Organic compounds, light-emitting devices, electronic equipment, light-emitting devices and lighting devices

Abstract

To provide a material for hole transportation having a low refractive index.SOLUTION: A material for hole transportation contains a monoamine compound, wherein a first aromatic group, a second aromatic group and a third aromatic group are bonded to a nitrogen atom of the monoamine compound, the first aromatic group and the second aromatic group each independently have first to three benzene rings, one or both of the first aromatic group and the second aromatic group have one or a plurality of hydrocarbon groups having 1 to 12 carbon atoms in which carbon creates a bond by only sp3 hybrid orbit, the total of carbons contained in the hydrocarbon group bonded to any one of the first aromatic group and the second aromatic group is 6 or more, the total of carbons contained in all the hydrocarbon groups bonded to the first aromatic group and the second aromatic group is 8 or more, and the third aromatic group is a substituted or unsubstituted monocyclic or a substituted or unsubstituted tricyclic or lower-cyclic condensed ring.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting devices (organic EL devices) that utilize these (ence) is progressing. The basic configuration of a light-emitting device is an organic compound layer (EL layer) containing light-emitting material between a pair of electrodes. It is a device with a voltage applied to it to inject carriers, and the carriers are then re-injected. By utilizing the binding energy, it is possible to obtain light emission from a light-emitting material.

[0003] Since such light-emitting devices are self-emissive, when used as pixels in a display, they become liquid crystals. Compared to other types, it has advantages such as higher visibility and the elimination of the need for a backlight, and flat panel displays. It is suitable as an element for sprays. Also, a display using such a light-emitting device One of the major advantages of (I) is that it can be manufactured to be thin and lightweight. Furthermore, it has a very fast response speed. That is also one of its characteristics.

[0004] Furthermore, these light-emitting devices allow for the continuous formation of a light-emitting layer in two dimensions. This allows for the emission of light in a planar manner. This is different from point light sources such as incandescent bulbs and LEDs, This is a characteristic that is difficult to obtain with linear light sources such as fluorescent lamps, and therefore it is a surface light source that can be applied to lighting and the like. It also has high utility value.

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

[0006] One of the issues often raised when discussing OLED devices is light extraction. It has low efficiency. In particular, attenuation due to reflection caused by the difference in refractive index of adjacent layers is a problem. This is a major factor that reduces chair efficiency. To mitigate this effect, the EL layer is A configuration has been proposed in which a layer made of a low refractive index material is formed (see, for example, Non-Patent Document 1). .

[0007] Light-emitting devices with this configuration have higher light extraction efficiency than light-emitting devices with conventional configurations. This makes it possible to create a light-emitting device with high external quantum efficiency, but the low refractive index layer to form it inside the EL layer without adversely affecting other important properties of the light-emitting device. This is not easy. Because of the low refractive index and high carrier transport or light emission device This is because reliability when used in chairs is in a trade-off relationship. This problem is organic The carrier transportability and reliability in compound compounds largely depend on the presence of unsaturated bonds. This is because organic compounds with many saturated bonds tend to have a high refractive index. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] Japanese Patent Application Publication No. 11-282181 [Patent Document 2] Japanese Patent Publication No. 2009-91304 [Patent Document 3] U.S. Patent Application Publication No. 2010 / 104969 [Non-Patent Document 1] Jaeho Lee, et al., "Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes," Nature Communications, June 2, 2016, DOI: 10.1038 / ncomms11791 [Overview of the Initiative] [Problems that the invention aims to solve]

[0009] One aspect of the present invention aims to provide a novel material for hole transport layers. The objective is to provide a hole transport layer material with a low refractive index. In one embodiment, a material for a hole transport layer is provided that has a low refractive index and carrier transport properties. The objective is to achieve this. Alternatively, in one aspect of the present invention, a material having a low refractive index and hole transport properties is used. The objective is to provide a material for hole transport layers.

[0010] One aspect of the present invention aims to provide a novel hole injection layer material. The objective is to provide a hole injection layer material with a low refractive index. In one embodiment, a material for a hole injection layer is provided that has a low refractive index and carrier transport properties. The objective is to achieve this. Alternatively, in one aspect of the present invention, a material having a low refractive index and hole transport properties is used. The objective is to provide a material for hole injection layers.

[0011] One aspect of the present invention aims to provide a novel organic compound. In this embodiment, the objective is to provide a novel organic compound having carrier transport properties. In one aspect of the present invention, the objective is to provide a novel organic compound having hole transport properties. In one aspect of the present invention, the objective is to provide an organic compound with a low refractive index. In one aspect of the present invention, an organic compound having a low refractive index and carrier transport properties is provided. The objective is to achieve the following: Alternatively, in one aspect of the present invention, the refractive index is small and the hole transport properties are The objective is to provide organic compounds that possess these properties.

[0012] Alternatively, in one aspect of the present invention, the objective is to provide a light-emitting device with high luminescence efficiency. Alternatively, in one aspect of the present invention, a light-emitting device, light-emitting apparatus, electronic device with low power consumption, The objective is to provide a display device and a display device, respectively.

[0013] Furthermore, the description of these problems does not preclude the existence of other problems. The approach does not necessarily have to solve all of these problems. This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings It is possible to extract other issues from the descriptions in the surfaces, claims, etc.

[0014] The present invention only needs to solve one of the above-mentioned problems. [Means for solving the problem]

[0015] One aspect of the present invention is a hole transport layer material comprising an aromatic amine compound, wherein the aromatic amine The glass transition temperature of the amine compound is 90°C or higher, and the layer made of the aromatic amine compound undergoes a refractory transition. A hole transport layer material having a folding ratio of 1.5 or more and 1.75 or less. Or, one embodiment of the present invention. This is a hole transport layer material containing an aromatic amine compound, wherein the aromatic amine compound The Lath transition temperature is 90°C or higher, and the s of the total number of carbon atoms in the molecule of the aromatic amine compound is 90°C or higher. Hole vessels where the proportion of carbon atoms bonded solely through p3 hybrid orbitals is between 23% and 55%. It is a material for hole transport. Alternatively, one aspect of the present invention relates to a material for hole transport layers containing an aromatic amine compound. A material wherein the glass transition temperature of the aromatic amine compound is 90°C or higher. 1 H-NM The product of signals less than 4 ppm in the measurement of the aromatic amine compound using R. This material for hole transport layers has a fractional value that exceeds the integrated value of signals above 4 ppm.

[0016] Furthermore, the above-mentioned aromatic amine compound is preferably a triarylamine compound. Furthermore, the glass transition temperature is preferably 100°C or higher, and more preferably 11°C. The temperature is 0°C or higher, and more preferably 120°C or higher.

[0017] Furthermore, one aspect of the present invention comprises a first aromatic group, a second aromatic group, and a third aromatic group. A hole transport layer material comprising a monoamine compound, wherein the first aromatic group and the second The aromatic group and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. , a hole transport layer having a refractive index of 1.5 or more and 1.75 or less for the layer made of the monoamine compound. It is a material for use.

[0018] Alternatively, another aspect of the present invention is a first aromatic group, a second aromatic group and a third aromatic group A hole transport layer material comprising a monoamine compound having the first aromatic group, the The second aromatic group and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. The proportion of carbon atoms in the molecule that form bonds using only sp3 hybrid orbitals relative to the total number of carbon atoms is This is a hole transport layer material with a hole content of 23% to 55%.

[0019] Alternatively, another aspect of the present invention is a first aromatic group, a second aromatic group and a third aromatic group A hole transport layer material comprising a monoamine compound having the first aromatic group, the The second aromatic group and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. And, 1 The results of measuring the monoamine compound using 1H NMR showed that 4 ppm was not present. In hole transport layer materials where the integrated value of the full signal exceeds the integrated value of the signal of 4 ppm or higher. be.

[0020] Alternatively, in another aspect of the present invention, in the above configuration, the layer made of the monoamine compound This is a hole transport layer material with a refractive index of 1.5 to 1.75.

[0021] Alternatively, in another aspect of the present invention, in the above configuration, the monoamine compound is at least This is a hole transport layer material having a single fluorene skeleton.

[0022] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group, the second aromatic group A hole channel in which one or more of the fragrance group and the third aromatic group are fluorene skeletons It is a material for layer transport.

[0023] Alternatively, in another aspect of the present invention, in the above configuration, the molecular weight of the monoamine compound is 4 This is a hole transport layer material with a value between 00 and 1000.

[0024] Alternatively, another aspect of the present invention is a hole transport layer material comprising a monoamine compound, The nitrogen atom of the monoamine compound contains a first aromatic group, a second aromatic group, and a third aromatic group. Group groups are bonded, and the first aromatic group and the second aromatic group are independently Having 1 to 3 benzene rings, and one of the first aromatic group and the second aromatic group or Both are hydrocarbon groups with 1 to 12 carbon atoms, where the carbon atoms form bonds only through sp3 hybrid orbitals. It has one or more of the first aromatic group and the second aromatic group. The total number of carbon atoms in the bonded hydrocarbon group is 6 or more, and the first aromatic group And the total amount of carbon contained in all the hydrocarbon groups bonded to the second aromatic group is The number of rings is 8 or more, and the third aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted ring. This is a hole transport layer material consisting of fused rings with three or fewer substitution rings.

[0025] Alternatively, in another aspect of the present invention, in the above configuration, the ring of the third aromatic group is formed This is a hole transport layer material having 6 to 13 carbon atoms.

[0026] Alternatively, in another aspect of the present invention, in the above configuration, the layer made of the monoamine compound This is a hole transport layer material with a refractive index of 1.5 to 1.75.

[0027] Alternatively, in another aspect of the present invention, in the above configuration, the third aromatic group is fluorene bone This is a hole transport layer material with a specific grade.

[0028] Alternatively, in another aspect of the present invention, in the above configuration, the third aromatic group is fluorene bone It is a hole transport layer material of a certain grade.

[0029] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group and the second Bonding is performed using only sp3 hybrid orbitals contained in all of the hydrocarbon groups bonded to the aromatic group. This is a hole transport layer material in which the total amount of carbon produced is 36 or less.

[0030] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group and the second Bonds are formed using only sp3 hybrid orbitals present in all of the aforementioned hydrocarbon groups that are bonded to the aromatic group. This is a hole transport layer material in which the total amount of carbon is 12 or more.

[0031] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group and the second Bonding is formed using only the sp3 hybrid orbitals present in all of the aforementioned hydrocarbon groups that are bonded to the aromatic group. This is a hole transport layer material in which the total amount of carbon present is 30 or less.

[0032] Alternatively, in another aspect of the present invention, in the above configuration, carbon is bonded only by sp3 hybrid orbitals. The hydrocarbon group having 1 to 12 carbon atoms being formed is an alkyl group or carbon group having 3 to 8 carbon atoms. This material for hole transport layers is a cycloalkyl group with prime numbers between 6 and 12.

[0033] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group, the second aromatic group This material for a hole transport layer is such that both the aromatic group and the third aromatic group are hydrocarbon rings.

[0034] Alternatively, another aspect of the present invention is a first aromatic group, a second aromatic group and a third aromatic group A hole injection layer material comprising a monoamine compound having the first aromatic group, the The second aromatic group and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. The hole is formed in a layer made of the monoamine compound, and the refractive index of the layer is 1.5 or more and 1.75 or less. This is a material for injection layers.

[0035] Alternatively, another aspect of the present invention is a first aromatic group, a second aromatic group and a third aromatic group A hole injection layer material comprising a monoamine compound having the first aromatic group, the The second aromatic group and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. The proportion of carbon atoms in the molecule that form bonds using only sp3 hybrid orbitals relative to the total number of carbon atoms is This is a hole injection layer material with a hole content of 23% to 55%.

[0036] Alternatively, another aspect of the present invention is a first aromatic group, a second aromatic group and a third aromatic group A hole injection layer material comprising a monoamine compound having the first aromatic group, the The second aromatic group and the third aromatic group are bonded to the nitrogen atom of the monoamine compound. And, 1 The integral value of the signal less than 4 ppm in the results measured by H-NMR It is a hole injection layer material that exceeds the integrated value of signals above 4 ppm.

[0037] Alternatively, in another aspect of the present invention, in the above configuration, the layer made of the monoamine compound This is a hole injection layer material with a refractive index of 1.5 to 1.75.

[0038] Alternatively, in another aspect of the present invention, in the above configuration, the monoamine compound is at least This is a hole injection layer material having a single fluorene skeleton.

[0039] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group, the second aromatic group Hole injection in which one or more of the fragrance group and the third aromatic group are fluorene skeletons It is a material for layering.

[0040] Alternatively, in another aspect of the present invention, in the above configuration, the molecular weight of the monoamine compound is 4 This is a hole injection layer material with a value between 00 and 1000.

[0041] Alternatively, another aspect of the present invention is a hole injection layer material comprising a monoamine compound, The nitrogen atom of the monoamine compound contains a first aromatic group, a second aromatic group, and a third aromatic group. Group groups are bonded, and the first aromatic group and the second aromatic group are independently Having 1 to 3 benzene rings, and one of the first aromatic group and the second aromatic group or Both are hydrocarbon groups with 1 to 12 carbon atoms, where the carbon atoms form bonds only through sp3 hybrid orbitals. It has one or more of the first aromatic group and the second aromatic group. The total number of carbon atoms in the bonded hydrocarbon group is 6 or more, and the first aromatic group And the total amount of carbon contained in all the hydrocarbon groups bonded to the second aromatic group is The number of rings is 8 or more, and the third aromatic group is a substituted or unsubstituted monocyclic or substituted or unsubstituted ring. This is a hole injection layer material consisting of fused rings with three or fewer substitution rings.

[0042] Alternatively, in another aspect of the present invention, in the above configuration, the ring of the third aromatic group is formed This is a hole-injection layer material having 6 to 13 carbon atoms.

[0043] Alternatively, in another aspect of the present invention, in the above configuration, the layer made of the monoamine compound This is a hole injection layer material with a refractive index of 1.5 to 1.75.

[0044] Alternatively, in another aspect of the present invention, in the above configuration, the third aromatic group is fluorene bone This is a hole injection layer material with a specific grade.

[0045] Alternatively, in another aspect of the present invention, in the above configuration, the third aromatic group is fluorene bone This is a standard material for hole injection layers.

[0046] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group and the second Bonding is performed using only the sp3 hybrid orbitals contained in all hydrocarbon groups bonded to the aromatic group. This is a hole-injection layer material in which the total amount of carbon produced is 36 or less.

[0047] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group and the second Bonds are formed using only the sp3 hybrid orbitals present in all hydrocarbon groups bonded to the aromatic group. This is a hole-injection layer material in which the total amount of carbon is 12 or more.

[0048] Alternatively, in another aspect of the present invention, in the above configuration, the first aromatic group and the second Bonding is formed only by the sp3 hybrid orbitals present in all hydrocarbon groups that are bonded to the aromatic group. This is a hole-injection layer material in which the total amount of carbon present is 30 or less.

[0049] Alternatively, another aspect of the present invention is that, in the above configuration, carbon forms bonds only with sp3 hybrid orbitals The hydrocarbon group having 1 to 12 carbon atoms in which carbon forms bonds only with sp3 hybrid orbitals is a hole injection layer material that is an alkyl group having 3 to 8 carbon atoms or a cycloalkyl group having 6 to 12 carbon atoms.

[0050] Alternatively, another aspect of the present invention is that, in the above configuration, the first aromatic group, the second aromatic group, and the third aromatic group are all hydrocarbon rings, and it is a hole injection layer material.

[0051] In addition, in the hole transport layer material containing the above-mentioned monoamine compound and the hole injection layer material containing the monoamine compound, the glass transition point of the monoamine compound is preferably 90 °C or higher. More preferably, the glass transition point is 100 °C or higher, still more preferably 110 °C or higher, and particularly preferably 120 °C or higher.

[0052] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0053] [[ID=2,8]]

Chemical formula

[0054] However, in the above general formula (G1), Ar 1 , Ar 2 each independently represents a benzene ring or a substituent in which two or three benzene rings are bonded to each other. However, one or both of Ar 1 , Ar 2 has one or more hydrocarbon groups having 1 to 12 carbon atoms in which carbon forms bonds only with sp3 hybrid orbitals, and the hydrocarbon groups possessed by Ar and Ar 1 and Ar 2 contained in the hydrocarbon group possessed by ​​​​​The total amount of carbon is 8 or more, and Ar 1 and Ar 2 The aforementioned possessed by either one of the two The total number of carbon atoms in the hydrocarbon group is 6 or more. 1 or Ar 2 The carbonization When the hydrogen group has multiple linear alkyl groups having 1 to 2 carbon atoms, The groups may be bonded together to form a ring. Also, in the above general formula (G1), R 1 oh Call R 2 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. 1 and R 2 They are intertwined It may also be bonded to form a ring. 3 represents an alkyl group having 1 to 4 carbon atoms, u is an integer between 0 and 4.

[0055] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0056] [ka]

[0057] However, in the above general formula (G2), n, m, p, and r each independently represent 1 or 2. s, t, and u each independently represent an integer between 0 and 4. However, n+p and m+r are each Each is independently either 2 or 3. Also, R 4 and R 5 Each is independently either hydrogen or a carbon atom with 1 carbon atom. Represents any of the 3 hydrocarbon groups, R 10 ~R 14 and R 20 ~R 24 Each Independently, hydrogen or carbon atoms bond only in sp3 hybrid orbitals, with a carbon number of 1 to 12 atoms. Represents a hydrocarbon group. However, R10 ~R 14 and R 20 ~R 24 The carbons that are included in The total is 8 or more, and R 10 ~R 14 or R 20 ~R 24 Either one of the two The total number of carbon atoms included must be 6 or more. Also, R 1 , R 2 and R 3 Each is independent This represents an alkyl group having 1 to 4 carbon atoms. Note that when n is 2, it represents two phenylene groups. The type of substituent, the number of substituents, and the position of the bond may be the same or different. When m is 2, the types of substituents, the number of substituents and the bonding of the two phenylene groups The positions may be the same or different, and when p is 2, the two phenyl groups have The type of substituent, the number of substituents, and the position of the bond may be the same or different. When r is 2, the types of substituents, the number of substituents, and the bond positions of the two phenyl groups. The positions may be the same or different. Also, if s is an integer between 2 and 4, multiple R 4 They may be the same or different, and if t is an integer between 2 and 4, multiple R 5 They may be the same or different, and if u is an integer between 2 and 4, multiple R 3 These can be the same or different. 1 and R 2 They are joined together It may also form a ring, R 4 , R 5 , R 10 ~R 14 and R 20 ~R 24 is next door The groups that interact may be bonded to each other to form a ring.

[0058] Alternatively, another aspect of the present invention is an organic compound in the above configuration in which t is 0. .

[0059] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G3).

[0060] [ka]

[0061] However, in the above general formula (G3), n and p each independently represent 1 or 2, and s Each of u independently represents an integer from 0 to 4, where n+p is either 2 or 3. Also, R 10 ~R 14 and R 20 ~R 24 Each of these independently has either hydrogen or carbon in an sp3 hybrid orbital. This represents a hydrocarbon group with 1 to 12 carbon atoms that forms bonds only through pathways. However, R 10 ~R 14 and R 20 ~R 24 The total amount of carbon contained in is 8 or more, and R 10 ~R 14 or R 20 ~R 24 The total amount of carbon contained in either one of them is 6 or more. Do. Also, R 1 , R 2 and R 3 Each of these independently represents an alkyl group having 1 to 4 carbon atoms, R 4 represents hydrogen or an alkyl group having 1 to 3 carbon atoms. Note that when n is 2, two fer Even if the type, number, and position of substituents on the nylene group are the same, they may differ. It is also acceptable to have this, and if p is 2, the types and number of substituents on the two phenyl groups The positions of the linking elements may be the same or different. Also, s is an integer between 2 and 4. In the case of multiple R 4 These can be the same or different, and u is an integer between 2 and 4. In the case of multiple R 3 These can be the same or different. 1 and R 2 They are intertwined They may also be bonded to form a ring, R 4 , R 10 ~R 14 and R 20 ~R 24 teeth Adjacent groups may be bonded to each other to form a ring.

[0062] Alternatively, another aspect of the present invention is an organic compound in which s is 0 in the above configuration. .

[0063] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G4).

[0064] [ka]

[0065] However, in the above general formula (G4), u represents an integer from 0 to 4. Also, R 10 ~R 14 and R 20 ~R 24 Each of these atoms is independently connected by hydrogen or carbon in sp3 hybrid orbitals only. This represents a hydrocarbon group with 1 to 12 carbon atoms that forms a compound. However, R 10 ~R 14 and R 20 ~R 24 The total amount of carbon contained in is 8 or more, and R 10 ~R14 or R 20 to R 24 the total carbon contained in either one of them is 6 or more. Also 、R 1 _{、}R 2 and R 3 each independently represent an alkyl group having 1 to 4 carbon atoms. When u is an integer from 2 to 4, the plurality of R 3 may be the same or different from each other. Also, R 1 and R 2 may be bonded to each other to form a ring, and R 10 to R 14 and R 20 to R 24 may be such that adjacent groups are bonded to each other to form a ring.

[0066] Or, another aspect of the present invention is an organic compound in which u is 0 in the above configuration .

[0067] Or, another aspect of the present invention is an organic compound in which, in the above configuration, the R 10 to R 14 and R 20 to R 24 are each independently any one of hydrogen, a tert-butyl group, and a cyclohexyl group.

[0068] Or, another aspect of the present invention is an organic compound in which at least 3 of R 10 to R 14 、 and R 20 to R 24 are hydrogen.

[0069] Or, another aspect of the present invention is an organic compound in which, in the above configuration, R 10 、R 11 、R 13 、R 14 、 R 20 , R 21 , R 23 and R 24 is hydrogen, R 12 and R 22 is cyclohex It is an organic compound with a 'l' group.

[0070] Alternatively, in another aspect of the present invention, in the above configuration, R 10 , R 12 , R 14 , R 20 , R 21 , R 23 and R 24 is hydrogen, R 11 and R 13 is a tert-butyl group Yes, R 22 It is an organic compound in which the group is a cyclohexyl group.

[0071] Alternatively, in another aspect of the present invention, in the above configuration, R 10 , R 12 , R 14 , R 20 , R 22 and R 24 is hydrogen, R 11 , R 13 , R 21 and R 23 ga tert-bu It is an organic compound with a chill group.

[0072] Alternatively, another aspect of the present invention relates to a light-emitting device using the hole transport layer material described in any of the above descriptions. It's a vice.

[0073] Alternatively, another aspect of the present invention relates to a light-emitting device using the hole injection layer material described above. It's a vice.

[0074] Alternatively, another aspect of the present invention is a light-emitting device using the organic compound described above. That is the case.

[0075] Alternatively, another aspect of the present invention relates to the hole transport layer material, hole injection layer material and organic compound. Using one or more of the compound, the luminescent layer has a naphthobisbenzofuran skeleton or naphth This is a light-emitting device containing an organic compound having a bisbenzothiophene skeleton.

