Arylamine compounds, materials for hole transport layer and hole injection layer, light emitting devices and apparatuses, electronic devices, and lighting apparatuses

Abstract

Provided are a novel arylamine compound having a low refractive index, a material for a hole transport layer and a hole injection layer, a light-emitting device and apparatus, an electronic device, and an illumination apparatus. The present invention provides an arylamine compound having at least one aromatic group, the aromatic group having a first benzene ring, a second benzene ring, and a third benzene ring, and at least three alkyl groups, the first benzene ring to the third benzene ring being directly bonded in order, the first benzene ring being bonded to a nitrogen of an amine, the first benzene ring can further have a substituted or unsubstituted phenyl group, the second benzene ring or the third benzene ring can further have an alkylated phenyl group, two or more of the first benzene ring to the third benzene ring are independently bonded at positions 1 and 3, respectively, to other benzene rings, benzene rings of the alkylated phenyl groups, any of the at least three alkyl groups, or the nitrogen of the amine.

Description

TECHNICAL FIELD

[0001] One embodiment of the present application relates to an organic compound, a light-emitting element, a light-emitting device, a display module, a lighting module, a display device, a light-emitting device, an electronic device, a lighting device, and an electronic appliance. Note that one embodiment of the present application is not limited to the above technical field. The technical field of one embodiment of the present application disclosed in this specification and the like relates to an object, a method, or a manufacturing method. In addition, one embodiment of the present application relates to a process, a machine, manufacture, or a composition of matter. Thus, more specifically, examples of the technical field of one embodiment of the present application disclosed in this specification include a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, a power storage device, a storage device, an imaging device, and a method for driving them or a method for manufacturing them. BACKGROUND

[0002] In recent years, practical use of a light-emitting device (organic EL device) using an organic compound and utilizing electroluminescence (EL) has been actively developed. In a basic structure of such a light-emitting device, an organic compound layer (EL layer) containing a light-emitting material is interposed between a pair of electrodes. By application of voltage to this element, carriers (holes and electrons) are injected, and light emission from a light-emitting material can be obtained using recombination energy of the carriers.

[0003] Since such a light-emitting device is a self-luminous light-emitting device, it has advantages such as higher visibility than liquid crystals, and does not need a backlight when used for a pixel of a display. Thus, the light-emitting device is suitable for a flat panel display element. Furthermore, a display using such a light-emitting device can be manufactured to be thin and light, which is a great advantage. Furthermore, very high-speed response is one of the features of the light-emitting element.

[0004] In addition, since the light-emitting layer of such a light-emitting device can be formed continuously in two dimensions, surface emission can be obtained. Since this is a feature that is difficult to obtain in a point light source typified by an incandescent lamp or an LED or a linear light source typified by a fluorescent lamp, the above light-emitting element is also useful as a surface light source applicable to illumination or the like.

[0005] As described above, although a display or a lighting device using a light-emitting device is suitable for a variety of electronic devices, research and development of a light-emitting device having more favorable characteristics are increasingly active.

[0006] Low light extraction efficiency is a common problem in organic EL devices. In particular, attenuation caused by reflection due to differences in refractive index between adjacent layers is a major factor in device efficiency degradation. To mitigate this effect, a structure has been proposed in which a layer composed of a low-refractive-index material is formed within the EL layer (see, for example, Non-Patent Document 1).

[0007] Compared to light-emitting devices with existing structures, light-emitting devices with this structure can achieve higher light extraction efficiency and external quantum efficiency. However, it is difficult to form such a low-refractive-index layer within the EL layer without adversely affecting other important properties of the light-emitting device. This is because a low refractive index is traded off against high carrier transport properties and reliability when used in light-emitting devices. This is because organic compounds often derive their carrier transport properties and reliability from the presence of unsaturated bonds, and organic compounds with many unsaturated bonds tend to have a high refractive index.

[0008] [Patent Document 1] Japanese Patent Application Publication No. 11-282181

[0009] [Patent Document 2] Japanese Patent Application Publication No. 2009-91304

[0010] [Patent Document 3] U.S. Patent Application Publication No. 2010 / 104969

[0011] [Non-Patent Document 1] Jaeho Lee and 12 others, “Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes,” Nature Communications, June 2, 2016, DOI: 10.1038 / ncomms11791 Summary of the Invention

[0012] An object of one embodiment of the present invention is to provide a novel hole transport layer material. An object of one embodiment of the present invention is to provide a hole transport layer material having a low refractive index. An object of one embodiment of the present invention is to provide a hole transport layer material having a low refractive index and sufficient carrier transport properties. An object of one embodiment of the present invention is to provide a hole transport layer material having a low refractive index and sufficient hole transport properties.

[0013] One object of one embodiment of the present invention is to provide a novel arylamine compound. Another object of one embodiment of the present invention is to provide a novel arylamine compound having sufficient hole-transporting properties. Another object of one embodiment of the present invention is to provide an arylamine compound having a low refractive index. Another object of one embodiment of the present invention is to provide an arylamine compound having a low refractive index and sufficient hole-transporting properties.

[0014] One object of one embodiment of the present invention is to provide a light-emitting device with high luminous efficiency. Another object of one embodiment of the present invention is to provide a light-emitting device, a light-emitting apparatus, an electronic device, a display device, and an electronic device with low power consumption.

[0015] Note that the inclusion of these objectives does not preclude the existence of other objectives. One embodiment of the present invention does not necessarily achieve all of the above objectives. Note that objectives other than those listed above can be understood and extracted from the description of the specification, drawings, claims, etc.

[0016] The present invention only needs to achieve any one of the above-mentioned objects.

[0017] One embodiment of the present invention is an arylamine compound having at least one aromatic group, wherein the aromatic group has a first benzene ring, a second benzene ring, and a third benzene ring and at least three alkyl groups, the first benzene ring, the second benzene ring, and the third benzene ring are directly bonded in sequence, the first benzene ring is bonded to the nitrogen of the amine in the arylamine compound, the first benzene ring may further have a substituted or unsubstituted phenyl group, the second benzene ring or the third benzene ring may further have an alkylated phenyl group, and two or more of the first benzene ring, the second benzene ring, and the third benzene ring are independently bonded to other benzene rings, the benzene ring of the alkylated phenyl group, any of the at least three alkyl groups, or the nitrogen of the amine at the 1-position and 3-position, respectively.

[0018] Another embodiment of the present invention is an arylamine compound, wherein, in the above structure, the second benzene ring or the third benzene ring has an alkylated phenyl group.

[0019] Another embodiment of the present invention is an arylamine compound in the above structure, wherein the first benzene ring has an unsubstituted phenyl group.

[0020] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, all of the first benzene ring, the second benzene ring, the third benzene ring, and the benzene ring of the alkylated phenyl group are independently bonded at the 1-position and 3-position to other benzene rings, any one of the at least three alkyl groups, or the nitrogen of the amine.

[0021] Another embodiment of the present invention is an aromatic amine compound, wherein in the above structure, all of the first benzene ring, the second benzene ring, the third benzene ring, and the benzene ring of the alkylated phenyl group are independently bonded to other benzene rings, any one of the at least three alkyl groups, or the nitrogen of the amine at the 1-position, 3-position, and 5-position, respectively, and are unsubstituted at other bonding positions.

[0022] Another embodiment of the present invention is an arylamine compound having the above structure, wherein the arylamine compound further has a second aromatic group, and the second aromatic group is a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring skeleton having three or fewer rings.

[0023] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the second aromatic group is a substituted or unsubstituted fused ring skeleton of three or less rings, and the number of carbon atoms forming the fused ring skeleton is 6 to 13.

[0024] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the fused ring skeleton is a fluorene ring.

[0025] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the second aromatic group is a dimethylfluorenyl group.

[0026] Another embodiment of the present invention is an arylamine compound having the above structure, wherein the arylamine compound further has a third aromatic group, and the third aromatic group has one to three substituted or unsubstituted benzene rings.

[0027] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the alkyl group is a chain alkyl group having 2 to 5 carbon atoms.

[0028] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the alkyl group is a branched chain alkyl group having 3 to 5 carbon atoms.

[0029] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the alkyl group is a tert-butyl group.

[0030] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the arylamine compound is a triarylamine compound.

[0031] Another embodiment of the present invention is an arylamine compound in the above structure, wherein a layer formed of the arylamine compound has an ordinary refractive index of 1.5 to 1.75 with respect to light having a wavelength of 455 nm to 465 nm.

[0032] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, a layer formed of the arylamine compound has an ordinary refractive index with respect to light of a wavelength of 633 nm of 1.45 to 1.70.

[0033] Another embodiment of the present invention is an arylamine compound having the above structure and a molecular weight of 400 to 1100.

[0034] Another embodiment of the present invention is an arylamine compound having the above structure, wherein the glass transition point is 100° C. or higher, preferably 110° C. or higher, and more preferably 120° C. or higher.

[0035] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the arylamine compound is a monoamine compound.

[0036] Another embodiment of the present invention is an arylamine compound represented by the following general formula (G1).

[0037] [Chemical Formula 1]

[0038]

[0039] In the above general formula (G1), Ar 1 represents a substituted or unsubstituted benzene ring or a substituent formed by two or three substituted or unsubstituted benzene rings bonded to each other. 6 、R 7 and R 8 Each independently represents an alkyl group having 1 to 4 carbon atoms, and m represents an integer from 0 to 4. When m is 2 or more, multiple R 8 Can be the same or different. 11 to R 15 One of them is a substituent represented by the above general formula (g1), and the others are independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. 21 to R 25 One of them is a substituent represented by the above general formula (g2), and the others are independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkylphenyl group substituted with 1 to 6 carbon atoms. 31 to R 35 R each independently represents 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. 11 to R 15 、R 21 to R 25 and R 31 to R 35At least three of the groups are alkyl groups having 1 to 6 carbon atoms, and R 11 to R 15 One of the following is a substituted or unsubstituted phenyl group, R 21 to R 25 and R 31 to R 35 One or less of R is a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms. 12 and R 14 、R 22 and R 24 and R 32 and R 34 In at least two of the three combinations, at least one R is a substituent other than hydrogen.

[0040] Another embodiment of the present invention is an arylamine compound represented by the following general formula (G2).

[0041] [Chemical Formula 2]

[0042]

[0043] In the above general formula (G2), p and r each independently represent 1 or 2, and p+r is 2 or 3. 6 to R 9 Each independently represents an alkyl group having 1 to 4 carbon atoms, and m and n each independently represent an integer from 0 to 4. 41 to R 45 Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms. When m is 2 or more, multiple R 8 They may be the same or different. When n is 2 or more, multiple R 9 When p is 2, the types, number and bond positions of the substituents of the two phenylene groups may be the same or different. When r is 2, the types, number and bond positions of the substituents of the two phenyl groups may be the same or different. 11 to R 15 One of them is a substituent represented by the above general formula (g1), and the others are independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. 21 to R 25 One of them is a substituent represented by the above general formula (g2), and the others are 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. 31 to R 35R each independently represents 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. 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of the groups are alkyl groups having 1 to 6 carbon atoms, and R 11 to R 15 One of the following is a substituted or unsubstituted phenyl group, R 21 to R 25 and R 31 to R 35 One or less of R is a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms. 12 and R 14 、R 22 and R 24 and R 32 and R 34 In at least two of the three combinations, at least one R is a substituent other than hydrogen.

[0044] Another embodiment of the present invention is an arylamine compound, wherein n is 0 in the above structure.

[0045] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, p is 1 and r is 1.

[0046] Another embodiment of the present invention is an arylamine compound represented by the following general formula (G3).

[0047] [Chemical Formula 3]

[0048]

[0049] In the above general formula (G3), R 1 to R 5 R each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, and a substituted or unsubstituted phenyl group. 6 、R 7 and R 8 Each independently represents an alkyl group having 1 to 4 carbon atoms, and m represents an integer from 0 to 4. When m is 2 or more, multiple R 8 They can also be the same or different. 11 to R 15 One of them is a substituent represented by the above general formula (g1), and the others are independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. 21 to R25 One of them is a substituent represented by the above general formula (g2), and the others are 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. 31 to R 35 R each independently represents 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. 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of the groups are alkyl groups having 1 to 6 carbon atoms, and R 11 to R 15 One of the following is a substituted or unsubstituted phenyl group, R 21 to R 25 and R 31 to R 35 One or less of R is a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms. 12 and R 14 、R 22 and R 24 and R 32 and R 34 In at least two of the three combinations, at least one R is a substituent other than hydrogen.

[0050] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the R 1 to R 5 Medium R 3 is cyclohexyl, and the others are hydrogen.

[0051] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the R 1 to R 5 Medium R 1 is unsubstituted phenyl, and the others are hydrogen.

[0052] Another embodiment of the present invention is an arylamine compound, wherein in the above structure, the R 12 、R 14 、R 22 and R 24 At least one of the substituents is other than hydrogen, and the R 32 and R 34 At least one of the substituents is other than hydrogen.

[0053] Another embodiment of the present invention is an arylamine compound, wherein m is 0 in the above structure.

[0054] Another embodiment of the present application is an arylamine compound in the above structure, wherein the alkyl group having 1 to 6 carbon atoms is a chain alkyl group having 2 to 5 carbon atoms.

[0055] Another embodiment of the present application is an arylamine compound in the above structure, wherein the alkyl group having 1 to 6 carbon atoms is a chain alkyl group having 2 to 5 carbon atoms.

[0056] Another embodiment of the present application is an arylamine compound in the above structure, wherein the alkyl group having 1 to 6 carbon atoms is a chain alkyl group having 2 to 5 carbon atoms.

[0057] Another embodiment of the present application is an arylamine compound in the above structure, wherein R 11 to R 15 , R 21 to R 25 , and R 31 to R 35 are the substituents other than hydrogen, and the others are hydrogen. 12 , R 14 , R 22 , R 32 , and R 34 are the substituents other than hydrogen, and the others are hydrogen.

[0058] Another embodiment of the present application is an arylamine compound in the above structure, wherein R 12 is a substituent represented by the general formula (g1), and R 22 is a substituent represented by the general formula (g2).

[0059] Another embodiment of the present application is an arylamine compound in the above structure, wherein R 14 , R 32 , and R 34 are tert-butyl groups.

[0060] Another embodiment of the present application is an arylamine compound in the above structure, wherein R 5 , and R 6 are methyl groups.

[0061] Another embodiment of the present application is an arylamine compound in the above structure, wherein the ordinary light refractive index of a layer formed of the arylamine compound with respect to light having a wavelength of 455 nm or more and 465 nm or less is 1.50 or more and 1.75 or less.

[0062] Another embodiment of the present application is an arylamine compound in the above structure, wherein the ordinary light refractive index of a layer formed of the arylamine compound with respect to light having a wavelength of 633 nm is 1.45 or more and 1.70 or less.

[0063] Another embodiment of the present invention is an arylamine compound having the above structure, wherein the glass transition point is 100° C. or higher, preferably 110° C. or higher, and more preferably 120° C. or higher.

[0064] Another embodiment of the present invention is a hole transport layer material comprising the above-mentioned arylamine compound.

[0065] Another embodiment of the present invention is a hole injection layer material comprising the above-mentioned arylamine compound.

[0066] Another embodiment of the present invention is a hole injection material including: the above-mentioned arylamine compound; and an organic compound having a cyano group or a fluorine atom.

[0067] Another embodiment of the present invention is a light-emitting device using any of the above-mentioned organic compounds.

[0068] Another embodiment of the present invention is an electronic device including: the light-emitting device described in any one of the above items; and at least one of a sensor, an operation button, a speaker, and a microphone.

[0069] Another embodiment of the present invention is a light-emitting device including: the light-emitting device described in any one of the above items; and at least one of a transistor and a substrate.

[0070] Another embodiment of the present invention is a lighting device including: the light-emitting device described in any one of the above items; and a housing.

[0071] In this specification, a light-emitting device includes an image display device using a light-emitting device. Furthermore, a light-emitting device may also include a module in which a light-emitting device is attached to a connector such as an anisotropic conductive film or a tape carrier package (TCP); a module in which a printed circuit board is attached to the end of a TCP; or a module in which an integrated circuit (IC) is directly mounted on a light-emitting device using a COG (Chip On Glass) method. Furthermore, a lighting device may also include a light-emitting device.

[0072] One embodiment of the present invention can provide a novel hole transport layer material. One embodiment of the present invention can provide a hole transport layer material having a low refractive index. One embodiment of the present invention can provide a hole transport layer material having a low refractive index and sufficient hole transport properties.

[0073] One embodiment of the present invention can provide a novel hole injection layer material. One embodiment of the present invention can provide a hole injection layer material having a low refractive index. One embodiment of the present invention can provide a hole injection layer material having a low refractive index and sufficient hole transport properties.

[0074] One embodiment of the present invention can provide a novel arylamine compound. One embodiment of the present invention can provide a novel arylamine compound having sufficient hole-transporting properties. One embodiment of the present invention can provide an arylamine compound having a low refractive index. One embodiment of the present invention can provide an arylamine compound having a low refractive index and sufficient hole-transporting properties.

[0075] One embodiment of the present invention can provide a light-emitting device with high luminous efficiency. One embodiment of the present invention can provide a light-emitting device, a light-emitting apparatus, an electronic device, a display device, and an electronic device with low power consumption.

[0076] Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not necessarily have all of the above effects. Note that effects other than the above can be understood and extracted from the description of the specification, drawings, claims, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0077] Figure 1A 、 Figure 1B and Figure 1C is a schematic diagram of a light emitting device;

[0078] Figure 2A and Figure 2B This is a conceptual diagram of an active matrix light-emitting device;

[0079] Figure 3A and Figure 3B This is a conceptual diagram of an active matrix light-emitting device;

[0080] Figure 4 This is a conceptual diagram of an active matrix light-emitting device;

[0081] Figure 5A and Figure 5B This is a conceptual diagram of a passive matrix light-emitting device;

[0082] Figure 6A and Figure 6B is a diagram showing a lighting device;

[0083] Figure 7A 、 Figure 7B1 、 Figure 7B2 and Figure 7C is a diagram showing an electronic device;

[0084] Figure 8A 、 Figure 8B and Figure 8C is a diagram showing an electronic device;

[0085] Figure 9 is a diagram showing a lighting device;

[0086] Figure 10is a view showing a lighting device;

[0087] Figure 11 is a view showing a car-mounted display device and a lighting device;

[0088] Figure 12A and Figure 12B is a view showing an electronic device;

[0089] Figure 13A , Figure 13B and Figure 13C is a view showing an electronic device;

[0090] Figure 14A and Figure 14B is a 1H NMR spectrum of mmtBumTPFA-02; 1

[0091] Figure 15 is an absorption spectrum and an emission spectrum of mmtBumTPFA-02 in a toluene solution;

[0092] Figure 16 is a MS spectrum of mmtBumTPFA-02;

[0093] Figure 17 is a measurement result of the refractive index of mmtBumTPFA-02;

[0094] Figure 18A and Figure 18B is a 1H NMR spectrum of mmtBumTPFBi-02; 1

[0095] Figure 19 is an absorption spectrum and an emission spectrum of mmtBumTPFBi-02 in a toluene solution;

[0096] Figure 20 is a MS spectrum of mmtBumTPFBi-02;

[0097] Figure 21 is a measurement result of the refractive index of mmtBumTPFBi-02;

[0098] Figure 22A and Figure 22B is a 1H NMR spectrum of mmtBumTPoFBi-02; 1

[0099] Figure 23 is an absorption spectrum and an emission spectrum of mmtBumTPoFBi-02 in a toluene solution;

[0100] Figure 24 is a MS spectrum of mmtBumTPoFBi-02; ​​​

[0101] Figure 25 is the measurement result of the refractive index of mmtBumTPoFBi-02;

[0102] Figure 26A and Figure 26B It is mmtBumTPchPAF-02 1 H NMR spectrum;

[0103] Figure 27 are the absorption and emission spectra of mmtBumTPchPAF-02 in toluene solution;

[0104] Figure 28 is the MS spectrum of mmtBumTPchPAF-02;

[0105] Figure 29 is the measurement result of the refractive index of mmtBumTPchPAF-02;

[0106] Figure 30A and Figure 30B It is mmtBumTPoFBi-03 1 H NMR spectrum;

[0107] Figure 31 are the absorption and emission spectra of mmtBumTPoFBi-03 in toluene solution;

[0108] Figure 32 is the MS spectrum of mmtBumTPoFBi-03;

[0109] Figure 33 is the measurement result of the refractive index of mmtBumTPoFBi-03;

[0110] Figure 34A and Figure 34B It is mmtBumTPchPAF-03 1 H NMR spectrum;

[0111] Figure 35 are the absorption and emission spectra of mmtBumTPchPAF-03 in toluene solution;

[0112] Figure 36 is the MS spectrum of mmtBumTPchPAF-03;

[0113] Figure 37 is the measurement result of the refractive index of mmtBumTPchPAF-03;

[0114] Figure 38The refractive index measurement results of mmtBumTPchPAF-02, mmtBumTPoFBi-02, and PCBBiF are shown below:

[0115] Figure 39 is the brightness-current density characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1;

[0116] Figure 40 1 is the current efficiency-brightness characteristic of the light emitting device 1, the light emitting device 2 and the comparative light emitting device 1;

[0117] Figure 41 is the brightness-voltage characteristic of the light emitting device 1, the light emitting device 2, and the comparative light emitting device 1;

[0118] Figure 42 is the current-voltage characteristic of the light emitting device 1, the light emitting device 2, and the comparative light emitting device 1;

[0119] Figure 43 is the external quantum efficiency-brightness characteristic of the light emitting device 1, the light emitting device 2, and the comparative light emitting device 1;

[0120] Figure 44 are the emission spectra of light emitting device 1, light emitting device 2, and comparison light emitting device 1;

[0121] Figure 45 The refractive index measurement results of mmtBumTPchPAF-03, mmtBumTPoFBi-03 and PCBBiF are shown below:

[0122] Figure 46 is the brightness-current density characteristics of light emitting device 3, light emitting device 4 and comparison light emitting device 2;

[0123] Figure 47 1 is the current efficiency-brightness characteristic of light emitting device 3, light emitting device 4 and comparison light emitting device 2;

[0124] Figure 48 is the brightness-voltage characteristics of light emitting device 3, light emitting device 4 and comparison light emitting device 2;

[0125] Figure 49 is the current-voltage characteristics of light emitting device 3, light emitting device 4 and comparison light emitting device 2;

[0126] Figure 50 1 is the external quantum efficiency-brightness characteristic of light emitting device 3, light emitting device 4 and comparative light emitting device 2;

[0127] Figure 51 are the emission spectra of light emitting device 3, light emitting device 4, and comparison light emitting device 2;

[0128] Figure 52 The refractive index measurement results of mmtBumTPchPAF-02, mmtBumTPoFBi-02, mmtBumTPchPAF-03, mmtBumTPoFBi-03 and PCBBiF are shown.

[0129] Figure 53 1 is the brightness-current density characteristic of light emitting device 5, light emitting device 6, light emitting device 7, light emitting device 8 and comparison light emitting device 3;

[0130] Figure 54 1 is the current efficiency-brightness characteristic of light emitting device 5, light emitting device 6, light emitting device 7, light emitting device 8 and comparison light emitting device 3;

[0131] Figure 55 1 is the brightness-voltage characteristic of light emitting device 5, light emitting device 6, light emitting device 7, light emitting device 8 and comparison light emitting device 3;

[0132] Figure 56 are the current-voltage characteristics of light emitting device 5, light emitting device 6, light emitting device 7, light emitting device 8, and comparison light emitting device 3;

[0133] Figure 57 1 is the external quantum efficiency-luminance characteristic of light emitting device 5, light emitting device 6, light emitting device 7, light emitting device 8 and comparison light emitting device 3;

[0134] Figure 58 are emission spectra of light emitting device 5, light emitting device 6, light emitting device 7, light emitting device 8, and comparison light emitting device 3;

[0135] Figure 59 The refractive index measurement results of mmtBumTPchPAF-02, mmtBumTPoFBi-02, and PCBBiF are shown below:

[0136] Figure 60 1 is the brightness-current density characteristic of light emitting device 9, light emitting device 10 and comparison light emitting device 4;

[0137] Figure 61 1 is the current efficiency-brightness characteristic of light emitting device 9, light emitting device 10 and comparison light emitting device 4;

[0138] Figure 62 1 is the brightness-voltage characteristic of light emitting device 9, light emitting device 10 and comparison light emitting device 4;

[0139] Figure 63 are the current-voltage characteristics of light emitting device 9, light emitting device 10, and comparison light emitting device 4;

[0140] Figure 64is the blue index-brightness characteristic of light emitting device 9, light emitting device 10, and comparison light emitting device 4;

[0141] Figure 65 are emission spectra of light emitting device 9, light emitting device 10, and comparison light emitting device 4;

[0142] Figure 66 1 is a diagram showing changes in luminance of the light emitting device 9, the light emitting device 10, and the comparative light emitting device 4 relative to driving time;

[0143] Figure 67 1 is a diagram showing changes in luminance of the light emitting device 1, the light emitting device 2, and the comparative light emitting device 1 relative to driving time;

[0144] Figure 68 The refractive index measurement results of mmtBumTPchPAF-02, mmtBumTPoFBi-02, and PCBBiF are shown below:

[0145] Figure 69 1 is the brightness-current density characteristic of the light emitting device 11, the light emitting device 12 and the comparative light emitting device 5;

[0146] Figure 70 1 is the current efficiency-brightness characteristic of the light emitting device 11, the light emitting device 12, and the comparative light emitting device 5;

[0147] Figure 71 1 is the brightness-voltage characteristic of the light emitting device 11, the light emitting device 12, and the comparative light emitting device 5;

[0148] Figure 72 1 is the current-voltage characteristic of the light emitting device 11, the light emitting device 12, and the comparative light emitting device 5;

[0149] Figure 73 is the blue index-brightness characteristic of the light emitting device 11, the light emitting device 12, and the comparative light emitting device 5;

[0150] Figure 74 are the emission spectra of light emitting device 11, light emitting device 12, and comparison light emitting device 5;

[0151] Figure 75 1 is a diagram showing changes in luminance of the light emitting device 11, the light emitting device 12, and the comparative light emitting device 5 relative to driving time;

[0152] Figure 76 is the current density-voltage characteristic of device 1 and device 2;

[0153] Figure 77 is a graph showing the electric field intensity dependence of the hole mobility of the organic compound according to one embodiment of the present invention;

[0154] Figure 78A and Figure 78B It is mmtBumTPoFBi-04 1 H NMR spectrum;

[0155] Figure 79 are the absorption and emission spectra of mmtBumTPoFBi-04 in toluene solution;

[0156] Figure 80 is the MS spectrum of mmtBumTPoFBi-04;

[0157] Figure 81A and Figure 81B It is mmtBumTPchPAF-04 1 H NMR spectrum;

[0158] Figure 82 are the absorption and emission spectra of mmtBumTPchPAF-04 in toluene solution;

[0159] Figure 83 is the MS spectrum of mmtBumTPchPAF-04;

[0160] Figure 84A and Figure 84B It is mmtBumTPoFBi-05 1 H NMR spectrum;

[0161] Figure 85 are the absorption and emission spectra of mmtBumTPoFBi-05 in toluene solution;

[0162] Figure 86A and Figure 86B It is mmtBumTPchPAF-05 1 H NMR spectrum;

[0163] Figure 87 are the absorption and emission spectra of mmtBumTPchPAF-05 in toluene solution;

[0164] Figure 88 is mmtBumQPoFBi 1 H NMR spectrum;

[0165] Figure 89 is mmtBumQPchPAF 1 H NMR spectrum. DETAILED DESCRIPTION

[0166] The following describes embodiments of the present invention in detail with reference to the accompanying drawings. Note that the present invention is not limited to the following description, and those skilled in the art will readily appreciate that its embodiments and details can be modified in various ways without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited solely to the embodiments described below.

