Light emitting device

Abstract

To provide a new arylamine compound having a low refractive index.SOLUTION: An arylamine compound having at least one aromatic group, wherein the aromatic group has a first benzene ring, a second benzene ring, a third benzene ring, and at least three alkyl groups, and the first benzene ring to the third benzene ring are directly bonded in this order, wherein the first benzene ring is bonded to nitrogen of amine, the first benzene ring may further include a substituted or unsubstituted phenyl group, and the second benzene ring or the third benzene ring may further include a phenyl group substituted with an alkyl group, Two or more benzene rings of the first benzene ring to the third benzene ring are each independently bonded to another benzene ring, a benzene ring of a phenyl group substituted with the alkyl group, any of the at least three alkyl groups, or nitrogen of the amine at 1-position and 3-position.SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention is an organic compound, a light-emitting element, a light-emitting device, a display module, a lighting device, a The present invention relates to a light module, a display device, a light-emitting device, an electronic device, a lighting device, and an electronic device. Note that one embodiment of the present invention is not limited to the above technical fields. The technical field of one aspect relates to an article, a method, or a manufacturing method. One aspect of the present invention is a process, machine, manufacture, or composition. Therefore, the invention disclosed herein more specifically relates to The technical field of one aspect of the present invention is a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, device, power storage device, storage device, imaging device, driving method thereof, or manufacturing method thereof This can be cited as an example. [Background technology]

[0002] Electroluminescence (EL) using organic compounds Light-emitting devices (organic EL devices) that utilize these materials are being put to practical use. The basic structure of a light-emitting device is an organic compound layer (EL layer) containing a light-emitting material between a pair of electrodes. When a voltage is applied to this element, carriers (holes and electrons) are injected. By utilizing the recombination energy of the carriers, light can be emitted from the light-emitting material. This can be done.

[0003] Since such light-emitting devices are self-luminous, when they are used as pixels in a display, Compared to flat panel displays, they have the advantage of being highly visible and not requiring a backlight. The light-emitting device is suitable for use as a display element. Another major advantage is that it can be manufactured to be thin and lightweight. It is one of the signs.

[0004] In addition, these light-emitting devices can be fabricated with a continuous two-dimensional light-emitting layer. This is a point light source, such as an incandescent bulb or LED, and This is a feature that is difficult to obtain with linear light sources such as fluorescent lamps, so it is used as a surface light source that can be applied to lighting, etc. It is also highly useful as a tool.

[0005] Displays and lighting devices using such light-emitting devices are suitable for a variety of electronic devices. However, research and development is ongoing to find light-emitting devices with better properties.

[0006] One of the problems that is often raised when discussing organic EL devices is light extraction. In particular, attenuation due to reflection caused by differences in the refractive index of adjacent layers is This is a major factor in reducing the efficiency of the device. A structure has been proposed in which a layer made of a low refractive index material is formed on the surface of the substrate (see, for example, Non-Patent Document 1). ).

[0007] A light-emitting device having this configuration has a higher light extraction efficiency than a light-emitting device having a conventional configuration. This allows for a light-emitting device with high external quantum efficiency. The refractive index layer can be placed inside the EL layer without adversely affecting other important properties of the light-emitting device. It is not easy to form such a material because it requires a low refractive index and high carrier transport properties. This is because there is a trade-off between the reliability and the cost when used in light-emitting devices. The carrier transport properties and reliability of organic compounds are due to the presence of unsaturated bonds. This is because organic compounds that are large and have many unsaturated bonds tend to have a high refractive index. do. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Publication No. 11-282181 [Patent Document 2] Japanese Patent Application Laid-Open No. 2009-91304 [Patent Document 3] U.S. Patent Application Publication No. 2010 / 104969 [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 [Problem to be solved by the invention]

[0009] An object of one aspect of the present invention is to provide a novel material for a hole transport layer. Another object of the present invention is to provide a material for a hole transport layer having a small refractive index. In one embodiment, a material for a hole transport layer having a small refractive index and sufficient carrier transportability is provided. Alternatively, in one embodiment of the present invention, a material having a small refractive index and sufficient hole The object of the present invention is to provide a material for a hole transport layer having transport properties.

[0010] An object of one aspect of the present invention is to provide a novel arylamine compound. In one aspect of the present invention, a novel arylamine compound having sufficient hole transport properties is provided. One aspect of the present invention provides an arylamine compound having a low refractive index. Alternatively, in one embodiment of the present invention, a compound having a small refractive index and sufficient hole transporting property is provided. The object of the present invention is to provide an arylamine compound having the following formula:

[0011] Another object of one embodiment of the present invention is to provide a light-emitting device with high emission efficiency. Alternatively, in one embodiment of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, or a light-emitting element with low power consumption is provided. The present invention aims to provide a display device and an electronic device, respectively.

[0012] The description of these problems does not preclude the existence of other problems. The embodiment does not necessarily have to solve all of these problems. The above will be made clear from the description, drawings, claims, etc. It is possible to extract other issues from the descriptions in the patent, claims, etc.

[0013] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0014] One aspect of the present invention is an arylamine compound having at least one aromatic group, The aromatic group comprises at least a first benzene ring, a second benzene ring, and a third benzene ring. and the first benzene ring to the third benzene ring have three alkyl groups. and the first benzene ring is directly bonded to the arylamine compound. The first benzene ring is bonded to the nitrogen of the benzene ring, and the first benzene ring further contains a substituted or unsubstituted phenyl group. The second benzene ring or the third benzene ring may further include an alkyl group. and the first to third benzene rings may each have a phenyl group substituted with In the benzene ring, two or more benzene rings each independently have another benzene at the 1st and 3rd positions. a benzene ring of a phenyl group substituted with said alkyl group; The aryl amine compounds are those in which either the aryl group or the nitrogen of the amine is bonded.

[0015] Another aspect of the present invention is, in the above structure, The Zene ring is an arylamine compound having a phenyl group substituted with an alkyl group.

[0016] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the first benzene ring is an unsubstituted phenyl. It is an arylamine compound having an aryl group.

[0017] Another embodiment of the present invention is a compound having the above structure, wherein the first to third benzene rings are All benzene rings in phenyl groups substituted with alkyl groups The benzene rings are each independently connected to other benzene rings at the 1-position and the 3-position, and the at least three An arylamine compound in which either the alkyl group or the nitrogen of the amine is bonded be.

[0018] Another embodiment of the present invention is a compound having the above structure, wherein the first to third benzene rings are All benzene rings in phenyl groups substituted with alkyl groups The benzene ring may be bonded independently to another benzene ring at the 1-, 3-, and 5-positions, At least three alkyl groups or the nitrogen of the amine are bonded to the other bonding positions. The arylamine compound is unsubstituted.

[0019] Alternatively, another embodiment of the present invention is a compound having the above-mentioned structure, wherein the arylamine compound further comprises It has a second aromatic group, and the second aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted monocyclic The arylamine compounds are unsubstituted arylamine compounds having a fused ring structure of three or less rings.

[0020] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the second aromatic group is substituted or is an unsubstituted fused ring skeleton having 3 or less rings, and the number of carbon atoms forming the fused ring skeleton is 6 to 1. 3 is an arylamine compound.

[0021] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the fused ring skeleton is a fluorene ring. It is an arylamine compound.

[0022] Alternatively, in the above structure, another embodiment of the present invention is a compound in which the second aromatic group is dimethyl fluorine. It is an arylamine compound that is an oleyl group.

[0023] Alternatively, another embodiment of the present invention is a compound having the above-mentioned structure, wherein the arylamine compound further comprises a third aromatic group, the third aromatic group having one to one substituted or unsubstituted benzene rings; 3 is an arylamine compound having

[0024] Alternatively, another embodiment of the present invention is a compound according to the above structure, wherein the alkyl group has 2 to 4 carbon atoms. It is an arylamine compound with a chain alkyl group of number 5.

[0025] Alternatively, another embodiment of the present invention is a compound according to the above structure, wherein the alkyl group has 3 to 4 carbon atoms. It is an arylamine compound having a chain alkyl group with five branches.

[0026] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the alkyl group is tert-butyl. It is an arylamine compound which is a group.

[0027] Alternatively, another embodiment of the present invention is a compound having the above structure, wherein the compound is a triarylamine compound. It is an arylamine compound.

[0028] Alternatively, another aspect of the present invention is a composition comprising the arylamine compound in the above-mentioned configuration. The refractive index of the layer for ordinary light in the wavelength range of 455 nm to 465 nm is 1.5 to 1.7 5 or less.

[0029] Alternatively, another aspect of the present invention is a composition comprising the arylamine compound in the above-mentioned configuration. The refractive index of the layer for ordinary light at a wavelength of 633 nm is 1.45 or more and 1.70 or less. It is a dimethylamine compound.

[0030] Alternatively, another embodiment of the present invention is a polymer having the above structure, wherein the polymer has a molecular weight of 400 or more and 1100 or less. It is an arylamine compound.

[0031] Alternatively, in another embodiment of the present invention, in the above structure, the glass transition point is preferably 100° C. or higher. The arylamine compound has a temperature of 110°C or higher, and more preferably 120°C or higher.

[0032] Alternatively, in the above-described structure, another embodiment of the present invention is a compound in which the arylamine compound is a monoarylamine. The compound is an arylamine compound.

[0033] Another embodiment of the present invention is an arylamine compound represented by the following general formula (G1): be.

[0034] [ka]

[0035] However, in the above general formula (G1), Ar 1 is a substituted or unsubstituted benzene ring, or It represents 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, and m is 0. When m is 2 or more, a plurality of R 8 Even if each is the same, It is also acceptable to have R 11 ~R 15 is a substituent represented by the above general formula (g1). group, and the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted alkyl group. In the general formula (g1), R 2 1 ~R 25 is a substituent represented by the above general formula (g2), and the rest are each independently hydrogen, alkyl groups having 1 to 6 carbon atoms, and alkyl groups having 1 to 6 carbon atoms; In the general formula (g2), R 31 ~R 35 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and It represents one of phenyl groups substituted with an alkyl group having up to 6 carbon atoms. 11 ~ R 15, R 21 ~R 25 and R 31 ~R 35 At least 3 of these have 1 carbon atom. is an alkyl group having 6 to 6 carbon atoms, and R 11 ~R 15 Substituted or unsubstituted phenyl in R 21 ~R 25 and R 31 ~R 35 Carbon number 1 to 1 The number of phenyl groups substituted with alkyl groups having a prime number of 6 is 1 or less. 12 oh Yobi R 14 , R 22 and R 24 , and R 32 and R 34 Of the three combinations In at least two combinations, at least one R is the above-mentioned substituent other than hydrogen. This shall be the case.

[0036] Another embodiment of the present invention is an arylamine compound represented by the following general formula (G2): be.

[0037] [ka]

[0038] In the above general formula (G2), p and r each independently represent 1 or 2, and p+ r is 2 or 3. Also, R 6 ~R 9 each independently represents an alkyl group having 1 to 4 carbon atoms m and n each independently represent an integer of 0 to 4. 41 ~R 45 Each each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, When m is 2 or more, multiple R 8 are the same for each When n is 2 or more, multiple R 9 Even if each is the same When p is 2, the types of the substituents on the two phenylene groups may be different. The number of substituents and the positions of the bonds may be the same or different. The types of substituents, the number of substituents, and the positions of the bonds of the two phenyl groups are the same. may be different. 11 ~R 15 One of them is represented by the above general formula (g1). the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and It represents either a substituted or unsubstituted phenyl group. , R 21 ~R 25 One of the substituents is a substituent represented by the general formula (g2) above, and the rest are each independently In particular, hydrogen, alkyl groups having 1 to 6 carbon atoms, and alkyl groups having 1 to 6 carbon atoms. In addition, in the above general formula (g2), R 31 ~R 35 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, and a R represents any one of phenyl groups substituted with an alkyl group having 1 to 6 carbon atoms. 1 1 ~R 15 , R 21 ~R 25 and R 31 ~R 35 At least 3 of these are charcoal R is an alkyl group having 1 to 6 carbon atoms; 11 ~R 15 Substituted or unsubstituted in The number of phenyl groups is not more than 1, and R21 ~R 25 and R 31 ~R 35 Carbon number 1 The number of phenyl groups substituted with alkyl groups having 6 to 1 carbon atoms is 1 or less. 12 and R 14 , R 22 and R 24 , and R 32 and R 34 Three combinations of In at least two combinations of the above, at least one R is a substituent other than hydrogen. It is assumed to be a group.

[0039] Alternatively, another aspect of the present invention is an aryl amination compound having the above structure, wherein n is 0. It is a mixture.

[0040] Alternatively, another embodiment of the present invention is an aryl group having the above structure, wherein p is 1 and r is 1. It is an amine compound.

[0041] Another embodiment of the present invention is an arylamine compound represented by the following general formula (G3): be.

[0042] [ka]

[0043] However, in the above general formula (G3), R 1 ~R 5 are each independently hydrogen, a group having 1 to 10 carbon atoms, Alkyl groups having 6 carbon atoms, cycloalkyl groups having 5 to 12 carbon atoms, and substituted or unsubstituted alkyl groups having 6 to 12 carbon atoms. represents one of the substituted phenyl groups. 6 , R 7 and R 8 are each independently the number of carbon atoms represents an alkyl group having 1 to 4 carbon atoms, and m represents an integer of 0 to 4. Note that when m is 2 or more, If multiple R 8 may be the same or different. 11 ~R 15 is a substituent represented by the general formula (g1) above, and the rest are each independently hydrogen, represents any one of an alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted phenyl group; In the above general formula (g1), R 21 ~R 25 One of them is the above general formula (g2) the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, It represents any one of phenyl groups substituted with an alkyl group having 1 to 6 carbon atoms. In the above general formula (g2), R 31 ~R 35 are each independently hydrogen, a group having 1 to 2 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms; It represents one. 11 ~R 15 , R 21 ~R 25 and R 31 ~R 35 Of , at least three of which are alkyl groups having 1 to 6 carbon atoms, and R 11 ~R 15 To The number of substituted or unsubstituted phenyl groups in R is not more than one. 21 ~R 25 and R 31 ~ R 35 In the formula, the number of phenyl groups substituted with alkyl groups having 1 to 6 carbon atoms is 1 or less. In addition, R 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 any of the above substituents other than hydrogen.

[0044] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the R 1 ~R 5 Among them, R 3 Gashi It is an arylamine compound in which the aryl group is cyclohexyl and the remainder is all hydrogen.

[0045] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the R 1 ~R 5 Among them, R 1 There is no It is an arylamine compound in which the phenyl group is substituted and the remainder is all hydrogen.

[0046] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device according to the above-described embodiment, wherein R 12 , R 14 , R 22 and R 2 4 at least one of R is a substituent other than hydrogen; 32 and R 34 At least one of The arylamine compound is an arylamine compound in which the substituents are other than hydrogen.

[0047] Alternatively, another aspect of the present invention is an aryl amination compound having the above structure, wherein m is 0. It is a mixture.

[0048] Alternatively, another embodiment of the present invention is a method for producing a cycloalkyl group having 1 to 6 carbon atoms in the above structure. The arylamine compound has a chain alkyl group having 2 to 5 carbon atoms.

[0049] Alternatively, another embodiment of the present invention is a method for producing a cycloalkyl group having 1 to 6 carbon atoms in the above structure. an arylamine compound in which the alkyl group is a branched chain alkyl group having 3 to 5 carbon atoms; is.

[0050] Alternatively, another embodiment of the present invention is a method for producing a cycloalkyl group having 1 to 6 carbon atoms in the above structure. It is an arylamine compound in which the aryl group is a tert-butyl group.

[0051] Alternatively, another aspect of the present invention is a method for manufacturing a semiconductor device according to the above-mentioned embodiment, wherein R 11 ~R 15 , R 21 ~R 25 and R 31 ~R 35 Among them, R 12 , R 14 , R 22 , R 32 and R 34 More than hydrogen The remaining substituents are hydrogen atoms.

[0052] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the R 12 is the general formula (g1), is a substituent represented by the formula R 22 is a substituent represented by the general formula (g2). It is a dimethylamine compound.

[0053] Alternatively, another embodiment of the present invention is a method for manufacturing a semiconductor device according to the above-described embodiment, wherein R 14 , R 32 and R 34 But It is an arylamine compound with a rt-butyl group.

[0054] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the R 5 and R 6 is a methyl group It is an arylamine compound.

[0055] Alternatively, another aspect of the present invention is a composition comprising the arylamine compound in the above-mentioned configuration. The refractive index of the layer for ordinary light with wavelengths of 455 nm to 465 nm is 1.50 to 1.75 The arylamine compound is shown below.

[0056] Alternatively, another aspect of the present invention is a composition comprising the arylamine compound in the above-mentioned configuration. The ordinary refractive index of the layer for light with a wavelength of 633 nm is 1.45 or more and 1.70 or less. It is an amine compound.

[0057] Alternatively, in another embodiment of the present invention, in the above structure, the glass transition point is preferably 100° C. or higher. The arylamine compound has a temperature of 110°C or higher, and more preferably 120°C or higher.

[0058] Another embodiment of the present invention is a material for a hole transport layer containing the above arylamine compound. be.

[0059] Another embodiment of the present invention is a material for a hole injection layer, which contains the above-described arylamine compound. do.

[0060] Alternatively, another aspect of the present invention is a method for producing a compound comprising the above arylamine compound and a cyano group or a fluorine atom. and a hole injection layer material having an organic compound having a substituent.

[0061] Another embodiment of the present invention is a light-emitting device using any of the above organic compounds. is.

[0062] Another embodiment of the present invention is a light-emitting device including any one of the above light-emitting devices, a sensor, and an operation button. The electronic device has a touch panel, a speaker, or a microphone.

[0063] Another embodiment of the present invention is a light-emitting device including any one of the above light-emitting devices, a transistor, and a Alternatively, the light emitting device may include a substrate.

[0064] Another embodiment of the present invention is a light-emitting device including any one of the above light-emitting devices and a housing. It is a lighting device.

[0065] In this specification, the term "light-emitting device" includes an image display device using a light-emitting device. In addition, a connector such as anisotropic conductive film or TCP (Tape) is attached to the light-emitting device. Module with Carrier Package attached, printed on TCP Modules with wiring boards or light-emitting devices with COG (Chip On Glass) s) method, a module in which an IC (integrated circuit) is directly mounted may also be included in the category of light-emitting device. Furthermore, lighting fixtures and the like may have a light-emitting device. [Effects of the Invention]

[0066] In one embodiment of the present invention, a novel material for a hole transport layer can be provided. According to another aspect of the present invention, a hole transport layer material having a low refractive index can be provided. Therefore, it is possible to provide a material for a hole transport layer having a small refractive index and sufficient hole transport properties. can.

[0067] In one embodiment of the present invention, a novel material for a hole injection layer can be provided. According to another aspect of the present invention, a material for a hole injection layer having a low refractive index can be provided. Therefore, it is possible to provide a material for a hole injection layer having a small refractive index and sufficient hole transport property. can.

[0068] In one aspect of the present invention, a novel arylamine compound can be provided. In one aspect, it is possible to provide a novel arylamine compound having sufficient hole transport properties. In one embodiment of the present invention, an arylamine compound having a small refractive index can be provided. Alternatively, in one embodiment of the present invention, an ant having a small refractive index and sufficient hole transport property can be used. A hydroxylamine compound can be provided.

[0069] Alternatively, according to one embodiment of the present invention, a light-emitting device with high emission efficiency can be provided. In one embodiment of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, a display, or the like with low power consumption is provided. An apparatus and an electronic device may each be provided.

[0070] The description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. , the specification, drawings, claims, etc., and It is possible to extract other effects from the claims and other descriptions. [Brief explanation of the drawings]

[0071] [Figure 1] 1(A), 1(B) and 1(C) are schematic diagrams of light-emitting devices. [Figure 2] 2(A) and 2(B) are conceptual diagrams of an active matrix light emitting device. [Figure 3] 3(A) and 3(B) are conceptual diagrams of an active matrix light emitting device. [Figure 4] FIG. 4 is a conceptual diagram of an active matrix light emitting device. [Figure 5] 5(A) and 5(B) are conceptual diagrams of a passive matrix light emitting device. [Figure 6] 6(A) and 6(B) are diagrams showing a lighting device. [Figure 7] 7(A), 7(B1), 7(B2) and 7(C) are diagrams showing electronic devices. [Figure 8] 8(A), 8(B) and 8(C) are diagrams showing electronic devices. [Figure 9] FIG. 9 is a diagram showing a lighting device. [Figure 10] FIG. 10 is a diagram showing a lighting device. [Figure 11] FIG. 11 is a diagram showing an in-vehicle display device and a lighting device. [Figure 12] 12(A) and 12(B) are diagrams showing electronic devices. [Figure 13] 13(A), 13(B) and 13(C) are diagrams showing electronic devices. [Figure 14] FIG. 14 is a 1H NMR chart of mmtBumTPFA-02. [Figure 15] FIG. 15 shows the absorption spectrum and emission spectrum of mmtBumTPFA-02 in a toluene solution. [Figure 16] FIG. 16 shows the MS spectrum of mmtBumTPFA-02. [Figure 17] FIG. 17 shows the results of measuring the refractive index of mmtBumTPFA-02. [Figure 18] FIG. 18 is a 1H NMR chart of mmtBumTPFBi-02. [Figure 19] FIG. 19 shows the absorption spectrum and emission spectrum of mmtBumTPFBi-02 in a toluene solution. [Figure 20] FIG. 20 shows the MS spectrum of mmtBumTPFBi-02. [Figure 21] FIG. 21 shows the results of measuring the refractive index of mmtBumTPFBi-02. [Figure 22] FIG. 22 is a 1H NMR chart of mmtBumTPoFBi-02. [Figure 23]FIG. 23 shows the absorption spectrum and emission spectrum of mmtBumTPoFBi-02 in a toluene solution. [Figure 24] FIG. 24 is the MS spectrum of mmtBumTPoFBi-02. [Figure 25] FIG. 25 shows the results of measuring the refractive index of mmtBumTPoFBi-02. [Figure 26] FIG. 26 is a 1H NMR chart of mmtBumTPchPAF-02. [Figure 27] FIG. 27 shows the absorption spectrum and emission spectrum of mmtBumTPchPAF-02 in a toluene solution. [Figure 28] FIG. 28 shows the MS spectrum of mmtBumTPchPAF-02. [Figure 29] FIG. 29 shows the results of measuring the refractive index of mmtBumTPchPAF-02. [Figure 30] Figure 30 is a 1H NMR chart of mmtBumTPoFBi-03. [Figure 31] FIG. 31 shows the absorption spectrum and emission spectrum of mmtBumTPoFBi-03 in a toluene solution. [Figure 32] Figure 32 is the MS spectrum of mmtBumTPoFBi-03. [Figure 33] FIG. 33 shows the results of measuring the refractive index of mmtBumTPoFBi-03. [Figure 34] FIG. 34 is a 1H NMR chart of mmtBumTPchPAF-03. [Figure 35] FIG. 35 shows the absorption spectrum and emission spectrum of mmtBumTPchPAF-03 in a toluene solution. [Figure 36] FIG. 36 shows the MS spectrum of mmtBumTPchPAF-03. [Figure 37] FIG. 37 shows the results of measuring the refractive index of mmtBumTPchPAF-03. [Figure 38]FIG. 38 shows the results of measuring the refractive index of mmtBumTPchPAF-02, mmtBumTPoFBi-02, and PCBBiF. [Figure 39] FIG. 39 shows the luminance-current density characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 40] FIG. 40 shows the current efficiency-luminance characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 41] FIG. 41 shows the luminance-voltage characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 42] FIG. 42 shows the current-voltage characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 43] FIG. 43 shows the external quantum efficiency-luminance characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 44] FIG. 44 shows the emission spectra of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 45] FIG. 45 shows the results of measuring the refractive index of mmtBumTPchPAF-03, mmtBumTPoFBi-03, and PCBBiF. [Figure 46] FIG. 46 shows the luminance-current density characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2. [Figure 47] FIG. 47 shows the current efficiency-luminance characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2. [Figure 48] FIG. 48 shows the luminance-voltage characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2. [Figure 49] FIG. 49 shows the current-voltage characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2. [Figure 50] FIG. 50 shows the external quantum efficiency-luminance characteristics of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2. [Figure 51] FIG. 51 shows the emission spectra of the light-emitting device 3, the light-emitting device 4, and the comparative light-emitting device 2. [Figure 52] FIG. 52 shows the results of measuring the refractive index of mmtBumTPchPAF-02, mmtBumTPoFBi-02, mmtBumTPchPAF-03, mmtBumTPoFBi-03, and PCBBiF. [Figure 53] FIG. 53 shows the luminance-current density characteristics of Light-Emitting Device 5, Light-Emitting Device 6, Light-Emitting Device 7, Light-Emitting Device 8, and Comparative Light-Emitting Device 3. [Figure 54] FIG. 54 shows the current efficiency-luminance characteristics of light-emitting device 5, light-emitting device 6, light-emitting device 7, light-emitting device 8, and comparative light-emitting device 3. [Figure 55] FIG. 55 shows the luminance-voltage characteristics of light-emitting device 5, light-emitting device 6, light-emitting device 7, light-emitting device 8, and comparative light-emitting device 3. [Figure 56] FIG. 56 shows the current-voltage characteristics of light-emitting device 5, light-emitting device 6, light-emitting device 7, light-emitting device 8, and comparative light-emitting device 3. [Figure 57] FIG. 57 shows the external quantum efficiency-luminance characteristics of light-emitting device 5, light-emitting device 6, light-emitting device 7, light-emitting device 8, and comparative light-emitting device 3. [Figure 58] FIG. 58 shows the emission spectra of light-emitting device 5, light-emitting device 6, light-emitting device 7, light-emitting device 8, and comparative light-emitting device 3. [Figure 59] FIG. 59 shows the results of measuring the refractive index of mmtBumTPchPAF-02, mmtBumTPoFBi-02, and PCBBiF. [Figure 60] FIG. 60 shows the luminance-current density characteristics of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4. [Figure 61] FIG. 61 shows the current efficiency-luminance characteristics of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4. [Figure 62] FIG. 62 shows the luminance-voltage characteristics of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4. [Figure 63] FIG. 63 shows the current-voltage characteristics of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4. [Figure 64] FIG. 64 shows the blue index-luminance characteristics of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4. [Figure 65] FIG. 65 shows the emission spectra of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4. [Figure 66] FIG. 66 is a graph showing the change in luminance with respect to the driving time of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4. In FIG. [Figure 67] FIG. 67 is a graph showing the change in luminance with respect to the driving time of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. In FIG. [Figure 68] Figure 68 shows the results of measuring the refractive index of mmtBumTPchPAF-02, mmtBumTPoFBi-02, and PCBBiF. [Figure 69] FIG. 69 shows the luminance-current density characteristics of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. [Figure 70] FIG. 70 shows the current efficiency-luminance characteristics of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. [Figure 71] FIG. 71 shows the luminance-voltage characteristics of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. [Figure 72] FIG. 72 shows the current-voltage characteristics of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. [Figure 73] FIG. 73 shows the blue index-luminance characteristics of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. [Figure 74] FIG. 74 shows the emission spectra of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. [Figure 75] FIG. 75 is a graph showing the change in luminance with respect to the driving time of the light-emitting device 11, the light-emitting device 12, and the comparative light-emitting device 5. In FIG. [Figure 76] FIG. 76 shows the current density-voltage characteristics of Device 1 and Device 2. [Figure 77]FIG. 77 shows the electric field strength dependence of the hole mobility of an organic compound according to one embodiment of the present invention. [Figure 78] Figure 78 is the 1H NMR chart of mmtBumTPoFBi-04. [Figure 79] Figure 79 shows the absorption spectrum and emission spectrum of mmtBumTPoFBi-04 in a toluene solution. [Figure 80] Figure 80 is the MS spectrum of mmtBumTPoFBi-04. [Figure 81] Figure 81 is a 1H NMR chart of mmtBumTPchPAF-04. [Figure 82] FIG. 82 shows the absorption spectrum and emission spectrum of mmtBumTPchPAF-04 in a toluene solution. [Figure 83] Figure 83 is the MS spectrum of mmtBumTPchPAF-04. [Figure 84] Figure 84 is the 1H NMR chart of mmtBumTPoFBi-05. [Figure 85] Figure 85 shows the absorption spectrum and emission spectrum of mmtBumTPoFBi-05 in a toluene solution. [Figure 86] Figure 86 is a 1H NMR chart of mmtBumTPchPAF-05. [Figure 87] FIG. 87 shows the absorption spectrum and emission spectrum of mmtBumTPchPAF-05 in a toluene solution. [Figure 88] Figure 88 is the 1H NMR chart of mmtBumQPoFBi. [Figure 89] Figure 89 is a 1H NMR chart of mmtBumQPchPAF. DETAILED DESCRIPTION OF THE INVENTION

[0072] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications may be made to the present invention. It should not be construed as being limited to the description of the embodiments.