[0076] Alternatively, another aspect of the present invention is a light-emitting device as described above, and a sensor, an operating box It is an electronic device having a tongue, speaker, or microphone.

[0077] Alternatively, another aspect of the present invention is a light-emitting device as described above, and a transistor, Alternatively, it is a light-emitting device having a substrate.

[0078] Alternatively, another aspect of the present invention comprises the light-emitting device described in any of the above descriptions and a housing. It is a lighting device.

[0079] In this specification, the term "light-emitting device" includes image display devices that use light-emitting devices. Also, connectors, such as anisotropic conductive film or TCP (Tape) may be attached to the light-emitting device. Module with Carrier Package attached, print to TCP A module equipped with a wiring board, or a light-emitting device, with COG (Chip On Glas Modules with ICs (integrated circuits) directly mounted using the s) method may also be included as light-emitting devices. Furthermore, lighting fixtures and the like may have light-emitting devices. [Effects of the Invention]

[0080] In one aspect of the present invention, a novel hole transport layer material can be provided. This can provide a hole transport layer material with a low refractive index. Or, one embodiment of the present invention It is possible to provide a material for a hole transport layer having a low refractive index and carrier transport properties. Or, in one aspect of the present invention, it is possible to provide a material for a hole transport layer having a low refractive index and hole transport properties.

[0081] In one aspect of the present invention, a novel material for a hole injection layer can be provided. In one aspect of the present invention, a material for a hole injection layer having a low refractive index can be provided. Or, in one aspect of the present invention, it is possible to provide a material for a hole injection layer having a low refractive index and carrier transport properties. Or, in one aspect of the present invention, it is possible to provide a material for a hole injection layer having a low refractive index and hole transport properties.

[0082] In one aspect of the present invention, a novel organic compound can be provided. Or, in one aspect of the present invention, a novel organic compound having carrier transport properties can be provided. Or, in one aspect of the present invention, a novel organic compound having hole transport properties can be provided. In one aspect of the present invention, an organic compound having a low refractive index can be provided. Or, in one aspect of the present invention, an organic compound having a low refractive index and carrier transport properties can be provided. Or, in one aspect of the present invention, an organic compound having a low refractive index and hole transport properties can be provided.

[0083] Or, in another aspect of the present invention, a light-emitting device having high luminous efficiency can be provided. Or, in one aspect of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, and a display device each having low power consumption can be provided. <000?910>

[0084] Furthermore, the description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. Furthermore, other effects are... This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings Furthermore, it is possible to extract other effects from the descriptions in the claims and other documents. [Brief explanation of the drawing]

[0085] [Figure 1] Figures 1(A), 1(B), and 1(C) are schematic diagrams of the light-emitting device. [Figure 2] Figures 2(A) and 2(B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 3] Figures 3(A) and 3(B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 4] Figure 4 is a conceptual diagram of an active matrix type light-emitting device. [Figure 5] Figures 5(A) and 5(B) are conceptual diagrams of a passive matrix type light-emitting device. [Figure 6] Figures 6(A) and 6(B) are diagrams representing lighting devices. [Figure 7] Figures 7(A), 7(B1), 7(B2), and 7(C) are diagrams representing electronic devices. [Figure 8] Figures 8(A), 8(B), and 8(C) are diagrams representing electronic devices. [Figure 9] Figure 9 is a diagram representing a lighting device. [Figure 10] Figure 10 is a diagram representing a lighting device. [Figure 11] Figure 11 is a diagram representing an in-vehicle display device and lighting system. [Figure 12] Figures 12(A) and 12(B) are diagrams representing electronic devices. [Figure 13] Figures 13(A), 13(B), and 13(C) are diagrams representing electronic devices. [Figure 14] Figure 14 is the 1H NMR chart of dchPAF. [Figure 15] Figure 15 is the absorption spectrum and emission spectrum of dchPAF in toluene solution. [Figure 16] Figure 16 is the MS spectrum of dchPAF. [Figure 17] Figure 17 is the 1H NMR chart of chBichPAF. [Figure 18] Figure 18 is the absorption spectrum and emission spectrum of chBichPAF in toluene solution. [Figure 19] Figure 19 is the MS spectrum of chBichPAF. [Figure 20] Figure 20 is the 1H NMR chart of dchPASchF. [[ID=,20]] [Figure 21] Figure 21 is the absorption spectrum and emission spectrum of dchPASchF in toluene solution. [Figure 22] Figure 22 is the MS spectrum of dchPASchF. [Figure 23] Figure 23 is the 1H NMR chart of chBichPASchF. [Figure 24] )]]Figure 24 is the absorption spectrum and emission spectrum of chBichPASchF in toluene solution. [Figure 25] Figure 25 is the MS spectrum of chBichPASchF. [Figure 26] Figure :26 is the 1H NMR chart of SchFB1chP. [Figure 27] Figure :27 is the absorption spectrum and emission spectrum of SchFB1chP in toluene solution. [Figure 28] Figure 28 is the MS spectrum of SchFB1chP. [Figure 29] Figure 29 is the 1H NMR chart of mmtBuBichPAF. [Figure 30] Figure 30 is the absorption spectrum and emission spectrum of mmtBuBichPAF in toluene solution. [[ID=,50]] [Figure 31] Figure 31 shows the MS spectrum of mmtBuBichPAF. [Figure 32] Figure 32 shows the 1H NMR chart of dmmtBuBiAF. [Figure 33] Figure 33 shows the absorption and emission spectra of dmmtBuBiAF in a toluene solution. [Figure 34] Figure 34 shows the MS spectrum of dmmtBuBiAF. [Figure 35] Figure 35 shows the 1H NMR chart of mmtBuBimmtBuPAF. [Figure 36] Figure 36 shows the absorption and emission spectra of mmtBuBimmtBuPAF in a toluene solution. [Figure 37] Figure 37 shows the MS spectrum of mmtBuBimmtBuPAF. [Figure 38] Figure 38 shows the 1H NMR chart of dchPAPrF. [Figure 39] Figure 39 shows the absorption and emission spectra of dchPAPrF in a toluene solution. [Figure 40] Figure 40 shows the MS spectrum of dchPAPrF. [Figure 41] Figure 41 shows the 1H NMR chart of mmchBichPAF. [Figure 42] Figure 42 shows the absorption and emission spectra of mmchBichPAF in a toluene solution. [Figure 43] Figure 43 shows the MS spectrum of mmchBichPAF. [Figure 44] Figure 44 shows the 1H NMR chart of mmtBumTPchPAF. [Figure 45] Figure 45 shows the absorption and emission spectra of mmtBumTPchPAF in a toluene solution. [Figure 46] Figure 46 shows the MS spectrum of mmtBumTPchPAF. [Figure 47] Figure 47 shows the 1H NMR chart of CdoPchPAF. [Figure 48] Figure 48 shows the absorption and emission spectra of CdoPchPAF in a toluene solution. [Figure 49] Figure 49 shows the MS spectrum of CdoPchPAF. [Figure 50] Figure 50 shows the luminance-current density characteristics of light-emitting device 1-1, light-emitting device 2-1, light-emitting device 3-1, and comparative light-emitting device 1-1. [Figure 51] Figure 51 shows the current efficiency-luminance characteristics of light-emitting device 1-1, light-emitting device 2-1, light-emitting device 3-1, and comparative light-emitting device 1-1. [Figure 52] Figure 52 shows the luminance-voltage characteristics of light-emitting device 1-1, light-emitting device 2-1, light-emitting device 3-1, and comparative light-emitting device 1-1. [Figure 53] Figure 53 shows the current-voltage characteristics of light-emitting device 1-1, light-emitting device 2-1, light-emitting device 3-1, and comparative light-emitting device 1-1. [Figure 54] Figure 54 shows the external quantum efficiency-luminance characteristics of light-emitting device 1-1, light-emitting device 2-1, light-emitting device 3-1, and comparative light-emitting device 1-1. [Figure 55] Figure 55 shows the emission spectra of light-emitting device 1-1, light-emitting device 2-1, light-emitting device 3-1, and comparative light-emitting device 1-1. [Figure 56] Figure 56 shows the relationship between the chromaticity x of light-emitting devices 1-1 to 1-4, 2-1 to 2-4, 3-1 to 3-4, and comparative light-emitting devices 1-1 to 1-4 and their external quantum efficiency. [Figure 57] Figure 57 shows the change in brightness with respect to the operating time of light-emitting devices 1-1, 1-3, 2-1, 2-3, 3-1, 3-3, and comparative light-emitting devices 1-1 and 1-3. [Figure 58] Figure 58 shows the luminance-current density characteristics of light-emitting devices 4-1, 5-1, 6-1, and comparative light-emitting device 2-1. [Figure 59] Figure 59 shows the current efficiency-luminance characteristics of light-emitting devices 4-1, 5-1, 6-1, and comparative light-emitting device 2-1. [Figure 60] Figure 60 shows the luminance-voltage characteristics of light-emitting devices 4-1, 5-1, 6-1, and comparative light-emitting device 2-1. [Figure 61] Figure 61 shows the current-voltage characteristics of light-emitting devices 4-1, 5-1, 6-1, and comparative light-emitting device 2-1. [Figure 62] Figure 62 shows the external quantum efficiency-luminance characteristics of light-emitting devices 4-1, 5-1, 6-1, and comparative light-emitting device 2-1. [Figure 63] Figure 63 shows the emission spectra of light-emitting devices 4-1, 5-1, 6-1, and comparative light-emitting device 2-1. [Figure 64] Figure 64 shows the relationship between the chromaticity x of light-emitting devices 4-1 to 4-4, 5-1 to 5-4, 6-1 to 6-4, and comparative light-emitting devices 2-1 to 2-4 and their external quantum efficiency. [Figure 65] Figure 65 shows the change in brightness with respect to operating time for light-emitting devices 4-1, 4-3, 5-1, 5-3, 6-1, 6-3, and comparative light-emitting devices 2-1 and 2-3. [Figure 66] Figure 66 shows the luminance-current density characteristics of light-emitting device 7-0 and comparative light-emitting device 3-0. [Figure 67] Figure 67 shows the current efficiency-luminance characteristics of light-emitting device 7-0 and comparative light-emitting device 3-0. [Figure 68] Figure 68 shows the luminance-voltage characteristics of light-emitting device 7-0 and comparative light-emitting device 3-0. [Figure 69] Figure 69 shows the current-voltage characteristics of light-emitting device 7-0 and comparative light-emitting device 3-0. [Figure 70]Figure 70 shows the external quantum efficiency-luminance characteristics of light-emitting device 7-0 and comparative light-emitting device 3-0. [Figure 71] Figure 71 shows the emission spectra of light-emitting device 7-0 and comparative light-emitting device 3-0. [Figure 72] Figure 72 shows the relationship between BI and the chromaticity y of light-emitting devices 7-1 to 7-12 and comparative light-emitting devices 3-1 to 3-12. [Figure 73] Figure 73 shows the change in brightness of light-emitting device 7-2 and comparative light-emitting device 3-8 with respect to operating time. [Figure 74] Figure 74 shows the luminance-current density characteristics of light-emitting device 8-0 and comparative light-emitting device 3-0. [Figure 75] Figure 75 shows the current efficiency-luminance characteristics of light-emitting device 8-0 and comparative light-emitting device 3-0. [Figure 76] Figure 76 shows the luminance-voltage characteristics of light-emitting device 8-0 and comparative light-emitting device 3-0. [Figure 77] Figure 77 shows the current-voltage characteristics of light-emitting device 8-0 and comparative light-emitting device 3-0. [Figure 78] Figure 78 shows the external quantum efficiency-luminance characteristics of light-emitting device 8-0 and comparative light-emitting device 3-0. [Figure 79] Figure 79 shows the emission spectra of light-emitting device 8-0 and comparative light-emitting device 3-0. [Figure 80] Figure 80 shows the relationship between BI and the chromaticity y of light-emitting devices 8-1 to 8-12 and comparative light-emitting devices 3-1 to 3-12. [Figure 81] Figure 81 shows the change in brightness of light-emitting device 8-8 and comparative light-emitting device 3-8 with respect to operating time. [Figure 82] Figure 82 shows the measured refractive index data of the dchPAF. [Figure 83] Figure 83 shows the measured refractive index data for chBichPAF. [Figure 84]Figure 84 shows the measured refractive index data for dchPASchF. [Figure 85] Figure 85 shows the measured refractive index data for chBichPASchF. [Figure 86] Figure 86 shows the measured refractive index data for SchFB1chP. [Figure 87] Figure 87 shows the measured refractive index data for mmtBuBichPAF. [Figure 88] Figure 88 shows the measured refractive index data for dmmtBuBiAF. [Figure 89] Figure 89 shows the measured refractive index data for mmtBuBimmtBuPAF. [Figure 90] Figure 90 shows the measured refractive index data for dchPAPrF. [Figure 91] Figure 91 shows the measured refractive index data for mmchBichPAF. [Figure 92] Figure 92 shows the measured refractive index data for mmtBumTPchPAF. [Figure 93] Figure 93 shows the measured refractive index data for CdoPchPAF. [Figure 94] Figure 94 shows the refractive index data measured for dchPAF, mmtBuBichPAF, mmtBumTPchPAF, and PCBBiF. [Figure 95] Figure 95 shows the measured refractive index data for mmtBuBichPAF, mmtBumTPchPAF, and PCBBiF. [Figure 96] Figure 96 shows the luminance-current density characteristics of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4. [Figure 97] Figure 97 shows the current efficiency-luminance characteristics of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4. [Figure 98] Figure 98 shows the luminance-voltage characteristics of light-emitting device 9, light-emitting device 10, and comparison light-emitting device 4. [Figure 99] Figure 99 shows the current-voltage characteristics of light-emitting device 9, light-emitting device 10, and comparison light-emitting device 4. [Figure 100] Figure 100 shows the external quantum efficiency-luminance characteristics of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4. [Figure 101] Figure 101 shows the emission spectra of light-emitting device 9, light-emitting device 10, and comparative light-emitting device 4. [Figure 102] Figure 102 shows the current density-voltage characteristics of device 1, device 2, and device 3. [Figure 103] Figure 103 shows the electric field strength dependence of the hole mobility of the organic compound of the present invention. [Figure 104] Figures 104(A) and 104(B) are 1H NMR charts of mmtBumTPFA. [Figure 105] Figure 105 shows the absorption and emission spectra of mmtBumTPFA in a toluene solution. [Figure 106] Figure 106 shows the MS spectrum of mmtBumTPFA. [Figure 107] Figures 107(A) and 107(B) are 1H NMR charts of mmtBumTPFBi. [Figure 108] Figure 108 shows the absorption and emission spectra of mmtBumTPFBi in a toluene solution. [Figure 109] Figure 109 shows the MS spectrum of mmtBumTPFBi. [Figure 110] Figures 110(A) and 110(B) are 1H NMR charts of mmtBumTPoFBi. [Figure 111] Figure 111 shows the absorption and emission spectra of mmtBumTPoFBi in a toluene solution. [Figure 112] Figure 112 shows the MS spectrum of mmtBumTPoFBi. [Figure 113] Figures 113(A) and 113(B) are 1H NMR charts of mmtBumBichPAF. [Figure 114] Figure 114 shows the absorption and emission spectra of mmtBumBichPAF in a toluene solution. [Figure 115] Figure 115 shows the MS spectrum of mmtBumBichPAF. [Figure 116] Figures 116(A) and 116(B) are 1H NMR charts of mmtBumBioFBi. [Figure 117] Figure 117 shows the absorption and emission spectra of mmtBumBioFBi in a toluene solution. [Figure 118] Figure 118 shows the MS spectrum of mmtBumBioFBi. [Figure 119] Figures 119(A) and 119(B) are 1H NMR charts of mmtBumTPtBuPAF. [Figure 120] Figure 120 shows the absorption and emission spectra of mmtBumTPtBuPAF in a toluene solution. [Figure 121] Figure 121 shows the current efficiency-luminance characteristics of light-emitting device 11, light-emitting device 12, and comparative light-emitting device 5. [Figure 122] Figure 122 shows the external quantum efficiency-luminance characteristics of light-emitting device 11, light-emitting device 12, and comparative light-emitting device 5. [Figure 123] Figure 123 shows the emission spectra of light-emitting device 11, light-emitting device 12, and comparative light-emitting device 5. [Figure 124] Figure 124 shows the current efficiency-luminance characteristics of light-emitting device 13 and comparative light-emitting device 6. [Figure 125] Figure 125 shows the external quantum efficiency-luminance characteristics of light-emitting device 13 and comparative light-emitting device 6. [Figure 126] Figure 126 shows the emission spectra of light-emitting device 13 and comparative light-emitting device 6. [Figure 127] Figure 127 shows the measured refractive index data for mmtBumTPFA. [Figure 128] Figure 128 shows the measured refractive index data for mmtBumTPFBi. [Figure 129] Figure 129 shows the measured refractive index data for mmtBumTPoFBi. [Figure 130] Figure 130 shows the measured refractive index data for mmtBumBichPAF. [Figure 131] Figure 131 shows the measured refractive index data for mmtBumBioFBi. [Figure 132] Figure 132 shows the measured refractive index data for mmtBumTPtBuPAF. [Modes for carrying out the invention]

[0086] The embodiments of the present invention will be described in detail below with reference to the drawings. However, the present invention is as follows Not limited to the description, the form and details thereof may be described without departing from the spirit and scope of the present invention. Those skilled in the art will readily understand that the invention can be modified in various ways. Therefore, the present invention is as follows: This should not be interpreted as being limited to the contents described in the embodiments.

[0087] (Embodiment 1) Among organic compounds with carrier transport properties that can be used in organic EL elements, One of the small materials is 1,1-bis-(4-bis(4-methylphenyl)-amino -phenyl)-cyclohexane (abbreviated as TAPC) is a known example. It is a material with a low 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, by using TAPC, light-emitting devices with good external quantum efficiency can be obtained. This is what is expected.

[0088] Typically, there is a trade-off between high carrier transport and low refractive index. Carrier transport in compounds largely stems from the presence of unsaturated bonds. Organic compounds that contain a large amount of TAPC tend to have a high refractive index. TAPC is a carrier. It is a substance in which transportability and a low refractive index are in perfect balance, however on the other hand So, in compounds like TAPC that have a cyclohexane 1,1-disubstituted structure, cyclo Because two bulky substituents are inserted on one carbon atom of hexane, there is significant steric repulsion. This posed a problem in terms of reliability, as it induced instability in the molecule itself. Furthermore, TAPC's structural composition consists of cyclohexane and a simple benzene ring. Consequently, it had a low glass transition temperature (Tg) and also suffered from problems with heat resistance.

[0089] One method for obtaining a highly heat-resistant and reliable hole transport material is unsaturated carbonization. It is conceivable to introduce hydrogen groups, particularly cyclic unsaturated hydrocarbon groups, into the molecule. On the other hand, refractive index To obtain a material with low molecular refraction, it is preferable to introduce substituents with low molecular refraction into the molecule. Examples of such substituents include saturated hydrocarbon groups and cyclic saturated hydrocarbon groups.

[0090] However, these saturated hydrocarbon groups and cyclic saturated hydrocarbon groups generally have carrier transport properties. Therefore, carrier transportability and a low refractive index are basically in a trade-off relationship. In addition to possessing these features, the glass transition temperature is further improved to enhance heat resistance, and during operation Improving reliability is not easy. The inventors have overcome such trade-offs. In order to overcome this, the glass transition temperature is high, and the proportion of carbon atoms that form bonds only with sp3 hybrid orbitals is Aromatic amine compounds within a certain range were found. Furthermore, such aromatic amine compounds We found that it is useful as a material for hole transport layers or hole injection layers. In particular, Materials for hole transport layers or hole injection layers in light-emitting devices or photoelectric conversion devices We found it to be suitable as a material.

[0091] In other words, one aspect of the present invention relates to holes containing aromatic amine compounds with a glass transition temperature of 90°C or higher. A material for a transport layer and a material for a hole injection layer, wherein the layer made of the aromatic amine compound is retractable. A hole transport layer material or hole injection layer material having a folding ratio of 1.5 or more and 1.75 or less. The aromatic amine compound is bonded only by sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule. It is preferable that the proportion of carbon produced is between 23% and 55%.

[0092] Substituents composed of carbon atoms that form bonds solely through sp3 hybrid orbitals are what is known as saturated carbon dioxide. Because they are elementary groups or cyclic saturated hydrocarbon groups, their molecular refraction is low. Therefore, only sp3 hybrid orbitals are present. The carbon atoms forming the bonds account for 23% to 55% of the total number of carbon atoms in the molecule. Aromatic amine compounds are useful as materials for hole transport layers and hole injection layers with low refractive indices. It can be used.

[0093] Furthermore, the aromatic amine compound is preferably a triarylamine compound. Furthermore, the glass transition temperature is preferably 100°C or higher, and more preferably 110°C. The temperature is above ℃, and more preferably above 120℃.

[0094] Furthermore, materials used as carrier transport materials for organic EL devices have high carrier transport properties. It is preferable that the skeleton has a structure, and among these, the aromatic amine skeleton is a preferred skeleton because it has high hole transport properties. Therefore, to further improve carrier transportability, a method of introducing two amine skeletons is also being considered. It can be obtained. However, as with the TAPC mentioned above, the environment of the substituents placed around it However, the diamine structure can sometimes be detrimental to reliability.

[0095] Overcoming trade-offs, it combines carrier transportability, low refractive index, and high reliability. As a compound, the inventors have found that the proportion of carbon atoms that form bonds only with sp3 hybrid orbitals is one A monoamine compound within a specified range was found. In particular, this monoamine compound exhibits normal refraction. It has good reliability equivalent to conventional hole injection layer materials or hole transport layer materials with a high rate. It is a material that does so. Furthermore, the bonds are formed using only sp3 hybrid orbitals of the monoamine compound. Materials with better properties can be obtained by optimizing the number and substitution positions of substituents containing carbon. It can be used as a fee.

[0096] In other words, one aspect of the present invention is a first aromatic group, a second aromatic group and a third aromatic group Hole transport layer material and hole containing a monoamine compound directly bonded to the nitrogen atom of mine An injection layer material wherein the refractive index of the layer made of the monoamine compound is 1.5 or more and 1.75 The following are materials for hole transport layers and hole injection layers. The monoamine compound is The percentage of carbon atoms in the molecule that form bonds solely through sp3 hybrid orbitals is 23% or less. Preferably, it is 55% or less.

[0097] Substituents composed of carbon atoms that form bonds solely through sp3 hybrid orbitals are what is known as saturated carbon dioxide. Because they are elementary groups or cyclic saturated hydrocarbon groups, their molecular refraction is low. Therefore, only sp3 hybrid orbitals are present. The carbon atoms forming the bonds account for 23% to 55% of the total number of carbon atoms in the molecule. Noamine compounds are used as materials for hole transport layers and hole injection layers with low refractive indices. It is possible.

