly limited; for example, silicon, germanium, silicon carbide, Gallium nitride and the like can be used. Alternatively, In-Ga-Zn metal oxides, etc. An oxide semiconductor containing at least one of indium, gallium, and zinc may also be used.

[0181] The crystallinity of semiconductor materials used in transistors is not particularly limited; amorphous semiconductors, Crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or semiconductors with a crystalline region in part) Any semiconductor having the properties of [the semiconductor material] may be used. If a semiconductor having crystalline properties is used, transients may occur. This is preferable because it suppresses the deterioration of the stanic characteristics.

[0182] Here, in addition to the transistors provided in the above-mentioned pixels and driving circuits, there is also a touch sensor, which will be described later. For semiconductor devices such as transistors used in applications like the above, oxide semiconductors are preferred. It is preferable to use oxide semiconductors, which have a wider band gap than silicon. By using oxide semiconductors with a wider bandgap than silicon, transistors can be made The current in the "F" state can be reduced.

[0183] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). It is also In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is an oxide semiconductor containing an oxide (such as a metal like La, Ce, or Hf). It is preferable.

[0184] In particular, the semiconductor layer has multiple crystalline portions, and the c-axis of the crystalline portion is the surface on which the semiconductor layer is formed. Alternatively, an acid oriented perpendicular to the upper surface of the semiconductor layer and having no grain boundaries between adjacent crystalline regions. It is preferable to use a crystalline semiconductor film.

[0185] By using such materials as semiconductor layers, fluctuations in electrical properties are suppressed, resulting in high reliability. This makes it possible to create a transistor.

[0186] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can be used to... This makes it possible to retain the charge stored in the capacity over a long period of time. By applying a generator to each pixel, the gradation of the image displayed in each display area is maintained while driving It also becomes possible to shut down the circuit. As a result, it is possible to realize electronic devices with extremely reduced power consumption. It can be expressed.

[0187] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. The undercoat may be: Inorganic silicon oxide films, silicon nitride films, silicon oxide-nitride films, silicon nitride-oxide films, etc. It can be fabricated using an insulating film, either as a single layer or in a multilayer configuration. The underlayer is fabricated by sputtering. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, ALD ( Formed using methods such as Atomic Layer Deposition, coating, and printing. Yes, it is possible. However, a base coat does not need to be applied unless necessary.

[0188] Note that FET623 is one of the transistors formed in the drive circuit section 601. Furthermore, the drive circuit is formed using various CMOS, PMOS, or NMOS circuits. This is sufficient. Furthermore, this embodiment shows a driver-integrated type in which the drive circuit is formed on the substrate. However, this is not always necessary, and the drive circuit can be formed externally rather than on the circuit board. .

[0189] Furthermore, the pixel section 602 includes a switching FET 611 and a current control FET 612 and its drive It is formed by a plurality of pixels, each including a first electrode 613 electrically connected to the rain. However, it is not limited to this, and can also be used as a pixel unit combining three or more FETs and a capacitive element. good.

[0190] Furthermore, an insulator 614 is formed covering the end of the first electrode 613. Here, positive It can be formed by using a photosensitive acrylic resin film of a mold.

[0191] Furthermore, in order to ensure good coverage of the EL layer and other layers formed later, the upper end of the insulator 614 is Alternatively, a curved surface with curvature is formed at the lower end. For example, the material of the insulator 614 and When a positive-type photosensitive acrylic resin is used, the radius of curvature is only at the upper end of the insulator 614. It is preferable to have a curved surface having a thickness of 0.2 μm to 3 μm. Also, the insulating material 614 is used. Therefore, either a negative-type or positive-type photosensitive resin can be used.

[0192] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, the material used for the first electrode 613 which functions as an anode is a material with a work function of It is desirable to use large materials. For example, ITO film or silicon-containing indigo Indium oxide film, indium oxide film containing 2-20 wt% zinc oxide, titanium nitride film, In addition to monolayer films such as chromium films, tungsten films, zinc films, and Pt films, titanium nitride films and aluminum films are also available. Lamination with a film mainly composed of aluminum, titanium nitride film and aluminum film and titanium nitride A three-layer structure with a film can be used. Furthermore, a laminated structure can be used as a wiring resistor. It has low noise levels, provides good ohmic contact, and can even function as an anode. .

[0193] Furthermore, the EL layer 616 was coated using a vapor deposition method with a vapor deposition mask, an inkjet method, and a spin coating method. It is formed by various methods such as those described in Embodiment 2. The EL layer 616 is formed by the structure described in Embodiment 2. It contains the following: In addition, other materials constituting the EL layer 616 include low molecular weight compounds, This may be a high-molecular-weight compound (including oligomers and dendrimers).

[0194] Furthermore, the material used for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. Examples include materials with a low work function (Al, Mg, Li, Ca, or alloys thereof) It is preferable to use compounds (such as MgAg, MgIn, AlLi, etc.). If the light generated at 616 passes through the second electrode 617, then the second electrode 617 is defined as follows: A thin metal film with a reduced thickness and a transparent conductive film (ITO, containing 2-20 wt% zinc oxide). Lamination with indium, silicon-containing indium tin oxide, zinc oxide (ZnO), etc. It is good to use it.

[0195] Furthermore, the first electrode 613, the EL layer 616, and the second electrode 617 form the shape of the light-emitting device. This has been achieved. The light-emitting device is the light-emitting device described in Embodiment 2. The element is made up of multiple light-emitting devices, but in the light-emitting device of this embodiment This includes both the light-emitting device described in Embodiment 2 and light-emitting devices having other configurations. It's okay if they're mixed together.

[0196] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, A light-emitting device is placed in the space 607 surrounded by the sub-substrate 610, the sealing substrate 604, and the sealing material 605. The structure is equipped with chair 618. Furthermore, the space 607 is filled with filler material. In addition to cases where inert gases (nitrogen, argon, etc.) are used for filling, there are also cases where sealing materials are used for filling. There are also cases where a recess is formed in the sealing substrate and a desiccant is placed there to prevent deterioration due to moisture. This configuration is preferable because it can suppress oxidation.

[0197] Furthermore, it is preferable to use epoxy resin and glass frit for the sealing material 605. These materials should preferably be as impermeable to moisture and oxygen as possible. In addition, as materials used for the sealing substrate 604, glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastic) are also available. Reinforced Plastics), PVF (Polyvinyl Fluoride), Poly A plastic substrate made of ester or acrylic resin can be used.

[0198] Although not shown in Figure 4, a protective film may be provided on the second electrode. The protective film is an organic resin film. It can be formed with an inorganic insulating film. Also, the exposed portion of the sealing material 605 can be covered with a protective film. A protective film may be formed. Furthermore, the protective film may be applied to the surface and sides of the pair of substrates, the sealing layer, and the insulating layer. It can be installed to cover exposed surfaces such as the margin layer.

[0199] The protective film can be made of a material that is impermeable to impurities such as water. This effectively suppresses the diffusion of impurities such as these from the outside to the inside.

[0200] Materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers can be used, for example, aluminum oxide, hafnium oxide, etc. Phenium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide Titanium dioxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide cerium oxide, scandium oxide, erbium oxide, vanadium oxide, or indi oxide Materials containing um, etc., aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, nitride Materials containing titanium, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum, Oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and Strontium-containing sulfides, erbium and aluminum-containing oxides, yttri Materials containing oxides, etc., that include um and zirconium can be used.

[0201] The protective film can be formed using a film deposition method that provides good step coverage. This is preferable. One such method is atomic layer deposition (ALD). There is a deposition method. Protecting materials that can be formed using the ALD method. It is preferable to use it in membranes. By using the ALD method, dense cracks, pinholes, etc. A protective film can be formed with reduced defects or with a uniform thickness. Also, This reduces the damage inflicted on the processed material when forming a protective film.

[0202] For example, using the ALD method, surfaces with complex uneven shapes, the top surface and sides of a touch panel can be used. A uniform protective film with few defects can be formed on both the front and back surfaces.

[0203] As described above, a light-emitting device fabricated using the light-emitting device described in Embodiment 2 is obtained. It is possible.

[0204] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2. This makes it possible to obtain a light-emitting device with good characteristics. Specifically, the method described in Embodiment 2. Because light-emitting devices have good luminous efficiency, it is possible to create light-emitting devices with low power consumption. ru.

[0205] Figure 5 shows a light-emitting device that emits white light, with a colored layer (color filter) provided. This shows an example of a light-emitting device that has been made full-color. Figure 5(A) shows substrate 1001, base Insulating film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, Interlayer insulating film 1020, second interlayer insulating film 1021, peripheral portion 1042, pixel portion 1040 , drive circuit section 1041, first electrodes 1024W, 1024R, 1024G of the light-emitting device , 1024B, partition wall 1025, EL layer 1028, second electrode 1029 of light-emitting device, seal The stopper plate 1031, sealing material 1032, etc. are shown in the diagram.

[0206] Furthermore, Figure 5(A) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on a transparent substrate 1033. Also, the black matrix 1 A 035 layer may be further provided. Transparent substrate 1 provided with a colored layer and a black matrix. 033 is aligned and fixed to substrate 1001. Note that the colored layer and black matrix Kus 1035 is covered with an overcoat layer 1036. Also, in Figure 5(A) This consists of a light-emitting layer that allows light to escape to the outside without passing through the colored layers, and a layer that allows light to escape to the outside by passing through the colored layers of each color. There is a light-emitting layer, and light that does not pass through the colored layer is white, while light that passes through the colored layer is red, green, and blue. Therefore, images can be represented using four colored pixels.

[0207] Figure 5(B) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer Example of forming layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. This was shown. Thus, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's good too.

[0208] Furthermore, in the light-emitting device described above, light is taken to the substrate 1001 side on which the FET is formed. Although a light-emitting device with a bottom-emission structure was used, the light emission was taken from the sealing substrate 1031 side. It can also be used as a light-emitting device with a projection structure (top emission type). A cross-sectional view of the light-emitting device is shown in Figure 6. In this case, the substrate 1001 is a substrate that does not transmit light. This can be done. Until the connecting electrode that connects the FET and the anode of the light-emitting device is fabricated, the bottle It is formed in the same way as a muemission-type light-emitting device. Then, the third interlayer insulating film 1037 is electrically... It is formed covering pole 1022. This insulating film may also play a planarization role. Third layer The interlayer insulating film 1037 is formed using the same material as the second interlayer insulating film, as well as other known materials. It is possible.

[0209] The first electrodes of the light-emitting device, 1024W, 1024R, 1024G, and 1024B, are located here. It is designated as the anode, but it can also be the cathode. Also, a top-emission type generator as shown in Figure 6. In the case of an optical device, it is preferable that the first electrode be a reflective electrode. Configuration of EL layer 1028 The configuration is as described in Embodiment 2 as the EL layer 103, and the white light The device structure is designed to allow light to be obtained.

[0210] In the top emission structure shown in Figure 6, the colored layer (red colored layer 1034R, green colored layer) The sealing is performed using a sealing substrate 1031 having a color layer 1034G and a blue colored layer 1034B. This can be done. The encapsulation substrate 1031 has a black matrix positioned between the pixels. 1035 may be provided. Colored layer (red colored layer 1034R, green colored layer 1034G, The blue colored layer (1034B) and the black matrix are formed by the overcoat layer (1036). It may be covered. The sealing substrate 1031 shall be a light-transmitting substrate. Furthermore, while we have shown an example of full-color display using four colors—red, green, blue, and white—this is not particularly limited. Alternatively, full-color display may be performed using four colors: red, yellow, green, and blue, or three colors: red, green, and blue.

[0211] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure has a first electrode as a reflective electrode and a second electrode as This is obtained by using semi-transparent and semi-reflective electrodes. Between the reflective electrode and the semi-transparent and semi-reflective electrode It has at least an EL layer and at least an emissive layer that forms an emissive region.

[0212] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%. It is %, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ωcm in diameter. Also, semipermeable... The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1 × 10 -2 Assume the membrane is less than Ωcm in diameter.

[0213] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transmitting / semi-reflective electrode. It is reflected and resonates.

[0214] The light-emitting device changes the thickness of the transparent conductive film, the composite material mentioned above, the carrier transport material, etc. This allows us to change the optical distance between the reflective electrode and the semitransmissive / semi-reflective electrode. Furthermore, the light of the resonant wavelength is amplified between the reflective electrode and the semitransmissive / semi-reflective electrode, causing resonance. It can attenuate light of wavelengths that are not present.

[0215] Furthermore, the light reflected back by the reflective electrode (the first reflected light) is semi-transmitted from the light-emitting layer. • Because it causes significant interference with the light (first incident light) that directly enters the semi-reflecting electrode, the reflective electrode and The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is amplified). It is preferable to adjust the wavelength of the emitted light. By adjusting the optical distance, the first By aligning the phase of the reflected light and the first incident light, the light emitted from the light-emitting layer can be further amplified. ru.

[0216] Furthermore, even if the EL layer in the above configuration has a structure with multiple light-emitting layers, it may still be a single light-emitting layer The structure may also have the following characteristics, for example, in combination with the configuration of the tandem light-emitting device described above. Furthermore, multiple EL layers are provided in a single light-emitting device with a charge generation layer in between, and each EL layer This may also be applied to a configuration in which one or more light-emitting layers are formed.