[0073] (Embodiment 1) Among organic compounds with carrier transport properties that can be used in organic EL devices, One of the materials with low refractive index is 1,1-bis-(4-bis(4-methylphenyl)- The most well-known example is TAPC, which has a small refractive index. By using this material in the EL layer, it is possible to obtain a light-emitting device that exhibits high external quantum efficiency. Therefore, the use of TAPC can lead to light-emitting devices with good external quantum efficiency. It is expected that this will happen.

[0074] Usually, there is a trade-off between high carrier transport and low refractive index. The carrier transport properties of the compound are largely due to the presence of unsaturated bonds. This is because organic compounds with a high content of TAPC tend to have a high refractive index. It is a material that has an excellent balance of high performance and low refractive index. In compounds with a 1,1-disubstituted cyclohexane structure like C, the Since two bulky substituents are inserted on one carbon, steric repulsion increases, and the molecule This leads to instability in the TAP itself, which is a problem in terms of reliability. C is a cyclohexane compound with a simple benzene ring, which is why it is a The glass transition temperature (Tg) was low, and there were problems with heat resistance.

[0075] One method to obtain highly heat-resistant and reliable hole transport materials is to use unsaturated carbonization. It is conceivable to introduce hydrogen groups, especially cyclic unsaturated hydrocarbon groups, into the molecule. In order to obtain a material with a low refractive index, it is preferable to introduce a substituent with a low molecular refraction into the molecule. Examples of the substituent include saturated hydrocarbon groups and cyclic saturated hydrocarbon groups.

[0076] In addition, the materials used as carrier transport materials in organic EL devices have high carrier transport properties. It is preferable that the compound has a skeleton, and among these, an aromatic amine skeleton is preferable because it has a high hole transporting property. In order to further improve the hole transport property, it is possible to consider introducing two amine skeletons. However, as with the above-mentioned TAPC, depending on the environment of the substituents placed around it, However, the diamine structure may be detrimental to reliability.

[0077] Overcoming the trade-off, it combines carrier transport, low refractive index, and high reliability. As a compound that can be used in the present invention, the inventors have investigated a compound that forms bonds with sp3 hybrid orbitals that constitute a saturated hydrocarbon group. In particular, we have found arylamine compounds in which the ratio of carbon atoms contained in the arylamine compounds is within a certain range. The diamine compounds have good reliability equivalent to that of conventional hole transport layer materials with normal refractive indexes. In addition, the arylamine compound is a material having the following structure: The number and position of the substituents (i.e., alkyl and cycloalkyl groups) containing carbon atoms By devising a suitable placement, it is possible to create a material with better properties.

[0078] That is, the organic compound of one embodiment of the present invention is an aryl group having at least one aromatic group. The aromatic group is a benzene compound having a first benzene ring, a second benzene ring, and a third benzene ring. The benzene rings are directly bonded in this order and have at least three alkyl groups. The aromatic group has at least three alkyl groups, which allows for a hole transport with a small refractive index. The alkyl group may be a group having 1 to 6 carbon atoms. An alkyl group is preferred. From the viewpoint of decreasing the refractive index, a chain alkyl group having two or more carbon atoms is preferred. From the viewpoint of ensuring carrier transportability, a chain alkyl group having 5 or less carbon atoms is preferable. In addition, the refractive index reducing effect is particularly pronounced when the alkyl group has a branched chain with three or more carbon atoms. Therefore, a chain alkyl group having 2 to 5 carbon atoms is particularly preferred, and a chain alkyl group having 3 to 5 carbon atoms is even more preferred. It is preferably a chain alkyl group having a branch with a prime number of 5. It is more preferable that:

[0079] The first benzene ring may further have a substituted or unsubstituted phenyl group. The second or third benzene ring may further contain a phenyl group substituted with an alkyl group. It may have.

[0080] Here, the aromatic group has a first benzene ring bonded to the nitrogen of the amine, and the first benzene ring Among the benzene ring, the second benzene ring, and the third benzene ring, two or more benzene rings are The carbon atoms at the 1st and 3rd positions of each are bonded to a substituent other than hydrogen. The 3- and 4-positions are preferably bonded to an alkyl group, a benzene ring, or the nitrogen of an amine. That is, two of the first benzene ring, the second benzene ring, and the third benzene ring The above benzene rings may each independently be connected to other benzene rings (e.g., the above-mentioned benzene rings) at the 1-position and the 3-position. Any one of the first to third benzene rings or the alkyl group described above is substituted. a benzene ring of a phenyl group attached thereto), an alkyl group (for example, at least three alkyl groups as described above), It is preferable that the nitrogen atom of the amine is bonded to the aryl group or the nitrogen atom of the amine. In one embodiment, the arylamine compound is an arylamine compound having electrical stability in a light-emitting device. From this viewpoint, triarylamine compounds are preferred. In terms of low refractive index and sublimation, monoamine compounds (i.e., compounds with three aryl groups) are preferred. It is preferred that there is only one amine nitrogen attached in the compound.

[0081] Also, in the first benzene ring, a carbon atom located meta to the carbon atom bonded to the nitrogen atom of the amine is If one of the carbon atoms has a substituent, the substituent may be a second benzene ring. Preferably, when two meta carbons have substituents, one is a second benzene ring; The other is preferably an alkyl group or a benzene ring having an alkyl group. In the second benzene ring, a carbon atom is located meta to the carbon atom bonded to the first benzene ring. If one of the carbon atoms has a substituent, the substituent may be a third benzene ring. Preferably, when two meta carbons have substituents, one is a third benzene ring; The other is preferably an alkyl group or a phenyl group substituted with an alkyl group. In the third benzene ring, a carbon atom is located meta to the carbon atom bonded to the second benzene ring. When the carbon atom has a substituent, the substituent is an alkyl group or a group substituted with an alkyl group. A phenyl group is preferred.

[0082] In addition, the alkyl groups that can be used as substituents on the second and third benzene rings are The alkyl-substituted phenyl group has an alkyl group substituted on at least one of the meta-carbon atoms. It is preferred that the alkyl group is substituted, and more preferred that the two meta-position carbon atoms have alkyl groups. In addition, even if two or more phenyl groups substituted with this alkyl group are bonded, the refractive index does not decrease. While the contribution to the lowering of the viscosity is low, the increase in molecular weight leads to a decrease in sublimation, so the second It is preferred that the ring be bonded to only one of the benzene ring and the third benzene ring.

[0083] The number of alkyl groups in the aromatic group may vary depending on the number of second and third benzene rings. When the phenyl ring has a phenyl group substituted with an alkyl group, the The number of alkyl groups is also included.

[0084] Furthermore, at least two of the first to third benzene rings are If it is bonded to the nitrogen of a benzene ring, alkyl group, or amine at the 1st and 3rd positions, The remaining benzene ring may have a substituent at any carbon atom.

[0085] In this way, two of the first benzene ring, the second benzene ring, and the third benzene ring The above benzene rings are substituted with other benzene rings or alkyl groups at the 1st and 3rd positions. By bonding to the benzene ring of a phenyl group, an alkyl group, or the nitrogen of an amine, This is preferable because it lowers the refractive index.

[0086] Also, the first to third benzene rings and the phenyl group substituted with an alkyl group All of the benzene rings in a ring, an alkyl group (e.g., any of the at least three alkyl groups described above), or an amino group; It is preferable that the first benzene is bonded to the nitrogen atom in order to lower the refractive index. The benzene ring in the ring to the third benzene ring and the phenyl group substituted with an alkyl group All of the benzene rings are connected to other benzene rings, aryl, and aryl groups, at the 1st, 3rd, and 5th carbon atoms. an alkyl group (e.g., any of the at least three alkyl groups described above), or a nitrogen atom of an amine; It is preferable that the carbon atom is bonded to the benzene ring and the other carbon atoms are unsubstituted, as this shortens the conjugation. The extension of the conjugation of the fluorine-containing compound reduces the adverse effects on light-emitting devices, such as the absorption of light in the visible region. It may also occur.

[0087] In addition, the second benzene ring or the third benzene ring has a phenyl group substituted with an alkyl group. In this case, it is preferable that the phenyl group has alkyl groups at the two meta positions, and further, It is preferable that the alkyl group is present at the two meta positions and the ortho and para positions are unsubstituted. .

[0088] The first benzene ring may further comprise a substituted or unsubstituted phenyl group, preferably an unsubstituted phenyl group. It is preferable to have a phenyl group to prevent shielding of the amine nitrogen. The fact that the ortho- or unsubstituted phenyl group is bonded to the first benzene ring facilitates carrier transport. When the substituted or unsubstituted phenyl group has a substituent, The substituent is intended to be an alkyl group.

[0089] Furthermore, the arylamine compound has a second aromatic group, which improves hole transport properties. The second aromatic group is preferably a substituted or unsubstituted monocyclic or substituted or unsubstituted aromatic group. is preferably an unsubstituted fused ring skeleton of 3 or less rings in order to improve hole transport properties. This keeps the refractive index low, since the refractive index tends to increase as the number of rings in the case increases. Similarly, when the number of rings in the fused ring skeleton increases, the absorption and emission of light in the visible region also increases. Therefore, the material can be one that is less affected by absorption and emission. The second aromatic group has a fused ring skeleton having 6 carbon atoms in order to maintain a low refractive index. The aromatic group that can be used as the second aromatic group is preferably Specifically, the rings include benzene rings, naphthalene rings, fluorene rings, and acenaphthylene rings. In particular, the second aromatic group is preferably a fluoro group, since it has good hole transport properties. Preferably, the compound contains an olefin ring, and more preferably, it is a fluorene ring. The aromatic group is a dimethylfluorenyl group, which improves the durability of the material. In particular, it is preferable that the dimethylfluorenyl group has no other substituents, because this is effective for hole transport. The second aromatic group is preferably the arylamine group. The direct bond to the amine nitrogen of the compound makes the HOMO level of the molecule shallower. This is preferable because it facilitates the transfer of holes.

[0090] The alkyl group mentioned above is preferably an alkyl group having 1 to 6 carbon atoms. From the viewpoint of reducing the refractive index, a chain alkyl group having two or more carbon atoms is preferable, and the carrier transport property is ensured. From the viewpoint of maintaining the refractive index, a chain alkyl group having 5 or less carbon atoms is preferable. The alkyl group having 1 to 3 carbon atoms is a branched chain alkyl group having 3 or more carbon atoms. The alkyl group having 6 carbon atoms is preferably a chain alkyl group having 2 to 5 carbon atoms, and more preferably a chain alkyl group having 3 carbon atoms. A branched chain alkyl group having 1 to 6 carbon atoms is more preferred. The alkyl group includes methyl, ethyl, propyl, isopropyl, butyl, and s ec-butyl, isobutyl, tert-butyl, pentyl and hexyl groups are preferred. A tert-butyl group is particularly preferred.

[0091] The arylamine compound preferably has a third aromatic group. The aromatic group is preferably a group having 1 to 3 substituted or unsubstituted benzene rings. When the third aromatic group has two or three benzene rings, the two or three Preferably, the three benzene rings are bonded to each other as substituents. The aromatic group is a phenyl group, a biphenyl group, a terphenyl group, or a naphthylphenyl group. It is preferable that the third aromatic group is a biphenyl group bonded at the ortho position. In addition, it is preferable that one or more of the 1 to 3 benzene rings is / are formed in the above-mentioned manner, since the hole transport property is good. When one or more of the groups have a substituent, the substituent may be an alkyl group having 1 to 6 carbon atoms. A cycloalkyl group having 5 to 12 carbon atoms, etc. can be used. In order to reduce the rate, the alkyl group having 1 to 6 carbon atoms is preferably a chain alkyl group having 2 or more carbon atoms. is preferable, and from the viewpoint of ensuring carrier transportability, a chain alkyl group having 5 or less carbon atoms is preferable. Moreover, the refractive index-reducing effect is most pronounced with branched chain alkyl groups having three 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. An alkyl group is preferred, and a branched chain alkyl group having 3 to 5 carbon atoms is more preferred. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, and a propyl group. , isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, A pentyl group is preferred, and a tert-butyl group is particularly preferred. Examples of cycloalkyl groups having 12 carbon atoms include cyclohexyl and 4-methylcyclohexyl. group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, decahedron A cyclonaphthyl group, a cycloundecyl group, a cyclododecyl group, etc. can be used. A cycloalkyl group having 6 or more carbon atoms is preferred for lowering the refractive index, and cyclohexyl is particularly preferred. The cyclododecyl group and the cyclododecyl group are preferred.

[0092] 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 a triarylamine compound from the viewpoint of hole-transport properties. Preferably, the compound is a diamine compound.

[0093] The arylamine compound according to one embodiment of the present invention having the above-described structure has a wavelength of 455 nm or longer. The refractive index of ordinary light in the entire range of light from 1.5 to 1.75, and the wavelength of 63 A compound with a very low refractive index, with an ordinary refractive index of 1.45 or more and 1.70 or less for 3 nm light If anisotropy occurs in the material, the refractive index for ordinary light and The refractive index for extraordinary light may be different. If the thin film to be measured is in such a state, By performing a tropospheric analysis, the refractive index is separated into ordinary and extraordinary light and each refractive index is calculated. In this specification, the materials measured have ordinary and extraordinary refractive indices. When both exist, the ordinary refractive index is used as the index.

[0094] In addition, the arylamine compound according to one embodiment of the present invention having the above-described structure exhibits a glass transition In addition, a high heat resistance of 100° C. or more can be realized. In this case, the glass transition temperature is preferably 110°C or higher, more preferably 120°C or higher. can.

[0095] In addition, by forming the film by vapor deposition, it is easy to achieve the low refractive index and high heat resistance described above. Therefore, the molecular weight is preferably 400 or more and 1,100 or less.

[0096] The arylamine compound having the above-described structure has a hole transporting property and a small refractive index. As it is an organic compound, it can be used as a material for the hole transport layer or hole injection layer of an organic EL device. The hole transport layer material or the hole injection layer material can be suitably used as the hole transport layer material or the hole injection layer material. The organic EL device using the above has a hole transport layer and a hole injection layer with a small refractive index. Therefore, the luminous efficiency, i.e., the external quantum efficiency, current efficiency, and blue index are high. Furthermore, a device can be fabricated using the hole transport layer material or the hole injection layer material. The organic EL device is characterized in that the hole transport layer material or the hole injection layer material is an arylamine. It is preferable that the compound is a compound having a limited number of aromatic groups bonded to a saturated hydrocarbon group. It is possible to improve the stability of molecules by reducing the steric repulsion. This makes it possible to provide a light-emitting device with a long life.

[0097] Among the above arylamine compounds, the organic compound represented by the following general formula (G1) Particularly preferred.

[0098] [ka]

[0099] However, in the above general formula (G1), Ar 1 is a substituted or unsubstituted benzene ring, or It represents a substituent in which two or three substituted or unsubstituted benzene rings are bonded to each other. 1 Specific examples of the alkyl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthylphenyl group, and the like. The phenyl group is used to lower the refractive index and maintain the hole transport property of the nitrogen atom. The aryl group is particularly preferred.

[0100] Also, R 11 ~R 15 One of the substituents is represented by the general formula (g1), and the rest are each each independently selected from hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; The substituted or unsubstituted phenyl group represents an unsubstituted phenyl group. When the group has a substituent, it has 1 to 6 carbon atoms. .

[0101] In addition, in the general formula (g1), R 21 ~R 25 One of them is represented by the above general formula (g2). The remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a carbon atom, It represents any one of phenyl groups substituted with an alkyl group having 1 to 6 carbon atoms.

[0102] In addition, in the general formula (g2), R 31 ~R 35 are each independently hydrogen, a group having 1 or more carbon atoms, alkyl groups having up to 6 carbon atoms, and phenyl groups substituted with alkyl groups having 1 to 6 carbon atoms Represents one of the following.

[0103] where R 11 ~R 15 , R 21 ~R 25 and R 31 ~R 35 At least At least three of the alkyl groups are alkyl groups having 1 to 6 carbon atoms. The arylamine compound represented by the formula (I) is an arylamine compound having a low refractive index. can be done.

[0104] Furthermore, R 11 ~R 15 The number of substituted or unsubstituted phenyl groups in

[0105] Also, R 21 ~R 25 and R 31 ~R 35 Alkyl groups having 1 to 6 carbon atoms The number of phenyl groups substituted with phenyl groups is 1 or less, i.e., R 21 ~R 25 and R 31 ~R 35 Among these, the number of phenyl groups substituted with alkyl groups having 1 to 6 carbon atoms is 1 or 0. It shall be as it is.

[0106] In addition, R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 Three sets of In at least two of the combinations, at least one R is other than hydrogen. That is, R 12 and R 14 a benzene ring having R 2 2 and R 24 a benzene ring having R32 and R 34 A benzene ring having In other words, in two or more benzene rings, at least one of the meta-position carbon atoms of each ring is hydrogen. In other words, it has a substituent. 12 , R 14 , R 22 , R 24 of at least one of which is a substituent other than hydrogen, and R 32 and R 34 At least one of The substituents other than hydrogen are preferred.

[0107] Also, R 6 , R 7 and R 8 each independently represents an alkyl group having 1 to 4 carbon atoms, m represents an integer of 0 to 4. When m is 2 or more, a plurality of R 8 are the same for each may also be different.

[0108] Specific examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, Examples of groups that can be mentioned include butyl, sec-butyl, and isobutyl groups. Particularly preferred is a tert-butyl group.

[0109] In addition, the above-mentioned substituted or unsubstituted benzene ring or substituted or unsubstituted phenyl group may be substituted In the case where the group is present, the substituent is an alkyl group having 1 to 6 carbon atoms, an alkyl group having 5 or more carbon atoms, or Cycloalkyl groups containing up to 12 carbon atoms can be used.

[0110] As the alkyl group having 1 to 6 carbon atoms, from the viewpoint of decreasing the refractive index, an alkyl group having 2 or more carbon atoms is preferred. A chain alkyl group is preferred, and from the viewpoint of ensuring carrier transportability, a chain alkyl group having 5 or less carbon atoms is preferred. Furthermore, a branched chain having 3 or more carbon atoms is preferred for reducing the refractive index. That is, the alkyl group having 1 to 6 carbon atoms is an alkyl group having 2 to 6 carbon atoms. A chain alkyl group having 5 carbon atoms is preferred, and a branched chain alkyl group having 3 to 5 carbon atoms is preferred. Specific examples of alkyl groups having 1 to 6 carbon atoms include methyl groups. , ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group , tert-butyl group, pentyl group, hexyl group, etc., are particularly preferred. is a tert-butyl group.

[0111] Specific examples of the cycloalkyl group having 5 to 12 carbon atoms include cyclohexyl methyl ... Cyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group cyclodecyl, decahydronaphthyl, cycloundecyl, and cyclododecyl groups Although a silyl group can be used, a cycloalkyl group having 6 or more carbon atoms is preferred for lowering the refractive index. In particular, cyclohexyl and cyclododecyl groups are preferred.

[0112] In addition, in the general formula (G1), Ar 1 is two or three substituted or unsubstituted benzoates It is preferable that the Zhen rings are bonded to each other as a substituent, that is, a group represented by the following general formula (G2): It is preferable that the arylamine compound is an arylamine compound represented by the following formula:

[0113] [ka]

[0114] In the above general formula (G2), p and r each independently represent 1 or 2, and p+ r is 2 or 3. When p is 2, the number of substituents on the two phenylene groups is The type, number of substituents and bond positions may be the same or different, and when r is 2, In this case, the types of substituents, the number of substituents, and the positions of the bonds of the two phenyl groups must be the same. It is preferable that p is 1 and r is 1.

[0115] Also, R 41 ~R 45 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, It represents any one of cycloalkyl groups having 5 to 12 carbon atoms.

[0116] Also, R 9 represents an alkyl group having 1 to 4 carbon atoms, n represents an integer of 0 to 4, and n is an integer of 2 or more. If above, multiple R 9 may be the same or different. It is preferable that

[0117] Specific examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, butyl, isopropyl, sec-butyl, isobutyl and tert-butyl Examples of the alkyl group include a tert-butyl group, and a tert-butyl group is particularly preferred.

[0118] As the alkyl group having 1 to 6 carbon atoms, from the viewpoint of decreasing the refractive index, an alkyl group having 2 or more carbon atoms is preferred. A chain alkyl group is preferred, and from the viewpoint of ensuring carrier transportability, a chain alkyl group having 5 or less carbon atoms is preferred. Furthermore, a branched chain having 3 or more carbon atoms is preferred for reducing the refractive index. That is, the alkyl group having 1 to 6 carbon atoms is an alkyl group having 2 to 6 carbon atoms. A chain alkyl group having 5 carbon atoms is preferred, and a branched chain alkyl group having 3 to 5 carbon atoms is preferred. Specific examples of alkyl groups having 1 to 6 carbon atoms include methyl groups. , ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group , tert-butyl group, pentyl group, hexyl group, etc., are particularly preferred. is a tert-butyl group.

[0119] Specific examples of the cycloalkyl group having 5 to 12 carbon atoms include cyclohexyl methyl ... Cyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group cyclodecyl, decahydronaphthyl, cycloundecyl, and cyclododecyl groups Although a silyl group can be used, a cycloalkyl group having 6 or more carbon atoms is preferred for lowering the refractive index. In particular, cyclohexyl and cyclododecyl groups are preferred.

[0120] In addition, R 6 , R 7 , R 11 ~R 15 , R 21 ~R 25 , R 31 ~R 35 , with respect to m Since the general formula (G1) is the same as that of the general formula (G1), the explanation will be omitted.

[0121] In addition, in the general formula (G1), Ar 1 is one substituted or unsubstituted benzene ring That is, it is preferable that the compound is an arylamine compound represented by the following general formula (G3): It is preferable that

[0122] [ka]

[0123] However, in the above general formula (G3), R 1 ~R5 are each independently hydrogen, a group having 1 to 10 carbon atoms, Alkyl groups having 6 carbon atoms, cycloalkyl groups having 5 to 12 carbon atoms, and substituted or unsubstituted alkyl groups having 6 to 12 carbon atoms. represents any one of the substituted phenyl groups.

[0124] In the above general formula (G3), R 1 ~R 5 Among them, R 3 is a cyclohexyl group Preferably, the remainder are all hydrogen atoms. 1 ~R 5 Among them, R 1 is unsubstituted The remaining phenyl groups are hydrogen atoms, which is preferable because it improves hole transport properties. stomach.

[0125] In addition, when the substituted or unsubstituted phenyl group has a substituent, the substituent is, for example, The alkyl group having 1 to 6 carbon atoms and the cycloalkyl group having 5 to 12 carbon atoms are used. It is possible.

[0126] As the alkyl group having 1 to 6 carbon atoms, from the viewpoint of decreasing the refractive index, an alkyl group having 2 or more carbon atoms is preferred. A chain alkyl group is preferred, and from the viewpoint of ensuring carrier transportability, a chain alkyl group having 5 or less carbon atoms is preferred. Furthermore, a branched chain having 3 or more carbon atoms is preferred for reducing the refractive index. That is, the alkyl group having 1 to 6 carbon atoms is an alkyl group having 2 to 6 carbon atoms. A chain alkyl group having 5 carbon atoms is preferred, and a branched chain alkyl group having 3 to 5 carbon atoms is preferred. Specific examples of alkyl groups having 1 to 6 carbon atoms include methyl groups. , ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group , tert-butyl group, pentyl group, hexyl group, etc., are particularly preferred. is a tert-butyl group.

[0127] Specific examples of the cycloalkyl group having 5 to 12 carbon atoms include cyclohexyl methyl ... Cyl group, 4-methylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group cyclodecyl, decahydronaphthyl, cycloundecyl, and cyclododecyl groups Although a silyl group can be used, a cycloalkyl group having 6 or more carbon atoms is preferred for lowering the refractive index. In particular, cyclohexyl and cyclododecyl groups are preferred.

[0128] In addition, R 6 , R 7 , R 11 ~R 15 , R 21 ~R 25 , R 31 ~R 35 , with respect to m Since the general formula (G1) is the same as that of the general formula (G1), the explanation will be omitted.

[0129] In the arylamine compounds represented by the above general formulas (G1) to (G3), m is It is preferably 0.

[0130] In the arylamine compounds represented by the above general formulas (G1) to (G3), R 11 ~R 15 , R 21 ~R 25 and R 31 ~R 35 Among them, R 12 , R 14 , R 22 , R 32 and R 34 is preferably a substituent other than hydrogen, and the remainder is preferably hydrogen. Also, R 12 is a substituent represented by the general formula (g1), and R 22 is represented by the general formula (g 2) is preferably a substituent represented by R 14 , R 32 and R 34 But A rt-butyl group is preferred.