[0098] Furthermore, the refractive index of the layer consisting of the above aromatic amine compound or monoamine compound is determined by the amine compound. The peak wavelength of light emitted by a light-emitting device using a compound, or the compound contained in the light-emitting device. This is the refractive index at the emission peak wavelength of the light-emitting material. The peak wavelength of the light is, if a structure that adjusts the light, such as a color filter, is provided. This refers to the peak wavelength of light before it passes through the structure. Furthermore, the emission peak wavelength of the luminescent material is defined as the wavelength in solution. The relative permittivity of the organic compound constituting the EL layer of the light-emitting device is calculated using the PL spectrum. Since it is approximately 3, in order to avoid discrepancies with the emission spectrum of the light-emitting device, the light emission The relative permittivity of the solvent used to put a substance into a solution must be between 1 and 10 at room temperature. Preferably, the ratio is 2 to 5. Specifically, hexane, benzene, and Luene, diethyl ether, ethyl acetate, chloroform, chlorobenzene, dichlorometh Examples include [mention specific example]. Furthermore, it has a relative permittivity of 2 to 5 at room temperature, high solubility, and is versatile. A solvent is more preferable, for example, toluene or chloroform is preferred. The refractive index of the layer made of the above aromatic amine compound or monoamine compound is the same as the above luminescence device. If the source cannot be identified, use the wavelength in the blue emission region (455nm to 465nm). It may also be called the refractive index. Furthermore, in light of 633 nm, which is normally used to measure the refractive index, The ordinary refractive index of a layer made of an aromatic amine compound or monoamine compound according to one embodiment of the invention is The value is between 1.45 and 1.70. Note that if the material exhibits anisotropy, the value relative to ordinary light is... The refractive index and the refractive index for extraordinary light may differ. The thin film being measured may be in such a state. In this case, anisotropy analysis can be performed to separate the refractive index into ordinary and extraordinary refractive indices and analyze each refractive index. This can be calculated. In this specification, the measured material has an ordinary refractive index and an abnormality. When both refractive indices are present, the ordinary refractive index is used as the indicator.

[0099] Furthermore, the above aromatic amine compound or monoamine compound is 1 Measurements were performed using H-NMR. In the results, the integral value of signals less than 4 ppm is greater than the integral value of signals 4 ppm or greater. It is preferable that the level exceeds this. A signal of less than 4 ppm is in a chain-like or cyclic saturated hydrocarbon group. This reflects the hydrogen content, and this integral value exceeds the integral value of signals above 4 ppm. This means that the number of hydrogen atoms constituting a saturated hydrocarbon group is different from the number of hydrogen atoms constituting an unsaturated hydrocarbon group. This means that there are many more. From this, it can be seen that bonding occurs only with sp3 hybrid orbitals in the molecule. This allows us to estimate the proportion of carbon being produced. Here, the carbon in the unsaturated hydrocarbon group is more bonded to hydrogen. The number of possible bond formations is small; for example, comparing benzene and cyclohexane, C6H6 and C6 H 12 There is a difference. When this difference is taken into account, 1 4 This means that the integral value of signals below ppm is greater than the integral value of signals above 4 ppm. In other words, of the carbon atoms that make up the molecule, the carbon atoms that are part of the saturated hydrocarbon group are approximately This indicates that approximately one-third of the compound is present. As a result, the aromatic amine compound and Monoamine compounds become organic compounds with a low refractive index, and are used as materials for hole transport layers and hole injection It can be suitably used as a layering material.

[0100] Furthermore, it is preferable that the monoamine compound has at least one fluorene skeleton. i. Monoamine compounds having a fluorene skeleton exhibit good hole transport properties, and the monoamine The compound was used as either a material for the hole transport layer or a material for the hole injection layer, or both. The light-emitting device can be made into a light-emitting device with a good drive voltage. The ruolene skeleton is formed by any of the first aromatic group, the second aromatic group, and the third aromatic group. It corresponds to the fluorene skeleton being directly bonded to the nitrogen of the amine. This contributes to making the OMO level shallower, which makes it easier to pass holes, thus which is desirable. It seems so.

[0101] Furthermore, when the above monoamine compound is formed into a film by vapor deposition, its molecular weight is 400 or more. It is preferable that it be 1000 or less.

[0102] Furthermore, the monoamine compounds described above are cyclic saturated hydrocarbon groups or rigid tertiary carbides. By having an elementary group, it is possible to maintain a high Tg temperature and create a material with high heat resistance. Generally, by introducing saturated hydrocarbon groups, especially chain-type saturated hydrocarbon groups, into a certain compound, Compared to corresponding aromatic groups or heteroaromatic groups (for example, those with the same number of carbon atoms), the Tg and fusion of the compound The Tg tends to decrease. When Tg decreases, the heat resistance of the organic EL material may decrease. EL devices using organic EL materials are stable under various environments in human life. Since it is desirable to exhibit properties, if materials exhibiting equivalent properties are available, a higher Tg is preferred. It's nice.

[0103] The monoamine compounds described above will be explained in more detail below.

[0104] The monoamine compound has a first aromatic group, a second aromatic group, and a third aromatic group attached to the nitrogen atom of the amine. It is a triarylamine derivative to which three aromatic groups are bonded.

[0105] The first aromatic group and the second aromatic group each independently have 1 to 3 benzene rings. Furthermore, it is preferable that both the first and second aromatic groups are hydrocarbon groups. i. That is, the first aromatic group and the second aromatic group are a phenyl group, a biphenyl group, and tar. It is preferable that the first aromatic group and the second If one of the aromatic groups in 2 is a terphenyl group, the Tg is improved and the heat resistance is good, so this is preferred. It's nice.

[0106] When the first aromatic group and the second aromatic group each have two or three benzene rings, Preferably, the two or three benzene rings are substituents bonded to each other. Furthermore, one or both of the first aromatic group and the second aromatic group may have two or three bens. The zen rings are substituents bonded to each other, i.e., biphenyl groups or terphenyl groups. This is preferable because it improves Tg and provides good heat resistance, and the first aromatic group and the second aromatic group It is more preferable that both are independently a biphenyl group or a terphenyl group.

[0107] Furthermore, either one or both of the first and second aromatic groups have a carbon atom sp3 hybridized. It has one or more hydrocarbon groups with 1 to 12 carbon atoms that form bonds solely through orbitals. ru.

[0108] Furthermore, the above monoamine compound may consist of either the first aromatic group or the second aromatic group or Both have 1 to 12 carbon atoms, and the carbon atoms form bonds only with sp3 hybrid orbitals. Although a hydrogen group is bonded, at least one aromatic group is bonded to that aromatic group. The total number of carbon atoms in the hydrocarbon group is 6 or more. And the first aromatic group The total number of carbon atoms in all of the above hydrocarbon groups bonded to the second aromatic group is 8 or more. Preferably, it shall be 12 or more. The above hydrocarbon group with low molecular refraction is thus The bonding process results in the above monoamine compound becoming an organic compound with a low refractive index. It is possible.

[0109] Furthermore, all hydrocarbon groups bonded to the first aromatic group and the second aromatic group are included in the above hydrocarbon groups. The total amount of carbon atoms bonded solely in sp3 hybrid orbitals is necessary to maintain good carrier transportability. Preferably 36 or less, and more preferably 30 or less. As mentioned above, the carbon atoms Having more π electrons derived from unsaturated bonds is advantageous for carrier transport.

[0110] As a hydrocarbon group having 1 to 12 carbon atoms and forming bonds only with sp3 hybrid orbitals, Preferably, alkyl groups having 3 to 8 carbon atoms and cycloalkyl groups having 6 to 12 carbon atoms. Specifically, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert -Pentyl group, neopentyl group, hexyl group, isohexyl group, sec-hexyl group, t ert-hexyl group, neohexyl group, heptyl group, octyl group, cyclohexyl group, 4 -Methylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cy Clodecyl group, decahydronaphthyl group, cycloundecyl group, and cyclododecyl group, etc. In particular, tert-butyl groups, cyclohexyl groups and cyclodomethyl groups can be used. A sil group is preferred.

[0111] Furthermore, the third aromatic group may be a substituted or unsubstituted monocyclic or substituted or unsubstituted tricyclic. Assume the fused rings shown below. As the number of fused rings increases, the refractive index tends to increase. This allows the refractive index to be kept low. Similarly, as the number of fused rings increases... Because absorption and emission of light in the visible region can be observed, materials with small effects of absorption and emission are less likely to be affected. It can be used as a material. In addition, the third aromatic group has a ring in order to maintain a low refractive index. The number of carbon atoms formed is preferably 6 to 13. It is used as a third aromatic group. Examples of aromatic groups that can be used include, specifically, benzene rings, naphthalene rings, fluorene rings, and Examples include the senaphthylene ring. In particular, because it exhibits good hole transport properties, the third The aromatic group preferably contains a fluorene ring, and more preferably it contains a fluorene ring. preferable.

[0112] Monoamine compounds having the above configuration are organic compounds that possess hole transport properties and a low refractive index. Because it is a compound, it can be used as a material for the hole transport layer or hole injection layer of an organic EL device. It can be suitably used. Furthermore, the hole transport layer material or hole injection layer material can be used. Because organic EL devices have hole transport layers and hole injection layers with low refractive indices, , high luminescence efficiency, i.e., external quantum efficiency, current efficiency and blue index, It can be used as a chair. Also, the hole transport layer material or hole injection layer material can be used The EL device uses a monoamine compound as the material for the hole transport layer or the material for the hole injection layer. Yes, it limits the number of aromatic groups bonded to the saturated hydrocarbon group, thereby reducing steric repulsion. By doing so, it becomes possible to improve the stability of molecules, resulting in a luminescent device with a good lifetime. It can be used as a chair.

[0113] Furthermore, hole transport layer materials containing the above-mentioned monoamine compounds, and hole transport layer materials containing monoamine compounds In the material for the pore injection layer, the glass transition temperature of the monoamine compound is 90°C or higher. This is preferable. Furthermore, the glass transition temperature is more preferably 100°C or higher, and even more preferably The temperature is 110°C or higher, and particularly preferably 120°C or higher.

[0114] Furthermore, among the monoamine compounds mentioned above, the organic compound represented by the following general formula (G1) is particularly noteworthy. preferable.

[0115] [ka]

[0116] However, in the above general formula (G1), Ar 1 Ar 2 Each independently consists of a benzene ring, Alternatively, it represents a substituent in which two or three benzene rings are bonded to each other. Ar 1 Ar 2 year Specifically, phenyl groups, biphenyl groups, terphenyl groups, naphthylphenyl groups, etc. Phenyl can be used to lower the refractive index and maintain the carrier transport properties of nitrogen atoms. The base is particularly preferred.

[0117] Note that Ar 1 Ar 2 In one or both cases, carbon forms bonds using only sp3 hybrid orbitals. It has one or more hydrocarbon groups having 1 to 12 carbon atoms. All of these hydrocarbon groups The total amount of carbon contained is 8 or more, and Ar 1 and Ar 2 at least one of the two The total number of carbon atoms in the hydrocarbon groups possessed by the compound is 6 or more. As for hydrocarbon groups with 1 to 12 carbon atoms that form bonds only, there are aluminum groups with 3 to 8 carbon atoms. Kill groups and cycloalkyl groups having 6 to 12 carbon atoms are preferred. Specifically, propyl groups isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, Pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, neo Hexyl group, heptyl group, octyl group, cyclohexyl group, 4-methylcyclohexyl group , cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, decahydro Naphthyl groups, cycloundecyl groups, and cyclododecyl groups can be used, in particular t-butyl groups, cyclohexyl groups, and cyclododecyl groups are preferred.

[0118] Note that Ar 1 or Ar 2 The hydrocarbon group is a linear alkyl group having 1 or 2 carbon atoms. If there are multiple linear alkyl groups, they may be bonded together to form a ring.

[0119] Furthermore, in the above general formula (G1), R 1 and R 2 Each is an aluminum alloy with 1 to 4 carbon atoms. This represents the kill group. Note that R 1 and R 2 They may be bonded to each other to form a ring. Also, R 3 represents an alkyl group having 1 to 4 carbon atoms, and u is an integer from 0 to 4.

[0120] Furthermore, an organic compound according to one aspect of the present invention is shown as the following general formula (G2) to general formula (G4). It is possible.

[0121] [ka]

[0122] However, in the above general formula (G2), n, m, p, and r each independently represent 1 or 2. s, t, and u each independently represent an integer between 0 and 4. Also, n+p and m+r each Each of them is independently 2 or 3. Furthermore, s, t, and u are each 0. preferable.

[0123] In the above general formula (G2), R 1 , R 2 and R 3 Each is an aluminum alloy with 1 to 4 carbon atoms. Represents the kill group, R 4 and R 5 Each is independently a hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. It represents one of the following. Examples of hydrocarbon groups with 1 to 3 carbon atoms include methyl, ethyl, and propyl groups. Examples include the br group. As for hydrocarbon groups having 1 to 4 carbon atoms, in addition to the above, b A chill group can be cited.

[0124] Also, R 10 ~R 14 and R 20 ~R 24 Each of them independently consists of hydrogen or carbon sp This represents a hydrocarbon group with 1 to 12 carbon atoms that forms bonds using only three hybrid orbitals. As for hydrocarbon groups with 1 to 12 carbon atoms that form bonds solely through hybrid orbitals, there are groups with 3 to 12 carbon atoms. 8 alkyl groups and cycloalkyl groups having 6 to 12 carbon atoms are preferred. Specifically, Ropyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group Isopentyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, Opentyl group, hexyl group, isohexyl group, sec-hexyl group, tert-hexyl Group, neohexyl group, heptyl group, octyl group, cyclohexyl group, 4-methylcyclohexyl xyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, decyl Cahydronaphthyl groups, cycloundecyl groups, and cyclododecyl groups can be used. In particular, t-butyl groups, cyclohexyl groups, and cyclododecyl groups are preferred.

[0125] Note, R 10 ~R 14 and R 20 ~R 24 The total number of carbon atoms contained is 8 or more. Furthermore, R 10 ~R 14 or R 20 ~R 24 The total amount of carbon contained in either one of them is The value must be 6 or greater.

[0126] In the above general formula (G2), when n is 2, the types of substituents on the two phenylene groups The number of substituents and the positions of the bonds may be the same or different, and when m is 2 The types of substituents, the number of substituents, and the positions of the bonds of the two phenylene groups are the same. They may be different, and if p is 2, the types of substituents on the two phenyl groups, The number of substituents and the positions of the bonds may be the same or different, and when r is 2 The two phenyl groups have the same type of substituents, number of substituents, and bond positions. They can be different as well.

[0127] Also, if s is an integer between 2 and 4, multiple R 4 Whether they are the same or different Often, when t is an integer between 2 and 4, multiple R 5 Whether they are the same or different Often, if u is an integer between 2 and 4, multiple R 3 Whether they are the same or different Good. Also, R 1 and R 2 They may be bonded to each other to form a ring, R 4 , R 5 , R 10 ~R 14 and R 20 ~R 24 In this case, adjacent groups are bonded to each other to form a ring. You can.

[0128] [ka]

[0129] However, in the above general formula (G3), R 1 , R 2 and R 3 Each independently has 1 or more carbon atoms. R represents an alkyl group of 4. 4 This represents either hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. Examples of hydrocarbon groups having 1 to 3 carbon atoms include methyl groups, ethyl groups, and propyl groups. This is possible. In addition to the above, butyl groups can be cited as hydrocarbon groups having 1 to 4 carbon atoms. It is possible.

[0130] n and p each independently represent 1 or 2, and s and u each independently represent an integer from 0 to 4. Here, n+p is 2 or 3. It is preferable that s and u are both 0. .

[0131] Also, R 10 ~R 14 and R 20 ~R 24 Each of them independently consists of hydrogen or carbon sp This represents a hydrocarbon group with 1 to 12 carbon atoms that forms bonds using only three hybrid orbitals. As for hydrocarbon groups with 1 to 12 carbon atoms that form bonds solely through hybrid orbitals, there are groups with 3 to 12 carbon atoms. 8 alkyl groups and cycloalkyl groups having 6 to 12 carbon atoms are preferred. Specifically, Ropyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, cyclohexyl group cyclol group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, cyclo Undecyl groups and cyclododecyl groups can be used, and in particular, t-butyl groups and cyclododecyl groups can be used. Chlohexyl and cyclododecyl groups are preferred.

[0132] However, R 10 ~R 14 and R 20 ~R 24 The total amount of carbon contained is 8 or more. , and R 10 ~R 14 or R 20 ~R 24 The total amount of carbon contained in either one of them Assume that the value is 6 or greater.

[0133] Furthermore, when n is 2, the types of substituents, the number of substituents, and the bonding of the two phenylene groups are as follows: The positions of the phenyl groups may be the same or different, and when p is 2, the two phenyl groups The type of substituents, the number of substituents, and the position of the bonds may be the same or different. Also, if s is an integer between 2 and 4, multiple R4 Even though they are the same, they are different. Also, if u is an integer between 2 and 4, multiple R 3 Whether they are the same or different Good. Also, R 1 and R 2 They may be bonded to each other to form a ring, R 4 , R 10 No To R 14 and R 20 ~R 24 It is also acceptable for adjacent groups to be bonded to each other to form a ring. stomach.

[0134] [ka]

[0135] In the general formula (G4) above, u represents an integer from 0 to 4. It is preferable that u be 0. It seems so.

[0136] Also, R 10 ~R 14 and R 20 ~R 24 Each of them independently consists of hydrogen or carbon sp This represents a hydrocarbon group with 1 to 12 carbon atoms that forms bonds using only three hybrid orbitals. As for hydrocarbon groups with 1 to 12 carbon atoms that form bonds solely through hybrid orbitals, there are groups with 3 to 12 carbon atoms. 8 alkyl groups and cycloalkyl groups having 6 to 12 carbon atoms are preferred. Specifically, Ropyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group Isopentyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, Opentyl group, hexyl group, isohexyl group, sec-hexyl group, tert-hexyl Group, neohexyl group, heptyl group, octyl group, cyclohexyl group, 4-methylcyclohexyl xyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, decyl Cahydronaphthyl groups, cycloundecyl groups, and cyclododecyl groups can be used. In particular, t-butyl groups, cyclohexyl groups, and cyclododecyl groups are preferred.

[0137] However, R 10 ~R 14 and R 20 ~R 24 The total amount of carbon contained is 8 or more. , and R 10 ~R 14 or R 20 ~R 24 The total amount of carbon contained in either one of them Assume that the value is 6 or greater.

[0138] Also, R 1 , R 2 and R 3 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. If R is an integer between 2 and 4, then multiple R 3 These can be the same or different. , R 1 and R 2 They may be bonded to each other to form a ring, R 10 ~R 14 and R 20 ~R 24 In this case, adjacent groups may be bonded to each other to form a ring.

[0139] In the above general formulas (G2) to (G4), R 10 ~R 14 and R 20 ~R 24 teeth Each of these independently consists of a hydrogen atom, a tert-butyl group, and a cyclohexyl group. This is preferable because it reduces the refractive index. Also, in the above general formulas (G2) to (G4), R 10 ~R14 at least 3 and R 20 ~R 24 At least 3 of them are hydrogen. This is preferable because it does not hinder the transportability of the carrier.

[0140] Also, R 10 , R 11 , R 13 , R 14 , R 20 , R 21 , R 23 and R 24 is hydrogen Yes, R 12 and R 22 It is preferable that the group is a cyclohexyl group.

[0141] Also, R 10 , R 12 , R 14 , R 20 , R 21 , R 23 and R 24 is hydrogen, R 11 and R 13 is a tert-butyl group, R 22 The fact that it is a cyclohexyl group preferable.

[0142] Also R 10 , R 12 , R 14 , R 20 , R 22 and R 24 is hydrogen, R 11 , R 1 3 , R 21 and R 23 It is preferable that the group is a tert-butyl group.

[0143] An organic compound according to one aspect of the present invention having the above configuration has hole transport properties and a low refractive index. Since it is an organic compound, it is used as a material for hole transport layers or hole injection layers in organic EL devices. It can be suitably used as a material for hole transport layers or hole injection layers. Organic EL devices using these materials have hole transport layers and hole injection layers with low refractive indices. Therefore, the luminous efficiency, i.e., the external quantum efficiency, current efficiency and blue index, are high. It can be used as a light-emitting device. Also, the hole transport layer material or hole injection layer material Organic EL devices using this method have a hole transport layer material or hole injection layer material that is monocrystalline. Because it is a compound, it can be used to create a light-emitting device with a good lifespan.

[0144] Specific examples of organic compounds having the above configuration are shown below.

[0145] [ka]

[0146] [ka]

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[0179] [ka]

[0180] Next, we will illustrate the synthesis method of the monoamine compounds described above. This is just one example of a synthesis method used by the Ming Dynasty, and is not necessarily limited to this method.

[0181] [ka]

[0182] As shown in the synthesis scheme below, 9,9-disubstituted-9H-fluorenylamine (A) and Organic halides (X1)(X2) are combined with a metal catalyst, metal, or metal compound in the presence of a base. By coupling with certain substances, organic compounds represented by the general formula (G1) can be obtained. It is possible.

[0183] [ka]

[0184] In the above synthesis scheme, Ar 1 Ar 2 These are, independently, substitutional or non-substitutional Ben This represents a substituent consisting of a benzene ring or two or three benzene rings bonded to each other. However, Ar 1 Ar 2 One or both of these are carbon atoms that form bonds using only sp3 hybrid orbitals. Having one or more of up to 12 hydrocarbon groups, Ar 1 and Ar 2 The hydrocarbon group having The total amount of carbon contained in is 8 or more, and Ar 1 and Ar 2 either one of them possesses The total number of carbon atoms contained in the hydrocarbon group is 6 or more. 1 or Ar 2 The front When the hydrocarbon group has multiple linear alkyl groups having 1 to 2 carbon atoms, the linear alkyl group The lucyl groups may bond together to form a ring. Also, in the above general formula (G1), R 1 and R 2 Each of these independently represents an alkyl group having 1 to 4 carbon atoms. 1 and R 2 They may be bonded to each other to form a ring. Also, R 3 This represents an alkyl group having 1 to 4 carbon atoms. Furthermore, u is an integer between 0 and 4. Also, X represents a halogen element or a triflate group.