[0217] Having a microcavity structure enhances the emission intensity in the front direction at specific wavelengths. This makes it possible to reduce power consumption. Furthermore, the four sub-colors red, yellow, green, and blue are used. In the case of a light-emitting device that displays images as is, in addition to the brightness enhancement effect of yellow light emission, all sub-pixels By applying a microcavity structure tailored to the wavelength of each color, a light-emitting device with excellent characteristics can be produced. It can be placed there.

[0218] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2. This makes it possible to obtain a light-emitting device with good characteristics. Specifically, the method described in Embodiment 2. Because light-emitting devices have good luminous efficiency, it is possible to create light-emitting devices with low power consumption. ru.

[0219] Up to this point, we have explained active-matrix light-emitting devices, but from here on we will discuss passive devices. A matrix-type light-emitting device will be described. Figure 7 shows a passive light-emitting device fabricated by applying the present invention. This shows a matrix-type light-emitting device. Figure 7(A) is a perspective view showing the light-emitting device, Figure 7( B) is a cross-sectional view obtained by cutting Figure 7(A) along the XY line. In Figure 7, on the substrate 951, An EL layer 955 is provided between electrode 952 and electrode 956. The end of electrode 952 is It is covered with an insulating layer 953. And a partition layer 954 is provided on top of the insulating layer 953. The side walls of the partition layer 954, as they approach the substrate surface, have a gap between one side wall and the other side wall. It has a slope that narrows as the partition becomes narrower. In other words, the cross-section of the partition wall layer 954 in the short-side direction is It is a shape, and the bottom edge (which faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) ) is the upper edge (the edge that faces the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). It is shorter than that. In this way, by providing the partition layer 954, light emission devices caused by static electricity, etc. This can prevent defects in the system. Furthermore, it can also be implemented in passive matrix type light-emitting devices. It uses the light-emitting device described in Form 2, and is a reliable light-emitting device, or has low power consumption. It can be made into a small light-emitting device.

[0220] The light-emitting device described above consists of numerous tiny light-emitting devices arranged in a matrix. Because these can be controlled, it can be suitably used as a display device for representing images. It is a light-emitting device.

[0221] Furthermore, this embodiment can be freely combined with other embodiments.

[0222] (Embodiment 4) In this embodiment, Figure 8 shows an example in which the light-emitting device described in Embodiment 2 is used as an illumination device. I will explain while referring to Figure 8(B). Figure 8(B) is a top view of the lighting device, and Figure 8(A) is a top view of Figure 8(B). This is a cross-sectional view.

[0223] The lighting device in this embodiment has a light-transmitting substrate 400 which is a support, and a first An electrode 401 is formed. The first electrode 401 is the first electrode 10 in Embodiment 1. This corresponds to 1. When light is extracted from the first electrode 401 side, the first electrode 401 is light-transmitting. It is formed from a material having [a certain characteristic].

[0224] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0225] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is in Embodiment 1 The configuration of the EL layer 103 in the light-emitting units 511, 512 and the charge generation layer 513 This corresponds to a combined configuration, etc. Please refer to the relevant description for details on these configurations.

[0226] The EL layer 403 is covered to form the second electrode 404. The second electrode 404 is in Embodiment 1. This corresponds to the second electrode 102. When light emission is taken from the first electrode 401 side, the second The electrode 404 is formed of a highly reflective material. The second electrode 404 is pad 412 Voltage is supplied by connecting it to it.

[0227] The above describes a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. The lighting device shown in this embodiment has a light-emitting device with high luminous efficiency. Since it is a chair, the lighting device in this embodiment is a lighting device with low power consumption. It is possible.

[0228] The substrate 400 on which the light-emitting device having the above configuration is formed and the sealing substrate 407 are sealed The lighting device is completed by fixing and sealing it using materials 405 and 406. Either 405 or 406 is acceptable. Also, the inner sealant 406 (Figure 8 (B) (Not shown) A desiccant can also be mixed in, which allows it to absorb moisture. This leads to improved reliability.

[0229] Furthermore, the pad 412 and a portion of the first electrode 401 are extended outside the sealing materials 405 and 406. By providing it, it can be used as an external input terminal. Also, a converter can be placed on top of it. An IC chip 420 or similar, which incorporates such features, may also be provided.

[0230] As described above, the lighting device described in this embodiment has an EL element and the light-emitting device described in Embodiment 2. This allows for a light-emitting device with low power consumption.

[0231] (Embodiment 5) In this embodiment, an example of an electronic device that includes the light-emitting device described in Embodiment 2 as a part thereof is provided. This will be explained. The light-emitting device described in Embodiment 2 has good luminous efficiency and low power consumption. It is a small light-emitting device. As a result, the electronic device described in this embodiment has low power consumption. It is possible to create an electronic device that has a small light-emitting part.

[0232] Examples of electronic devices to which the above-mentioned light-emitting device is applied include television equipment (televisions, and (Also called a television receiver), monitors for computers, digital cameras, digital cameras Digital video cameras, digital photo frames, mobile phones (both mobile phones and mobile phone devices) (Examples include) portable game consoles, personal digital assistants, audio playback devices, and large game machines such as pachinko machines. These are some examples. Specific examples of these electronic devices are shown below.

[0233] Figure 9(A) shows an example of a television system. The television system has a housing 710 The display unit 7103 is incorporated into part 1. Also, the housing is connected by the stand 7105. This shows the configuration supporting 7101. The display unit 7103 can display video. The display unit 7103 is capable of arranging the light-emitting devices described in Embodiment 2 in a matrix. It is composed of the following.

[0234] The television equipment is operated using the control switches on the housing 7101 and a separate remote control unit. This can be done using 7110. The operation key 7109 on the remote control unit 7110 Furthermore, it is possible to control the channel and volume, and manipulate the image displayed on the display unit 7103. It can be made. Also, the remote control operator 7110 can be connected to the remote control operator 7110. A display unit 7107 that displays the output information may also be provided.

[0235] The television system shall consist of a receiver, modem, etc. It can receive television broadcasts, and also communicate via wired or wireless connection through a modem. By connecting to a network, one-way (sender to receiver) or two-way (sender to receiver) communication is possible. It is also possible to communicate information between recipients, or between recipients themselves.

[0236] Figure 9(B1) is a computer, consisting of the main unit 7201, the casing 7202, the display unit 7203, and a key - Includes board 7204, external connection port 7205, pointing device 7206, etc. Furthermore, this computer arranges the light-emitting devices described in Embodiment 2 in a matrix. It is manufactured by using it in the display unit 7203. The computer in Figure 9(B1) is It may also be in a form like 9(B2). The computer in Figure 9(B2) has a keyboard 7 204, a second display unit 7210 is provided instead of the pointing device 7206. The second display unit 7210 is a touch panel, and the second display unit 7210 displays Input can be performed by operating the indicated input display with your finger or a dedicated pen. It can. In addition, the second display unit 7210 can display not only input information but also other images. It is also possible that the display unit 7203 is a touch panel. Because it is connected via a cable, the screen may be scratched or damaged when storing or transporting it. This can also prevent the occurrence of such problems.

[0237] Figure 9(C) shows an example of a mobile terminal. The mobile phone is incorporated into the housing 7401. In addition to the display unit 7402, there are operation buttons 7403, an external connection port 7404, and a speaker 740 5. It is equipped with a microphone 7406, etc. The mobile phone is the light-emitting device described in Embodiment 2. It has a display unit 7402 made by arranging devices in a matrix.

[0238] The mobile terminal shown in Figure 9(C) allows users to input information by touching the display unit 7402 with their fingers or other objects. It can also be configured to allow for making phone calls or composing emails. Operations such as this can be performed by touching the display unit 7402 with a finger or the like.

[0239] The display unit 7402 has three main modes. The first is a display that primarily displays images. The first mode is display mode, the second is input mode which is mainly for inputting information such as characters. The third is display mode. This is a display + input mode, which is a combination of two modes: display mode and input mode.

[0240] For example, when making a phone call or composing an email, the display unit 7402 is used for text input. The primary mode is text input, and you should perform the input operation for the characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402. It seems so.

[0241] Furthermore, the mobile device has sensors inside that detect tilt, such as a gyroscope and an accelerometer. By installing the device, the orientation of the mobile terminal (portrait or landscape) is determined, and the screen display of the display unit 7402 is displayed accordingly. The display can be set to switch automatically.

[0242] Furthermore, screen modes can be switched by touching the display unit 7402 or by operating the housing 7401. This is done by operating button 7403. Also, the type of image displayed on display unit 7402 Therefore, it is also possible to switch between them. For example, the image signal displayed on the display unit is a video signal. Switch to display mode if it's data, or to input mode if it's text data.

[0243] Furthermore, in input mode, the signal detected by the optical sensor of the display unit 7402 is detected and displayed If there is no input via touch operation on unit 7402 for a certain period of time, the screen mode will be changed to input mode. You may also control the system to switch from that display mode to a different mode.

[0244] The display unit 7402 can also function as an image sensor. For example, the display unit 74 By touching device 02 with the palm or finger, the user can authenticate their identity by capturing images of their palm print, fingerprints, etc. Furthermore, the display unit may have a backlight that emits near-infrared light or a sensing device that emits near-infrared light. Using a suitable light source, it is also possible to image finger veins, palmar veins, and other veins.

[0245] The configuration shown in this embodiment is a combination of the configurations shown in Embodiments 1 to 4 as appropriate. They can be used together.

[0246] As described above, the application range of the light-emitting device equipped with the light-emitting device described in Embodiment 2 is extremely broad. This light-emitting device can be applied to electronic devices in all fields. Embodiment 2 By using the described light-emitting device, it is possible to obtain electronic devices with low power consumption.

[0247] Figure 10(A) is a schematic diagram showing an example of a cleaning robot.

[0248] The cleaning robot 5100 has a display 5101 located on the top and multiple displays located on the sides. It has several cameras 5102, brushes 5103, and operation buttons 5104. However, the underside of the 5100 cleaning robot is equipped with wheels, a suction port, etc. The 5100 robot also includes an infrared sensor, ultrasonic sensor, acceleration sensor, and piezo sensor. It is equipped with various sensors such as optical sensors and gyro sensors. Also, the cleaning robot 5 Unit 100 is equipped with wireless communication means.

[0249] The cleaning robot 5100 moves autonomously, detects the dirt 5120, and uses the suction port located on its underside to... It can then vacuum up the dust.

[0250] Furthermore, the cleaning robot 5100 analyzes images captured by the camera 5102, and detects walls, furniture, or It can determine the presence or absence of obstacles such as steps. Furthermore, image analysis can detect wiring and other obstacles. If an object that may become entangled in brush 5103 is detected, the rotation of brush 5103 will be stopped. can.

[0251] The display 5101 can show the battery level, the amount of dust collected, etc. Yes, it's possible. You can also display the path taken by the cleaning robot 5100 on the display 5101. Furthermore, the display 5101 is a touch panel, and the operation buttons 5104 are on the display. It may also be provided in I-5101.

[0252] The cleaning robot 5100 can communicate with portable electronic devices 5140 such as smartphones. Yes, it is possible. Images captured by camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the 5100 cleaning robot can know what's happening in the room even when they're away from home. It is possible to display the information on the display 5101 on portable electronic devices such as smartphones. You can also check it there.

[0253] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0254] The robot 2100 shown in Figure 10(B) consists of a computing unit 2110, an illuminance sensor 2101, and a microcontroller. Crossphone 2102, upper camera 2103, speaker 2104, display 2105, It is equipped with a lower camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0255] Microphone 2102 has the function of detecting the user's voice and ambient sounds, etc. Speaker 2104 has the function of emitting sound. Robot 2100 has a microphone Using the 2102 and speaker 2104, communication with the user is possible. It is possible.

[0256] The display 2105 has the function of displaying various information. The robot 2100 is The user can display the desired information on the display 2105. The 2105 may have a touch panel. Also, the display 2105 is removable. It can be any information terminal capable of charging, and by installing it in a fixed position on the robot 2100, And it enables the transfer of data.

[0257] The upper camera 2103 and lower camera 2106 are used to image the area around the robot 2100. It has the ability to detect obstacles. Furthermore, the obstacle sensor 2107 uses the moving mechanism 2108 to detect robot 210 Robot 21 can detect the presence or absence of obstacles in the direction of travel as it moves forward. 00 uses the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107 The light-emitting device according to one aspect of the present invention can recognize its surroundings and move safely. It can be used in display 2105.

[0258] Figure 10(C) shows an example of a goggle-type display. For example, the components include the casing 5000, the display unit 5001, the speaker 5003, and the LED lamp 5004. , connection terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotational speed) Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, electric current, voltage, power, (including functions for measuring radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), It includes an ICrophone 5008, a display unit 5002, a support unit 5012, an earphone 5013, etc. .

[0259] The light-emitting device according to one aspect of the present invention can be used in the display unit 5001 and the display unit 5002. .

[0260] Figure 11 shows the light-emitting device described in Embodiment 2 used in a desk lamp, which is a lighting device. This is an example. The desk lamp shown in Figure 11 has a housing 2001 and a light source 2002. For 002, the lighting device described in Embodiment 3 may be used.