[0167] Implementation Method 1

[0168] 1,1-Bis-(4-bis(4-methyl-phenyl)-amino-phenyl)-cyclohexane (TAPC) is known as one of the low-refractive-index materials among organic compounds with carrier-transporting properties that can be used in organic EL devices. Using a low-refractive-index material in the EL layer can produce a light-emitting device with high external quantum efficiency. Therefore, the use of TAPC is expected to produce a light-emitting device with excellent external quantum efficiency.

[0169] Generally speaking, there is a trade-off between high carrier transport and low refractive index. This is because the carrier transport in organic compounds mostly comes from the presence of unsaturated bonds, and organic compounds with many unsaturated bonds tend to have a high refractive index. TAPC is a substance with an excellent balance between hole transport and low refractive index, but in compounds with 1,1-disubstituted cyclohexanes such as TAPC, two bulky substituents are bonded to one carbon atom of cyclohexane, thereby increasing steric repulsion and causing the molecule itself to be unstable, resulting in reduced reliability. In addition, since the skeleton structure of TAPC is composed of cyclohexane and a simple benzene ring, the glass transition point (Tg) is low and there are also problems with heat resistance.

[0170] One method for obtaining a hole transport material with high heat resistance and good reliability is to introduce an unsaturated hydrocarbon group, particularly a cyclic unsaturated hydrocarbon group, into the molecule. On the other hand, to obtain a material with a low refractive index, it is preferred to introduce a substituent with a low molecular refractive index into the molecule. Examples of such substituents include saturated hydrocarbon groups and cyclic saturated hydrocarbon groups.

[0171] Furthermore, materials used as carrier transport materials in organic EL devices preferably have a backbone with high carrier transport properties. Aromatic amine backbones are particularly preferred because they exhibit high hole transport properties. To further enhance hole transport, the introduction of two amine backbones can be considered. However, as with the aforementioned TAPC, a diamine structure can sometimes be detrimental to reliability, depending on the substituents placed around the amine backbone.

[0172] The present inventors have found that a saturated hydrocarbon group consisting of sp 3The ratio of carbon atoms bonded by hybrid orbitals is within a certain range. In particular, the arylamine compound is a material having the same good reliability as the existing hole transport layer material having a normal refractive index. In addition, by adjusting the sp 3 The arylamine compound can have better properties by increasing the number or position of the substituents (ie, alkyl and cycloalkyl) on the carbon atom to which the hybrid orbital forms a bond.

[0173] That is, the organic compound of one embodiment of the present invention is an arylamine compound having at least one aromatic group, in which the first benzene ring, the second benzene ring and the third benzene ring are directly bonded in sequence and have at least three alkyl groups. By having at least three alkyl groups in the aromatic group, a material for a hole transport layer with a low refractive index can be achieved. Note that the alkyl group is preferably an alkyl group with 1 to 6 carbon atoms. Note that from the viewpoint of reducing the refractive index, a chain alkyl group with 2 or more carbon atoms is preferred, and from the viewpoint of ensuring carrier transportability, a chain alkyl group with 5 or less carbon atoms is preferred. In addition, since the refractive index reducing effect of a branched chain alkyl group with 3 or more carbon atoms is significant, a chain alkyl group with 2 to 5 carbon atoms is particularly preferred, and a branched chain alkyl group with 3 to 5 carbon atoms is more preferred. Note that a tert-butyl group is more preferred.

[0174] Note that the first benzene ring may further have a substituted or unsubstituted phenyl group, and the second benzene ring or the third benzene ring may further have an alkylated phenyl group.

[0175] Here, the first benzene ring in the above-mentioned aromatic group is bonded to the nitrogen of the amine, and the carbon atoms at the 1-position and 3-position of two or more of the first benzene ring, the second benzene ring and the third benzene ring are bonded to a substituent other than hydrogen. These 1-position and 3-position are preferably bonded to the nitrogen of an alkyl group, a benzene ring or an amine. That is, two or more of the first benzene ring, the second benzene ring and the third benzene ring are independently bonded to the nitrogen of other benzene rings (for example, any one of the first to third benzene rings or the benzene ring of the above-mentioned alkylated phenyl group) at the 1-position and 3-position, respectively. Note that the arylamine compound as one embodiment of the present invention is preferably a triarylamine compound from the viewpoint of the electrical stability of the light-emitting device. In addition, from the viewpoint of low refractive index or sublimation, the triarylamine compound is preferably a monoamine compound (that is, there is only one nitrogen in the compound to which three aryl groups are bonded to an amine).

[0176] In the first benzene ring, if one of the carbon atoms located between the carbon atoms bonded to the nitrogen of the amine has a substituent, the substituent is preferably the second benzene ring. When two carbon atoms at the meta positions have substituents, preferably one is the second benzene ring and the other is an alkyl group or a benzene ring containing an alkyl group. Furthermore, in the second benzene ring, if one of the carbon atoms located between the carbon atoms bonded to the first benzene ring has a substituent, the substituent is preferably the third benzene ring. When two carbon atoms at the meta positions have substituents, preferably one is the third benzene ring and the other is an alkyl group or an alkylated phenyl group. In the third benzene ring, if a carbon atom located between the carbon atoms bonded to the second benzene ring has a substituent, the substituent is preferably an alkyl group or an alkylated phenyl group.

[0177] Note that, in the phenyl group substituted with an alkyl group that can be used as a substituent for the second and third benzene rings, at least one of the carbon atoms at the meta position is preferably substituted with an alkyl group, and more preferably both carbon atoms at the meta position are substituted with an alkyl group. Furthermore, bonding two or more of these alkylated phenyl groups rarely contributes to a reduction in refractive index, but increases in molecular weight lead to a reduction in sublimation properties. Therefore, bonding to only one of the second and third benzene rings is preferred.

[0178] Note that, when the second benzene ring or the third benzene ring has an alkylated phenyl group, the number of alkyl groups possessed by the above-mentioned aromatic group also includes the number of alkyl groups bonded to the phenyl group.

[0179] Furthermore, as long as at least two of the first to third benzene rings are bonded to nitrogen atoms of a benzene ring, an alkyl group, or an amine at the 1- and 3-positions, the other benzene rings may have substituents at any carbon atom positions.

[0180] In this way, it is preferred that two or more of the first, second, and third benzene rings are bonded to other benzene rings, benzene rings of alkylated phenyl groups, alkyl groups, or nitrogen of amines at the 1- and 3-positions, thereby further reducing the refractive index.

[0181] It is preferred that all benzene rings in the first through third benzene rings and the benzene rings of the alkylated phenyl group be bonded at the 1- and 3-positions to nitrogen atoms in other benzene rings, alkyl groups (e.g., any of the at least three alkyl groups mentioned above), or amines, because this reduces the refractive index. Furthermore, it is preferred that all benzene rings in the first through third benzene rings and the alkylated phenyl group be bonded at the 1-, 3-, and 5-positions to nitrogen atoms in other benzene rings, alkyl groups (e.g., any of the at least three alkyl groups mentioned above), or amines, and that the remaining carbon atoms be unsubstituted, because this shortens the conjugation. Extended conjugation of the benzene rings can also lead to undesirable effects on light-emitting devices, such as absorption of light in the visible region.

[0182] Note that when the second and / or third benzene rings have an alkylated phenyl group, the phenyl group preferably has an alkyl group at both meta positions, more preferably also has an alkyl group at both meta positions, and the ortho and para positions are unsubstituted.

[0183] Furthermore, the first benzene ring preferably further comprises a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group, as shielding of the amine nitrogen is suppressed. In this case, the substituted or unsubstituted phenyl group is preferably bonded to the ortho position of the first benzene ring as carrier transport properties are improved. When the substituted or unsubstituted phenyl group has a substituent, the substituent is an alkyl group.

[0184] The above-mentioned arylamine compound preferably has a second aromatic group because the hole transport property is improved. The second aromatic group is preferably a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring skeleton with 3 or less rings because the hole transport property is improved. When the number of rings in the fused ring skeleton increases, the refractive index tends to increase. When having the above structure, a low refractive index can be maintained. In addition, similarly, when the number of rings in the fused ring skeleton increases, absorption or luminescence of light in the visible region is observed, so a material that is less affected by absorption or luminescence can be obtained. Note that in order to maintain a low refractive index, the number of carbon atoms forming the fused ring skeleton of the second aromatic group is preferably 6 to 13. As aromatic groups that can be used as the second aromatic group, specifically, benzene rings, naphthalene rings, fluorene rings, acenaphthylene rings, etc. can be cited. In particular, the second aromatic group preferably has a fluorene ring, more preferably a fluorene ring, because the hole transport property can be improved. Note that the second aromatic group is more preferably a dimethylfluorene group because the durability of the material is improved. In particular, the absence of other substituents in the dimethylfluorenyl group allows hole transport properties to be maintained, making this a preferred structure. Note that since the second aromatic group is directly bonded to the amine nitrogen of the arylamine compound, this contributes to a shallower HOMO energy level of the molecule, thereby facilitating hole transport and is therefore preferred.

[0185] Note that the above-mentioned alkyl group is preferably an alkyl group having 1 to 6 carbon atoms. Note that, from the viewpoint of reducing the refractive index, a chain alkyl group having 2 or more carbon atoms is preferred, and from the viewpoint of ensuring carrier transportability, a chain alkyl group having 5 or less carbon atoms is preferred. In addition, a branched chain alkyl group having 3 or more carbon atoms has a significant effect of reducing the refractive index. That is, the above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 to 5 carbon atoms, and more preferably a branched chain alkyl group having 3 to 5 carbon atoms. The alkyl group having 1 to 6 carbon atoms is preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, and hexyl group, and is particularly preferably a tert-butyl group.

[0186] In addition, the above-mentioned arylamine compound preferably has a third aromatic group. The third aromatic group is preferably a group having one to three substituted or unsubstituted benzene rings. When the third aromatic group has two or three benzene rings, the two or three benzene rings are preferably substituents bonded to each other. That is, the third aromatic group is preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthylphenyl group. Note that the third aromatic group is preferably a biphenyl group bonded in the ortho position because the hole transport property is improved. In addition, when one or more of the one to three benzene rings have a substituent, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, etc. can be used as the substituent. Note that the alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 or more carbon atoms from the viewpoint of reducing the refractive index, and is preferably a chain alkyl group having 5 or less carbon atoms from the viewpoint of ensuring carrier transport. In addition, the group with a significant refractive index reducing effect is a branched chain alkyl group having 3 or more carbon atoms. That is, the alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 to 5 carbon atoms, and more preferably a branched chain alkyl group having 3 to 5 carbon atoms. The alkyl group having 1 to 6 carbon atoms is preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, or pentyl group, and tert-butyl group is particularly preferred. Note that, as the cycloalkyl group having 5 to 12 carbon atoms, cyclohexyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, decalinyl group, cycloundecyl group, and cyclododecyl group can be used. Cycloalkyl groups having 6 or more carbon atoms are preferred, and cyclohexyl group and cyclododecyl group are particularly preferred.

[0187] Note that the arylamine compound of one embodiment of the present invention is preferably a monoamine compound. In addition, the arylamine compound of one embodiment of the present invention is preferably a triarylamine compound from the viewpoint of hole transport properties.

[0188] The arylamine compound of one embodiment of the present invention having the structure described above can be a compound with a very low refractive index, that is, the ordinary refractive index for light in the entire range of wavelengths from 455 nm to 465 nm is from 1.5 to 1.75, and the ordinary refractive index for light with a wavelength of 633 nm is from 1.45 to 1.70. Note that when the material has anisotropy, the ordinary refractive index and the extraordinary refractive index may be different. When the measured film is in the above state, the ordinary refractive index and the extraordinary refractive index can be calculated separately by performing anisotropic analysis. Note that in this specification, when the measured material has both an ordinary refractive index and an extraordinary refractive index, the ordinary refractive index is used as an indicator.

[0189] The arylamine compound of one embodiment of the present invention having the above-described structure can achieve high heat resistance with a glass transition point of 100° C. or higher. In a more preferred embodiment of the present invention, the glass transition point can be 110° C. or higher, more preferably 120° C. or higher.

[0190] Further, the formation by the vapor deposition method can realize the low refractive index and the high heat resistance as described above, and therefore the molecular weight is preferably 400 or more and 1100 or less.

[0191] The arylamine compound having the structure as described above is an organic compound having a hole-transport property and a low refractive index, and therefore can be used as a material for a hole-transport layer or a hole-injection layer of an organic EL device. Further, the organic EL device using the material for the hole-transport layer or the hole-injection layer can realize a light-emitting device having a high luminous efficiency, i.e., an external quantum efficiency, a current efficiency, and a blue index, because the hole-transport layer and the hole-injection layer have a low refractive index. In addition, in the organic EL device using the material for the hole-transport layer or the hole-injection layer, the material for the hole-transport layer or the hole-injection layer is preferably an arylamine compound, and the stability of the molecule can be improved by reducing steric hindrance by limiting the number of aromatic groups bonded to a saturated hydrocarbon group, and therefore a long-life light-emitting device can be realized.

[0192] Note that, among the arylamine compounds described above, an organic compound represented by the following general formula (G1) is particularly preferable.

[0193] [Chemical Formula 4]

[0194]

[0195] Note that, in the above general formula (G1), Ar 1 represents a substituted or unsubstituted benzene ring or a substituent in which two or three substituted or unsubstituted benzene rings are bonded to each other. As Ar 1 , specifically, a phenyl group, a biphenyl group, a terphenyl group, a naphthylphenyl group, and the like can be given, and a phenyl group is particularly preferable in order to reduce the refractive index while maintaining the hole-transport property of a nitrogen atom.

[0196] Further, one of R 11 to R 15 is a substituent represented by the above general formula (g1), and the others each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. Note that the substituted or unsubstituted phenyl group is preferably an unsubstituted phenyl group, and when having a substituent, the number of carbon atoms of the phenyl group is 1 to 6.

[0197] Further, in the above general formula (g1), one of R 21 to R 25 is a substituent represented by the above general formula (g2), and the others each independently represent 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.

[0198] In the above general formula (g2), R31 to R 35 Each independently represents 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.

[0199] Here, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of the groups are alkyl groups having a carbon number of 1 to 6. Therefore, the arylamine compound represented by the general formula (G1) can be an arylamine compound having a low refractive index.

[0200] Furthermore, R 11 to R 15 The number of substituted or unsubstituted phenyl groups is 1 or less.

[0201] In addition, R 21 to R 25 and R 31 to R 35 The number of the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms is 1 or less, that is, 1 or 0.

[0202] Note that R 12 and R 14 、R 22 and R 24 and R 32 and R 34 In at least two of the three combinations of 12 and R 14 The benzene ring has R 22 and R 24 The benzene ring and R 32 and R 34 At least one of the carbon atoms at the meta position in each of the two or more benzene rings is not hydrogen, that is, has a substituent. In addition, in this case, it is preferred that R 12 、R 14 、R 22 、R 24 At least one of the substituents is other than hydrogen and R 32 and R 34 At least one of the substituents is other than hydrogen.

[0203] R 6 、R 7 and R 8 Each independently represents an alkyl group having 1 to 4 carbon atoms, and m represents an integer from 0 to 4. Note that when m is 2 or more, multiple R 8Can be the same or different.

[0204] Specific examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, and isobutyl, with tert-butyl being particularly preferred.

[0205] When the substituted or unsubstituted benzene ring or the substituted or unsubstituted phenyl group has a substituent, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms can be used as the substituent.

[0206] The above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 or more carbon atoms from the viewpoint of reducing the refractive index, and is preferably a chain alkyl group having 5 or less carbon atoms from the viewpoint of ensuring carrier transportability. In addition, a branched chain alkyl group having 3 or more carbon atoms has a significant effect of reducing the refractive index. That is, the above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 to 5 carbon atoms, and more preferably a branched chain alkyl group having 3 to 5 carbon atoms. As the alkyl group having 1 to 6 carbon atoms, specifically, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, etc., and tert-butyl is particularly preferred.

[0207] In addition, as the above-mentioned cycloalkyl group having 5 to 12 carbon atoms, specifically, cyclohexyl, 4-methylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, decahydronaphthyl, cycloundecyl and cyclododecyl can be used. In order to reduce the refractive index, it is preferred to use a cycloalkyl group having 6 or more carbon atoms, and cyclohexyl and cyclododecyl are particularly preferred.

[0208] In the above general formula (G1), Ar 1 The substituent is preferably a substituent in which two or three substituted or unsubstituted benzene rings are bonded to each other. Specifically, an arylamine compound represented by the following general formula (G2) is preferred.

[0209] [Chemical Formula 5]

[0210]

[0211] Note that in the general formula (G2), p and r each independently represent 1 or 2, and p+r is 2 or 3. Note that when p is 2, the type, number, and bond position of the substituents between the two phenylene groups may be the same or different, and when r is 2, the type, number, and bond position of the substituents in the two phenyl groups may be the same or different. Note that preferably, p is 1 and r is 1.

[0212] R 41 to R 45Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms.

[0213] In addition, R 9 represents an alkyl group having 1 to 4 carbon atoms, n represents an integer from 0 to 4, and when n is 2 or more, multiple R 9 They may be the same or different. In addition, n is preferably 0.

[0214] Specific examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl and tert-butyl, with tert-butyl being particularly preferred.

[0215] The above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 or more carbon atoms from the viewpoint of reducing the refractive index, and is preferably a chain alkyl group having 5 or less carbon atoms from the viewpoint of ensuring carrier transportability. In addition, a group having a significant refractive index reducing effect is a branched chain alkyl group having 3 or more carbon atoms. That is, the above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 to 5 carbon atoms, and more preferably a branched chain alkyl group having 3 to 5 carbon atoms. As the alkyl group having 1 to 6 carbon atoms, specifically, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, etc., and tert-butyl is particularly preferred.

[0216] In addition, as the above-mentioned cycloalkyl group having 5 to 12 carbon atoms, specifically, cyclohexyl, 4-methylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, decahydronaphthyl, cycloundecyl and cyclododecyl can be used. In order to reduce the refractive index, it is preferred to use a cycloalkyl group having 6 or more carbon atoms, and cyclohexyl and cyclododecyl are particularly preferred.

[0217] Note that R 6 、R 7 、R 11 to R 15 、R 21 to R 25 、R 31 to R 35 , m are the same as those in the general formula (G1), and thus their description is omitted.

[0218] In the above general formula (G1), Ar 1 One substituted or unsubstituted benzene ring is preferred. Specifically, an arylamine compound represented by the following general formula (G3) is preferred.

[0219] [Chemical Formula 6]

[0220]

[0221] In the above general formula (G3), R1 to R 5 Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, and a substituted or unsubstituted phenyl group.

[0222] Note that in the above general formula (G3), it is preferred that R 1 to R 5 R in 3 is cyclohexyl, and the others are hydrogen. 1 to R 5 R in 1 An unsubstituted phenyl group and hydrogen atoms in the rest are preferable because the hole transporting property can be improved.

[0223] When the substituted or unsubstituted phenyl group has a substituent, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms can be used as the substituent.

[0224] The above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 or more carbon atoms from the viewpoint of reducing the refractive index, and is preferably a chain alkyl group having 5 or less carbon atoms from the viewpoint of ensuring carrier transportability. In addition, a branched chain alkyl group having 3 or more carbon atoms has a significant effect of reducing the refractive index. That is, the above-mentioned alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 to 5 carbon atoms, and more preferably a branched chain alkyl group having 3 to 5 carbon atoms. As the alkyl group having 1 to 6 carbon atoms, specifically, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, etc., and tert-butyl is particularly preferred.

[0225] In addition, as the above-mentioned cycloalkyl group having 5 to 12 carbon atoms, specifically, cyclohexyl, 4-methylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, decahydronaphthyl, cycloundecyl and cyclododecyl can be used. In order to reduce the refractive index, it is preferred to use a cycloalkyl group having 6 or more carbon atoms, and cyclohexyl and cyclododecyl are particularly preferred.

[0226] Note that R 6 、R 7 、R 11 to R 15 、R 21 to R 25 、R 31 to R 35 , m are the same as those in the general formula (G1), and thus their description is omitted.

[0227] Note that, in the arylamine compounds represented by the above-mentioned general formulae (G1) to (G3), m is preferably 0.

[0228] Furthermore, among the arylamine compounds represented by the above-mentioned general formulae (G1) to (G3), it is preferred that R 11 to R 15 、R 21 to R 25 and R 31 to R 35 R in 12 、R 14 、R 22 、R 32 and R 34 is a substituent other than hydrogen, and the others are hydrogen. In addition, it is preferred that R 12 is a substituent represented by the general formula (g1), R 22 is a substituent represented by the general formula (g2). 14 、R 32 and R 34 Preferred is tert-butyl.

[0229] The arylamine compound of one embodiment of the present invention having the structure described above can be a compound with a very low refractive index, that is, the ordinary refractive index for light in the entire wavelength range of 455 nm to 465 nm is 1.5 to 1.75, and the ordinary refractive index for light at a wavelength of 633 nm is 1.45 to 1.70.

[0230] The organic compound of one embodiment of the present invention having the structure described above exhibits excellent hole-transport properties and a low refractive index, and therefore can be used as a hole-transport layer material or a hole-injection layer material in an organic EL device. Furthermore, organic EL devices using this hole-transport layer material or hole-injection layer material can achieve luminous efficiency, i.e., high external quantum efficiency, current efficiency, and blue index, due to the presence of a hole-transport layer and a hole-injection layer with low refractive index.

[0231] Specific examples of the organic compound having the above structure are shown below.

[0232] [Chemical Formula 7]

[0233]

[0234] [Chemical Formula 8]

[0235]

[0236] [Chemical Formula 9]

[0237]

[0238] [Chemical Formula 10]

[0239]

[0240] [Chemical Formula 11]

[0241]

[0242] [Chemical Formula 12]

[0243]

[0244] [Chemical Formula 13]

[0245]

[0246] [Chemical Formula 14]

[0247]

[0248] [Chemical Formula 15]

[0249]

[0250] [Chemical Formula 16]

[0251]

[0252] [Chemical Formula 17]

[0253]

[0254] [Chemical Formula 18]

[0255]

[0256] [Chemical Formula 19]

[0257]

[0258] [Chemical Formula 20]

[0259]

[0260] [Chemical Formula 21]

[0261]

[0262] [Chemical Formula 22]

[0263]

[0264] [Chemical Formula 23]

[0265]

[0266] [Chemical Formula 24]

[0267]

[0268] [Chem. 25]

[0269]

[0270] [Chem. 26]

[0271]

[0272] [Chem. 27]

[0273]

[0274] [Chem. 28]

[0275]

[0276] [Chem. 29]

[0277]

[0278] [Chem. 30]

[0279]

[0280] [Chem. 31]

[0281]

[0282] [Chem. 32]

[0283]

[0284] [Chem. 33]

[0285]

[0286] [Chem. 34]

[0287]

[0288] [Chem. 35]

[0289]

[0290] [Chem. 36]

[0291]

[0292] Embodiment 2

[0293] Figure 1AA diagram showing a 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 . The organic compound described in Embodiment 1 is used for the EL layer.

[0294] The EL layer 103 includes a light-emitting layer 113 and may further include a hole-injection layer 111 and / or a hole-transport layer 112. The light-emitting layer 113 contains a light-emitting material, and the light-emitting device of one embodiment of the present invention emits light from this light-emitting material. The light-emitting layer 113 may also contain a host material and other materials. The organic compound of one embodiment of the present invention described in Embodiment 1 may be included in any of the light-emitting layer 113, the hole-transport layer 112, and the hole-injection layer 111.

[0295] Note that although Figure 1A In addition to the above, an electron transport layer 114 and an electron injection layer 115 are also shown in FIG. 1 , but the structure of the light emitting device is not limited thereto.

[0296] Since this organic compound has a good hole-transporting property, it is suitable for use in the hole-transporting layer 112. In addition, a film in which the organic compound of one embodiment of the present invention is mixed with an acceptor substance can be used as the hole-injection layer 111.

[0297] Furthermore, the organic compound of one embodiment of the present invention can also be used as a host material. Furthermore, the hole transport material and the electron transport material can be co-evaporated to form an exciplex. By forming an exciplex having an appropriate emission wavelength, efficient energy transfer to the luminescent material can be achieved, thereby providing a light-emitting device with high efficiency and a long lifespan.

[0298] Since the organic compound of one embodiment of the present invention has a relatively low refractive index, a light-emitting device having excellent external quantum efficiency can be obtained by using it inside the EL layer.

[0299] Next, examples of the detailed structure and materials of the light-emitting device are described. As described above, the light-emitting device of one embodiment of the present invention includes the EL layer 103 having multiple layers between a pair of electrodes, the first electrode 101 and the second electrode 102 . Any layer of the EL layer 103 contains the organic compound disclosed in Embodiment 1.

[0300] The first electrode 101 is preferably formed using a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, examples include indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, and indium oxide containing tungsten oxide and zinc oxide (IWZO). Although these conductive metal oxide films are usually formed by sputtering, they can also be formed by applying a sol-gel method. As an example of a formation method, a method of forming indium oxide-zinc oxide by sputtering using a target material having 1 wt% to 20 wt% of zinc oxide added to indium oxide can be cited. In addition, indium oxide (IWZO) containing tungsten oxide and zinc oxide can be formed by sputtering using a target material having 0.5 wt% to 5 wt% of tungsten oxide and 0.1 wt% to 1 wt% of zinc oxide added to indium oxide. Other examples include 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 nitride). Graphene can also be used. Furthermore, by using a composite material, described later, for the layer in contact with the first electrode 101 in the EL layer 103, it is possible to select an electrode material without taking the work function into consideration.

[0301] The EL layer 103 preferably has a stacked structure. There is no particular limitation on the stacked structure, and various layer structures such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier blocking layer, an exciton blocking layer, and a charge generation layer may be employed. In this embodiment, the following two structures are described: Figure 1A As shown, the structure includes a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114 and an electron injection layer 115; and Figure 1B As shown, the structure includes a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, an electron injection layer 115, and a charge generation layer 116. The materials constituting each layer are specifically shown below.

[0302] The hole-injection layer 111 is a layer containing a substance having an acceptor property. As the substance having an acceptor property, an organic compound or an inorganic compound can be used.

[0303] As acceptor substances, compounds having an electron-withdrawing group (halogen or cyano group) can be used, such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and 2-(7-dicyanomethylidene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile. Compounds in which an electron-withdrawing group is bonded to a fused aromatic ring having multiple heteroatoms, such as HAT-CN, are particularly preferred because they are thermally stable. In addition, [3]radialene derivatives containing electron-withdrawing groups (especially halogen groups such as fluorine groups and cyano groups) are particularly preferred because of their very high electron-accepting properties. Specifically, they include: α,α',α"-1,2,3-cycloalkyltriylidene tris[4-cyano-2,3,5,6-tetrafluorophenylacetonitrile], α,α',α"-1,2,3-cyclopropyltriylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenylacetonitrile], α,α',α"-1,2,3-cycloalkyltriylidene tris[2,3,4,5,6-pentafluorophenylacetonitrile]. As substances having acceptor properties, in addition to the above-mentioned organic compounds, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. Alternatively, phthalocyanine complex compounds such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc); aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as DNTPD); or polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviated as PEDOT / PSS) may be used to form the hole injection layer 111. A substance having acceptor properties can extract electrons from an adjacent hole transport layer (or hole transport material) by applying an electric field.