[0185] When the above synthesis reaction is carried out by the Buchwald-Hartwig reaction, X is a halogen element. Alternatively, it represents a triflate group. Preferred halogen elements are iodine, bromine, or chlorine. In this reaction, bis(dibenzylideneacetone)palladium(0) and allyl chloride palladium(0) are used. Palladium complexes or compounds such as dium dimer(II) and the tri(ter) coordinating thereto t-butyl)phosphine and di-tert-butyl(1-methyl-2,2-diphenyl) Paradipropylphosphine and tricyclohexylphosphine are paradipropylphosphine compounds containing ligands. A um catalyst is used. As a base, organic bases such as sodium tert-butoxide are used. Inorganic bases such as cesium carbonate can be used. Also, when using a solvent, En, xylene, 1,3,5-trimethylbenzene, etc. can be used. By raising the temperature above 120°C, Alley containing low-period halogen elements (e.g., chlorine) is produced. The reaction between the group and the amine proceeds quickly and in high yield, making it more preferable to have high heat resistance. Xylene or 1,3,5-trimethylbenzene will be used.

[0186] Furthermore, when the above synthesis is carried out by the Ullmann reaction, X represents a halogen element. The elements preferred are iodine, bromine, or chlorine. The catalyst is copper or a copper compound. Use the following. It is preferable to use copper(I) iodide or copper(II) acetate. Examples of such solvents include inorganic bases such as potassium carbonate. Also, the solvent is 1,3-dimethyl- 3,4,5,6-Tetrahydro-2(1H)pyrimidinone (DMPU), N-methyl-2 - Uses pyrrolidone (NMP), toluene, xylene, 1,3,5-trimethylbenzene, etc. It is possible. In the Ullmann reaction, the reaction time is shorter and higher at reaction temperatures above 100°C. Since the target product can be obtained in yield, DMPU, NMP, and 1,3,5-trimethylbe are used, which have high boiling points. It is preferable to use lenzen. Furthermore, a reaction temperature of 150°C or higher is even preferable. Therefore, a DMPU is more preferable.

[0187] As described above, organic compounds of general formula (G1) can be synthesized.

[0188] (Embodiment 2) Figure 1(A) shows a diagram representing a light-emitting device according to one aspect of the present invention. The vice has a first electrode 101, a second electrode 102, and an EL layer 103, and the EL layer The organic compound shown in Embodiment 1 is used.

[0189] The EL layer 103 has an emissive layer 113, a hole injection layer 111 and / or hole transport layer. It may also have layer 112. The light-emitting layer 113 contains a light-emitting material, which is one embodiment of the present invention. The light-emitting device obtains light from the light-emitting material. The light-emitting layer 113 contains a host material, Other materials may be included. Organic compound according to one embodiment of the present invention shown in Embodiment 1. Whether it is included in the light-emitting layer 113 or in the hole transport layer 112, the hole injection layer 1 It doesn't matter if it's included in 11, or any of them.

[0190] In addition to these, Figure 1(A) also shows an electron transport layer 114 and an electron injection layer 115. However, the configuration of light-emitting devices is not limited to these.

[0191] Because this organic compound has good hole transport properties, it is effective to use it in the hole transport layer 112. Furthermore, in one embodiment of the present invention, an organic compound is mixed with an acceptor substance. The resulting film can be used as a hole injection layer 111.

[0192] Furthermore, an organic compound according to one embodiment of the present invention can also be used as a host material. Furthermore, by co-depositing with an electron transport material, the electron transport material and the hole transport material The configuration may also be one in which an excited complex is formed by the agent. By doing so, effective energy transfer to the light-emitting material is achieved, resulting in high efficiency and a long lifespan. This makes it possible to provide light-emitting devices that possess a life of their own.

[0193] The organic compound in one aspect of the present invention is an organic compound with a low refractive index, and therefore it is placed within the EL layer By using this in the part, a light-emitting device with good external quantum efficiency can be obtained.

[0194] Next, we will describe the detailed structure and materials of the light-emitting device mentioned above. One aspect of the present invention As described above, the light-emitting device has a pair of electrodes, the first electrode 101 and the second electrode 102, between them. It has an EL layer 103 consisting of multiple layers, and in any part of the EL layer 103, The organic compound disclosed in Form 1 of the application is included.

[0195] The first electrode 101 is made of a metal, alloy, or conductive material with a large work function (specifically, 4.0 eV or more). It is preferable to form them using chemical compounds and mixtures thereof. Specifically, for example, For example, indium tin oxide (ITO), silica Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon dioxide or silicon dioxide. Examples include indium oxide (IWZO) containing tungsten oxide and zinc oxide. These conductive metal oxide films are usually deposited by sputtering, but sol-ge It is also acceptable to use methods such as the Lu method for fabrication. An example of a fabrication method is indium oxide-oxide Zinc is used in a target where 1-20 wt% zinc oxide is added to indium oxide. Methods include forming by the puttering method. Additionally, tungsten oxide and zinc oxide are used. The contained indium oxide (IWZO) has a ratio of 0.5% to tungsten oxide relative to indium oxide. Sputtering is performed using a target containing 5-5 wt% zinc oxide and 0.1-1 wt% zinc oxide. It can also be formed by law. Other materials include gold (Au), platinum (Pt), and nickel (Ni). , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Co), copper (Cu), palladium (Pd), or nitrides of metallic materials (e.g., titanium nitride) Examples include (n). Graphene can also be used. Note that the composite material described later is EL By using it in the layer that is in contact with the first electrode 101 in layer 103, regardless of the work function, It will become possible to select the polar materials.

[0196] The EL layer 103 preferably has a laminated structure, but the laminated structure is not particularly limited. There is no fixed structure, and it consists of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier block layer, and an excitation layer. Various layer structures can be applied, such as a riser block layer and a charge generation layer. Then, as shown in Figure 1(A), the hole injection layer 111, hole transport layer 112, and light-emitting layer 113 In addition, a configuration having an electron transport layer 114 and an electron injection layer 115, as shown in Figure 1(B) In addition to the hole injection layer 111, hole transport layer 112, and light emission layer 113, there is also an electron transport layer 114 Two types of configurations will be described: one having an electron injection layer 115 and a charge generation layer 116. The materials that make up each layer are described below in detail.

[0197] The hole injection layer 111 is a layer containing a substance having acceptor properties. Both organic and inorganic compounds can be used as materials.

[0198] Substances that exhibit acceptor properties include compounds containing electron-withdrawing groups (halogen groups or cyano groups). It is possible to use the substance, 7,7,8,8-tetracyano-2,3,5,6-tetrafluor Roquinodimethane (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) Examples include 10-octafluoro-7H-pyrene-2-ylidene)malononitrile. This is possible. In particular, electron-withdrawing groups can be found in condensed aromatic rings that have multiple complex atoms, such as HAT-CN. The bonded compound is preferably thermally stable. Also, electron-withdrawing groups (especially fluorogroups) are preferable. Radialene derivatives having halogen groups or cyano groups, such as [3] are very electron-accepting. It is preferable because it is high, specifically α,α',α''-1,2,3-cyclopropane Redentris [4-Cyano-2,3,5,6-Tetrafluorobenzeneacetonitrile] α,α',α''-1,2,3-cyclopropanetriylidentris[2,6-diclo [Ro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α, α',α''-1,2,3-cyclopropanetriylidentris[2,3,4,5,6- Examples include pentafluorobenzeneacetonitrile. Substances with acceptor properties. In addition to the organic compounds mentioned above, other examples include molybdenum oxide, vanadium oxide, and lutein. Nium oxides, tungsten oxides, manganese oxides, etc. can be used. In addition, Phthalocyanines such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc) The complex compound of the system, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl [Diamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylf [phenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4, Aromatic amine compounds such as 4'-diamine (abbreviation: DNTPD), or poly(3,4-) (Thilydioxythiophene) / Poly(styrene sulfonate) (PEDOT / PSS), etc. The hole injection layer 111 can also be formed using polymers or the like. The material attracts electrons from adjacent hole transport layers (or hole transport materials) by applying an electric field. It can be removed.

[0199] Furthermore, the hole injection layer 111 contains the above-mentioned acceptor substance in a material having hole transport properties. Composite materials can also be used that have been modified to include acceptor properties. By using composite materials containing certain properties, the material used to form electrodes can be selected regardless of the work function. This means that, as the first electrode 101, not only materials with a large work function, but also... This allows us to use materials with small function values.

[0200] Examples of hole-transporting materials used in composite materials include aromatic amine compounds and carbazoles. Derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.) Various organic compounds can be used. The materials are 1 x 10 -6 cm 2 It is preferable that the material has a hole mobility of / Vs or higher. It seems so. Below, we will discuss materials that can be used as hole transport materials in composite materials. List the organic compounds specifically.

[0201] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl )-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated) Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenyl Examples include carbazole derivatives such as [Duaminobenzene] (abbreviation: DPA3B). Specifically, 3-[N-(9-phenylcarbazole-3-yl)-N-phenylcarbazole-3-yl] [Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole Bazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri Su[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenylanthracene-9-yl)phenyl]-9H-carbazole (abbreviation: CzP) A) 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraph Phenylbenzene and the like can be used. As aromatic hydrocarbons, for example, 2-ter t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2 -tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3 ,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl- 9,10-Bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9, 10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylant Helical (abbreviation: DPA Anth), 2-tert-butylanthracene (abbreviation: t-BuA nth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) ), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthra Sen, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7 -Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetra Methyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10, 10'-Diphenyl-9,9'-biantryl, 10,10'-bis(2-phenylphenyl Nil)-9,9'-biantril, 10,10'-bis[(2,3,4,5,6-penta Phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene Examples include perylene and 2,5,8,11-tetra(tert-butyl)perylene. In addition, pentacene, coronene, etc. can also be used. It has a vinyl skeleton. This is also good. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2, 2-Diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2, Examples include 2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA). Furthermore, an organic compound according to one embodiment of the present invention can also be used.

[0202] Also, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl (Abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine) [Phenylamino(N'-phenylamino)phenyl(N'-phenylamino)phenyl(methacrylamide) (abbreviated) Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( High molecular weight compounds such as phenyl(benzidine) (abbreviated as Poly-TPD) can also be used. Cut.

[0203] Examples of hole-transporting materials used in composite materials include carbazole skeletons and dibenzof It must have one of the following skeletons: a ranic skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. More preferably, having substituents including a dibenzofuran ring or a dibenzothiophene ring. Aromatic amines, aromatic monoamines having a naphthalene ring, or 9-fluorenyl group It may also be an aromatic monoamine to which the nitrogen of the amine is bonded via an arylene group. These second organic compounds are substances having an N,N-bis(4-biphenyl)amino group. Having this is preferable because it allows for the creation of light-emitting devices with a good lifespan. The second organic compound is specifically 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)fer [Nyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibe Nzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (Abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-di Phenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4'' -(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB) ,4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenyl Min (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4''-(7-phenyl Naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4' -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 Lu-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβ) NαNB), 4,4'-diphenyl-4''-(5;2'-binaphthyl-1-yl)tri Phenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'- (2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyl 4-(4-biphenylyl)-4 (abbreviation: mTPBiAβNBi) '-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviated) Name: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: α NBB1BP), 4,4'-diphenyl-4''-[4'-(carbazole-9-yl) Biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4- (3-phenyl-9H-carbazole-9-yl)phenyl]tris(1,1'-bife Nyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol [Lu-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyl Riphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-cal [Bazole-3-yl)phenyl]-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'-spirobio(9H-fluorene)-4-amine (abbreviation: oFBiSF) ), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl) Dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)pheny [L]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthyl Amine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluorene -9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9- Phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-F phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenyl Min (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazo (Il-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl -4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation) :PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazo (3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naph (Tyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (Abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazo [Lu-3-yl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviated) Name: PCBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N -[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9H-fluore N-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-full Oren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-bi Su(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluid Luoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl) )-9,9'-spirobio-9H-fluorene-2-amine, N,N-bis(9,9-dimethyl Chill-9H-Fluorene-2-Il)-9,9'-Spirobi-9H-Fluorene-1-A Examples include Min, etc.

[0204] Furthermore, hole-transporting materials used in composite materials have a HOMO level of -5.7eV. It is even more preferable that the substance has a relatively deep HOMO level of -5.4 eV or lower. The hole-transporting material used in composite materials has a relatively deep HOMO level. This facilitates the injection of holes into the hole transport layer 112, and also improves the lifespan of the luminescent data. It becomes easier to obtain a vice.

[0205] Furthermore, the monoamine compound described in Embodiment 1 is also a material that has hole transport properties, It can be suitably used as a hole injection layer material for composite materials. By using the identified monoamine compound, a layer with a low refractive index is formed inside the EL layer 103. This can improve the external quantum efficiency of light-emitting devices.

[0206] Furthermore, alkali metal or alkaline earth metal fluorides are preferably mixed into the above composite material. Alternatively, by increasing the atomic ratio of fluorine atoms in the layer to 20% or more, the refraction of the layer The ratio can be reduced. This also allows a layer with a lower refractive index to form inside the EL layer 103. This can be achieved, and the external quantum efficiency of light-emitting devices can be improved.

[0207] By forming the hole injection layer 111, the hole injection performance is improved, and the driving voltage is reduced. A light-emitting device can be obtained. In addition, organic compounds with acceptability can be deposited. Because it is easy to process and readily forms thin films, it is a user-friendly material.

[0208] The hole transport layer 112 is formed by including a material that has hole transport properties. The materials are 1 x 10 -6 cm 2 It is preferable to have a hole mobility of / Vs or higher. The monoamine compound described in Embodiment 1 is a material that has hole transport properties, and hole transport It can be suitably used as a layering material. Therefore, in the embodiment, the hole transport layer 112 Preferably, the hole transport layer 112 contains the monoamine compound described in 1. It is more preferable that the compound is composed of the monoamine compound described in Embodiment 1. By including the monoamine compound described in 1 in the hole transport layer 112, within the EL layer 103 A layer with a low refractive index can be formed in the region, improving the external quantum efficiency of the light-emitting device. This becomes possible.

[0209] When using a material other than the monoamine compound described in Embodiment 1 for the hole transport layer 112, As a material having the above hole transport properties, 4,4'-bis[N-(1-naphthyl)-N-f [phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD) ), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl [Luaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorine) Len-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-( 9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4 -phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (Abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H- Carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1- Naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl- 9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9- Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl) Phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-( 9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H Chemical compounds having an aromatic amine skeleton such as -fluorene]-2-amine (abbreviated as PCBASF) Compounds, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di( N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenyl) Phenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl Compounds having a carbazole skeleton, such as ru-9H-carbazole (abbreviated as PCCP), and ,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 containing a thiophene skeleton, such as dibenzothiophene (abbreviation: DBTFLP-IV) , or 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran)( Abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9- [phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), etc. Examples include compounds having a furan skeleton. Among those mentioned above, compounds having an aromatic amine skeleton Compounds containing composites or carbazole skeletons are highly reliable and exhibit high hole transport properties. Furthermore, it is preferable because it also contributes to reducing the driving voltage. The materials listed as having hole transport properties are also materials that constitute the hole transport layer 112. It can be used suitably.

[0210] The light-emitting layer 113 has a light-emitting substance and a host material. It is acceptable for the materials to be included simultaneously. Furthermore, it is also acceptable for it to be a laminate of two layers with different compositions.

[0211] Whether the luminescent material is a fluorescent material or a phosphorescent material, it exhibits thermally activated delayed fluorescence (T The substance may be any other luminescent substance, even if it exhibits ADF (Active Deposition Factor). One embodiment is a layer that exhibits fluorescence emission, particularly a layer that exhibits blue fluorescence emission. It can be suitably applied depending on the circumstances.

[0212] In the light-emitting layer 113, possible materials that can be used as fluorescent light-emitting materials include, for example, Examples include those listed below. Other fluorescent materials can also be used.

[0213] 5,6-Bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyri Zin (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antri [Lu)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi Su(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene- 9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) ), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-di Phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazo (Abbreviated) 4'-(10-phenyl-9-anthryl)triphenylamine ( Name: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-dife Nyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl Nyl-N-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole -3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert- Butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-( 9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAP) A) N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1 -phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine]( Abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2- Anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-to Riphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N ',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene -2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9,1 0-Diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazole-3-A Min (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl] )-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N' -Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10 -Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis( 1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl) [Nyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N, 9-Triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 545 T,N,N'-diphenylquinacridone, (abbreviation: DPQd), rubren, 5,12-bi Su(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP) T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-meth Ru-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidi [-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-Tetrakis(4-methylphenyl)tetracene-5, 11-Diamine (abbreviation: p-mPhTD), 7,14-Diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]Quinolysin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitol Lu (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidine [-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6 Trahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-p Lan-4-ylidene propanedinitrile (abbreviation: BisDCJ™), N,N'-diph Phenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naph [1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3, 10-Bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamine [no]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2N) bf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-fe [nylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10F) Examples include rA2Nbf(IV)-02). In particular, 1,6FLPAPrn and 1,6 Pyridine compounds such as mMemFLPAPrn and 1,6BnfAPrn-03 Representative condensed aromatic diamine compounds have high hole-trapping properties and offer high luminescence efficiency and reliability. It is preferable because it is superior. Also, the naphthobisbenzofuran skeleton or naphthobisbenzo Organic compounds with an offen skeleton exhibit deep blue fluorescence and provide excellent blue light-emitting devices. It is preferable because it is possible. In particular, 3,10PCA2Nbf(IV)-02 and 3 , such as 10FrA2Nbf(IV)-02, which has two or more arylamine skeletons Organic compounds having a phthobisbenzofuran skeleton or a naphthobisbenzothiophene skeleton Furthermore, it is preferable because it has a high luminescence quantum yield. Naphthols to which one of the following skeletons is attached: lan skeleton, dibenzothiophene skeleton, or carbazole skeleton. Organic compounds having a bisbenzofuran skeleton or a naphthobisbenzothiophene skeleton are divided Sub-orientation increases light extraction efficiency and improves reliability (especially at high temperatures). Therefore, it is even more preferable. Furthermore, the above naphthobisbenzofuran skeleton or naphthobisbenzo Organic compounds having an offen skeleton: PL spectrum in toluene solution The microcavity is extremely narrow, less than 30 nm. Therefore, the microcavity is affected by the low refractive index layer. In one embodiment of the present invention, in which the effect is particularly effective, a light-emitting material with such a narrow half-width is used It is desirable to have them.

[0214] In the light-emitting layer 113, if a phosphorescent material is used as the light-emitting material, it is possible to use it. Examples of suitable materials include the following:

[0215] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazole-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphen) Iridium(III) (abbreviation: [Ir(Mpt) z)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-Triazolat] Iridium(III) (Abbreviation: [Ir(iPrptz-3 Organometallic iridium complexes having a 4H-triazole skeleton, such as b)3]), and Tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-tria 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]) 1H-triazole bone iridium organometallic complexes with a specific classification, and fac-tris[(1-2,6-diisopropyl [Phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), Tris[3-(2,6-dimethylphenyl)-7-methylimi Dazo[1,2-f]phenantriginato]iridium(III) (abbreviation:[Ir(dmp Organometallic iridium complexes having an imidazole skeleton such as impt-Me)3]), Bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: Fir6), bis[2-(4' ,6'-Difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolina Firpic (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl) [enyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri Dinato-N,C 2’ Iridium(III) acetylacetonate (abbreviation: Fir(ac) Organometallic compounds using phenylpyridine derivatives having electron-withdrawing groups like ac)) as ligands Examples include lydium complexes. These are compounds that exhibit blue phosphorescence, at 440 nm. This compound has an emission peak from 520 nm.

[0216] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)yli Dium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp) pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidina) Iridium(III) (Abbreviation: [Ir(tBuppm)2(ac (ac)), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylp Limiginato Iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato] Iridium(III) (Abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II) I) (abbreviation: [Ir(dppm)2(acac)]) has a pyrimidine skeleton iridium metal complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl Iridium(III) (abbreviation: Ir(mppr-Me)2(acac)) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyra) Dinato-iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) organometallic iridium complexes having a pyrazine skeleton, such as tris(2-phenylpyridium Nato-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]quinolinate) iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(be 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) acetylated Setanate (abbreviation: [Ir(pq)2(acac)]) is a pyridine skeleton-containing substance In addition to iridium metal complexes, tris(acetylacetonate)(monophenanthroline) Rare earth metals such as rubium(III) (abbreviation: [Tb(acac)3(Phen)]) Examples include complexes. These are compounds that mainly exhibit green phosphorescence, with a wavelength of 500 nm to 6 It has an emission peak at 00 nm. Furthermore, it is an organometallic iridium complex with a pyrimidine skeleton. The body is particularly preferable because it is outstanding in terms of reliability and luminescence efficiency.

[0217] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimid Sodium iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis(Ir(5mdppm)2(dibm)]), [4,6-Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridi Um(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organometallic gold with a pyrimidine skeleton, such as (abbreviation: [Ir(d1npm)2(dpm)]) Iridium complexes of the genus, and (acetylacetonato)bis(2,3,5-triphenylpyrazine Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-Triphenylpyrazinate)(dipivaloylmethanato) Iridium(III) (abbreviated) Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-Fluorophenyl)quinoxalinato] Iridium(III) (Abbreviation: [Ir(Fd Organometallic iridium complexes having a pyrazine skeleton such as pq)2(acac)]) and RIS(1-phenylisoquinolinato-N,C) 2’ Iridium(III) (abbreviation: [Ir (piq)3]), bis(1-phenylisoquinolinato-N,C 2’ Iridium (II) I) Pyridogenated acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with a n skeleton, 2, 3, 7, 8, 12, 13, 17, 18 -Octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complex and Tris(1,3-diphenyl-1,3-propanedionato)(monophenate Nanthroline europium(III) (abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monophenane) Like trolin europium(III) (abbreviation: [Eu(TTA)3(Phen)]) Examples include rare earth metal complexes. These are compounds that exhibit red phosphorescence, and 60 It has an emission peak from 0 nm to 700 nm. Furthermore, it is an organometallic compound with a pyrazine skeleton. The lydium complex yields a red emission with good chromaticity.

[0218] In addition to the phosphorescent compounds described above, other known phosphorescent substances may also be selected and used. stomach.

[0219] TADF materials include fullerenes and their derivatives, acridines and their derivatives, and eosin. Derivatives can be used. Also, magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P Examples of metal-containing porphyrins include those described in d). For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), copropol Filinetetramethyl ester-tin fluoride complex (SnF2(Copro III-4M) e) Octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiopropyl Rufirin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin - Examples include platinum chloride complexes (PtCl2OEP), etc.