[0261] Figure 12 shows the light-emitting device described in Embodiment 2 used as an indoor lighting device 3001. This is an example. The light-emitting device described in Embodiment 2 is a light-emitting device with high luminous efficiency. This allows for a lighting device with low power consumption. Also, the light-emitting device described in Embodiment 2 Because chairs can be made to cover a large area, they can be used as large-area lighting devices. The light-emitting device described in Embodiment 2 is thin and can therefore be used as a thinned lighting device. This becomes possible.

[0262] The light-emitting device described in Embodiment 2 can be used on the windshield, dashboard, etc. of an automobile. It can also be installed. Figure 13 shows the light-emitting device described in Embodiment 2 in an automobile refrigerant This shows one embodiment for use in the glass, dashboard, etc. Display area 5200 to display area 5 203 is a display provided using the light-emitting device described in Embodiment 2.

[0263] Display area 5200 and display area 5201 are in an embodiment provided on the windshield of an automobile. A display device equipped with the light-emitting device described in 2. The light-emitting device described in Embodiment 2. This is achieved by fabricating the first and second electrodes with translucent electrodes, so that the opposite side is transparent. It can be used as a display device that is visible through a transparent, so-called see-through state. If it's a display, even if it's installed on the windshield of a car, it won't obstruct the view. It can be installed. Furthermore, if transistors or other components for driving are to be installed, organic semiconductors may be used. Organic transistors made of conductive materials, transistors using oxide semiconductors, etc., which have light-transmitting properties It is best to use a transistor that performs this function.

[0264] The display area 5202 is equipped with the light-emitting device described in Embodiment 2, which is provided in the pillar portion. This is a display device. The display area 5202 displays images from an imaging device installed on the vehicle body. By extending it, the view obstructed by the pillar can be compensated for. Also, similarly, The display area 5203 provided on the shoeboard section allows the view obstructed by the vehicle body to be seen by the car. By displaying images from externally mounted imaging devices, blind spots are compensated for, and safety is enhanced. It can be done by projecting images that complement the parts that are not visible, making it more natural. Safety checks can be performed without any sense of unease.

[0265] The display area 5203 also displays navigation information, speed, engine RPM, air conditioning settings, etc. It can provide various other types of information. The displayed items can be adjusted according to the user's preferences. The layout can be changed. Note that this information is displayed in display area 5200 or the display area It can also be provided in area 5202. In addition, display areas 5200 to 5203 are illuminated It can also be used as a lighting device.

[0266] Figures 14(A) and (B) also show a foldable portable information terminal 5150. The portable information terminal 5150 consists of a housing 5151, a display area 5152, and a bendable portion 515 It has 3. Figure 14(A) shows the portable information terminal 5150 in its unfolded state. Figure 14( B) shows the portable information terminal in its folded state. The portable information terminal 5150 has a large display area Despite having a 5152mm field of view, it folds up compactly and is highly portable.

[0267] The display area 5152 can be folded in half by the bending portion 5153. Bending portion 515 3 consists of an expandable member and multiple support members, and when folded, the expandable The member stretches, and the bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It folds up.

[0268] Note that the display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). It may also be a device. The light-emitting device according to one aspect of the present invention can be used in the display area 5152. Cut.

[0269] Figures 15(A) to (C) also show a foldable portable information terminal 9310. Figure 15 (A) shows the portable information terminal 9310 in its unfolded state. Figure 15(B) shows the unfolded state or This shows the portable information terminal 9310 in an intermediate state, transitioning from one folded state to the other. Figure 15(C) shows the folded state of the personal digital assistant 9310. Personal digital assistant 9310 It offers excellent portability when folded and a seamless, wide display area when unfolded. This provides excellent readability in the display.

[0270] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). It may also be an input / output device. In addition, the display panel 9311 is connected via the hinge 9313. By bending the two housings 9315, the mobile information terminal 9310 is unfolded. It can be reversibly transformed from a folded state. A light-emitting device according to one aspect of the present invention It can be used with the display panel 9311. [Examples]

[0271] In this embodiment, a light-emitting device using a low refractive index organic compound and a light-emitting device using a comparative material are presented. The results of a detailed investigation into the drive voltage with the vise are shown. The main organic compounds used in this example The structural formula of the compound is shown below.

[0272] [ka]

[0273] [ka]

[0274] (Method for fabricating light-emitting devices 1 to 7) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. The first electrode 101 was formed by depositing a film using the 3D method. The film thickness was 55 nm, and the electrode surface The product was set to 2mm x 2mm.

[0275] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0276] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0277] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, By using a resistive heating deposition method, low refractive index organic compounds (low-n HTM) and electrons are deposited. The xepta material (OCHD-001) and the low-n HTM are used in a weight ratio of 1:0.1 (=low-n HTM: A hole injection layer 111 was formed by co-depositing 10 nm of material to create OCHD-001.

[0278] Furthermore, the low-n HTM mentioned above is represented by the above structural formula (i) in the light-emitting device 1-1. N-3',5'-Ditherlybutyl-1,1'-Biphenyl-4-yl-N-1,1 '-Biphenyl-2-yl-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: In the light-emitting device 2-1 to light-emitting device 2-3, the above structure is used for mmtBuBioFBi). N,N-bis(4-cyclohexylphenyl)-9,9-dimethyl, represented by formula (ii). -9H-fluorene-2-amine (abbreviated as dchPAF) is used in light-emitting device 3-1 and In the light-emitting device 3-2, the structure is represented by the above structural formula (iii) N-[(3',5'-ditransient [Cyrohexylbutyl)-1,1'-biphenyl-4-yl]-N-(4-cyclohexylphenyl (Lu)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBuBichP) In the light-emitting device 4, AF) is represented by the above structural formula (iv) N-(3,5-ditas (Leabutylphenyl)-N-(3',5',-Ditert-butyl-1,1'-Biphenyl) Nyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtB) In light-emitting devices 5-1 to 5-3, the above structure is used for uBimmtBuPAF). The formula (v) represents N-(1,1'-biphenyl-2-yl)-N-(3,3'',5' ,5''-Tetra-tert-butyl-1,1':3',1''-Terphenyl-5-I (L)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBumTPoF) Bi-02) is used in light-emitting devices 6-1 to 6-3 with the above structural formula (vi). The expressed N-(4-cyclohexylphenyl)-N-(3,3'',5',5''-teto La-tert-butyl-1,1':3',1''-terphenyl-5-yl)-9,9- Dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPChPAF-02) In light-emitting devices 7-1 to 7-4, the N is represented by the above structural formula (vii). -(3,3'',5,5''-Tetra-t-butyl-1,1':3',1''-Tafe Nyl-5'-yl)-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H- Fluoren-2-amine (abbreviated as mmtBumTPchPAF) was used in each case.

[0279] Furthermore, the same low-n HTM as light-emitting devices 2-1 to 2-3, etc. When there are multiple light-emitting devices using this technology, they may be collectively referred to as light-emitting device 2.

[0280] Next, on the hole injection layer 111, mmtBuBioFBi is injected into the light-emitting device 1-1. In devices 2-1 to 2-3, dchPAF is used, and in 3-1 and Light-emitting device 3-2 uses mmtBuBichPAF, and light-emitting device 4 uses mmtBuB immtBuPAF is used in light-emitting devices 5-1 to 5-3, and mmtBumT PoFBi-02 is used with mmtBumTP in light-emitting devices 6-1 to 6-3. ChPAF-02 is used in the luminescent devices 7-1 through 7-4 with mmtBumTP After depositing chPAF to a film thickness of 30 nm, the structure is represented by the above structural formula (viii). N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-turf The light-emitting device 1-1 and light-emitting device 2-1 use a film made of phenyl (abbreviation: DBfBB1TP). The film thickness of the light-emitting devices is 15 nm, and the other light-emitting devices are deposited to a film thickness of 10 nm. A hole transport layer 112 was formed.

[0281] Next, the above structural formula (ix) represents 9-(1-naphthyl)-10-[4-(2-naphthyl] [Tyl)phenyl]anthracene (abbreviation: αN-βNPAnth) is represented by the above structural formula (x). 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-f [enylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10 PCA2Nbf(IV)-02) and αN-βNPAnth in a weight ratio of 1:0.015 (=αN-βNPAnth :3,10PCA2Nbf(IV)-02), co-deposited to a film thickness of 25 nm to produce light emission. Layer 113 was formed.

[0282] Subsequently, on the light-emitting layer 113, 2-{4-[9,10-di( represented by the above structural formula (xi)) Naphthalene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzoyl Midazole (abbreviation: ZADN) and 8-quinolinolato represented by the above structural formula (xii) Lithium (abbreviated as Liq) and ZADN are mixed in a weight ratio of 1:1 (=ZADN:Liq), with a film thickness of 25nm. An electron transport layer 114 was formed by co-deposition in such a manner.

[0283] After forming the electron transport layer 114, Liq is deposited at a 1 nm thickness to form the electron injection layer 115. Next, a second electrode 102 is formed by depositing aluminum to a thickness of 200 nm. We formed and fabricated a light-emitting device.

[0284] (Method for fabricating comparative light-emitting device 1) Comparative light-emitting device 1 uses mmtBuBioFBi in light-emitting device 1-1, as described above. The formula (xiii) represents N-(1,1'-biphenyl-4-yl)-N-[4-(9 -phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H- Aside from changing to ruolene-2-amine (abbreviation: PCBBiF), the light-emitting device 1-1 is the same. It was made in the same way.

[0285] The element structures of the above-mentioned light-emitting device and comparative light-emitting device 1 are summarized in the table below.

[0286] [Table 1]

[0287] Of the above light-emitting devices, light-emitting devices 1 to 3 are the light-emitting devices of the embodiment. It is a chair.

[0288] Furthermore, the low-n HTM used in the hole injection layer and hole transport layer, and the reference P The ordinary refractive index n of CBBiF at a wavelength of 458 nm o , birefringence Δn and orientation order The parameter S is shown in the table below.

[0289] [Table 2]

[0290] The above-mentioned light-emitting device and comparative light-emitting device were placed in a glove box under a nitrogen atmosphere. , the process of sealing the element with a glass substrate to prevent exposure to the atmosphere (applying a sealing material around the element). Furthermore, UV treatment and heat treatment at 80°C for 1 hour were performed during sealing.

[0291] Figure 16 shows the difference in driving voltage (Δ) between the comparison light-emitting device and each light-emitting device when driven at 1mA. V) is the value on the y-axis, and the birefringence Δn of the low-n HTM used at 458nm light is on the x-axis. The graph shows the values ​​plotted as follows. Note that the plots indicated by crosses omit further details. However, it has a structure similar to light-emitting devices 1 to 7, and is different from low-n HTM The results for light-emitting devices fabricated using this method are shown.

[0292] Figure 16 shows that a low-n HTM with birefringence Δn between 0 and 0.008 is used for luminescence development. Chair 1 and light-emitting device 2 clearly have a smaller ΔV compared to other light-emitting devices, and the drive power It was found to be a low-pressure light-emitting device.

[0293] Similarly, Figure 17 shows the comparison light-emitting device and each light-emitting device when driven at 1mA. The difference in driving voltage (ΔV) is the value on the y axis, and the orientation of the deposited film of the low-n HTM used is... The parameter S(low-n) is the longest wavelength in the absorption spectrum of HTM. The orientation order parameter for light of the wavelength corresponding to the absorption peak is taken as the value of the x-axis. The plotted graph is shown. Similar to Figure 16, the plots indicated by crosses represent light-emitting devices 1 to A light-emitting device having a similar structure to light-emitting device 7, fabricated using a different low-n HTM. The results from Vice are shown. Note that the absorption spectrum of each low-n HTM in the deposited film is shown. The details are as shown in Figure 26.

[0294] Figure 17 shows the deposition process with respect to light at the wavelength of the absorption peak located at the longest wavelength in the absorption spectrum. The film orientation order parameter S is in the range of -0.070 to 0.00. The light-emitting devices 1 and 2 using n HTM are brighter compared to other light-emitting devices. It was found that the light-emitting device had a very small ΔV and a low driving voltage.

[0295] Furthermore, the light-emitting device 3 has a high birefringence Δn of 0.036, and the orientation order parameter S Despite the relatively low value of -0.095, other low-n HTM-based luminescence devices Compared to chairs, ΔV is kept low. The low light used in this light-emitting device -n HTM is similar to the low-n HTM used in light-emitting device 1, Paravit Phenyl structures, particularly those in which the 1,1'-biphenyl-4-yl group is directly bonded to the nitrogen of the amine. Because it has this feature, it is driven at a low drive voltage.

[0296] Furthermore, low-n HTM has a low refractive index, and therefore uses alkyl groups with 3 to 8 carbon atoms. and has multiple cycloalkyl groups having 6 to 12 carbon atoms, but the above 1,1'-biphenyl- When these groups are bonded to a 4-yl group, at any of the 2', 3', 4', or 5' positions, In particular, binding to the 3' and 5' positions inhibits the carrier transportability of low-n HTM. Furthermore, this is preferable because it leads to a reduction in the drive voltage.

[0297] On the other hand, like the low-n HTM of the light-emitting device 4, 1,1'-biphenyl-4-i Even if the aryl group is directly bonded to nitrogen, it can still bond to other aryl groups bonded to the same nitrogen. Starting from the carbon atom bonded to the nitrogen atom in the benzene ring closest to the nitrogen atom in question, At the t position, the above C3 to C8 alkyl group and C6 to C12 cycloalkyl group are It has been found that when coupled, the drive voltage increases because it reduces carrier transportability. ru.