[0304] Alternatively, a composite material containing the aforementioned acceptor substance in a material having hole-transport properties can be used as the hole-injection layer 111. Note that by using a composite material containing an acceptor substance in a material having hole-transport properties, the work function of the electrode can be disregarded when selecting the material forming the electrode. In other words, not only materials with high work functions but also materials with low work functions can be used for the first electrode 101.

[0305] As the hole transport material for the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can be used. As the hole transport material for the composite material, it is preferred to use a hole mobility of 1×10 -6 cm 2 The following specifically lists organic compounds that can be used as the material having hole transport properties in the composite material.

[0306] Examples of aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (DPA3B). Specific examples of the carbazole derivatives include 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-bis(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenylanthracen-9-yl)phenyl]-9H-carbazole (abbreviation: CzPA), and 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene. Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthracene, 10,10'-diphenyl-9,9'-bianthracene, 10,10'-bis(2-phenylphenyl)-9,9'-bianthracene, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthracene, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, etc. In addition, pentacene, coronene, etc. can also be used. In addition, it may have a vinyl skeleton.As the aromatic hydrocarbon having a vinyl group, for example, 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), and the like can be given. In addition, the organic compound of one embodiment of the present application can be used.

[0307] In addition, a high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), and the like can be used.

[0308] As a material having hole-transporting properties used in the composite material, it is more preferable to have any of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, it can be an aromatic amine having a substituent including a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine including a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group. Note that when these second organic compounds are substances containing an N,N-bis(4-biphenyl)amino group, it is preferred because light-emitting devices with long life can be produced. Specific examples of the second organic compound include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4"-phenyltriphenylamine (abbreviated as BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-4-amino-p-ter ... )phenyl]-N-phenyl-4-benzidine (abbreviated as: ThBA1BP), 4-(2-naphthyl)-4',4"-diphenyltriphenylamine (abbreviated as: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4"-diphenyltriphenylamine (abbreviated as: BBAβNBi), 4,4'-diphenyl-4"-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBAαNβNB), 4,4'-diphenyl-4"-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBAαNβNB -03), 4,4'-diphenyl-4"-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviated as: BBAPβNB-03), 4,4'-diphenyl-4"-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBA(βN2)B), 4,4'-diphenyl-4"-(7;2'-binaphthyl-2-yl)-triphenylamine (abbreviated as: BBA(βN2)B-03), 4,4'-diphenyl-4"-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviated as: BBAβNαNB), 4,4'-Diphenyl-4"-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviated as BBAβNαNB-02), 4-(4-biphenyl)-4'-(2-naphthyl)-4"-phenyltriphenylamine (abbreviated as TPBiAβNB), 4-(3-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4"-phenyltriphenylamine (abbreviated as mTPBiAβNBi), 4-(4-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4"-phenyltriphenylamine (abbreviated as TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviated as αNBA1BP), 4,4'-bis(1 -naphthyl)triphenylamine (abbreviated as αNBB1BP), 4,4'-diphenyl-4"-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviated as YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tri(1,1'-biphenyl-4-yl)amine (abbreviated as YGTBi1BP-02), 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4"-phenyltriphenylamine (abbreviated as YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobiphenylamine [9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobis[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobis[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobis(9H-fluorene)-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzofuran- 4-Amine (abbreviated as: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviated as: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviated as: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as: PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-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'-spirobi-9H-fluorene-1-amine, and the like.

[0309] Note that the material having a hole-transport property used for the composite material is more preferably a substance having a deeper HOMO level with a HOMO level of -5.7 eV or more and -5.4 eV or less. When the material having a hole-transport property used for the composite material has a deeper HOMO level, holes are easily injected into the hole-transport layer 112, and a long-lived light-emitting element can be obtained.

[0310] Note that the monoamine compound described in Embodiment 1 is a material having a hole-transport property, which can be used as a material for a hole-injection layer in the composite material. By using the monoamine compound described in Embodiment 1, a layer with a low refractive index can be formed inside the EL layer 103, and the external quantum efficiency of the light-emitting element can be improved.

[0311] Note that by further mixing a fluoride of an alkali metal or an alkaline earth metal (preferably, the atomic ratio of fluorine atoms in the layer is 20 % or more) into the above composite material, the refractive index of the layer can be reduced. Thus, a layer with a low refractive index can be formed inside the EL layer 103, and the external quantum efficiency of the light-emitting element can be improved.

[0312] By forming the hole-injection layer 111, the hole-injection property can be improved, and thus a light-emitting element with a low driving voltage can be obtained. In addition, an organic compound having an acceptor property can be easily formed by evaporation, and is a material that is easy to use.

[0313] The hole transport layer 112 is formed to include a material having a hole transport property. The material having a hole transport property preferably has a 1×10 -6 cm 2 / Vs or higher. The monoamine compound described in Embodiment 1 is a material having hole-transporting properties and can be suitably used as a material for a hole-transporting layer. Therefore, it is preferred that the monoamine compound described in Embodiment 1 be included in the hole-transporting layer 112, and it is more preferred that the hole-transporting layer 112 be composed of the monoamine compound described in Embodiment 1. By including the monoamine compound described in Embodiment 1 in the hole-transporting layer 112, a layer with a low refractive index can be formed within the EL layer 103, and the external quantum efficiency of the light-emitting device can be improved.

[0314] When a material other than the monoamine compound described in Embodiment 1 is used for the hole transport layer 112, examples of the material having the hole transport property include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP), and 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP). triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBB1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene Compounds with an aromatic amine skeleton, such as 1,3-bis(N-carbazolyl)benzene (mCP), 4,4'-bis(N-carbazolyl)biphenyl (CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (CzTP), and 3,3'-bis(9-phenyl-9H-carbazole) (PCCP); and compounds with a carbazole skeleton, such as 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzothiophene). (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and compounds having a furan skeleton such as 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among them, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred because they have good reliability and high hole transport properties and help reduce the driving voltage.Note that as a material constituting the hole-transport layer 112 , any of the substances listed as the material having a hole-transport property for the composite material used for the hole-injection layer 111 can be used as appropriate.

[0315] The light-emitting layer 113 includes a light-emitting substance and a host material. Note that the light-emitting layer 113 may also include other materials. Alternatively, the light-emitting layer 113 may be a stack of two layers having different compositions.

[0316] The luminescent material may be a fluorescent material, a phosphorescent material, a material exhibiting thermally activated delayed fluorescence (TADF), or other luminescent materials. One embodiment of the present invention is more preferably used when the luminescent layer 113 is a layer exhibiting fluorescent light, particularly a layer exhibiting blue fluorescent light.

[0317] Examples of materials that can be used as the fluorescent substance in the light-emitting layer 113 include the following substances. Note that other fluorescent substances can also be used.

[0318] For example, 5,6-bis[4-(10-phenyl-9-anthracenyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthracenyl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N , N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated as: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2 -anthryl) triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl) perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N"-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene) )bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviated as DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated as 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), N,N,N',N',N",N",N"',N"'-octaphenyldibenzo[g,p] (chrysene)-2,7,10,15-tetramine (abbreviated as DBC1), coumarin 30, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviated as: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviated as: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]vinyl}-6-methyl-4H-pyran-4-ylidene)malononitrile (abbreviated as: DCM1), 2-{2-methyl-6-[2-(2,3,6,7 -tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviation: DCJTI), 2-{2- Tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]vinyl}-4H-pyran-4-ylidene)malononitrile (abbreviated as BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as BisDCJTM), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviated as 1,6BnfAPrn-03), 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10FrA2Nbf(IV)-02), etc. In particular, fused aromatic diamine compounds represented by pyrene diamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferred because they have suitable hole-trapping properties and good luminous efficiency and reliability.

[0319] When a phosphorescent substance is used as the light-emitting substance in the light-emitting layer 113 , examples of usable materials include the following substances.

[0320] For example, the following materials can be used: organic metal iridium complexes having a 4H-triazole skeleton, such as tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviated as [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Mptz)3]), and tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole]iridium(III) (abbreviated as [Ir(iPrptz-3b)3]); tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium(III) (abbreviated as [Ir(iPrptz-3b)3]; [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Prptz1-Me)3]), etc.; organometallic iridium complexes with an imidazole skeleton, such as fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviated as [Ir(iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as [Ir(dmpimpt-Me)3]); and bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2 '] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviated as: FIr6), bis [2- (4', 6'-difluorophenyl) pyridinium-N, C2 '] iridium (III) picolinate (abbreviated as: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C 2 '}iridium(III) picolinate (abbreviated as [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2 Organometallic iridium complexes with phenylpyridine derivatives having electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (FIr(acac)), are blue phosphorescent compounds with a peak emission wavelength between 440 and 520 nm.

[0321] In addition, tris(4-methyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-tert-butyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinyl]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl Organometallic iridium complexes with a pyrimidine skeleton, such as (acetylacetonato)bis(4,6-diphenylpyrimidino)iridium(III) (abbreviated as [Ir(dppm)2(acac)]); Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazino)iridium(III) (abbreviated as [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazino)iridium(III) (abbreviated as [Ir(mppr-iPr)2(acac)]); Organometallic iridium complexes with a pyrazine skeleton, such as tris(2-phenylpyridino-N,C 2 ') iridium (III) (abbreviated as [Ir(ppy)3]), bis(2-phenylpyridinium-N,C 2 ')iridium(III) acetylacetonate (abbreviated as [Ir(ppy)2(acac)]), bis(benzo[h]quinolinolato)iridium(III) acetylacetonate (abbreviated as [Ir(bzq)2(acac)]), tris(benzo[h]quinolinolato)iridium(III) (abbreviated as [Ir(bzq)3]), tris(2-phenylquinolinolato-N,C 2'] iridium (III) (abbreviated as [Ir(pq)3]), bis(2-phenylquinoline-N,C 2 Organometallic iridium complexes with a pyridine skeleton, such as iridium(III) acetylacetonate (abbreviated as [Ir(pq)2(acac)]), and rare earth metal complexes, such as terbium(III) tris(acetylacetonate)(monophenanthroline) (abbreviated as [Tb(acac)3(Phen)]). These compounds primarily emit green phosphorescence, with a peak emission wavelength between 500 and 600 nm. Organometallic iridium complexes with a pyrimidine skeleton are particularly preferred due to their exceptional reliability and luminous efficiency.

[0322] In addition, organic gold compounds having a pyrimidine skeleton such as (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl)(dipivaloylmethane)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalene-1-yl)pyrimidinyl](dipivaloylmethane)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]) can be cited. Iridium complexes; (acetylacetonato)bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazine)(dipivaloylmethane)iridium(III) (abbreviated as [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as [Ir(Fdpq)2(acac)]) and other organometallic iridium complexes with pyrazine skeletons; tris(1-phenylisoquinoline-N,C 2’ )iridium(III) (abbreviated as [Ir(piq)3]), bis(1-phenylisoquinoline-N,C 2’) iridium (III) acetylacetone (abbreviation: [Ir (piq) 2 (acac) ]) and the like having a pyridine skeleton; platinum complexes such as 2, 3, 7, 8, 12, 13, 17, 18-octylethyl-21H, 23H-porphine platinum (II) (abbreviation: PtOEP); and rare earth metal complexes such as tris (1, 3-diphenyl-1, 3-propanedionato) (phenanthroline) europium (III) (abbreviation: [Eu (DBM) 3 (Phen) ]) and tris [1- (2-thienoyl) -3, 3, 3-trifluoropropanedionato] (phenanthroline) europium (III) (abbreviation: [Eu (TTA) 3 (Phen) ]). The above substances are compounds that emit red phosphorescence, and have an emission peak at 600 nm to 700 nm. In addition, an organic metal iridium complex having a pyrazine skeleton can obtain red light emission with good color.

[0323] In addition, a known phosphorescent light emitting substance can be used in addition to the above phosphorescent compound.

[0324] As the TADF material, fullerene and a derivative thereof, acridine and a derivative thereof, and an eosin derivative, or the like can be used. In addition, a metal-containing porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd), or the like can be cited. As the metal-containing porphyrin, for example, protoporphyrin-tin fluoride complex (SnF2 (Proto IX) ), mesoporphyrin-tin fluoride complex (SnF2 (Meso IX) ), hemoporphyrin-tin fluoride complex (SnF2 (Hemato IX) ), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2 (Copro III-4Me) ), octaethylporphyrin-tin fluoride complex (SnF2 (OEP) ), etioporphyrin-tin fluoride complex (SnF2 (Etio I) ), and octaethylporphyrin-platinum chloride complex (PtCl2OEP), and the like represented by the following structural formulas can be cited.

[0325] [Chemical Formula 37]

[0326]

[0327] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindole[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), Heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, such as 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthene-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridinium)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA). The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, and both electron transport and hole transport properties are high, so it is preferred. In particular, in the skeleton with a π-electron-deficient heteroaromatic ring, a pyridine skeleton, a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton) and a triazine skeleton are stable and have good reliability, so it is preferred. In particular, the acceptance of the benzofuranopyrimidine skeleton, the benzothienopyrimidine skeleton, the benzofuranopyrazine skeleton, and the benzothienopyrazine skeleton is high and has good reliability, so it is preferred. In addition, in the skeleton with a π-electron-rich heteroaromatic ring, an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton and a pyrrole skeleton are stable and have good reliability, so it is preferred to have at least one of the above skeletons. In addition, a dibenzofuran skeleton is preferably used as a furan skeleton, and a dibenzothiophene skeleton is preferably used as a thiophene skeleton. As the pyrrole skeleton, it is particularly preferred to use an indole skeleton, a carbazole skeleton, an indolecarbazole skeleton, a bicarbazole skeleton, and a 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole skeleton. In a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded, the electron donating property of the π-electron-rich heteroaromatic ring and the electron accepting property of the π-electron-deficient heteroaromatic ring are both high, and the energy difference between the S1 energy level and the T1 energy level becomes small, so that thermally activated delayed fluorescence can be efficiently obtained, so it is particularly preferred. Note that an aromatic ring bonded with an electron-withdrawing group such as a cyano group can also be used instead of a π-electron-deficient heteroaromatic ring. In addition, as a π-electron-rich skeleton, an aromatic amine skeleton, a phenazine skeleton, etc. can be used.Further, as the π-electron deficient skeleton, an oxanthrene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring or a heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, or the like can be used. Thus, at least one of the π-electron deficient heteroaromatic ring and the π-electlectron rich heteroaromatic ring can be replaced with a π-electron deficient skeleton and a π-electron rich skeleton.

[0328] [Chemical Formula 38]

[0329]

[0330] A TADF material refers to a material in which the difference between the S1 level and the T1 level is small and which has a function of converting triplet excitation energy into singlet excitation energy through reverse intersystem crossing. Thus, it is possible to up-convert triplet excitation energy into singlet excitation energy (reverse intersystem crossing) by a small amount of thermal energy and to efficiently generate a singlet excitation state. Further, it is possible to convert triplet excitation energy into light emission.

[0331] An exciplex in which two substances form an excited state has a function of converting triplet excitation energy into singlet excitation energy as a TADF material because the difference between the S1 level and the T1 level is extremely small.

[0332] Note that as an index of the T1 level, a phosphorescence spectrum observed at a low temperature (e.g., 77 K to 10 K) can be used. In the case of a TADF material, it is preferable that, when the wavelength energy of an extrapolation line obtained by drawing a tangent line at the tail on the short-wavelength side of a fluorescence spectrum be the S1 level and the wavelength energy of an extrapolation line obtained by drawing a tangent line at the tail on the short-wavelength side of a phosphorescence spectrum be the T1 level, the difference between the S1 level and the T1 level be 0.3 eV or less, and more preferably 0.2 eV or less.

[0333] Further, when a TADF material is used as a light-emitting substance, the S1 level of the host material is preferably higher than the S1 level of the TADF material. Further, the T1 level of the host material is preferably higher than the T1 level of the TADF material.

[0334] As the host material of the light-emitting layer, a material having electron-transporting properties or a material having hole-transporting properties, various kinds of carrier-transporting materials such as the above-described TADF material, or the like can be used.

[0335] As a material having hole transport properties, it is preferable to use an organic compound having an amine skeleton or a π-electron excess heteroaromatic ring skeleton. For example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9 H-carbazol-3-yl) triphenylamine (abbreviated as: PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated as: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated as: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated as: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviated as: PCBAF), N-phenyl-N-[ Compounds with an aromatic amine skeleton, such as 4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobis[9H-fluorene]-2-amine (abbreviated as: PCBASF); compounds with a carbazole skeleton, such as 1,3-bis(N-carbazolyl)benzene (abbreviated as: mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviated as: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as: PCCP); 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as: DBT3P-I I), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviated as: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as: DBTFLP-IV) and compounds having a furan skeleton such as 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzofuran) (abbreviated as: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as: mmDBFFLBi-II). Among them, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred because they have good reliability and high hole transport properties and help reduce the driving voltage.Further, the organic compound exemplified as the material having a hole-transport property described above can also be used.

[0336] As materials having electron-transporting properties, for example, there can be mentioned: bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinolinolato)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) and other metal complexes or organic compounds including a π-electron-deficient heteroaromatic ring skeleton.Examples of organic compounds containing a π-electron-deficient heteroaromatic ring skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviated as OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), 2- Heterocyclic compounds with a polyazole skeleton, such as [3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II); 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviated as 4,6mPnP2Pm ), heterocyclic compounds having a diazine skeleton such as 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviated as 4,6mDBTP2Pm-II); 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviated as mFBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobis(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviated as BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine Heterocyclic compounds with a triazine skeleton, such as triazine (abbreviated as mBnfBPTzn) and 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated as mBnfBPTzn-02); and heterocyclic compounds with a pyridine skeleton, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviated as 35DCzPPy) and 1,3,5-tris[3-(3-pyridyl)phenyl]benzene (abbreviated as TmPyPB). Among these, heterocyclic compounds with a diazine skeleton, a triazine skeleton, or a pyridine skeleton are preferred due to their excellent reliability.In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and also contribute to lowering the driving voltage.

[0337] TADF materials that can be used as host materials include the same materials listed above. When using a TADF material as a host material, the triplet excitation energy generated by the TADF material is converted to singlet excitation energy via reverse intersystem crossing and further transferred to the luminescent material, thereby improving the luminescence efficiency of the light-emitting device. In this case, the TADF material acts as an energy donor, and the luminescent material acts as an energy acceptor.

[0338] This is particularly effective when the luminescent material is a fluorescent material. Furthermore, in order to achieve high luminous efficiency, the S1 energy level of the TADF material is preferably higher than the S1 energy level of the fluorescent material. Furthermore, the T1 energy level of the TADF material is preferably higher than the S1 energy level of the fluorescent material. Therefore, the T1 energy level of the TADF material is preferably higher than the T1 energy level of the fluorescent material.

[0339] Furthermore, it is preferable to use a TADF material that emits light at a wavelength that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent substance. This is preferable because the excitation energy is smoothly transferred from the TADF material to the fluorescent substance, allowing efficient emission of light.

[0340] In order to efficiently generate singlet excitation energy from triplet excitation energy by anti-intersystem crossing, carrier recombination is preferably generated in TADF material. In addition, it is preferred that the triplet excitation energy generated in TADF material is not transferred to the fluorescent material. For this reason, the fluorescent material preferably has a protecting group around the luminophore (the skeleton that becomes the cause of luminescence) possessed by the fluorescent material. As the protecting group, it is preferably a substituent without a π bond, preferably a saturated hydrocarbon, specifically, an alkyl group having 3 or more and 10 or less carbon atoms, a cycloalkyl group having 3 or more and 10 or less carbon atoms, a trialkylsilyl group having 3 or more and 10 or less carbon atoms, more preferably having multiple protecting groups. The substituent without a π bond has almost no function of transmitting carriers, so it has almost no effect on carrier transmission or carrier recombination, and the TADF material and the luminophore of the fluorescent material can be kept away from each other. Here, the luminophore refers to the atomic group (skeleton) that becomes the cause of luminescence in the fluorescent material. The luminophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of the condensed aromatic ring or condensed heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, and the like. In particular, a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, Fluorescent substances having a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because they have high fluorescence quantum yields.

[0341] When a fluorescent material is used as a luminescent material, a material having an anthracene skeleton is preferably used as a host material. By using a substance having an anthracene skeleton as a host material of a fluorescent material, a light-emitting layer having good luminous efficiency and durability can be achieved. Among the substances having an anthracene skeleton used as a host material, substances having a diphenylanthracene skeleton (especially a 9,10-diphenylanthracene skeleton) are chemically stable, so they are preferred. In addition, when the host material has a carbazole skeleton, the injection / transport properties of holes are improved, so it is preferred, especially in the case of a benzocarbazole skeleton comprising a benzene ring fused to carbazole, its HOMO energy level is about 0.1eV shallower than carbazole, and holes are easily injected, so it is more preferred. In particular, when the host material has a dibenzocarbazole skeleton, its HOMO energy level is about 0.1eV shallower than carbazole, and holes are easily injected, so it is preferred. Therefore, it is further preferred that the substance used as the main material is a substance having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). Note that from the perspective of the above-mentioned hole injection / transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton can also be used instead of the carbazole skeleton. Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as: PCPN), 9-[4-(10-phenylanthracene-9-yl)phenyl]-9H-carbazole (abbreviated as: CzPA), 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c,g] Carbazole (abbreviated as cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthracenyl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviated as 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}-anthracene (abbreviated as FLPPA), and 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviated as αN-βNPAnth). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred due to their excellent properties.

[0342] Alternatively, the host material may be a mixture of multiple substances. When a mixed host material is used, it is preferred to mix a material having electron-transporting properties with a material having hole-transporting properties. By mixing a material having electron-transporting properties with a material having hole-transporting properties, it is easier to adjust the transport properties of the light-emitting layer 113 and to more easily control the recombination area. The weight ratio of the material having hole-transporting properties to the material having electron-transporting properties can be from 1:19 to 19:1.

[0343] Note that a phosphorescent substance may be used as part of the mixed material. When a fluorescent substance is used as the luminescent substance, the phosphorescent substance may be used as an energy donor for supplying excitation energy to the fluorescent substance.

[0344] Alternatively, these mixed materials can be used to form an exciplex. Selecting mixed materials to form an exciplex that emits light at a wavelength overlapping with the absorption band on the lowest energy side of the luminescent substance is preferred because it facilitates energy transfer and efficiently produces luminescence. Furthermore, this structure is preferred because it reduces the driving voltage.

[0345] Note that at least one of the materials forming the exciplex may be a phosphorescent substance. This allows efficient conversion of triplet excitation energy into singlet excitation energy via reverse intersystem crossing.

[0346] Regarding the combination of materials that efficiently form exciplexes, the HOMO energy level of the material having hole transport properties is preferably greater than the HOMO energy level of the material having electron transport properties. In addition, the LUMO energy level of the material having hole transport properties is preferably greater than the LUMO energy level of the material having electron transport properties. Note that the LUMO energy level and HOMO energy level of the material can be determined from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV).

[0347] Note that the formation of an exciplex can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, the emission spectra of an electron-transporting material, and the emission spectra of a mixed film formed by mixing these materials. If the emission spectrum of the mixed film shifts toward the longer wavelength side compared to the emission spectra of each material (or has a new peak on the longer wavelength side), it indicates the formation of an exciplex. Alternatively, by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a mixed film formed by mixing these materials, if the transient response is different, such as a longer-life component or a larger ratio of delayed components compared to the transient PL lifetime of the mixed film, it indicates the formation of an exciplex. Furthermore, the above-mentioned transient PL can be referred to as transient electroluminescence (EL). In other words, the formation of an exciplex can be confirmed by observing the difference in transient response compared to the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a mixed film of these materials.

[0348] The electron-transport layer 114 is a layer containing a substance having an electron-transport property. As the substance having an electron-transport property, any of the above-described substances that can be used as the host material can be used.

[0349] Note that the electron transport layer preferably contains a material having an electron transport property and an alkali metal, an alkaline earth metal, a compound thereof, or a composite thereof. Furthermore, the electron transport layer 114 preferably has an electron mobility of 1×10- -7 cm 2 / Vs or above and 5×10 -5 cm 2 / Vs or less. By reducing the transportability of electrons in the electron transport layer 114, the amount of electrons injected into the light-emitting layer can be controlled, thereby preventing the light-emitting layer from becoming in a state with too many electrons. When a composite material is used to form a hole injection layer, it is particularly preferred that the HOMO energy level of the material with hole transport properties in the composite material is a deeper HOMO energy level of more than -5.7 eV and less than -5.4 eV, thereby obtaining a long life. Note that at this time, the HOMO energy level of the material with electron transport properties is preferably more than -6.0 eV. In addition, the material with electron transport properties is preferably an organic compound having an anthracene skeleton, more preferably an organic compound containing both an anthracene skeleton and a heterocyclic skeleton. As the heterocyclic skeleton, a nitrogen-containing five-membered ring skeleton or a nitrogen-containing six-membered ring skeleton is preferably used, and the heterocyclic skeleton is particularly preferably a nitrogen-containing five-membered ring skeleton or a nitrogen-containing six-membered ring skeleton containing two hetero atoms in the ring such as a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, etc. In addition, as alkali metals, alkaline earth metals, their compounds or their complexes, it is preferred to have an 8-hydroxyquinoline structure. Specifically, for example, 8-hydroxyquinoline-lithium (abbreviated as: Liq), 8-hydroxyquinoline-sodium (abbreviated as: Naq) and the like can be cited. Particularly preferred are complexes of monovalent metal ions, preferably lithium complexes, more preferably Liq. Note that when having an 8-hydroxyquinoline structure, methyl substituents (such as 2-methyl substituents or 5-methyl substituents) of alkali metals, alkaline earth metals, their compounds or their complexes can be used. In addition, it is preferred that there is a concentration difference (including the case of 0) in the electron transport layer in the thickness direction of the alkali metals, alkaline earth metals, their compounds or their complexes.

[0350] An electron injection layer 115 formed of an alkali metal, alkaline earth metal, or compound thereof, such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), or 8-hydroxyquinoline-lithium (abbreviated as Liq), can be provided between the electron transport layer 114 and the second electrode 102. The electron injection layer 115 can be formed by including an alkali metal, alkaline earth metal, or compound thereof within a layer composed of a substance having electron transport properties, or by using an electron compound. Examples of the electron compound include a substance obtained by adding electrons at a high concentration to a mixed oxide of calcium and aluminum.

[0351] Note that a layer containing an alkali metal or alkaline earth metal fluoride in a microcrystalline state (50 wt % or more) containing an electron-transporting substance (preferably an organic compound having a bipyridine skeleton) can also be used as the electron-injection layer 115. Since this layer has a low refractive index, a light-emitting device with improved external quantum efficiency can be provided.

[0352] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 ( Figure 1B ). The charge generation layer 116 is a layer that can inject holes into the layer in contact with the cathode side of the layer and inject electrons into the layer in contact with the anode side of the layer by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using the composite material constituting the hole injection layer 111. In addition, the P-type layer 117 can also be formed by stacking a film containing the above-mentioned accepting material and a film containing a hole transport material as a material constituting the composite material. By applying a potential to the P-type layer 117, electrons and holes are respectively injected into the electron transport layer 114 and the second electrode 102 serving as the cathode, so that the light-emitting device works. In addition, since the organic compound of one embodiment of the present invention is an organic compound with a relatively low refractive index, a light-emitting device with good external quantum efficiency can be obtained by using it for the P-type layer 117.