[0220] [ka]

[0221] Furthermore, the following structural formula shows 2-(biphenyl-4-yl)-4,6-bis(12-) Enylindoro[2,3-a]carbazole-11-yl)-1,3,5-triazine( Abbreviations: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- Il)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT) Zn), 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl [Lu]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPT) Zn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diph Phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl -5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1, 2,4-Triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-) Cryzin-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 (abbreviated as ACRSA) Heterocyclic compounds having one or both of the π-electron-deficient heteroaromatic rings can also be used. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring. It is preferable because it has high electron transport and hole transport properties. In particular, the π-electron-deficient heteroaromatic ring is Among the skeletons it possesses, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyr The dazine skeleton and the triazine skeleton are preferred because they are stable and reliable. In particular, Benzoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, ben The zothienopyrazine skeleton is preferred because it has high acceptability and good reliability. Also, π Among skeletons having electron-excess heteroaromatic rings, the acridine skeleton, the phenoxazine skeleton, and fu The phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable. For the sake of being good, it is preferable to have at least one of the skeletons. The dibenzofuran skeleton is used for the thiophene skeleton, and the dibenzothiophene skeleton is used for the thiophene skeleton, respectively. Preferred. Also, as pyrrole skeletons, indole skeletons, carbazole skeletons, indole Carbazole skeleton, bicarbazole skeleton, 3-(9-phenyl-9H-carbazole-3) The -yl)-9H-carbazole skeleton is particularly preferred. Substances in which electron-deficient heteroaromatic rings are directly bonded to π-electron-rich heteroaromatic rings have electron-donating properties. The electron-accepting ability of the π-electron-deficient heteroatomous ring is strengthened, and the energies of the S1 and T1 levels are increased. This is particularly preferable because the difference becomes smaller, allowing for efficient acquisition of thermally activated delayed fluorescence. Instead of a π-electron-deficient heteroaromatic ring, an aromatic ring bonded to an electron-withdrawing group such as a cyano group is used. It may also be used. In addition, aromatic amine skeletons, phenazine skeletons, etc. can be used as π-electron-rich skeletons. It can be used. In addition, xanthene skeletons and thioxanthene skeletons can be used as π-electron-deficient skeletons. Dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazole skeleton, Traquinone skeleton, boron-containing skeletons such as phenylborane and volanthrene, benzonitrile and These include aromatic rings or heteroaromatic rings having nitrile or cyano groups such as cyanobenzene, and benzobenzene. Carbonyl skeletons such as phenones, phosphine oxide skeletons, sulfone skeletons, etc. can be used. In this way, at least of the π-electron-deficient heteroaromatic ring and the π-electron-excess heteroaromatic ring Instead of one, a π-electron-deficient skeleton and a π-electron-excess skeleton can be used.

[0222] [ka]

[0223] TADF materials are characterized by a small difference between the S1 and T1 levels, and triple intersystem crossing occurs due to reverse intersystem crossing. A function that can convert energy from singlet excitation energy to singlet excitation energy. It is a material that possesses this property. Therefore, the triplet excitation energy is obtained by a small amount of thermal energy. Upconversion to the multiplet excitation energy (reverse intersystem crossing) is possible, and the singlet excited state can be efficiently converted. It can be generated easily. Furthermore, the triplet excitation energy can be converted into luminescence. .

[0224] Furthermore, an excited complex (exciplex) is formed by two different substances forming an excited state. Exciplex (also called 'x' or 'exciplex') is a state where the difference between the S1 level and the T1 level is extremely small. As a TADF material capable of converting triplet excitation energy to singlet excitation energy, It has the function of being functional.

[0225] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. A cull can be used. As for TADF materials, the short-wavelength tail of its fluorescence spectrum is Draw a tangent line, and set the energy at the wavelength of the extrapolation line as the S1 level, and the short wave of the phosphorescence spectrum When a tangent line is drawn at the long side of the tail, and the energy of the wavelength of the extrapolation line is taken as the T1 level, Preferably, the difference between S1 and T1 is 0.3 eV or less, and preferably 0.2 eV or less. Even better.

[0226] Furthermore, when using TADF material as a light-emitting material, the S1 level of the host material is the TADF material. It is preferable that the T1 level of the host material is higher than the S1 level of the TADF material. A higher rank is preferable.

[0227] The host material for the light-emitting layer may be an electron-transporting material or a hole-transporting material, or the above Various carrier transport materials, such as TADF materials, can be used.

[0228] Materials with hole transport properties include those having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. A compound is preferred. For example, 4,4'-bis[N-(1-naphthyl)-N-phenyl Mino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N' -diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4, 4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino ] Biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9 -yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenyl) Nylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl Lu-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated name) :PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazo (3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl )-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation) :PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-ka Luvazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl -N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl] Fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl [9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-fluorine] Compounds having an aromatic amine skeleton such as len-2-amine (abbreviation: PCBASF), 1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)benzene Bazolyl biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H Compounds having a carbazole skeleton, such as (abbreviated as PCCP) -carbazole, and 4,4 ',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluore] [-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds containing a thiophene skeleton, such as thiophene (abbreviation: DBTFLP-IV), and 4, 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: D BF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)f [phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan bones Examples of compounds having a specific characteristic include compounds having an aromatic amine skeleton and Compounds with a rubazole skeleton are reliable, have high hole transport properties, and are drivable. It is preferable because it also contributes to voltage reduction. Furthermore, examples of materials having the above-mentioned hole transport properties can be listed below. Other organic compounds can also be used.

[0229] Examples of materials with electron transport properties include bis(10-hydroxybenzo[h]quinoli Sodium beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolate) )(4-phenylphenolate)aluminum(III) (abbreviation: BAlq), bis(8- Zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) [Phenolate]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolate zinc(II) (abbreviated as ZnBTZ) and π-electron-deficient heteroatoms Organic compounds having a fragrant ring skeleton are preferred. Organic compounds having a π-electron-deficient hetero-aromatic ring skeleton. For example, 2-(4-biphenylyl)-5-(4-tert-butylphenyl) )-1,3,4-Oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4- Phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxa [Diazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1] ,3,4-Oxadiazole-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 having a polyazole skeleton such as -II), and 2-[3-(dibenzothioff) [phenyl-4-yl]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-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxali n (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)f [enyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-diben Dia, such as zothienyl(phenyl)pyrimidine (abbreviation: 4,6mDBTP2Pm-II) Heterocyclic compounds having a din 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'-spirobio(9H-fluorene)-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"naphthol [1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3 ,5-triazine (abbreviation: mBnfBPTzn-02), and other triazine skeletons Heterocyclic compound, 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridin (Abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]be Examples include heterocyclic compounds having a pyridine skeleton, such as lenzen (abbreviated as TmPyPB). Among those mentioned above, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a triazine skeleton Compounds and heterocyclic compounds having a pyridine skeleton are reliable and preferred. In particular, dia Heterocyclic compounds with a din (pyrimidine or pyrazine) skeleton have high electron transport properties and drive electrons. It also contributes to pressure reduction.

[0230] As for TADF materials that can be used as host materials, the previously mentioned TADF materials are... The same material can be used. When TADF material is used as the host material, TA The triplet excitation energy generated in the DF material is converted to a singlet excitation energy through reverse intersystem crossing. It is converted into a substance, and then energy is transferred to the light-emitting material, thereby increasing the luminescence efficiency of the light-emitting device. This can be achieved. At this time, the TADF material functions as an energy donor, and the luminescent substance It functions as an energy acceptor.

[0231] This is very effective when the above-mentioned light-emitting material is a fluorescent material. In order to obtain high luminescence efficiency, the S1 level of the TADF material is higher than the S1 level of the fluorescent material. It is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent material. A high level is preferable. Therefore, the T1 level of the TADF material is the same as the T1 level of the fluorescent material. A higher value is preferable.

[0232] Furthermore, it exhibits emission at wavelengths that overlap with the wavelength of the lowest-energy absorption band of the fluorescent material. It is preferable to use a TADF material that exhibits fluorescence emission. This is preferable because the transfer of excitation energy to the material becomes smoother, and luminescence is obtained efficiently. stomach.

[0233] Furthermore, singlet excitation energy is efficiently generated from triplet excitation energy through reverse intersystem crossing. For this to occur, it is preferable that carrier recombination occurs in the TADF material. The triplet excitation energy generated by the DF material is transferred to the triplet excitation energy of the fluorescent material. It is preferable not to do so. To that end, the fluorescent material has a luminescent phosphodiolus ( It is preferable to have a protecting group around the skeleton that causes light emission. The protecting group is a π bond. Substituents that do not have a substituent are preferred, saturated hydrocarbons are preferred, specifically those having 3 to 10 carbon atoms. The alkyl group below, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, carbon Examples include trialkylsilyl groups with a number between 3 and 10, and it is even preferable if there are multiple protecting groups. Substituents that do not have a π bond have poor carrier transport function, therefore carrier transport and The distance between the TADF material and the fluorescent material's luminescent phosphate is minimized without affecting carrier recombination. It can keep the distance away. Here, a luminescent group is the substance that causes light emission in a fluorescent substance. This refers to an atomic group (skeleton). The luminescent group preferably has a skeleton with π bonds and contains an aromatic ring. It is preferable that it has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of compound aromatic rings include the phenanthrene skeleton, stilbene skeleton, acridone skeleton, and pheno Examples include xazine skeletons and phenothiazine skeletons. In particular, naphthalene skeletons and anthracene skeletons. Skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton It has a perylene skeleton, coumarin skeleton, quinacridone skeleton, and naphthobisbenzofuran skeleton. Fluorescent materials are preferred because they have a high fluorescence quantum yield.

[0234] When using a fluorescent material as the light-emitting material, the host material should have an anthracene skeleton. Materials that are suitable for this purpose are used as host materials for fluorescent materials. When used in this way, it is possible to realize a light-emitting layer with good luminescence efficiency and durability. Host material Substances having an anthracene skeleton that can be used as a material include diphenylanthracene skeletons, In particular, substances having a 9,10-diphenylanthracene skeleton are preferred because they are chemically stable. Furthermore, if the host material has a carbazole skeleton, hole injection and transport properties are enhanced. Therefore, it is preferable, but a benzocarbazole skeleton in which a benzene ring is further condensed on carbazole is preferable. When included, the HOMO becomes about 0.1 eV shallower than that of carbazole, making it easier for holes to enter. Therefore, it is preferable. In particular, when the host material contains a dibenzocarbazole skeleton, The HOMO becomes about 0.1 eV shallower than in zole, making it easier for holes to enter, and also for hole transport. It is also excellent in terms of properties and has high heat resistance, making it suitable. Therefore, it is even more suitable as a host material. What is interesting is the 9,10-diphenylanthracene skeleton and the carbazole skeleton (or It is a substance that simultaneously possesses a benzocarbazole skeleton or a dibenzocarbazole skeleton. From the viewpoint of hole injection and transport as described above, the carbazole skeleton was replaced with a benzofluorene skeleton. A dibenzofluorene skeleton may also be used. An example of such a substance is 9-phenyl Lu-3-[4-(10-phenyl-9-antryl)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}anthra Sen (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)fe Examples include nylanthracene (abbreviation: αN-βNPAnth). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties and are therefore preferred. That's a good choice.

[0235] Furthermore, the host material may be a mixture of multiple substances, and the mixed host material When used, a mixture of electron-transporting material and hole-transporting material is used. Preferably, by mixing an electron-transporting material with a hole-transporting material. Furthermore, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. This is possible. The weight ratio of the content of hole-transporting material to electron-transporting material is positive. The ratio of materials with pore transport properties to materials with electron transport properties should be 1:19 to 19:1.

[0236] Furthermore, phosphorescent materials can be used as part of the above-mentioned mixed materials. When using a fluorescent material as a light-emitting material, excitation energy is supplied to the fluorescent material. It can be used as an energy donor.

[0237] Furthermore, these mixed materials may form excited complexes. These excited complexes are luminescent substances. It forms an excited complex that emits light that overlaps with the wavelength of the lowest energy absorption band. By selecting the right combination, energy transfer becomes smoother, and luminescence is obtained more efficiently. This is preferable because it allows for a reduction in the drive voltage.

[0238] Furthermore, at least one of the materials forming the excitation complex may be a phosphorescent material. By doing so, the triplet excitation energy is efficiently converted to the singlet excitation energy through reverse intersystem crossing. It can be converted to -.

[0239] As a combination of materials that efficiently form excited complexes, HO is a material with hole transport properties. It is preferable that the MO level is above the HOMO level of the electron-transporting material. If the LUMO level of a material with electron-transporting properties is higher than or equal to the LUMO level of a material with electron-transporting properties Preferred. Note that the LUMO and HOMO levels of the material are controlled by cyclic voltammetry. From the electrochemical properties (reduction potential and oxidation potential) of the material measured by CV (coefficient of variation) It can be derived.

[0240] Furthermore, the formation of excited complexes is related to, for example, the emission spectrum of hole-transporting materials and electron-transporting properties. The emission spectrum of a material having the above properties, and the emission spectrum of a mixed film obtained by mixing these materials. In comparison, the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each individual material. Alternatively, this can be confirmed by observing a phenomenon (which has a new peak on the longer wavelength side). Alternatively, transient photoluminescence (PL) and electron transport of materials with hole transport properties. The transient PL of materials possessing certain properties and the transient PL of a mixed film obtained by mixing these materials are compared, and the mixing The transient PL lifetime of the film has a longer lifetime component than the transient PL lifetime of each material, or a delayed lifetime component. This can be confirmed by observing differences in transient responses, such as an increase in the proportion of the time. Furthermore, the transient PL mentioned above can be interpreted as transient electroluminescence (EL). No. That is, transient EL for hole-transporting materials, transient E for electron-transporting materials. By comparing the transient EL of L and mixed films and observing the differences in transient response, Excitation complex formation can be confirmed.

[0241] The electron transport layer 114 is a layer containing a substance that has electron transport properties. As examples, the above-mentioned materials are electron-transporting substances that can be used as host materials. You can use this.

[0242] Furthermore, the electron transport layer consists of an electron-transporting material and an alkali metal or alkaline earth metal. It is preferable that it contains elements, compounds, or complexes. Also, the electron transport layer 114 has an electric field strength [ The electron mobility at which the square root of [V / cm] is 600 is 1 × 10⁻¹⁰ -7 cm 2 / Vs or more 5×1 0 -5 cm 2 It is preferable that it is less than or equal to / Vs. Electron transport properties in electron transport layer 114 By reducing the amount of electrons injected into the light-emitting layer, the amount of electrons injected into the light-emitting layer can be controlled, and the light-emitting layer can become electron-rich. This prevents the condition from occurring. This configuration, in particular, forms the hole injection layer as a composite material. Furthermore, the HOMO level of the hole-transporting material in the composite material is -5.7 eV or higher. Materials with relatively deep HOMO levels of 5.4 eV or less tend to have a good lifetime. Therefore, it is particularly preferable. In this case, the electron-transporting material has a HOMO level of -6 It is preferable that the electron transport voltage is 0.0 eV or higher. Furthermore, the material having electron transport properties is anthracene. Preferably, it is an organic compound having a skeleton, and both an anthracene skeleton and a heterocyclic skeleton are present. It is more preferable that the compound is an organic compound. The heterocyclic skeleton is a nitrogen-containing five-membered ring skeleton. Alternatively, a nitrogen-containing six-membered ring skeleton is preferred, and these heterocyclic skeletons include pyrazole rings, imida Zole ring, oxazole ring, thiazole ring, pyrazine ring, pyrimidine ring, pyridazine ring, etc. How nitrogen-containing 5-membered ring skeletons or nitrogen-containing 6-membered ring skeletons containing two complex atoms in the ring are particularly preferred It is also used as an element, compound, or complex of alkali metals or alkaline earth metals. It is preferable that it contains an 8-hydroxyquinolinate structure. Specifically, for example, 8-Hyd Roxyquinolinato-lithium (abbreviation: Liq), 8-hydroxyquinolinato-sodium Examples include (abbreviation: Naq). In particular, monovalent metal ion complexes, especially ri A thium complex is preferred, and Liq is more preferred. Note that the 8-hydroxyquinolinate structure If it contains, use its methyl-substituted form (e.g., 2-methyl-substituted or 5-methyl-substituted form). It is also possible that alkali metals or alkaline earth metals are present in the electron transport layer. A single element, compound, or complex may have a concentration difference (including cases where it is zero) in the thickness direction. It is preferable that they be present.

[0243] Between the electron transport layer 114 and the second electrode 102, an electron injection layer 115 is provided, which is lithium fluoride. LiF (LiF), Cesium Fluoride (CsF), Calcium Fluoride (CaF2), 8-Hydrogen Alkali metals or alkaline earth metals such as xikinolinatolithium (abbreviation: Liq) A layer containing the genus or compounds thereof may be provided. The electron injection layer 115 has electron transport properties. A layer made of a substance contains alkali metals, alkaline earth metals, or compounds thereof. You may also use something like an electride. For example, calcium Examples include substances obtained by adding a high concentration of electrons to a mixed oxide of um and aluminum.

[0244] Furthermore, the electron injection layer 115 is made of a substance having electron transport properties (preferably a bipyridine skeleton). (An organic compound containing) the above alkali metal or alkaline earth metal fluoride in a microcrystalline state It is also possible to use a layer containing a concentration of 50 wt% or more. This layer is refraction Because it is a low-efficiency layer, it is possible to provide a light-emitting device with better external quantum efficiency. It becomes Noh.

[0245] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 1(B)). The charge generation layer 116 generates holes in the layer in contact with the cathode side of the layer when an electric potential is applied, and in the anode side. This refers to a layer that can inject electrons into the adjacent layer. The charge generation layer 116 has a small amount of At the very least, a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form it using the composite materials listed as materials that can be used. Also, the P-type layer 1 17 is a composite material comprising a film containing the acceptor material described above and a hole transport material It may also be constructed by stacking films containing the P-type layer 117. By applying a potential to the P-type layer 117, electrons Electrons are injected into the transport layer 114 and holes are injected into the second electrode 102, which is the cathode, and the light-emitting device It works. Furthermore, the organic compound in one aspect of the present invention is an organic compound with a low refractive index. By using it in the P-type layer 117, it is possible to obtain a light-emitting device with good external quantum efficiency. can.

[0246] In addition to the P-type layer 117, the charge generation layer 116 also includes an electron relay layer 118 and an electron injection buffer. It is preferable that one or both of the layers 119 are provided.

[0247] The electron relay layer 118 contains at least an electron-transporting material, and the electron injection buffer layer 1 It has the function of preventing interaction between 19 and the P-type layer 117, thereby enabling smooth electron transfer. The LUMO level of the electron-transporting material contained in the relay layer 118 is in the P-type layer 117. The LUMO level of the acceptor material and the charge generation layer 116 in the electron transport layer 114 It is preferable that the LUMO level is between the LUMO level of the material contained in the contacting layer. Electron relay layer 11 Specific energy levels of the LUMO level in electron-transporting materials used in 8 The voltage should be -5.0 eV or higher, preferably -5.0 eV to -3.0 eV. As for electron-transporting materials used in the electron relay layer 118, phthalocyanine-based materials are used. It is preferable to use a material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0248] The electron injection buffer layer 119 contains alkali metals, alkaline earth metals, rare earth metals, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, and carbonates) (including carbonates such as thium and cesium carbonate), alkaline earth metal compounds (oxides, halogens) Compounds of rare earth metals (including oxides, halides, and carbonates), or compounds of rare earth metals (including oxides, halides, and carbonates) It is possible to use materials with high electron injection capabilities, such as (m)).

[0249] Furthermore, the electron injection buffer layer 119 contains an electron transporting substance and a donor substance, and If performed, alkali metals, alkaline earth metals, and rare earth metals will be used as donor substances. , and these compounds (alkali metal compounds (oxides and halides such as lithium oxide) , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, (including halides and carbonates), or compounds of rare earth metals (oxides, halides, carbon In addition to salts, tetratianaphthacene (abbreviated as TTN), nickerosene, decametine Organic compounds such as runicerosene can also be used. Therefore, it is formed using the same material as the material that constitutes the electron transport layer 114 described earlier. It is possible.

[0250] The material forming the second electrode 102 has a small work function (specifically, 3.8 eV or less). (Below) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkaline materials such as lithium (Li) and cesium (Cs). Metallic compounds, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or Group 2 of the periodic table, and alloys containing these elements (MgAg, Rare earth metals such as AlLi, europium (Eu), ytterbium (Yb), and this Examples include alloys containing these. However, between the second electrode 102 and the electron transport layer, By providing an electron injection layer, regardless of the magnitude of the work function, Al, Ag, ITO, and silica can be used. Various conductive materials such as indium oxide-tin oxide containing silicon dioxide or silicon dioxide are used as the second... These conductive materials can be used as electrodes 102. It is possible to deposit films using dry methods such as the smear method, inkjet methods, spin coating methods, etc. It is possible to form it using a wet method with the sol-gel method, or by using a paste of a metal material. It may also be formed by a wet process.

[0251] Furthermore, various methods can be used to form the EL layer 103, regardless of whether they are dry or wet methods. This can be done using methods such as vacuum deposition, gravure printing, offset printing, and screen printing. You may use methods such as printing, inkjet printing, or spin coating.

[0252] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0253] The configuration of the layer provided between the first electrode 101 and the second electrode 102 is as described above. It is not limited to this. However, if the light-emitting region and the metal used in the electrodes or carrier injection layer are in close proximity To suppress the quenching that occurs as a result, the first electrode 101 and the second electrode 1 A configuration is preferred in which a light-emitting region is provided at a location away from O2 where holes and electrons recombine.

[0254] Furthermore, the hole transport layer and electron transport layer in contact with the light-emitting layer 113, and especially the recombination in the light-emitting layer 113, The carrier transport layer near the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is the light-emitting material that makes up the light-emitting layer or the light contained in the light-emitting layer. It is preferable to use materials with a band gap larger than the band gap of the material itself. It seems so.

[0255] Next, we have a light-emitting device (multilayer element, tandem element) with a configuration in which multiple light-emitting units are stacked. The form of the (also called the child) will be explained with reference to Figure 1(C). This light-emitting device is positive This is a light-emitting device having multiple light-emitting units between the electrode and the cathode. The EL layer 103 has a configuration almost identical to that shown in Figure 1(A). That is, Figure 1(C) The light-emitting device shown is a light-emitting device having multiple light-emitting units, as shown in Figure 1(A) or The light-emitting device shown in Figure 1(B) is a light-emitting device having one light-emitting unit. It can be said that.

[0256] In Figure 1(C), a first light-emitting unit 511 and a cathode 502 are located between the anode 501 and the cathode 502. A second light-emitting unit 512 is stacked with the first light-emitting unit 511 and the second light-emitting unit A charge generation layer 513 is provided between the knit 512 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in Figure 1(A), respectively. The same thing described in the explanation can be applied. Also, the first light-emitting unit 51 The first and second light-emitting units 512 may have the same configuration or different configurations.

[0257] When a voltage is applied to the anode 501 and cathode 502, the charge generation layer 513 generates a light from one of the light-emitting units. It has the function of injecting electrons into one unit and holes into the other light-emitting unit. That is, Figure In 1(C), when a voltage is applied such that the potential of the anode is higher than the potential of the cathode... In addition, the charge generation layer 513 injects electrons into the first light-emitting unit 511 and the second light-emitting unit Any method that injects a hole into T512 will suffice.