[0131] The arylamine compound according to one embodiment of the present invention having the above-described structure has a wavelength of 455 nm or longer. The refractive index of ordinary light in the entire range of light from 1.5 to 1.75, and the wavelength of 63 A compound with a very low refractive index, with an ordinary refractive index of 1.45 or more and 1.70 or less for 3 nm light It is possible to do so.

[0132] The organic compound of one embodiment of the present invention having the above structure has a favorable hole-transport property and a refractive index. Since it is an organic compound with a small refractive index, it is suitable as a material for the hole transport layer of an organic EL device or as a hole transport layer. The compound can be suitably used as a material for a hole injection layer. Organic EL devices using injection layer materials have hole transport layers and hole injection layers with low refractive indexes. Therefore, the luminous efficiency, i.e., the external quantum efficiency, current efficiency, and blue index This can result in a light-emitting device with high performance.

[0133] Specific examples of organic compounds having the above structure are shown below.

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137]

change

[0138]

change

[0139]

change

[0140]

change

[0141]

change

[0142]

change

[0143]

change

[0144]

change

[0145]

change

[0146]

change

[0147]

change

[0148]

change

[0149]

change

[0150]

change

[0151]

change

[0152]

change

[0153]

change

[0154]

change

[0155]

change

[0156]

change

[0157]

change

[0158] [ka]

[0159] [ka]

[0160] [ka]

[0161] [ka]

[0162] [ka]

[0163] [ka]

[0164] (Embodiment 2) FIG. 1A shows a light-emitting device according to one embodiment of the present invention. The device has a first electrode 101, a second electrode 102, and an EL layer 103. The organic compound shown in Embodiment Mode 1 is used.

[0165] The EL layer 103 has a light-emitting layer 113, a hole-injection layer 111 and / or a hole-transport layer. The light-emitting layer 113 may include a light-emitting material. The light-emitting device emits light from the light-emitting material. The light-emitting layer 113 contains a host material and The organic compound according to one embodiment of the present invention described in Embodiment 1 may contain other materials. is contained in the light-emitting layer 113, the hole transport layer 112, or the hole injection layer 1 It doesn't matter if it's included in 11 or any of them.

[0166] In addition to these, an electron transport layer 114 and an electron injection layer 115 are also shown in FIG. 1(A). However, the configuration of the light-emitting device is not limited to these.

[0167] The organic compound has good hole transport properties and is therefore effective for use in the hole transport layer 112. In addition, the organic compound of one embodiment of the present invention is a compound obtained by mixing the organic compound with an acceptor substance. The film thus obtained can be used as the hole injection layer 111.

[0168] Furthermore, the organic compound of one embodiment of the present invention can also be used as a host material. Furthermore, by co-evaporating an electron transport material with the electron transport material, the electron transport material and the hole transport material It is also possible to form an exciplex by using a material having an appropriate emission wavelength. By forming the luminescent material, efficient energy transfer to the luminescent material is achieved, resulting in high efficiency and long life. It is possible to provide a light-emitting device that has life.

[0169] Since the organic compound according to one embodiment of the present invention has a low refractive index, it is possible to form an organic compound in an EL layer. By using this as a part, a light emitting device with good external quantum efficiency can be obtained.

[0170] Next, examples of the detailed structure and materials of the light-emitting device will be described. As described above, the light-emitting device has a pair of electrodes, a first electrode 101 and a second electrode 102, between which a light-emitting element is formed. The EL layer 103 is made up of a plurality of layers, and the EL layer 103 has a plurality of layers. The organic compound disclosed in the first embodiment is included.

[0171] The first electrode 101 is made of a metal, alloy, or conductive material having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a compound such as a carboxylic acid or a mixture thereof. For example, indium tin oxide (ITO), silicon Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon or silicon oxide , indium oxide containing tungsten oxide and zinc oxide (IWZO), etc. These conductive metal oxide films are usually formed by sputtering, but they can also be formed by sol-gel deposition. It is also possible to fabricate it by applying a method such as a quartz crystal process. Zinc was produced using a target containing 1 to 20 wt% zinc oxide added to indium oxide. Also, tungsten oxide and zinc oxide are used. The indium oxide (IWZO) contains 0.5% tungsten oxide relative to the indium oxide. Sputtering was performed using a target containing 5-5 wt% of zinc oxide and 0.1-1 wt% of zinc oxide. It can also be formed by the method. In addition, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Nitrides of metallic materials (e.g., titanium nitride), copper (Cu), palladium (Pd), or Graphene can also be used. By using it in the layer 103 that is in contact with the first electrode 101, the electric field can be controlled regardless of the work function. You will be able to select the pole material.

[0172] The EL layer 103 preferably has a laminated structure, but there are no particular limitations on the laminated structure. There is no specific definition, and the layer may be a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier blocking layer, an excitation layer, or a Various layer structures such as a charge blocking layer and a charge generating layer can be applied. As shown in FIG. 1(A), the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113 are In addition, the structure including the electron transport layer 114 and the electron injection layer 115 and the structure including the electron transport layer 114 and the electron injection layer 115 as shown in FIG. In addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113, the electron transport layer 114 and a structure having an electron injection layer 115 and a charge generation layer 116 will be described. The materials constituting each layer are specifically shown below.

[0173] The hole injection layer 111 is a layer containing a substance having acceptor properties. The substance can be either an organic compound or an inorganic compound.

[0174] Acceptor substances include compounds with electron-withdrawing groups (halogen groups and cyano groups). The compound can be used, for example, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene. Quinodimethane (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), 2-(7-dicyanomethylene-1,3,4,5,6,8,9 , 10-octafluoro-7H-pyren-2-ylidene)malononitrile, etc. In particular, when an electron-withdrawing group is attached to a condensed aromatic ring with multiple heteroatoms, such as HAT-CN, The bonded compound is thermally stable and is therefore preferred. Radialene derivatives containing halogen or cyano groups such as Specifically, α,α',α''-1,2,3-cyclopropanetriyl Lidentris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile] , α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dichloro b-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α, α',α''-1,2,3-Cyclopropanetriylidenetris[2,3,4,5,6- Pentafluorobenzeneacetonitrile, etc. Acceptor substances In addition to the organic compounds mentioned above, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. Phthalocyanines such as phthalocyanine (abbreviated as HPc) and copper phthalocyanine (CuPc) The complex compound, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl N,N'-bis[4-[bis(3-methylphenyl)amino]biphenyl (abbreviation: DPAB), (phenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4, Aromatic amine compounds such as 4'-diamine (abbreviated as DNTPD) or poly(3,4-ene) (ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) The hole injection layer 111 can also be formed from a polymer or the like. The material attracts electrons from the adjacent hole transport layer (or hole transport material) by applying an electric field. It can be removed.

[0175] The hole injection layer 111 may be formed by adding the above-mentioned acceptor substance to a material having a hole transporting property. It is also possible to use a composite material in which a material having hole transport properties is combined with an acceptor material. By using a composite material containing a metal, it is possible to select a material to form an electrode regardless of its work function. In other words, the first electrode 101 can be made of not only a material with a large work function but also a material with a specific It becomes possible to use materials with small coefficients of thermal conductivity.

[0176] Examples of materials having hole transport properties that can be used in the composite material include aromatic amine compounds and carbazole. Derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. Various organic compounds having hole transport properties can be used for the composite material. The material is 1 x 10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. The following describes materials that can be used as the material having hole transport properties in the composite material. Specific examples of organic compounds are listed below.

[0177] 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 (abbreviation Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl Carbazole derivatives Specific examples of the compound include 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl]carbazol-3-yl ... Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol PCzPCA2 (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1 ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri bis[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenylanthracen-9-yl)phenyl]-9H-carbazole (abbreviation: CzP A), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetrafluoroethylene Examples of aromatic hydrocarbons that can be used include 2-tert-butylphenylbenzene. t-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2 -tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3 ,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl- 9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9, 10-Di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene Helical anthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuA nth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA ), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]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(1-naphthyl)anthracene Methyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10, 10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl) 10,10'-bis[(2,3,4,5,6-pentanthryl Phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene , perylene, 2,5,8,11-tetra(tert-butyl)perylene, and the like. In addition, pentacene, coronene, etc. can also be used. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2, 2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2, 2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), etc. Note that the organic compound of one embodiment of the present invention can also be used.

[0178] In addition, poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenyl) PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine] N'-phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. Cut.

[0179] Materials having hole transport properties that can be used in composite materials include carbazole skeletons, dibenzofuran skeletons, and It has either an orchid skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. More preferred are those having a substituent containing a dibenzofuran ring or a dibenzothiophene ring. aromatic amines having a naphthalene ring, aromatic monoamines having a 9-fluorenyl group may be an aromatic monoamine bonded to the nitrogen of the amine via an arylene group. The second organic compound is a substance having an N,N-bis(4-biphenyl)amino group. If the above-mentioned condition is satisfied, a light-emitting device having a long life can be produced, which is preferable. Specific examples of the second organic compound include N-(4-biphenyl)-6,N-diphenyl Benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N -Bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8 -amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[ 1,2-d]furan-8-yl-4''-phenyltriphenylamine (abbreviation: BnfB B1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan -6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[ b]Naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N- Bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]phenyl N-[4-(dibenzyl)]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), [N-(4-(benzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine BBAβNB, 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyl Phenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4'' -(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB) , 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenyla amine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4''-(7-phenyl BBAPβNB-03, 4,4'-naphthyl-2-yltriphenylamine -Diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation :BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2 -yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl BBAβ NαNB), 4,4'-diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenyl Phenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'- (2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyl mTPBiAβNBi, 4-(4-biphenylyl)-4 '-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (α NBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl) Biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4- (3-phenyl-9H-carbazol-9-yl)phenyl]tris(1,1'-biphenyl) 4-[4'-(carbazol-4-yl)amine (abbreviation: YGTBi1BP-02), [4'-(2-naphthyl-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyl Triphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbamoyl) N-[4-(1-naphthyl)phenyl]-9,9' -Spirobi(9H-fluorene)-2-amine (abbreviation: PCBNBSF), N,N-bis ([1,1'-biphenyl]-4-yl)-9,9'-spirobi[9H-fluorene]- 2-Amine (abbreviation: BBASF), N,N-bis(1,1'-biphenyl-4-yl)- 9,9'-Spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N -(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene- 2-yl)-9,9'-spirobi(9H-fluorene)-4-amine (abbreviation: oFBiS F), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl ) Dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl] N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthyl Fluoromethylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluorene) 4-phenyl-3'-(9-yl)triphenylamine (abbreviation: BPAFLP), -phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4- Phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenyl Amine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carba (3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl 4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carba 4,4'-di(1-naphthyl)triphenylamine (abbreviation: PCBANB), (9-phenyl-9H-carbazol-3-yl)triphenylamine PCBNBB, N-phenyl-N-[4-(9-phenyl-9H-carbazoline 9,9'-spirobi[9H-fluoren]-2-amine( Abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl- N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoro PCBBiF, N,N-bis(9,9-dimethyl-9H-fluoren-2-amine) fluoren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N- Bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H- Fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-amine) N,N-bis(9,9-diyl)-9,9'-spirobi-9H-fluoren-2-amine Methyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-1- amines and the like.

[0180] The hole transport material used in the composite material has a HOMO level of -5.7 eV. It is more preferable that the HOMO level is a relatively deep one of -5.4 eV or more. The hole-transporting material used in the composite material has a relatively deep HOMO level. This facilitates the injection of holes into the hole transport layer 112, and also makes it possible to produce a light-emitting device with a long life. This makes it easier to obtain the vise.

[0181] Note that the monoamine compound described in Embodiment 1 is also a material having a hole-transporting property. It can be suitably used as a material for a hole injection layer used in a composite material. By using the monoamine compound described above, a layer with a low refractive index is formed inside the EL layer 103. This can improve the external quantum efficiency of the light-emitting device.

[0182] The composite material may further contain a fluoride of an alkali metal or an alkaline earth metal (preferably or the atomic ratio of fluorine atoms in the layer is 20% or more), the refractive index of the layer is This also allows a layer with a low refractive index to be formed inside the EL layer 103. This can improve the external quantum efficiency of the light-emitting device.

[0183] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. In addition, organic compounds with acceptor properties can be easily vapor-deposited. It is an easy-to-use material because it is easy to form a film.

[0184] The hole transport layer 112 is formed by including a material having a hole transport property. The material is 1 x 10 -6 cm 2It is preferable that the hole mobility is equal to or higher than / Vs. The monoamine compound described in the first embodiment is a material having hole transport properties. Therefore, the hole transport layer 112 can be suitably used as a material for the hole transport layer 112. Preferably, the hole transport layer 112 contains the monoamine compound described in 1. It is more preferable that the composition is composed of the monoamine compound described in the first embodiment. By including the monoamine compound described in 1 in the hole transport layer 112, A layer with a low refractive index can be formed in the region, improving the external quantum efficiency of the light-emitting device. This makes it possible to:

[0185] When a material other than the monoamine compound described in the first embodiment is used for the hole transport layer 112, The material having the hole transport property is 4,4'-bis[N-(1-naphthyl)-N-phenyl]- N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD ), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl 4-phenyl-4'-(9-phenylfluoro)biphenyl (abbreviation: BSPB), 4-phenyl-3'-(phenyl-9-yl)triphenylamine (abbreviation: BPAFLP), 9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4 -phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine PCBA1BP, 4,4'-diphenyl-4''-(9-phenyl-9H- Carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1- naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine PCBANB, 4,4'-di(1-naphthyl)-4''-(9-phenyl- 9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9- Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl) phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-( 9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H -fluorene]-2-amine (abbreviation: PCBASF) and other compounds with aromatic amine skeletons compounds, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di( N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenyl phenyl) 3,3'-bis(9-phenyl)-9-phenylcarbazole (abbreviation: CzTP), Compounds with a carbazole skeleton, such as PCCP (9H-carbazole) , 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (Abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H- Fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) , 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyl Compounds with a thiophene skeleton, such as dibenzothiophene (abbreviation: DBTFLP-IV) and 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) ( Abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9- (I)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) Among the above, compounds having an aromatic amine skeleton are preferred. Compounds having a carbazole skeleton and compounds having a high reliability and high hole transport property are also used. It is preferable because it contributes to reducing the driving voltage. The materials having hole transport properties that can be used for the hole transport layer 112 may also be used as materials for the hole transport layer 112. It can be suitably used.

[0186] The light-emitting layer 113 contains a light-emitting substance and a host material. It may also be a laminate of two layers with different compositions.

[0187] The emitting material may be a fluorescent material, a phosphorescent material, or a thermally activated delayed fluorescence (T The material may be a material that exhibits ADF or other luminescent material. In one embodiment, the light-emitting layer 113 is a layer that exhibits fluorescent emission, particularly a layer that exhibits blue fluorescent emission. It can be suitably applied in some cases.

[0188] In the light-emitting layer 113, materials that can be used as fluorescent materials include, for example: Examples include the following: Other fluorescent materials can also be used.

[0189] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine PAP2BPy, 5,6-bis[4'-(10-phenyl-9-anthracene] N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene 9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn ), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-di Phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazo (4'-(10-phenyl-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation Name: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl N,9-diphenyl-2-anthryltriphenylamine (abbreviation: 2YGAPPA) N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole -3-amine (abbreviation: PCAPA), Perylene, 2,5,8,11-tetra-tert- Butylperylene (TBP), 4-(10-phenyl-9-anthryl)-4'-( 9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAP) A), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1 -phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine]( Abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2- anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'- N,N,N',N-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) ',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene -2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N-(9,1 0-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-a amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)] )-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N' -Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10 -bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis( 1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl] N,N,nyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), 9-Triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 545 T,N,N'-Diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bi Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl 6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizidine] 4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitri (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine -9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetramethyl- tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pi N,N'-diphenyl-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphthyl) 1,6BnfAPrn-03, 3, 10-Bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamine] 3,10PCA2N bf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenyl 3,10F rA2Nbf(IV)-02). In particular, 1,6FLPAPrn and 1,6 Pyrene diamine compounds such as mMemFLPAPrn and 1,6BnfAPrn-03 Representative condensed aromatic diamine compounds have high hole trapping properties and are highly effective in luminous efficiency and reliability. It is preferable because it is superior.

[0190] In the light-emitting layer 113, when a phosphorescent material is used as the light-emitting material, Examples of suitable materials include the following:

[0191] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl Iridium(III) (abbreviation: [Ir(Mpt z)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3 b) Organometallic iridium complexes with a 4H-triazole skeleton, such as 3), and tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazol- Zolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1 -methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(PrptZ1-Me)3]) Organometallic iridium complexes with fac-tris[(1-2,6-diisopropyl phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimide Dazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmp and organometallic iridium complexes having an imidazole skeleton, such as impt-Me)3). Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4' ,6'-difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) picolinate bis(2-[3',5'-bis(trifluoromethyl) fluoride] (abbreviation: FIrpic), Phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri[ Ginat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIr(ac Organometallic intermetallic compounds with phenylpyridine derivatives having electron-withdrawing groups such as ac)) as ligands These compounds exhibit blue phosphorescence, with an emission wavelength of 440 nm. It is a compound that has an emission peak at 520 nm.

[0192] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)yl Ir(tBuppm)3), (acetylacetonato)bis(Ir(tBuppm)3) (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpiperidinyl] [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) (abbreviation: [Ir(dppm)2(acac)]) Organic metal iridium complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl) Rupirazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine) Dinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinium) Nat-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2- Phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzyl) Tribenzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris (2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetone Pyridine skeleton-containing compounds such as setonate (abbreviation: [Ir(pq)2(acac)]) In addition to organometallic iridium complexes, tris(acetylacetonato)(monophenanthroline)tetrahydrogen Rare earth metals such as rubium(III) (abbreviated as [Tb(acac)3(Phen)]) These are mainly compounds that exhibit green phosphorescence, with wavelengths ranging from 500 nm to 6 The emission peak is at 100 nm. The body is particularly preferred because it is remarkably excellent in reliability and luminous efficiency.

[0193] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] Nato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridine Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organogold compounds with pyrimidine skeletons, such as [Ir(d1npm)2(dpm)] iridium complexes of the genus acetylacetonatobis(2,3,5-triphenylpyrazine) Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III)(abbreviation Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fd pq)2(acac)]), and organometallic iridium complexes with pyrazine skeletons such as Tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir (piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (II I) Pyridyl acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with iridium skeletons, 2,3,7,8,12,13,17,18 -octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monophenyl Anthroline) europium(III) (abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthate) (Troline) europium(III) (abbreviation: [Eu(TTA)3(Phen)]) These are compounds that exhibit red phosphorescence and are The emission peak is between 0 nm and 700 nm. The rhodium complex emits red light with good chromaticity.

[0194] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting substances may be selected and used. stomach.

[0195] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin. Derivatives of magnesium (Mg), zinc (Zn), cadmium, etc. can also be used. (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d) and the like. Examples of the metal-containing porphyrin include: For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Copropor Phyllin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiop Porphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -platinum chloride complex (PtCl2OEP) and the like.

[0196] [ka]

[0197] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-4-phenyl-4-methyl-4-phenyl ... (phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviation: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT zn), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl phenyl]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPT zn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-difluoro Phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl -5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1, 2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-azabicyclo[4.2.1.2]phenyl) cridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[ 4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9 π-electron-rich heteroaromatic rings such as '-anthracene]-10'-one (abbreviation: ACRSA) and a heterocyclic compound having one or both of a π-electron-deficient heteroaromatic ring can also be used. Since the heterocyclic compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, Among them, those having a π-electron-deficient heteroaromatic ring are preferred because they have high electron transporting properties and hole transporting properties. Among the skeletons that have pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridine skeleton, The tetraazine skeleton and the triazine skeleton are preferred because they are stable and reliable. Benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrazine skeleton, The zothienopyrazine skeleton is preferred because it has high acceptor properties and good reliability. Among the skeletons with electron-rich heteroaromatic rings, acridine skeleton, phenoxazine skeleton, fluorine skeleton, The ethenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable. It is preferable that the furan skeleton has at least one of the above skeletons. The dibenzofuran skeleton is used for the thiophene skeleton, and the dibenzothiophene skeleton is used for the thiophene skeleton. The pyrrole skeleton is preferably an indole skeleton, a carbazole skeleton, or an indole skeleton. Carbazole skeleton, bicarbazole skeleton, 3-(9-phenyl-9H-carbazole-3 A π-electron-rich heteroaromatic ring and a π-(9H-yl)-9H-carbazole skeleton are particularly preferred. The electron-deficient heteroaromatic ring directly bonded to the π-electron-rich heteroaromatic ring has electron-donating properties. The electron-accepting properties of the π-electron-deficient heteroaromatic rings are both strong, and the energies of the S1 and T1 levels are This is particularly preferred because the difference is small and thermally activated delayed fluorescence can be obtained efficiently. Instead of a π-electron-deficient heteroaromatic ring, an aromatic ring bonded with an electron-withdrawing group such as a cyano group is used. In addition, as the π-electron-rich skeleton, an aromatic amine skeleton, a phenazine skeleton, etc. may be used. In addition, as the π-electron deficient skeleton, a xanthene skeleton, a thioxanthene skeleton, Dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazole skeleton, ammonium The tetraquinone skeleton, boron-containing skeletons such as phenylborane and boranthrene, benzonitrile, The aromatic ring or heteroaromatic ring having a nitrile group or a cyano group, such as cyanobenzene, Carbonyl skeletons such as phenones, phosphine oxide skeletons, sulfone skeletons, etc. can be used. In this way, at least one of a π-electron deficient heteroaromatic ring and a π-electron rich heteroaromatic ring can be obtained. In place of one another, π-electron deficient and π-electron rich backbones can be used.

[0198] [ka]

[0199] TADF materials have a small difference between the S1 and T1 levels, and triple intersystem crossing occurs due to reverse intersystem crossing. The function of converting energy from first excitation energy to singlet excitation energy Therefore, the triplet excitation energy can be converted to a single state by a small amount of thermal energy. It is possible to upconvert to doublet excited energy (reverse intersystem crossing), and efficiently convert the singlet excited state It is possible to generate triplet excitation energy and convert it into luminescence. .

[0200] In addition, exciplexes (exciplexes) that form excited states with two types of substances The difference between the S1 and T1 levels is extremely small, As a TADF material capable of converting triplet excitation energy into singlet excitation energy, It has all the functions.

[0201] As an index of the T1 level, the phosphorescence spectrum observed at low temperatures (for example, from 77 K to 10 K) As for TADF materials, the fluorescent light spectrum has a short wavelength tail. Draw a tangent line to the S1 level, and the energy of the wavelength of the extrapolated line is the S1 level. When a tangent line is drawn at the long side of the tail and the energy of the wavelength of the extrapolated line is taken as the T1 level, The difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less. Even more preferable.

[0202] In addition, when a TADF material is used as a light-emitting material, the S1 level of the host material is It is preferable that the T1 level of the host material is higher than the T1 level of the TADF material. It is preferable that the temperature is higher than the above level.

[0203] The host material of the light-emitting layer may be a material having an electron transporting property or a material having a hole transporting property, Various carrier transport materials can be used, such as TADF materials.

[0204] Materials with hole transport properties include organic compounds with an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. Organic compounds are preferred. For example, 4,4'-bis[N-(1-naphthyl)-N-phenylalanine] N,N'-bis(3-methylphenyl)-N,N'-biphenyl (abbreviation: NPB), -Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4, 4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino] ]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9 -yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenyl mBPAFLP, 4-phenyl 4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation : PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazo PCBBi1BP), 4-(1-naphthyl-3-yl)triphenylamine )-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation : PCBAN), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carboxylate) PCBNBB, 9,9-dimethyl -N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]phenyl ]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl 9,9'-spirobi[(9H-fluoro-3-yl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[(9H-fluoro ... compounds with aromatic amine skeletons such as PCBASF, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene 3,6-bis(3,5-diphenylphenyl)bis(3,6-diphenylbenzoyl)biphenyl (abbreviation: CBP) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H -carbazole (abbreviated as PCCP), and ',4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene phenyl-9-yl)dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds with a thiophene skeleton, such as thiophene (abbreviated as DBTFLP-IV), and 4, 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: D BF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)fluorene phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan skeletons Among the above, compounds having an aromatic amine skeleton and Compounds having a rubazole skeleton have good reliability, high hole transport properties, and are easy to drive. It is also preferable because it contributes to reducing the voltage. Other organic compounds can also be used.

[0205] Examples of materials having electron transport properties include bis(10-hydroxybenzo[h]quinolinol). Nat)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato) )(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8- Quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolatozinc(II) (abbreviation: ZnBTZ) and π-electron-deficient heteroaromatic complexes An organic compound having an aromatic ring skeleton is preferred. An organic compound having a π-electron-deficient heteroaromatic ring skeleton is preferred. Examples of compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)- )-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4- Phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxa diazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1 ,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO 11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl- 1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene-4 -yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm Heterocyclic compounds with polyazole skeletons such as 2-[3-(dibenzothiophene)-II] and (4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDB q-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]di Benzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-( 9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxalate 4,6-bis[3-(phenanthrene-9-yl)phenyl]phenanthren-9-yl]phenanthren-9-yl ... phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-diphenyl)pyrimidine Diazolidinyl)phenyl)pyrimidine (abbreviation: 4,6mDBTP2Pm-II) Heterocyclic compounds with an amine skeleton and 2-[3'-(9,9-dimethyl-9H-fluorene -2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5- Triazine (abbreviation: mFBPTzn), 2-[(1,1'-biphenyl)-4-yl]- 4-phenyl-6-[9,9'-spirobi(9H-fluoren)-2-yl]-1,3, 5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[ 1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3, 5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho [1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3 ,5-triazine (abbreviation: mBnfBPTzn-02), etc. Heterocyclic compounds, 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridin 35DCzPPy, 1,3,5-tri[3-(3-pyridyl)phenyl]benzyl Examples include heterocyclic compounds having a pyridine skeleton, such as benzene (abbreviation: TmPyPB). Among the above, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a triazine skeleton are preferred. Compounds and heterocyclic compounds having a pyridine skeleton are preferred because of their high reliability. Heterocyclic compounds with an azine (pyrimidine or pyrazine) skeleton have high electron transport properties and are It also contributes to voltage reduction.

[0206] The TADF materials that can be used as host materials are listed above as TADF materials. When a TADF material is used as a host material, the TA The triplet excitation energy generated in the DF material is converted to singlet excitation energy by reverse intersystem crossing. The energy is then transferred to the light-emitting material, thereby increasing the luminous efficiency of the light-emitting device. In this case, the TADF material acts as an energy donor, and the light-emitting material acts as an energy acceptor.