[0298] As described above, in light-emitting devices using low-n HTM, the birefringence Δn or the distribution By using a low-n HTM with a certain range of direction order parameter S, It was found that a low dynamic voltage light-emitting device could be obtained. Also, low-n HT In a light-emitting device using M, a low-n HTM having a specific structure is used. Therefore, if the birefringence Δn or orientation order parameter S is in a wider range than the above range It was found that a light-emitting device with a low driving voltage can be obtained. [Examples]

[0299] This embodiment will describe in detail a light-emitting device using an organic compound according to one aspect of the present invention. The structural formulas of representative organic compounds used in this example are shown below.

[0300] [ka]

[0301] (Methods for fabricating light-emitting devices 1-2, 2-4, and 3-3) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. The first electrode 101 was formed by depositing a film using the 3D method. The film thickness was 55 nm, and the electrode surface The product was set to 2mm x 2mm.

[0302] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0303] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0304] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, By using a resistive heating deposition method, low refractive index organic compounds (low-n HTM) and electron activators are deposited. The septa material (OCHD-001) and HTM:O are used in a weight ratio of 1:0.1 (=low-n HTM:O A hole injection layer 111 was formed by co-depositing 10 nm of material to create CHD-001.

[0305] The above low-n HTM is represented by the above structural formula (i) in the light-emitting device 1-2. N-3',5'-Ditherlybutyl-1,1'-Biphenyl-4-yl-N-1,1 '-Biphenyl-2-yl-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: In the light-emitting device 2-4, the N represented by the above structural formula (ii) is used. N-bis(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene-2 - The amine (abbreviation: dchPAF) is represented by the above structural formula (iii) in the light-emitting device 3-3. N-[(3',5'-Ditterbutyl)-1,1'-Biphenyl-4-yl ]-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene-2- Each of the following was used: an amine (abbreviated as mmtBuBichPAF).

[0306] Next, mmtBuBioFBi is injected onto the hole injection layer 111 in the light-emitting device 1-2. Devices 2-4 use dchPAF, while light-emitting device 3-3 uses mmtBuBichPAF. After depositing the material to a thickness of 30 nm, the N,N-bi represented by the above structural formula (viii) is deposited. Su[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviated) A hole transport layer 112 is formed by depositing (name: DBfBB1TP) to a thickness of 15 nm. Ta.

[0307] Next, the above structural formula (ix) represents 9-(1-naphthyl)-10-[4-(2-naphthyl] [Tyl)phenyl]anthracene (abbreviation: αN-βNPAnth) is represented by the above structural formula (x). 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-f [enylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10 PCA2Nbf(IV)-02) and αN-βNPAnth in a weight ratio of 1:0.015 (=αN-βNPAnth :3,10PCA2Nbf(IV)-02), co-deposited to a film thickness of 25 nm to produce light emission. Layer 113 was formed.

[0308] Subsequently, on the light-emitting layer 113, 2-{4-[9,10-di( represented by the above structural formula (xi)) Naphthalene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzoyl Midazole (abbreviation: ZADN) and 8-quinolinolato represented by the above structural formula (xii) Lithium (abbreviated as Liq) and ZADN are mixed in a weight ratio of 1:1 (=ZADN:Liq), with a film thickness of 25nm. An electron transport layer 114 was formed by co-deposition in such a manner.

[0309] After forming the electron transport layer 114, Liq is deposited at a 1 nm thickness to form the electron injection layer 115. Next, a second electrode 102 is formed by depositing aluminum to a thickness of 200 nm. We formed and fabricated a light-emitting device.

[0310] (Method for fabricating the comparative light-emitting device 10) The comparative light-emitting device 10 uses the mmtBuBioFBi in light-emitting devices 1-2 as described above. The structural formula (xiii) represents N-(1,1'-biphenyl-4-yl)-N-[4-( 9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H- Except for the change to fluoren-2-amine (abbreviation: PCBBiF), it is the same as light-emitting device 1-2. It was made in this way.

[0311] The element structures of the above-mentioned light-emitting device and the comparative light-emitting device are summarized in the table below.

[0312] [Table 3]

[0313] [Table 4]

[0314] Furthermore, the low-n HTM vapor-deposited film used for the hole injection layer and the hole transport layer, and the comparative material The ordinary refractive index n of the PCBBiF deposited film o , birefringence Δn and orientation order parameter S The table below shows the results.

[0315] [Table 5]

[0316] The above-mentioned light-emitting device and comparative light-emitting device 10 are placed inside a glove box in a nitrogen atmosphere. Then, the process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (sealing material) After applying this around the element, UV treatment and heat treatment at 80°C for 1 hour are performed during sealing, The initial characteristics of the light-emitting device were measured. The glass used to fabricate the light-emitting device was also used. No special measures have been taken on the circuit board to improve extraction efficiency.

[0317] Light-emitting devices 1-2, 2-4, 3-3, and comparison light-emitting devices Figure 18 shows the luminance-current density characteristics of S10, Figure 19 shows the luminance-voltage characteristics, and Figure 19 shows the current efficiency-luminance characteristics. Figure 20 shows the characteristics, Figure 21 shows the current density-voltage characteristics, and Figure 22 shows the power efficiency-brightness characteristics. The quantum efficiency-luminance characteristics are shown in Figure 23, and the emission spectra are shown in Figure 24. Furthermore, each light-emitting device... 1000 cd / m² 2 Table 6 shows the main characteristics in the vicinity. Note that luminance and CIE chromaticity are... A spectroradiometer (Topcon UR-UL1R) was used to measure the emission spectrum. The measurements were taken at room temperature. Furthermore, the external quantum efficiency was calculated using the measured brightness and emission spectrum, and the light distribution was determined. The calculation was performed assuming that the characteristics are of the Lambertsian type.

[0318] [Table 6]

[0319] As shown in Figures 18 to 24, the light-emitting device according to one aspect of the present invention is equivalent to the comparative light-emitting device 10. While indicating the driving voltage, a low refractive index organic compound is used in the hole injection layer and hole transport layer. This is a light-emitting device with excellent luminescence efficiency, where the external quantum efficiency is significantly improved by the presence of [a specific element / feature]. It can be seen that... Therefore, a light-emitting device according to one aspect of the present invention is a light-emitting device with low power consumption... It is S.

[0320] Furthermore, the above-mentioned light-emitting devices 1-2, 2-4, 3-3, and comparison Current density of light-emitting device 10: 50 mA / cm² 2The change in brightness with respect to operating time is shown. The graph is shown in Figure 25. As shown in Figure 25, a light-emitting device according to one aspect of the present invention Light-emitting devices 1-2, 2-4, and 3-3 have a good lifespan. It was also discovered that it is a light-emitting device. [Examples]

[0321] <<Synthesis Example 1>> In this synthesis example, the organic compound according to one embodiment of the present invention used in the example is N-(3',5' -Ditherlybutyl-1,1'-biphenyl-4-yl)-N-(1,1'-biphenyl Nyl-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtB) The synthesis method for uBioFBi will be explained. The structure of mmtBuBioFBi is shown below. show.

[0322] [ka]

[0323] 4-chloro-3',5'-di-tert-butyl-1,1'-biphenyl in a three-necked flask. 2.22g (7.4 mmol), 2-(2-biphenylyl)amino-9,9-dimethyl phosphate Luoren 2.94g (8.1 mmol), sodium tert-butoxide (abbreviation: t Add 2.34g (24.4 mmol) of BuONa and 37mL of xylene, and remove under reduced pressure. After gas treatment, the flask was purged with nitrogen. Di-t-butyl(1-methyl) was added to this mixture. -2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP(registered trademark)) 107.6 mg (0.31 mmol), allyl palladium chloride dimer (abbreviation: [P dCl(allyl)]2) 28.1 mg (0.077 mmol) was added to this mixture. It was heated at 100°C for about 4 hours. After that, the flask temperature was returned to about 70°C, and water was added. mL was added, and the solid precipitated. The precipitated solid was filtered off. The filtrate was concentrated to obtain the solution. The solution was purified by silica gel column chromatography. The resulting solution was concentrated and then ethanol The process of adding and reconcentrating was repeated three times, and the resulting ethanol suspension was recrystallized. Approximately -1 After cooling to 0°C, the precipitate is filtered, and the resulting solid is dried under reduced pressure at approximately 130°C to obtain the target product. A white solid was obtained in 2.07 g with a yield of 45%. The synthesis scheme for this synthesis example is shown below. .

[0324] [ka]

[0325] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in this synthesis example ( 1 Analysis results by 1H-NMR This is shown below. From this, it can be concluded that mmtBuBioFBi was successfully synthesized in this synthesis example. That's what I found out.

[0326] 1 H-NMR(CDCl3,500MHz):δ=1.29(s,6H),1.38(s ,18H),6.76(dd,J1=8.0Hz,J2=2.0Hz,1H),6.87 (d,J=2.5Hz,1H),7.00-7.08(m,5H),7.18-7.23 (m,3H),7.27-7.43(m,12H),7.55(d,J=7.5Hz,1 H).

[0327] Next, 2.0 g of the obtained solid was purified by sublimation using the train sublimation method. The process involved heating at 225°C under conditions of a pressure of 3.77 Pa and an argon flow rate of 15.0 mL / min. The process was carried out. After sublimation purification, 1.9 g of a white solid was obtained with a recovery rate of 95%.

[0328] Furthermore, the refractive index of mmtBuBioFBi is measured using a spectroscopic ellipsometer (J.A. W.A. W.A.). Measurements were taken using a M-2000U (manufactured by Mu Japan Co., Ltd.). For the measurement, each layer of material was placed on a quartz substrate. A film with a thickness of approximately 50 nm was used, which was deposited by vacuum deposition.

[0329] As a result, mmtBuBioFBi covers the entire blue light emission region (455nm to 465nm). In the region, the ordinary refractive index is in the range of 1.50 to 1.75, and also at 633 nm. The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. .

[0330] Next, the hole mobility of mmtBuBioFBi was calculated. Hole mobility is calculated by considering only the holes. Methods for calculating from the electrical characteristics of the measuring element used as the carrier through simulation, and impedance The results were calculated using two methods: spectroscopy (IS method) and spectroscopy.

[0331] In the IS method, a small sinusoidal voltage signal (V=V0[exp(jωt)]) is applied to the EL element. The current amplitude of the response current signal (I=I0exp[j(ωt+φ)]) and the phase of the input signal From the difference, we can find the impedance of the EL element (Z=V / I). Low frequency voltage from high frequency voltage. By changing it to this extent and applying it to the element, it has various relaxation times that contribute to the impedance. The components can be separated and measured.

[0332] Here, the admittance Y (=1 / Z), which is the reciprocal of impedance, is given by the following equation (1): It can be expressed in terms of conductance G and susceptance B.

[0333]

number

[0334] Furthermore, the single-charge injection model shows that, respectively, Equations (2) and (3) can be calculated. Here, g (equation (4)) is the differential conductor. This is tance. In the formula, C is capacitance, θ is ωt, and the travel angle is... ω represents the angular frequency. t is the travel time, and d is the film thickness. The analysis uses the current equation and Poisson's equation. The equation for current continuity is used, and the existence of diffusion current and trap levels is ignored.

[0335]

number

[0336] The -ΔB method is a method for calculating mobility from the frequency characteristics of capacitance. The ωΔG method is a method for calculating mobility from the frequency characteristics of a device.

[0337] In practice, first, a measuring element is fabricated for the material whose carrier mobility is to be determined. A measuring element is an element designed so that only holes flow as carriers. The specification describes a method for calculating mobility from the frequency characteristics of capacitance (-ΔB method).

[0338] The table below shows the element structure of the measuring element. In the table, APC is silver (Ag) and palladium ( Pd) and copper (Cu) alloy film, ITSO is indium tin oxide containing silicon dioxide, OCHD -001 is an electronic acceptor material, MoOx is molybdenum oxide, and Al is aluminum. It is possible to calculate the mobility of the material used in the second layer, which is formed with a film thickness of 500 nm. Cut.

[0339] [Table 7]

[0340] Figure 27 shows the current density-voltage characteristics of the measuring element.

[0341] Impedance measurement is performed by applying a DC voltage in the range of 5.0V to 9.0V while simultaneously measuring the AC voltage. Measurements were taken under the conditions of 70mV and a frequency of 1Hz to 3MHz. The impedance obtained here Capacitance is calculated from admittance (equation (1) above), which is the reciprocal of dance.

[0342] The frequency characteristics of capacitance C are determined by the spatial charge of carriers injected by a small voltage signal. This is obtained when the load cannot fully follow the minute AC voltage, resulting in a phase difference in the current. Here, the travel time of the carriers in the membrane is the time T it takes for the injected carriers to reach the counter electrode. It is defined and expressed by the following equation (5), where L is the film thickness.

[0343]

number

[0344] The negative susceptance change (-ΔB) is the value obtained by multiplying the capacitance change -ΔC by the angular frequency ω (-ωΔ). This corresponds to C). Its lowest frequency peak frequency f' max (=ω max ( / 2π) and run From equation (3), the following relationship (6) can be derived between row time T and row time.