[0258] The charge generation layer 513 is formed with the same configuration as the charge generation layer 116 described in Figure 1(B). Preferably, composite materials of organic compounds and metal oxides have good carrier implantation and carrier transport properties. Due to its superior performance, it can achieve low-voltage and low-current operation. If the anode side of the net is in contact with the charge generation layer 513, the charge generation layer 513 will light up the unit. Since it can also serve as the hole injection layer of the net, the light-emitting unit does not require a hole injection layer. That's fine.

[0259] Furthermore, if an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since layer 119 plays the role of an electron injection layer in the anode-side light-emitting unit, the anode-side light emission The unit does not necessarily need to have an electron injection layer.

[0260] Figure 1(C) illustrates a light-emitting device having two light-emitting units, but there are also devices with three or more units. The same method can be applied to light-emitting devices that stack the above light-emitting units. As in the light-emitting device according to this embodiment, multiple light-emitting units are charged between a pair of electrodes. By separating and arranging the elements with the generation layer 513, high-brightness light emission is possible while maintaining a low current density. This enables the realization of even longer-lasting elements. Furthermore, it allows for low-voltage operation and low power consumption of light-emitting elements. The device can be realized.

[0261] Furthermore, by making the light-emitting color of each light-emitting unit different, the entire light-emitting device... This allows you to obtain light emission of the desired color. For example, a light emission device having two light emission units In the vise, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. By obtaining color, it is also possible to obtain a light-emitting device that emits white light as a whole. be.

[0262] Furthermore, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512 and Each layer, such as the charge generation layer, and the electrodes are, for example, deposited by methods such as vapor deposition (including vacuum deposition) and droplet ejection ( It can be formed using methods such as inkjet printing, coating, and gravure printing. They can be used. Also, they include low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and Alternatively, it may contain polymer materials.

[0263] (Embodiment 3) This embodiment describes a light-emitting device using the light-emitting device described in Embodiment 2. ru.

[0264] In this embodiment, a light-emitting device made using the light-emitting device described in Embodiment 2 is used. Let's explain using Figure 2. Figure 2(A) is a top view showing the light-emitting device, and Figure 2(B) is Figure 2(A) is a cross-sectional view taken at AB and CD. This light-emitting device is a light-emitting device The drive circuit section (source line drive circuit) 601, indicated by the dotted line, controls the emission of light. It includes a pixel section 602 and a drive circuit section (gate line drive circuit) 603. Also, 604 The sealing substrate, 605 is a sealing material, and the area inside the sealing material 605 is a space 607. It is.

[0265] The routing wire 608 is input to the source line drive circuit 601 and the gate line drive circuit 603. FPC (Flexible Printed Circuit) is a wiring system for transmitting signals and serves as an external input terminal. (Input circuit) 609 receives video signals, clock signals, start signals, reset signals, etc. Receive. Note that only the FPC is shown in the diagram here, but this FPC has a print distribution A wire substrate (PWB) may be attached. The light-emitting device in this specification is a light-emitting device This includes not only the main unit but also the state in which the FPC or PWB is attached to it. ru.

[0266] Next, the cross-sectional structure will be explained using Figure 2(B). The drive circuit section is located on the element substrate 610. And a pixel section is formed, but here, the source line drive circuit 601 which is the drive circuit section and One pixel in the pixel section 602 is shown.

[0267] The element substrate 610 is a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fiber) Made using a plastic substrate made of fluoride, polyester, or acrylic resin. Just make it.

[0268] The structure of transistors used in pixels and driving circuits is not particularly limited. For example, inverse staggered It can be a type of transistor or a staggered transistor. Also, top Either a gate-type transistor or a bottom-gate transistor is acceptable. The semiconductor material is not particularly limited, and examples include silicon, germanium, silicon carbide, nitride Gallium can be used, or an In-Ga-Zn metal oxide can be used. An oxide semiconductor containing at least one of the elements, such as zinc, gallium, and zinc, may also be used.

[0269] The crystallinity of semiconductor materials used in transistors is not particularly limited; amorphous semiconductors, Crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or semiconductors with a crystalline region in part) Any semiconductor having the properties of [the semiconductor material] may be used. If a semiconductor having crystalline properties is used, transients may occur. This is preferable because it suppresses the deterioration of the stanic characteristics.

[0270] Here, in addition to the transistors provided in the pixels and driving circuits mentioned above, the touch sensors and the like described later are also included. It is preferable to use oxide semiconductors for semiconductor devices such as transistors. It is particularly preferable to use oxide semiconductors with a wider bandgap than silicon. By using an oxide semiconductor with a wider bandgap than Ricon, the off-state of the transistor can be controlled. The current in this state can be reduced.

[0271] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). It is also In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is an oxide semiconductor containing an oxide (such as a metal like La, Ce, or Hf). It is preferable.

[0272] In particular, the semiconductor layer has multiple crystalline portions, and the c-axis of the crystalline portion is the surface on which the semiconductor layer is formed. Alternatively, an acid oriented perpendicular to the upper surface of the semiconductor layer and having no grain boundaries between adjacent crystalline regions. It is preferable to use a crystalline semiconductor film.

[0273] By using such materials as semiconductor layers, fluctuations in electrical properties are suppressed, resulting in high reliability. This makes it possible to create a transistor.

[0274] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can be used to... This makes it possible to retain the charge stored in the capacity over a long period of time. By applying a generator to each pixel, the gradation of the image displayed in each display area is maintained while driving It also becomes possible to shut down the circuit. As a result, it is possible to realize electronic devices with extremely reduced power consumption. It can be expressed.

[0275] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. The undercoat may be: Inorganic silicon oxide films, silicon nitride films, silicon oxide-nitride films, silicon nitride-oxide films, etc. It can be fabricated using an insulating film, either as a single layer or in a multilayer configuration. The underlayer is fabricated by sputtering. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, ALD ( Formed using methods such as Atomic Layer Deposition, coating, and printing. Yes, it is possible. However, a base coat does not need to be applied unless necessary.

[0276] Note that FET623 is one of the transistors formed in the drive circuit section 601. Furthermore, the drive circuit is formed using various CMOS, PMOS, or NMOS circuits. This is sufficient. Furthermore, this embodiment shows a driver-integrated type in which the drive circuit is formed on the substrate. However, this is not always necessary, and the drive circuit can be formed externally rather than on the circuit board. .

[0277] Furthermore, the pixel section 602 includes a switching FET 611 and a current control FET 612 and its drive It is formed by a plurality of pixels, each including a first electrode 613 electrically connected to the rain. However, it is not limited to this, and can also be used as a pixel unit combining three or more FETs and a capacitive element. good.

[0278] Furthermore, an insulator 614 is formed covering the end of the first electrode 613. Here, positive It can be formed by using a photosensitive acrylic resin film of a mold.

[0279] Furthermore, in order to ensure good coverage of the EL layer and other layers formed later, the upper end of the insulator 614 is Alternatively, a curved surface with curvature is formed at the lower end. For example, the material of the insulator 614 and When a positive-type photosensitive acrylic resin is used, the radius of curvature is only at the upper end of the insulator 614. It is preferable to have a curved surface having a thickness of 0.2 μm to 3 μm. Also, the insulating material 614 is used. Therefore, either a negative-type or positive-type photosensitive resin can be used.

[0280] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, the material used for the first electrode 613 which functions as an anode is a material with a work function of It is desirable to use large materials. For example, ITO film or silicon-containing indigo Indium oxide film, indium oxide film containing 2-20 wt% zinc oxide, titanium nitride film, In addition to monolayer films such as chromium films, tungsten films, zinc films, and Pt films, titanium nitride films and aluminum films are also available. Lamination with a film mainly composed of aluminum, titanium nitride film and aluminum film and titanium nitride A three-layer structure with a film can be used. Furthermore, a laminated structure can be used as a wiring resistor. It has low noise levels, provides good ohmic contact, and can even function as an anode. .

[0281] Furthermore, the EL layer 616 was coated using a vapor deposition method with a vapor deposition mask, an inkjet method, and a spin coating method. It is formed by various methods such as those described in Embodiment 2. The EL layer 616 is formed by the structure described in Embodiment 2. It contains the following: In addition, other materials constituting the EL layer 616 include low molecular weight compounds, This may be a high-molecular-weight compound (including oligomers and dendrimers).

[0282] Furthermore, the material used for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. Examples include materials with a low work function (Al, Mg, Li, Ca, or alloys and compounds thereof) It is preferable to use materials (MgAg, MgIn, AlLi, etc.). Note that the EL layer 61 If the light generated in 6 passes through the second electrode 617, the second electrode 617 is defined as the film thickness. A thin metal film and a transparent conductive film (ITO, zinc oxide containing 2-20 wt%). Using a lamination process with indium tin oxide containing zinc and silicon (zinc oxide (ZnO), etc.) That would be good.

[0283] Furthermore, the first electrode 613, the EL layer 616, and the second electrode 617 form the shape of the light-emitting device. This has been achieved. The light-emitting device is the light-emitting device described in Embodiment 2. The element is made up of multiple light-emitting devices, but in the light-emitting device of this embodiment This includes both the light-emitting device described in Embodiment 2 and light-emitting devices having other configurations. It's okay if they're mixed together.

[0284] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, A light-emitting device is placed in the space 607 surrounded by the sub-substrate 610, the sealing substrate 604, and the sealing material 605. The structure is equipped with chair 618. Furthermore, the space 607 is filled with filler material. In addition to cases where inert gases (such as nitrogen or argon) are used for filling, there are also cases where sealing materials are used for filling. There are also cases where a recess is formed in the sealing substrate and a desiccant is placed there to prevent deterioration due to moisture. This configuration is preferable because it can suppress oxidation.

[0285] Furthermore, it is preferable to use epoxy resin or glass frit for the sealing material 605. These materials should ideally be as impermeable to moisture and oxygen as possible. In addition to glass substrates and quartz substrates, other materials can be used for the encapsulating substrate 604, such as FRP (Fiber Reinforced Plastic). reinforced plastics, PVF (polyvinyl fluoride), polyester A plastic substrate made of tel or acrylic resin can be used.

[0286] Although not shown in Figure 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. It can be formed with an inorganic insulating film. Also, the exposed portion of the sealing material 605 can be covered with A protective film may be formed. Furthermore, the protective film may be on the surface and sides of the pair of substrates, a sealing layer, and an insulating layer. It can be installed to cover exposed surfaces such as the margin layer.

[0287] The protective film can be made of a material that is impermeable to impurities such as water. This effectively suppresses the diffusion of impurities such as these from the outside to the inside.

[0288] Materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers can be used, for example, aluminum oxide, hafnium oxide, etc. Phenium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide Titanium dioxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide cerium oxide, scandium oxide, erbium oxide, vanadium oxide, or indi oxide Materials containing um, etc., as well as aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, nitrogen Includes titanium dioxide, 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 oxides Strontium-containing sulfides, erbium and aluminum-containing oxides, and Materials containing oxides, etc., including lium and zirconium can be used.

[0289] The protective film can be formed using a film deposition method that provides good step coverage. This is preferable. One such method is atomic layer deposition (ALD). There is a deposition method. Protecting materials that can be formed using the ALD method. It is preferable to use it for membranes. By using the ALD method, a dense membrane can be created with cracks and pinholes. A protective film can be formed with reduced defects or with a uniform thickness. Also, This reduces the damage inflicted on the processed material when forming a protective film.

[0290] For example, by forming a protective film using the ALD method, surfaces with complex uneven shapes, or taps can be formed. A uniform and low-defect protective film can be formed on the top, sides, and back surfaces of the panel. .

[0291] As described above, a light-emitting device fabricated using the light-emitting device described in Embodiment 2 is obtained. It is possible.

[0292] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2. This makes it possible to obtain a light-emitting device with good characteristics. Specifically, the method described in Embodiment 2. Because light-emitting devices have good luminous efficiency, it is possible to create light-emitting devices with low power consumption. ru.

[0293] Figure 3 shows a light-emitting device that emits white light, with a colored layer (color filter) provided. This shows an example of a light-emitting device that has been made full-color. Figure 3(A) shows substrate 1001, base Insulating film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, Interlayer insulating film 1020, second interlayer insulating film 1021, peripheral portion 1042, pixel portion 1040 , drive circuit section 1041, first electrodes 1024W, 1024R, 1024G of the light-emitting device , 1024B, partition wall 1025, EL layer 1028, second electrode 1029 of light-emitting device, seal The stopper plate 1031, sealing material 1032, etc. are shown in the diagram.

[0294] Furthermore, Figure 3(A) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue). The colored layer 1034B is provided on a transparent substrate 1033. Also, the black matrix 1 A 035 layer may be further provided. Transparent substrate 1 provided with a colored layer and a black matrix. 033 is aligned and fixed to substrate 1001. Note that the colored layer and black matrix Kus 1035 is covered with an overcoat layer 1036. Also, in Figure 3(A) This consists of a light-emitting layer that allows light to escape to the outside without passing through the colored layers, and a layer that allows light to escape to the outside by passing through the colored layers of each color. There is a light-emitting layer, and light that does not pass through the colored layer is white, while light that passes through the colored layer is red, green, and blue. Therefore, images can be represented using four colored pixels.

[0295] Figure 3(B) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer Example of forming layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. This was shown. Thus, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's good too.

[0296] Furthermore, in the light-emitting device described above, light is taken to the substrate 1001 side on which the FET is formed. Although a light-emitting device with a bottom-emission structure was used, the light emission was taken from the sealing substrate 1031 side. It can also be used as a light-emitting device with a projection structure (top emission type). A cross-sectional view of the light-emitting device is shown in Figure 4. In this case, the substrate 1001 is a substrate that does not transmit light. This can be done. Until the connecting electrode that connects the FET and the anode of the light-emitting device is fabricated, the bottle It is formed in the same way as a muemission-type light-emitting device. Then, the third interlayer insulating film 1037 is electrically... It is formed covering pole 1022. This insulating film may also play a planarization role. Third layer The interlayer insulating film 1037 is formed using the same material as the second interlayer insulating film, as well as other known materials. It is possible.

[0297] The first electrodes of the light-emitting device, 1024W, 1024R, 1024G, and 1024B, are located here. It is designated as the anode, but it can also be the cathode. Also, a top-emission type generator as shown in Figure 4. In the case of an optical device, it is preferable that the first electrode be a reflective electrode. Configuration of EL layer 1028 The configuration is as described in Embodiment 2 as the EL layer 103, and the white light The device structure is designed to allow light to be obtained.

[0298] In the top emission structure shown in Figure 4, the colored layer (red colored layer 1034R, green colored layer) The sealing is performed using a sealing substrate 1031 having a color layer 1034G and a blue colored layer 1034B. This can be done. The encapsulation substrate 1031 has a black matrix positioned between the pixels. 1035 may be provided. Colored layer (red colored layer 1034R, green colored layer 1034G, The blue colored layer (1034B) and the black matrix are formed by the overcoat layer (1036). It may be covered. The sealing substrate 1031 shall be a light-transmitting substrate. Furthermore, while we have shown an example of full-color display using four colors—red, green, blue, and white—this is not particularly limited. Alternatively, full-color display may be performed using four colors: red, yellow, green, and blue, or three colors: red, green, and blue.

[0299] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure has a first electrode as a reflective electrode and a second electrode as This is obtained by using semi-transparent and semi-reflective electrodes. Between the reflective electrode and the semi-transparent and semi-reflective electrode It has at least an EL layer and at least an emissive layer that forms an emissive region.

[0300] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%. It is %, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ωcm in diameter. Also, semipermeable... The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1 × 10 -2 Assume the membrane is less than Ωcm in diameter.

[0301] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transmitting / semi-reflective electrode. It is reflected and resonates.

[0302] The light-emitting device changes the thickness of the transparent conductive film, the aforementioned composite material, the carrier transport material, etc. This allows us to change the optical distance between the reflective electrode and the semitransmissive / semi-reflective electrode. Furthermore, the light of the resonant wavelength is amplified between the reflective electrode and the semitransmissive / semi-reflective electrode, causing resonance. It can attenuate light of wavelengths that are not present.

[0303] Furthermore, the light reflected back by the reflective electrode (the first reflected light) is semi-transmitted from the light-emitting layer. • Because it causes significant interference with the light (first incident light) that directly enters the semi-reflecting electrode, the reflective electrode and The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is amplified). It is preferable to adjust the wavelength of the emitted light. By adjusting the optical distance, the first By aligning the phase of the reflected light and the first incident light, the light emitted from the light-emitting layer can be further amplified. ru.

[0304] Furthermore, even if the EL layer in the above configuration has a structure with multiple light-emitting layers, it may still be a single light-emitting layer The structure may also have the following characteristics, for example, in combination with the configuration of the tandem light-emitting device described above. Furthermore, multiple EL layers are provided in a single light-emitting device with a charge generation layer in between, and each EL layer This may also be applied to a configuration in which one or more light-emitting layers are formed.

[0305] Having a microcavity structure enhances the emission intensity in the front direction at specific wavelengths. This makes it possible to reduce power consumption. Furthermore, the four sub-colors red, yellow, green, and blue are used. In the case of a light-emitting device that displays images as is, in addition to the brightness enhancement effect of yellow light emission, all sub-pixels By applying a microcavity structure tailored to the wavelength of each color, a light-emitting device with excellent characteristics can be produced. It can be placed there.

[0306] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2. This makes it possible to obtain a light-emitting device with good characteristics. Specifically, the method described in Embodiment 2. Because light-emitting devices have good luminous efficiency, it is possible to create light-emitting devices with low power consumption. ru.

[0307] Up to this point, we have explained active-matrix light-emitting devices, but from here on we will discuss passive devices. A matrix-type light-emitting device will be described. Figure 5 shows a passive light-emitting device fabricated by applying the present invention. This shows a matrix-type light-emitting device. Note that Figure 5(A) is a perspective view showing the light-emitting device, Figure 5( B) is a cross-sectional view obtained by cutting Figure 5(A) along the XY line. In Figure 5, on the substrate 951, An EL layer 955 is provided between electrode 952 and electrode 956. The end of electrode 952 is It is covered with an insulating layer 953. And a partition layer 954 is provided on top of the insulating layer 953. The side walls of the partition layer 954, as they approach the substrate surface, have a gap between one side wall and the other side wall. It has a slope that narrows as the partition becomes narrower. In other words, the cross-section of the partition wall layer 954 in the short-side direction is It is a shape, and the bottom edge (which faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) ) is the upper edge (the edge that faces the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). It is shorter than that. In this way, by providing the partition layer 954, light emission devices caused by static electricity, etc. This can prevent defects in the system. Furthermore, it can also be implemented in passive matrix type light-emitting devices. It uses the light-emitting device described in Form 2, and is a reliable light-emitting device, or has low power consumption. It can be made into a small light-emitting device.

[0308] The light-emitting device described above consists of numerous tiny light-emitting devices arranged in a matrix. Because these can be controlled, it can be suitably used as a display device for representing images. It is a light-emitting device.

[0309] Furthermore, this embodiment can be freely combined with other embodiments.

[0310] (Embodiment 4) In this embodiment, Figure 6 shows an example in which the light-emitting device described in Embodiment 2 is used as an illumination device. I will explain while referring to Figure 6(B). Figure 6(B) is a top view of the lighting device, and Figure 6(A) is a top view of Figure 6(B). This is a cross-sectional view.

[0311] The lighting device in this embodiment has a light-transmitting substrate 400 which is a support, and a first An electrode 401 is formed. The first electrode 401 is the first electrode 10 in Embodiment 1. This corresponds to 1. When light is extracted from the first electrode 401 side, the first electrode 401 is light-transmitting. It is formed from a material having [a certain characteristic].

[0312] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0313] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is in Embodiment 1 The configuration of the EL layer 103 in the light-emitting units 511, 512 and the charge generation layer 513 This corresponds to a combined configuration, etc. Please refer to the relevant description for details on these configurations.

[0314] The EL layer 403 is covered to form the second electrode 404. The second electrode 404 is in Embodiment 1. This corresponds to the second electrode 102. When light emission is taken from the first electrode 401 side, the second The electrode 404 is formed of a highly reflective material. The second electrode 404 is pad 412 Voltage is supplied by connecting it to it.

[0315] The above describes a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. The lighting device shown in this embodiment has a light-emitting device with high luminous efficiency. Since it is a chair, the lighting device in this embodiment is a lighting device with low power consumption. It is possible.

[0316] The substrate 400 on which the light-emitting device having the above configuration is formed and the sealing substrate 407 are sealed The lighting device is completed by fixing and sealing it using materials 405 and 406. Either 405 or 406 is acceptable. Also, the inner sealing material 406 (Figure 6 (B) (Not shown) A desiccant can also be mixed in, which allows it to absorb moisture. This leads to improved reliability.

[0317] Furthermore, the pad 412 and a portion of the first electrode 401 are extended outside the sealing materials 405 and 406. By providing it, it can be used as an external input terminal. Also, a converter can be placed on top of it. An IC chip 420 or similar, which incorporates such features, may also be provided.

[0318] As described above, the lighting device described in this embodiment has an EL element and the light-emitting device described in Embodiment 2. This allows for a light-emitting device with low power consumption.

[0319] (Embodiment 5) In this embodiment, an example of an electronic device that includes the light-emitting device described in Embodiment 2 as a part thereof is provided. This will be explained. The light-emitting device described in Embodiment 2 has good luminous efficiency and low power consumption. It is a small light-emitting device. As a result, the electronic device described in this embodiment has low power consumption. It is possible to create an electronic device that has a small light-emitting part.

[0320] Examples of electronic devices to which the above-mentioned light-emitting device is applied include television equipment (televisions, and (Also called a television receiver), monitors for computers, digital cameras, digital cameras Digital video cameras, digital photo frames, mobile phones (both mobile phones and mobile phone devices) (Examples include) portable game consoles, personal digital assistants, audio playback devices, and large game machines such as pachinko machines. These are some examples. Specific examples of these electronic devices are shown below.

[0321] Figure 7(A) shows an example of a television system. The television system is housed in a 710 enclosure. The display unit 7103 is incorporated into part 1. Also, the housing is connected by the stand 7105. This shows the configuration supporting 7101. The display unit 7103 can display video. The display unit 7103 is capable of arranging the light-emitting devices described in Embodiment 2 in a matrix. It is composed of the following.

[0322] The television equipment can be operated using the control switches on the housing 7101 or a separate remote control. This can be done using the device 7110. The remote control device 7110 has an operation key 7109. This allows you to control the channel and volume, and the video displayed on the display unit 7103 It can be operated. Also, the remote control unit 7110 A display unit 7107 that displays the information output from the unit may also be provided.

[0323] The television system shall consist of a receiver, modem, etc. It can receive television broadcasts, and also communicate via wired or wireless connection through a modem. By connecting to a network, one-way (sender to receiver) or two-way (sender to receiver) communication is possible. It is also possible to communicate information between recipients, or between recipients themselves.