[0207] This is very effective when the luminescent material is a fluorescent material. To obtain high luminous efficiency, the S1 level of the TADF material should be higher than the S1 level of the fluorescent material. It is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent material. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent material. Higher is preferable.

[0208] In addition, the fluorescent substance emits light at a wavelength that overlaps with the wavelength of the lowest energy absorption band of the fluorescent substance. It is preferable to use a TADF material that emits fluorescent light. This is preferable because it allows for smooth transfer of excitation energy to the substance, resulting in efficient light emission. stomach.

[0209] In addition, singlet excitation energy is efficiently generated from triplet excitation energy by reverse intersystem crossing. For this to occur, it is preferable that carrier recombination occurs in the TADF material. The triplet excitation energy generated in the DF material is transferred to the triplet excitation energy of the fluorescent material. For this purpose, it is preferable that the fluorescent substance has a luminophore ( It is preferable that the compound has a protecting group around the π bond (the skeleton that causes light emission). A substituent having no carbon atoms is preferred, and a saturated hydrocarbon is preferred, specifically a hydrocarbon having 3 to 10 carbon atoms. The alkyl groups listed below, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, A trialkylsilyl group having 3 to 10 protecting groups is preferred, and a group having a plurality of protecting groups is more preferred. Substituents without π bonds have poor carrier transport function, and therefore, The distance between the TADF material and the luminophores of the fluorescent material can be reduced without significantly affecting carrier recombination. Here, the luminophore is the molecule that causes light emission in a fluorescent substance. The luminophore preferably has a skeleton with a π bond and contains an aromatic ring. Preferably, the aromatic ring has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of the heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, and a phenanthren skeleton. Examples of the hydroxyazine skeleton include naphthalene skeleton and anthracene skeleton. skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton perylene skeleton, coumarin skeleton, quinacridone skeleton, naphthobisbenzofuran skeleton Fluorescent materials that emit light with high fluorescence quantum yields are preferred.

[0210] When a fluorescent substance is used as the light-emitting substance, the host material is a material having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used as a host material, it is possible to realize a light-emitting layer having good luminous efficiency and durability. The materials having an anthracene skeleton used as the material include a diphenylanthracene skeleton, In particular, a substance having a 9,10-diphenylanthracene skeleton is preferred because it is chemically stable. In addition, when the host material has a carbazole skeleton, the hole injection and transport properties are improved. However, a benzocarbazole skeleton in which a benzene ring is further condensed to a carbazole is preferred. When it contains carbazole, the HOMO becomes shallower by about 0.1 eV than that of carbazole, making it easier for holes to enter. In particular, when the host material contains a dibenzocarbazole skeleton, The HOMO is shallower than that of sol by about 0.1 eV, making it easier for holes to enter, and the hole transport Therefore, it is also preferable as a host material. Preferred are those having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or It is a substance that simultaneously has a benzocarbazole skeleton and a dibenzocarbazole skeleton. From the viewpoint of the hole injection and transport properties, a benzofluorene skeleton was used instead of a carbazole skeleton. A dibenzofluorene skeleton may also be used. Examples of such materials include 9-phenyl 3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( Abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H- Carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl) phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9 -anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBC zPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[ b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{ 4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene sen (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred because they show very good properties. It is a good choice.

[0211] The host material may be a mixture of a plurality of substances. When used, a material having an electron transporting property and a material having a hole transporting property may be mixed. It is preferable to mix a material having an electron transport property with a material having a hole transport property. Therefore, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The weight ratio of the content of the material having hole transport properties to the content of the material having electron transport properties is The ratio of the material having hole transport properties to the material having electron transport properties may be 1:19 to 19:1.

[0212] A phosphorescent material can be used as part of the mixed material. When a fluorescent substance is used as a luminescent substance, the luminescent substance transfers excitation energy to the fluorescent substance. It can be used as an energy donor.

[0213] Furthermore, these mixed materials may form an exciplex. The exciplex is formed to emit light that overlaps with the wavelength of the lowest energy absorption band of By selecting such a combination, energy transfer becomes smooth and light emission can be obtained efficiently. In addition, the use of this configuration is also preferable because the driving voltage is reduced.

[0214] At least one of the materials forming the exciplex may be a phosphorescent material. By doing so, triplet excitation energy is efficiently converted to singlet excitation energy by reverse intersystem crossing. can be converted to

[0215] As a combination of materials that efficiently form exciplexes, HO It is preferable that the MO level is equal to or higher than the HOMO level of the material having electron transport properties. When the LUMO level of the material having electron transport properties is higher than the LUMO level of the material having electron transport properties, It is preferable that the LUMO level and the HOMO level of the material are determined by cyclic voltammetry. From the electrochemical properties (reduction potential and oxidation potential) of the material measured by CV measurement It can be derived.

[0216] The formation of an exciplex is determined by, for example, the emission spectrum of a material having hole transport properties, the emission spectrum of a material having electron transport properties, The emission spectrum of the material having the above structure and the emission spectrum of the mixed film of these materials are shown in Fig. In comparison, the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each material ( This can be confirmed by observing the phenomenon of a new peak on the long wavelength side. Alternatively, transient photoluminescence (PL) of materials with hole transport properties and electron transport properties can be observed. The transient PL of the materials with the same properties and the transient PL of the mixed film of these materials were compared. The transient PL lifetime of the film has a longer-lived component than the transient PL lifetime of each material, or a delayed component. This can be confirmed by observing the difference in transient response, such as the percentage of In addition, the above-mentioned transient PL may be read as transient electroluminescence (EL). That is, the transient EL of a material with hole transport properties and the transient E of a material with electron transport properties are By comparing the transient EL of the L and the mixed films and observing the difference in the transient response, The formation of exciplexes can be confirmed.

[0217] The electron transport layer 114 is a layer containing a substance having an electron transport property. Examples of the electron-transporting material include those listed as the materials having electron-transporting properties that can be used as the host material. can be used.

[0218] The electron transport layer is made of a material having electron transport properties and a compound of an alkali metal or alkaline earth metal. It is preferable that the electron transport layer 114 contains a simple substance, a compound, or a complex. V / cm] is 600, the electron mobility is 1×10 -7 cm 2 / Vs or more 5×1 0 -5 cm 2 / Vs or less. By lowering the concentration, it is possible to control the amount of electrons injected into the light-emitting layer, and the light-emitting layer does not have an excess of electrons. This configuration can prevent the hole injection layer from becoming a composite material. The HOMO level of the material having hole transport properties in the composite material is -5.7 eV or more. The lifetime is good when the material has a relatively deep HOMO level of 5.4 eV or less. In this case, the material having electron transport properties is particularly preferred because its HOMO level is −6 The electron transporting material is preferably anthracene. It is preferable that the compound is an organic compound having both an anthracene skeleton and a heterocyclic skeleton. The heterocyclic skeleton is preferably an organic compound containing a nitrogen-containing five-membered ring skeleton. Alternatively, a nitrogen-containing 6-membered ring skeleton is preferred, and examples of these heterocyclic skeletons include a pyrazole ring, an imidazoline ring, and the like. azole ring, oxazole ring, thiazole ring, pyrazine ring, pyrimidine ring, pyridazine ring, etc. A nitrogen-containing five-membered ring skeleton or a nitrogen-containing six-membered ring skeleton containing two heteroatoms in the ring is particularly preferred. In addition, alkali metals or alkaline earth metals as simple substances, compounds or complexes are preferred. Preferably, the compound contains an 8-hydroxyquinolinato structure. Lithium 8-hydroxyquinolinate (abbreviated as Liq), 8-hydroxyquinolinate sodium (abbreviation: Naq) and the like. In particular, complexes of monovalent metal ions, especially li A complex of 8-hydroxyquinolinato structure is preferred, and Liq is more preferred. If the compound contains methyl-substituted methyl groups, its methyl-substituted group (e.g., 2-methyl-substituted or 5-methyl-substituted group) may be used. In addition, an alkali metal or alkaline earth metal may be used in the electron transport layer. The element, compound, or complex has a concentration difference (including 0) in the thickness direction. It is preferable that the

[0219] Between the electron transport layer 114 and the second electrode 102, a lithium fluoride layer was formed as an electron injection layer 115. Lithium fluoride (LiF), Cesium fluoride (CsF), Calcium fluoride (CaF2), 8-hydrogen Alkali metal or alkaline earth metals such as lithium quinolinate (abbreviation: Liq) The electron injection layer 115 may be a layer containing a metal or a compound thereof. The layer is made of a material containing an alkali metal or alkaline earth metal or a compound thereof. As the electride, for example, calcium carbonate may be used. Examples include a material in which electrons are highly added to a mixed oxide of silicon and aluminum.

[0220] Note that the electron-injecting layer 115 is formed using a substance having an electron-transporting property (preferably a substance having a bipyridine skeleton). The fluoride of the alkali metal or alkaline earth metal is in a microcrystalline state in the organic compound having the above-mentioned structure. It is also possible to use a layer containing a concentration of 50 wt% or more of the refractive index of the layer. Since the layer has a low external quantum efficiency, it is possible to provide a light-emitting device with a better external quantum efficiency. It becomes Noh.

[0221] In addition, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). When a potential is applied to the charge generating layer 116, holes are generated in the layer in contact with the cathode side of the layer, and electrons are generated in the layer in contact with the anode side. The charge generation layer 116 is a layer that can inject electrons into the layer adjacent to it. At least a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer 1 using the composite material mentioned above as a material that can be used. 17 is a film containing the above-mentioned acceptor material and a hole transport material as materials constituting a composite material. By applying a potential to the P-type layer 117, electrons Electrons are injected into the transport layer 114 and holes are injected into the second electrode 102, which is the cathode, forming a light-emitting device. In addition, since the organic compound according to one embodiment of the present invention has a low refractive index, By using this for the P-type layer 117, a light emitting device with good external quantum efficiency can be obtained. can.

[0222] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117. Preferably, one or both of layers 119 are provided.

[0223] The electron relay layer 118 contains at least a substance having electron transport properties, and the electron injection buffer layer 1 The electrons are transferred smoothly by preventing the interaction between the P-type layer 117 and the P-type layer 119. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor material in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron relay layer 11 is between the LUMO level of the material contained in the adjacent layer. Specific energy levels of the LUMO level in the electron transporting materials used in 8 is set to -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material. It is preferred to use materials or metal complexes having metal-oxygen bonds and aromatic ligands.

[0224] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate) Alkaline earth metal compounds (including carbonates such as titanium and cesium carbonate), alkaline earth metal compounds (oxides, halogens compounds of rare earth metals (including oxides, halides, carbonates) or compounds of rare earth metals (including oxides, halides, carbonates) It is possible to use a material with high electron injection properties, such as SiO 2 .

[0225] The electron injection buffer layer 119 is formed by containing a substance having an electron transporting property and a donor substance. When the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal, and their compounds (alkali metal compounds (oxides such as lithium oxide, halides , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, compounds of rare earth metals (including oxides, halides, carbonates) In addition to tetrathianaphthacene (abbreviated as TTN), nickelocene, decamethicone, An organic compound such as nickelocene can also be used. The electron transport layer 114 may be formed using the same material as that used for forming the electron transport layer 114 described above. This can be done.

[0226] The material forming the second electrode 102 is preferably one having a small work function (specifically, 3.8 eV or less). Bottom) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs). Lithium metals, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or 2 of the Periodic Table of Elements, and alloys containing these elements (MgAg, Rare earth metals such as AlLi), europium (Eu), ytterbium (Yb) and the like, However, when the second electrode 102 and the electron transport layer are connected to each other, By providing an electron injection layer, it is possible to use Al, Ag, ITO, silicon, etc., regardless of the magnitude of the work function. Various conductive materials such as indium oxide-tin oxide containing silicon oxide or silicon oxide are used as the second These conductive materials can be used as the electrode 102. It is possible to form the film using dry methods such as inkjet printing, spin coating, etc. It may also be formed by a wet method using a sol-gel method, or by using a paste of a metal material. Alternatively, the layer may be formed by a wet method.

[0227] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, etc. A printing method, an ink jet method, a spin coating method, or the like may also be used.

[0228] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0229] The structure of the layer provided between the first electrode 101 and the second electrode 102 is the same as that described above. However, it is not limited to the above. The first electrode 101 and the second electrode 102 are arranged so as to suppress quenching caused by the A preferred configuration is one in which a light-emitting region where holes and electrons recombine is provided at a location away from O2.

[0230] Furthermore, recombination in the hole transport layer or electron transport layer in contact with the light-emitting layer 113, particularly in the light-emitting layer 113 The carrier transport layer close to the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is determined by the luminescent material that constitutes the luminescent layer or the luminescent material contained in the luminescent layer. It is preferable that the material be made of a substance having a band gap larger than the band gap of the material. Desirable.

[0231] Next, we developed a light-emitting device (a stacked element, a tandem element) that has a structure in which multiple light-emitting units are stacked. The embodiment of the light-emitting device (also referred to as a "light-emitting device") will be described with reference to FIG. A light-emitting device has multiple light-emitting units between the electrode and the cathode. The EL layer 103 has a structure similar to that of the EL layer 103 shown in FIG. The light emitting device shown in FIG. 1(A) or The light-emitting device shown in FIG. 1(B) is a light-emitting device having one light-emitting unit. It can be said that.

[0232] In FIG. 1C, a first light-emitting unit 511 and a second light-emitting unit 512 are disposed between the anode 501 and the cathode 502. The second light-emitting unit 512 is stacked, and the first light-emitting unit 511 and the second light-emitting unit A charge generating layer 513 is provided between the anode 501 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in FIG. 1(A), respectively. The same as that described in the first light-emitting unit 51 can be applied. The first and second light-emitting units 512 may have the same or different configurations.

[0233] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 generates a light emitting The electron-injecting unit has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. In 1(C), when a voltage is applied so that the anode potential is higher than the cathode potential, In this case, the charge generating layer 513 injects electrons into the first light-emitting unit 511 and Any material capable of injecting holes into the gate 512 may be used.

[0234] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 1B. The composite material of an organic compound and a metal oxide has the properties of carrier injection, carrier transport, and the like. It has excellent electrical properties, making it possible to achieve low voltage and low current driving. When the anode side of the unit is in contact with the charge generating layer 513, the charge generating layer 513 is the light emitting unit. Since it can also function as a hole injection layer for the light-emitting unit, the light-emitting unit does not need to have a hole injection layer. Both are good.

[0235] In addition, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since the electron injection layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, the light-emitting layer The unit does not necessarily need to have an electron injection layer.

[0236] Although the light-emitting device having two light-emitting units has been described in FIG. 1C, the light-emitting device having three or more light-emitting units may be used. The same can be applied to a light-emitting device in which the above light-emitting units are stacked. As in the light-emitting device according to the present embodiment, a plurality of light-emitting units are electrically connected between a pair of electrodes. By separating the layers with the generation layer 513, high brightness light emission is possible while keeping the current density low. This allows for an even longer-life element. The device can be realized.

[0237] In addition, by making the light color of each light-emitting unit different, the light-emitting device as a whole can be For example, a light-emitting device having two light-emitting units can be used to obtain light of a desired color. In this device, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. By obtaining a color, it is possible to obtain a light-emitting device that emits white light as a whole. be.

[0238] In addition, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and Each layer such as the charge generating layer and the electrodes can be formed by, for example, a vapor deposition method (including a vacuum deposition method), a droplet discharge method (including an ink jet method), or the like. It can be formed by using methods such as ink jet printing, coating, and gravure printing. They can be used in a variety of applications, including low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and or polymeric material.

[0239] (Embodiment 3) In this embodiment, a light-emitting device using the light-emitting device described in Embodiment 2 will be described. do.

[0240] In this embodiment, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 will be described. 2A is a top view of a light-emitting device, and FIG. This light emitting device is a cross-sectional view taken along the lines AB and CD in FIG. A drive circuit (source line drive circuit) 601 shown by the dotted line controls the light emission of the source. It includes a pixel portion 602 and a driving circuit portion (gate line driving circuit) 603. The sealing substrate 605 is a sealing material, and the inside surrounded by the sealing material 605 is a space 607. are.

[0241] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting signals, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the input circuit 609 Although only the FPC is shown here, this FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0242] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601 and a pixel portion are formed. , one pixel in the pixel section 602 is shown.

[0243] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of a material such as fluoride, polyester, or acrylic resin. It is enough to manufacture it.

[0244] The structure of the transistors used in the pixels and driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium or the like can be used. Alternatively, in-type metal oxides such as In-Ga-Zn-based metal oxides can be used. An oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0245] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a partially crystalline region) When a semiconductor having crystallinity is used, the transistor This is preferable because it can suppress deterioration of the star characteristics.

[0246] Here, in addition to the transistors provided in the pixels and the driver circuits, It is preferable to use an oxide semiconductor for a semiconductor device such as a transistor. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the off-state of the transistor can be This can reduce the current in the

[0247] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is preferable that the oxide semiconductor contains an oxide represented by the formula (metal such as La, Ce or Hf). More preferable.

[0248] In particular, the semiconductor layer has a plurality of crystal portions, and the c-axes of the crystal portions are aligned with the surface on which the semiconductor layer is formed, Alternatively, the oxide is oriented perpendicular to the upper surface of the semiconductor layer and has no grain boundary between adjacent crystal portions. It is preferable to use a nitride semiconductor film.

[0249] By using such materials for the semiconductor layer, fluctuations in electrical characteristics are suppressed, resulting in high reliability. This makes it possible to realize a low-power transistor.

[0250] Furthermore, the transistor having the above-described semiconductor layer can be used as a transistor due to its low off-state current. It is possible to retain the charge stored in the capacitor for a long period of time through such a transistor. By applying a transistor to each pixel, the gradation of the image displayed in each display area can be maintained while driving It is also possible to shut down the circuit. As a result, electronic devices with extremely low power consumption can be realized. It can be realized.

[0251] For stabilizing the characteristics of the transistor, it is preferable to provide an underlayer film. Inorganic films such as silicon oxide film, silicon nitride film, silicon oxynitride film, and silicon nitride oxide film The insulating film can be formed as a single layer or a laminated layer. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD ( Formed using Atomic Layer Deposition (ALD), coating, printing, etc. It should be noted that the undercoat film need not be provided if it is not necessary.

[0252] The FET 623 indicates one of the transistors formed in the driver circuit 601. The driving circuit can be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment, a driver integrated type in which a driver circuit is formed on a substrate is shown. However, this is not necessarily required, and the drive circuit can be formed externally rather than on the substrate.

[0253] The pixel section 602 includes a switching FET 611, a current control FET 612 and its driver. The pixel is formed by a plurality of pixels including a first electrode 613 electrically connected to the drain. However, the present invention is not limited to this, and a pixel unit that combines three or more FETs and a capacitance element may also be used. good.

[0254] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive acrylic resin film of a mold.

[0255] In order to improve the coverage of the EL layer and the like to be formed later, the insulating material 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic resin is used, the radius of curvature ( It is preferable that the insulating material 614 has a curved surface having a thickness of 0.2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0256] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function of It is desirable to use a large material, for example, an ITO film or an indium-silicon-containing film. Indium tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, In addition to single layer films such as ROM film, tungsten film, Zn film, and Pt film, titanium nitride film and aluminum film are also available. a titanium nitride film and an aluminum-based film; A three-layer structure with a silicon film can be used. The resistance is low, good ohmic contact can be achieved, and the electrode can also function as an anode. .

[0257] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 is formed by various methods such as the above. Other materials that make up the EL layer 616 include low molecular weight compounds, may be a polymer compound (including an oligomer or a dendrimer).

[0258] Furthermore, a material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode As the material, materials with a small work function (Al, Mg, Li, Ca, or their alloys or compounds) It is preferable to use a material such as MgAg, MgIn, or AlLi. When the light generated in 6 is transmitted through the second electrode 617, the second electrode 617 is Thin metal films and transparent conductive films (ITO, indium tin oxide containing 2-20 wt% zinc oxide) It uses lamination of indium tin oxide containing indium and silicon, zinc oxide (ZnO, etc.) It's good to do that.

[0259] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting device. The light-emitting device is the light-emitting device described in embodiment 2. The element part is formed with a plurality of light emitting devices. The light-emitting device according to the second embodiment and the light-emitting device having other configurations are It's okay if there is a mixture of these.

[0260] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealing material 605. A light-emitting device is placed in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. The space 607 is filled with a filler material. In some cases, the gas is filled with an inert gas (nitrogen, argon, etc.), and in other cases, it is filled with a sealing material. By forming a recess in the sealing substrate and providing a desiccant there, deterioration due to the influence of moisture can be prevented. This is a preferable configuration because it can suppress the degradation.

[0261] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyester, acrylic resin, or the like can be used.

[0262] Although not shown in Figure 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. The exposed portion of the sealant 605 may be covered with a protective film. A protective film may be formed on the surfaces and sides of the pair of substrates, the sealing layer, the insulating layer, and the like. A rim layer, etc. may be provided over the exposed side surface.

[0263] The protective film can be made of a material that is difficult for impurities such as water to permeate. It is possible to effectively prevent impurities such as these from diffusing from the outside to the inside.

[0264] The materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers and the like can be used, for example, aluminum oxide, hafnium oxide, hafnium Lanthanum 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 or indium oxide Materials containing hafnium, aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and sulfides containing erbium and strontium, oxides containing erbium and aluminum, yttrium Materials containing oxides containing lithium and zirconium can be used.

[0265] The protective film can be formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). The ALD method can be used to form protective materials. It is preferable to use it for films. By using the ALD method, it is possible to eliminate cracks, pinholes, etc. It is possible to form a protective film with reduced defects or with a uniform thickness. Damage to the processed member when forming the protective film can be reduced.

[0266] For example, by forming a protective film using the ALD method, it is possible to fabricate a surface with complex irregularities or a surface with a touch panel. A uniform protective film with few defects can be formed on the top, sides and back of the panel. .

[0267] In this manner, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 is obtained. It is possible.

[0268] The light emitting device in this embodiment uses the light emitting device described in Embodiment 2. In this way, a light emitting device having excellent characteristics can be obtained. Since the light-emitting device has good light-emitting efficiency, it is possible to make it a light-emitting device with low power consumption. do.

[0269] In FIG. 3, a light-emitting device that emits white light is formed, and a colored layer (color filter) is provided. FIG. 3(A) shows an example of a full-color light-emitting device. an insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, The first interlayer insulating film 1020, the second interlayer insulating film 1021, the peripheral portion 1042, and the pixel portion 1040 , the driving circuit unit 1041, the first electrodes 1024W, 1024R, and 1024G of the light-emitting device , 1024B, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting device, and an encapsulant. A stop substrate 1031, a seal material 1032, etc. are shown in the figure.

[0270] In addition, in FIG. 3(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on a transparent substrate 1033. A transparent substrate 1 on which a colored layer and a black matrix are provided may be further provided. The colored layer and the black matrix are aligned and fixed to the substrate 1001. The dust 1035 is covered with an overcoat layer 1036. The light-emitting layer is where light does not pass through the colored layers and goes out, and the light passes through the colored layers of each color and goes out. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, green, or blue. This allows images to be expressed using four color pixels.

[0271] In FIG. 3(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer An example in which a layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020 As shown in the figure, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. is also good.

[0272] In the light emitting device described above, light is taken in toward the substrate 1001 on which the FET is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a top emission structure. A cross-sectional view of the light-emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light is used as the substrate 1001. Until the connection electrode that connects the FET and the anode of the light-emitting device is fabricated, After that, a third interlayer insulating film 1037 is formed on the substrate 1031 in the same manner as in the case of the multi-emission light emitting device. The insulating film is formed to cover the electrode 1022. This insulating film may also serve as a planarizing layer. The interlayer insulating film 1037 may be formed using the same material as the second interlayer insulating film, or other known materials. It is possible.

[0273] The first electrodes 1024W, 1024R, 1024G, 1024B of the light emitting device are The anode is used as the anode, but it can also be the cathode. In the case of an optical device, the first electrode is preferably a reflective electrode. The EL layer 103 has the same structure as that described in the second embodiment and emits white light. The device structure is such that light can be obtained.

[0274] In the top emission structure shown in Figure 4, the colored layers (red colored layer 1034R, green colored layer The sealing is performed by a sealing substrate 1031 provided with a blue color layer 1034G and a blue color layer 1034B. The sealing substrate 1031 has a black matrix disposed between the pixels. A coloring layer (red coloring layer 1034R, green coloring layer 1034G, The blue colored layer 1034B) and the black matrix are covered by the overcoat layer 1036. The sealing substrate 1031 may be covered. Note that a light-transmitting substrate is used. Although an example of full-color display using four colors, red, green, blue, and white, is shown here, there is no particular limitation. Alternatively, full color display may be performed using four colors of red, yellow, green, and blue, or three colors of red, green, and blue.

[0275] In a top-emission type light-emitting device, the microcavity structure can be suitably applied. The light-emitting device having a microcavity structure has a first electrode as a reflective electrode and a second electrode as a This is achieved by using a semi-transparent and semi-reflective electrode. The device has at least an EL layer, and at least a light-emitting layer that serves as a light-emitting region.

[0276] The reflectance of the reflective electrode for visible light is 40% to 100%, preferably 70% to 100%. %, and its resistivity is 1×10 -2 The film is assumed to be less than Ωcm. The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1×10 -2 It is assumed that the film has a resistance of Ωcm or less.

[0277] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transparent and semi-reflective electrode. The sound is reflected and resonates.

[0278] The light-emitting device is made by changing the thickness of the transparent conductive film, the composite material, the carrier transport material, etc. By doing so, the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed. This strengthens the light of the resonating wavelength between the reflective electrode and the semi-transparent and semi-reflective electrode, and It can attenuate light of wavelengths that are not

[0279] The light reflected by the reflective electrode and returned (first reflected light) is semi-transmitted from the light emitting layer. The light that directly enters the semi-reflective electrode (first incident light) interferes greatly with the reflective electrode. The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the amplified It is preferable to adjust the optical distance to a wavelength of the first light. By matching the phase of the reflected light with the phase of the first incident light, the light emitted from the light-emitting layer can be further amplified. do.

[0280] In the above configuration, even if the EL layer has a structure having a plurality of light-emitting layers, it may be a single light-emitting layer. For example, it may be combined with the configuration of the tandem light emitting device described above. In addition, a plurality of EL layers are provided in one light-emitting device with a charge generating layer sandwiched therebetween, and each EL layer The present invention may be applied to a configuration in which a single or multiple light-emitting layers are formed on the substrate.

[0281] The microcavity structure makes it possible to enhance the front-direction emission intensity of specific wavelengths. This allows for lower power consumption. In the case of a light-emitting device that displays images using a single pixel, the yellow light emission not only improves brightness, but also Since a microcavity structure tailored to the wavelength of each color can be applied, it is possible to achieve light-emitting devices with excellent characteristics. It can be placed.