[0353] Furthermore, the charge generation layer 116 preferably includes, in addition to the P-type layer 117 , one or both of an electron relay layer 118 and an electron injection buffer layer 119 .

[0354] The electron relay layer 118 contains at least a substance with electron transport properties, and is capable of preventing the interaction between the electron injection buffer layer 119 and the P-type layer 117, and smoothly transferring electrons. The LUMO energy level of the substance with electron transport properties contained in the electron relay layer 118 is preferably set between the LUMO energy level of the accepting substance in the P-type layer 117 and the LUMO energy level of the substance contained in the layer in the electron transport layer 114 that contacts the charge generation layer 116. Specifically, the LUMO energy level of the substance with electron transport properties in the electron relay layer 118 is preferably above -5.0 eV, more preferably above -5.0 eV and below -3.0 eV. In addition, as the substance with electron transport properties in the electron relay layer 118, it is preferred to use a phthalocyanine material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0355] The electron injection buffer layer 119 can use substances with high electron injection properties such as alkali metals, alkaline earth metals, rare earth metals and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)).

[0356] In addition, when the electron injection buffer layer 119 contains a substance having an electron-transporting property and a donor substance, as the donor substance, in addition to alkali metals, alkaline earth metals, rare earth metals and compounds of these substances (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate or cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates) or rare earth metal compounds (including oxides, halides, carbonates)), organic compounds such as tetrathianaphthacene (abbreviated as: TTN), nickelocene, and decamethylnickelocene can also be used. In addition, as the substance having an electron-transporting property, the same material as the material for the electron transport layer 114 described above can be used.

[0357] As a material forming the second electrode 102, a metal, alloy, conductive compound, and mixture thereof with a small work function (specifically less than 3.8 eV) can be used. As specific examples of such cathode materials, elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals such as lithium (Li) or cesium (Cs), magnesium (Mg), calcium (Ca), or strontium (Sr), alloys containing them (MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them can be cited. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide can be used as the second electrode 102 regardless of the size of the work function. These conductive materials can be formed by dry methods such as vacuum evaporation and sputtering, inkjet methods, spin coating methods, etc. In addition, the second electrode 102 can be formed by a wet method such as a sol-gel method or a wet method using a paste of a metal material.

[0358] The EL layer 103 can be formed by various methods, whether dry or wet, such as vacuum deposition, gravure printing, rotogravure printing, screen printing, inkjet printing, or spin coating.

[0359] In addition, each of the electrodes or each layer described above may be formed by using a different film forming method.

[0360] Note that the structure of the layer provided between the first electrode 101 and the second electrode 102 is not limited to the above structure. However, it is preferable to adopt a structure in which a light-emitting region where holes and electrons recombine is provided at a location away from the first electrode 101 and the second electrode 102 in order to suppress quenching caused by the proximity of the light-emitting region to a metal used for an electrode or a carrier injection layer.

[0361] In addition, in order to suppress the energy transfer from excitons generated in the light-emitting layer, the carrier transport layer such as the hole transport layer and the electron transport layer in contact with the light-emitting layer 113, especially the carrier transport layer close to the recombination region in the light-emitting layer 113, is preferably composed of the following substances, that is, substances having a band gap larger than the band gap of the light-emitting material constituting the light-emitting layer or the light-emitting material contained in the light-emitting layer.

[0362] Next, refer to Figure 1C A light emitting device having a structure in which a plurality of light emitting units are stacked (hereinafter also referred to as a stacked element or a tandem element) is described. This light emitting device is a light emitting device having a plurality of light emitting units between an anode and a cathode. One light emitting unit has Figure 1A The EL layer 103 shown in FIG. 1 has a substantially similar structure. In other words, it can be said that Figure 1C The light emitting device shown is a light emitting device having a plurality of light emitting units. Figure 1A or Figure 1B The light-emitting device shown is a light-emitting device having one light-emitting unit.

[0363] exist Figure 1C In the embodiment, a first light emitting unit 511 and a second light emitting unit 512 are stacked between the anode 501 and the cathode 502, and a charge generation layer 513 is provided between the first light emitting unit 511 and the second light emitting unit 512. The anode 501 and the cathode 502 are equivalent to Figure 1A The first electrode 101 and the second electrode 102 in the embodiment of the present invention can be applied to Figure 1A In addition, the first light emitting unit 511 and the second light emitting unit 512 may have the same structure or different structures.

[0364] The charge generation layer 513 has a function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit when voltage is applied to the anode 501 and the cathode 502. Figure 1C When a voltage is applied so that the potential of the anode is higher than that of the cathode, the charge generation layer 513 may be a layer that injects electrons into the first light-emitting unit 511 and injects holes into the second light-emitting unit 512 .

[0365] The charge generation layer 513 preferably has Figure 1B The charge generation layer 116 shown in FIG. Because the composite material of the organic compound and the metal oxide has excellent carrier injection and carrier transport properties, it can achieve low-voltage and low-current driving. Note that when the anode-side surface of the light-emitting unit contacts the charge generation layer 513, the charge generation layer 513 can also function as the hole injection layer of the light-emitting unit, so the hole injection layer does not need to be provided in the light-emitting unit.

[0366] When the electron injection buffer layer 119 is provided in the charge generation layer 513, since the electron injection buffer layer 119 functions as an electron injection layer in the light-emitting unit on the anode side, an electron injection layer is not necessarily provided in the light-emitting unit on the anode side.

[0367] Although Figure 1C While a light-emitting device having two light-emitting units is described above, the same application can be applied to light-emitting devices having three or more stacked light-emitting units. As in the light-emitting device of this embodiment, by separating and arranging multiple light-emitting units between a pair of electrodes using the charge generation layer 513, the device can achieve high-brightness emission while maintaining a low current density, and can also achieve a long device life. Furthermore, a light-emitting device capable of low voltage operation and low power consumption can be realized.

[0368] Furthermore, by making each light-emitting unit emit a different color, the entire light-emitting device can emit light of a desired color. For example, by emitting red and green light from the first light-emitting unit and blue light from the second light-emitting unit in a light-emitting device having two light-emitting units, a light-emitting device can be obtained that emits white light throughout the entire device.

[0369] The EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, the charge generation layer, and other layers and electrodes can be formed by, for example, evaporation (including vacuum evaporation), droplet jetting (also known as inkjet), coating, gravure printing, or the like. Furthermore, they may include low-molecular-weight materials, medium-molecular-weight materials (including oligomers and dendrimers), or high-molecular-weight materials.

[0370] Implementation 3

[0371] In this embodiment, a light-emitting device using the light-emitting device described in Embodiment 2 is described.

[0372] In this embodiment, referring to Figure 2A and Figure 2B A light-emitting device manufactured using the light-emitting device described in Embodiment 2 will be described. Figure 2A is a top view showing a light emitting device, and Figure 2B It is along Figure 2A , a cross-sectional view taken along lines AB and CD in FIG. This light-emitting device includes a driver circuit (source line driver circuit) 601, a pixel portion 602, and a driver circuit portion (gate line driver circuit) 603, indicated by dashed lines, as a unit for controlling light emission from the light-emitting device. Reference numeral 604 denotes a sealing substrate, reference numeral 605 denotes a sealing material, and the space within the area surrounded by the sealing material 605 is a space 607.

[0373] Note that the lead wiring 608 is used to transmit signals input to the source line driver circuit 601 and the gate line driver circuit 603, and receives video signals, clock signals, start signals, reset signals, etc. from the FPC (flexible printed circuit) 609, which serves as an external input terminal. Note that although only the FPC is shown here, the FPC can also be mounted with a printed wiring board (PWB). The light-emitting device in this specification includes not only the light-emitting device body but also a light-emitting device mounted with an FPC or PWB.

[0374] Below, refer to Figure 2B A cross-sectional structure will be described. A driver circuit portion and a pixel portion are formed over an element substrate 610 , but here, a source line driver circuit 601 as a driver circuit portion and one pixel in a pixel portion 602 are shown.

[0375] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, or the like.

[0376] There are no particular restrictions on the structure of transistors used in pixels or driver circuits. For example, inverted-staggered transistors or staggered transistors can be used. In addition, top-gate transistors or bottom-gate transistors can be used. There are no particular restrictions on the semiconductor material used for the transistors. For example, silicon, germanium, silicon carbide, gallium nitride, etc. can be used. Alternatively, oxide semiconductors containing at least one of indium, gallium, and zinc, such as In-Ga-Zn metal oxides, can be used.

[0377] There are no particular restrictions on the crystallinity of the semiconductor material used for the transistor, and an amorphous semiconductor or a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in part thereof) can be used. The use of a crystalline semiconductor is preferred because it can suppress the degradation of transistor characteristics.

[0378] Here, oxide semiconductors are preferably used in semiconductor devices such as transistors provided in the above-mentioned pixels or driver circuits and transistors used in touch sensors described later. Oxide semiconductors having a wider band gap than silicon are particularly preferred. By using oxide semiconductors having a wider band gap than silicon, the off-state current of the transistor can be reduced.

[0379] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, the oxide semiconductor is more preferably an oxide semiconductor containing an oxide represented by an In-M-Zn-based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0380] In particular, as a semiconductor layer, it is preferable to use an oxide semiconductor film having multiple crystal parts whose c-axes are all oriented perpendicular to the formed surface of the semiconductor layer or the top surface of the semiconductor layer and have no grain boundaries between adjacent crystal parts.

[0381] By using the above-mentioned materials as the semiconductor layer, a highly reliable transistor with suppressed fluctuations in electrical characteristics can be realized.

[0382] Furthermore, because transistors with this semiconductor layer have a low off-state current, they can retain charge stored in capacitors via the transistors for a long period of time. By using these transistors in pixels, the driving circuit can be stopped while maintaining the grayscale of the image displayed in each display area. This results in electronic devices with extremely low power consumption.

[0383] In order to achieve the stabilization of the characteristics of the transistor, etc., it is preferable to provide a base film. As the base film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film can be used and manufactured in a single layer or a stacked layer. The base film can be formed by sputtering, CVD (Chemical Vapor Deposition) method (plasma CVD method, thermal CVD method, MOCVD (Metal Organic CVD: Organic Metal Chemical Vapor Deposition) method, etc.) or ALD (Atomic Layer Deposition) method, coating method, printing method, etc. Note that the base film can be omitted if it is not required.

[0384] Note that FET 623 is one of the transistors formed in the driver circuit 601. Alternatively, the driver circuit may be formed using various CMOS circuits, PMOS circuits, or NMOS circuits. Furthermore, although this embodiment shows a driver-integrated type in which the driver circuit is formed on the substrate, this structure is not necessarily required. The driver circuit may also be formed externally rather than on the substrate.

[0385] In addition, the pixel portion 602 is formed by multiple pixels, each of which includes a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain of the current control FET 612, but is not limited to this. A pixel portion combining three or more FETs and capacitors can also be used.

[0386] Note that the insulator 614 is formed to cover the end portion of the first electrode 613. Here, the insulator 614 can be formed using a positive photosensitive acrylic resin film.

[0387] Furthermore, the upper or lower end of the insulator 614 is formed into a curved surface to ensure good coverage with the EL layer and the like formed later. For example, when a positive-type photosensitive acrylic resin is used as the material for the insulator 614, it is preferable to form a curved surface having a curvature radius (0.2 μm to 3 μm) only at the upper end of the insulator 614. Either a negative-type photosensitive resin or a positive-type photosensitive resin can be used as the insulator 614.

[0388] An EL layer 616 and a second electrode 617 are formed over the first electrode 613. A material having a large work function is preferably used as the material for the first electrode 613, which functions as an anode. For example, in addition to single-layer films such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 to 20% by weight of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, or a Pt film, a stacked film composed of a titanium nitride film and a film primarily composed of aluminum, or a three-layer structure composed of a titanium nitride film, a film primarily composed of aluminum, and a titanium nitride film can also be used. Note that adopting a stacked-layer structure can reduce the wiring resistance, achieve good ohmic contact, and enable the use of the anode.

[0389] The EL layer 616 is formed by various methods such as vapor deposition using a vapor deposition mask, inkjet coating, and spin coating. The EL layer 616 has the structure described in Embodiment 2. Alternatively, low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers) may be used as other materials constituting the EL layer 616.

[0390] The material for the second electrode 617, which is formed on the EL layer 616 and serves as a cathode, is preferably a material having a small work function (e.g., Al, Mg, Li, Ca, or alloys or compounds thereof (e.g., MgAg, MgIn, AlLi)). Note that when light generated in the EL layer 616 is transmitted through the second electrode 617, it is preferable to use a stacked layer composed of a thin metal film and a transparent conductive film (e.g., ITO, indium oxide containing 2% to 20% by weight of zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO)) as the second electrode 617.

[0391] A light-emitting device is formed of a first electrode 613, an EL layer 616, and a second electrode 617. This light-emitting device is the light-emitting device described in Embodiment 2. A pixel portion includes a plurality of light-emitting devices, and the light-emitting device of this embodiment may include both the light-emitting device described in Embodiment 2 and a light-emitting device having another structure.

[0392] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 using the sealing material 605, and the light-emitting device 618 is disposed in a space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. Note that the space 607 is filled with a filler. This filler can be an inert gas (nitrogen, argon, etc.) or a sealing material. Forming a recess in the sealing substrate and placing a desiccant therein is preferred because this can suppress degradation caused by moisture.

[0393] Epoxy resin or glass frit is preferably used as the sealing material 605. These materials are preferably as impermeable to moisture and oxygen as possible. In addition, as a material for the sealing substrate 604, in addition to glass substrates and quartz substrates, plastic substrates made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, etc. can also be used.

[0394] Although Figure 2A and Figure 2B Although not shown, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. Alternatively, the protective film may be formed so as to cover the exposed portion of the sealing material 605. Furthermore, the protective film may be provided to cover the surfaces and side surfaces of the pair of substrates, the exposed side surfaces of the sealing layer, the insulating layer, etc.

[0395] A material that is not easily permeable to impurities such as water can be used as the protective film. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0396] As materials constituting the protective film, oxides, nitrides, fluorides, sulfides, ternary compounds, metals, or polymers can be used. For example, materials containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, indium oxide, etc.; materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride; nitrides containing titanium and aluminum; oxides containing titanium and aluminum; oxides containing aluminum and zinc; sulfides containing manganese and zinc; sulfides containing cerium and strontium; oxides containing erbium and aluminum; and oxides containing yttrium and zirconium.

[0397] The protective film is preferably formed by a film formation method with good step coverage. One of such methods is an atomic layer deposition (ALD) method. A material that can be formed by the ALD method is preferably used for the protective film. A protective film that is dense and in which defects such as cracks or pinholes are reduced or uniform thickness is provided can be formed by the ALD method. In addition, damage to the processed member when the protective film is formed can be reduced.

[0398] For example, a uniform and defect-free protective film can be formed on a surface having a complex concavo-convex shape or on the top surface, side surface, and back surface of a touch panel by the ALD method.

[0399] As described above, a light emitting device manufactured using the light emitting device shown in Embodiment 2 can be obtained.

[0400] Since the light emitting device in this embodiment uses the light emitting device shown in Embodiment 2, a light emitting device with excellent characteristics can be obtained. Specifically, the light emitting device using the light emitting device shown in Embodiment 2 has good light emitting efficiency, and thus a low-power-consumption light emitting device can be realized.

[0401] Figure 3A and Figure 3B An example of a full-color light emitting device in which a coloring layer (color filter) or the like is provided to a light emitting device that emits white light is shown. Figure 3A A substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driver circuit portion 1041, first electrodes 1024W, 1024R, 1024G, 1024B of a light emitting device, a separation wall 1025, an EL layer 1028, a second electrode 1029 of a light emitting device, a sealing substrate 1031, a sealing material 1032, and the like are shown.

[0402] In addition, in Figure 3A a coloring layer (a red coloring layer 1034R, a green coloring layer 1034G, and a blue coloring layer 1034B) is provided on a transparent substrate 1033. In addition, a black matrix 1035 can be provided. The transparent substrate 1033 provided with the coloring layer and the black matrix is aligned and fixed to the substrate 1001. In addition, the coloring layer and the black matrix 1035 are covered with a protective layer 1036. In addition, Figure 3A A light emitting layer in which light is not transmitted through the coloring layer and is transmitted to the outside and a light emitting layer in which light is transmitted through each coloring layer and is transmitted to the outside are shown. Light that is not transmitted through the coloring layer becomes white light and light that is transmitted through the coloring layer becomes red light, green light, and blue light, and thus an image can be displayed with four colors of pixels.

[0403] Figure 3B In the example shown, colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. As described above, colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0404] Although the above description describes a light-emitting device having a structure in which light is extracted from the substrate 1001 side where FETs are formed (bottom emission type), a light-emitting device having a structure in which light is extracted from the sealing substrate 1031 side (top emission type) may also be used. Figure 4 A cross-sectional view of a top-emitting light-emitting device is shown. In this case, a substrate that does not transmit light can be used as substrate 1001. The steps up to the fabrication of the connection electrode used to connect the FET to the anode of the light-emitting device are similar to those for a bottom-emitting light-emitting device. A third interlayer insulating film 1037 is then formed to cover the electrode 1022. This third interlayer insulating film 1037 may also have a planarizing function. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film or other known materials.

[0405] Although the first electrodes 1024W, 1024R, 1024G, and 1024B of the light emitting device are anodes, they may also be cathodes. Figure 4 In the case of a top-emission light-emitting device as shown, the first electrode is preferably a reflective electrode. The structure of the EL layer 1028 is the same as that of the EL layer 103 described in Embodiment 2, and employs an element structure capable of emitting white light.

[0406] In adopting Figure 4 In the case of the top emission structure shown, a sealing substrate 1031 provided with a coloring layer (a red coloring layer 1034R, a green coloring layer 1034G, and a blue coloring layer 1034B) can be used for sealing. The sealing substrate 1031 can also be provided with a black matrix 1035 located between pixels. The coloring layer (a red coloring layer 1034R, a green coloring layer 1034G, and a blue coloring layer 1034B) and the black matrix 1035 can also be covered by a protective layer 1036. In addition, as the sealing substrate 1031, a light-transmitting substrate is used. In addition, although an example of full-color display in four colors of red, green, blue, and white is shown here, it is not limited to this. In addition, full-color display can also be performed in four colors of red, yellow, green, and blue, or in three colors of red, green, and blue.

[0407] A microcavity structure is particularly suitable for top-emitting light-emitting devices. By using a reflective electrode as the first electrode and a semi-transmissive / semi-reflective electrode as the second electrode, a light-emitting device having a microcavity structure can be obtained. At least an EL layer is included between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light-emitting layer serving as the light-emitting region is included.

[0408] Note that the reflective electrode has a visible light reflectivity of 40% to 100%, preferably 70% to 100%, and a resistivity of 1×10 -2 Ωcm or less. In addition, the visible light reflectivity of the semi-transmissive and semi-reflective electrode is 20% to 80%, preferably 40% to 70%, and its resistivity is 1×10 -2 Ωcm or less.

[0409] Light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive / semi-reflective electrode, and resonates.

[0410] In this light-emitting device, the optical path length between the reflective electrode and the semi-transmissive / semi-reflective electrode can be varied by changing the thickness of the transparent conductive film, the composite material, or the carrier transport material. This allows the wavelength of light that resonates to be enhanced while wavelengths of light that do not resonate to be attenuated between the reflective electrode and the semi-transmissive / semi-reflective electrode.

[0411] Light reflected by the reflective electrode (first reflected light) significantly interferes with light directly incident from the light-emitting layer onto the semi-transmissive / semi-reflective electrode (first incident light). Therefore, the optical path length between the reflective electrode and the light-emitting layer is preferably adjusted to (2n-1)λ / 4 (note that n is a natural number greater than 1, and λ is the wavelength of the light to be amplified). By adjusting this optical path length, the first reflected light and the first incident light can be aligned in phase, thereby further amplifying the light emitted from the light-emitting layer.

[0412] In the above structure, the EL layer may include multiple light-emitting layers or a single light-emitting layer. For example, the above structure may be combined with the structure of a tandem light-emitting device, in which multiple EL layers are provided in a single light-emitting device with a charge generation layer sandwiched therebetween, and one or more light-emitting layers are formed within each EL layer.

[0413] By employing a microcavity structure, the intensity of light emitted in the frontal direction at a specific wavelength can be enhanced, thereby achieving reduced power consumption. Note that in the case of a light-emitting device that displays images using four sub-pixels—red, yellow, green, and blue—the brightness of yellow light can be enhanced, and since all sub-pixels can employ microcavity structures tailored to the wavelength of each color, a light-emitting device with excellent characteristics can be realized.

[0414] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2, so a light-emitting device with excellent characteristics can be obtained. Specifically, the light-emitting device described in Embodiment 2 has good luminous efficiency, thereby realizing a light-emitting device with low power consumption.

[0415] Although an active matrix light-emitting device has been described so far, a passive matrix light-emitting device will be described below. Figure 5A and Figure 5B A passive matrix light emitting device manufactured by using the present invention is shown. Note that Figure 5A is a perspective view showing a light emitting device, and Figure 5B It is along Figure 5A A cross-sectional view obtained by cutting along the line XY. Figure 5A and Figure 5B In the embodiment, an EL layer 955 is provided between an electrode 952 and an electrode 956 on a substrate 951. The end of the electrode 952 is covered by an insulating layer 953. An isolation layer 954 is provided on the insulating layer 953. The side walls of the isolation layer 954 have such an inclination that the closer to the substrate surface, the narrower the interval between the two side walls. In other words, the cross section of the isolation layer 954 in the short side direction is a trapezoid, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the top side (the side facing the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). In this way, by providing the isolation layer 954, defects of the light-emitting device caused by static electricity or the like can be prevented. In addition, in a passive matrix light-emitting device, by using the light-emitting device shown in embodiment 2, a light-emitting device with good reliability or a light-emitting device with low power consumption can also be obtained.

[0416] The light-emitting device described above can control each of a plurality of minute light-emitting devices arranged in a matrix, and therefore can be suitably used as a display device for displaying images.

[0417] In addition, this embodiment mode can be freely combined with other embodiment modes.

[0418] Implementation 4

[0419] In this embodiment, referring to Figure 6A and Figure 6B An example in which the light-emitting device described in Embodiment 2 is used in a lighting device will be described. Figure 6B is a top view of the lighting device. Figure 6A It is along Figure 6B Cross-sectional view along line ef.

[0420] In the lighting device of this embodiment, a first electrode 401 is formed on a light-transmitting substrate 400 serving as a support. The first electrode 401 corresponds to the first electrode 101 in Embodiment 1. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0421] In addition, a pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0422] An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to the structure of the EL layer 103 in Embodiment 1 or a structure in which the light-emitting unit 511, the light-emitting unit 512, and the charge generation layer 513 are combined. Note that for these structures, refer to the respective descriptions.

[0423] A second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 1. When light is extracted from the first electrode 401 side, the second electrode 404 is formed using a material with high reflectivity. A voltage is supplied to the second electrode 404 by connecting the second electrode 404 to the pad 412.

[0424] As described above, the lighting device described in this embodiment includes a light-emitting device including the first electrode 401, the EL layer 403, and the second electrode 404. Since this light-emitting device has high light emission efficiency, the lighting device of this embodiment can be a low-power lighting device.

[0425] The substrate 400 on which the light emitting device having the above structure is formed and the sealing substrate 407 are fixed and sealed using the sealing materials 405 and 406, thereby manufacturing a lighting device. Alternatively, only one of the sealing materials 405 and 406 may be used. Alternatively, the inner sealing material 406 (at Figure 6B The CMOS (not shown) is mixed with a desiccant, thereby absorbing moisture and improving reliability.

[0426] Furthermore, the pad 412 and a portion of the first electrode 401 can be used as external input terminals by extending outside the sealing materials 405 and 406. Alternatively, an IC chip 420 or the like having a converter mounted thereon may be provided as the external input terminal.

[0427] The lighting device described in this embodiment uses the light-emitting device described in Embodiment 2 as an EL device, and can realize a low-power-consumption light-emitting device.

[0428] Implementation 5

[0429] This embodiment describes an example of an electronic device that includes a light-emitting device described in Embodiment 2 as a portion thereof. The light-emitting device described in Embodiment 2 has good luminous efficiency and low power consumption. As a result, the electronic device described in this embodiment can be implemented as an electronic device including a light-emitting portion that consumes low power.

[0430] Examples of electronic devices employing the light-emitting devices include televisions (also referred to as television sets or television receivers), displays for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also referred to as mobile phones or mobile phone devices), portable game consoles, portable information terminals, audio reproduction devices, and large-scale game consoles such as pinball machines. Specific examples of these electronic devices are shown below.

[0431] Figure 7A An example of a television set is shown. In this television set, a display portion 7103 is incorporated into a housing 7101. The housing 7101 is supported by a bracket 7105. The display portion 7103 can display images and is formed by arranging the light-emitting devices described in Embodiment 2 in a matrix.

[0432] The television set can be operated using operation switches provided on the housing 7101 or a separately provided remote control unit 7110. Channels and volume can be controlled using operation keys 7109 provided on the remote control unit 7110, thereby controlling the image displayed on the display unit 7103. Furthermore, the remote control unit 7110 may be provided with a display unit 7107 for displaying information output from the remote control unit 7110.

[0433] Furthermore, television sets are configured with a receiver, a modem, and the like. The receiver can receive standard television broadcasts. Furthermore, the modem connects to a wired or wireless communication network, enabling one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers) information communication.

[0434] Figure 7B1 7 shows a computer including a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. The computer is manufactured by arranging the light-emitting devices described in Embodiment 2 in a matrix and using the light-emitting devices for the display portion 7203. Figure 7B1 The computer in can also be Figure 7B2 The method shown. Figure 7B2The computer shown is equipped with a second display unit 7210 in place of the keyboard 7204 and pointing device 7206. The second display unit 7210 is a touch panel, and input can be performed by operating the input display displayed on the second display unit 7210 with a finger or a dedicated pen. Furthermore, the second display unit 7210 can display not only the input display but also other images. Alternatively, the display unit 7203 can be a touch panel. Because the two screens are connected by a hinge, problems such as damage or breakage of the screens during storage or transportation can be prevented.

[0435] Figure 7C 1 shows an example of a portable terminal. The mobile phone includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. The mobile phone includes a display portion 7402 formed by arranging the light-emitting devices described in Embodiment 2 in a matrix.

[0436] Figure 7C The illustrated portable terminal may have a configuration in which information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a phone call and writing an e-mail can be performed by touching the display portion 7402 with a finger or the like.

[0437] The display portion 7402 has three main screen modes: a first display mode primarily for displaying images, a second input mode primarily for inputting information such as text, and a third display input mode that combines both a display mode and an input mode.

[0438] For example, when making a phone call or writing an e-mail, the text displayed on the screen can be input in a text input mode in which the display portion 7402 is mainly used to input text. In this case, it is preferred that a keyboard or number buttons be displayed in most parts of the screen of the display portion 7402.

[0439] Furthermore, by providing a detection device having a sensor for detecting inclination, such as a gyroscope or an accelerometer, within the portable terminal, the orientation (portrait or landscape) of the portable terminal can be determined and the screen display of the display portion 7402 can be automatically switched.