[0324] Figure 7(B1) is a computer, consisting of the main unit 7201, the casing 7202, the display unit 7203, and a key - Includes board 7204, external connection port 7205, pointing device 7206, etc. Furthermore, this computer arranges the light-emitting devices described in Embodiment 2 in a matrix. It is manufactured by using it in the display unit 7203. The computer in Figure 7(B1) is It may also be in a form like 7(B2). The computer in Figure 7(B2) has a keyboard 7 204, a second display unit 7210 is provided instead of the pointing device 7206. The second display unit 7210 is a touch panel, and the second display unit 7210 displays Input can be performed by operating the displayed input indicator with your finger or a special pen. Furthermore, the second display unit 7210 can display not only input information but also other images. It is possible. The display unit 7203 may also be a touch panel. The two screens are hinged. Because it is connected, the screen may be scratched or damaged when stored or transported. This can also prevent problems from occurring.

[0325] Figure 7(C) shows an example of a mobile terminal. The mobile phone is incorporated into the housing 7401. In addition to the display unit 7402, there are operation buttons 7403, an external connection port 7404, and a speaker 740 5. It is equipped with a microphone 7406, etc. The mobile phone is the light-emitting device described in Embodiment 2. It has a display unit 7402 made by arranging devices in a matrix.

[0326] The mobile terminal shown in Figure 7(C) allows users to input information by touching the display unit 7402 with their fingers or other objects. It can also be configured to allow for making phone calls or composing emails. Operations such as this can be performed by touching the display unit 7402 with a finger or the like.

[0327] The display unit 7402 has three main modes. The first is a display that primarily displays images. The first mode is display mode, the second is input mode which is mainly for inputting information such as characters. The third is display mode. This is a display + input mode, which is a combination of two modes: display mode and input mode.

[0328] For example, when making a phone call or composing an email, the display unit 7402 is used for text input. In this case, the primary text input mode should be used, and you should perform the input operation for the characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402. It seems so.

[0329] Furthermore, the mobile device has sensors inside that detect tilt, such as a gyroscope and an accelerometer. By installing the device, the orientation of the mobile terminal (portrait or landscape) is determined, and the screen display of the display unit 7402 is displayed accordingly. The display can be set to switch automatically.

[0330] Furthermore, screen modes can be switched by touching the display unit 7402 or by operating the housing 7401. This is done by operating button 7403. Also, the type of image displayed on display unit 7402 Therefore, it is also possible to switch between them. For example, the image signal displayed on the display unit is a video signal. Switch to display mode if it's data, or to input mode if it's text data.

[0331] Furthermore, in input mode, the signal detected by the optical sensor of the display unit 7402 is detected and displayed If there is no input via touch operation on unit 7402 for a certain period of time, the screen mode will be changed to input mode. You may also control the system to switch from that display mode to a different mode.

[0332] The display unit 7402 can also function as an image sensor. For example, the display unit 74 By touching device 02 with the palm or fingers, the user can be authenticated by capturing images of their palm print, fingerprints, etc. Furthermore, the display unit may have a backlight that emits near-infrared light or a sensing light that emits near-infrared light. Using the appropriate source, it is also possible to image finger veins, palmar veins, and other veins.

[0333] The configuration shown in this embodiment is a combination of the configurations shown in Embodiments 1 to 4 as appropriate. They can be used together.

[0334] As described above, the application range of the light-emitting device equipped with the light-emitting device described in Embodiment 2 is extremely broad. This light-emitting device can be applied to electronic devices in all fields. Embodiment 2 By using the described light-emitting device, it is possible to obtain electronic devices with low power consumption.

[0335] Figure 8(A) is a schematic diagram showing an example of a cleaning robot.

[0336] The cleaning robot 5100 has a display 5101 located on the top and multiple displays located on the sides. It has several cameras 5102, brushes 5103, and operation buttons 5104. However, the underside of the 5100 cleaning robot is equipped with wheels, a suction port, etc. The 5100 robot also includes an infrared sensor, ultrasonic sensor, acceleration sensor, and piezo sensor. It is equipped with various sensors such as optical sensors and gyro sensors. Also, the cleaning robot 5 Unit 100 is equipped with wireless communication means.

[0337] The cleaning robot 5100 moves autonomously, detects the dirt 5120, and uses the suction port located on its underside to... It can then vacuum up the dust.

[0338] Furthermore, the cleaning robot 5100 analyzes images captured by the camera 5102, and detects walls, furniture, or It can determine the presence or absence of obstacles such as steps. Furthermore, image analysis can detect wiring and other obstacles. If an object that may become entangled in brush 5103 is detected, the rotation of brush 5103 will be stopped. can.

[0339] The display 5101 displays information such as the battery level and the amount of dust collected. This is possible. The path taken by the cleaning robot 5100 can be displayed on the display 5101. Good. Also, the display 5101 is a touch panel, and the operation buttons 5104 are on the display. It may also be provided at Ray 5101.

[0340] The cleaning robot 5100 can communicate with portable electronic devices 5140 such as smartphones. Yes, it is possible. Images captured by camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the 5100 cleaning robot can know what's happening in the room even when they're away from home. It is possible to display the information on the display 5101 on portable electronic devices such as smartphones. You can also check it there.

[0341] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0342] The robot 2100 shown in Figure 8(B) consists of a computing unit 2110, an illuminance sensor 2101, and a microphone. Lophone 2102, upper camera 2103, speaker 2104, display 2105, bottom It is equipped with a camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.

[0343] Microphone 2102 has the function of detecting the user's voice and ambient sounds, etc. Speaker 2104 has the function of emitting sound. Robot 2100 has a microphone Using the 2102 and speaker 2104, communication with the user is possible. It is possible.

[0344] The display 2105 has the function of displaying various information. The robot 2100 is The user can display the desired information on the display 2105. The 2105 may have a touch panel. Also, the display 2105 is removable. It can be any information terminal capable of charging, and by installing it in a fixed position on the robot 2100, And it enables the transfer of data.

[0345] The upper camera 2103 and lower camera 2106 are used to image the area around the robot 2100. It has the ability to detect obstacles. Furthermore, the obstacle sensor 2107 uses the moving mechanism 2108 to detect robot 210 Robot 21 can detect the presence or absence of obstacles in the direction of travel as it moves forward. 00 uses the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107 The light-emitting device according to one aspect of the present invention can recognize its surroundings and move safely. It can be used in display 2105.

[0346] Figure 8(C) shows an example of a goggle-type display. For example, the housing 5000, the display unit 5001, the speaker 5003, the LED lamp 5004, Connection terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotational speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, electric current, voltage, power, radiation (including functions for measuring radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), It includes a crossphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, and the like.

[0347] The light-emitting device according to one aspect of the present invention can be used in the display unit 5001 and the display unit 5002. .

[0348] Figure 9 shows an example in which the light-emitting device described in Embodiment 2 is used in a desk lamp, which is a lighting device. The desk lamp shown in Figure 9 has a housing 2001 and a light source 2002. As for the second example, the lighting device described in Embodiment 3 may be used.

[0349] Figure 10 shows the light-emitting device described in Embodiment 2 used as an indoor lighting device 3001. This is an example. The light-emitting device described in Embodiment 2 is a light-emitting device with high luminous efficiency. This allows for a lighting device with low power consumption. Also, the light-emitting device described in Embodiment 2 Because chairs can be made to cover a large area, they can be used as large-area lighting devices. The light-emitting device described in Embodiment 2 is thin and can therefore be used as a thinned lighting device. This becomes possible.

[0350] The light-emitting device described in Embodiment 2 can also be mounted on the windshield or dashboard of an automobile. It can be mounted. Figure 11 shows the light-emitting device described in Embodiment 2 mounted on the front of an automobile. This shows one embodiment for use in a display or dashboard. Display areas 5200 to 5203 are This is a display provided using the light-emitting device described in Embodiment 2.

[0351] Display area 5200 and display area 5201 are in an embodiment provided on the windshield of an automobile. A display device equipped with the light-emitting device described in 2. The light-emitting device described in Embodiment 2. This is achieved by fabricating the first and second electrodes with translucent electrodes, so that the opposite side is transparent. It can be used as a display device that is visible through a transparent, so-called see-through state. If it's a display, even if it's installed on the windshield of a car, it won't obstruct the view. It can be installed. Furthermore, if transistors or other components for driving are to be installed, organic semiconductors may be used. Organic transistors made of conductive materials, and transistors using oxide semiconductors, etc., have light transmission properties. It is best to use a transistor that has one.

[0352] The display area 5202 is equipped with the light-emitting device described in Embodiment 2, which is provided in the pillar portion. This is a display device. The display area 5202 displays images from an imaging device installed on the vehicle body. By extending it, the view obstructed by the pillar can be compensated for. Also, similarly, The display area 5203 provided on the shoeboard section allows the view obstructed by the vehicle body to be seen by the car. By displaying images from externally mounted imaging devices, blind spots are compensated for, and safety is enhanced. It can be done by projecting images that complement the parts that are not visible, making it more natural. Safety checks can be performed without any sense of unease.

[0353] Display area 5203 also displays navigation information, speedometer, tachometer, air conditioning settings, etc. By displaying this information, various types of information can be provided. The display can be adjusted to suit the user's preferences. The displayed items and layout can be changed. Note that this information is displayed in area 520. It can also be provided in display areas 0 to 5203. The 5203 can also be used as a lighting device.

[0354] Figures 12(A) and (B) also show a foldable portable information terminal 5150. The portable information terminal 5150 consists of a housing 5151, a display area 5152, and a bendable portion 515 It has 3. Figure 12(A) shows the portable information terminal 5150 in its unfolded state. Figure 12( B) shows the portable information terminal in its folded state. The portable information terminal 5150 has a large display area Despite having a 5152mm field of view, it folds up compactly and is highly portable.

[0355] The display area 5152 can be folded in half by the bending portion 5153. Bending portion 515 3 consists of an expandable member and multiple support members, and when folded, the expandable The member stretches. The bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It folds up.

[0356] Note that the display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). It may also be a device. The light-emitting device according to one aspect of the present invention can be used in the display area 5152. Cut.

[0357] Figures 13(A) to (C) also show a foldable portable information terminal 9310. Figure 13 (A) shows the portable information terminal 9310 in its unfolded state. Figure 13(B) shows the unfolded state or This shows the portable information terminal 9310 in an intermediate state, transitioning from one folded state to the other. Figure 13(C) shows the folded state of the personal digital assistant 9310. Personal digital assistant 9310 It offers excellent portability when folded and a seamless, wide display area when unfolded. This provides excellent readability in the display.

[0358] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). It may also be an input / output device. In addition, the display panel 9311 is connected via the hinge 9313. By bending the two housings 9315, the mobile information terminal 9310 is unfolded. It can be reversibly transformed from a folded state. A light-emitting device according to one aspect of the present invention It can be used with the display panel 9311. [Examples]

[0359] <<Synthesis Example 1>> In this embodiment, the organic compound shown as structural formula (100) in Embodiment 1, N,N -Bis(4-cyclohexylphenyl)-9,9,-dimethyl-9H-fluorene-2- This section describes the synthesis method of amine (abbreviated as dchPAF). The structure of dchPAF is as follows: This will be shown.

[0360] [ka]

[0361] <Step 1: N,N-bis(4-cyclohexylphenyl)-9,9,-dimethyl-9 Synthesis of H-fluoren-2-amine (abbreviation: dchPAF) 10.6g of 9,9-dimethyl-9H-fluoren-2-amine (51mm) in a three-necked flask. ol), 4-cyclohexyl-1-bromobenzene 18.2g (76 mmol), sodium Add 21.9g (228mmol) of um-tert-butoxide and 255mL of xylene. After degassing under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred. Here, allyl palladium chloride dimer(II) (abbreviated as [(Allyl) PdCl]2) 370 mg (1.0 mmol), di-tert-butyl (1-methyl-2) ,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP(registered trademark))16 60 mg (4.0 mmol) was added, and this mixture was heated at 120°C for approximately 5 hours. Afterward, the flask temperature was returned to approximately 60°C, and approximately 4 mL of water was added to precipitate the solid. The solid was filtered off. The filtrate was concentrated, and the resulting solution was subjected to silica gel column chromatography. It was purified using [method]. The resulting solution was concentrated to obtain a concentrated toluene solution. This toluene solution was then [method]. The solution was added dropwise to tanol and reprecipitation occurred. The precipitate was filtered at approximately 10°C, and the resulting solid was heated at approximately 80°C. The product was dried under reduced pressure to obtain 10.1 g of the target white solid in a yield of 40%. Step 1 The synthesis scheme for dchPAF is shown below.

[0362] [ka]

[0363] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The 1H-NMR chart is shown in Figure 14. This indicates the synthesis. In the example, it was found that dchPAF could be synthesized.

[0364] 1H-NMR.δ(CDCl3):7.60(d,1H,J=7.5Hz),7.53( d,1H,J=8.0Hz),7.37(d,2H,J=7.5Hz),7.29(td ,1H,J=7.5Hz,1.0Hz),7.23(td,1H,J=7.5Hz,1. 0Hz),7.19(d,1H,J=1.5Hz),7.06(m,8H),6.97( dd,1H,J=8.0Hz,1.5Hz),2.41-2.51(brm,2H),1 .79-1.95(m,8H),1.70-1.77(m,2H),1.33-1.45 (brm, 14H), 1.19-1.30 (brm, 2H).

[0365] Next, 5.6 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 215°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 12.0 mL / min. The process was carried out. After sublimation purification, 5.2 g of a slightly yellowish-white solid was obtained with a recovery rate of 94%.

[0366] Next, the ultraviolet-visible absorption spectrum of dchPAF in a toluene solution (hereinafter simply referred to as "absorption spectrum") The absorption spectrum (called "Tor") and emission spectrum were measured. For the measurement of the absorption spectrum, ultraviolet-visible light was used. A photophotometer (V550 model, manufactured by JASCO Corporation) was used to measure the emission spectrum using fluorescence light. Both measurements were performed at room temperature using a thermometer (FS920, manufactured by Hamamatsu Photonics Ltd.). Furthermore, a quartz cell was used for the measurement. The obtained absorption and emission spectra The measurement results are shown in Figure 15. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown is obtained from the absorption spectrum measured by placing a toluene solution in a quartz cell. This shows the result after subtracting the absorption spectrum measured by placing only the element in a quartz cell.

[0367] As shown in Figure 15, the organic compound dchPAF had an emission peak at 354 nm. .

[0368] Next, the organic compound, dchPAF, was analyzed using liquid chromatography-mass spectrometry (Liquid Chr). Omatography Mass Spectrometry (abbreviated as LC / MS analysis) Mass (MS) analysis was performed using )).

[0369] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C8 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. The pull was prepared by dissolving dchPAF of any concentration in toluene and diluting it with acetonitrile. The injection volume was 5.0 μL.

[0370] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0371] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=525 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 50 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 16 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0372] From the results in Figure 16, it can be seen that in dchPAF, the product ions are mainly located around m / z = 525. It was found to be detectable. Furthermore, the results shown in Figure 16 are characteristic of dchPAF. Since this shows such results, it is important for identifying dchPAF contained in the mixture. This can be considered essential data.

[0373] The flag for m / z=367 was observed when measured at a collision energy of 50eV. The ment ion is formed when the CN bond of dchPAF is cleaved, resulting in an N-(4-cyclohexagonal) ion. It is presumed to be xylphenyl)-N-(9,9-dimethyl-9H-fluoren-2yl)amine. This is one of the characteristics of dchPAF.

[0374] Furthermore, Figure 82 shows the refractive index of dchPAF measured with a spectroscopic ellipsometer (J.A. Woo-ram). The results of measurements using the M-2000U (manufactured by Japan Co., Ltd.) are shown. For the measurements, a quartz substrate was used. The film used consisted of layers of material deposited by vacuum deposition, with a thickness of approximately 50 nm. Note that the figure was obtained using ordinary light. n, Ordinary, is the refractive index of the normal ray, and n, Extra-o is the refractive index of the extraordinary ray. I wrote "rdinary".

[0375] From this figure, it can be seen that dchPAF is normal light throughout the entire blue emission region (455nm to 465nm). The refractive index is in the range of 1.50 to 1.75, and the ordinary refractive index at 633 nm is also... The values ​​were also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. [Examples]

[0376] ≪Synthesis Example 2≫ In this embodiment, the organic compound shown as structural formula (101) in Embodiment 1, N-[ (4'-Cyclohexyl)-1,1'-Biphenyl-4yl]-N-(4'-Cyclohexyl) (Abbreviation: chBich) 9,9-dimethyl-9H-fluorene-2-amine The synthesis method for PAF is described below. The structure of chBichPAF is shown below.

[0377] [ka]

[0378] <Step 1: N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H- Synthesis of fluoren-2-ylamine 10.5g of 9,9-dimethyl-9H-fluoren-2-amine (50ml) in a three-necked flask. ol), 4-cyclohexyl-1-bromobenzene 12.0g (50 mmol), sodium Add 14.4g (150mmol) of um-tert-butoxide and 250mL of xylene. After degassing under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred. Here, allyl palladium chloride dimer(II) (abbreviated as [(Allyl)P dCl]2) 183 mg (0.50 mmol), di-tert-butyl (1-methyl-2) ,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP(registered trademark))82 1 mg (2.0 mmol) was added, and the mixture was heated at 90°C for approximately 6 hours. The flask temperature was lowered to approximately 60°C, approximately 4 mL of water was added, and the precipitated solid was filtered off. Filtrate The solution was concentrated and purified by silica gel column chromatography. The liquid was concentrated to obtain a concentrated toluene solution. This toluene solution was dried under vacuum at approximately 60°C. Then, 17.3 g of the target product, a brownish oily substance, was obtained in a yield of 92%. Step 1 synthesis Chiem is shown in the following equation.

[0379] [ka]

[0380] <Step 2: N-[(4'-cyclohexyl)-1,1'-biphenyl-4yl]-N -(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene-2-amine Synthesis of (abbreviation: chBichPAF) In a three-necked flask, place the N-(4-cyclohexylphenyl)-N-(9, obtained in Step 1) into a three-necked flask. 9-dimethyl-9H-fluoren-2yl)amine 4.7g (12.8 mmol), 4' -Cyclohexyl-4-chloro-1,1'-biphenyl 3.5g (12.8 mmol), Sodium tert-butoxide 3.7g (38.5 mmol), xylene 65mL After adding the mixture and degassing it under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred. Here, allyl palladium chloride dimer(II) (abbreviated as [(Allyl )PdCl]2) 47 mg (0.13 mmol), di-tert-butyl (1-methyl- 2,2-Diphenylcyclopropyl)phosphine (abbreviation: cBRIDP(registered trademark))1 80 mg (0.51 mmol) was added, and the mixture was heated at 110°C for approximately 5 hours. Subsequently, the flask temperature was lowered to approximately 60°C, about 1 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was purified by silica gel column chromatography. The solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to this toluene solution. Then, it was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at approximately 20°C, and the resulting solid was approximately The mixture was dried under reduced pressure at 80°C to obtain 5.3 g of a white solid in 69% yield. Step 2 synthesis skim The formula is shown below.

[0381] [ka]

[0382] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The 1H-NMR chart is shown in Figure 17. This indicates the synthesis. In the example, it was found that chBichPAF could be synthesized.

[0383] 1 H-NMR.δ(CDCl3):7.63(d,1H,J=7.5Hz),7.57( d,1H,J=7.5Hz),7.51(d,2H,J=8.0Hz),7.46(d, 2H,J=7.5Hz),7.38(d,1H,J=7.5Hz),7.30(td,1 H,J=7.0Hz,1.5Hz),7.20-7.28(m,6H)7.01-7.1 8(m,7H),2.43-2.57(brm,2H),1.81-1.96(m,8H ),1.71-1.79(brm,2H),1.34-1.50(brm,14H),1 .20-1.32 (brm, 2H).

[0384] Next, 3.5 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 270°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 12.3 mL / min. The process was carried out. After sublimation purification, 3.1 g of a slightly yellowish-white solid was obtained with a recovery rate of 88%.

[0385] Next, the ultraviolet-visible absorption spectrum of chBichPAF in a toluene solution (hereinafter simply referred to as "absorption") The "spectrum" (also known as the emission spectrum) and the emission spectrum were measured. For measuring the absorption spectrum, ultraviolet light was used. Using a visible spectrophotometer (V550 model, manufactured by JASCO Corporation), the emission spectrum was measured as follows: Both measurements were performed at room temperature using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics Ltd.). Furthermore, a quartz cell was used for measurement. The obtained absorption spectrum and emission spectrum The measurement results for Torr are shown in Figure 18. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown in 18 is obtained from the absorption spectrum measured by placing a toluene solution in a quartz cell. This shows the result after subtracting the absorption spectrum measured with only toluene placed in a quartz cell. .

[0386] As shown in Figure 18, the organic compound chBichPAF has an emission peak at 357 nm. He was.

[0387] Next, the organic compound, chBichPAF, was analyzed using liquid chromatography-mass spectrometry (Liquid Chromatography Mass Spectrometry (Abbreviation: LC / M) Mass (MS) analysis was performed using S-analysis.

[0388] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C8 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves chBichPAF of any concentration in toluene and dilutes it with acetonitrile. The amount was adjusted and injected at 5.0 μL.

[0389] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0390] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=601 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 60 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 19 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0391] From the results in Figure 19, chBichPAF is mainly product i around m / z = 601. It was found that the ON state was detected. Note that the results shown in Figure 19 are from chBichPAF. Because it exhibits characteristic results, chBichPAF contained in the mixture This can be considered important data for identifying [the subject].

[0392] The flag for m / z=442 was observed when measured at a collision energy of 70eV. The ment ion is formed when the CN bond of chBichPAF is cleaved, resulting in an N-(4'- Cyclohexyl-1,1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H- It is presumed to be fluoren-2-ylamine, and is one of the characteristics of chBichPAF.

[0393] Furthermore, Figure 83 shows the refractive index of chBichPAF measured with a spectroscopic ellipsometer (J.A.W. The results of measurements using the M-2000U (manufactured by Ram Japan Co., Ltd.) are shown. A film was used in which each layer of material was deposited on a plate by vacuum deposition, resulting in a film of approximately 50 nm thickness. Note that the figure shows... n, Ordinary, is the refractive index of ordinary light rays, and n, Extr, is the refractive index of extraordinary light rays. I wrote "a-ordinary".

[0394] From this figure, it can be seen that chBichPAF covers the entire blue emission region (455nm to 465nm). The ordinary refractive index is in the range of 1.50 to 1.75, and the ordinary refractive index at 633 nm The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. Ta.