[0282] The light emitting device in this embodiment uses the light emitting device described in Embodiment 2. In this way, a light emitting device having excellent characteristics can be obtained. Since the light-emitting device has good light-emitting efficiency, it is possible to make it a light-emitting device with low power consumption. do.

[0283] Up to this point, we have explained about active matrix light emitting devices, but from now on we will be talking about passive light emitting devices. A passive matrix light-emitting device will be described. 5A is a perspective view showing the light emitting device, and FIG. 5B) is a cross-sectional view of FIG. 5A cut along XY. In FIG. 5, on a substrate 951, An EL layer 955 is provided between the electrode 952 and the electrode 956. The ends of the electrode 952 are It is covered with an insulating layer 953. A partition wall layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 become thicker between one sidewall and the other sidewall as they approach the substrate surface. That is, the cross section of the partition wall layer 954 in the short side direction has a slope such that the gap between the partition walls becomes narrower. The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) ) is the upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). In this way, by providing the partition layer 954, it is possible to prevent the light emitting device from being damaged by static electricity or the like. In addition, the present invention can also be applied to passive matrix light emitting devices. A light-emitting device having high reliability or low power consumption, which uses the light-emitting device according to the second aspect. A small light emitting device can be produced.

[0284] The light emitting device described above is composed of a large number of minute light emitting devices arranged in a matrix. Since it is possible to control each of these, it can be suitably used as a display device for displaying images. It is a light-emitting device.

[0285] This embodiment mode can be freely combined with other embodiment modes.

[0286] (Fourth embodiment) In this embodiment, an example in which the light-emitting device described in Embodiment 2 is used as a lighting device is shown in FIG. 6(B) is a top view of the lighting device, and FIG. 6(A) is a diagram showing the lighting device in FIG. 6(B). FIG. 5 is a cross-sectional view of the ef section.

[0287] The lighting device of this embodiment is a light-transmitting substrate 400 serving as a support, on which a first The first electrode 401 is formed on the substrate 10. When light is extracted from the first electrode 401 side, the first electrode 401 is made of a transparent material. The material is formed from a material having the following properties.

[0288] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0289] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is the same as that in Embodiment 1. The configuration of the EL layer 103 in the light-emitting device 100, or the combination of the light-emitting units 511, 512 and the charge-generating layer 513 For details about these configurations, please refer to the relevant descriptions.

[0290] The second electrode 404 is formed to cover the EL layer 403. When light is extracted from the first electrode 401 side, the second electrode 102 corresponds to the second electrode 102. The first electrode 404 is formed of a highly reflective material. The voltage is supplied by connecting

[0291] As described above, a light-emitting device having the first electrode 401, the EL layer 403, and the second electrode 404 is provided. The lighting device described in this embodiment has a high luminous efficiency. Therefore, the lighting device in this embodiment is a lighting device with low power consumption. can be done.

[0292] The substrate 400 on which the light emitting device having the above structure is formed is sealed with a sealing substrate 407. The lighting device is completed by fixing and sealing using sealing materials 405 and 406. Either 405 or 406 may be used. In addition, the inner sealing material 406 (FIG. 6(B) ) (not shown) can also be mixed with a desiccant, which can absorb moisture. This leads to improved reliability.

[0293] In addition, a part of the pad 412 and the first electrode 401 is extended outside the sealing materials 405 and 406. By providing this, it can be used as an external input terminal. An IC chip 420 equipped with the above may be provided.

[0294] As described above, the lighting device according to this embodiment uses the light-emitting device according to the second embodiment as the EL device. The light emitting device uses a light emitting diode, and thus consumes less power.

[0295] (Embodiment 5) In this embodiment, an example of an electronic device including the light-emitting device described in embodiment 2 as a part thereof is as follows. 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 has low power consumption. It is possible to make an electronic device with a small light emitting part.

[0296] Examples of electronic devices to which the light-emitting device is applied include television sets (televisions, (also called television receivers), computer monitors, digital cameras, digital digital video cameras, digital photo frames, mobile phones (also known as mobile phones or mobile phone devices) (hereinafter referred to as "games"), portable game machines, personal digital assistants, sound reproduction devices, large game machines such as pachinko machines Specific examples of these electronic devices are listed below.

[0297] 7A shows an example of a television device. The television device includes a housing 710 A display unit 7103 is built into the housing 1. In this case, a stand 7105 is used to hold the housing The display unit 7103 can display images. The display portion 7103 has the light-emitting devices described in Embodiment 2 arranged in matrix. It is composed of the following.

[0298] The television device can be operated using the operation switches on the housing 7101 or a separate remote control. This can be done by the remote control device 7110. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the

[0299] The television device is assumed to be equipped with a receiver, modem, etc. It can receive television broadcasts and can also communicate by wire or wireless via a modem. By connecting to a network, you can send and receive data in one direction (sender to receiver) or two directions (sender to receiver). It is also possible to communicate information between the recipient and the receiver, or between receivers themselves.

[0300] FIG. 7(B1) shows a computer, which includes a main body 7201, a housing 7202, a display portion 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. This computer is configured to display the light-emitting devices according to the second embodiment in a matrix. The display portion 7203 is fabricated by using the LCD panel 7201 as a display portion. The computer shown in FIG. 7(B2) may have a keyboard 7 204, a second display unit 7210 is provided instead of the pointing device 7206. The second display portion 7210 is a touch panel type. Input can be made by operating the input display with a finger or a special pen. The second display unit 7210 can display not only input images but also other images. The display unit 7203 may also be a touch panel. The screen may be scratched or broken when stored or transported due to the connection. It is also possible to prevent problems from occurring.

[0301] FIG. 7C shows an example of a mobile terminal. The mobile phone is built in a housing 7401. In addition to the display unit 7402, operation buttons 7403, an external connection port 7404, a speaker 740 5, a microphone 7406, etc. The mobile phone is equipped with the light-emitting device described in the second embodiment. The display portion 7402 is made by arranging devices in a matrix.

[0302] The mobile terminal shown in FIG. 7C allows users to input information by touching the display portion 7402 with a finger or the like. In this case, it is possible to make a call or create an email. Operations such as turning on / off the camera can be performed by touching the display portion 7402 with a finger or the like.

[0303] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0304] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. Desirable.

[0305] In addition, the mobile terminal may include a sensor for detecting tilt, such as a gyro or acceleration sensor. By providing a device, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be displayed. The display can be switched automatically.

[0306] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, if the image signal to be displayed on the display unit is a video signal, If it is data, the display mode is switched to, and if it is text data, the input mode is switched to.

[0307] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0308] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0309] Note that the structure described in this embodiment mode may be obtained by appropriately combining the structures described in any of Embodiment Modes 1 to 4. They can be used in combination.

[0310] As described above, the light emitting device according to the second embodiment has a very wide range of application. This light emitting device can be applied to electronic devices in a wide range of fields. By using the light-emitting device described above, electronic devices with low power consumption can be obtained.

[0311] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0312] The cleaning robot 5100 has a display 5101 on the top surface and multiple The camera 5102, the brush 5103, and the operation button 5104 are also shown. However, the underside of the cleaning robot 5100 is provided with tires, a suction port, etc. The robot 5100 also has an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, It is equipped with various sensors such as a sensor, a light sensor, and a gyro sensor. 100 is equipped with wireless communication means.

[0313] The cleaning robot 5100 moves by itself, detects the dust 5120, and sucks it out from the suction port on the bottom. It can suck up dirt.

[0314] In addition, the cleaning robot 5100 analyzes the image captured by the camera 5102 and detects the wall, furniture, or It can detect obstacles such as steps. Image analysis can also detect obstacles such as wiring. If an object that may get tangled in the brush 5103 is detected, the rotation of the brush 5103 can be stopped. can.

[0315] The display 5101 can display the remaining battery level and the amount of dust sucked. The route traveled by the cleaning robot 5100 can be displayed on the display 5101. In addition, the display 5101 is a touch panel, and the operation button 5104 is It may be provided in the ray 5101.

[0316] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the Cleaning Robot 5100 can check the status of the room even when he is away from home. In addition, the display on the display 5101 can be displayed on a mobile electronic device such as a smartphone. You can also check it out at.

[0317] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0318] The robot 2100 shown in FIG. 8(B) includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, upper camera 2103, speaker 2104, display 2105, It is equipped with an internal camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0319] The microphone 2102 has a function of detecting the user's voice and environmental sounds. The speaker 2104 has a function of emitting sound. The device 2102 and the speaker 2104 can be used to communicate with the user. It is possible.

[0320] The display 2105 has the function of displaying various information. Any information desired by the user can be displayed on the display 2105. The display 2105 may be equipped with a touch panel. It may be an information terminal that can be charged by placing it in a fixed position on the robot 2100. and enables data transfer.

[0321] The upper camera 2103 and the lower camera 2106 are used to capture images of the surroundings of the robot 2100. The obstacle sensor 2107 detects the obstacles in the robot 210 by using the moving mechanism 2108. When moving forward, the robot can sense whether there are any obstacles in its path. 00 uses an upper camera 2103, a lower camera 2106, and an obstacle sensor 2107. The light-emitting device according to one embodiment of the present invention can recognize the surrounding environment and move safely. It can be used for the display 2105.

[0322] FIG. 8(C) is a diagram showing an example of a goggle-type display. For example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, Connection terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, power, radiation (including those that measure radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), The device includes a microphone 5008, a display unit 5002, a support unit 5012, earphones 5013, and the like.

[0323] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002. .

[0324] FIG. 9 shows an example in which the light-emitting device according to the second embodiment is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002. As the light source 2, the lighting device described in the third embodiment may be used.

[0325] FIG. 10 shows an example in which the light-emitting device according to the second embodiment is used as an indoor lighting device 3001. The light-emitting device described in the second embodiment is a light-emitting device with high luminous efficiency. In this way, a lighting device with low power consumption can be obtained. The chair can be made large, so it can be used as a large-area lighting device. The light-emitting device described in the second embodiment is thin and can be used as a thin lighting device. This makes it possible to

[0326] The light-emitting device described in the second embodiment can also be mounted on the windshield or dashboard of an automobile. FIG. 11 shows the light emitting device according to the second embodiment mounted on the front windshield of an automobile. The display area 5200 to the display area 5203 are used for a class or a dashboard. 10 shows a display provided using the light-emitting device described in Embodiment 2.

[0327] In this embodiment, the display area 5200 and the display area 5201 are provided on the windshield of a car. 1 is a display device incorporating the light-emitting device according to embodiment 2. By making the first electrode and the second electrode from light-transmitting electrodes, the opposite side is transparent. It is possible to provide a so-called see-through display device in which the image is seen through the screen. If it is displayed on the windshield of a car, it will not obstruct the view. In addition, when a transistor for driving is provided, an organic semiconductor Translucent organic transistors using conductive materials and transistors using oxide semiconductors are being developed. It is preferable to use a transistor having such a configuration.

[0328] The display region 5202 is provided with the light-emitting device described in Embodiment 2. The display area 5202 displays an image captured by an imaging means provided on the vehicle body. By doing so, it is possible to compensate for the visibility obstructed by the pillars. The display area 5203 provided on the board allows the view blocked by the car body to be displayed on the By projecting images from an external imaging device, blind spots are compensated for and safety is improved. By projecting images that complement the invisible parts, it becomes more natural. Safety checks can be performed without any discomfort.

[0329] The display area 5203 also displays navigation information, speed, RPM, and air conditioning settings. By doing so, various information can be provided. The display can be adjusted as needed to suit the user's preferences. The display items and layout of the information can be changed. The display areas 5200 to 5203 can also be provided. 203 can also be used as a lighting device.

[0330] 12(A) and (B) show a foldable mobile information terminal 5150. The foldable mobile information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 515 12(A) shows the mobile information terminal 5150 in an unfolded state. Figure 5B) shows the mobile information terminal in a folded state. The mobile information terminal 5150 has a large display area. Despite having a range of 5152, it is compact and highly portable when folded.

[0331] The display area 5152 can be folded in half by the bend 5153. 3 is composed of an expandable member and multiple support members, and when folding, The bending portion 5153 has a curvature radius of 2 mm or more, preferably 3 mm or more. It can be folded.

[0332] The display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used in the display region 5152. Cut.

[0333] 13(A) to 13(C) show a foldable mobile information terminal 9310. 13(A) shows the mobile information terminal 9310 in an unfolded state. The mobile information terminal 9310 is shown in a state in which it is changing from one folded state to the other. FIG. 13C shows the portable information terminal 9310 in a folded state. The foldable design offers excellent portability and a seamless, large viewing area when unfolded. This provides excellent visibility of the display.

[0334] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The two housings 9315 are bent to open the mobile information terminal 9310. The light-emitting device of one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for the display panel 9311. [Example]

[0335] <Synthesis Example 1> In this example, N -(3,3'',5',5''-tetra-tert-butyl-1,1':3',1''- Terphenyl-5-yl)-N-phenyl-9,9-dimethyl-9H-fluorene-2- The synthesis method of mmtBu amine (abbreviation: mmtBumTPFA-02) is described below. The structure of mTPFA-02 is shown below.

[0336] [ka]

[0337] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > 37.2 g (128 ml) of 1,3-dibromo-5-tert-butylbenzene was added to a three-neck flask. mol), 3,5-di-tert-butylphenylboronic acid 20.0 g (85 mmol) , potassium carbonate 35.0 g (255 mmol), toluene 570 mL, ethanol 170 After degassing under reduced pressure, the flask was replaced with nitrogen. Palladium acetate 382 mg (1.7 mmol), triphenylphosphine 901 mg (3 The mixture was heated at 40°C for about 5 hours. After that, the mixture was cooled to room temperature and the organic layer and aqueous layer were The layers were separated, and magnesium sulfate was added to the organic layer to remove water, followed by concentration. The solution was purified by silica gel column chromatography to obtain the desired colorless oily product, 21. The synthesis scheme for Step 1 is shown below.

[0338] [ka]

[0339] Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The 3-bromo-3',5,5'-tri-tert-butyl ether obtained in Step 1 was placed in a three-neck flask. Thilbiphenyl 15.0 g (38 mmol), 4,4,4',4',5,5,5',5- Octamethyl-2,2'-bi-1,3,2-dioxaborolane 10.5g (41mmol ), potassium acetate 11.0 g (113 mmol), N,N-dimethylformamide 125 After degassing under reduced pressure, the flask was purged with nitrogen and [1,1'-bis( Diphenylphosphino)ferrocene]dichloropalladium(II) 1.5g (1.9mm The mixture was heated at 100°C for about 3 hours, and then cooled to room temperature to separate the organic layer and the aqueous layer. The extract was added with magnesium sulfate and then extracted with water. The toluene solution of the resulting mixture was subjected to silica gel column chromatography. The solution obtained by purifying with ethanol was concentrated to obtain a concentrated toluene solution. The mixture was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at about 20°C. The obtained solid was dried under reduced pressure at about 80°C to obtain 13.6 g of the target white solid in a yield of 81%. The synthesis scheme for Step 2 is shown below.

[0340] [ka]

[0341] Step 3: 3-Bromo-3'',5,5',5''-tetra-tert-butyl- Synthesis of 1':3',1''-terphenyl A three-neck flask was charged with 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 5.0 g (11.1 mmol), 1,3-dibromo-5-tert-butylbenzene 4.8 g ( 16.7 mmol), potassium carbonate 4.6 g (33.3 mmol), toluene 56 mL, Add 22 mL of ethanol and 17 mL of tap water, degas the flask under reduced pressure, and then Nitrogen substitution was performed, and palladium acetate 50 mg (0.22 mmol), triphenylphosphine 1 16 mg (0.44 mmol) of HCl was added and heated at 80°C for about 10 hours. The organic layer and the aqueous layer were separated. Magnesium sulfate was added to this solution to remove water and concentrate it. The hexane solution obtained was purified by silica gel column chromatography to obtain the target compound. The target product was obtained as a white solid (3.0 g, yield 51.0%). '',5,5',5''-tetra-tert-butyl-1,1':3',1''-terf The synthesis scheme of phenyl is shown below.

[0342] [ka]

[0343] <Step 4: Synthesis of mmtBumTPFA-02> A three-neck flask was charged with 3-bromo-3'',5,5',5''-tetra-tert-butyl-1 ,1':3',1''-terphenyl 3.0g (5.6mmol), 2-anilino-9, 9-Dimethylfluorene 1.6g (5.6mmol), sodium tert-butoxide 1.6g (16.8mmol) and 28mL of toluene were added, and after degassing under reduced pressure, The flask was purged with nitrogen and 64 mg of bis(dibenzylideneacetone)palladium(0) 0.11mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 138 mg (0.34 mmol) of ethanol was added, and the mixture was heated at 120°C for about 8 hours. After that, the temperature of the flask was returned to about 60°C, about 1 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting toluene solution was purified by silica gel column chromatography. The resulting solution was concentrated to give 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 residue was filtered, and the ethanol was removed from the resulting solid at about 80°C under reduced pressure to give the target white solid. The compound was obtained in 3.2 g with a yield of 78%. The synthesis scheme is shown below.

[0344] [ka]

[0345] The white solid obtained in step 4 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown in Figures 14(A) and 14(B). The graph shows an enlarged range from ppm to 8.0 ppm. Therefore, in this synthesis example, N-(3,3'',5',5''-tetra-t ert-butyl-1,1':3',1''-terphenyl-5-yl)-N-phenyl- It was found that 9,9-dimethyl-9H-fluoren-2-amine was synthesized.

[0346] 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(d d,1H,J=1.7Hz),7.45(dd,1H,J=1.7Hz),7.43(d d,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,1H,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).

[0347] Next, 3.2 g of the obtained white solid was subjected to a train sublimation method under a pressure of 2.9 Pa. The sublimation purification was carried out under the conditions of an argon flow rate of 10.0 mL / min and a temperature of 235°C. 2.7 g of a slightly yellowish white solid was obtained with a recovery rate of 84%.

[0348] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPFA-02 (hereinafter simply referred to as The absorption spectrum and emission spectrum were measured. was measured using a UV-visible spectrophotometer (JASCO Corporation, FP-8600 model) in a toluene solution. The sample was placed in a quartz cell and measured at room temperature. (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used, and the toluene solution was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 15. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. The thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorbance shown in Figure 15 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured by placing only toluene in a quartz cell was subtracted from the above. are.

[0349] As shown in Figure 15, mmtBumTPFA-02 has an emission peak at 395 nm. Ta.

[0350] Next, the mmtBumTPFA-02 obtained in this example was analyzed by liquid chromatography mass spectrometry ( Liquid Chromatography Mass Spectrometry, The analysis was carried out by LC / MS analysis.

[0351] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0352] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPFA-02 at a desired concentration in an organic solvent. The injection volume was 5.0 μL.

[0353] By PRM, the ion m / z=738.50 derived from mmtBumTPFA-02 was detected. MS 2 The PRM settings were as follows: the mass range of the target ion was m / z = 73 8.50±2.0 (isolation window=4), and detection was performed using positive The energy NCE (No) that accelerates the target ions in the collision cell was The measured value was 60. The MS spectrum is shown in FIG.

[0354] In addition, the refractive index of mmtBumTPFA-02 was measured using a spectroscopic ellipsometer (J. The results are shown below, measured using a Woollam Japan M-2000U. The materials for each layer were deposited on a quartz substrate by vacuum deposition to a thickness of approximately 50 nm. The figure shows the refractive index of ordinary light, n, Ordinary, and the refractive index of extraordinary light, n, It was described as "extra-ordinary."

[0355] From this figure, mmtBumTPFA-02 emits light in the blue light region (wavelengths of 455 nm to 465 nm). The refractive index of ordinary light in the entire range of light is 1.68, and is in the range of 1.50 to 1.75. The refractive index of ordinary light at a wavelength of 633 nm is 1.63, and the range is 1.45 to 1.70. It was found that the refractive index of the material was low, falling within the range below.

[0356] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPFA-02 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan, PYRIS1D) The powder was placed on an aluminum cell and measured using a fluorine-containing fluoride (SC). The Tg of 02 was 109°C. [Example]

[0357] <Synthesis Example 2> In this example, N -(1,1'-biphenyl-4-yl)-N-(3,3'',5',5''-tetra-t ert-butyl-1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl Synthesis of benzoyl-9H-fluoren-2-amine (abbreviation: mmtBumTPFBi-02) The structure of mmtBumTPFBi-02 is shown below.

[0358] [ka]

[0359] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0360] Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 1.

[0361] Step 3: 3-Bromo-3'',5,5',5''-tetra-tert-butyl- Synthesis of 1':3',1''-terphenyl The synthesis was carried out in the same manner as in Step 3 of Synthesis Example 1.

[0362] <Step 4: Synthesis of mmtBumTPFBi-02> The 3-bromo-3'',5,5',5''-tetra- tert-Butyl-1,1':3',1''-terphenyl 3.0g (5.6mmol) , 2-(4-biphenylyl)amino-9,9-dimethylfluorene 2.0 g (5.6 mm ol), sodium tert-butoxide 1.6 g (16.8 mmol), toluene 28 After degassing under reduced pressure, the flask was replaced with nitrogen and bis(dibenzylidene (acetone)palladium(0) 64 mg (0.11 mmol), 2-dicyclohexyl Add 138 mg (0.34 mmol) of sphino-2',6'-dimethoxybiphenyl. The flask was heated at 120°C for about 8 hours. After that, the temperature of the flask was returned to about 60°C, and about 1 ml of water was added. The precipitated solid was filtered off and washed with toluene. The filtrate was concentrated, and the obtained toluene was The solution was purified by silica gel column chromatography. Ethanol was added to this toluene solution, and the mixture was concentrated under reduced pressure to obtain a toluene solution. A suspension was obtained, and the precipitate was filtered at about 20°C, and the obtained solid was dried under reduced pressure at about 80°C. The target product, a white solid, was obtained in 3.5 g with a yield of 77%. The synthesis scheme for Step 4 is shown below. Shown below.

[0363] [ka]

[0364] The white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by H-NMR are shown in Figure 18 (A) and (B). Note that Figure 18(B) shows the range from 7.0 ppm to 8.0 ppm in Figure 18(A). The graph shows the enlarged range of 0 ppm. The numerical data is also shown below. From N-(1,1'-biphenyl-4-yl)-N-(3,3'',5',5''-tetramethyl- tra-tert-butyl-1,1':3',1''-terphenyl-5-yl)-9,9 It was found that 9H-dimethyl-9H-fluoren-2-amine was successfully synthesized.

[0365] 1 H-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).

[0366] Next, 3.5 g of the obtained white solid was subjected to a train sublimation method under a pressure of 2.6 Pa. The sublimation purification was carried out under the conditions of an argon flow rate of 10.0 mL / min and a temperature of 255°C. 2.9 g of a white solid was obtained with a recovery rate of 83%.

[0367] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPFBi-02 (hereinafter, The absorption spectrum (simply referred to as "absorption spectrum") and emission spectrum were measured. A UV-visible spectrophotometer (JASCO Corporation, FP-8600 model) was used to measure the toluene solution. The liquid was placed in a quartz cell and measurements were carried out at room temperature. Using a meter (FS920 manufactured by Hamamatsu Photonics Inc.), the toluene solution was placed in a quartz cell and the The measurement results of the absorption spectrum and emission spectrum are shown in Figure 19. The horizontal axis represents the wavelength, and the vertical axis represents the absorbance and emission intensity. where the thin solid line indicates the absorption spectrum and the thick solid line indicates the emission spectrum. The absorbance shown in Figure 19 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured by placing only toluene in a quartz cell was subtracted from the absorption spectrum measured by the quartz cell. is doing.

[0368] As shown in Figure 19, mmtBumTPFBi-02 has an emission peak at 392 nm. there was.

[0369] Next, the mmtBumTPFBi-02 obtained in this example was analyzed by liquid chromatography mass spectrometry. (Liquid Chromatography Mass Spectrometry The analysis was performed using LC / MS (abbreviation: LC / MS analysis).

[0370] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0371] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPFBi-02 at a desired concentration in an organic solvent. The injection volume was 5.0 μL.

[0372] By PRM, the ion m / z=814.5 derived from mmtBumTPFBi-02 was detected. 3 MS 2 The PRM settings were as follows: the mass range of the target ion was m / z = 8 14.53±2.0 (isolation window=4), and the detection was positive. The energy NCE (N The measurement was performed with the normalized collision energy (COE) set at 50. The MS spectrum obtained is shown in FIG.

[0373] In addition, the refractive index of mmtBumTPFBi-02 was measured using a spectroscopic ellipsometer (J. The results of measurements using a Woollam Japan M-2000U are shown below. The materials for each layer were deposited on a quartz substrate to a thickness of approximately 50 nm by vacuum deposition. The figure shows the refractive index of ordinary light, n, Ordinary, and the refractive index of extraordinary light, n, It was described as "extra-ordinary."

[0374] From this figure, mmtBumTPFBi-02 emits light in the blue light region (wavelengths of 455 nm to 465 nm). nm or less) The refractive index of ordinary light in the entire range of light is 1.71 to 1.72, and is 1.50 to 1.75 The refractive index of ordinary light at a wavelength of 633 nm is 1.65 and 1.45. The refractive index was found to be in the range of 1.70 or less, indicating that the material has a low refractive index.

[0375] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPFBi-02 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan Co., Ltd., PYRIS1 Using a DSC, the powder was placed on an aluminum cell and measured. The Tg of i-02 was 126°C. [Example]

[0376] <Synthesis Example 3> In this example, N -(1,1'-biphenyl-2-yl)-N-(3,3'',5',5''-tetra-t ert-butyl-1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl Synthesis of benzoyl-9H-fluoren-2-amine (abbreviation: mmtBumTPoFBi-02) The structure of mmtBumTPoFBi-02 is shown below.

[0377] [ka]

[0378] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0379] Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 1.

[0380] Step 3: 3-Bromo-3'',5,5',5''-tetra-tert-butyl- Synthesis of 1':3',1''-terphenyl The synthesis was carried out in the same manner as in Step 3 of Synthesis Example 1.

[0381] <Step 4: Synthesis of mmtBumTPoFBi-02> The 3-bromo-3'',5,5',5''-tetra- tert-Butyl-1,1':3',1''-terphenyl 5.8g (10.9mmol ), N-(1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H -Fluoren-2-amine 3.9g (10.9mmol), sodium tert-butoxide 3.1 g (32.7 mmol) of cid and 55 mL of toluene were added and degassed under reduced pressure. After that, the atmosphere in the flask was replaced with nitrogen, and bis(dibenzylideneacetone)palladium(0) 64m g (0.11 mmol), tri-tert-butylphosphine 132 mg (0.65 mm ol) was added and heated at 80°C for about 2 hours. After that, the temperature of the flask was returned to about 60°C. Approximately 1 mL of water was added, and the precipitated solid was filtered off and washed with toluene. The filtrate was concentrated to obtain The resulting toluene solution was purified by silica gel column chromatography. The mixture was concentrated to give a concentrated toluene solution. Ethanol was added to the toluene solution, and the mixture was concentrated under reduced pressure. The precipitate was filtered at about 20°C, and the resulting solid was reduced in water at about 80°C. After drying under pressure, 8.1 g of the target white solid was obtained in a yield of 91%. The synthesis scheme of FBi-02 is shown below.