[0345]

number

[0346] The frequency characteristics of -ΔB calculated from the above measurements (i.e., when the DC voltage is 7.0V) were used to determine this. The lowest frequency peak frequency f' max Therefore, the travel time T can be determined (using the above formula (6 (See reference), from equation (5) above, in this case, we can determine the hole mobility at a voltage of 7.0V. This can be done. By performing similar measurements in the DC voltage range of 5.0V to 9.0V, each voltage ( Since hole mobility can be calculated at different electric field strengths, the dependence of mobility on electric field strength can also be measured.

[0347] The electric field strength dependence of the hole mobility of mmtBuBioFBi obtained by the calculation method described above. The properties are shown in Figure 28. The hole mobility calculated by simulation is shown by the dotted line. This is shown. Note that the horizontal axis in Figure 28 represents the electric field strength converted from voltage to the power of 1 / 2.

[0348] The simulation was performed using Setfos (Cybernet Systems)'s Drift-Dif The fusion module was used. The simulation parameters included the anode, I. The work function of TSO is 5.36 eV, and the work function of the cathode Al is 4.2 eV, mmt The HOMO level of BuBioFBi was set to -5.42 eV. Also, the charge in the second layer... Density 1.0 × 10 18 cm -3 That's what I decided.

[0349] The work function of the electrodes was measured in air using photoelectron spectroscopy (RIKEN Instruments, AC-2).

[0350] The HOMO level of organic compounds is measured by cyclic voltammetry (CV). The measurement was performed using an electrochemical analyzer (manufactured by B.A.S. Co., Ltd., model number: ALS model). Using Dell 600A or 600C, each compound is converted to N,N-dimethylformamide (abbreviated) The solution dissolved in :DMF was measured. In the measurement, the potential of the working electrode relative to the reference electrode was measured. The oxidation peak potential and reduction peak potential were obtained by varying the voltage within an appropriate range. Since the pole redox potential is estimated to be -4.94 eV, The HOMO levels of each organic compound were calculated from the numerical values ​​and the obtained peak potentials.

[0351] Thus, mmtBuBioFBi is 1 × 10 -3 cm 2 Having a hole mobility of / Vs or higher It was found to be an organic compound with good properties, including high hole mobility. [Examples]

[0352] ≪Synthesis Example 2≫ In this synthesis example, the organic compound N,N-bis(4-) used in the example is an organic compound according to one embodiment of the present invention. Cyclohexylphenyl)-9,9,-dimethyl-9H-fluoren-2-amine (abbreviation) The synthesis method for dchPAF is described below. The structure of dchPAF is shown below.

[0353] [ka]

[0354] <Step 1: N,N-bis(4-cyclohexylphenyl)-9,9,-dimethyl-9 Synthesis of H-fluoren-2-amine (abbreviation: dchPAF) 10.6g of 9,9-dimethyl-9H-fluoren-2-amine (51mm) in a three-necked flask. ol), 4-cyclohexyl-1-bromobenzene 18.2g (76 mmol), sodium Add 21.9g (228mmol) of um-tert-butoxide and 255mL of xylene. After degassing under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred. Here, allyl palladium chloride dimer(II) (abbreviated as [(Allyl) PdCl]2) 370 mg (1.0 mmol), di-tert-butyl (1-methyl-2) ,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP(registered trademark))16 60 mg (4.0 mmol) was added, and this mixture was heated at 120°C for approximately 5 hours. Afterward, the flask temperature was returned to approximately 60°C, and approximately 4 mL of water was added to precipitate the solid. The solid was filtered off. The filtrate was concentrated, and the resulting solution was subjected to silica gel column chromatography. It was purified using [method]. The resulting solution was concentrated to obtain a concentrated toluene solution. This toluene solution was then [method]. The solution was added dropwise to tanol and reprecipitation occurred. The precipitate was filtered at approximately 10°C, and the resulting solid was heated at approximately 80°C. The product was dried under reduced pressure to obtain 10.1 g of the target white solid in a yield of 40%. Step 1 The synthesis scheme is shown below.

[0355] [ka]

[0356] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 (H-NMR) The analysis results are shown below. This confirms that dchPAF was synthesized in this synthesis example. It was.

[0357] 1 H-NMR.δ(CDCl3):7.60(d,1H,J=7.5Hz),7.53( d,1H,J=8.0Hz),7.37(d,2H,J=7.5Hz),7.29(td ,1H,J=7.5Hz,1.0Hz),7.23(td,1H,J=7.5Hz,1. 0Hz),7.19(d,1H,J=1.5Hz),7.06(m,8H),6.97( dd,1H,J=8.0Hz,1.5Hz),2.41-2.51(brm,2H),1 .79-1.95(m,8H),1.70-1.77(m,2H),1.33-1.45 (brm, 14H), 1.19-1.30 (brm, 2H).

[0358] Next, 5.6 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 215°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 12.0 mL / min. The process was carried out. After sublimation purification, 5.2 g of a slightly yellowish-white solid was obtained with a recovery rate of 94%.

[0359] Furthermore, the refractive index of dchPAF is measured using a spectroscopic ellipsometer (J.A. Woo-ram Japan). Measurements were taken using a (M-2000U) manufactured by [company name]. For the measurement, the materials of each layer were vacuum vaporized on a quartz substrate. A film with a thickness of approximately 50 nm was used, deposited by a deposition method.

[0360] As a result, dchPAF exhibits paraphotorefractivity across the entire blue emission region (455nm to 465nm). The refractive index is in the range of 1.50 to 1.75, and the ordinary refractive index at 633 nm is also The refractive index was found to be in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. [Examples]

[0361] ≪Synthesis Example 3≫ In this synthesis example, the organic compound N-[(3',5'] of one embodiment of the present invention used in the example is used in the example. -Ditherlybutyl)-1,1'-biphenyl-4-yl]-N-(4-cyclohexyl Silphenyl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBu) The synthesis method for BichPAF is described below. The structure of mmtBuBichPAF is as follows. As shown.

[0362] [ka]

[0363] <Step 1: 3',5'-Diter-butyl-4-chloro-1,1'-biphenyl Synthesis of > 13.5g (50ml) of 3,5-diter-butyl-1-bromobenzene in a three-necked flask. mol), 4-chlorophenylboronic acid 8.2g (52.5 mmol), potassium carbonate 2 1.8g (158mmol), 125mL toluene, 31mL ethanol, 40mL water After adding the mixture and degassing under reduced pressure, the flask was purged with nitrogen. Acetic acid was added to this mixture. Radium 225 mg (1.0 mmol), Tris(2-methylphenyl)phosphine (abbreviated) Add 680 mg (2.0 mmol) of P(o-Tol)3) and incubate at 80°C for approximately 3 hours. The solution was subjected to reflux. Afterward, it was returned to room temperature, and the organic and aqueous layers were separated. Magnesium sulfate was added to this solution. The solution was concentrated by adding water and drying it. The resulting solution was then subjected to silica gel column chromatography. It was purified using [method / method]. The resulting solution was concentrated and dried. Then, hexane was added and recrystallized. The mixed solution containing the precipitated white solid was cooled with ice and then filtered. The resulting solid was vacuum dried at approximately 60°C. The mixture was dried to obtain 9.5 g of the target white solid in a yield of 63%. Step 1 Synthetic Ski The formula for "Mu" is shown below.

[0364] [ka]

[0365] <Step 2: N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H- Synthesis of fluoren-2-ylamine 10.5g of 9,9-dimethyl-9H-fluoren-2-amine (50ml) in a three-necked flask. ol), 4-cyclohexyl-1-bromobenzene 12.0g (50 mmol), sodium Add 14.4g (150mmol) of um-tert-butoxide and 250mL of xylene. After degassing under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred. Here, allyl palladium chloride dimer(II) (abbreviated as [(Allyl)P dCl]2) 183 mg (0.50 mmol), di-tert-butyl (1-methyl-2) ,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP(registered trademark))82 1 mg (2.0 mmol) was added, and the mixture was heated at 90°C for approximately 6 hours. The flask temperature was lowered to approximately 60°C, approximately 4 mL of water was added, and the precipitated solid was filtered off. Filtrate The solution was concentrated and purified by silica gel column chromatography. The liquid was concentrated to obtain a concentrated toluene solution. This toluene solution was dried under vacuum at approximately 60°C. Then, 17.3 g of the target product, a brownish oily substance, was obtained in a yield of 92%. Step 2 synthesis Chiem is shown in the following equation.

[0366] [ka]

[0367] <Step 3: N-[(3',5'-Ditter-butyl)-1,1'-Biphenyl- 4-yl]-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluore Synthesis of n-2-amine (abbreviation: mmtBuBichPAF) In a three-necked flask, add the 3',5'-diter-butyl-4-chloro- obtained in Step 1. 1,1'-biphenyl 3.2g (10.6 mmol), N-(4- obtained in step 2 Cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2yl)amide 3.9g (10.6 mmol), sodium tert-butoxide 3.1g (31. Add 8 mmol) and 53 mL of xylene, degas under reduced pressure, and then nitrify the flask. The mixture was substituted with an element. This mixture was heated and stirred to approximately 50°C. Here, di-palladium allyl chloride was added. Merged (II) (abbreviation: [(Allyl)PdCl]2) 39 mg (0.11 mmol), Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine Add 150 mg (0.42 mmol) of the abbreviated name: cBRIDP (registered trademark) to this mixture. It was heated at 120°C for about 3 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL was added, and the solid precipitated. The precipitated solid was filtered off. The filtrate was concentrated to obtain the solution. The solution was purified by silica gel column chromatography. The resulting solution was concentrated, and concentrated toll A toluene solution was obtained. Ethanol was added to this toluene solution, and it was concentrated under reduced pressure to obtain an ethanol suspension. The obtained solid was filtered at approximately 20°C, and the obtained solid was dried under reduced pressure at approximately 80°C. 5.8 g of the target white solid was obtained in a yield of 87%. The synthesis scheme for Step 3 is shown below. As shown.

[0368] [ka]

[0369] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 (H-NMR) The analysis results are shown below. This indicates that in this synthesis example, N-[(3',5'-ditter-shaly [-butyl)-1,1'-biphenyl-4-yl]-N-(4-cyclohexylphenyl) -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBuBichPAF) It was found that ) could be synthesized.

[0370] 1 H-NMR.δ(CDCl3):7.63(d,1H,J=7.5Hz),7.57( d,1H,J=8.0Hz),7.44-7.49(m,2H),7.37-7.42( m,4H),7.31(td,1H,J=7.5Hz,2.0Hz),7.23-7.2 7(m,2H),7.15-7.19(m,2H),7.08-7.14(m,4H), 7.05(dd,1H,J=8.0Hz,2.0Hz),2.43-2.53(brm, 1H),1.81-1.96(m,4H),1.75(d,1H,J=12.5Hz), 1.32-1.48(m,28H),1.20-1.31(brm,1H).

[0371] Next, 3.5 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 255°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 11.8 mL / min. The process was carried out. After sublimation purification, 3.1 g of a slightly yellowish-white solid was obtained with a recovery rate of 89%.

[0372] Furthermore, the refractive index of mmtBuBichPAF was measured using a spectroscopic ellipsometer (J.A.W. Measurements were taken using a Ram Japan M-2000U. The measurements involved measuring each layer on a quartz substrate. The material used was a film with a thickness of approximately 50 nm, deposited by vacuum deposition.

[0373] As a result, mmtBuBichPAF emits blue light in the blue emission region (455nm to 465nm). The refractive index is in the range of 1.50 to 1.75 throughout the entire region, and at 633 nm... The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. It was. [Examples]

[0374] This embodiment will describe in detail a light-emitting device using an organic compound according to one aspect of the present invention. The structural formulas of representative organic compounds used in this example are shown below.

[0375] [ka]

[0376] (Method for fabricating the light-emitting device 20) First, a 100 nm silver (Ag) film was deposited on a glass substrate to form a reflective electrode. After this, Indium tin oxide (ITSO) containing silicon oxide is deposited by sputtering, and the first An electrode 101 was formed. Its film thickness was set to 10 nm, and its electrode area to 2 mm × 2 mm. Ta.

[0377] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0378] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0379] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, By using a resistive heating deposition method, low refractive index organic compounds (low-n HTM) and electron activators are deposited. The septa material (OCHD-001) and HTM:O are used in a weight ratio of 1:0.1 (=low-n HTM:O A hole injection layer 111 was formed by co-depositing 10 nm of material to create CHD-001.

[0380] Furthermore, the above low-n HTM is the N-3',5'-jitter represented by the above structural formula (i). Shaributyl-1,1'-biphenyl-4-yl-N-1,1'-biphenyl-2-yl Lu-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBuBioFBi) ) was used.

[0381] Next, mmtBuBioFBi is vapor-deposited onto the hole injection layer 111 to a thickness of 120 nm. After forming the hole transport layer 112, the structure represented by the above structural formula (xiv) N-[4-(9 [H-carbazole-9-yl)phenyl]-N-[4-(4-dibenzofuranyl)phenyl ]-[1,1':4',1''-terphenyl]-4-amine (abbreviation: YGTPDBfB) An electron blocking layer was formed by depositing 10 nm of ) onto the material.