[0440] The screen mode is switched by touching the display portion 7402 or operating the operation button 7403 of the housing 7401. Alternatively, the screen mode may be switched according to the type of image displayed on the display portion 7402. For example, when the image signal displayed on the display portion is moving image data, the screen mode is switched to the display mode, while when the image signal is text data, the screen mode is switched to the input mode.

[0441] In addition, when a signal detected by the optical sensor of the display portion 7402 is detected in the input mode and it is found that there has been no touch operation input on the display portion 7402 for a certain period of time, control can be performed to switch the screen mode from the input mode to the display mode.

[0442] The display portion 7402 can also be used as an image sensor. For example, by touching the display portion 7402 with a palm or finger, palm prints or fingerprints can be captured, enabling personal identification. Furthermore, by using a backlight or a sensing light source that emits near-infrared light in the display portion, finger veins or palm veins can be captured.

[0443] Note that the structure described in this embodiment can be used in combination with the structures described in Embodiments 1 to 4 as appropriate.

[0444] As described above, a light-emitting device including the light-emitting device described in Embodiment 2 has a very wide range of applications and can be used in electronic devices in various fields. By using the light-emitting device described in Embodiment 2, an electronic device with low power consumption can be obtained.

[0445] Figure 8A 1 is a schematic diagram showing an example of a cleaning robot.

[0446] The robot vacuum cleaner 5100 includes a display 5101 on the top surface, multiple cameras 5102 on the side, a brush 5103, and operation buttons 5104. Although not shown, the bottom surface of the robot vacuum cleaner 5100 is provided with tires and a suction port. Furthermore, the robot vacuum cleaner 5100 includes various sensors, including infrared sensors, ultrasonic sensors, acceleration sensors, piezoelectric sensors, optical sensors, and gyroscope sensors. Furthermore, the robot vacuum cleaner 5100 includes a wireless communication unit.

[0447] The sweeping robot 5100 can walk automatically, detect garbage 5120, and suck the garbage from the suction port on the bottom.

[0448] In addition, the cleaning robot 5100 can analyze the images captured by the camera 5102 to determine the presence of obstacles such as walls, furniture, or steps. In addition, if the image analysis detects objects such as wiring that may be entangled with the brush 5103, the rotation of the brush 5103 can be stopped.

[0449] The remaining battery power and the amount of garbage attracted can be displayed on the display 5101. The walking path of the cleaning robot 5100 can be displayed on the display 5101. In addition, the display 5101 can be a touch panel, and the operation button 5104 can be displayed on the display 5101.

[0450] The robot vacuum cleaner 5100 can communicate with a portable electronic device 5140, such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the robot vacuum cleaner 5100 can also know the status of the room when leaving the house. In addition, the display content of the display 5101 can be confirmed using a portable electronic device such as a smartphone.

[0451] The light-emitting device of one embodiment of the present invention can be used for the display 5101.

[0452] Figure 8B The robot 2100 shown includes a computing device 2110 , an illumination sensor 2101 , a microphone 2102 , an upper camera 2103 , a speaker 2104 , a display 2105 , a lower camera 2106 , an obstacle sensor 2107 , and a moving mechanism 2108 .

[0453] The microphone 2102 has a function of detecting the user's voice and surrounding sounds, etc. The speaker 2104 has a function of emitting sounds. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0454] Display 2105 has the function of displaying various information. Robot 2100 can display user-desired information on display 2105. Display 2105 may be equipped with a touch panel. Display 2105 may be a detachable information terminal. By placing this information terminal at a predetermined location on robot 2100, it can be charged and transmit and receive data.

[0455] The upper camera 2103 and the lower camera 2106 have the function of capturing images of the environment surrounding the robot 2100. Furthermore, the obstacle sensor 2107 can detect the presence of obstacles in front of the robot 2100 as it moves using the moving mechanism 2108. The robot 2100 can use the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107 to recognize the surrounding environment and move safely. The light-emitting device of one embodiment of the present invention can be used for the display 2105.

[0456] Figure 8C1 is a diagram illustrating an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display portion 5001, a speaker 5003, an LED light 5004, a connection terminal 5006, a sensor 5007 (capable of measuring force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, inclination, vibration, odor, or infrared light), a microphone 5008, a display portion 5002, a support portion 5012, and earphones 5013.

[0457] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002 .

[0458] Figure 9 An example in which the light-emitting device described in Embodiment 2 is used in a desk lamp as a lighting device will be described. Figure 9 The table lamp shown includes a housing 2001 and a light source 2002 , and the lighting device described in Embodiment 3 is used as the light source 2002 .

[0459] Figure 10 An example of using the light-emitting device described in Embodiment 2 in an indoor lighting device 3001 is shown. Since the light-emitting device described in Embodiment 2 has high luminous efficiency, a low-power lighting device can be provided. Furthermore, since the light-emitting device described in Embodiment 2 can be fabricated over a large area, it can be used in a large-area lighting device. Furthermore, since the light-emitting device described in Embodiment 2 is thin, a thinner lighting device can be manufactured.

[0460] The light-emitting device described in Embodiment 2 can also be mounted on a windshield or an instrument panel of a car. Figure 11 This embodiment shows an embodiment in which the light-emitting device described in Embodiment 2 is used for a windshield or an instrument panel of a car. Display areas 5200 to 5203 are displays provided using the light-emitting device described in Embodiment 2.

[0461] Display area 5200 and display area 5201 are display devices mounted on the windshield of a car, and are equipped with the light-emitting device described in Embodiment 2. By using light-transmitting electrodes to manufacture the first and second electrodes of the light-emitting device described in Embodiment 2, a so-called see-through display device can be obtained, in which the scenery on the opposite side can be seen. If a see-through display is used, the field of vision is not obstructed even when it is installed on the windshield of a car. In addition, when providing transistors for driving, it is preferable to use light-transmitting transistors, such as organic transistors using organic semiconductor materials or transistors using oxide semiconductors.

[0462] Display area 5202 is a display device mounted on a pillar, equipped with the light-emitting device described in Embodiment 2. Displaying images from an imaging unit installed in the vehicle cabin on display area 5202 can supplement the field of view obscured by the pillar. Similarly, display area 5203 on the instrument panel can supplement blind spots obscured by the vehicle cabin by displaying images from an imaging unit installed outside the vehicle, thereby improving safety. By displaying images to supplement areas not visible, safety confirmation is more natural and simple.

[0463] Display area 5203 can also provide various information by displaying navigation information, speed, rpm, air conditioning settings, etc. The user can change the display content and layout as appropriate. Furthermore, this information can also be displayed on display areas 5200 through 5203. Furthermore, display areas 5200 through 5203 can also function as lighting devices.

[0464] Figure 12A and Figure 12B The foldable portable information terminal 5150 is shown. The foldable portable information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 5153. Figure 12A The portable information terminal 5150 is shown in the unfolded state. Figure 12B The portable information terminal 5150 is shown in a folded state. Although the portable information terminal 5150 has a large display area 5152, by folding the portable information terminal 5150, the portable information terminal 5150 becomes smaller and more portable.

[0465] The display area 5152 can be folded in half by the curved portion 5153. The curved portion 5153 is composed of a retractable member and a plurality of supporting members. When folding, the retractable member is stretched. The folding is performed so that the curved portion 5153 has a curvature radius of 2 mm or more, preferably 3 mm or more.

[0466] The display area 5152 may be a touch panel (input / output device) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used for the display area 5152.

[0467] also, 13A to 13C A foldable portable information terminal 9310 is shown. Figure 13A The portable information terminal 9310 is shown in the unfolded state. Figure 13B The portable information terminal 9310 is shown in a state halfway between the expanded state and the folded state. Figure 13CThe portable information terminal 9310 is shown in a folded state. The portable information terminal 9310 is highly portable in the folded state, and has a large, seamless display area in the unfolded state, providing a clear view of the display.

[0468] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. Note that the display panel 9311 may also be a touch panel (input / output device) equipped with a touch sensor (input device). Furthermore, by bending the display panel 9311 at the hinges 9313 between the two housings 9315, the portable information terminal 9310 can be reversibly changed from an unfolded state to a folded state. A light-emitting device according to one embodiment of the present invention can be used for the display panel 9311.

[0469] Example 1

[0470] "Synthesis Example 1"

[0471] In this example, a method for synthesizing the aromatic amine compound N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPFA-02), which is one embodiment of the present invention shown in Embodiment 1, is described. The structure of mmtBumTPFA-02 is shown below.

[0472] [Chemical Formula 39]

[0473]

[0474] <Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl>

[0475] 37.2g (128mmol) of 1,3-dibromo-5-tert-butylbenzene, 20.0g (85mmol) of 3,5-di-tert-butylphenylboric acid, 35.0g (255mmol) of potassium carbonate, 570mL of toluene, 170mL of ethanol, and 130mL of tap water were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, 382mg (1.7mmol) of palladium acetate and 901mg (3.4mmol) of triphenylphosphine were added, and the mixture was heated at 40°C for about 5 hours. Then, the temperature of the flask was returned to room temperature, and the organic layer and the aqueous layer were separated. Magnesium sulfate was added to the organic layer to remove moisture and concentrate the organic layer. The obtained solution was purified by silica gel column chromatography to obtain 21.5g of the target colorless oil with a yield of 63%. The following formula shows the synthesis scheme of step 1.

[0476] [Chemical Formula 40]

[0477]

[0478] <Step 2: Synthesis of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0479] 15.0 g (38 mmol) of 3-bromo-3',5,5'-tri-tert-butylbiphenyl obtained in Step 1, 10.5 g (41 mmol) of 4,4,4',4',5,5,5',5-octamethyl-2,2'-bi-1,3,2-dioxaborolane, 11.0 g (113 mmol) of potassium acetate, and 125 mL of N,N-dimethylformamide were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen. 1.5 g (1.9 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) was added, and the mixture was heated at 100°C for approximately 3 hours. The flask was then cooled to room temperature, the organic layer and the aqueous layer were separated, and the mixture was extracted with ethyl acetate. Magnesium sulfate was added to the extract to remove moisture and concentrate the extract. The resulting mixture was purified by silica gel column chromatography to a toluene solution, which was then concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and the solution was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at approximately 20°C, and the resulting solid was dried under reduced pressure at approximately 80°C to obtain 13.6 g of the desired product as a white solid in an 81% yield. The following formula shows the synthesis scheme for Step 2.

[0480] [Chemical Formula 41]

[0481]

[0482] <Step 3: Synthesis of 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl>

[0483] 5.0 g (11.1 mmol) of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4.8 g (16.7 mmol) of 1,3-dibromo-5-tert-butylbenzene, 4.6 g (33.3 mmol) of potassium carbonate, 56 mL of toluene, 22 mL of ethanol, and 17 mL of tap water were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen. 50 mg (0.22 mmol) of palladium acetate and 116 mg (0.44 mmol) of triphenylphosphine were added, and the mixture was heated at 80°C for approximately 10 hours. The flask was then allowed to return to room temperature, and the organic and aqueous layers were separated. Magnesium sulfate was added to the solution to remove moisture and concentrate it. The resulting hexane solution was purified by silica gel column chromatography to obtain 3.0 g of the desired product as a white solid in a 51.0% yield. The following formula represents the synthesis scheme for 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl in Step 3.

[0484] [Chemical Formula 42]

[0485]

[0486] <Step 4: Synthesis of mmtBumTPFA-02>

[0487] 3.0 g (5.6 mmol) of 3-bromo-3", 5,5', 5"-tetra-tert-butyl-1,1':3',1"-terphenyl, 1.6 g (5.6 mmol) of 2-anilino-9,9-dimethylfluorene, 1.6 g (16.8 mmol) of sodium tert-butoxide and 28 mL of toluene were placed in a three-necked flask, degassed under reduced pressure, and then the air in the flask was replaced with nitrogen. 64 mg (0.11 mmol) of bis(dibenzylideneacetone)palladium(0) and 138 mg (0.34 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl were added and the mixture was heated at 120°C. Heat the mixture for about 8 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash with toluene. Concentrate the filtrate, and purify the resulting toluene solution by silica gel column chromatography. Concentrate the resulting solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, remove ethanol from the resulting solid by reducing pressure at about 80°C, and obtain 3.2 g of the target product as a white solid with a yield of 78%. In addition, the following formula shows the synthesis scheme of mmtBumTPFA-02 in step 4.

[0488] [Chemical Formula 43]

[0489]

[0490] Figure 14A and Figure 14B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained in step 4. Note that Figure 14B It is magnified Figure 14A The graph shows the range of 6.5 ppm to 8.0 ppm in . Furthermore, the numerical data are shown below. Thus, in this synthesis example, N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine can be synthesized.

[0491] 1 H-NMR. δ (CDCl3): 7.63 (d, 1H, J=6.9Hz), 7.58 (d, 1H, J=8.0Hz), 7.51 (dd, 1H, J=1.7Hz), 7. 47 (dd, 1H, J = 1.7Hz), 7.45 (dd, 1H, J = 1.7Hz), 7.43 (dd, 1H, J = 1.7Hz), 7.39 (s, 1H), 7.38 (s, 1H), 7.38 (s, 1H), 7.26-7.32 (m, 4H), 7.19-7.25 (m, 5H), 7.17 (dd, 1H, J=1.7Hz), 7.07 (d, 1 H, J=6.3Hz), 7.02 (dd, 1H, J=7.5Hz), 1.42 (s, 6H), 1.38 (s, 9H), 1.36 (s, 18H), 1.29 (s, 9H).

[0492] Next, 3.2 g of the obtained white solid was purified by sublimation using a gradient sublimation method under the conditions of a pressure of 2.9 Pa, an argon flow rate of 10.0 mL / min, and a temperature of 235° C. After sublimation purification, 2.7 g of a slightly yellowish white solid was obtained with a recovery rate of 84%.

[0493] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPFA-02 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (manufactured by JASCO Corporation, Model FP-8600) with the toluene solution placed in a quartz cell and measured at room temperature. Furthermore, the emission spectrum was measured using a fluorescence spectrophotometer (manufactured by Hamamatsu Photonics, FS920) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 15The measurement results of the obtained absorption spectrum and emission spectrum are shown. The horizontal axis indicates the wavelength, and the vertical axis indicates the absorbance and the emission intensity. Further, in Figure 15 the two solid lines, the thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. Figure 15 The absorbance shown indicates the result obtained by subtracting the absorption spectrum measured by placing toluene alone in a quartz cell from the absorption spectrum measured by placing a toluene solution in a quartz cell.

[0494] As shown in Figure 15 mmtBumTPFA-02 has an emission peak at 395 nm.

[0495] Next, the mmtBumTPFA-02 obtained in this example was analyzed by liquid chromatography mass spectrometry (abbreviated as: LC / MS analysis).

[0496] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0497] In the LC separation, an arbitrary column was used, the column temperature was 40°C, and the elution conditions were as follows: a solvent was appropriately selected, mmtBumTPFA-02 of an arbitrary concentration was dissolved in an organic solvent to adjust the sample, and the injection amount was 5.0 μL.

[0498] MS analysis of the ion derived from mmtBumTPFA-02 at m / z = 738.50 was performed by the PRM method. 2 The PRM was set as follows: the mass range of the target ion was m / z = 738.50 ± 2.0 (isolation window = 4); the detection was performed in the positive mode. The measurement was performed with the energy NCE (Normalized Collision Energy) for accelerating the target ion in the collision cell set to 60. Figure 16 The obtained MS spectrum is shown.

[0499] Figure 17 The results of measuring the refractive index of mmtBumTPFA-02 by a spectroscopic ellipsometer (M-2000U manufactured by J. A. Woollam Japan) are shown. In the measurement, a film obtained by forming the material of each layer on a quartz substrate by a vacuum deposition method at a thickness of about 50 nm was used. Further, the ordinary ray refractive index n,ordinary and the extraordinary ray refractive index n,Extra-ordinary are described in the figure.

[0500] As can be seen from the attached figure, the ordinary refractive index of light in the entire blue light-emitting area of ​​mmtBumTPFA-02 (wavelength above 455nm and below 465nm) is 1.68, which is within the range of above 1.50 and below 1.75. The ordinary refractive index of light at a wavelength of 633nm is also 1.63, which is within the range of above 1.45 and below 1.70. It can be seen that mmtBumTPFA-02 is a material with a low refractive index.

[0501] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPFA-02 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that mmtBumTPFA-02 had a Tg of 109°C.

[0502] Example 2

[0503] "Synthesis Example 2"

[0504] In this example, a method for synthesizing the aromatic amine compound N-(1,1'-biphenyl-4-yl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPFBi-02), which is one embodiment of the present invention shown in Embodiment 1, is described. The structure of mmtBumTPFBi-02 is shown below.

[0505] [Chemical Formula 44]

[0506]

[0507] <Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl>

[0508] The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0509] <Step 2: Synthesis of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0510] The synthesis was carried out in the same manner as in step 2 of Synthesis Example 1.

[0511] <Step 3: Synthesis of 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl>

[0512] The synthesis was carried out in the same manner as in step 3 of Synthesis Example 1.

[0513] <Step 4: Synthesis of mmtBumTPFBi-02>

[0514] 3.0 g (5.6 mmol) of 3-bromo-3", 5,5', 5"-tetra-tert-butyl-1,1':3',1"-terphenyl obtained in step 3, 2.0 g (5.6 mmol) of 2-(4-biphenyl)amino-9,9-dimethylfluorene, 1.6 g (16.8 mmol) of sodium tert-butoxide, and 28 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 64 mg (0.11 mmol) of bis(dibenzylideneacetone)palladium (0), 138 mg (0.34 mmol) of 2-dicyclohexylphosphino-2'-thiazolinone were added. , 6'-dimethoxybiphenyl, and heat the mixture at 120°C for about 8 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash it with toluene. Concentrate the filtrate, and purify the obtained toluene solution by silica gel column chromatography. Concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, and dry the obtained solid under reduced pressure at about 80°C to obtain 3.5 g of the target white solid with a yield of 77%. In addition, the following formula shows the synthesis scheme of step 4.

[0515] [Chemical Formula 45]

[0516]

[0517] Figure 18A and Figure 18B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained by the above steps. Note that Figure 18B It is magnified Figure 18A The graph shows the range of 7.0 ppm to 8.0 ppm in . Furthermore, the numerical data are shown below. From this, it can be seen that N-(1,1'-biphenyl-4-yl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine can be synthesized.

[0518] 1H-NMR.δ (CDCl3): 7.65 (d, 1H, J=7.4Hz), 7.61 (s, 1H), 7.58-7.60 (m, 2H), 7.49-7.51 (m, 4H), 7.47 (dd, 1H, J=1.7Hz), 7.38-7.43(m,6H),7.23-7.25(m,2H),7.14(dd,1H,J=1.7Hz),1.44(s,6H),1.39(s,9H),1.34(s,18H),1.31(s,9H).

[0519] Next, 3.5 g of the obtained white solid was purified by sublimation using a gradient sublimation method under the conditions of a pressure of 2.6 Pa, an argon flow rate of 10.0 mL / min, and a temperature of 255° C. After sublimation purification, 2.9 g of a white solid was obtained with a recovery rate of 83%.

[0520] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPFBi-02 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (manufactured by JASCO Corporation, Model FP-8600) with the toluene solution placed in a quartz cell and measured at room temperature. Furthermore, the emission spectrum was measured using a fluorescence spectrophotometer (manufactured by Hamamatsu Photonics, FS920) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 19 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 19 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 19 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0521] like Figure 19 As shown, mmtBumTPFBi-02 has a luminescence peak at 392 nm.

[0522] Next, the mmtBumTPFBi-02 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0523] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0524] In LC separation, an arbitrary column was used, the column temperature was 40° C., and the injection conditions were as follows: a solvent was appropriately selected, mmtBumTPFBi-02 was dissolved in an organic solvent at an arbitrary concentration to prepare the sample, and the injection volume was 5.0 μL.

[0525] MS of the ion m / z = 814.53 derived from mmtBumTPFBi-02 was performed using the PRM method. 2 Measurement. PRM settings were as follows: target ion mass range m / z = 814.53 ± 2.0 (isolation window = 4); detection in positive mode; and measurement with the target ion acceleration energy NCE (Normalized Collision Energy) set to 50 in the collision cell. Figure 20 The obtained MS spectrum is shown.

[0526] Figure 21 The figures show the refractive index of mmtBumTPFBi-02 measured using a spectroscopic ellipsometer (M-2000U, manufactured by JA Woollam Japan). The measurements were performed using a film formed on a quartz substrate by vacuum deposition to a thickness of approximately 50 nm, with each layer of material deposited. The figures also show the ordinary and extraordinary refractive indices, n,ordinary and n,extra-ordinary, respectively.

[0527] As can be seen from the attached figure, the ordinary light refractive index of light in the entire blue light-emitting area of ​​mmtBumTPFBi-02 (wavelength above 455nm and below 465nm) is 1.71 to 1.72, which is within the range of above 1.50 and below 1.75. The ordinary light refractive index of light at a wavelength of 633nm is also 1.65, which is within the range of above 1.45 and below 1.70. It can be seen that mmtBumTPFBi-02 is a material with a low refractive index.

[0528] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPFBi-02 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that mmtBumTPFBi-02 had a Tg of 126°C.

[0529] Example 3

[0530] "Synthesis Example 3"

[0531] In the present embodiment, a method for synthesizing the arylamine compound 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: mmtBumTPoFBi-02) of one embodiment of the present application shown in Embodiment Mode 1 will be described. The structure of mmtBumTPoFBi-02 is shown below.

[0532] [Chemical Formula 46]

[0533]

[0534] <Step 1: Synthesis of 3-bromo-3',5,5'-tris-tert-butylbiphenyl>

[0535] Synthesized in the same manner as in Step 1 of Synthesis Example 1.

[0536] <Step 2: Synthesis of 2-(3',5,5'-tris-tert-butyl[l,l'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborinane>

[0537] Synthesized in the same manner as in Step 2 of Synthesis Example 1.

[0538] <Step 3: Synthesis of 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl>

[0539] Synthesized in the same manner as in Step 3 of Synthesis Example 1.

[0540] <Step 4: Synthesis of mmtBumTPoFBi-02>

[0541] 5.8 g (10.9 mmol) of 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl obtained in step 3, 3.9 g (10.9 mmol) of N-(1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine, 3.1 g (32.7 mmol) of sodium tert-butoxide, and 55 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 64 mg (0.11 mmol) of bis(dibenzylideneacetone)palladium(0) and 132 mg (0.65 mmol) of bis(dibenzylideneacetone)palladium(0) were added. tri-tert-butylphosphine, and heat the mixture at 80°C for about 2 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash with toluene. Concentrate the filtrate, and purify the obtained toluene solution by silica gel column chromatography. Concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, and dry the obtained solid under reduced pressure at about 80°C to obtain 8.1 g of the target product as a white solid with a yield of 91%. In addition, the following formula shows the synthesis scheme of mmtBumTPoFBi-02.

[0542] [Chemical Formula 47]

[0543]

[0544] Figure 22A and Figure 22B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white powder obtained by the above steps. Note that Figure 22B It is magnified Figure 22A The graph shows the range of 6.5 ppm to 8.0 ppm in . Furthermore, the numerical data are shown below. From this, it can be seen that 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 can be synthesized.

[0545] 1H-NMR.δ (CDCl3): 7.56 (d, 1H, J=7.4Hz), 7.50 (dd, 1H, J=1.7Hz), 7.33-7.46 (m, 11H), 7.27-7.29 (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).

[0546] Next, 8.0 g of the obtained white solid was purified by sublimation using a gradient sublimation method under the conditions of a pressure of 3.4 Pa, an argon flow rate of 15.0 mL / min, and a temperature of 260° C. After sublimation purification, 7.1 g of a slightly yellowish white solid was obtained with a recovery rate of 89%.

[0547] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPoFBi-02 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (manufactured by JASCO Corporation, Model FP-8600) with the toluene solution placed in a quartz cell and measured at room temperature. Furthermore, the emission spectrum was measured using a fluorescence spectrophotometer (manufactured by Hamamatsu Photonics, FS920) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 23 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 23 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 23 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0548] like Figure 23 As shown, mmtBumTPoFBi-02 has a luminescence peak at 403 nm.

[0549] Next, the mmtBumTPoFBi-02 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0550] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0551] In LC separation, an arbitrary column was used, the column temperature was 40° C., and the injection conditions were as follows: a solvent was appropriately selected, mmtBumTPoFBi-02 was dissolved in an organic solvent to prepare the sample at an injection volume of 5.0 μL.

[0552] MS of the ion m / z = 814.53 derived from mmtBumTPoFBi-02 was performed using the PRM method. 2 Measurements were performed using PRM settings: target ion mass range m / z = 814.53 ± 2.0 (isolation window = 4); detection was performed in positive mode; and the target ion acceleration energy (NCE) in the collision cell was set to 60. Figure 24 The obtained MS spectrum is shown.

[0553] Figure 25 The figures show the refractive index of mmtBumTPoFBi-02 measured using a spectroscopic ellipsometer (M-2000U, manufactured by JA Woollam Japan). The measurements were performed using a film formed on a quartz substrate by vacuum deposition to a thickness of approximately 50 nm, with each layer of material deposited. The figures also show the ordinary and extraordinary refractive indices, n,ordinary and n,extra-ordinary, respectively.

[0554] As can be seen from the accompanying drawings, the ordinary light refractive index of light in the entire blue light-emitting area of ​​mmtBumTPoFBi-02 (wavelength above 455nm and below 465nm) is 1.69 to 1.70, which is within the range of above 1.50 and below 1.75. The ordinary light refractive index of light at a wavelength of 633nm is also 1.64, which is within the range of above 1.45 and below 1.70. It can be seen that mmtBumTPoFBi-02 is a material with a low refractive index.

[0555] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPoFBi-02 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that the Tg of mmtBumTPoFBi-02 was 126°C.

[0556] Example 4

[0557] "Synthesis Example 4"

[0558] In this example, a method for synthesizing the aromatic amine compound N-(4-cyclohexylphenyl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPchPAF-02), which is one embodiment of the present invention shown in Embodiment 1, is described. The structure of mmtBumTPchPAF-02 is shown below.

[0559] [Chemical Formula 48]

[0560]

[0561] <Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl>

[0562] The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0563] <Step 2: Synthesis of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0564] The synthesis was carried out in the same manner as in step 2 of Synthesis Example 1.

[0565] <Step 3: Synthesis of 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl>

[0566] The synthesis was carried out in the same manner as in step 3 of Synthesis Example 1.

[0567] <Step 4: Synthesis of mmtBumTPchPAF-02>

[0568] 3.0 g (5.6 mmol) of 3-bromo-3", 5,5', 5"-tetra-tert-butyl-1,1':3',1"-terphenyl obtained in step 3, 2.1 g (5.6 mmol) of N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine, 1.6 g (16.9 mmol) of sodium tert-butoxide and 28 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 65 mg (0.11 mmol) of bis(dibenzylideneacetone)palladium(0) and 139 mg (0.34 mmol) of 2-dicyclohexylphosphino-2-yl were added. ',6'-dimethoxybiphenyl, and heat the mixture at 80°C for about 2 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash with toluene. Concentrate the filtrate, and purify the obtained toluene solution by silica gel column chromatography. Concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, and dry the obtained solid under reduced pressure at about 80°C to obtain 3.7 g of the target white solid with a yield of 80%. In addition, the following formula shows the synthesis scheme of mmtBumTPchPAF-02.

[0569] [Chemical Formula 49]

[0570]

[0571] Figure 26A and Figure 26B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained by the above steps. Note that Figure 26B It is magnified Figure 26A The graph shows the range of 6.5ppm to 8.0ppm in the present invention. In addition, the numerical data are shown below. As can be seen from this, mmtBumTPchPAF-02 can be synthesized in this synthesis example.