[0382] [ka]

[0383] The white powder obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) The graphs in Figure 22(A) and (B) show the difference between 6.5 ppm and 1.5 ppm in Figure 22(A). The graph shows an enlarged range from 0.5 to 8.0 ppm. The numerical data is also shown below. Therefore, 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 was synthesized.

[0384] 1 H-NMR.δ(CDCl3):7.56(d,1H,J=7.4Hz),7.50( dd,1H,J=1.7Hz),7.33-7.46(m,11H),7.27-7.2 9(m,2H),7.22(dd,1H,J=2.3Hz),7.15(d,1H,J= 6.9Hz),6.98-7.07(m,7H),6.93(s,1H),6.84(d ,1H,J=6.3Hz),1.38(s,9H),1.37(s,18H),1.31 (s,6H),1.20(s,9H).

[0385] Next, 8.0 g of the obtained white solid was subjected to a train sublimation method under a pressure of 3.4 Pa. The product was purified by sublimation under the conditions of an argon flow rate of 15.0 mL / min and a temperature of 260°C. 7.1 g of a pale yellow solid was obtained with a recovery rate of 89%.

[0386] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPoFBi-02 (hereinafter The absorption spectrum (simply referred to as "absorption spectrum") and the emission spectrum were measured. The measurement was carried out using an ultraviolet-visible spectrophotometer (JASCO Corporation, FP-8600 model) and The solution was placed in a quartz cell and measurements were carried out at room temperature. Using a thermometer (FS920 manufactured by Hamamatsu Photonics Inc.), the toluene solution was placed in a quartz cell, The measurements were carried out at room temperature. The absorption and emission spectra are shown in Figure 23. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. Lines are shown, with the thin solid line representing the absorption spectrum and the thick solid line representing the emission spectrum. The absorbance shown in Figure 23 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured with only toluene in a quartz cell was subtracted from the absorption spectrum measured with toluene alone. It shows.

[0387] As shown in Figure 23, mmtBumTPoFBi-02 has an emission peak at 403 nm. was.

[0388] Next, the mmtBumTPoFBi-02 obtained in this example was analyzed by liquid chromatography mass spectrometry. Analysis(Liquid Chromatography Mass Spectrometer The samples were analyzed by LC / MS analysis.

[0389] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0390] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPoFBi-02 at a desired concentration in an organic solvent. The injection volume was 5.0 μL.

[0391] By PRM, the ion m / z=814 originating from mmtBumTPoFBi-02 was detected. 53 MS 2 The PRM settings were as follows: the mass range of the target ions was m / z = 814.53±2.0 (isolation window=4), and the detection was positive. The energy NCE ( The normalized collision energy was set at 60. The MS spectrum obtained is shown in FIG.

[0392] In addition, the refractive index of mmtBumTPoFBi-02 is measured using a spectroscopic ellipsometer (Gene The results of measurements using a meter (M-2000U manufactured by A. Woollam Japan) are shown below. The materials for each layer were deposited on a quartz substrate to a thickness of approximately 50 nm by vacuum deposition. The figure shows the refractive index of ordinary light, n, Ordinary, and the refractive index of extraordinary light, n , and described as Extra-ordinary.

[0393] From this figure, mmtBumTPoFBi-02 emits light in the blue light region (wavelengths of 455 nm or more, 46 5nm or less) The refractive index of ordinary light in the entire range of light is 1.69 to 1.70, and 1.50 to 1.7 5 or less, and the ordinary refractive index at a wavelength of 633 nm is 1.64. The refractive index was found to be in the range of 5 or more and 1.70 or less, indicating that the material has a low refractive index.

[0394] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPoFBi-02 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan, PYRIS Using a DSC, the powder was placed on an aluminum cell and measured. The Tg of FBi-02 was 126°C. [Example]

[0395] <Synthesis Example 4> In this example, N -(4-cyclohexylphenyl)-N-(3,3'',5',5''-tetra-tert- t-Butyl-1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl- Synthesis of 9H-fluoren-2-amine (mmtBumTPchPAF-02) The structure of mmtBumTPchPAF-02 is shown below.

[0396] [ka]

[0397] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0398] Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 1.

[0399] Step 3: 3-Bromo-3'',5,5',5''-tetra-tert-butyl- Synthesis of 1':3',1''-terphenyl The synthesis was carried out in the same manner as in Step 3 of Synthesis Example 1.

[0400] <Step 4: Synthesis of mmtBumTPchPAF-02> The 3-bromo-3'',5,5',5''-tetra- tert-Butyl-1,1':3',1''-terphenyl 3.0g (5.6mmol) , N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluorene- 2-yl)amine 2.1 g (5.6 mmol), sodium tert-butoxide 1.6 g (16.9 mmol) and 28 mL of toluene were added, and the mixture was degassed under reduced pressure. The inside of the container was replaced with nitrogen, and 65 mg (0.1 1mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 1 39 mg (0.34 mmol) of HCl was added and heated at 80°C for about 2 hours. Return the temperature to about 60°C, add about 1 mL of water, filter off the precipitated solid, and wash 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. The mixture was concentrated under reduced pressure to give an ethanol suspension. The precipitate was filtered at about 20°C. The solid was dried under reduced pressure at about 80°C to obtain 3.7 g of the target white solid in a yield of 80%. The synthetic scheme for mmtBumTPchPAF-02 is shown below.

[0401] [ka]

[0402] The white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) The graphs in Figure 26(A) and (B) show the difference between 6.5 ppm and 1.5 ppm in Figure 26(A). The graph shows an enlarged range from 0.5 to 8.0 ppm. The numerical data is also shown below. From this, it can be seen that mmtBumTPchPAF-02 was successfully synthesized in this synthesis example. It was.

[0403] 1 H-NMR.δ(CDCl3):7.62(d,1H,J=7.5Hz),7.56( d,1H,J=8.0Hz),7.50(dd,1H,J=1.7Hz),7.46-7 .47(m,2H),7.43(dd,1H,J=1.7Hz),7.37-7.39( m,3H),7.29-7.32(m,2H),7.23-7.25(m,2H),7. 20(dd,1H,J=1.7Hz),7.09-7.14(m,5H),7.05(d d,1H,J=2.3Hz),2.46(brm,1H),1.83-1.88(m,4 H),1.73-1.75(brm,1H),1.42(s,6H),1.38(s,9 H), 1.36(s,18H), 1.29(s,9H)

[0404] Next, 3.5 g of the obtained white solid was subjected to a train sublimation method under a pressure of 4.0 Pa. The product was purified by sublimation under the conditions of an argon flow rate of 15.0 mL / min and a temperature of 265°C. 3.1 g of a pale yellow solid was obtained with a recovery rate of 89%.

[0405] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPchPAF-02 (hereafter The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The measurements were performed using a UV-visible spectrophotometer (JASCO Corporation, FP-8600 model) and a The fluorine solution was placed in a quartz cell and measurements were carried out at room temperature. Using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Inc.), the toluene solution was placed in a quartz cell. The measurement was carried out at room temperature. The obtained absorption spectrum and emission spectrum are shown in FIG. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. Solid lines are shown, with the thin solid line representing the absorption spectrum and the thick solid line representing the emission spectrum. The absorbance shown in Figure 27 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured with only toluene in a quartz cell was subtracted from the spectrum. This shows:

[0406] As shown in Figure 27, mmtBumTPchPAF-02 has an emission peak at 395 nm. was doing.

[0407] Next, the mmtBumTPchPAF-02 obtained in this example was analyzed by liquid chromatography mass spectrometry. Analysis(Liquid Chromatography Mass Spectromet The samples were analyzed by LC / MS analysis.

[0408] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0409] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPchPAF-02 at a desired concentration in an organic solvent. The injection volume was adjusted to 5.0 μL.

[0410] By PRM, the ion m / z=820 derived from mmtBumTPchPAF-02 was detected. .58 MS 2 The PRM settings were as follows: m / z =820.58±2.0 (isolation window=4), and the detection was positive. The energy used to accelerate the target ions in the collision cell was NCE. The normalized collision energy was set at 60. The resulting MS spectrum is shown in FIG.

[0411] In addition, the refractive index of mmtBumTPchPAF-02 was measured using a spectroscopic ellipsometer (Fig. 29). The results of measurements using a AA Woollam Japan M-2000U are shown below. For the measurement, a film of about 50 nm thickness was formed on a quartz substrate by vacuum deposition of the material of each layer. In addition, the figure shows the refractive index of ordinary rays, n, Ordinary, and the refractive index of extraordinary rays, n, Extra-ordinary.

[0412] From this figure, mmtBumTPchPAF-02 emits light in the blue region (wavelengths of 455 nm or more). 65nm or less) The refractive index for ordinary light in the entire range of light is 1.67 to 1.68, and 1.50 or more. The refractive index for ordinary light at a wavelength of 633 nm is 1.62, which is in the range of 1.75 or less. The refractive index was found to be in the range of 45 to 1.70, making it a low-refractive-index material.

[0413] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPchPAF-02 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan Co., Ltd., PYRI Using S1DSC, the powder was placed on an aluminum cell and measured. The Tg of chPAF-02 was 127°C. [Example]

[0414] <Synthesis Example 5> In this example, N -(1,1'-biphenyl-2-yl)-N-(3'',5',5''-tri-tert -butyl-1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl-9 Regarding the synthesis method of H-fluorene-2-amine (abbreviation: mmtBumTPoFBi-03) The structure of mmtBumTPoFBi-03 is shown below.

[0415] [ka]

[0416] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0417] Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 1.

[0418] Step 3: 3-Bromo-3'',5',5''-tri-tert-butyl-1,1' Synthesis of 3',1''-terphenyl The 2-(3',5,5'-tri-tert-butyl[ 1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-di Oxaborolane 10.0 g (22.3 mmol), 1-bromo-3-iodobenzene 12 0.8g (26.8mmol), potassium carbonate 9.2g (66.9mmol), toluene 1 12mL, 45mL of ethanol, and 33mL of tap water were added, and the mixture was degassed under reduced pressure. The inside of the LASCO was replaced with nitrogen, and 100 mg (0.44 mmol) of palladium acetate and triphenyl 233 mg (0.89 mmol) of phosphine was added, and the mixture was heated at 80° C. for about 10 hours. After that, the temperature was returned to room temperature and the organic layer and aqueous layer were separated. The resulting hexane solution was purified by silica gel column chromatography. The target product, a white solid, was obtained in 9.4 g with a yield of 89%. The formula is shown below.

[0419] [ka]

[0420] <Step 4: Synthesis of mmtBumTPoFBi-03> The 3-bromo-3'',5',5''-tri-tert-butyl ether obtained in Step 3 was placed in a three-neck flask. t-Butyl-1,1':3',1''-terphenyl 4.0 g (8.4 mmol), N- (1,1'-biphenyl-4-yl)-N-phenyl-9,9-dimethyl-9H-fluoro 3.0 g (8.4 mmol) of len-2-amine, 2.4 g of sodium tert-butoxide g (25.2 mmol) and 42 mL of toluene were added, and the mixture was degassed under reduced pressure. The inside of the container was replaced with nitrogen, and 97 mg (0.1 7mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 2 0.7 mg (0.50 mmol) was added and heated at 80°C for about 2 hours. Return the temperature to about 60°C, add about 1 mL of water, filter off the precipitated solid, and wash 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. The mixture was concentrated under reduced pressure to give an ethanol suspension. The precipitate was filtered at about 20°C. The solid was dried under reduced pressure at about 80°C to obtain 3.6 g of the target white solid in a yield of 56%. The synthetic scheme for step 4 is shown below.

[0421] [ka]

[0422] The white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) The graphs in Figure 30(A) and (B) show the difference between 6.5 ppm and 1.5 ppm in Figure 30(A). The graph shows an enlarged range from 0.5 to 8.0 ppm. The numerical data is also shown below. Therefore, N-(1,1'-biphenyl-2-yl)-N-(3'',5',5''- tri-tert-butyl-1,1':3',1''-terphenyl-5-yl)-9,9- It was found that dimethyl-9H-fluoren-2-amine was successfully synthesized.

[0423] 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).

[0424] Next, 3.6 g of the obtained white solid was subjected to a train sublimation method under a pressure of 2.3 Pa. The product was purified by sublimation under the conditions of an argon flow rate of 15.0 mL / min and a temperature of 250°C. 3.1 g of a pale yellow solid was obtained with a recovery rate of 86%.

[0425] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPoFBi-03 (hereinafter The absorption spectrum (simply referred to as "absorption spectrum") and the emission spectrum were measured. The measurement was carried out using an ultraviolet-visible spectrophotometer (JASCO Corporation, FP-8600 model) and The solution was placed in a quartz cell and measurements were carried out at room temperature. Using a thermometer (FS920 manufactured by Hamamatsu Photonics Inc.), the toluene solution was placed in a quartz cell, The measurements were carried out at room temperature. The absorption and emission spectra are shown in Figure 31. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. Lines are shown, with the thin solid line representing the absorption spectrum and the thick solid line representing the emission spectrum. The absorbance shown in Figure 31 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured with only toluene in a quartz cell was subtracted from the absorption spectrum measured with toluene alone. It shows.

[0426] As shown in Figure 31, mmtBumTPoFBi-03 has an emission peak at 403 nm. was.

[0427] Next, the mmtBumTPoFBi-03 obtained in this example was analyzed by liquid chromatography mass spectrometry. Analysis(Liquid Chromatography Mass Spectrometer The samples were analyzed by LC / MS analysis.

[0428] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0429] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPoFBi-03 at a desired concentration in an organic solvent. The injection volume was 5.0 μL.

[0430] By PRM, the ion m / z=758 originating from mmtBumTPoFBi-03 was detected. 47 MS 2 The PRM settings were as follows: the mass range of the target ions was m / z = 758.47±2.0 (isolation window=4), and the detection was positive. The energy NCE ( The normalized collision energy was set at 50. The MS spectrum obtained is shown in FIG.

[0431] In addition, the refractive index of mmtBumTPoFBi-03 is measured using a spectroscopic ellipsometer (Figure 33). The results of measurements using a meter (M-2000U manufactured by A. Woollam Japan) are shown below. The materials for each layer were deposited on a quartz substrate to a thickness of approximately 50 nm by vacuum deposition. The figure shows the refractive index of ordinary light, n, Ordinary, and the refractive index of extraordinary light, n , and described as Extra-ordinary.

[0432] From this figure, mmtBumTPoFBi-03 emits light in the blue light region (wavelengths of 455 nm or more, 46 5nm or less) The refractive index of ordinary light in the entire range of light is 1.69 to 1.70, and 1.50 to 1.7 5 or less, and the ordinary refractive index at a wavelength of 633 nm is 1.64. The refractive index was found to be in the range of 5 or more and 1.70 or less, indicating that the material has a low refractive index. [Example]

[0433] <Synthesis Example 6> In this example, N -(4-cyclohexylphenyl)-N-(3'',5',5''-tri-tert-butyl (ethyl-1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl-9H- Regarding the synthesis method of fluorene-2-amine (abbreviation: mmtBumTPchPAF-03) The structure of mmtBumTPchPAF-03 is shown below.

[0434] [ka]

[0435] Step 1: Synthesis of 3-bromo-3',5,5'-tri-tert-butylbiphenyl > The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1.

[0436] Step 2: 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] Synthesis of ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane > The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 1.

[0437] Step 3: 3-Bromo-3'',5',5''-tri-tert-butyl-1,1' Synthesis of 3',1''-terphenyl The synthesis was carried out in the same manner as in Step 3 of Synthesis Example 5.

[0438] <Step 4: Synthesis of mmtBumTPchPAF-03> The 3-bromo-3'',5',5''-tri-tert-butyl ether obtained in Step 3 was placed in a three-neck flask. t-Butyl-1,1':3',1''-terphenyl 2.3g (4.8mmol), N- (4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl) 1.8 g (4.8 mmol) of sodium tert-butoxide, 1.4 g (1 4.4 mmol) and 24 mL of toluene were added, and the flask was degassed under reduced pressure. Nitrogen-substituted, bis(dibenzylideneacetone)palladium(0) 55 mg (0.10 mm ol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 118m g (0.29 mmol) was added and heated at 80°C for about 2 hours. The temperature was returned to about 60°C, about 1 mL of water was added, and the precipitated solid was separated by filtration 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. The mixture was added to the ethanol solution and concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at about 20°C. The solid was dried under reduced pressure at about 80°C to obtain 2.9 g of the target white solid in a yield of 80%. The synthesis scheme for Step 4 is shown below.

[0439] [ka]

[0440] The white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) The graphs in Figure 34(A) and (B) show the difference between 6.5 ppm and 1.5 ppm in Figure 34(A). The graph shows an enlarged range from 0.5 to 8.0 ppm. The numerical data is also shown below. Therefore, N-(4-cyclohexylphenyl)-N-(3'',5',5''-tri- tert-Butyl-1,1':3',1''-terphenyl-5-yl)-9,9-dimethyl It was found that ethyl-9H-fluoren-2-amine was successfully synthesized.

[0441] 1 H-NMR.δ(CDCl3):7.62(d,1H,J=7.5Hz),7.56( d,1H,J=8.6Hz),7.51(dd,1H,J=1.7Hz),7.48(d d,1H,J=1.7Hz),7.46(dd,1H,J=1.7Hz),7.42(d d,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).

[0442] Next, 2.4 g of the obtained white solid was subjected to a train sublimation method under a pressure of 4.0 Pa. The product was purified by sublimation under the conditions of an argon flow rate of 15.0 mL / min and a temperature of 230°C. 1.9 g of a pale yellow solid was obtained with a recovery rate of 79%.

[0443] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPchPAF-03 (hereafter The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. The measurements were performed using a UV-visible spectrophotometer (JASCO Corporation, FP-8600 model) and a The fluorine solution was placed in a quartz cell and measurements were carried out at room temperature. Using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Inc.), the toluene solution was placed in a quartz cell. The measurement was carried out at room temperature. The obtained absorption spectrum and emission spectrum are shown in Figure 35. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. Solid lines are shown, with the thin solid line representing the absorption spectrum and the thick solid line representing the emission spectrum. The absorbance shown in Figure 35 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured with only toluene in a quartz cell was subtracted from the spectrum. This shows:

[0444] As shown in Figure 35, mmtBumTPchPAF-03 has an emission peak at 399 nm. was doing.

[0445] Next, the mmtBumTPchPAF-03 obtained in this example was analyzed by liquid chromatography mass spectrometry. Analysis(Liquid Chromatography Mass Spectromet The samples were analyzed by LC / MS analysis.

[0446] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0447] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPchPAF-03 at a desired concentration in an organic solvent. The injection volume was adjusted to 5.0 μL.

[0448] By PRM, the ion m / z=764 derived from mmtBumTPchPAF-03 was detected. .52 MS 2 The PRM settings were as follows: m / z =764.52±2.0 (isolation window=4), and the detection was positive. The energy used to accelerate the target ions in the collision cell was NCE. The normalized collision energy was set at 50. The resulting MS spectrum is shown in FIG.

[0449] In addition, the refractive index of mmtBumTPchPAF-03 was measured using a spectroscopic ellipsometer (Fig. 37). The results of measurements using a AA Woollam Japan M-2000U are shown below. For the measurement, a film of about 50 nm thickness was formed on a quartz substrate by vacuum deposition of the material of each layer. In addition, the figure shows the refractive index of ordinary rays, n, Ordinary, and the refractive index of extraordinary rays, n, Extra-ordinary.

[0450] From this figure, mmtBumTPchPAF-03 emits light in the blue region (wavelengths of 455 nm or more). 65nm or less) The refractive index for ordinary light in the entire range of light is 1.69 to 1.70, and 1.50 or more. The refractive index for ordinary light at a wavelength of 633 nm is 1.64, which is in the range of 1.75 or less. The refractive index was found to be in the range of 45 to 1.70, making it a low-refractive-index material. [Example]

[0451] Example 1 In this example, the light-emitting device and the comparative light-emitting device according to one embodiment of the present invention described in the embodiment were The structural formulas of the organic compounds used in this example are shown below.

[0452] [ka]

[0453] (Method for fabricating light-emitting device 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0454] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0455] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0456] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N-(4-cyclohexyl)-2-methyl-2-propanol represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. phenyl)-N-(3,3'',5',5''-tetra-tert-butyl-1,1':3 ',1''-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-a Mn (abbreviation: mmtBumTPchPAF-02) and electron acceptor material (OCHD-0 01) in a weight ratio of 1:0.1 (= mmtBumTPchPAF-02:OCHD-0 01), a hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0457] Next, mmtBumTPchPAF-02 was deposited on the hole injection layer 111 to a thickness of 30 nm. After vapor deposition as described above, N,N-bis[4-(dibenzofuran)] represented by the above structural formula (ii) was -4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) The hole transport layer 112 was formed by vapor deposition to a thickness of 10 nm.

[0458] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)-2-methyl-1-propanol] represented by the above structural formula (iii) αN-βNPAnth) and the above structural formula (iv) 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N -phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3, 10PCA2Nbf(IV)-02) in a weight ratio of 1:0.015 (=αN-βNPAn th:3,10PCA2Nbf(IV)-O2), co-evaporated to a film thickness of 25 nm The light-emitting layer 113 was formed.

[0459] Then, on the light-emitting layer 113, 2-{4-[9,10-di(naphthalene)-2-(4-methylphenyl ... (phthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimide dazole (abbreviation: ZADN) and 8-quinolinolato-rich compound represented by the above structural formula (vi). The weight ratio of ZADN to Liq was 1:1 (= ZADN:Liq), and the film thickness was 25 nm. The electron transport layer 114 was formed by co-evaporation in the same manner.

[0460] After forming the electron transport layer 114, Liq is evaporated to a thickness of 1 nm to form the electron injection layer 115. Next, aluminum is evaporated to a thickness of 200 nm to form a second electrode 102. Thus, the light-emitting device 1 of this example was fabricated.

[0461] (Method for fabricating light-emitting device 2) The light-emitting device 2 is the same as the light-emitting device 1 except that the mmtBumTPchPAF-02 is 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: mmtBum The light-emitting device was fabricated in the same manner as light-emitting device 1, except that the SiO2 was changed to TPoFBi-02.

[0462] (Method for producing comparative light-emitting device 1) Comparative light-emitting device 1 is obtained by replacing mmtBumTPchPAF-02 in light-emitting device 1 with N-(1,1'-biphenyl-4-yl)-N-[4 -(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9 The same as light-emitting device 1 except that H-fluorene-2-amine (abbreviation: PCBBiF) was used. It was made in.

[0463] The device structures of the above light-emitting devices and the comparative light-emitting devices are summarized in the table below.

[0464] [Table 1]

[0465] In addition, the low refractive index material (mmtBumTPchP) used in the hole injection layer and part of the hole transport layer AF-02, and mmtBumTPoFBi-02) and the reference PCBBi The refractive index of F is shown in Figure 38, and the refractive index at 458 nm is shown in the table below.

[0466] [Table 2]

[0467] The light-emitting device and the comparative light-emitting device were placed in a nitrogen atmosphere glove box. The process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealant to the device) After applying it around the device and performing UV treatment and heat treatment at 80°C for 1 hour during sealing, The initial characteristics of the light-emitting device were measured. No special measures were taken on the substrate to improve light extraction efficiency.

[0468] The luminance-current density characteristics of Light-emitting Device 1, Light-emitting Device 2, and Comparative Light-emitting Device 1 are shown in Fig. 39, the current efficiency-luminance characteristics are shown in Fig. 40, the luminance-voltage characteristics are shown in Fig. 41, and the current-voltage characteristics are shown in Fig. 42. The external quantum efficiency-luminance characteristics are shown in FIG. 42, the emission spectrum in FIG. 43, and the emission spectrum in FIG. 1000cd / m for each light-emitting device 2 The main characteristics in the vicinity are shown in Table 3. The CIE chromaticity and emission spectrum were measured using a spectroradiometer (Topcon UR-U The external quantum efficiency was measured using a luminance and emission spectrum. The calculation was performed assuming that the light distribution characteristics were Lambertian type.

[0469] [Table 3]

[0470] 39 to 44 and Table 3, the light-emitting device according to one embodiment of the present invention has an emission spectrum Although the shape is the same, the layer made of low refractive index material makes it superior to the comparative light-emitting device. It was found that the EL device had better luminous efficiency than the conventional device.

[0471] Next, the current density of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1 was 50 mA. / cm 2 FIG. 1 is a graph showing the change in luminance with respect to the driving time when the device is driven at a constant current. As shown in FIG. 67, the light-emitting device according to one embodiment of the present invention exhibits a good lifetime. As a result, the light-emitting device according to one embodiment of the present invention can achieve high light emission while maintaining a good lifespan. It was found to be an efficient light-emitting device. [Example]

[0472] Example 1 In this example, the light-emitting device and the comparative light-emitting device according to one embodiment of the present invention described in the embodiment were The structural formulas of the organic compounds used in this example are shown below.

[0473] [ka]

[0474] (Method for fabricating light-emitting device 3) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0475] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0476] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0477] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N-(4-cyclohexyl)- phenyl)-N-(3'',5',5''-tri-tert-butyl-1,1':3', 1''-terphenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPchPAF-03) and electron acceptor material (OCHD-001 ) in a weight ratio of 1:0.1 (= mmtBumTPchPAF-03:OCHD-001 ) to form a hole injection layer 111 having a thickness of 10 nm.

[0478] Next, mmtBumTPchPAF-03 was deposited on the hole injection layer 111 to a thickness of 30 nm. After vapor deposition as described above, N,N-bis[4-(dibenzofuran)] represented by the above structural formula (ii) was -4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) The hole transport layer 112 was formed by vapor deposition to a thickness of 10 nm.

[0479] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)-2-methyl-1-propanol] represented by the above structural formula (iii) αN-βNPAnth) and the above structural formula (iv) 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N -phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3, 10PCA2Nbf(IV)-02) in a weight ratio of 1:0.015 (=αN-βNPAn th:3,10PCA2Nbf(IV)-O2), co-evaporated to a film thickness of 25 nm The light-emitting layer 113 was formed.

[0480] Then, on the light-emitting layer 113, 2-{4-[9,10-di(naphthalene)-2-(4-methylphenyl ... (phthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimide dazole (abbreviation: ZADN) and 8-quinolinolato-rich compound represented by the above structural formula (vi). The weight ratio of ZADN to Liq was 1:1 (= ZADN:Liq), and the film thickness was 25 nm. The electron transport layer 114 was formed by co-evaporation in the same manner.