[0382] Next, the 2-(10-phenyl-9-anthracenyl)- represented by the above structural formula (xv) Benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA) and the above structural formula (x) represents 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl )-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation) :3,10PCA2Nbf(IV)-02) and in a weight ratio of 1:0.015 (=Bnf(I I) PhA: 3,10PCA2Nbf(IV)-02), co-evaporation to a film thickness of 25 nm. The luminescent layer 113 was then formed.

[0383] Subsequently, on the light-emitting layer 113, 2-[3'-(9,9-di, represented by the above structural formula (xvi) is applied. Methyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6- Diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) will be applied to a film thickness of 10 nm. A hole block layer was formed by depositing it onto sea urchin.

[0384] On the hole block layer, 2-[3-(2,6-dimethyl represented by the above structural formula (xvii) is formed. -3-pyridinyl)-5-(9-phenantrenyl)phenyl]-4,6-diphenyl- 1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) and the above structural formula (xi i) 8-quinolinolato-lithium (abbreviation: Liq) and a weight ratio of 1:1 (=m Pn-mDMePyPTzn:Liq) is co-deposited to a film thickness of 25 nm for electron transport. Layer 114 was formed.

[0385] After forming the electron transport layer 114, lithium fluoride (LiF) is deposited at a 1 nm thickness for electron injection. Layer 115 is formed, followed by silver (Ag) and magnesium (Mg) in a volume ratio of 10:1 (=A A second electrode 102 is formed by co-depositing 15 nm of material in the ratio g:Mg to create the light-emitting device 2. 0 was created. The second electrode 102 is translucent, and the light-emitting device 20 is the second electrode This is a top-emission type light-emitting device that extracts light from the electrode side. Also, a second electrode... On 102, the structure represented by the above structural formula (xviii) is 4,4',4''-(benzene-1 ,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) 70n The film is deposited to improve extraction efficiency.

[0386] (Method for fabricating the comparative light-emitting device 20) The comparison light-emitting device 20 uses mmtBuBioFBi in the light-emitting device 20 as described above. The formula (xiii) represents N-(1,1'-biphenyl-4-yl)-N-[4-(9 -phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H- Except for the change to ruolen-2-amine (abbreviation: PCBBiF), it is the same as light-emitting device 20. I made it.

[0387] The element structures of the above-mentioned light-emitting device 20 and comparative light-emitting device 20 are summarized in the table below.

[0388] [Table 8]

[0389] [Table 9]

[0390] Furthermore, the low-n HTM vapor-deposited film used for the hole injection layer and the hole transport layer, and the comparative material The ordinary refractive index n of the PCBBiF deposited film o , birefringence Δn and orientation order parameter S The table below shows the results.

[0391] [Table 10]

[0392] The above-mentioned light-emitting device and comparative light-emitting device were placed in a glove box under a nitrogen atmosphere. , the process of sealing the light-emitting device with a glass substrate so that it is not exposed to the atmosphere (using a sealing material) After applying it around the child, UV treatment and heat treatment at 80°C for 1 hour are performed during sealing, these We performed measurements on the initial characteristics of the optical device.

[0393] Figure 29 shows the luminance-current density characteristics of the light-emitting device 20 and the comparative light-emitting device 20. Voltage characteristics are shown in Figure 30, current efficiency-luminance characteristics in Figure 31, and current density-voltage characteristics in Figure 32. The blue index-luminance characteristics are shown in Figure 33, and the emission spectrum is shown in Figure 34. 1000 cd / m² optical device 2 Table 11 shows the main characteristics in the vicinity. Note that luminance, For measuring CIE chromaticity and emission spectra, a spectroradiometer (Topcon UR-UL) is used. Measurements were taken at room temperature using 1R). Note that the Blue Index (BI) refers to the current efficiency (c This value (d / A) is obtained by further dividing it by the y-chromaticity, and is one of the indicators that represent the emission characteristics of blue light. Blue light emission tends to have higher color purity as the y-chromaticity decreases. Color emission makes it possible to express a wide range of blue colors even with a small luminance component, and the color purity By using high blue light emission, the required brightness to represent blue decreases, thus reducing power consumption. A force reduction effect can be obtained. Therefore, BI takes into account y chromaticity, which is one of the indicators of blue purity. This is preferably used as a means to express the efficiency of blue light emission, and the higher the BI of a light-emitting device, the better the display. It can be said that it is highly efficient as a blue light-emitting device used in gameplay.

[0394] [Table 11]

[0395] As shown in Figures 29 to 34, the light-emitting device 20 of one aspect of the present invention is compared with the comparative light-emitting device 20. Using low refractive index organic compounds in the hole injection layer and hole transport layer while exhibiting equivalent driving voltage This has resulted in a significant improvement in blue index, luminous efficiency, and chromaticity. It can be seen that it is a light-emitting device. Therefore, the light-emitting device of one aspect of the present invention consumes It is a low-power light-emitting device.

[0396] Furthermore, the current density of the light-emitting device 20 and the comparative light-emitting device 20 is 50 mA / cm². 2 to Figure 35 shows a graph illustrating the change in brightness with respect to operating time. Furthermore, the light-emitting device 20, which is a light-emitting device according to one aspect of the present invention, is compared with the comparative light-emitting device 20. It was also found to be a light-emitting device with a comparatively better lifespan. [Examples]

[0397] In this embodiment, a light-emitting device and a comparative light-emitting device using an organic compound according to one aspect of the present invention are presented. Let's explain in detail. The structural formulas of representative organic compounds used in this example are shown below. .

[0398] [ka]

[0399] (Method for fabricating the light-emitting device 30) First, a 100 nm silver (Ag) film was deposited on a glass substrate to form a reflective electrode. After this, Indium tin oxide (ITSO) containing silicon oxide is deposited by sputtering, and the first An electrode 101 was formed. Its film thickness was set to 10 nm, and its electrode area to 2 mm × 2 mm. Ta.

[0400] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0401] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0402] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, By using a resistive heating deposition method, low refractive index organic compounds (low-n HTM) and electron activators are deposited. The septa material (OCHD-001) and HTM:O are used in a weight ratio of 1:0.1 (=low-n HTM:O A hole injection layer 111 was formed by co-depositing 10 nm of material to create CHD-001.

[0403] Furthermore, the above low-n HTM is the N-3',5'-jitter represented by the above structural formula (i). Shaributyl-1,1'-biphenyl-4-yl-N-1,1'-biphenyl-2-yl Lu-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBuBioFBi) ) was used.

[0404] Next, mmtBuBioFBi is vapor-deposited onto the hole injection layer 111 to a thickness of 125 nm. This forms a hole transport layer 112, and the structure is represented by the above structural formula (viii) N,N-bis[4 -(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: D An electron blocking layer was formed by depositing BfBB1TP to a thickness of 10 nm.

[0405] Next, the above structural formula (ix) represents 9-(1-naphthyl)-10-[4-(2-naphthyl] [Tyl)phenyl]anthracene (abbreviation: αN-βNPAnth) is represented by the above structural formula (x). 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-f [enylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10 PCA2Nbf(IV)-02) and αN-βNPAnth in a weight ratio of 1:0.015 (=αN-βNPAnth :3,10PCA2Nbf(IV)-02), co-deposited to a film thickness of 20 nm to produce light emission. Layer 113 was formed.

[0406] Subsequently, on the light-emitting layer 113, 6-(1,1'-biphenyl represented by the above structural formula (xix) Lu-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2 - Phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm) is deposited to a size of 10 nm. This forms a hole block layer, represented by the above structural formula (xvii) 2-[3-(2,6- Dimethyl-3-pyridinyl)-5-(9-phenantrenyl)phenyl]-4,6-diph Enyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) and the above structure 8-Quinolinolato-lithium (abbreviated as Liq), represented by formula (xii), in a weight ratio of 1: 1 (=mPn-mDMePyPTzn:Liq), co-deposited to a film thickness of 20 nm. An electron transport layer 114 was formed.

[0407] After forming the electron transport layer 114, lithium fluoride (LiF) is deposited at a 1 nm thickness for electron injection. Layer 115 is formed, and silver (Ag) and magnesium (Mg) are mixed in a volume ratio of 10:1 (=Ag:M g) A second electrode 102 is formed by co-depositing 15 nm of material to create a light-emitting device 30. It was accomplished. The second electrode 102 is translucent, and the light-emitting device 30 is on the second electrode side. It is a top-emission type light-emitting device that extracts light from the second electrode 102. Above is 4,4',4''-(benzene-1,3, represented by the above structural formula (xviii) 5-triyl(dibenzothiophene) (abbreviation: DBT3P-II) was deposited as a 70nm film. This improves the efficiency of extraction.

[0408] (Method for fabricating the light-emitting device 31) The light-emitting device 31 uses the mPn-mDMePyPTzn in the light-emitting device 30 as described above. The structural formula (xx) represents 2-{(3',5'-di-tert-butyl)-1,1'-butyl}. Phenyl-3-yl-4,6-diphenyl-1,3,5-triazine (abbreviation: mmtB) By changing umBPTzn to 6-methyl-8-k Aside from changing to lithium norolator (abbreviated as Li-6mq), the light-emitting device 30 was constructed in the same way. It was made.

[0409] (Method for fabricating the comparative light-emitting device 30) The comparative light-emitting device 30 uses the mmtBuBioFBi in the light-emitting device 31, as described above. The formula (xiii) represents N-(1,1'-biphenyl-4-yl)-N-[4-(9 -phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H- By changing to ruolen-2-amine (abbreviation: PCBBiF), the thickness of the hole transport layer was set to 115 nm. Other than that, it was fabricated in the same way as the light-emitting device 31.

[0410] (Method for fabricating the comparative light-emitting device 31) The comparative light-emitting device 31 uses mmtBuBioFBi in the light-emitting device 30 on the PCB. The device was fabricated in the same way as light-emitting device 30, except that BiF was used instead and the thickness of the hole transport layer was set to 115 nm. did.

[0411] The element structures of the above-mentioned light-emitting device and the comparative light-emitting device are summarized in the table below.

[0412] [Table 12]

[0413] [Table 13]

[0414] Furthermore, the low-n HTM vapor-deposited film used for the hole injection layer and the hole transport layer, and the comparative material The ordinary refractive index n of the PCBBiF deposited film o , birefringence Δn and orientation order parameter S The table below shows the results.

[0415] [Table 14]

[0416] The above-mentioned light-emitting device and comparative light-emitting device were placed in a glove box under a nitrogen atmosphere. , the process of sealing the light-emitting device with a glass substrate so that it is not exposed to the atmosphere (using a sealing material) After applying it around the child, UV treatment and heat treatment at 80°C for 1 hour are performed during sealing, these The initial characteristics of the optical device were measured. The glass substrate on which the light-emitting device was fabricated was also used. No special measures have been taken to improve extraction efficiency.

[0417] Light-emitting device 30, light-emitting device 31, comparison light-emitting device 30 and comparison light-emitting device 3 Figure 36 shows the luminance-current density characteristics, Figure 37 shows the luminance-voltage characteristics, and Figure 37 shows the current efficiency-luminance characteristics. Figure 38 shows the current density-voltage characteristics, Figure 39 shows the blue index-luminance characteristics, and Figure 40 shows the current density-voltage characteristics. The emission spectra of each light-emitting device are shown in Figure 41. 2 Nearby The main characteristics are shown in Table 15. Note that the measurements of luminance, CIE chromaticity, and emission spectrum were performed using the following method. Measurements were taken at room temperature using a spectroradiometer (Topcon UR-UL1R).

[0418] [Table 15]

[0419] As shown in Figures 36 to 41, a light-emitting device according to one aspect of the present invention uses a low refractive index organic compound as a hole By using it in the injection layer and hole transport layer, it is significantly more powerful than comparative light-emitting devices. —This indicates that the index has been improved and it is a light-emitting device with good luminous efficiency. Therefore, one embodiment of the present invention can be said to be a light-emitting device with low power consumption. Oh, mmtBumB used in the electron transport layer of light-emitting device 31 and comparative light-emitting device 30 PTzn and Li-6mq were used in the light-emitting device 30 and the comparative light-emitting device 31. It is a material with a lower refractive index compared to PCBBiF and Liq.

[0420] Furthermore, the above-mentioned light-emitting device 30, light-emitting device 31, comparison light-emitting device 30 and comparison light-emitting device The current density of device 31 is 50 mA / cm². 2 This represents the change in brightness with respect to the operating time. A rough sketch is shown in Figure 42. As shown in Figure 42, the light-emitting device according to one aspect of the present invention is It was also found that the optical device 30 and the light-emitting device 31 are light-emitting devices with a good lifespan. .

[0421] <Reference example> ≪Reference synthesis example 1≫ In this example, the N-(3,5-di) organic compound used as the low refractive index organic compound in Example 1 is used. Tert-butylphenyl)-N-(3',5',-di-tert-butyl-1,1' -biphenyl-4-yl)-9,9,-dimethyl-9H-fluoren-2-amine (abbreviation) This explains the synthesis method for :mmtBuBimmtBuPAF). The structure of tBuPAF is shown below.

[0422] [ka]

[0423] <Step 1: 3',5'-Diter-butyl-4-chloro-1,1'-biphenyl Synthesis of > The synthesis was carried out in the same manner as in step 1 of synthesis example 3 in Example 3.