[0572] 1H-NMR.δ (CDCl3): 7.62 (d, 1H, J=7.5Hz), 7.56 (d, 1H, J=8.0Hz), 7.50 (dd, 1H, J=1.7Hz), 7.4 6-7.47(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(dd,1H,J=2.3Hz),2.46(brm,1H),1. 83-1.88(m, 4H), 1.73-1.75(brm, 1H), 1.42(s, 6H), 1.38(s, 9H), 1.36(s, 18H), 1.29(s, 9H)

[0573] Next, 3.5 g of the obtained white solid was purified by sublimation using a gradient sublimation method under the conditions of a pressure of 4.0 Pa, an argon flow rate of 15.0 mL / min, and a temperature of 265° C. After sublimation purification, 3.1 g of a slightly yellowish white solid was obtained with a recovery rate of 89%.

[0574] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPchPAF-02 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (manufactured by JASCO Corporation, Model FP-8600) with the toluene solution placed in a quartz cell and measured at room temperature. Furthermore, the emission spectrum was measured using a fluorescence spectrophotometer (manufactured by Hamamatsu Photonics, FS920) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 27 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 27 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 27 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0575] like Figure 27 As shown, mmtBumTPchPAF-02 has an emission peak at 395 nm.

[0576] Next, the mmtBumTPchPAF-02 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0577] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0578] For LC separation, an arbitrary column was used at a column temperature of 40° C. The injection conditions were as follows: a solvent was appropriately selected, mmtBumTPchPAF-02 was dissolved in an organic solvent at an arbitrary concentration to prepare the sample, and the injection volume was 5.0 μL.

[0579] MS of the ion m / z = 820.58 derived from mmtBumTPchPAF-02 was performed using the PRM method. 2 Measurements were performed using PRM settings: target ion mass range m / z = 820.58 ± 2.0 (isolation window = 4); detection was performed in positive mode; and the target ion acceleration energy (NCE) in the collision cell was set to 60. Figure 28 The obtained MS spectrum is shown.

[0580] Figure 29 The figures show the refractive index of mmtBumTPchPAF-02 measured using a spectroscopic ellipsometer (M-2000U, manufactured by JA Woollam Japan). The measurements were performed using a film formed on a quartz substrate by vacuum deposition to a thickness of approximately 50 nm, with each layer of material deposited. The figures also show the ordinary and extraordinary refractive indices, n,ordinary and n,extra-ordinary, respectively.

[0581] As can be seen from the accompanying drawings, the ordinary light refractive index of light in the entire blue light-emitting area of ​​mmtBumTPchPAF-02 (wavelength above 455nm and below 465nm) is 1.67 to 1.68, which is within the range of above 1.50 and below 1.75. The ordinary light refractive index of light at a wavelength of 633nm is also 1.62, which is within the range of above 1.45 and below 1.70. It can be seen that mmtBumTPchPAF-02 is a material with a low refractive index.

[0582] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPchPAF-02 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that mmtBumTPchPAF-02 had a Tg of 127°C.

[0583] Example 5

[0584] "Synthesis Example 5"

[0585] In this example, a method for synthesizing the aromatic amine compound N-(1,1'-biphenyl-2-yl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPoFBi-03), which is one embodiment of the present invention shown in Embodiment 1, is described. The structure of mmtBumTPoFBi-03 is shown below.

[0586] [Chemical Formula 50]

[0587]

[0588] <Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl>

[0589] The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0590] <Step 2: Synthesis of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0591] The synthesis was carried out in the same manner as in step 2 of Synthesis Example 1.

[0592] <Step 3: Synthesis of 3-bromo-3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl>

[0593] 10.0 g (22.3 mmol) of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane obtained in Step 2, 12.8 g (26.8 mmol) of 1-bromo-3-iodobenzene, 9.2 g (66.9 mmol) of potassium carbonate, 112 mL of toluene, 45 mL of ethanol, and 33 mL of tap water were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen. 100 mg (0.44 mmol) of palladium acetate and 233 mg (0.89 mmol) of triphenylphosphine were added, and the mixture was heated at 80°C for approximately 10 hours. The flask was then allowed to return to room temperature, and the organic and aqueous layers were separated. Magnesium sulfate was added to the solution to remove moisture and concentrate it. The hexane solution of the obtained solution was purified by silica gel column chromatography to obtain 9.4 g of the target compound as a white solid in a yield of 89%. The following formula shows the synthesis scheme of Step 3.

[0594] [Chemical Formula 51]

[0595]

[0596] <Step 4: Synthesis of mmtBumTPoFBi-03>

[0597] 4.0 g (8.4 mmol) of 3-bromo-3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl obtained in step 3, 3.0 g (8.4 mmol) of N-(1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine, 2.4 g (25.2 mmol) of sodium tert-butoxide and 42 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 97 mg (0.17 mmol) of bis(dibenzylideneacetone)palladium(0) and 207 mg (0.50 mmol) of 2 -dicyclohexylphosphino-2',6'-dimethoxybiphenyl, heat the mixture at 80°C for about 2 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash it with toluene. Concentrate the filtrate, and purify the obtained toluene solution by silica gel column chromatography. Concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, dry the obtained solid under reduced pressure at about 80°C, and obtain 3.6 g of the target white solid with a yield of 56%. The following formula shows the synthesis scheme of step 4.

[0598] [Chemical Formula 52]

[0599]

[0600] Figure 30A and Figure 30B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained by the above steps. Note that Figure 30B It is magnified Figure 30A The graph shows the range of 6.5 ppm to 8.0 ppm in . Furthermore, the numerical data are shown below. From this, it can be seen that N-(1,1'-biphenyl-2-yl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine can be synthesized.

[0601] 1 H-NMR. δ (CDCl3): 7.55 (d, 1H, J=7.4Hz), 7.50 (dd, 1H, J=1.7Hz), 7.42-7.43 (m, 3H), 7.27-7.39 (m, 10H), 7.18-7.25 (m, 4H), 7.00-7.12 (m, 4H), 6.97 (dd, 1H, J = 6.3Hz, 1.7Hz), 6.93 (d, 1H, J = 1.7Hz), 6.82 (dd, 1H, J = 7.3Hz, 2.3Hz), 1.37 (s, 9H), 1.36 (s, 18H), 1.29 (s, 6H).

[0602] Next, 3.6 g of the obtained white solid was purified by sublimation using a gradient sublimation method under the conditions of a pressure of 2.3 Pa, an argon flow rate of 15.0 mL / min, and a temperature of 250° C. After sublimation purification, 3.1 g of a slightly yellowish white solid was obtained with a recovery rate of 86%.

[0603] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPoFBi-03 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (manufactured by JASCO Corporation, Model FP-8600) with the toluene solution placed in a quartz cell and measured at room temperature. Furthermore, the emission spectrum was measured using a fluorescence spectrophotometer (manufactured by Hamamatsu Photonics, Model FS920) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 31 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 31 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 31The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0604] like Figure 31 As shown, mmtBumTPoFBi-03 has a luminescence peak at 403 nm.

[0605] Next, the mmtBumTPoFBi-03 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0606] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0607] In LC separation, an arbitrary column was used, the column temperature was 40° C., and the injection conditions were as follows: a solvent was appropriately selected, mmtBumTPoFBi-03 was dissolved in an organic solvent at an arbitrary concentration to prepare the sample, and the injection volume was 5.0 μL.

[0608] MS of the ion m / z = 758.47 derived from mmtBumTPoFBi-03 was performed using the PRM method. 2 Measurement. PRM settings were: target ion mass range m / z = 758.47 ± 2.0 (isolation window = 4); detection in positive mode. Measurement was performed with the NCE (Normalized Collision Energy) energy used to accelerate the target ion in the collision cell set to 50. Figure 32 The obtained MS spectrum is shown.

[0609] Figure 33 The figures show the refractive index of mmtBumTPoFBi-03 measured using a spectroscopic ellipsometer (M-2000U, manufactured by JA Woollam Japan). The measurements were performed using a film formed on a quartz substrate by vacuum deposition to a thickness of approximately 50 nm, with each layer of material deposited. The figures also show the ordinary and extraordinary refractive indices, n,ordinary and n,extra-ordinary, respectively.

[0610] As can be seen from the accompanying drawings, the ordinary light refractive index of light in the entire blue light-emitting area of ​​mmtBumTPoFBi-03 (wavelength above 455nm and below 465nm) is 1.69 to 1.70, which is within the range of above 1.50 and below 1.75. The ordinary light refractive index of light at a wavelength of 633nm is also 1.64, which is within the range of above 1.45 and below 1.70. It can be seen that mmtBumTPoFBi-03 is a material with a low refractive index.

[0611] Example 6

[0612] "Synthesis Example 6"

[0613] In this example, a method for synthesizing the aromatic amine compound N-(4-cyclohexylphenyl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPchPAF-03), which is one embodiment of the present invention shown in Embodiment 1, is described. The structure of mmtBumTPchPAF-03 is shown below.

[0614] [Chemical Formula 53]

[0615]

[0616] <Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl>

[0617] The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0618] <Step 2: Synthesis of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0619] The synthesis was carried out in the same manner as in step 2 of Synthesis Example 1.

[0620] <Step 3: Synthesis of 3-bromo-3",5,5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl>

[0621] The synthesis was carried out in the same manner as in step 3 of Synthesis Example 1.

[0622] <Step 4: Synthesis of mmtBumTPchPAF-03>

[0623] 2.3 g (4.8 mmol) of 3-bromo-3", 5', 5"-tri-tert-butyl-1,1':3', 1"-terphenyl obtained by step 3, 1.8 g (4.8 mmol) of N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine, 1.4 g (14.4 mmol) of sodium tert-butoxide and 24 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 55 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium (0) and 118 mg (0.29 mmol) of 2-dimethyl-1,1':3',1"-terphenyl were added. Cyclohexylphosphino-2',6'-dimethoxybiphenyl, heat the mixture at 80°C for about 2 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash with toluene. Concentrate the filtrate, and purify the obtained toluene solution by silica gel column chromatography. Concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, dry the obtained solid under reduced pressure at about 80°C, and obtain 2.9 g of the target white solid with a yield of 80%. The following formula shows the synthesis scheme of step 4.

[0624] [Chemical Formula 54]

[0625]

[0626] Figure 34A and Figure 34B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained by the above steps. Note that Figure 34B It is magnified Figure 34A The graph shows the range of 6.5 ppm to 8.0 ppm in . Furthermore, the numerical data are shown below. From this, it can be seen that N-(4-cyclohexylphenyl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine can be synthesized.

[0627] 1H-NMR.δ (CDCl3): 7.62 (d, 1H, J = 7.5Hz), 7.56 (d, 1H, J = 8.6Hz), 7.51 (dd, 1H, J = 1.7 Hz),7.48(dd,1H,J=1.7Hz),7.46(dd,1H,J=1.7Hz),7.42(dd,1H,J=1.7Hz),7.37-7 .39(m,4H),7.27-7.33(m,2H),7.23-7.25(m,2H),7.05-7.13(m,7H),2.46(brm,1H ),1.83-1.90(m,4H),1.73-1.75(brm,1H),1.41(s,6H),1.37(s,9H),1.35(s,18H).

[0628] Next, 2.4 g of the obtained white solid was purified by sublimation using a gradient sublimation method under the conditions of a pressure of 4.0 Pa, an argon flow rate of 15.0 mL / min, and a temperature of 230° C. After sublimation purification, 1.9 g of a slightly yellowish white solid was obtained with a recovery rate of 79%.

[0629] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPchPAF-03 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (manufactured by JASCO Corporation, Model FP-8600) with the toluene solution placed in a quartz cell and measured at room temperature. Furthermore, the emission spectrum was measured using a fluorescence spectrophotometer (manufactured by Hamamatsu Photonics, Model FS920) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 35 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 35 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 35 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0630] like Figure 35 As shown, mmtBumTPchPAF-03 has a luminescence peak at 399 nm.

[0631] Next, the mmtBumTPchPAF-03 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0632] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0633] For LC separation, an arbitrary column was used, the column temperature was 40° C., and the injection conditions were as follows: a solvent was appropriately selected, mmtBumTPchPAF-03 was dissolved in an organic solvent at an arbitrary concentration to prepare the sample, and the injection volume was 5.0 μL.

[0634] MS of the ion m / z = 764.52 derived from mmtBumTPchPAF-03 was performed using the PRM method. 2 Measurement. PRM settings were: target ion mass range m / z = 764.52 ± 2.0 (isolation window = 4); detection in positive mode. Measurement was performed with the NCE (Normalized Collision Energy) energy used to accelerate the target ion in the collision cell set to 50. Figure 36 The obtained MS spectrum is shown.

[0635] Figure 37 The figures show the refractive index of mmtBumTPchPAF-03 measured using a spectroscopic ellipsometer (M-2000U, manufactured by JA Woollam Japan). The measurements were performed using a film formed on a quartz substrate by vacuum deposition to a thickness of approximately 50 nm, with each layer of material deposited. The figures also show the ordinary and extraordinary refractive indices, n,ordinary and n,extra-ordinary, respectively.

[0636] As can be seen from the accompanying drawings, the ordinary light refractive index of light in the entire blue light-emitting area of ​​mmtBumTPchPAF-03 (wavelength above 455nm and below 465nm) is 1.69 to 1.70, which is within the range of above 1.50 and below 1.75. The ordinary light refractive index of light at a wavelength of 633nm is also 1.64, which is within the range of above 1.45 and below 1.70. It can be seen that mmtBumTPchPAF-03 is a material with a low refractive index.

[0637] Example 7

[0638] In this example, a light-emitting device according to one embodiment of the present invention and a comparative light-emitting device described in the embodiment are described. The structural formulas of the organic compounds used in this example are shown below.

[0639] [Chemical Formula 55]

[0640]

[0641] (Method for Manufacturing Light-Emitting Device 1)

[0642] First, an indium tin oxide (ITSO) film containing silicon oxide was formed on a glass substrate by a sputtering method, thereby forming the first electrode 101. Note that the thickness was 55 nm and the electrode area was 2 mm×2 mm.

[0643] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0644] Then, the substrate is placed inside the chamber and the pressure is reduced to 10 -4 The substrate was placed in a vacuum deposition apparatus at a pressure of about 1.5 Pa and vacuum-baked at 170° C. in a heating chamber within the vacuum deposition apparatus for 30 minutes, and then cooled for about 30 minutes.

[0645] Next, the substrate on which the first electrode 101 was formed was fixed on a substrate holder provided in a vacuum evaporation apparatus in a manner such that the surface on which the first electrode 101 was formed faced downward, and N-(4-cyclohexylphenyl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: mmtBumTPchPAF-02) represented by the above-mentioned structural formula (i) and an electron acceptor material (OCHD-001) were co-evaporated on the first electrode 101 by a resistance heating evaporation method in a manner such that the weight ratio of 1:0.1 (=mmtBumTPchPAF-02:OCHD-001) and a thickness of 10 nm were achieved, thereby forming a hole injection layer 111.

[0646] Next, mmtBumTPchPAF-02 is vapor-deposited on the hole injection layer 111 in a thickness of 30 nm, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviated as: DBfBB1TP) represented by the above structural formula (ii) is vapor-deposited in a thickness of 10 nm to form a hole transport layer 112.

[0647] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviated as αN-βNPAnth) represented by the above structural formula (iii) and 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10PCA2Nbf(IV)-02) represented by the above structural formula (iv) are co-evaporated in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) and a thickness of 25 nm, thereby forming a light-emitting layer 113.

[0648] Then, on the light-emitting layer 113, 2-{4-[9,10-di(naphthalene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviated as: ZADN) represented by the above structural formula (v) and 8-hydroxyquinoline lithium (abbreviated as: Liq) represented by the above structural formula (vi) are co-evaporated in a weight ratio of 1:1 (=ZADN:Liq) and a thickness of 25 nm, thereby forming an electron transport layer 114.

[0649] After forming the electron transport layer 114 , Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115 , and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102 , thereby manufacturing the light emitting device 1 of this embodiment.

[0650] (Method for Manufacturing Light-Emitting Device 2)

[0651] In the light-emitting device 2, 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-fluorene-2-amine (abbreviated as: mmtBumTPoFBi-02) represented by the above-mentioned structural formula (vii) is used instead of mmtBumTPchPAF-02 of the light-emitting device 1. Except for this, the light-emitting device 2 is manufactured in the same manner as the light-emitting device 1.

[0652] (Manufacturing Method of Comparative Light-Emitting Device 1)

[0653] In comparative light-emitting device 1, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF) represented by the above-mentioned structural formula (viii) was used instead of mmtBumTPchPAF-02 of light-emitting device 1, and the device was manufactured in the same manner as light-emitting device 1.

[0654] The following table shows the element structures of the above-mentioned light-emitting device and a comparative light-emitting device.

[0655] [Table 1]

[0656]

[0657] Figure 38 The refractive indexes of the low refractive index materials (mmtBumTPchPAF-02 and mmtBumTPoFBi-02) for a part of a hole injection layer, a hole transport layer, and PCBBiF as a reference are shown. Further, the refractive indexes at 458 nm are shown below.

[0658] [Table 2]

[0659] Refractive index mmtBumTPchPAF-02 1.67 mmtBumTPoFBi-02 1.70 PCBBiF 1.94

[0660] In a glove box under a nitrogen atmosphere, the above light emitting devices and comparative light emitting devices were sealed using a glass substrate in such a manner that the devices were not exposed to the atmosphere (a sealing material was applied around the devices, UV treatment was performed at the time of sealing, and heat treatment was performed at a temperature of 80 °C for 1 hour), and the initial characteristics of the light emitting devices were measured. Note that the glass substrate on which the light emitting device was manufactured was not subjected to a special treatment for improving light extraction efficiency.

[0661] Figure 39 The luminance-current density characteristics of the light emitting device 1, the light emitting device 2, and the comparative light emitting device 1 are shown, Figure 40 The current efficiency-luminance characteristics are shown, Figure 41 The luminance-voltage characteristics are shown, Figure 42 The current-voltage characteristics are shown, Figure 43 The external quantum efficiency-luminance characteristics are shown, Figure 44 The emission spectrum is shown. Further, Table 3 shows the main characteristics of each light emitting device at 1000 cd / m 2 Note that the luminance, CIE chromaticity, and emission spectrum were measured at normal temperature using a spectroradiometer (manufactured by TOPCON, UR-UL1R). Further, the external quantum efficiency was calculated using the measured luminance and emission spectrum under the condition that the distribution of light intensity is assumed to be Lambertian.

[0662] [Table 3]

[0663]

[0664] From Figures 39 to 44 As is clear from Table 3, although the shapes of the emission spectrum of the light emitting device of one embodiment of the present application are the same, since it includes a layer using a low refractive index material, it is an EL device whose luminous efficiency is higher than that of the comparative light emitting device.

[0665] Next, Figure 67The current density of the light emitting device 1, the light emitting device 2 and the comparative light emitting device 1 is 50 mA / cm 2 The graph of the brightness change with respect to the driving time when the constant current is driven. Figure 67 As shown, the light-emitting device of one embodiment of the present invention has a long life. As can be seen from this, the light-emitting device of one embodiment of the present invention has high luminous efficiency while maintaining a long life.

[0666] Example 8

[0667] In this example, a light-emitting device according to one embodiment of the present invention and a comparative light-emitting device described in the embodiment are described. The structural formulas of the organic compounds used in this example are shown below.

[0668] [Chemical Formula 56]

[0669]

[0670] (Method for Manufacturing Light-Emitting Device 3)

[0671] First, an indium tin oxide (ITSO) film containing silicon oxide was formed on a glass substrate by a sputtering method, thereby forming the first electrode 101. Note that the thickness was 55 nm and the electrode area was 2 mm×2 mm.

[0672] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0673] Then, the substrate is placed inside the chamber and the pressure is reduced to 10 -4 The substrate was placed in a vacuum deposition apparatus at a pressure of about 1.5 Pa and vacuum-baked at 170° C. in a heating chamber within the vacuum deposition apparatus for 30 minutes, and then cooled for about 30 minutes.

[0674] Next, the substrate on which the first electrode 101 was formed was fixed on a substrate holder provided in a vacuum evaporation apparatus in a manner such that the surface on which the first electrode 101 was formed faced downward, and N-(4-cyclohexylphenyl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-1 ...

[0675] -9,9-Dimethyl-9H-fluoren-2-amine (abbreviated as: mmtBumTPchPAF-03) and electron acceptor material (OCHD-001) were co-evaporated at a weight ratio of 1:0.1 (= mmtBumTPchPAF-03:OCHD-001) and a thickness of 10 nm to form a hole injection layer 111.

[0676] Next, mmtBumTPchPAF-03 is vapor-deposited on the hole injection layer 111 in a thickness of 30 nm, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviated as: DBfBB1TP) represented by the above structural formula (ii) is vapor-deposited in a thickness of 10 nm to form a hole transport layer 112.

[0677] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviated as αN-βNPAnth) represented by the above structural formula (iii) and 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10PCA2Nbf(IV)-02) represented by the above structural formula (iv) are co-evaporated in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) and a thickness of 25 nm, thereby forming a light-emitting layer 113.

[0678] Then, on the light-emitting layer 113, 2-{4-[9,10-di(naphthalene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviated as: ZADN) represented by the above structural formula (v) and 8-hydroxyquinoline lithium (abbreviated as: Liq) represented by the above structural formula (vi) are co-evaporated in a weight ratio of 1:1 (=ZADN:Liq) and a thickness of 25 nm, thereby forming an electron transport layer 114.

[0679] After forming the electron transport layer 114 , Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115 , and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102 , thereby manufacturing the light emitting device 3 of this embodiment.

[0680] (Method for Manufacturing Light-Emitting Device 4)

[0681] In the light-emitting device 4, N-(1,1'-biphenyl-2-yl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBumTPoFBi-03) represented by the above-mentioned structural formula (x) is used instead of mmtBumTPchPAF-03 of the light-emitting device 3. Otherwise, the light-emitting device 4 is manufactured in the same manner as the light-emitting device 1.

[0682] (Manufacturing Method of Comparative Light-Emitting Device 2)

[0683] In comparative light-emitting device 2, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF) represented by the above-mentioned structural formula (viii) was used instead of mmtBumTPchPAF-03 of light-emitting device 3, and the device was manufactured in the same manner as light-emitting device 3.

[0684] The following table shows the element structures of the above-mentioned light-emitting device and a comparative light-emitting device.

[0685] [Table 4]

[0686]

[0687] Figure 45 The refractive indices of low-refractive-index materials (mmtBumTPchPAF-03 and mmtBumTPoFBi-03) used for a portion of the hole injection layer and the hole transport layer, and PCBBiF as a reference are shown. The table below also shows the refractive index at 457 nm.

[0688] [Table 5]

[0689] Refractive index mmtBumTPchPAF-03 1.70 mmtBumTPoFBi-03 1.70 PCBBiF 1.94

[0690] In a nitrogen atmosphere glove box, the aforementioned light-emitting devices and comparative light-emitting devices were sealed using glass substrates to prevent exposure to the atmosphere (a sealing material was applied around the device, UV treatment was performed during sealing, and heat treatment was performed at 80°C for 1 hour). Initial characteristics of these light-emitting devices were then measured. Note that the glass substrates on which the light-emitting devices were fabricated were not subjected to any special treatment to improve light extraction efficiency.

[0691] Figure 46 The luminance-current density characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2 are shown. Figure 47 The current efficiency-luminance characteristics are shown. Figure 48 The brightness-voltage characteristics are shown. Figure 49 Showing the current-voltage characteristics, Figure 50 The external quantum efficiency-luminance characteristics are shown. Figure 51 Table 6 shows the emission spectrum of each light emitting device at 1000 cd / m 2 Key characteristics near the device. Note that luminance, CIE chromaticity, and emission spectra were measured at room temperature using a spectroradiometer (UR-UL1R, manufactured by Topcon). External quantum efficiency was calculated using the measured luminance and emission spectra, assuming a Lambertian light distribution characteristic.

[0692] [Table 6]

[0693]

[0694] from Figures 46 to 51 As can be seen from Table 6, although the shape of the emission spectrum of the light-emitting device of one embodiment of the present invention is substantially the same, since it includes a layer using a low refractive index material, it is an EL device with higher luminous efficiency than the comparative light-emitting device.

[0695] Example 9

[0696] In this example, a light-emitting device according to one embodiment of the present invention and a comparative light-emitting device described in the embodiment are described. The structural formulas of the organic compounds used in this example are shown below.

[0697] [Chemical Formula 57]

[0698]

[0699] (Method for Manufacturing Light-Emitting Device 5)

[0700] First, an indium tin oxide (ITSO) film containing silicon oxide was formed on a glass substrate by a sputtering method, thereby forming the first electrode 101. Note that the thickness was 110 nm and the electrode area was 2 mm×2 mm.

[0701] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0702] Then, the substrate is placed inside the chamber and the pressure is reduced to 10 -4 Pa in a vacuum deposition device, and perform vacuum baking at 170° C. in a heating chamber in the vacuum deposition device for 30 minutes, and then cool the substrate for about 30 minutes.

[0703] Next, the substrate on which the first electrode 101 was formed was fixed on a substrate holder provided in a vacuum evaporation apparatus in a manner such that the surface on which the first electrode 101 was formed faced downward, and N-(4-cyclohexylphenyl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: mmtBumTPchPAF-02) represented by the above-mentioned structural formula (i) and an electron acceptor material (OCHD-001) were co-evaporated on the first electrode 101 by a resistance heating evaporation method in a manner such that the weight ratio of 1:0.1 (=mmtBumTPchPAF-02:OCHD-001) and a thickness of 10 nm were achieved, thereby forming a hole injection layer 111.

[0704] Next, mmtBumTPchPAF-02 was vapor-deposited to a thickness of 50 nm on the hole injection layer 111 to form the hole transport layer 112 .

[0705] Next, 9-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9mDBtBPNfpr) represented by the above structural formula (xi), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as PCBBiF) represented by the above structural formula (viii), and the phosphorescent dopant OCPG-006 are co-evaporated in a weight ratio of 0.6:0.5:0.05 (=9mDBtBPNfpr:PCBBiF:OCPG-006) and a thickness of 40 nm, thereby forming the light-emitting layer 113.

[0706] Then, 9mDBtBPNfpr is evaporated on the light-emitting layer 113 in a thickness of 30 nm, and then 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as: NBPhen) represented by the above structural formula (xii) is evaporated in a thickness of 15 nm to form the electron transport layer 114.

[0707] After forming the electron transport layer 114, lithium fluoride (LiF) is evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum is evaporated to a thickness of 200 nm to form the second electrode 102, thereby manufacturing the light-emitting device 5 of this embodiment.

[0708] (Method for Manufacturing Light-Emitting Device 6)

[0709] In the light-emitting device 6, 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-fluorene-2-amine (abbreviation: mmtBumTPoFBi-02) represented by the above-mentioned structural formula (vii) is used instead of mmtBumTPchPAF-02 of the light-emitting device 5. Other than this, the light-emitting device is manufactured in the same manner as the light-emitting device 5.

[0710] (Method for Manufacturing Light-Emitting Device 7)

[0711] In light-emitting device 7, N-(4-cyclohexylphenyl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: mmtBumTPchPAF-03) represented by the above-mentioned structural formula (ix) is used instead of mmtBumTPchPAF-02 of light-emitting device 5. Other than this, the light-emitting device is manufactured in the same manner as light-emitting device 5.