[0481] After forming the electron transport layer 114, Liq is evaporated to a thickness of 1 nm to form the electron injection layer 115. Next, aluminum is evaporated to a thickness of 200 nm to form a second electrode 102. Thus, the light-emitting device 3 of this example was fabricated.

[0482] (Method for fabricating light-emitting device 4) The light-emitting device 4 is the same as the light-emitting device 3 except that the mmtBumTPchPAF-03 is N-(1,1'-biphenyl-2-yl)-N-(3'',5'-biphenyl) represented by structural formula (x) ,5''-tri-tert-butyl-1,1':3',1''-terphenyl-5-yl )-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPoFB i-03) was used, the same fabrication method as for light-emitting device 3 was used.

[0483] (Method for producing comparative light-emitting device 2) Comparative light-emitting device 2 is a comparison of mmtBumTPchPAF-03 in light-emitting device 3, N-(1,1'-biphenyl-4-yl)-N-[4 -(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9 The same as light-emitting device 3 except that H-fluorene-2-amine (abbreviation: PCBBiF) was used. It was made in.

[0484] The device structures of the above light-emitting devices and the comparative light-emitting devices are summarized in the table below.

[0485] [Table 4]

[0486] In addition, the low refractive index material (mmtBumTPchP) used in the hole injection layer and part of the hole transport layer AF-03, and mmtBumTPoFBi-03) and the reference PCBBi The refractive index of F is shown in FIG. 45, and the refractive index at 457 nm is shown in the table below.

[0487] [Table 5]

[0488] The light-emitting device and the comparative light-emitting device were placed in a nitrogen atmosphere glove box. The process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealant to the device) After applying it around the device and performing UV treatment and heat treatment at 80°C for 1 hour during sealing, The initial characteristics of the light-emitting device were measured. No special measures were taken on the substrate to improve light extraction efficiency.

[0489] The luminance-current density characteristics of light-emitting device 3, light-emitting device 4, and comparative light-emitting device 2 are shown in Fig. The current efficiency-luminance characteristics are shown in Figure 46, the luminance-voltage characteristics are shown in Figure 47, and the current-voltage characteristics are shown in Figure 48. The external quantum efficiency-luminance characteristics are shown in FIG. 49, FIG. 50, and the emission spectrum in FIG. 51. 1000cd / m for each light-emitting device2 The main characteristics in the vicinity are shown in Table 6. The CIE chromaticity and emission spectrum were measured using a spectroradiometer (Topcon UR-U The external quantum efficiency was measured using a luminance and emission spectrum. The calculation was performed assuming that the light distribution characteristics were Lambertian type.

[0490] [Table 6]

[0491] 46 to 51 and Table 6, the light-emitting device according to one embodiment of the present invention has an emission spectrum Although the shape is almost the same, the comparative light-emitting device has a layer made of a low refractive index material. It was found that the EL device had better luminous efficiency than the conventional device. [Example]

[0492] Example 1 In this example, the light-emitting device and the comparative light-emitting device according to one embodiment of the present invention described in the embodiment were The structural formulas of the organic compounds used in this example are shown below.

[0493] [ka]

[0494] (Method for fabricating light-emitting device 5) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was 2 mm x 2 mm.

[0495] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0496] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0497] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N-(4-cyclohexyl)-2-methyl-2-propanol represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. phenyl)-N-(3,3'',5',5''-tetra-tert-butyl-1,1':3 ',1''-terphenyl-5-yl)-9,9-dimethyl-9H-fluorene-2-a Mn (abbreviation: mmtBumTPchPAF-02) and electron acceptor material (OCHD-0 01) in a weight ratio of 1:0.1 (= mmtBumTPchPAF-02:OCHD-0 01), a hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0498] Next, mmtBumTPchPAF-02 was deposited on the hole injection layer 111 to a thickness of 50 nm. The hole transport layer 112 was formed by vapor deposition in the following manner.

[0499] Next, 9-[3'-(dibenzothiophen-4-yl) biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation N-(1,1'-biphenyl) represented by the above structural formula (viii) phenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] [phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) and phosphorescent dopant OCPG-006 in a weight ratio of 0.6:0.5:0.05 (=9mDB tBPNfpr:PCBBiF:OCPG-006), co-evaporated to a film thickness of 40 nm Thus, the light-emitting layer 113 was formed.

[0500] Thereafter, 9mDBtBPNfpr was evaporated onto the light-emitting layer 113 to a thickness of 30 nm. , 2,9-di(2-naphthyl)-4,7-diphenyl- represented by the above structural formula (xii) 1,10-phenanthroline (abbreviation: NBPhen) was evaporated to a film thickness of 15 nm. Thus, the electron transport layer 114 was formed.

[0501] After forming the electron transport layer 114, lithium fluoride (abbreviation: LiF) is deposited to a thickness of 1 nm. The electron injection layer 115 is formed, and then aluminum is evaporated to a thickness of 200 nm. In this way, the second electrode 102 was formed, and the light-emitting device 5 of this example was fabricated.

[0502] (Method for fabricating light-emitting device 6) The light-emitting device 6 is the same as the light-emitting device 5 except that the mmtBumTPchPAF-02 is 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: mmtBum The light-emitting device was fabricated in the same manner as in device 5, except that the SiO2 was changed to TPoFBi-02.

[0503] (Method for fabricating light-emitting device 7) The light-emitting device 7 is the same as the light-emitting device 5 except that the mmtBumTPchPAF-02 is N-(4-cyclohexylphenyl)-N-(3'',5', 5''-tri-tert-butyl-1,1':3',1''-terphenyl-5-yl -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPchPA F-03) was used.

[0504] (Method for fabricating light-emitting device 8) The light-emitting device 8 is the same as the light-emitting device 5 except that the mmtBumTPchPAF-02 is N-(1,1'-biphenyl-2-yl)-N-(3'',5'-biphenyl) represented by structural formula (x) ,5''-tri-tert-butyl-1,1':3',1''-terphenyl-5-yl )-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mmtBumTPoFB i-03) was used, the same fabrication method as for light-emitting device 5 was used.

[0505] (Method for producing comparative light-emitting device 3) Comparative light-emitting device 3 is a comparison of mmtBumTPchPAF-02 in light-emitting device 5, The light-emitting device was fabricated in the same manner as in Light-emitting Device 5, except that PCBBiF was used.

[0506] The device structures of the above light-emitting devices and the comparative light-emitting devices are summarized in the table below.

[0507] [Table 7]

[0508] In addition, the low refractive index material (mmtBumTPchP) used in the hole injection layer and part of the hole transport layer AF-02, mmtBumTPoFBi-02, mmtBumTPchPAF-03, and The refractive index of the PCBBiF is shown in Fig. 1. 52 and the refractive index at 629 nm is shown in the table below.

[0509] [Table 8]

[0510] The light-emitting device and the comparative light-emitting device were placed in a nitrogen atmosphere glove box. The process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealant to the device) After applying it around the device and performing UV treatment and heat treatment at 80°C for 1 hour during sealing, The initial characteristics of the light-emitting device were measured. No special measures were taken on the substrate to improve light extraction efficiency.

[0511] 1 shows the luminance-current density characteristics of light-emitting devices 5 to 8 and comparative light-emitting device 3. 53, current efficiency vs. luminance characteristics are shown in Fig. 54, luminance vs. voltage characteristics are shown in Fig. 55, and current vs. voltage characteristics are shown in Fig. 56. The external quantum efficiency-luminance characteristics are shown in Figure 56, Figure 57, and the emission spectrum in Figure 58. 1000cd / m for each light-emitting device 2 The main characteristics in the vicinity are shown in Table 9. The CIE chromaticity and emission spectrum were measured using a spectroradiometer (Topcon UR-UL 1R) was measured at room temperature. The external quantum efficiency was calculated by comparing the measured brightness and emission spectrum. The calculation was performed assuming that the light distribution characteristics are Lambertian type.

[0512] [Table 9]

[0513] 53 to 58 and Table 9, the light-emitting device according to one embodiment of the present invention has an emission spectrum Although the shape is almost the same, the comparative light-emitting device has a layer made of a low refractive index material. It was found that the EL device had better luminous efficiency than the conventional device. [Example]

[0514] Example 1 In this example, the light-emitting device and the comparative light-emitting device according to one embodiment of the present invention described in the embodiment were The structural formulas of the organic compounds used in this example are shown below.

[0515] [ka]

[0516] (Method for fabricating light-emitting device 9) First, silver (Ag), palladium (Pd), and copper (Cu) were deposited on a glass substrate as a reflective electrode. The alloy film (Ag-Pd-Cu (APC) film) was deposited by sputtering to a thickness of 100 nm. After forming a thick film, indium tin oxide containing silicon oxide (ITSO) was sputtered as a transparent electrode. The first electrode 101 was formed by depositing a film with a thickness of 85 nm by a quartz crystal deposition method. The electrode area is 4mm 2 (2mm x 2mm).

[0517] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0518] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0519] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N-(4-cyclohexylphenyl)-N-( 3,3'',5',5''-tetra-tert-butyl-1,1':3',1''-tert-butyl phenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mm The electron acceptor material (OCHD-001) was mixed with the tBumTPchPAF-02 by weight. The ratio is 1:0.05 (=mmtBumTPchPAF-02:OCHD-001). As shown, a hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0520] On the hole injection layer 111, mmtBumTPchPAF-02 was deposited in 3 layers as a first hole transport layer. After 5 nm of deposition, N,N-bis(2-methyl-2-propanediol) represented by the above structural formula (ii) was deposited as a second hole transport layer. [4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation :DBfBB1TP) was evaporated to a thickness of 10 nm to form a hole transport layer 112.

[0521] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)-2-methyl-1-propanol] represented by the above structural formula (iii) αN-βNPAnth) and the above structural formula (iv 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)- N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3 ,10PCA2Nbf(IV)-02) in a weight ratio of 1:0.015 (=αN-βNP Anth: 3,10PCA2Nbf(IV)-O2) was co-evaporated to 25 nm. An optical layer 113 was formed.

[0522] Then, on the light-emitting layer 113, 2-{4-[9,10-di(naphthalene)-2-(4-methylphenyl ... (phthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimide dazole (abbreviation: ZADN) and 8-quinolinolato-rich compound represented by the above structural formula (vi). The weight ratio of ZADN to Liq was 1:1 (= ZADN:Liq) and the film thickness was 25 nm. The electron transport layer 114 was formed by co-evaporation.

[0523] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form the electron injection layer 1 15 was formed, and the volume ratio of silver (Ag) to magnesium (Mg) was 10:1, and the film thickness was 15 nm. The second electrode 102 was formed by co-evaporation so as to form the light-emitting device 9. The second electrode 102 is a semi-transparent / semi-reflective electrode having a function of reflecting light and a function of transmitting light. The light emitting device of this embodiment is a top-emitting electrode that extracts light from the second electrode 102. The second electrode 102 is provided with a 1-layer structure represented by the structural formula (xi). ,3,5-tri(dibenzothiophen-4-yl)-benzene (abbreviation: DBT3P-II ) is evaporated to a thickness of 70 nm to improve light extraction efficiency.

[0524] (Method of Making Light-Emitting Device 10) The light emitting device 10 is the same as the light emitting device 9 except that the mmtBumTPchPAF-02 is 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: mmtBum The fabrication was the same as for light-emitting device 9, except that the SiO2 was changed to TPoFBi-02.

[0525] (Method for producing comparative light-emitting device 4) Comparative light-emitting device 4 is the same as the mmtBumTPchPAF-02 in light-emitting device 9. N-(1,1'-biphenyl-4-yl)-N-[4-( 9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H- The material was changed to fluorene-2-amine (abbreviation: PCBBiF), and the thickness of the first hole transport layer was increased to 30 The device was fabricated in the same manner as light-emitting device 9, except that the thickness was changed to nm.

[0526] The device structures of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4 are summarized in the table below. I got it.

[0527] [Table 10]

[0528] In addition, the low refractive index material (mmtBumTPchP) used in the hole injection layer and part of the hole transport layer AF-02 and mmtBumTPoFBi-02) and the reference PCBBiF The refractive index at 458 nm is shown in Figure 59, and the refractive index at 458 nm is shown in the table below.

[0529] [Table 11]

[0530] The light-emitting device and the comparative light-emitting device were placed in a nitrogen atmosphere glove box. The process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealant to the device) After applying the coating around the device and performing UV treatment during sealing, the initial characteristics of these light-emitting devices The sealed glass substrate was coated with a special coating to improve light extraction efficiency. No other measures have been taken.

[0531] The luminance-current density characteristics of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4 are shown in FIG. 60 shows the current efficiency-luminance characteristics, Fig. 61 shows the luminance-voltage characteristics, Fig. 62 shows the current-voltage characteristics. The blue index-luminance characteristics are shown in Figure 63, the blue index-luminance characteristics are shown in Figure 64, and the emission spectrum is shown in Figure 65. 1000cd / m for each light-emitting device 2 The main characteristics in the vicinity are shown in Table 12. A spectroradiometer (Topcon SR-U) was used to measure luminance, CIE chromaticity, and emission spectrum. L1R) was used and measured at room temperature.

[0532] [Table 12]

[0533] 60 to 65 and Table 12, the light-emitting device using the low refractive index material of one embodiment of the present invention The EL device has better current efficiency and blue index (BI) than the comparative light-emitting device. It was found to be a

[0534] The blue index (BI) is calculated by dividing the current efficiency (cd / A) by the chromaticity (y). It is one of the indices that express the luminous characteristics of blue light. The smaller the chromaticity y, the better the blue light. Blue light with high color purity tends to be emitted even if the luminance component is small. It is possible to express a wide range of blue colors, and by using blue light with high color purity, The brightness required to express colors is reduced, which has the effect of reducing power consumption. Therefore, BI, which takes into account chromaticity y, which is one of the indicators of blue purity, is used as a means to express the efficiency of blue light emission. The higher the BI of a light-emitting device, the more suitable it is for use as a blue-emitting device in a display. It can be said that the chair has good efficiency.

[0535] Next, the current density of the light-emitting device 9, the light-emitting device 10, and the comparative light-emitting device 4 was measured at 50 mV. A / cm 2 The graph showing the change in brightness with respect to the driving time when the constant current driving was performed is As shown in FIG. 66, the light-emitting device according to one embodiment of the present invention has a good life span. It was found that the device exhibited high luminous efficiency while retaining its original structure. [Example]

[0536] Example 1 In this example, the light-emitting device and the comparative light-emitting device according to one embodiment of the present invention described in the embodiment were The structural formulas of the organic compounds used in this example are shown below.

[0537] [ka]

[0538] (Method for fabricating light-emitting device 11) First, silver (Ag) was deposited on a glass substrate by sputtering to form a reflective electrode. After forming a film with a thickness of 100 nm, indium tin oxide containing silicon oxide (ITSO) was deposited as a transparent electrode. ) was deposited by sputtering to a thickness of 10 nm to form the first electrode 101. The electrode area is 4 mm 2 (2mm x 2mm).

[0539] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0540] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0541] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N-(4-cyclohexylphenyl)-N-( 3,3'',5',5''-tetra-tert-butyl-1,1':3',1''-tert-butyl phenyl-5-yl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: mm The electron acceptor material (OCHD-001) was mixed with the tBumTPchPAF-02 by weight. The ratio should be 1:0.1 (=mmtBumTPchPAF-02:OCHD-001). A hole injection layer 111 was formed to a thickness of 10 nm by co-evaporation.

[0542] On the hole injection layer 111, mmtBumTPchPAF-02 was deposited as a first hole transport layer. After evaporating 25 nm of N,N-bis(2-methyl-N ... bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation A hole transport layer 112 was formed by depositing a 10 nm thick film of DBfBB1TP.

[0543] Subsequently, 3,3'-(naphthalene)-1,3'-dimethyl-2,3'-dimethyl ... (9-phenyl-9H-carbazole) (PCzN2) was evaporated to a thickness of 10 nm to form an electron blocking layer.

[0544] Then, 2-(10-phenyl-9-anthracenyl) )-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA) and the above 3,10-bis[N-(9-phenyl-9H-carbazole- 2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofura (abbreviation: 3,10PCA2Nbf(IV)-02) in a weight ratio of 1:0.015 (= Bnf(II)PhA:3,10PCA2Nbf(IV)-02) 25nm The light-emitting layer 113 was formed by co-evaporation.

[0545] Thereafter, on the light-emitting layer 113, 2-[3'-(9,9-diphenyl)-2-(2-methyl-2-propanol)-1-one represented by the above structural formula (xiv) was Methyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6- Diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) was deposited at 10 nm, and hole blocking The layer was formed as a 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenyl)- [anthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mP n-mDMePyPTzn) and 8-quinolinolato-liquid represented by the above structural formula (vi). (abbreviation: Liq) in a weight ratio of 1:1 (=mPn-mDMePyPTzn:Liq ) were co-evaporated to form an electron transport layer 114 having a thickness of 20 nm.

[0546] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm. The electron injection layer 115 is formed by depositing silver (Ag) and magnesium (Mg) at a volume ratio of 10 1. A second electrode 102 is formed by co-evaporation to a thickness of 15 nm, and a light-emitting device is formed. The second electrode 102 has both a function of reflecting light and a function of transmitting light. The light emitting device of this embodiment emits light from the second electrode 102. The second electrode 102 is a top-emission element that extracts light having the above structural formula. 1,3,5-tri(dibenzothiophen-4-yl)-benzene (abbreviation) represented by (xi) A 70nm layer of DBT3P-II is deposited on the substrate to improve light extraction efficiency.

[0547] (Method of Making Light-Emitting Device 12) The light emitting device 12 is configured to use the mmtBumTPchPAF-02 in the light emitting device 11 as an upper N-(1,1'-biphenyl-2-yl)-N-(3,3 5',5''-Tetra-tert-butyl-1,1':3',1''-terpheny (5-yl)-9,9-dimethyl-9H-fluoren-2-amine (mmtBu The thickness of the first hole transport layer was changed to 130 nm. It was made in the same way as Vice 11.

[0548] (Method for producing comparative light-emitting device 5) Comparative light-emitting device 5 is a comparison of mmtBumTPchPAF-02 in light-emitting device 11. N-(1,1'-biphenyl-4-yl)-N-[4- (9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H -fluorene-2-amine (abbreviation: PCBBiF), and the thickness of the first hole transport layer was 1 The light-emitting device was fabricated in the same manner as in light-emitting device 11, except that the thickness was set to 00 nm.

[0549] The device structures of light-emitting device 11, light-emitting device 12, and comparative light-emitting device 5 are shown in the table below. Stopped.

[0550] [Table 13]

[0551] In addition, the low refractive index material (mmtBumTPchP) used in the hole injection layer and part of the hole transport layer AF-02 and mmtBumTPoFBi-02) and the reference PCBBiF The refractive index at 458 nm is shown in Figure 68, and the refractive index at 458 nm is shown in the table below.

[0552] [Table 14]

[0553] The light-emitting device and the comparative light-emitting device were placed in a nitrogen atmosphere glove box. The process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealant to the device) After applying the coating around the device and performing UV treatment during sealing, the initial characteristics of these light-emitting devices The sealed glass substrate was coated with a special coating to improve light extraction efficiency. No other measures have been taken.

[0554] The luminance-current density characteristics of light-emitting device 11, light-emitting device 12, and comparative light-emitting device 5 are shown in Table 1. Figure 69 shows the current efficiency vs. luminance characteristics, Figure 70 shows the luminance vs. voltage characteristics, and Figure 71 shows the current density vs. voltage characteristics. The blue index-luminance characteristics are shown in Figure 72, the blue index-luminance characteristics are shown in Figure 73, and the emission spectrum is shown in Figure 74. In addition, each light-emitting device has a luminance of 1000 cd / m 2 The main characteristics of the area are shown in Table 15. The luminance, CIE chromaticity, and emission spectrum were measured using a spectroradiometer (Topcon, S R-UL1R) was used and measured at room temperature.

[0555] [Table 15]

[0556] 69 to 74 and Table 15, the light-emitting devices using the low refractive index material of one embodiment of the present invention The EL device has better current efficiency and blue index (BI) than the comparative light-emitting device. It was found to be a

[0557] The blue index (BI) is calculated by dividing the current efficiency (cd / A) by the chromaticity (y). It is one of the indices that express the luminous characteristics of blue light. The smaller the chromaticity y, the better the blue light. Blue light with high color purity tends to be emitted even if the luminance component is small. It is possible to express a wide range of blue colors, and by using blue light with high color purity, The brightness required to express colors is reduced, which has the effect of reducing power consumption. Therefore, BI, which takes into account chromaticity y, which is one of the indicators of blue purity, is used as a means to express the efficiency of blue light emission. The higher the BI of a light-emitting device, the more suitable it is for use as a blue-emitting device in a display. It can be said that the chair has good efficiency.

[0558] Next, the current density 50 mA / cm 2 A graph showing the change in brightness with respect to drive time when driven at a constant current The light-emitting devices 11 and 12 are shown in FIG. The results showed that the luminance of light-emitting device 11 and light-emitting device 12 decreased relatively quickly. Since the luminous efficiency is better than that of the comparative light-emitting device 5, when driven at the same current density, It emits light with a higher brightness than the light-emitting device 5. [Example]

[0559] Example 1 In this example, measurement results of hole mobility of an organic compound according to one embodiment of the present invention will be described. The hole mobility was measured by fabricating a device for measurement. The fabrication method of the device is as follows: Explain the law.

[0560] (Method for fabricating Device 1) On a glass substrate, an alloy film of silver (Ag), palladium (Pd) and copper (Cu) was deposited as an electrode. A Ag-Pd-Cu (APC) film was formed by sputtering to a thickness of 100 nm. After that, indium tin oxide containing silicon oxide (ITSO) was sputtered onto the The first electrode 101 was formed by depositing a film with a thickness of 4 mm. 2 (2 mm x 2 mm).

[0561] Next, as a pretreatment for forming a device on the substrate, the substrate surface was washed with water and then heated at 200 After baking at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0562] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0563] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: mmtBumTPchPAF-02 and molybdenum oxide were mixed by vapor deposition in a weight ratio of 1:1. (=mmtBumTPchPAF-02: molybdenum oxide) Thus, the hole injection layer 111 was formed.

[0564] On the hole injection layer 111, mmtBumTPchPAF-02 was deposited for 5 minutes as a hole transport layer 112. 20 nm was deposited.

[0565] Next, mmtBumTPchPAF-02 and molybdenum oxide were mixed in a weight ratio of 1:1 (= mmtBumTPchPAF-02: Molybdenum oxide) A buffer layer was formed.

[0566] Next, aluminum (Al) was vapor-deposited to a thickness of 200 nm to form a second electrode 1 Device 1 was fabricated by forming a gate insulating film 02, which allows only holes to flow.

[0567] (Method for fabricating Device 2) Device 2 uses mmtBumTPchPAF-02 in Device 1 as mmtBumT The device was changed to PoFBi-02 and the thickness of the hole transport layer 112 was changed to 557.5 nm. It was prepared in the same manner as 1.

[0568] The device structures of Device 1 and Device 2 are summarized in the table below.

[0569] [Table 16]

[0570] The device was placed in a glove box with a nitrogen atmosphere so that the device was not exposed to the atmosphere. The process of sealing the device with a glass substrate (applying a sealant around the device and sealing it) After UV treatment, these devices were measured.

[0571] The current density-voltage characteristics of Device 1 and Device 2 are shown in Figure 76. The measurements were performed at room temperature. went.

[0572] From the electrical characteristics shown in Figure 76, the hole transfer of each organic compound was calculated using device simulation. The simulation was performed using the D The rift-Diffusion module was used. The simulation parameters were The work function of the first electrode 101, ITSO, is set to 5.36 eV, and the work function of the second electrode 102, ITSO, is set to 5.36 eV. The work function of Al is set to 4.2 eV, and the HOMO level of mmtBumTPchPAF-02 is The HOMO level of mmtBumTPoFBi-02 is -5.39 eV, and the HOMO level of mmtBumTPoFBi-02 is -5.43 eV. The charge density in the hole transport layer 112 was set to 1.0×10 18 cm -3 It was decided.

[0573] The work function of the electrode was measured in air by photoelectron spectroscopy (Riken Keiki, AC-2).

[0574] The HOMO levels of organic compounds were measured by cyclic voltammetry (CV). The measurements were carried out using an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). Each compound was dissolved in N,N-dimethylformamide (abbreviated as The solution dissolved in DMF was measured. In the measurement, the potential of the working electrode relative to the reference electrode was The oxidation and reduction peak potentials were obtained by varying the potential within an appropriate range. The redox potential of the pole is estimated to be -4.94 eV, so The HOMO level of each organic compound was calculated from the values ​​and the obtained peak potentials.

[0575] Figure 77 shows the electric field strength dependence of the hole mobility of each organic compound calculated by simulation. The horizontal axis of Figure 77 represents the 1 / 2 power of the electric field strength converted from voltage. 300(V / cm) 1 / 2 The hole mobility at electric field strengths of is shown in the table below.

[0576] [Table 17]

[0577] Thus, the organic compound of one embodiment of the present invention has a 1×10 -6 cm 2 Hole transfer above / Vs Since it is a material with high optical conductivity, it is suitable for use as a hole transport layer in a light-emitting device. [Example]

[0578] <Synthesis Example 7> In this example, an organic compound represented by structural formula (150) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, N-(3'',5',5''-tri-tert-butyl-1,1':3',1'' -terphenyl-4-yl)-N-(1,1'-biphenyl-2-yl)-9,9-dimethyl Synthesis of methyl-9H-fluoren-2-amine (abbreviation: mmtBumTPoFBi-04) The method is explained below. The structure of mmtBumTPoFBi-04 is shown below.

[0579] [ka]

[0580] Step 1: 4-Bromo-3'',5',5''-tri-tert-butyl-1,1' Synthesis of 3',1''-terphenyl A three-neck flask was charged with 2-(3',5,5'-tri-tert-butyl[1,1'-biphenyl] ]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 9.0 g (20.1 mmol), 1-bromo-4-iodobenzene 6.8 g (24.1 mmol) ), potassium carbonate 8.3g (60.3mmol), toluene 100mL, ethanol 40 After degassing under reduced pressure, the flask was purged with nitrogen and Palladium acetate 91 mg (0.40 mmol), triphenylphosphine 211 mg (0. 80 mmol) was added, and the mixture was heated at 80°C for about 4 hours. The organic layer and the aqueous layer were separated. Magnesium sulfate was added to this solution to dry it and concentrate it. The hexane solution obtained was purified by silica gel column chromatography to obtain the target compound. 6.0 g of a white solid was obtained in 62.5% yield. '',5',5''-tri-tert-butyl-1,1':3',1''-terphenyl The synthesis scheme is shown below.