[0424] <Step 2: N-(3',5'-Ditter-butyl-1,1'-biphenyl-4- Synthesis of (yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine 2.8g (13.5ml) of 9,9-dimethyl-9H-fluoren-2-amine in a three-necked flask. mol), 3',5'-ditter-butyl-4-chloro-1 obtained in step 1, 1'-Biphenyl 6.1g (20.3 mmol), sodium tert-butoxide 5 Add 0.8g (60.8mmol) and 70mL of xylene, degass under reduced pressure, and then... The inside of the lasco was purged with nitrogen. This mixture was heated and stirred to approximately 50°C. Here, allyl chloride was added. Palladium dimer(II) (abbreviation: [(Allyl)PdCl]2) 100 mg (0.2 7 mmol), di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl ) Add 381 mg (1.08 mmol) of phosphine (abbreviation: cBRIDP(registered trademark)) It was heated at 120°C for about 3 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was collected by silica gel column chromatography. It was purified by chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and the mixture was concentrated under reduced pressure to obtain an ethanol suspension. At approximately 20°C The precipitate is filtered, and the resulting solid is dried under reduced pressure at approximately 80°C to obtain a brownish oily substance containing N- (3',5'-Diter-butyl-1,1'-biphenyl-4-yl)-N-(9, 2.9 g of 9-dimethyl-9H-fluoren-2-yl)amine was obtained in a yield of 46%. The synthesis scheme for step 2 is shown in the following equation.

[0425] [ka]

[0426] <Step 3: N-(3,5-di-tert-butylphenyl)-N-(3',5'-di Tert-butyl-1,1'-biphenyl-4-yl)-9,9-dimethyl-9H- Synthesis of ruolen-2-amine (abbreviation: mmtBuBimmtBuPAF) In a three-necked flask, the N-(3',5'-ditter-butyl-1, obtained in step 2 1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl) ) 2.7g (5.7mmol) amine, 3,5-diter-butyl-1-bromobene Zen 1.5g (5.7 mmol), sodium tert-butoxide 1.6g (17. Add 0 mmol) and 30 mL of xylene, degas under reduced pressure, and then nitrify the flask. The mixture was substituted with an element. This mixture was heated and stirred to approximately 50°C. Here, di-palladium allyl chloride was added. Merged (II) (abbreviation: [(Allyl)PdCl]2) 21 mg (0.057 mmol) Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine Add 73 mg (0.208 mmol) of (abbreviation: cBRIDP(registered trademark)) and heat at 120°C. It was heated for about 7 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL of water was added. The precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was subjected to silica gel column chromatography. It was purified using a filtration system. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the liquid and concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at approximately 20°C. The mixture was then dried under reduced pressure at approximately 80°C to obtain 3.6 g of the target white solid, yielding a yield of 3.6 g. It was obtained with 95% accuracy. The synthesis scheme for Step 3 is shown in the following equation.

[0427] [ka]

[0428] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 ( 1 Analysis results by H-NMR The results are shown below. As a result, in this synthesis example, N-(3,5-ditermylbutylf (phenyl)-N-(3',5'-Diter-butyl-1,1'-biphenyl-4-yl) )-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBuBimmtB) It was found that uPAF could be synthesized.

[0429] 1 H-NMR.δ(CDCl3):7.64(d,1H,J=7.5Hz),7.57( d,1H,J=8.0Hz),7.48(d,2H,J=8.0Hz),7.43(m, 2H),7.39(m,2H),7.31(td,1H,J=6.0Hz,1.5Hz) ,7.15-7.25(m,4H),6.97-7.02(m,4H),1.42(s, 6H), 1.38(s,18H), 1.25(s,18H).

[0430] Next, 3.2 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 210°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 19.3 mL / min. The process was carried out. After sublimation purification, 3.0 g of a slightly yellowish-white solid was obtained with a recovery rate of 94%.

[0431] Furthermore, the refractive index of mmtBuBimmtBuPAF was measured using a spectroscopic ellipsometer (J.A. Measurements were taken using a Woolam Japan M-2000U. The film used consisted of materials for each layer deposited by vacuum deposition, with a thickness of approximately 50 nm.

[0432] As a result, mmtBuBimmtBuPAF is in the blue emission region (455nm to 465nm). (The following) The entire region has a normal refractive index in the range of 1.50 to 1.75, and at 633 nm The refractive index in ordinary light is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. That's what I found out.

[0433] ≪Reference synthesis example 2≫ In this example, the N-(3,3'', which was used as the low refractive index organic compound in Example 1, is used. 5,5''-Tetra-t-butyl-1,1':3',1''-Terphenyl-5'-yl )-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene-2- This document describes the synthesis method of the amine (abbreviation: mmtBumTPchPAF). The structure of mTPchPAF is shown below.

[0434] [ka]

[0435] <Step 1: 3,3'',5,5''-Tetra-t-butyl-5'-chloro-1,1' Synthesis of 3',1''-terphenyl Dissolve 1,3-dibromo-5-chlorobenzene in a three-necked flask. 1.66 g (6.14 mmol) ), 2-(3,5-di-t-butylphenyl)-4,4,5,5-tetramethyl-1,3 2-Dioxaborolane 4.27g (13.5 mmol), Tris(2-methylphenyl )Phosphine (abbreviation: P(o-tolyl)3) 187 mg (0.614 mmol), 2 Add 13.5 mL of potassium carbonate aqueous solution, 20 mL of toluene, and 10 mL of ethanol. The mixture was degassed by stirring under reduced pressure and then purged with nitrogen. Palladium acetate was added to this mixture. II) Add 27.5 mg (0.122 mmol) and stir at 80°C for approximately 4 hours under a nitrogen stream. After stirring, water was added to the mixture to separate it into an organic layer and an aqueous layer. The aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated saline solution, and then treated with magnesium sulfate. It was dried. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a yellow oily substance. The oily substance was purified by silica gel column chromatography. The resulting fraction was The solution was concentrated to obtain the target product, a white solid, in a yield of 2.98 g and 99%. Synthesis of Step 1 The scheme is shown in the following equation.

[0436] [ka]

[0437] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 (H-NMR) The analysis results are shown below. As a result, in step 1, the organic compound, 3,3'',5, 5''-tetra-t-butyl-5'-chloro-1,1':3',1''-terphenyl It was confirmed that the synthesis was successful.

[0438] 1 H-NMR(300MHz,CDCl3):δ=7.63-7.64(m,1H),7 .52-7.47(m,4H),7.44-7.40(m,4H),1.38(s,36 H).

[0439] <Step 2: N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H- Synthesis of fluoren-2-ylamine The synthesis was carried out in the same manner as in step 2 of synthesis example 3 of Example 3.

[0440] <Step 3: N-(3,3'',5,5''-tetra-t-butyl-1,1':3', 1''-Terphenyl-5'-yl)-N-(4-cyclohexylphenyl)-9,9- Synthesis of dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPchPAF) > In a three-necked flask, place the N-(4-cyclohexylphenyl)-N-(9, obtained in step 2) into a three-necked flask. 9-dimethyl-9H-fluoren-2yl)amine 2.69g (7.32 mmol), 3,3'',5,5''-tetra-t-butyl-5'-chloro-1 obtained in step 1 1':3',1''-Terphenyl 2.98g (6.09mmol), di-tert- Tyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRID) P(registered trademark)) 0.103g (0.292 mmol), sodium-tert-butoxyl Add 1.76 g (18.3 mmol) of cytoside and 30 mL of xylene, and stir under reduced pressure. After degassing, the mixture was purged with nitrogen. Allyl palladium chloride dimer(II) was added to this mixture. Abbreviation: [(Allyl)PdCl]2) 26.7 mg (0.0730 mmol) was added. The mixture was stirred at 120°C for approximately 10 hours under a nitrogen atmosphere. After stirring, water was added to the mixture to separate the organic layer from the water. The mixture was separated into layers. The resulting aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined. After washing with water and saturated saline solution, the mixture was dried with magnesium sulfate. This mixture was then filtered by natural filtration. The filtrate was filtered and concentrated to obtain a black oily substance. This oily substance was then subjected to silica gel column chromatography. It was purified by a fine. The resulting fraction was concentrated to obtain a pale yellow oily substance. The substance was purified by high-performance liquid column chromatography (eluent: chloroform). The fraction was concentrated to obtain a white solid. Ethanol was added to this solid and ultrasound was applied. After irradiation, the solid was collected by suction filtration, yielding 3.36 g of the target white solid. The yield was 67%. The synthesis scheme for Step 3 is shown in the following equation.

[0441] [ka]

[0442] The obtained white solid (3.36 g) was purified by sublimation using the train sublimation method. The manufacturing process involved producing a white solid at 240°C under conditions of a pressure of 5.0 Pa and an argon flow rate of 10 mL / min. The process was carried out by heating. After sublimation purification, a colorless, transparent, glassy solid was obtained with a yield of 1.75 g and a recovery rate of 52%. I got it.

[0443] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 (H-NMR) The analysis results are shown below. This indicates that in this synthesis example, the organic compound, N-(3,3'', 5,5''-Tetra-t-butyl-1,1':3',1''-Terphenyl-5'-yl )-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene-2- It was found that the amine (abbreviated as mmtBumTPchPAF) could be synthesized.

[0444] 1 H-NMR(300MHz, CDCl3):δ=7.63(d,J=6.6Hz,1H ),7.58(d,J=8.1Hz,1H),7.42-7.37(m,4H),7.3 6-7.09(m,14H),2.55-2.39(m,1H),1.98-1.20( m,51H).

[0445] Furthermore, the refractive index of mmtBumTPchPAF is measured using a spectroscopic ellipsometer (J.A.W. Measurements were taken using a M-2000U (manufactured by Ram Japan). For the measurement, each layer on a quartz substrate was measured. A film of approximately 50 nm in thickness was used, formed by vacuum deposition of the material.

[0446] As a result, mmtBumTPchPAF is in the blue emission region (455nm to 465nm). ) The ordinary refractive index is in the range of 1.50 to 1.75 throughout the entire region, and at 633 nm The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. Understood.

[0447] ≪Reference synthesis example 3≫ In this example, the N-(1,1'-) organic compound used as the low refractive index in Example 1 was used. Biphenyl-2-yl)-N-(3,3'',5',5''-tetra-tert-butyl -1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl-9H-full This document describes the synthesis method of olen-2-amine (abbreviation: mmtBumTPoFBi-02). The structure of mmtBumTPoFBi-02 is shown below.

[0448] [ka]

[0449] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > 37.2g of 1,3-dibromo-5-tert-butylbenzene (128ml) in a three-necked flask. 20.0 g (85 mmol) of 3,5-di-tert-butylphenylboronic acid Potassium carbonate 35.0g (255 mmol), toluene 570 mL, ethanol 170 Add mL of tap water and 130 mL of tap water, degas under reduced pressure, then purge the flask with nitrogen. Palladium acetate 382 mg (1.7 mmol), Triphenylphosphine 901 mg (3 (0.4 mmol) was added and heated at 40°C for approximately 5 hours. Afterwards, it was returned to room temperature and the organic layer and water were separated. The layers were separated. Magnesium sulfate was added to this organic layer to remove water and concentrate it. The solution was purified by silica gel column chromatography, and the target product, a colorless oily substance, was obtained (21). 5g was obtained with a yield of 63%. The synthesis scheme for Step 1 is shown in the following equation.

[0450] [ka]

[0451] <Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The 3-bromo-3',5,5'-tert-butylbi obtained in Step 1 is placed in a three-necked flask. Phenyl 15.0g (38 mmol), 4,4,4',4',5,5,5',5'-octane Tamethyl-2,2'-bi-1,3,2-dioxaborolane 10.5g (41 mmol), Potassium acetate 11.0g (113 mmol), N,N-dimethylformamide 125mL After adding [1,1'-bis(diphthol) and degassing under reduced pressure, the flask is purged with nitrogen and [1,1'-bis(diphthol) [Phenylphosphino)ferrocene]dichloropalladium(II) (abbreviation: Pd(dppf)) Add 1.5g (1.9 mmol) of Cl2 and heat at 100°C for approximately 3 hours. The solution was returned to room temperature, and the organic and aqueous layers were separated and extracted with ethyl acetate. This extract was then mixed with sulfuric acid. Gnesium was added to remove water and concentrate the mixture. The resulting toluene solution was then dissolved in silica gel. The solution obtained by purification using column chromatography was concentrated to obtain a concentrated toluene solution. Ethanol was added to this toluene solution, and the solution was concentrated under reduced pressure to obtain an ethanol suspension. (Approximately 20°C) The precipitate is filtered, and the resulting solid is dried under reduced pressure at approximately 80°C to obtain the target white solid. 13.6 g was obtained in 81% yield. The Step 2 synthesis scheme is shown in the following equation.

[0452] [ka]

[0453] <Step 3: 3-bromo-3'', 5,5',5''-tetra-tert-butyl-1 Synthesis of ,1':3',1''-terphenyl In a three-necked flask, add 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5.0 g (11.1 mmol), 1,3-dibromo-5-tert-butylbenzene 4.8 g ( 16.7 mmol), potassium carbonate 4.6 g (33.3 mmol), toluene 56 mL, Add 22 mL of ethanol and 17 mL of tap water, degass under reduced pressure, and then... Nitrogen purged, palladium acetate 50 mg (0.22 mmol), triphenylphosphine 1 16 mg (0.44 mmol) was added and heated at 80°C for approximately 10 hours. Afterwards, it was left at room temperature. The solution was returned to the liquid and the organic and aqueous layers were separated. Magnesium sulfate was added to this solution to remove water and concentrate it. The obtained hexane solution was purified by silica gel column chromatography, and the target product was obtained. A white solid was obtained in 3.0 g with a yield of 51.0%. Also, 3-bromo-3'', from step 3. 5,5',5''-Tetra-tert-butyl-1,1':3',1''-Terphenyl The synthesis scheme is shown in the following equation.