[0712] (Method for Manufacturing Light-Emitting Device 8)

[0713] In the light-emitting device 8, N-(1,1'-biphenyl-2-yl)-N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBumTPoFBi-03) represented by the above-mentioned structural formula (x) is used instead of mmtBumTPchPAF-02 of the light-emitting device 5. Other than this, the light-emitting device is manufactured in the same manner as the light-emitting device 5.

[0714] (Manufacturing Method of Comparative Light-Emitting Device 3)

[0715] Comparative light-emitting device 3 was manufactured in the same manner as light-emitting device 5 except that PCBBiF was used instead of mmtBumTPchPAF-02 in light-emitting device 5.

[0716] The following table shows the element structures of the above-mentioned light-emitting device and a comparative light-emitting device.

[0717] [Table 7]

[0718]

[0719] *1 Light emitting device 5: mmtBumTPchPAF-02

[0720] Light-emitting device 6: mmtBumTPoFBi-02

[0721] Light emitting device 7: mmtBumTPchPAF-03

[0722] Light emitting device 8: mmtBumTPoFBi-03

[0723] Comparison Light Emitting Device 3: PCBBiF

[0724] Figure 52The refractive indices of low-refractive-index materials (mmtBumTPchPAF-02, mmtBumTPoFBi-02, mmtBumTPchPAF-03, and mmtBumTPoFBi-03) used for a portion of the hole injection layer and the hole transport layer, and PCBBiF as a reference are shown. The table below also shows the refractive index at 629 nm.

[0725] [Table 8]

[0726] Refractive index mmtBumTPchPAF-02 1.62 mmtBumTPoFBi-02 1.64 mmtBumTPchPAF-03 1.64 mmtBumTPoFBi-03 1.64 PCBBiF 1.81

[0727] In a nitrogen atmosphere glove box, the aforementioned light-emitting devices and comparative light-emitting devices were sealed using glass substrates to prevent exposure to the atmosphere (a sealing material was applied around the device, UV treatment was performed during sealing, and heat treatment was performed at 80°C for 1 hour). Initial characteristics of these light-emitting devices were then measured. Note that the glass substrates on which the light-emitting devices were fabricated were not subjected to any special treatment to improve light extraction efficiency.

[0728] Figure 53 The luminance-current density characteristics of the light-emitting devices 5 to 8 and the comparative light-emitting device 3 are shown. Figure 54 The current efficiency-luminance characteristics are shown. Figure 55 The brightness-voltage characteristics are shown. Figure 56 Showing the current-voltage characteristics, Figure 57 The external quantum efficiency-luminance characteristics are shown. Figure 58 Table 9 shows the emission spectrum of each light emitting device at 1000 cd / m 2 Key characteristics near the device. Note that luminance, CIE chromaticity, and emission spectra were measured at room temperature using a spectroradiometer (UR-UL1R, manufactured by Topcon). External quantum efficiency was calculated using the measured luminance and emission spectra, assuming a Lambertian light distribution characteristic.

[0729] [Table 9]

[0730]

[0731] from Figures 53 to 58 As can be seen from Table 9, although the shape of the emission spectrum of the light-emitting device of one embodiment of the present invention is roughly the same, since it includes a layer using a low refractive index material, it is an EL device with higher luminous efficiency than the comparative light-emitting device.

[0732] Example 10

[0733] In this example, a light-emitting device according to one embodiment of the present invention and a comparative light-emitting device described in the embodiment are described. The structural formulas of the organic compounds used in this example are shown below.

[0734] [Chemical Formula 58]

[0735]

[0736] (Method for manufacturing light emitting device 9)

[0737] First, an alloy film of silver (Ag), palladium (Pd), and copper (Cu) (Ag-Pd-Cu (APC) film) was formed on a glass substrate by a sputtering method at a thickness of 100 nm as a reflective electrode, and then indium tin oxide containing silicon oxide (ITSO) was formed by a sputtering method at a thickness of 85 nm as a transparent electrode to form the first electrode 101. Note that the electrode area thereof was 4 mm 2 (2 mm x 2 mm).

[0738] Next, as a pretreatment for forming a light emitting device on a substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0739] Then, the substrate was placed in a vacuum evaporation device whose inside was reduced to a pressure of about 10 -4 Pa, and vacuum baking was performed at a temperature of 170°C for 30 minutes in a heating chamber in the vacuum evaporation device, and then the substrate was cooled for about 30 minutes.

[0740] Next, the substrate on which the first electrode 101 was formed was fixed on a substrate holder provided in the vacuum evaporation device in a manner such that the surface on which the first electrode 101 was formed faced downward, and co-evaporation was performed on the first electrode 101 by an evaporation method in a manner such that the weight ratio of N-(4-cyclohexylphenyl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: mmtBumTPchPAF-02) and the electron acceptor material (OCHD-001) represented by Structural Formula (i) above was 1:0.05 (= mmtBumTPchPAF-02: OCHD-001) and the thickness was 10 nm, whereby the hole injection layer 111 was formed.

[0741] On the hole injection layer 111, mmtBumTPchPAF-02 was evaporated as the first hole transport layer in a manner such that the thickness was 35 nm, and then N,N-bis[4-(dibenzo[f,h]furan-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) represented by Structural Formula (ii) above was evaporated as the second hole transport layer in a manner such that the thickness was 10 nm, whereby the hole transport layer 112 was formed.

[0742] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviated as αN-βNPAnth) represented by the above structural formula (iii) and 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10PCA2Nbf(IV)-02) represented by the above structural formula (iv) are co-evaporated in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10PCA2Nbf(IV)-02) and a thickness of 25 nm, thereby forming a light-emitting layer 113.

[0743] Then, on the light-emitting layer 113, 2-{4-[9,10-di(naphthalene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviated as: ZADN) represented by the above structural formula (v) and 8-hydroxyquinoline lithium (abbreviated as: Liq) represented by the above structural formula (vi) are co-evaporated in a weight ratio of 1:1 (=ZADN:Liq) and a thickness of 25 nm, thereby forming an electron transport layer 114.

[0744] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 115, and silver (Ag) and magnesium (Mg) were co-evaporated to a thickness of 15 nm at a volume ratio of 10:1 to form the second electrode 102, thereby manufacturing the light-emitting element 9. Note that the second electrode 102 is a semi-transmissive and semi-reflective electrode that has the function of reflecting light and transmitting light. The light-emitting device of this embodiment is a top-emitting element that extracts light from the second electrode 102. In addition, 1,3,5-tris(dibenzothiophen-4-yl)-benzene (abbreviated as DBT3P-II) represented by the above-mentioned structural formula (xi) was evaporated to a thickness of 70 nm on the second electrode 102 to improve light extraction efficiency.

[0745] (Method of Manufacturing Light-Emitting Device 10)

[0746] In the light-emitting device 10, 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-fluorene-2-amine (abbreviated as: mmtBumTPoFBi-02) represented by the above-mentioned structural formula (vii) is used instead of mmtBumTPchPAF-02 of the light-emitting device 9. Otherwise, the light-emitting device 10 is manufactured in the same manner as the light-emitting device 9.

[0747] (Manufacturing Method of Comparative Light-Emitting Device 4)

[0748] In the comparative light-emitting device 4, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) represented by the above structural formula (viii) was used instead of mmtBumTPchPAF-02 of the light-emitting device 9, and the thickness of the first hole-transport layer was 30 nm, and the light-emitting device 9 was manufactured in the same manner except for these.

[0749] The following shows the element structures of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4.

[0750] [Table 10]

[0751]

[0752] *2The light-emitting device 9, the light-emitting device 10: 35 nm, the comparative light-emitting device 4: 30 nm

[0753] Figure 59 The refractive indexes of the low-refractive materials (mmtBumTPchPAF-02 and mmtBumTPoFBi-02) used for a part of the hole-injection layer and the hole-transport layer, and PCBBiF as a reference are shown, and the following shows the refractive indexes at 458 nm.

[0754] [Table 11]

[0755] Refractive index mmtBumTPchPAF-02 1.67 mmtBumTPoFBi-02 1.70 PCBBiF 194

[0756] In a glove box under a nitrogen atmosphere, the above light-emitting devices and the comparative light-emitting device were sealed with a glass substrate in such a manner that the devices were not exposed to the air (a sealing material was applied to the periphery of the device, and UV treatment was performed at the time of sealing), and the initial characteristics of these light-emitting devices were measured. Note that the glass substrate subjected to the sealing treatment was not subjected to a special treatment for improving light extraction efficiency.

[0757] Figure 60 The luminance-current density characteristics of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4 are shown, Figure 61 The current efficiency-luminance characteristics are shown, Figure 62 The luminance-voltage characteristics are shown, Figure 63 The current-voltage characteristics are shown, Figure 64 The blue index-luminance characteristics are shown, Figure 65 The emission spectra are shown. In addition, Table 12 shows the main characteristics of each light-emitting device at 1000 cd / m 2 at room temperature using a spectroradiometer (Topcon Corporation, SR-UL1R). Note that the luminance, the CIE chromaticity coordinates, and the emission spectrum were measured using a spectroradiometer (Topcon Corporation, SR-UL1R) at room temperature.

[0758] [Table 12]

[0759]

[0760] from Figures 60 to 65 As can be seen from Table 12, the light-emitting device using the low-refractive-index material according to one embodiment of the present invention is an EL device having better current efficiency and blue index (BI) than the comparative light-emitting device.

[0761] Note that the blue index (BI) refers to the value obtained by dividing the current efficiency (cd / A) by the chromaticity y, and is one of the indicators that represent the luminous characteristics of blue light. The smaller the chromaticity y, the higher the color purity of blue light. Blue light with high color purity can present a wider range of blue even if it has a small brightness component. When blue light with high color purity is used, the brightness required to present blue is reduced, thereby achieving the effect of reducing power consumption. Therefore, the BI of chromaticity y, one of the indicators of blue purity, is appropriately used as a method of representing the efficiency of blue light. It can be said that the higher the BI of the light-emitting device, the better the efficiency of the blue light-emitting device as a display.

[0762] then, Figure 66 The current density of the light emitting device 9, the light emitting device 10 and the comparative light emitting device 4 is 50 mA / cm 2 The graph of the brightness change with respect to the driving time when the constant current is driven. Figure 66 As shown, it can be seen that the light-emitting device according to one embodiment of the present invention is a light-emitting device having high luminous efficiency while maintaining a long life.

[0763] Example 11

[0764] In this example, a light-emitting device according to one embodiment of the present invention and a comparative light-emitting device described in the embodiment are described. The structural formulas of the organic compounds used in this example are shown below.

[0765] [Chemical Formula 59]

[0766]

[0767] (Method for Manufacturing Light-Emitting Device 11)

[0768] First, a silver (Ag) film was formed on a glass substrate by sputtering to a thickness of 100 nm as a reflective electrode, and then indium tin oxide (ITSO) containing silicon oxide was formed by sputtering to a thickness of 10 nm as a transparent electrode to form the first electrode 101. Note that the electrode area is 4 mm 2 (2mm×2mm).

[0769] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0770] Then, the substrate is placed inside the chamber and the pressure is reduced to 10 -4 The substrate was placed in a vacuum deposition apparatus at a pressure of about 1.5 Pa and vacuum-baked at 170° C. in a heating chamber within the vacuum deposition apparatus for 30 minutes, and then cooled for about 30 minutes.

[0771] Next, the substrate on which the first electrode 101 is formed is fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 is formed faces downward, and N-(4-cyclohexylphenyl)-N-(3,3",5',5"-tetra-tert-butyl-1,1':3',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: mmtBumTPchPAF-02) represented by the above-mentioned structural formula (i) and the electron acceptor material (OCHD-001) are co-evaporated on the first electrode 101 by a vapor deposition method in a weight ratio of 1:0.1 (=mmtBumTPchPAF-02:OCHD-001) and a thickness of 10 nm, thereby forming a hole injection layer 111.

[0772] On the hole injection layer 111, mmtBumTPchPAF-02 is evaporated in a thickness of 125 nm as a first hole transport layer, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviated as: DBfBB1TP) represented by the above structural formula (ii) is evaporated in a thickness of 10 nm as a second hole transport layer to form a hole transport layer 112.

[0773] Next, 3,3′-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviated as PCzN 2 ) represented by the above structural formula (xii) was deposited on the hole transport layer 112 to a thickness of 10 nm to form an electron blocking layer.

[0774] Then, 2-(10-phenyl-9-anthracenyl)-benzo[b]naphtho[2,3-d]furan (abbreviated as: Bnf(II)PhA) represented by the above structural formula (xiii) and 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as: 3,10PCA2Nbf(IV)-02) represented by the above structural formula (iv) are co-evaporated in a weight ratio of 1:0.015 (=Bnf(II)PhA:3,10PCA2Nbf(IV)-02) and a thickness of 25 nm, thereby forming the light-emitting layer 113.

[0775] Then, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xiv) was formed over the light-emitting layer 113 at a thickness of 10 nm as a hole-blocking layer, and co-evaporation was performed at a weight ratio of 1:1 (= mPn-mDMePyPTzn: Liq) of 2-[3-(2,6-dimethyl-3-pyridyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) and 8-hydroxyquinoline-lithium (abbreviation: Liq) represented by the above structural formula (vi) at a thickness of 20 nm, whereby the electron-transport layer 114 was formed.

[0776] After the formation of the electron-transport layer 114, lithium fluoride (LiF) was deposited over the electron-transport layer 114 at a thickness of 1 nm to form an electron-injection layer 115, and silver (Ag) and magnesium (Mg) were co-deposited at a thickness of 15 nm and at a volume ratio of 10:1 to form a second electrode 102, whereby the light-emitting element 11 was manufactured. Note that the second electrode 102 is a semi-transmissive and semi-reflective electrode having a function of reflecting light and a function of transmitting light, and the light-emitting device of this embodiment is a top emission element from which light is extracted from the second electrode 102. In addition, 1,3,5-tris(dibenzothiophene-4-yl)-benzene (abbreviation: DBT3P-II) represented by the above structural formula (xi) was deposited over the second electrode 102 at a thickness of 70 nm to improve the light extraction efficiency.

[0777] (Method for manufacturing light-emitting device 12)

[0778] In the light-emitting device 12, 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: mmtBumTPoFBi-02) represented by the above structural formula (vii) was used instead of mmtBumTPchPAF-02 of the light-emitting device 11, and the thickness of the first hole-transport layer was 130 nm, and the light-emitting device 12 was manufactured in the same manner as the light-emitting device 11 except for these.

[0779] (Method for manufacturing comparative light-emitting device 5)

[0780] In the comparative light-emitting device 5, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) represented by the above structural formula (viii) was used instead of mmtBumTPchPAF-02 of the light-emitting device 11, and the thickness of the first hole-transport layer was 100 nm, and the light-emitting device 5 was manufactured in the same manner as the light-emitting device 11 except for these.

[0781] The following shows the element structures of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5.

[0782] [Table 13]

[0783]

[0784] *3Light-emitting device 11: 125 nm, light-emitting device 12: 130 nm, comparative light-emitting device 5: 100 nm

[0785] Figure 68 The refractive indexes of the low-refractive materials (mmtBumTPchPAF-02 and mmtBumTPoFBi-02) used for a part of the hole-injection layer and the hole-transport layer, and PCBBiF as a reference are shown, and the following shows the refractive indexes at 458 nm.

[0786] [Table 14]

[0787] Refractive index mmtBumTPchPAF-02 1.67 mmtBumTPoFBi-02 1.70 PCBBiF 1.94

[0788] In a glove box under a nitrogen atmosphere, the above light-emitting devices and the comparative light-emitting device were sealed with a glass substrate in such a manner that the devices were not exposed to the air (a sealing material was applied to the periphery of the device, and UV treatment was performed at the time of sealing), and the initial characteristics of these light-emitting devices were measured. Note that the glass substrate subjected to the sealing treatment was not subjected to a special treatment for improving light extraction efficiency.

[0789] Figure 69 The luminance-current density characteristics of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5 are shown, Figure 70 The current efficiency-luminance characteristics are shown, Figure 71 The luminance-voltage characteristics are shown, Figure 72 The current density-voltage characteristics are shown, Figure 73 The blue index-luminance characteristics are shown, Figure 74 The emission spectra are shown. In addition, Table 15 shows the main characteristics of each light-emitting device at 1000 cd / m 2 at room temperature using a spectroradiometer (Topcon Corporation, SR-UL1R).

[0790] [Table 15]

[0791]

[0792] from Figures 69 to 74 As can be seen from Table 15, the light-emitting device using the low-refractive index material according to one embodiment of the present invention is an EL device having better current efficiency and blue index (BI) than the comparative light-emitting device.

[0793] Note that the blue index (BI) refers to the value obtained by dividing the current efficiency (cd / A) by the chromaticity y, and is one of the indicators that represent the luminous characteristics of blue light. The smaller the chromaticity y, the higher the color purity of blue light. Blue light with high color purity can present a wider range of blue even if it has a small brightness component. When blue light with high color purity is used, the brightness required to present blue is reduced, thereby achieving the effect of reducing power consumption. Therefore, the BI of chromaticity y, one of the indicators of blue purity, is appropriately used as a method of representing the efficiency of blue light. It can be said that the higher the BI of the light-emitting device, the better the efficiency of the blue light-emitting device as a display.

[0794] then, Figure 75 The current density of the light emitting device 11, the light emitting device 12 and the comparative light emitting device 5 is 50 mA / cm 2 Graph showing changes in luminance over driving time when driven with a constant current. The luminance of light-emitting devices 11 and 12 decreases faster than that of comparative light-emitting device 5. Note that light-emitting devices 11 and 12 have higher luminance than comparative light-emitting device 5, and therefore, when driven with the same current density, light-emitting devices 11 and 12 emit higher luminance than comparative light-emitting device 5.

[0795] Example 12

[0796] In this example, the results of measuring the hole mobility of an organic compound according to one embodiment of the present invention are described. A device for measuring the hole mobility was fabricated, and a method for fabricating the device is described below.

[0797] (Method for Manufacturing Device 1)

[0798] On a glass substrate, an alloy film of silver (Ag), palladium (Pd), and copper (Cu) (Ag-Pd-Cu (APC) film) was formed to a thickness of 100 nm by sputtering, and then indium tin oxide (ITSO) containing silicon oxide was formed to a thickness of 50 nm by sputtering to form the first electrode 101. Note that the electrode area is 4 mm 2 (2mm×2mm).

[0799] Next, as a pretreatment for forming a device on the substrate, the substrate surface was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0800] Then, the substrate is placed inside the chamber and the pressure is reduced to 10 -4 Pa in a vacuum evaporation device, and in a heating chamber in the vacuum evaporation device, vacuum baking is performed at a temperature of 170° C. for 30 minutes, and then the substrate is cooled for about 30 minutes.

[0801] Next, the substrate on which the first electrode 101 was formed was fixed on a substrate holder arranged in a vacuum evaporation device in a manner such that the surface on which the first electrode 101 was formed faced downward, and mmtBumTPchPAF-02 and molybdenum oxide were co-evaporated on the first electrode 101 by an evaporation method in a manner with a thickness of 5 nm and a weight ratio of 1:1 (=mmtBumTPchPAF-02:molybdenum oxide) to form a hole injection layer 111.

[0802] On the hole injection layer 111 , mmtBumTPchPAF-02 was vapor-deposited to a thickness of 520 nm as the hole transport layer 112 .

[0803] Next, mmtBumTPchPAF-02 and molybdenum oxide were co-evaporated to form a buffer layer with a thickness of 5 nm and a weight ratio of 1:1 (=mmtBumTPchPAF-02:molybdenum oxide).

[0804] Next, aluminum (Al) was vapor-deposited to a thickness of 200 nm to form the second electrode 102 , thereby manufacturing the device 1 in which only holes flow.

[0805] (Method for Manufacturing Device 2)

[0806] Device 2 was manufactured in the same manner as Device 1 except that mmtBumTPoFBi-02 was used instead of mmtBumTPchPAF-02 in Device 1 and the thickness of the hole transport layer 112 was changed to 557.5 nm.

[0807] The table below shows the component structures of device 1 and device 2.

[0808] [Table 16]

[0809]

[0810] *4Device 1: 520nm, Device 2: 557.5nm

[0811] In a glove box with a nitrogen atmosphere, the devices were sealed using a glass substrate so as not to be exposed to the atmosphere (a sealing material was applied around the device and UV treatment was performed during sealing), and then these devices were measured.

[0812] Figure 76 Shown are the current density-voltage characteristics of Device 1 and Device 2. Note that this measurement was performed at room temperature.

[0813] Use device simulation from Figure 76 The hole mobility of each organic compound was calculated based on the electrical characteristics shown. The simulation was performed using the Drift-Diffusion module of Setfos (CYBERNET SYSTEMS CO., LTD). As simulation parameters, the work function of ITSO of the first electrode 101 was set to 5.36 eV, the work function of Al of the second electrode 102 was set to 4.2 eV, the HOMO level of mmtBumTPchPAF-02 was set to -5.39 eV, and the HOMO level of mmtBumTPoFBi-02 was set to -5.43 eV. In addition, the charge density of the hole transport layer 112 was set to 1.0×10 18 cm -3 .

[0814] The work function of the electrode was measured in the atmosphere using photoelectron spectroscopy (AC-2 manufactured by Riken Keiki Co., Ltd.).

[0815] The HOMO energy level of an organic compound is measured by cyclic voltammetry (CV). Furthermore, an electrochemical analyzer (BAS Inc., ALS model 600A or 600C) is used to measure a solution of each compound dissolved in N,N-dimethylformamide (DMF). During the measurement, the potential of the working electrode relative to the reference electrode is varied within an appropriate range to obtain the oxidation peak potential and the reduction peak potential. The redox potential of the reference electrode is estimated to be -4.94 eV, so the HOMO energy level of each organic compound can be calculated from this value and the obtained peak potential.

[0816] Figure 77 The electric field intensity dependence of the hole mobility of each organic compound calculated by simulation is shown. Note that Figure 77 The horizontal axis is expressed as 1 / 2 power of the electric field intensity converted from voltage. In addition, the table below shows 300 (V / cm) 1 / 2 The hole mobility with the electric field strength.

[0817] [Table 17]

[0818]

[0819] *5 Electric field strength 300 (V / cm) 1 / 2

[0820] Thus, the organic compound of one embodiment of the present invention has 1×10 -6 cm 2 Because it has a hole mobility of 100 nm / Vs or higher, it is suitable for the hole transport layer of a light-emitting device.

[0821] Example 13

[0822] "Synthesis Example 7"

[0823] In this example, a method for synthesizing the organic compound N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-4-yl)-N-(1,1'-biphenyl-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPoFBi-04), which is one embodiment of the present invention and represented by structural formula (150) in embodiment 1, is described. The structure of mmtBumTPoFBi-04 is shown below.

[0824] [Chemical Formula 60]

[0825]

[0826] <Step 1: Synthesis of 4-bromo-3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl>

[0827] 9.0 g (20.1 mmol) of 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 6.8 g (24.1 mmol) of 1-bromo-4-iodobenzene, 8.3 g (60.3 mmol) of potassium carbonate, 100 mL of toluene, 40 mL of ethanol, and 30 mL of tap water were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen. 91 mg (0.40 mmol) of palladium acetate and 211 mg (0.80 mmol) of triphenylphosphine were added, and the mixture was heated at 80°C for approximately 4 hours. The flask was then allowed to return to room temperature, and the organic and aqueous layers were separated. Magnesium sulfate was added to the solution to dry the water and concentrate the solution. The resulting hexane solution was purified by silica gel column chromatography to obtain 6.0 g of the desired product as a white solid in a 62.5% yield. The following formula represents the synthesis scheme for 4-bromo-3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl in Step 3.

[0828] [Chemical Formula 61]

[0829]

[0830] <Step 2: Synthesis of mmtBumTPoFBi-04>

[0831] 3.0 g (6.3 mmol) of 4-bromo-3", 5', 5"-tri-tert-butyl-1,1':3', 1"-terphenyl, 2.3 g (6.3 mmol) of N-(1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H-fluorene-2-amine, 1.8 g (18.9 mmol) of sodium tert-butoxide and 32 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 72 mg (0.13 mmol) of bis(dibenzylideneacetone)palladium (0) and 76 mg (0.38 mmol) of tri-tert-butylphosphine were added. The mixture was stirred at 12 ℃ for 2 h. The mixture was heated at 0°C for about 8 hours. Then, the temperature of the mixture was lowered to about 60°C, about 1 mL of water was added, the precipitated solid was filtered out, and washed with toluene. The filtrate was concentrated, and the obtained toluene solution was purified by silica gel column chromatography. The obtained solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and it was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at about 20°C, and the obtained solid was dried under reduced pressure at about 80°C to obtain 3.6 g of the target substance as a white solid with a yield of 75%. In addition, the following formula shows the synthesis scheme of mmtBumTPoFBi-04 in step 4.

[0832] [Chemical Formula 62]

[0833]

[0834] Figure 78A and Figure 78B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained in step 2. Note that Figure 78B It is magnified Figure 78A The graph shows the range of 6.5ppm to 8.0ppm in the above embodiment. In addition, the numerical data are shown below. As can be seen from this, mmtBumTPoFBi-04 can be synthesized in this synthesis example.

[0835] 1H-NMR.δ (CDCl3): 7.54-7.56 (m, 1H), 7.53 (dd, 1H, J=1.7Hz), 7.50 (dd, 1H, J=1.7Hz), 7.27-7.47 (m, 13H), 7.23 (dd, 1H, J=6.3Hz, 1.2Hz ), 7.18-7.19 (m, 2H), 7.08-7.00 (m, 5H), 6.88 (d, 1H, J=1.7Hz) 6.77 (dd, 1H, J=8.0Hz, 2.3Hz), 1.42 (s, 9H), 1.39 (s, 18H), (1.29 (s, 6H).

[0836] Next, 3.6 g of the resulting white solid was purified by gradient sublimation. Sublimation was performed at 255°C under a pressure of 3.9 Pa and an argon flow rate of 15.0 mL / min. After sublimation purification, 2.1 g of a slightly yellowish white solid was obtained with a recovery rate of 58%.

[0837] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPoFBi-04 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) with the toluene solution placed in a quartz cell and at room temperature. The emission spectrum was measured using a fluorescence spectrophotometer (FP-8600, manufactured by JASCO Corporation) with the toluene solution placed in a quartz cell and at room temperature. Figure 79 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 79 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 79 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0838] like Figure 79 As shown, the organic compound mmtBumTPoFBi-04 has a luminescence peak at 396 nm.

[0839] Next, the mmtBumTPoFBi-04 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0840] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0841] In LC separation, an arbitrary column was used, the column temperature was 40° C., and the injection conditions were as follows: a solvent was appropriately selected, mmtBumTPoFBi-04 was dissolved in an organic solvent to adjust the sample to an arbitrary concentration, and the injection volume was 5.0 μL.

[0842] MS of the ion m / z = 757.46 derived from mmtBumTPoFBi-04 was performed using the PRM method. 2 Measurement. PRM settings were: target ion mass range m / z = 757.46 ± 2.0 (isolation window = 4); detection in positive mode. Measurement was performed with the NCE (Normalized Collision Energy) energy used to accelerate the target ion in the collision cell set to 50. Figure 80 The obtained MS spectrum is shown.

[0843] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPoFBi-04 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that mmtBumTPoFBi-04 had a Tg of 123°C.