[0581] [ka]

[0582] <Step 2: Synthesis of mmtBumTPoFBi-04> A three-neck flask was charged with 4-bromo-3'',5',5''-tri-tert-butyl-1,1' : 3',1''-terphenyl 3.0g (6.3mmol), N-(1,1'-biphenyl) (4-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine 2. 3g (6.3mmol), sodium tert-butoxide 1.8g (18.9mmol) l) 32 mL of toluene was added, and the flask was degassed under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. , bis(dibenzylideneacetone)palladium(0) 72 mg (0.13 mmol), 76 mg (0.38 mmol) of tri-tert-butylphosphine was added, and the mixture was heated to about The mixture was heated at 120°C for 8 hours, after which the temperature was lowered to about 60°C, and about 1 ml of water was added. The precipitated solid was filtered off and washed with toluene. The filtrate was concentrated, and the obtained toluene was The solution was purified by silica gel column chromatography. Ethanol was added to this toluene solution, and the mixture was concentrated under reduced pressure to obtain a toluene solution. A suspension was obtained, and the precipitate was filtered at about 20°C, and the obtained solid was dried under reduced pressure at about 80°C. The target product, a white solid, was obtained in 3.6 g with a yield of 75%. The synthesis scheme of TPoFBi-04 is shown below.

[0583] [ka]

[0584] The white solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown in Figures 78(A) and (B). Note that Figure 78(B) shows the results of the analysis of 6.5 The graph shows an enlarged range from ppm to 8.0 ppm. This demonstrates that mmtBumTPoFBi-04 was successfully synthesized in this synthesis example. I found out that...

[0585] 1 H-NMR.δ(CDCl3):7.54-7.56(m,1H),7.53(dd, 1H,J=1.7Hz),7.50(dd,1H,J=1.7Hz),7.27-7.4 7(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,9 H), 1.39(s,18H), (1.29(s,6H).

[0586] Next, 3.6 g of the obtained white solid was purified by sublimation using a train sublimation method. The purification was carried out under the conditions of a pressure of 3.9 Pa and an argon flow rate of 15.0 mL / min. After purification by sublimation, 2.1 g of a pale yellowish white solid was obtained with a recovery rate of 58%.

[0587] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPoFBi-04 (hereinafter The absorption spectrum (simply referred to as "absorption spectrum") and the emission spectrum were measured. For the measurement, a UV-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) was used, and the toluene solution was The sample was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorometer ( Using a JASCO FP-8600, the toluene solution was placed in a quartz cell and heated at room temperature. The absorption spectrum and emission spectrum were measured and the measurement results are shown in Figure 79. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. The thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorbance shown in Figure 79 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured by placing only toluene in a quartz cell was subtracted from the results shown in the figure. There are.

[0588] As shown in Figure 79, the organic compound, mmtBumTPoFBi-04, emits light at 396 nm. It had a peak.

[0589] Next, the mmtBumTPoFBi-04 obtained in this example was analyzed by liquid chromatography mass spectrometry. Analysis(Liquid Chromatography Mass Spectrometer The samples were analyzed by LC / MS analysis.

[0590] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0591] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPoFBi-04 at a desired concentration in an organic solvent. The injection volume was 5.0 μL.

[0592] By PRM, the ion m / z=757 originating from mmtBumTPoFBi-04 was identified. 46 MS 2 The PRM settings were as follows: the mass range of the target ions was m / z = 757.46±2.0 (isolation window=4), and the detection was positive. The energy NCE ( The normalized collision energy was set at 50. The MS spectrum obtained is shown in Figure 80.

[0593] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPoFBi-04 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan Co., Ltd., PYRIS1 The powder was placed on an aluminum cell and measured using a DSC. The Tg of Bi-04 was 123°C. [Example]

[0594] <Synthesis Example 8> In this example, an organic compound represented by structural formula (151) in Embodiment 1, which is one embodiment of the present invention, Compound, N-(3'',5',5''-tri-tert-butyl-1,1':3',1'' -terphenyl-4-yl)-N-(4-cyclohexylphenyl)-9,9-dimethyl Synthesis of -9H-fluoren-2-amine (abbreviation: mmtBumTPchPAF-04) The structure of mmtBumTPchPAF-04 is shown below.

[0595] [ka]

[0596] Step 1: 4-Bromo-3'',5',5''-tri-tert-butyl-1,1' Synthesis of 3',1''-terphenyl The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 7.

[0597] <Step 2: Synthesis of mmtBumTPchPAF-04> The 4-bromo-3'',5',5''-tri-tert-butyl ether obtained in Step 1 was placed in a three-neck flask. t-Butyl-1,1':3',1''-terphenyl 3.0 g (6.3 mmol), N- (4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl) 2.3 g (6.3 mmol) of sodium tert-butoxide, 1.8 g (1 8.9 mmol) and 32 mL of toluene were added, and the flask was degassed under reduced pressure. Nitrogen-substituted, bis(dibenzylideneacetone)palladium(0) 72 mg (0.13 mm ol) and tri-tert-butylphosphine 76 mg (0.38 mmol) were added, and The mixture was heated at 80°C for about 2 hours. The temperature of the flask was then returned to about 60°C and about 100% water was added. The precipitated solid was filtered off and washed with toluene. The filtrate was concentrated. The toluene solution was purified by silica gel column chromatography. The resulting solution was concentrated. A concentrated toluene solution was obtained. Ethanol was added to this toluene solution, and the mixture was concentrated under reduced pressure to give ethanol. A solid precipitated in the ethanol suspension at about 20°C was filtered. The solid was dried under reduced pressure at about 80°C to obtain 4.1 g of a white solid, which was the target product, in a yield of 85%. The synthesis scheme of mmtBumTPchPAF-04 is shown below.

[0598] [ka]

[0599] The white solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown in Figure 81(A) and (B). Note that Figure 81(B) shows the results of the analysis of 6.5 The graph shows an enlarged range from ppm to 8.0 ppm. As a result, mmtBumTPchPAF-04 was synthesized in this synthesis example. I found out that...

[0600] 1 H-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).

[0601] Next, 4.1 g of the obtained white solid was purified by sublimation using a train sublimation method. The purification was carried out under the conditions of a pressure of 4.3 Pa and an argon flow rate of 15.0 mL / min. After purification by sublimation, 3.0 g of a pale yellowish white solid was obtained with a recovery rate of 73%.

[0602] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPchPAF-04 (hereafter The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. Measurements were performed using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) and a toluene solution. The sample was placed in a quartz cell and measured at room temperature. (JASCO Corporation FP-8600 type) was used, and the toluene solution was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 82. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. The thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorbance shown in Figure 82 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured by placing only toluene in a quartz cell was subtracted from the above. are.

[0603] As shown in Figure 82, the organic compound, mmtBumTPchPAF-04, emits light at 397 nm. It had a light peak.

[0604] Next, the mmtBumTPchPAF-04 obtained in this example was analyzed by liquid chromatography mass spectrometry. Analysis(Liquid Chromatography Mass Spectromet The samples were analyzed by LC / MS analysis.

[0605] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30 LC (liquid chromatography) separation was performed using 00 and Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fluorescent Technology.

[0606] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was selected appropriately for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPchPAF-04 at a desired concentration in an organic solvent. The injection volume was adjusted to 5.0 μL.

[0607] By PRM, the ion m / z=764 derived from mmtBumTPchPAF-04 was detected. .52 MS 2 The PRM settings were as follows: m / z =764.52±2.0 (isolation window=4), and the detection was positive. The energy used to accelerate the target ions in the collision cell was NCE. The normalized collision energy was set at 50. The resulting MS spectrum is shown in FIG.

[0608] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPchPAF-04 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan Co., Ltd., PYRI Using S1DSC, the powder was placed on an aluminum cell and measured. The Tg of chPAF-04 was 122°C. [Example]

[0609] <Synthesis Example 9> In this example, an organic compound represented by structural formula (175) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, N-(1,1'-biphenyl-2-yl)-N-(3,3'',5''-tri-t ert-butyl-1,1':4',1''-terphenyl-5-yl)-9,9-dimethyl Synthesis of benzoyl-9H-fluoren-2-amine (abbreviation: mmtBumTPoFBi-05) The structure of mmtBumTPoFBi-05 is shown below.

[0610] [ka]

[0611] <Step 1: Synthesis of 4-bromo-3',5'-di-tert-butylbiphenyl> In a three-neck flask, 12.0 g (43 mmol) of 1-bromo-4-iodobenzene and 3,5- Di-tert-butylphenylboronic acid 10.0 g (43 mmol), potassium carbonate 17 0.7g (128mmol), toluene 285mL, ethanol 85mL, tap water 60mL After degassing under reduced pressure, the flask was replaced with nitrogen and tetrakis(triphenylphosphine) 2.5 g (2.1 mmol) of (trimethylphosphine)palladium(0) was added to the mixture, and the mixture was The mixture was heated at 40°C for about 5 hours. After that, the mixture was returned to room temperature and the organic layer and the aqueous layer were separated. Magnesium sulfate was added to dry the water and concentrate. The product was purified by gel column chromatography to give 11.1 g of the desired colorless oil. In addition, 3-bromo-3',5,5'-tri-tert-butyl The synthesis scheme of rubiphenyl is shown below.

[0612] [ka]

[0613] Step 2: 2-(3',5'-di-tert-butyl[1,1'-biphenyl]-4 Synthesis of (-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane The 4-bromo-3',5'-di-tert-butylbiphenyl obtained in Step 1 was placed in a three-neck flask. Phenyl 11.1g (32mmol), 4,4,4',4',5,5,5',5-octa Methyl-2,2'-bi-1,3,2-dioxaborolane 9.0g (35mmol), acetic acid Add 9.5 g (96 mmol) of potassium and 214 mL of N,N-dimethylformamide. After degassing under reduced pressure, the flask was replaced with nitrogen and [1,1'-bis(diphenylphosphine)] Add 1.3 g (1.6 mmol) of [sphino)ferrocene]dichloropalladium(II) The mixture was heated at 100°C for about 3 hours, then cooled to room temperature and the organic layer and aqueous layer were separated. The aqueous layer was extracted with ethyl acetate, and magnesium sulfate was added to the solution to remove water. The toluene solution of the obtained mixture was subjected to silica gel column chromatography. The purified solution was concentrated to obtain a concentrated toluene solution. The mixture was concentrated under reduced pressure to give an ethanol suspension. The precipitate was filtered at about 20°C. The solid was dried under reduced pressure at about 80°C to obtain 11.6 g of the target white solid in a yield of 92%. The synthetic scheme for step 2 is shown below.

[0614] [ka]

[0615] Step 3: 3-Bromo-3′,5,5′-tri-tert-butyl-1,1′: Synthesis of 3',1''-terphenyl A three-neck flask was charged with 2-(3',5'-ditert-butyl[1,1'-biphenyl]-4 -yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 11.6g ( 38.2 mmol), 1,3-dibromo-5-tert-butylbenzene 16.6 g (5 7.3 mmol), potassium carbonate 15.8 g (115 mmol), toluene 255 mL, Add 76 mL of ethanol and 57 mL of tap water, degas the flask under reduced pressure, and then Nitrogen-substituted tetrakis(triphenylphosphine)palladium(0) 2.2g (1. 9 mmol) was added, and the mixture was heated at 80°C for about 10 hours. The organic layer and the aqueous layer were separated. Magnesium sulfate was added to this solution to dry it and concentrate it. The hexane solution obtained was purified by silica gel column chromatography to obtain the target compound. 4.4 g of a white solid was obtained in a yield of 24.4%. ',5,5''-tri-tert-butyl-1,1':3',1''-terphenyl The synthesis scheme is shown below.

[0616] [ka]

[0617] <Step 4: Synthesis of mmtBumTPoFBi-05> In a three-neck flask, 3-bromo-3'',5,5''-tri-tert-butyl-1,1': 3',1''-terphenyl 2.2g (4.6mmol), N-(1,1'-biphenyl -4-yl)-N-phenyl-9,9-dimethyl-9H-fluoren-2-amine 1.7 g (4.6 mmol), sodium tert-butoxide 1.3 g (13.8 mol), 23 mL of toluene was added, and after degassing under reduced pressure, the atmosphere in the flask was replaced with nitrogen. Dibenzylideneacetone)palladium(0) 53 mg (0.10 mmol), tri-te 56 mg (0.28 mmol) of rt-butylphosphine was added, and the mixture was stirred for about 8 hours. The flask was heated to 20°C. After that, the temperature was returned to about 60°C, and about 1 mL of water was added to precipitate the The solid was filtered off and washed with toluene. The filtrate was concentrated, and the resulting toluene solution was added to silica gel. The resulting solution was purified by gel column chromatography. Ethanol was added to this toluene solution, and the mixture was concentrated under reduced pressure to obtain an ethanol suspension. The solid precipitated in this ethanol suspension was filtered at about 20°C, and the resulting solid was heated at about 80°C. After drying under reduced pressure, 2.7 g of the target white solid was obtained in a yield of 77%. The synthesis scheme is shown below.

[0618] [ka]

[0619] The white solid obtained in step 4 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown in Figure 84(A) and (B). Note that Figure 84(B) shows the results of the analysis of 6.5 The graph shows an enlarged range from ppm to 8.0 ppm. From this, it can be seen that mmtBumTPoFBi-05 was successfully synthesized in this synthesis example. I found out that...

[0620] 1 H-NMR.δ(CDCl3):7.56-7.60(m,3H),7.49(d,2 H,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,1.2Hz), 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).

[0621] Next, 2.7 g of the obtained white solid was purified by sublimation using a train sublimation method. The purification was carried out under the conditions of a pressure of 2.9 Pa and an argon flow rate of 15.0 mL / min. After sublimation purification, 2.0 g of a pale yellowish white solid was obtained with a recovery rate of 74%.

[0622] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPoFBi-05 (hereinafter The absorption spectrum (simply referred to as "absorption spectrum") and the emission spectrum were measured. For the measurement, a UV-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) was used, and the toluene solution was The sample was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorometer ( Using a JASCO FP-8600, the toluene solution was placed in a quartz cell and heated at room temperature. The absorption spectrum and emission spectrum were measured and the measurement results are shown in Figure 85. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. The thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorbance shown in Figure 85 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured by placing only toluene in a quartz cell was subtracted from the results shown in the figure. There are.

[0623] As shown in Figure 85, the organic compound, mmtBumTPoFBi-05, emits light at 407 nm. It had a peak.

[0624] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPoFBi-05 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan Co., Ltd., PYRIS1 The powder was placed on an aluminum cell and measured using a DSC. The Tg of Bi-05 was 118°C. [Example]

[0625] <Synthesis Example 10> In this example, an organic compound represented by structural formula (176) in Embodiment 1, which is one embodiment of the present invention, was used. Compound, N-(4-cyclohexylphenyl)-N-(3,3'',5''-tri-tert-butylphenyl) t-Butyl-1,1':4',1''-terphenyl-5-yl)-9,9-dimethyl- Synthesis of 9H-fluoren-2-amine (mmtBumTPchPAF-05) The structure of mmtBumTPchPAF-05 is shown below.

[0626] [ka]

[0627] <Step 1: Synthesis of 4-bromo-3',5'-di-tert-butylbiphenyl> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 9.

[0628] Step 2: 2-(3',5'-di-tert-butyl[1,1'-biphenyl]-4 Synthesis of (-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane The synthesis was carried out in the same manner as in Step 2 of Synthesis Example 9.

[0629] Step 3: 3-Bromo-3′,5,5′-tri-tert-butyl-1,1′: Synthesis of 3',1''-terphenyl The synthesis was carried out in the same manner as in Step 3 of Synthesis Example 9.

[0630] <Step 4: Synthesis of mmtBumTPchPAF-05> The 3-bromo-3'',5,5''-tri-tert-butyl ether obtained in Step 3 was placed in a three-neck flask. -butyl-1,1':3',1''-terphenyl 2.2 g (4.6 mmol), N-( 4-cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl ) amine 1.7g (4.6mmol), sodium tert-butoxide 1.3g (1 3.8 mmol) and 23 mL of toluene were added, and the flask was degassed under reduced pressure. Nitrogen-substituted, bis(dibenzylideneacetone)palladium(0) 53 mg (0.10 mm ol) and 56 mg (0.28 mmol) of tri-tert-butylphosphine were added, and The mixture was heated at 80°C for about 2 hours, after which the temperature of the flask was returned to about 60°C and about 1 liter of water was added. The precipitated solid was filtered off and washed with toluene. The filtrate was concentrated, and the resulting toluene was The ene solution was purified by silica gel column chromatography. A thick toluene solution was obtained. Ethanol was added to this toluene solution, and the mixture was concentrated under reduced pressure to give ethanol. A solid precipitated in the ethanol suspension at about 20°C was filtered. The solid was dried under reduced pressure at about 80°C to obtain 3.2 g of the target white solid in a yield of 91%. The synthesis scheme of mtBumTPchPAF-05 is shown below.

[0631] [ka]

[0632] The white solid obtained in step 4 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown in Figures 86(A) and 86(B). This graph shows an enlarged range from 8.0 ppm to 8.0 ppm. It was found that mmtBumTPchPAF-05 was synthesized.

[0633] 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,6.3H z,2.3Hz),7.04(dd,1H,J=7.9Hz,1.7Hz),2.48- 2.50(brm,1H),1.84-1.93(brm,4H),1.73-1.76 (brm,1H),1.43(s,6H),1.40-1.42(m,4H),1.37 (s,18H). 1.29(s,9H),1.24-1.26(m,1H).

[0634] Next, 3.2 g of the obtained white solid was purified by sublimation using a train sublimation method. The purification was carried out at a pressure of 2.9 Pa and an argon flow rate of 15.0 mL / min. After purification by sublimation, 2.1 g of a pale yellowish white solid was obtained with a recovery rate of 66%.

[0635] Next, the UV-visible absorption spectrum of the toluene solution of mmtBumTPchPAF-05 (hereafter The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum were measured. Measurements were performed using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) and a toluene solution. The sample was placed in a quartz cell and measured at room temperature. (JASCO Corporation FP-8600 type) was used, and the toluene solution was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 87. The horizontal axis represents wavelength, and the vertical axis represents absorbance and luminescence intensity. The thin solid line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorbance shown in Figure 87 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The absorption spectrum measured by placing only toluene in a quartz cell was subtracted from the above. are.

[0636] As shown in Figure 87, the organic compound, mmtBumTPchPAF-05, emits light at 416 nm. It had a light peak.

[0637] Next, the glass transition temperature (hereinafter referred to as "Tg") of mmtBumTPchAPF-05 was measured. Tg was measured using a differential scanning calorimeter (PerkinElmer Japan, PYRIS Using a DSC, the powder was placed on an aluminum cell and measured. The Tg of hAPF-05 was 121°C. [Example]

[0638] <Synthesis Example 11> In this example, an organic compound, N-(1,1'-biphenyl-2-yl)-2-methyl-2-phenylpropanol, which is one embodiment of the present invention, was butyl)-N-(3'',3''',5'',5'''-tetra-t-butyl-1,1':3 ',1'':5',1'''-quaterphenyl-4-yl)-9,9-dimethyl-9H -Describes the synthesis method of fluorene-2-amine (abbreviation: mmtBumQPoFBi) The structure of mmtBumQPoFBi is shown below.

[0639] [ka]

[0640] Step 1: N-(1,1'-biphenyl-2-yl)-N-(1-bromophenyl- Synthesis of (4-yl)-9,9-dimethyl-9H-fluoren-2-amine In a three-neck flask, 10 g ( 28mmol), 1-bromo-4-iodobenzene 17g (55mmol), sodium 4.0 g (42 mmol) of tert-butoxide and 92 mL of toluene were added, and the mixture was decomposed under reduced pressure. After the gas treatment, the atmosphere in the flask was replaced with nitrogen, and bis(dibenzylideneacetone)palladium (0) 1.3 g (1.4 mmol), tri-tert-butylphosphine 0.28 g (1 0.4 mmol) was added and the mixture was heated at 80°C for about 4 hours. The temperature was returned to about 60°C, about 1 mL of water was added, and the precipitated solid was filtered 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. The mixture was concentrated under reduced pressure to give an ethanol suspension. The precipitate was filtered at about 20°C. The solid was dried under reduced pressure at about 80°C to obtain 9.4 g of the target white solid in a yield of 66%. The synthesis scheme for Step 1 is shown below.

[0641] [ka]

[0642] Step 2: 2-(3',3'',5',5''-tetra-tert-butyl[1,1 ':3,1''-terphenyl]-5-yl)-4,4,5,5-tetramethyl-1,3 Synthesis of 2-dioxaborolane A three-neck flask was charged with 5-bromo-3',3'',5',5''-tetra-tert-butyl- 1,1':3,1''-terphenyl 7.0 g (13 mmol), 4,4,4',4', 5,5,5',5-Octamethyl-2,2'-bi-1,3,2-dioxaborolane 3.7 g (14 mmol), potassium acetate 3.9 g (39 mmol), N,N-dimethylform 87 mL of amide was added, and the flask was degassed under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen and [1,1 '-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) 0.53g (0.66 mmol) was added and the mixture was heated at 100° C. for about 3 hours. The temperature was returned to room temperature, and the organic layer and the aqueous layer were separated. The aqueous layer was extracted w...

Claims

1. a first electrode, a second electrode, a light-emitting layer located between the first electrode and the second electrode, and a first layer located between the first electrode and the light-emitting layer; the first layer comprises an arylamine compound; the arylamine compound has a first aromatic group, a second aromatic group, and a third aromatic group; the first 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 to the third benzene ring are directly bonded in this order, the first benzene ring is attached to an amine nitrogen in the arylamine compound; two or more of the first to third benzene rings are each independently bonded at the 1st and 3rd positions to another benzene ring, any of the at least three alkyl groups, or a nitrogen atom of the amine; the second aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted fused ring skeleton having three or less rings, the third aromatic group has one to three substituted or unsubstituted benzene rings, when one or more of the 1 to 3 benzene rings have a substituent, the substituents are each independently any of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms, a layer made of the arylamine compound having an ordinary refractive index of 1.50 or more and 1.75 or less for light with a wavelength of 455 nm or more and 465 nm or less;

2. a first electrode, a second electrode, a light-emitting layer located between the first electrode and the second electrode, and a first layer located between the first electrode and the light-emitting layer; the first layer comprises an arylamine compound; the arylamine compound has a first aromatic group, a second aromatic group, and a third aromatic group; the first 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 to the third benzene ring are directly bonded in this order, the first benzene ring is attached to an amine nitrogen in the arylamine compound; two or more of the first to third benzene rings are each independently bonded at the 1st and 3rd positions to another benzene ring, any of the at least three alkyl groups, or a nitrogen atom of the amine; the second aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted fused ring skeleton having three or less rings, the third aromatic group has one to three substituted or unsubstituted benzene rings, when one or more of the 1 to 3 benzene rings have a substituent, the substituents are each independently any of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms, A light-emitting device, wherein the layer made of the arylamine compound has an ordinary refractive index of 1.45 or more and 1.70 or less for light with a wavelength of 633 nm.

3. a first electrode, a second electrode, a light-emitting layer located between the first electrode and the second electrode, and a first layer located between the first electrode and the light-emitting layer; the first layer comprises an arylamine compound; the arylamine compound has a first aromatic group, a second aromatic group, and a third aromatic group; the first 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 to the third benzene ring are directly bonded in this order, the first benzene ring is attached to an amine nitrogen in the arylamine compound; the second benzene ring or the third benzene ring has a phenyl group substituted with an alkyl group, two or more of the first to third benzene rings are each independently bonded at the 1st and 3rd positions to another benzene ring, a benzene ring of the phenyl group substituted with an alkyl group, any of the at least three alkyl groups, or a nitrogen atom of the amine; the second aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted fused ring skeleton having three or less rings, the third aromatic group has one to three substituted or unsubstituted benzene rings, when one or more of the 1 to 3 benzene rings have a substituent, the substituents are each independently any of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms, a layer made of the arylamine compound having an ordinary refractive index of 1.50 or more and 1.75 or less for light with a wavelength of 455 nm or more and 465 nm or less;

4. a first electrode, a second electrode, a light-emitting layer located between the first electrode and the second electrode, and a first layer located between the first electrode and the light-emitting layer; the first layer comprises an arylamine compound; the arylamine compound has a first aromatic group, a second aromatic group, and a third aromatic group; the first 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 to the third benzene ring are directly bonded in this order, the first benzene ring is attached to an amine nitrogen in the arylamine compound; the second benzene ring or the third benzene ring has a phenyl group substituted with an alkyl group, two or more of the first to third benzene rings are each independently bonded at the 1st and 3rd positions to another benzene ring, a benzene ring of the phenyl group substituted with an alkyl group, any of the at least three alkyl groups, or a nitrogen atom of the amine; the second aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted fused ring skeleton having three or less rings, the third aromatic group has one to three substituted or unsubstituted benzene rings, when one or more of the 1 to 3 benzene rings have a substituent, the substituents are each independently any of an alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms, A light-emitting device, wherein the layer made of the arylamine compound has an ordinary refractive index of 1.45 or more and 1.70 or less for light with a wavelength of 633 nm.

5. In claim 3 or claim 4, A light-emitting device, wherein all of the benzene rings in the first to third benzene rings and the phenyl group substituted with an alkyl group are each independently bonded at the 1st and 3rd positions to another benzene ring, any of the at least three alkyl groups, or a nitrogen of the amine.

6. In claim 3 or claim 4, a light-emitting device, wherein all of the benzene rings in the first to third benzene rings and the phenyl group substituted with an alkyl group are independently bonded to another benzene ring, any of the at least three alkyl groups, or a nitrogen of the amine at the 1st, 3rd, and 5th positions, and are unsubstituted at other bonding positions.

7. In any one of claims 1 to 6, The light-emitting device, wherein the first benzene ring comprises a substituted or unsubstituted phenyl group.

8. In any one of claims 1 to 7, the second aromatic group is a substituted or unsubstituted fused ring skeleton having three or less rings, The number of carbon atoms forming the fused ring skeleton is 6 to 13.

9. In claim 8, The light-emitting device, wherein the fused ring skeleton is a fluorene ring.

10. In any one of claims 1 to 7, A light-emitting device wherein the second aromatic group is a dimethylfluorenyl group.

11. In any one of claims 1 to 10, A light-emitting device wherein the arylamine compound is a triarylamine compound.

12. In any one of claims 1 to 10, The light-emitting device, wherein the arylamine compound is a monoamine compound.

13. In any one of claims 1 to 12, The arylamine compound has a molecular weight of 400 or more and 1,100 or less.

14. In any one of claims 1 to 13, The light-emitting device wherein the first layer is a hole transport layer.

15. In any one of claims 1 to 13, The light-emitting device wherein the first layer is a hole injection layer.

Images