[0454] [ka]

[0455] <Step 4: Synthesis of mmtBumTPoFBi-02> The 3-bromo-3'',5,5',5''-tetra- obtained in step 3 is placed in a three-necked flask. tert-butyl-1,1':3',1''-terphenyl 5.8g (10.9 mmol) ), N-(1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H -Fluoren-2-amine 3.9g (10.9 mmol), sodium-tert-butone Add 3.1g (32.7mmol) of oxide and 55mL of toluene, and degas under reduced pressure. Afterward, the flask was purged with nitrogen, and bis(dibenzylideneacetone)palladium(0)64 mg (0.11 mmol), tri-tert-butylphosphine 132 mg (0.65 mg) (mol) was added and heated at 80°C for approximately 2 hours. After that, the flask temperature was reduced to approximately 60°C. Return the sample to the container, add approximately 1 mL of water, filter off the precipitated solid, and wash with toluene. The filtrate was concentrated, The resulting toluene solution was purified by silica gel column chromatography. The solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to this toluene solution, and the solution was concentrated under reduced pressure. A condensed ethanol suspension was obtained. The precipitate was filtered at approximately 20°C, and the resulting solid was heated at approximately 80°C. The product was dried under reduced pressure to obtain 8.1 g of the target white solid in a yield of 91%. mmtBumTP The synthesis scheme for oFBi-02 is shown in the following equation.

[0456] [ka]

[0457] Furthermore, nuclear magnetic resonance spectroscopy of the white powder obtained above ( 1 Analysis results by 1H-NMR This is shown below. From this, it can be concluded that in this synthesis example, N-(1,1'-biphenyl-2-yl)-N -(3,3'',5',5''-Tetra-tert-butyl-1,1':3',1''- Terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: It was confirmed that mmtBumTPoFBi-02) could be synthesized.

[0458] 1 H-NMR.δ(CDCl3):7.56(d,1H,J=7.4Hz),7.50( dd,1H,J=1.7Hz),7.33-7.46(m,11H),7.27-7.2 9(m,2H),7.22(dd,1H,J=2.3Hz),7.15(d,1H,J= 6.9Hz),6.98-7.07(m,7H),6.93(s,1H),6.84(d ,1H,J=6.3Hz),1.38(s,9H),1.37(s,18H),1.31 (s,6H), 1.20(s,9H).

[0459] Furthermore, the refractive index of mmtBumTPoFBi-02 was measured using a spectroscopic ellipsometer (J.A. Measurements were taken using a Woolam Japan M-2000U. The film used consisted of materials for each layer deposited by vacuum deposition, with a thickness of approximately 50 nm.

[0460] As a result, mmtBumTPoFBi-02 emits blue light in the blue light emission region (455nm to 465nm). (The following) Throughout the entire region, the refractive index is between 1.69 and 1.70, and within the range of 1.50 to 1.75. Furthermore, the ordinary refractive index at 633 nm is 1.64, within the range of 1.45 to 1.70. It was found to be a material with a low refractive index.

[0461] ≪Reference synthesis example 4≫ In this example, the N-(4-cyclo) organic compound used as the low refractive index organic compound in Example 1 is used. Hexylphenyl)-N-(3,3'',5',5''-tetra-tert-butyl-1 ,1':3',1''-terphenyl-5-yl)-9,9-dimethyl-9H-fluore This document explains the synthesis method for n-2-amine (abbreviation: mmtBumTPchPAF-02). The structure of mmtBumTPchPAF-02 is shown below.

[0462] [ka]

[0463] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > The synthesis was performed in the same manner as in Step 1 of Reference Synthesis Example 3.

[0464] <Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The synthesis was performed in the same manner as in step 2 of reference synthesis example 3.

[0465] <Step 3: 3-bromo-3'', 5,5',5''-tetra-tert-butyl-1 Synthesis of ,1':3',1''-terphenyl The synthesis was performed in the same manner as in step 3 of Reference Synthesis Example 3.

[0466] <Step 4: Synthesis of mmtBumTPchPAF-02> The 3-bromo-3'',5,5',5''-tetra- obtained in step 3 is placed in a three-necked flask. tert-butyl-1,1':3',1''-terphenyl 3.0g (5.6 mmol) , N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluorene- 2.1g (5.6 mmol) of 2-ylamine, 1.6g of sodium tert-butoxide g (16.9 mmol), 28 mL of toluene, degass under reduced pressure, then fras The inside is purged with nitrogen, and bis(dibenzylideneacetone)palladium(0) (abbreviated as Pd(db) a)2) 65 mg (0.11 mmol), 2-dicyclohexylphosphino-2',6' - Dimethoxybiphenyl (abbreviation: S-Phos) 139 mg (0.34 mmol) was added. It was heated at 80°C for approximately 2 hours. After that, the flask temperature was returned to approximately 60°C, and approximately 1 ml of water was added. L was added, the precipitated solid was filtered off and washed with toluene. The filtrate was concentrated and the obtained toluene was collected. The solution was purified by silica gel column chromatography. The resulting solution was concentrated and concentrated A toluene solution was obtained. Ethanol was added to this toluene solution and concentrated under reduced pressure to obtain ethanol. A suspension was obtained. The precipitate was filtered at approximately 20°C, and the resulting solid was dried under reduced pressure at approximately 80°C. 3.7 g of the target white solid was obtained in 80% yield. mmtBumTPchPAF-0 The synthesis scheme for 2 is shown in the following equation.

[0467] [ka]

[0468] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained from the above ( 1 Analysis results by 1H-NMR This is shown below. From this, it follows that in this synthesis example, N-(4-cyclohexylphenyl)-N- (3,3'',5',5''-tetra-tert-butyl-1,1':3',1''-ta -phenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: m It was confirmed that mtBumTPchPAF-02) could be synthesized.

[0469] 1 H-NMR.δ(CDCl3):7.62(d,1H,J=7.5Hz),7.56( d,1H,J=8.0Hz),7.50(dd,1H,J=1.7Hz),7.46-7 .47(m,2H),7.43(dd,1H,J=1.7Hz),7.37-7.39( m,3H),7.29-7.32(m,2H),7.23-7.25(m,2H),7. 20(dd,1H,J=1.7Hz),7.09-7.14(m,5H),7.05(d d,1H,J=2.3Hz),2.46(brm,1H),1.83-1.88(m,4 H),1.73-1.75(brm,1H),1.42(s,6H),1.38(s,9 H), 1.36 (s, 18H), 1.29 (s, 9H)

[0470] Next, 3.5 g of the obtained white solid was subjected to the train sublimation method at a pressure of 4.0 Pa. The solution was purified by sublimation under conditions of argon flow rate of 15.0 mL / min and temperature of 265°C. After sublimation purification, the solution was finely ground. A yellowish-white solid of 3.1 g was obtained with a recovery rate of 89%.

[0471] Furthermore, the refractive index of mmtBumTPchPAF-02 was measured using a spectroscopic ellipsometer (J.E.). Measurements were taken using a Woolam Japan M-2000U. The film used consisted of layers of material deposited by vacuum deposition, with each layer having a thickness of approximately 50 nm.

[0472] As a result, mmtBumTPchPAF-02 emits blue light (455nm and above, 465nm and above). (Below m) The entire range has a normal refractive index of 1.67 to 1.68, within the range of 1.50 to 1.75. Yes, and the ordinary refractive index at 633 nm is also 1.62, within the range of 1.45 to 1.70. It was found to be a material with a low refractive index, located within the enclosure. [Explanation of Symbols]

[0473] 101 Anode 102 Cathode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 P type layer 118 Electron relay layer 119 Electron injection buffer layer 400 circuit boards 401 Anode 403 EL layer 404 Cathode 405 sealant 406 Sealant 407 Sealing substrate 412 pads 420 IC chips 601 Drive circuit section (source line drive circuit) 602 pixel section 603 Drive circuit section (gate wire drive circuit) 604 Sealing substrate 605 Sealant 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 element substrate 611 Switching FET 612 Current-Controlled FET 613 Anode 614 Insulators 616 EL layer 617 Cathode 618 Light-emitting devices 951 circuit board 952 Electrode 953 Insulating layer 954 Partition layer 955 EL layer 956 Electrode 1001 circuit board 1002 Underlying insulating film 1003 Gate Insulator 10:06 Guard Station 1007 🙏 1008 Gate 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode 1024W anode 1024R Anode 1024G anode 1024B Anode 1025 Bulkhead 1028 EL layer 1029 Cathode 1031 Sealing substrate 1032 Sealant 1033 Transparent base material 1034R Red colored layer 1034G Green colored layer 1034B Blue colored layer 1035 Black Matrix 1036 Overcoat layer 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Peripheral area 2001 cabinet 2002 light source 2100 Robots 2110 Arithmetic equipment 2101 Illuminance Sensor 2102 Microphone 2103 Top camera 2104 Speaker 2105 Display 2106 Lower Camera 2107 Obstacle Sensor 2108 Moving mechanism 3001 Lighting device 5000 cabinets 5001 Display section 5002 Display section 5003 Speaker 5004 LED Lamp 5005 Operation Keys 5006 Connection terminal 5007 Sensor 5008 Microphone 5012 Support part 5013 Earphones 5100 Cleaning Robot 5101 Display 5102 Camera 5103 Brush 5104 Operation Buttons 5150 Mobile Information Terminal 5151 enclosure 5152 Display area 5153 Bent section 5120 Garbage 5200 display area 5201 Display area 5202 Display area 5203 Display area 7101 enclosure 7103 Display section 7105 Stand 7107 Display section 7109 Operation Keys 7110 Remote Control Unit 7201 Main Unit 7202 enclosure 7203 Display section 7204 Keyboard 7205 External connection port 7206 Pointing device 7210 Display section 7401 enclosure 7402 Display section 7403 Operation Buttons 7404 External connection port 7405 Speaker 7406 Microphone 7400 mobile phones 9310 Mobile Information Terminal 9311 Display Panel 9313 Hinge 9315 enclosure

Claims

1. Anode and, Cathode and, Between the anode and the cathode, there is a light-emitting layer and a hole transport region, The hole transport region is located between the anode and the light-emitting layer. The hole transport region contains an organic compound having an arylamine structure. The organic compound has a paraphotometric refractive index of 1.50 or more and 1.75 or less for the deposited film with respect to light at a wavelength of 458 nm. The organic compound is a light-emitting device in which the orientation order parameter of the deposited film with respect to light at the wavelength of the absorption peak located at the longest wavelength in the absorption spectrum is between -0.07 and 0.

00.

2. In claim 1, A light-emitting device wherein at least one nitrogen atom of the amine in the arylamine structure of the organic compound is bonded to a group containing a parabiphenyl structure.

3. In claim 1 or claim 2, A light-emitting device in which the organic compound is an organic compound in which a hydrogen atom is bonded to the meta carbon in one or more aniline structures contained in the arylamine structure.

4. In any one of claims 1 to 3, A light-emitting device in which the organic compound is an organic compound in which one or more benzene rings in the arylamine structure contained in the arylamine structure each independently have substituents at the para position.

5. In claim 4, A light-emitting device in which the organic compound is an organic compound in which one of the benzene rings in the multiple aniline structures contained in the arylamine structure has a cyclohexyl group at the para position.

6. In claim 4, A light-emitting device in which the organic compound is an organic compound in which one of the benzene rings in the multiple aniline structures contained in the arylamine structure has a phenyl group in the ortho position.

7. In any one of claims 1 to 6, A light-emitting device wherein the aforementioned organic compound is an organic compound having a triarylamine structure.

8. In any one of claims 1 to 7, A light-emitting device in which the organic compound is an organic compound in which a fluorenyl group is bonded to the nitrogen of the amine in the arylamine structure.

9. In any one of claims 1 to 8, A light-emitting device wherein the aforementioned organic compound is a monoamine compound.

10. In any one of claims 1 to 9, The hole transport region comprises a hole injection layer and a hole transport layer, The hole injection layer is located between the anode and the hole transport layer. A light-emitting device in which the aforementioned organic compound is contained in the hole transport layer.

11. In any one of claims 1 to 9, The hole transport region comprises a hole injection layer and a hole transport layer, The hole injection layer is located between the anode and the hole transport layer. A light-emitting device in which the organic compound is contained in both the hole injection layer and the hole transport layer.

12. In claim 11, A light-emitting device wherein the hole injection layer contains a substance that exhibits acceptability to the organic compound.

13. In claim 12, A light-emitting device in which the substance exhibiting the aforementioned acceptability is an organic compound.

14. A light-emitting device according to any one of claims 1 to 13, An electronic device having at least one of a sensor, an operating button, a speaker, and a microphone.

15. A light-emitting device according to any one of claims 1 to 13, A light-emitting device comprising at least one of a transistor and a substrate.

16. A lighting device comprising a light-emitting device according to any one of claims 1 to 13, and a housing.

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