[0844] Example 14

[0845] "Synthesis Example 8"

[0846] In this example, a method for synthesizing the organic compound N-(3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl-4-yl)-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPchPAF-04), which is one embodiment of the present invention and represented by structural formula (151) in embodiment 1, is described. The structure of mmtBumTPchPAF-04 is shown below.

[0847] [Chemical Formula 63]

[0848]

[0849] <Step 1: Synthesis of 4-bromo-3",5',5"-tri-tert-butyl-1,1':3',1"-terphenyl>

[0850] The product was synthesized in the same manner as in Step 1 of Synthesis Example 7.

[0851] <Step 2: Synthesis of mmtBumTPchPAF-04>

[0852] 3.0 g (6.3 mmol) of 4-bromo-3", 5', 5"-tri-tert-butyl-1,1':3', 1"-terphenyl obtained in step 1, 2.3 g (6.3 mmol) of N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine, 1.8 g (18.9 mmol) of sodium tert-butoxide and 32 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 72 mg (0.13 mmol) of bis(dibenzylideneacetone)palladium (0) and 76 mg (0.38 mmol) of tri-tert-butylphosphine were added. The mixture was stirred at 80 ℃ for 2 h. The mixture was heated at 40°C for approximately 2 hours. The flask temperature was then returned to approximately 60°C, and approximately 1 mL of water was added. The precipitated solid was filtered and washed with toluene. The filtrate was concentrated, and the resulting toluene solution was purified using silica gel column chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and the solution was concentrated under reduced pressure to obtain an ethanol suspension. The precipitated solid in the ethanol suspension was filtered at approximately 20°C, and the resulting solid was dried under reduced pressure at approximately 80°C to obtain 4.1 g of the desired product as a white solid in an 85% yield. The following formula shows the synthesis scheme for mmtBumTPchPAF-04.

[0853] [Chemical Formula 64]

[0854]

[0855] Figure 81A and Figure 81B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained in step 2. Note that Figure 81B It is magnified Figure 81A The graph shows the range of 6.5ppm to 8.0ppm in the present invention. In addition, the numerical data are shown below. As can be seen from this, mmtBumTPchPAF-04 can be synthesized in this synthesis example.

[0856] 1H-NMR.δ (CDCl3): 7.63 (d, 1H, J=7.5Hz), 7.52-7.59 (m, 7H), 7.44-7.45 (m, 4H), 7.39 (d, 1H, J=7.4Hz), 7.31 (dd, 1H, J=7.4Hz), 7.19 (d, 2H, J=6.6Hz) , 7.12(m, 4H), 7.07(d, 1H, J=9.7Hz), 2.48(brm, 1H), 1.84-1.93(brm, 4H), 1.74-1.76 (brm, 1H), 1.43 (s, 18H), 1.39 (brm, 19H), 1.24-1.30 (brm, 1H).

[0857] Next, 4.1 g of the resulting white solid was purified by gradient sublimation. Heating at 255°C under a pressure of 4.3 Pa and an argon flow rate of 15.0 mL / min was performed. After sublimation purification, 3.0 g of a slightly yellowish-white solid was obtained with a recovery rate of 73%.

[0858] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPchPAF-04 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) with the toluene solution placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorescence spectrophotometer (FP-8600, manufactured by JASCO Corporation) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 82 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 82 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 82 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0859] like Figure 82 As shown, the organic compound mmtBumTPchPAF-04 has an emission peak at 397 nm.

[0860] Next, the mmtBumTPchPAF-04 obtained in this example was analyzed using liquid chromatography-mass spectrometry (LC / MS analysis).

[0861] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using Q Exactive manufactured by Thermo Fisher Scientific.

[0862] For LC separation, an arbitrary column was used at a column temperature of 40° C. The injection conditions were as follows: a solvent was appropriately selected, mmtBumTPchPAF-04 was dissolved in an organic solvent at an arbitrary concentration to prepare the sample, and the injection volume was 5.0 μL.

[0863] MS of the ion m / z = 764.52 derived from mmtBumTPchPAF-04 was performed using the PRM method. 2 Measurement. PRM settings were: target ion mass range m / z = 764.52 ± 2.0 (isolation window = 4); detection in positive mode. Measurement was performed with the NCE (Normalized Collision Energy) energy used to accelerate the target ion in the collision cell set to 50. Figure 83 The obtained MS spectrum is shown.

[0864] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPchPAF-04 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that mmtBumTPchPAF-04 had a Tg of 122°C.

[0865] Example 15

[0866] "Synthesis Example 9"

[0867] In this example, a method for synthesizing the organic compound N-(1,1'-biphenyl-2-yl)-N-(3,3",5"-tri-tert-butyl-1,1':4',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumTPoFBi-05), which is one embodiment of the present invention and represented by structural formula (175) in embodiment 1, is described. The structure of mmtBumTPoFBi-05 is shown below.

[0868] [Chemical Formula 65]

[0869]

[0870] <Step 1: Synthesis of 4-bromo-3',5'-di-tert-butylbiphenyl>

[0871] Into a three-necked flask were placed 12.0 g (43 mmol) of 1-bromo-4- iodobenzene, 10.0 g (43 mmol) of 3,5-di-tert-butylphenylboronic acid, 17.7 g (128 mmol) of potassium carbonate, 285 mL of toluene, 85 mL of ethanol, 60 mL of tap water, after degassing under reduced pressure, the inside of the flask was replaced with nitrogen, 2.5 g (2.1 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was heated at 40°C for about 5 hours. Then, the temperature of the flask was returned to room temperature, and the organic layer and the aqueous layer were separated. Magnesium sulfate was added to the solution to remove moisture, and the solution was concentrated. The resulting solution was purified by silica gel column chromatography, and 11.1 g of the desired product was obtained as a colorless oil at a yield of 76%. The following formula shows a synthetic scheme of 3-bromo-3',5,5'-tri-tert-butylbiphenyl of Step 1.

[0872] [Chem. 66]

[0873]

[0874] <Step 2: Synthesis of 2-(3',5'-di-tert-butyl[l,l'-biphenyl]-4-yl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane>

[0875] Into a three-necked flask were placed 11.1 g (32 mmol) of 4-bromo-3',5'-di-tert- butylbiphenyl obtained in Step 1, 9.0 g (35 mmol) of 4,4,4',4',5,5,5',5-octamethyl-2,2'- bi- 1,3,2-dioxaborolane, 9.5 g (96 mmol) of potassium acetate, 214 mL of N,N- dimethylformamide, after degassing under reduced pressure, the inside of the flask was replaced with nitrogen, 1.3 g (1.6 mmol) of [l,l'-bis(diphenylphosphino)ferrocene] dichloropalladium(II) was added, and the mixture was heated at 100°C for about 3 hours. Then, the temperature of the flask was returned to room temperature, and the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with ethyl acetate. Magnesium sulfate was added to the solution to remove moisture, and the solution was concentrated. The resulting mixture was purified by silica gel column chromatography, and 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. The precipitate was filtered at about 20°C, and the resulting solid was dried under reduced pressure at about 80°C, to obtain 11.6 g of the desired product as a white solid at a yield of 92%. The following formula shows a synthetic scheme of Step 2.

[0876] [Chem. 67]

[0877]

[0878] <Step 3: Synthesis of 3-bromo-3',5,5"-tri-tert-butyl-1,1':3',1"-terphenyl>

[0879] Into a three-necked flask were placed 11.6 g (38.2 mmol) of 2-(3',5'-di-tert-butyl[l,l'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborinane, 16.6 g (57.3 mmol) of 1,3-dibromo-5-tert-butylbenzene, 15.8 g (115 mmol) of potassium carbonate, 255 mL of toluene, 76 mL of ethanol, 57 mL of tap water, after degassing treatment under reduced pressure, the flask was replaced with nitrogen gas, 2.2 g (1.9 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was heated at 80°C for about 10 hours. Then, the temperature of the flask was returned to room temperature, and the organic layer and the aqueous layer were separated. Magnesium sulfate was added to the solution to dry the moisture, and the solution was concentrated. The resulting solution was purified by silica gel column chromatography in hexane, and 4.4 g of the white solid of the desired product was obtained in a yield of 24.4%. The synthesis scheme of 3-bromo-3',5,5"-tri-tert-butyl-l,l':3',l"-terphenyl of Step 3 is shown by the following formula.

[0880] [Chemical Formula 68]

[0881]

[0882] <Step 4: Synthesis of mmtBumTPoFBi-05>

[0883] 2.2 g (4.6 mmol) of 3-bromo-3",5,5"-tri-tert-butyl-1,1':3',1"-terphenyl, 1.7 g (4.6 mmol) of N-(1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine, 1.3 g (13.8 mol) of sodium tert-butoxide, and 23 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 53 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) and 56 mg (0.28 mmol) of tri-tert-butylphosphine were added. , heat the mixture at 120°C for about 8 hours. Then, return the temperature of the flask to about 60°C, add about 1 mL of water, filter out the precipitated solid, and wash with toluene. Concentrate the filtrate, and purify the obtained toluene solution by silica gel column chromatography. Concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter out the solid precipitated in the ethanol suspension at about 20°C, dry the obtained solid under reduced pressure at about 80°C, and obtain 2.7 g of the target white solid with a yield of 77%. The following formula shows the synthesis scheme of step 4.

[0884] [Chemical Formula 69]

[0885]

[0886] Figure 84A and Figure 84B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained in step 4. Note that Figure 84B It is magnified Figure 84A The graph shows the range of 6.5ppm to 8.0ppm in the above embodiment. In addition, the numerical data are shown below. As can be seen from this, mmtBumTPoFBi-05 can be synthesized in this synthesis example.

[0887] 1 H-NMR.δ (CDCl3): 7.56-7.60 (m, 3H), 7.49 (d, 2H, J=8.0Hz), 7.27-7.46 (m, 10H), 7.22 (dd, 1H, J=7.5Hz, 1.2Hz), 7.18 (dd, 2H, J=8.0Hz, 1.2 Hz), 7.10 (dd, 1H, J=1.7Hz), 7.04-7.07 (m, 2H), 6.97-7.01 (m, 4H), 6.82 (dd, 1H, J=8.0Hz, 2.3Hz), 1.37 (s, 18H), 1.31 (s, 6H), 1.21 (s, 9H).

[0888] Next, 2.7 g of the obtained white solid was subjected to sublimation purification by a gradient sublimation method. The sublimation purification was performed at 255°C under a pressure of 2.9 Pa and an argon flow rate of 15.0 mL / min. After the sublimation purification, 2.0 g of a slightly yellowish white solid was obtained at a recovery rate of 74%.

[0889] Next, the ultraviolet-visible absorption spectrum (hereinafter, referred to as "absorption spectrum") and the emission spectrum of a toluene solution of mmtBumTPoFBi-05 were measured. When the absorption spectrum was measured, an ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation, Model V550) was used, the toluene solution was placed in a quartz cell, and the measurement was performed at room temperature. When the emission spectrum was measured, a fluorescence spectrophotometer (manufactured by Shimadzu Corporation, Model FP-8600) was used, the toluene solution was placed in a quartz cell, and the measurement was performed at room temperature. Figure 85 The measurement results of the obtained absorption spectrum and emission spectrum are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and the emission intensity. In addition, in Figure 85 the two solid lines, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 85 The absorbance shown represents the result obtained by subtracting the absorption spectrum measured by placing only toluene in a quartz cell from the absorption spectrum measured by placing the toluene solution in a quartz cell.

[0890] As shown in Figure 85 , the organic compound mmtBumTPoFBi-05 has a luminescence peak at 407 nm.

[0891] Next, the glass transition point (hereinafter, referred to as "Tg") of mmtBumTPoFBi-05 was measured. The Tg was measured by placing a powder on an aluminum cell using a differential scanning calorimetry measuring device (PYRIS 1 DSC manufactured by PerkinElmer Japan Co., Ltd.). As a result, the Tg of mmtBumTPoFBi-05 was 118°C.

[0892] Example 16

[0893] Synthesis Example 10

[0894] In this example, a method for synthesizing an organic compound N-(4-cyclohexylphenyl)-N-(3,3",5"-tri-tert-butyl-1,1':4',1"-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPchPAF-05) of one embodiment of the present application represented by Structural Formula (176) in Embodiment Mode 1 will be described. The synthesis scheme of mmtBumTPchPAF-05 is shown below.

[0895] The structure of mmtBumTPchPAF-05.

[0896] [Chemical Formula 70]

[0897]

[0898] <Step 1: Synthesis of 4-bromo-3',5'-di-tert-butylbiphenyl>

[0899] The product was synthesized in the same manner as in Step 1 of Synthesis Example 9.

[0900] <Step 2: Synthesis of 2-(3',5'-di-tert-butyl[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0901] The product was synthesized in the same manner as in Step 2 of Synthesis Example 9.

[0902] <Step 3: Synthesis of 3-bromo-3",5,5"-tri-tert-butyl-1,1':3',1"-terphenyl>

[0903] The product was synthesized in the same manner as in Step 3 of Synthesis Example 9.

[0904] <Step 4: Synthesis of mmtBumTPchPAF-05>

[0905] 2.2 g (4.6 mmol) of 3-bromo-3", 5,5"-tri-tert-butyl-1,1':3',1"-terphenyl obtained in step 3, 1.7 g (4.6 mmol) of N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine, 1.3 g (13.8 mmol) of sodium tert-butoxide, and 23 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 53 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium (0) and 56 mg (0.28 mmol) of tri-tert-butylphosphine were added. The mixture was stirred at 80 ℃ for 2 h. The mixture was heated at 140°C for approximately 2 hours. The temperature of the flask was then returned to approximately 60°C, and approximately 1 mL of water was added. The precipitated solid was filtered out and washed with toluene. The filtrate was concentrated, and the resulting toluene solution was purified by silica gel column chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and the solution was concentrated under reduced pressure to obtain an ethanol suspension. The precipitated solid in the ethanol suspension was filtered out at approximately 20°C, and the resulting solid was dried under reduced pressure at approximately 80°C to obtain 3.2 g of the target compound as a white solid in a yield of 91%. The following formula shows the synthesis scheme of mmtBumTPchPAF-05.

[0906] [Chemical Formula 71]

[0907]

[0908] Figure 86A and Figure 86B The results show that the nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained in step 4. Note that Figure 86B It is magnified Figure 86A This graph shows the range of 6.5 ppm to 8.0 ppm in the HPLC. It can be seen from this that mmtBumTPchPAF-05 can be synthesized in this synthesis example.

[0909] 1 H-NMR.δ(CDCl3): 7.64(d, 1H, J=7.4Hz), 7.56-7.61(m, 6H), 7.42(s, 3H), 7.39(d, 1H, J=7.4Hz), 7.23-7.32 (m, 5H), 7.12 (dd, 4H, J=3.4Hz, 6.3Hz, 2.3Hz), 7.04 (dd, 1 H, J=7.9Hz, 1.7Hz), 2.48-2.50 (brm, 1H), 1.84-1.93 (brm, 4H), 1.73-1.76 (brm, 1 H), 1.43 (s, 6H), 1.40-1.42 (m, 4H), 1.37 (s, 18H). 1.29 (s, 9H), 1.24-1.26 (m, 1H).

[0910] Next, 3.2 g of the resulting white solid was purified by gradient sublimation. Sublimation was performed at 255°C under a pressure of 2.9 Pa and an argon flow rate of 15.0 mL / min. After sublimation purification, 2.1 g of a slightly yellowish-white solid was obtained with a recovery rate of 66%.

[0911] Next, the UV-visible absorption spectrum (hereinafter referred to as the "absorption spectrum") and emission spectrum of a toluene solution of mmtBumTPchPAF-05 were measured. The absorption spectrum was measured using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) with the toluene solution placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorescence spectrophotometer (FP-8600, manufactured by JASCO Corporation) with the toluene solution placed in a quartz cell and measured at room temperature. Figure 87 The measurement results of the absorption spectrum and emission spectrum obtained are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and luminescence intensity. Figure 87 There are two solid lines in the middle, the thin solid line represents the absorption spectrum, and the thick solid line represents the emission spectrum. Figure 87 The absorbance shown represents the result obtained by subtracting the absorption spectrum obtained by placing only toluene in a quartz cell from the absorption spectrum obtained by placing a toluene solution in a quartz cell.

[0912] like Figure 87 As shown, the organic compound mmtBumTPchPAF-05 has an emission peak at 416 nm.

[0913] Next, the glass transition point (hereinafter referred to as "Tg") of mmtBumTPchAPF-05 was measured. The powder was placed on an aluminum cell using a differential scanning calorimeter (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) to measure Tg. The results showed that mmtBumTPchAPF-05 had a Tg of 121°C.

[0914] Example 17

[0915] "Synthesis Example 11"

[0916] This example describes a method for synthesizing the organic compound N-(1,1'-biphenyl-2-yl)-N-(3",3"',5",5"'-tetra-tert-butyl-1,1':3',1":5',1"'-tetraphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumQPoFBi), which is one embodiment of the present invention. The structure of mmtBumQPoFBi is shown below.

[0917] [Chemical Formula 72]

[0918]

[0919] <Step 1: Synthesis of N-(1,1'-biphenyl-2-yl)-N-(1-bromophenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine>

[0920] 10 g (28 mmol) of 2-(2-biphenyl)amino-9,9-dimethylfluorene, 17 g (55 mmol) of 1-bromo-4-iodobenzene, 4.0 g (42 mmol) of sodium tert-butoxide, and 92 mL of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen. 1.3 g (1.4 mmol) of bis(dibenzylideneacetone)palladium (0) and 0.28 g (1.4 mmol) of tri-tert-butylphosphine were added, and the mixture was heated at 80°C for about 4 hours. Then, the temperature of the flask was returned to about 60°C, about 1 mL of water was added, and the precipitated solid was filtered out and washed with toluene. The filtrate was concentrated, and the obtained toluene solution was purified by silica gel column chromatography. The obtained solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and it was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at about 20° C., and the obtained solid was dried under reduced pressure at about 80° C. to obtain 9.4 g of the target compound as a white solid in a yield of 66%. The synthesis scheme of Step 1 is shown below.

[0921] [Chemical Formula 73]

[0922]

[0923] <Step 2: Synthesis of 2-(3',3",5',5"-tetra-tert-butyl[1,1':3,1"-terphenyl]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane>

[0924] 7.0 g (13 mmol) of 5-bromo-3',3",5',5"-tetra-tert-butyl-1,1':3,1"-terphenyl, 3.7 g (14 mmol) of 4,4,4',4',5,5,5',5-octamethyl-2,2'-bi-1,3,2-dioxaborolane, 3.9 g (39 mmol) of potassium acetate, and 87 mL of N,N-dimethylformamide were placed in a three-necked flask. After degassing under reduced pressure, the air in the flask was replaced with nitrogen, and 0.53 g (0.66 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium ( II), heat the mixture at 100°C for about 3 hours. Then, return the temperature of the flask to room temperature and separate the organic layer and the aqueous layer, and extract the aqueous layer with ethyl acetate. Add magnesium sulfate to the solution to remove moisture and concentrate the solution. Purify the toluene solution of the obtained mixture by silica gel column chromatography, and concentrate the obtained solution to obtain a concentrated toluene solution. Add ethanol to the toluene solution and concentrate under reduced pressure to obtain an ethanol suspension. Filter the precipitate at about 20°C, and dry the obtained solid under reduced pressure at about 80°C to obtain 5.2g of the target product as a white solid with a yield of 68%. The synthesis scheme of step 2 is shown below.

[0925] [Chemical Formula 74]

[0926]

[0927] <Step 3: Synthesis of mmtBumQPoFBi>

[0928] 1.7 g (3.4 mmol) of N-(1,1'-biphenyl-2-yl)-N-(1-bromophenyl-4-yl)-9,9-dimethyl-9H-fluorene-2-amine synthesized by step 1, 2.0 g (3.4 mmol) of 2-(3',3",5',5"-tetra-tert-butyl[1,1':3,1"-terphenyl]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized by step 2, 1.4 g (10 mmol) of potassium carbonate, 23 mL of toluene, 7.0 mL of ethanol and 5.0 mL of tap water were put into a three-well plate. In a flask, after degassing under reduced pressure, the air in the flask was replaced with nitrogen, 15 mg (0.068 mmol) of palladium acetate and 41 mg (0.14 mmol) of tri(2-methylphenyl)phosphine were added, and the mixture was heated at 80°C for about 5 hours. Then, the temperature of the flask was returned to room temperature, and the organic layer and the aqueous layer were separated. Magnesium sulfate was added to the organic layer to dry the water and concentrate the organic layer. The hexane solution of the obtained solution was purified by silica gel column chromatography to obtain 2.2 g of the target product as a colorless oil with a yield of 73%. The synthesis scheme of step 3 is shown below.

[0929] [Chemical Formula 75]

[0930]

[0931] 88 and the following show the use of nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis of the white solid obtained in the above step 3. This shows that mmtBumQPoFBi can be synthesized in this synthesis example.

[0932] 1 H-NMR. δ (CDCl3): 7.68-7.69 (m, 3H), 7.55 (d, 1H, J=7.4Hz), 7.48-7.50 (m, 8H), 7.27-7.46 (m, 6H), 7.18-7.23 (m, 4H), 7.01-7.11 (m, 5H), 6.87 (d, 1H, J=1.7Hz), 6.78 (dd, 1H, J=5.2Hz, 2.3Hz), 1.39 (s, 36H), 1.29 (s, 6H).

[0933] 2.2 g of the resulting white solid was purified by gradient sublimation. Heating at 260° C. under a pressure of 2.9 Pa and an argon flow rate of 10 mL / min was performed. After sublimation purification, 1.5 g of a slightly yellowish white solid was obtained with a recovery rate of 68%.

[0934] Example 18

[0935] "Synthesis Example 12"

[0936] This example describes a method for synthesizing the organic compound N-(4-cyclohexylphenyl)-N-(3",3"',5",5"'-tetra-tert-butyl-1,1':3',1":5',1"'-quaterphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as mmtBumQPchPAF), which is one embodiment of the present invention. The structure of mmtBumQPchPAF is shown below.

[0937] [Chemical Formula 76]

[0938]

[0939] <Step 1: Synthesis of N-(4-cyclohexylphenyl)-N-(1-bromophenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine>

[0940] 11 g (30 mmol) of N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine, 17 g (60 mmol) of 1-bromo-4-iodobenzene, 4.3 g (45 mmol) of sodium tert-butoxide, and 0.10 L of toluene were placed in a three-necked flask. After degassing under reduced pressure, the air in...

Claims

1. An arylamine compound represented by the general formula (G1): in: Ar 1 represents a substituted or unsubstituted benzene ring or a substituent in which two or three substituted or unsubstituted benzene rings are bonded to each other, R 6 、R 7 and R 8 Each independently represents an alkyl group having 1 to 4 carbon atoms, m represents an integer from 0 to 4, R 11 to R 15 One of represents a substituent represented by the general formula (g1), R 11 to R 15 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 21 to R 25 One of represents a substituent represented by the general formula (g2), R 21 to R 25 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 31 to R 35 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of them represent branched chain alkyl groups having 3 to 5 carbon atoms, R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least two of the three combinations are R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least one of represents any one of the substituents other than hydrogen.

2. The arylamine compound according to claim 1, When m is greater than 2, multiple R 8 represent the same alkyl group.

3. An arylamine compound represented by the general formula (G2): in: p and r each independently represent 1 or 2, p+r is 2 or 3, R 6 to R 9 Each independently represents an alkyl group having 1 to 4 carbon atoms, m and n each independently represent an integer from 0 to 4, R 41 to R 45 Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms, R 11 to R 15 One of them is a substituent represented by the general formula (g1), R 11 to R 15 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 21 to R 25 One of represents a substituent represented by the general formula (g2), R 21 to R 25 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 31 to R 35 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of them represent branched chain alkyl groups having 3 to 5 carbon atoms, R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least two of the three combinations in R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least one of represents any one of the substituents other than hydrogen.

4. An arylamine compound represented by the general formula (G2): in: p and r each independently represent 1 or 2, p+r is 2 or 3, R 6 to R 9 Each independently represents an alkyl group having 1 to 4 carbon atoms, m and n each independently represent an integer from 0 to 4, R 41 to R 45 Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms, When r is 2, the two phenyl groups are the same. R 11 to R 15 One of them is a substituent represented by the general formula (g1), R 11 to R 15 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 21 to R 25 One of represents a substituent represented by the general formula (g2), R 21 to R 25 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 31 to R 35 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of them represent branched chain alkyl groups having 3 to 5 carbon atoms, R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least two of the three combinations in R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least one of represents any one of the substituents other than hydrogen.

5. An arylamine compound represented by the general formula (G2): in: p and r each independently represent 1 or 2, p+r is 2 or 3, R 6 to R 9 Each independently represents an alkyl group having 1 to 4 carbon atoms, m and n each independently represent an integer from 0 to 4, R 41 to R 45 Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms, When r is 2, the two phenyl groups are different from each other. R 11 to R 15 One of them is a substituent represented by the general formula (g1), R 11 to R 15 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 21 to R 25 One of represents a substituent represented by the general formula (g2), R 21 to R 25 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 31 to R 35 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of them represent branched chain alkyl groups having 3 to 5 carbon atoms, R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least two of the three combinations in R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least one of represents any one of the substituents other than hydrogen.

6. An arylamine compound represented by the general formula (G2): in: Both p and r represent 1, R 6 to R 9 Each independently represents an alkyl group having 1 to 4 carbon atoms, m represents an integer from 0 to 4, n represents 0, R 41 to R 45 Each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms, R 11 to R 15 One of them is a substituent represented by the general formula (g1), R 11 to R 15 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 21 to R 25 One of represents a substituent represented by the general formula (g2), R 21 to R 25 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 31 to R 35 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of them represent branched chain alkyl groups having 3 to 5 carbon atoms, R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least two of the three combinations in R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least one of represents any one of the substituents other than hydrogen.

7. An arylamine compound represented by the general formula (G3): in: R 1 to R 5 each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, and a substituted or unsubstituted phenyl group, R 6 、R 7 and R 8 Each independently represents an alkyl group having 1 to 4 carbon atoms, m represents an integer from 0 to 4, When m is 2 or more, multiple R 8 represents the same alkyl group or different alkyl groups, R 11 to R 15 One of represents a substituent represented by the general formula (g1), R 11 to R 15 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 21 to R 25 One of represents a substituent represented by the general formula (g2), R 21 to R 25 The others in each independently represent any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 31 to R 35 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms, R 11 to R 15 、R 21 to R 25 and R 31 to R 35 At least three of them represent branched chain alkyl groups having 3 to 5 carbon atoms, R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least two of the three combinations are R 12 and R 14 、R 22 and R 24 and R 32 and R 34 At least one of represents any one of the substituents other than hydrogen.

8. The arylamine compound according to claim 7, where R 3 Represents cyclohexyl, R 1 、R 2 、R 4 、R 5 Both represent hydrogen.

9. The arylamine compound according to claim 7, where R 1 represents unsubstituted phenyl, R 2 to R 5 Both represent hydrogen.

10. The arylamine compound according to any one of claims 1 to 7, The branched chain alkyl group having 3 to 5 carbon atoms is a tert-butyl group.

11. The arylamine compound according to any one of claims 1 to 7, The ordinary refractive index of the layer formed by the arylamine compound with respect to light with a wavelength of greater than or equal to 455 nm and less than or equal to 465 nm is greater than or equal to 1.50 and less than or equal to 1.75, or the ordinary refractive index of the layer formed by the arylamine compound with respect to light with a wavelength of 633 nm is greater than or equal to 1.45 and less than or equal to 1.70.

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