[0395] Next, the glass transition temperature (hereinafter referred to as "Tg") of chBichPAF was measured. This is a differential scanning calorimetry system (PYRIS1DSC, manufactured by PerkinElmer Japan Co., Ltd.) Using this method, the powder was placed on an aluminum cell and measured. As a result, the Tg of chBichPAF was 9 It was 6℃. [Examples]

[0396] ≪Synthesis Example 3≫ In this embodiment, the organic compound shown as structural formula (102) in Embodiment 1, N,N -Bis(4-cyclohexylphenyl)-N-(spiro[cyclohexane-1,9'[9 Regarding the synthesis method of [H]fluoren]-2'yl)amine (abbreviation: dchPASchF) Let me explain. The structure of dchPASchF is shown below.

[0397] [ka]

[0398] <Step 1: Synthesis of 4-cyclohexylaniline> 21.5 g (90 mmol) of 4-cyclohexyl-1-bromobenzene in a three-necked flask. 450 mL of toluene was added, and the mixture was degassed under reduced pressure, after which the flask was purged with nitrogen. This solution was cooled and stirred to approximately -20°C. Here, allyl palladium chloride dimer(II) (Abbreviation: [(Allyl)PdCl]2) 823mg (2.25 mmol), di-ter t-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cB) RIDP(registered trademark) 3690 mg (9.0 mmol) was added to this solution. Add 100 mL of mol / L lithium bis(hexamethyldisilazide) toluene solution dropwise. Then, the flask was heated to approximately 120°C and the mixture was allowed to react for about 2 hours. After cooling, approximately 200 mL of water was added and allowed to stand, separating the organic layer from the aqueous layer. Approximately 100 mL of Luene was added and the reaction product was extracted. The resulting organic layer and the previously separated organic layer were then separated. The mixture was washed with saturated saline solution. Magnesium sulfate was added to this solution, and the moisture was dried. The solution was dried and filtered. The resulting toluene solution was concentrated and subjected to silica gel column chromatography. It was purified using [method]. The resulting solution was concentrated to obtain a concentrated toluene solution. This toluene solution was then [processed]. The mixture was dried outdoors at approximately 60°C, yielding 14.5 g of the target substance, a brownish-oil, with a yield of 92%. The synthesis scheme for Step 1 is shown in the following formula.

[0399] [ka]

[0400] <Step 2: N-(4-cyclohexylphenyl)-N-(spiro[cyclohexane- Synthesis of 1,9'[9H]fluoren]-2'-yl)amine 3.0 g (16.9 mmol) of 4-cyclohexylaniline and 2'-bromide are placed in a three-necked flask. Mo(spiro[cyclohexane-1,9'[9H]fluorene]) 5.3g (16.9mm ol), sodium tert-butoxide 4.9g (50.7 mmol), xylene 8 5 mL was added, degassed under reduced pressure, and then the flask was purged with nitrogen. This solution was then purged for approximately 6 The mixture was heated and stirred to 0°C. Here, allyl palladium chloride dimer(II) (abbreviated as [(Al [lyl)PdCl]2)62mg (0.17mmol), di-tert-butyl (1-methyl) (Tyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) 280 mg (0.67 mmol) was added. This mixture was heated to approximately 90°C and heated for approximately 7 hours. The reaction was allowed to proceed. Afterwards, the flask temperature was returned to approximately 60°C, and about 1 mL of water was added, causing precipitation. The solid was filtered off. The filtrate was concentrated, and the resulting solution was analyzed by silica gel column chromatography. It was purified. The resulting solution was concentrated to obtain a concentrated toluene solution. This toluene solution was then vacuum-sealed. The mixture was dried at approximately 60°C, yielding 5.1 g of the target brownish-orange oily substance with a yield of 73%. Step 2 N-(4-cyclohexylphenyl)-N-(spiro[cyclohexane-1 The synthesis scheme for ,9'[9H]fluoren]-2'-yl)amine is shown below.

[0401] [ka]

[0402] <Step 3: N,N-bis(4-cyclohexylphenyl)-N-(spiro[cyclohexylphenyl) Xan-1,9'[9H]fluorene]-2'yl)amine (abbreviation: dchPASchF) ) synthesis > In a three-necked flask, add the N-(4-cyclohexylphenyl)-N-(spi) obtained in step 2. Ro[cyclohexane-1,9'[9H]fluorene]-2'-yl)amine 2.5g (6 0.2 mmol), 4-cyclohexyl-1-bromobenzene 1.5 g (6.2 mmol) 1.8g (18.6 mmol) of sodium tert-butoxide, 31mL of xylene After adding the mixture and degassing it under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred until it reached this point. Here, allyl palladium chloride dimer(II) (abbreviated as [(Ally l)PdCl]2)23mg (0.062 mmol), di-tert-butyl(1-methicillin) (2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) )88 mg (0.248 mmol) was added, and this mixture was heated at 90°C for approximately 5 hours. Then, the flask temperature was returned to approximately 60°C, approximately 1 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was purified by silica gel column chromatography. The solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to this toluene solution. The solution was then concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at approximately 20°C, and the resulting solid was obtained. The sample was dried under reduced pressure at approximately 80°C to obtain 3.1 g of the target white solid in a yield of 88%. The synthesis scheme for dchPASchF of p3 is shown below.

[0403] [ka]

[0404] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The 1H-NMR chart is shown in Figure 20. This indicates the synthesis. In the example, N,N-bis(4-cyclohexylphenyl)-N-(spiro[cyclohex Sun-1,9'[9H]fluorene]-2'yl)amine (abbreviation: dchPASchF) It was found that it could be synthesized.

[0405] 1 H-NMR.δ(CDCl3):7.60-7.65(m,2H),7.54(d,1 H,J=8.0Hz),7.28-7.35(m,2H),7.19-7.24(t,1 H,J=7.5Hz),7.02-7.12(m,8H),6.97-7.22(d,1 H,J=8.0Hz),2.40-2.52(brm,2H),1.79-1.95(m ,10H),1.63-1.78(m,9H),1.55-1.63(m,1H),1. 32-1.46(m,8H),1.18-1.30(brm,2H).

[0406] Next, 3.1 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 235°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 12.3 mL / min. The process was carried out. After sublimation purification, 2.8 g of a slightly yellowish-white solid was obtained with a recovery rate of 92%.

[0407] Next, the ultraviolet-visible absorption spectrum of dchPASchF in a toluene solution (hereinafter simply referred to as "absorption") The "spectrum" (also known as the emission spectrum) and the emission spectrum were measured. For measuring the absorption spectrum, ultraviolet light was used. Using a visible spectrophotometer (V550 model, manufactured by JASCO Corporation), the emission spectrum was measured as follows: Both measurements were performed at room temperature using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics Ltd.). Furthermore, a quartz cell was used for measurement. The obtained absorption spectrum and emission spectrum The measurement results for Torr are shown in Figure 21. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown in 21 is obtained from the absorption spectrum measured by placing a toluene solution in a quartz cell. This shows the result after subtracting the absorption spectrum measured with only toluene placed in a quartz cell. .

[0408] As shown in Figure 21, the organic compound dchPASchF has an emission peak at 352 nm. He was.

[0409] Next, the organic compound, dchPASchF, was analyzed using liquid chromatography-mass spectrometry (Liquid Chromatography Mass Spectrometry (Abbreviation: LC / M) Mass (MS) analysis was performed using S-analysis.

[0410] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C8 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves dchPASchF of any concentration in toluene and dilutes it with acetonitrile. The amount was adjusted and injected at 5.0 μL.

[0411] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0412] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=565 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 50 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 22 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0413] From the results in Figure 22, dchPASchF is mainly product i around m / z = 565. It was found that the ON state was detected. Note that the results shown in Figure 22 are due to dchPASchF Since it exhibits characteristic results, dchPASchF contained in the mixture This can be considered important data for identifying [the subject].

[0414] The flag for m / z=407 was observed when measured at a collision energy of 50eV. The ment ion is formed when the CN bond of dchPASchF is cleaved, resulting in N-(4-) ions. Chlohexylphenyl)-N-(spiro[cyclohexane-1,9'[9H]fluorene It is presumed to be a ]-2'-ylamine and is one of the characteristics of dchPASchF.

[0415] Furthermore, Figure 84 shows the refractive index of dchPASchF using a spectroscopic ellipsometer (J.A.U. The results of measurements using the M-2000U (manufactured by Ram Japan Co., Ltd.) are shown. A film was used in which each layer of material was deposited on a plate by vacuum deposition, resulting in a film of approximately 50 nm thickness. Note that the figure shows... n, Ordinary, is the refractive index of ordinary light rays, and n, Extr, is the refractive index of extraordinary light rays. I wrote "a-ordinary".

[0416] From this figure, dchPASchF covers the entire blue emission region (455nm to 465nm). The ordinary refractive index is in the range of 1.50 to 1.75, and the ordinary refractive index at 633 nm The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. Ta. [Examples]

[0417] <<Synthesis Example 4>> In this embodiment, the organic compound shown as structural formula (103) in Embodiment 1, N-[ (4'-Cyclohexyl)-1,1'-Biphenyl-4yl]-N-(4'-Cyclohexyl) (Luphenyl)-N-(Spiro[cyclohexane-1,9'-[9H]-fluorene]-2 The synthesis method for 'yl)amine (abbreviation: chBichPASchF) will be explained. The structure of hBichPASchF is shown below.

[0418] [ka]

[0419] <Step 1: Synthesis of 4-cyclohexylaniline> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 3 in Example 3.

[0420] <Step 2: N-(4-cyclohexylphenyl)-N-(spiro[cyclohexane- Synthesis of 1,9'[9H]fluoren]-2'-yl)amine The synthesis was carried out in the same manner as in step 2 of synthesis example 3 of Example 3.

[0421] <Step 3: N-[(4'-cyclohexyl)-1,1'-biphenyl-4yl]-N -(4-cyclohexylphenyl)-N-(spiro[cyclohexane-1,9'-[9H Synthesis of ]-fluoren]-2'yl)amine (abbreviation: chBichPASchF) In a three-necked flask, add the N-(4-cyclohexylphenyl)-N-(spi) obtained in step 2. Ro[cyclohexane-1,9'[9H]fluorene]-2'-yl)amine 2.5g (6 0.2 mmol), 4'-cyclohexyl-4-chloro-1,1'-biphenyl 1.7 g ( 6.2 mmol), sodium tert-butoxide 1.8 g (18.6 mmol), 31 mL of xylene was added, and after degassing under reduced pressure, the flask was purged with nitrogen. The mixture was heated and stirred to approximately 50°C. Here, the allyl palladium chloride dimer (I I) (Abbreviation: [(Allyl)PdCl]2) 23 mg (0.062 mmol), di-t ert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: Add 88 mg (0.248 mmol) of cBRIDP(registered trademark) to this mixture, and 1 The mixture was heated at 10°C for approximately 5 hours. After that, the temperature of the flask was lowered to approximately 60°C, and approximately 1 mL of water was added. In addition, the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was subjected to silica gel column chromatography. It was purified by tography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the solution and concentrated under reduced pressure to obtain an ethanol suspension. Precipitation occurred at approximately 20°C. The material was filtered, and the resulting solid was dried under reduced pressure at approximately 80°C to obtain 2.7 g of the target white solid. The yield was 68%. The synthesis scheme for Step 3 is shown in the following equation.

[0422] [ka]

[0423] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The 1H-NMR chart is shown in Figure 23. This indicates the synthesis. In the example, N-[(4'-cyclohexyl)-1,1'-biphenyl-4yl]-N- (4-Cyclohexylphenyl)-N-(Spiro[Cyclohexane-1,9'-[9H] -Fluorene]-2'yl)amine (abbreviated as chBichPASchF) was successfully synthesized. I found out.

[0424] 1 H-NMR.δ(CDCl3):7.65(d,2H,J=8.0Hz),7.58( d,1H,J=8.0Hz),7.51(d,2H,J=8.5Hz),7.46(m, 2H),7.39(d,1H,1.5Hz),7.32(t,1H,J=8.0Hz), 7.21-7.38(m,3H),7.14-7.18(m,2H),7.08-7.1 4(m,4H),7.06(dd,1H,J=8.0Hz,1.5Hz),2.43-2 .57(brm,2H),1.80-1.97(m,10H),1.64-1.80(m ,9H),1.56-1.64(m,1H),1.34-1.53(m,8H),1.2 0-1.32 (brm, 2H).

[0425] Next, 2.6 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 275°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 12.3 mL / min. The process was carried out. After sublimation purification, 2.3 g of a slightly yellowish-white solid was obtained with a recovery rate of 89%.

[0426] Next, the ultraviolet-visible absorption spectrum of the toluene solution of chBichPASchF (hereinafter simply The absorption spectrum (also known as the emission spectrum) and emission spectrum were measured. The emission spectrum was measured using a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation). For both measurements, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used, and both measurements were taken at room temperature. The following was performed. A quartz cell was used for the measurement. The obtained absorption spectrum and emission The spectral measurement results are shown in Figure 24. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown in Figure 24 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The following shows the result after subtracting the absorption spectrum measured by placing only toluene in a quartz cell. It is.

[0427] As shown in Figure 24, the organic compound chBichPASchF exhibits an emission peak at 357 nm. He possessed it.

[0428] Next, the organic compound, chBichPASchF, was analyzed by liquid chromatography-mass spectrometry (Liqu id Chromatography Mass Spectrometry (abbreviation: L Mass (MS) analysis was performed using C / MS analysis.

[0429] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C8 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves chBichPASchF of any concentration in toluene and dilutes it with acetonitrile. After adjusting the solution, the injection volume was set to 5.0 μL.

[0430] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0431] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=641 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 60 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 25 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0432] From the results in Figure 25, it can be seen that chBichPASchF is mainly produced around m / z=641. It was found that ctions were detected. Note that the results shown in Figure 25 are from chBichPA Since this shows characteristic results derived from SchF, the chB contained in the mixture This can be considered important data for identifying ichPASchF.

[0433] The flag for m / z=482 observed when measured at a collision energy of 60eV is also shown. The ment ion is formed when the CN bond of chBichPASchF is cleaved, and N-[ (4'-Cyclohexyl)-1,1'-Biphenyl-4-yl]-N-(Spiro[Cyclo It is presumed to be hexane-1,9'-[9H]-fluorene]-2'-yl)amine, ch This is one of the characteristics of BichPASchF.

[0434] Furthermore, Figure 85 shows the refractive index of chBichPASchF measured with a spectroscopic ellipsometer (J.E.). The results of measurements using the M-2000U (manufactured by Woolam Japan Co., Ltd.) are shown below. A film was used in which each layer of material was deposited on a quartz substrate by vacuum deposition, with a thickness of approximately 50 nm. This includes n, Ordinary, which is the refractive index of ordinary light, and n, E, which is the refractive index of extraordinary light. I described it as "xtra-ordinary".

[0435] From this figure, chBichPASchF is in the blue emission region (455nm to 465nm). ) The ordinary refractive index is in the range of 1.50 to 1.75 throughout the entire region, and at 633 nm The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. Understood.

[0436] Next, the glass transition temperature (hereinafter referred to as "Tg") of chBichPASchF was measured. Tg is measured using a differential scanning calorimetry system (PYRIS1D, manufactured by PerkinElmer Japan Co., Ltd.). Using SC, the powder was placed on an aluminum cell and measured. As a result, chBichPASch The Tg of F was 102°C. [Examples]

[0437] ≪Synthesis Example 5≫ In this embodiment, the organic compound shown as structural formula (104) in Embodiment 1, N-( 4-Cyclohexylphenyl)-bis(spiro[cyclohexane-1,9'-[9H]f This document explains the synthesis method of ruolene]-2'-ylamine (abbreviation: SchFB1chP). The structure of SchFB1chP is shown below.

[0438] [ka]

[0439] <Step 1: Synthesis of 4-cyclohexylaniline> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 3 in Example 3.

[0440] <Step 2: N-(4-cyclohexylphenyl)-N-(spiro[cyclohexane- Synthesis of 1,9'[9H]fluoren]-2'-yl)amine The synthesis was carried out in the same manner as in step 2 of synthesis example 3 of Example 3.

[0441] <Step 3: N-(4-cyclohexylphenyl)-bis(spiro[cyclohexane- 1,9'-[9H]fluorene]-2'-yl)amine (abbreviation: SchFB1chP) Synthesis> 3.0g of 4-cyclohexylaniline (16) is placed in a three-necked flask, as shown in the synthesis method in Step 2. 0.9 mmol), 2'-bromo(spiro[cyclohexane-1,9'[9H]fluorene) ]) 5.3g (16.9 mmol), sodium tert-butoxide 4.9g (50 Add 0.7 mmol) and 85 mL of xylene, degas under reduced pressure, and then nitrify the flask. Elementary substitution was performed. This solution was heated and stirred to approximately 60°C. Here, dimerized palladium allyl chloride was added. Form (II) (abbreviation: [(Allyl)PdCl]2) 62 mg (0.17 mmol), di -tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviated) 280 mg (0.67 mmol) of cBRIDP (registered trademark) was added to this mixture. The mixture was heated to approximately 90°C and reacted for approximately 7 hours. After that, the temperature of the flask was returned to approximately 60°C. Approximately 1 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was silica gel. The solution was purified by column chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to this toluene solution, and it was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at 0°C, and the resulting solid was dried under reduced pressure at approximately 80°C to obtain the desired white solid. The body was obtained in 0.95 g with a yield of 8.8%. The synthesis scheme for Step 3 is shown in the following equation.

[0442] [ka]

[0443] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 ( 1 Analysis results by H-NMR The results are shown below. Also, 1 The H-NMR chart is shown in Figure 26. In this case, N-(4-cyclohexylphenyl)-bis(spiro[cyclohexane-1,9 '-[9H]fluorene]-2'-ylamine (abbreviation: SchFB1chP) is synthesized I realized they had arrived.

[0444] 1 H-NMR.δ(CDCl3):7.64(t,4H,J=8.0Hz),7.59( d,2H,J=8.5Hz),7.39(brs,2H),7.33(t,2H,J=7 .5Hz),7.20-7.25(m,2H),7.12(brs,4H),7.08( d,2H,J=8.0Hz),2.44-2.52(brm,1H),1.63-1.9 7(m,23H),1.50-1.61(m,2H),1.34-1.48(m,4H) ,1.20-1.32(brm,1H).

[0445] Next, 0.93 g of the obtained solid was purified by sublimation using the train sublimation method. Purification was performed by heating at 250°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 13.3 mL / min. The process was carried out. After sublimation purification, 0.64 g of a slightly yellowish-white solid was obtained with a recovery rate of 69%.

[0446] Next, the ultraviolet-visible absorption spectrum of SchFB1chP in a toluene solution (hereinafter simply referred to as "absorption") The "spectrum" (also known as the emission spectrum) and the emission spectrum were measured. For measuring the absorption spectrum, ultraviolet light was used. Using a visible spectrophotometer (V550 model, manufactured by JASCO Corporation), the emission spectrum was measured as follows: Both measurements were performed at room temperature using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics Ltd.). Furthermore, a quartz cell was used for measurement. The obtained absorption spectrum and emission spectrum The measurement results for Torr are shown in Figure 27. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown in 27 is obtained from the absorption spectrum measured by placing a toluene solution in a quartz cell. This shows the result after subtracting the absorption spectrum measured with only toluene placed in a quartz cell. .

[0447] As shown in Figure 27, the organic compound SchFB1chP has an emission peak at 368 nm. He was.

[0448] Next, the organic compound SchFB1chP was analyzed using liquid chromatography-mass spectrometry (Liquid Chromatography Mass Spectrometry (Abbreviation: LC / M) Mass (MS) analysis was performed using S-analysis.

[0449] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C8 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves SchFB1chP of any concentration in toluene and dilutes it with acetonitrile. The amount was adjusted and injected at 5.0 μL.

[0450] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0451] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the ionized m / z=639 component is subjected to argon gas in the collision cell. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 60 eV. The mass range measured was m / z (mass charge). The ratio of (T) was set to 100-1500. Figure 28 shows the dissociated product ions with a time of flight (T). The results detected by the OF) type MS are shown.

[0452] From the results in Figure 28, it can be seen that SchFB1chP is mainly product-driven around m / z = 639. It was found that the ON state was detected. Note that the results shown in Figure 28 are due to SchFB1chP. Since it exhibits characteristic results, the SchFB1chP contained in the mixture This can be considered important data for identifying [the subject].

[0453] The flag for m / z=481 was observed when measured at a collision energy of 60 eV. The ment ion is an N,N-bis ion formed when the CN bond of SchFB1chP is cleaved. (Spiro[cyclohexane-1,9'-[9H]-fluoren]-2'-yl)amine and This is presumed to be one of the characteristics of SchFB1chP.

[0454] Furthermore, Figure 86 shows the refractive index of SchFB1chP using a spectroscopic ellipsometer (J.A.W. The results of measurements using the M-2000U (manufactured by Ram Japan Co., Ltd.) are shown. A film was used in which each layer of material was deposited on a plate by vacuum deposition, resulting in a film of approximately 50 nm thickness. Note that the figure shows... n, Ordinary, is the refractive index of ordinary light rays, and n, Extr, is the refractive index of extraordinary light rays. I wrote "a-ordinary".

[0455] From this figure, it can be seen that SchFB1chP covers the entire blue emission region (455nm to 465nm). The ordinary refractive index is in the range of 1.50 to 1.75, and the ordinary refractive index at 633 nm The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. Ta.

[0456] Next, the Tg of SchFB1chP was measured. Tg was measured using a differential scanning calorimetry system (P&C Corporation). Using a PYRIS1DSC (manufactured by KinElmer Japan), powder was placed on an aluminum cell and measured. The temperature was determined to be 112°C. As a result, the Tg of SchFB1chP was 112°C. [Examples]

[0457] ≪Synthesis Example 6≫ In this embodiment, the organic compound shown as structural formula (105) in Embodiment 1, N-[ (3',5'-Ditermylbutyl)-1,1'-Biphenyl-4-yl]-N-(4 -Cyclohexylphenyl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation) This document explains the synthesis method for mmtBuBichPAF. The structure is shown below.

[0458] [ka]

[0459] <Step 1: 3',5'-Diter-butyl-4-chloro-1,1'-biphenyl Synthesis of > 13.5g (50ml) of 3,5-diter-butyl-1-bromobenzene in a three-necked flask. mol), 4-chlorophenylboronic acid 8.2g (52.5 mmol), potassium carbonate 2 1.8g (158mmol), 125mL toluene, 31mL ethanol, 40mL water After adding the mixture and degassing under reduced pressure, the flask was purged with nitrogen. Acetic acid was added to this mixture. Radium 225 mg (1.0 mmol), Tris(2-methylphenyl)phosphine 68 0 mg (2.0 mmol) was added and heated under reflux at 80°C for approximately 3 hours. Afterwards, it was allowed to cool to room temperature. The organic layer and aqueous layer were separated. Magnesium sulfate was added to this solution, and the water was dried to concentrate it. The obtained solution was purified by silica gel column chromatography. The mixture was concentrated and allowed to dry. Then, hexane was added and recrystallized. The resulting mixed solution was a white solid precipitate. After cooling with ice, the mixture was filtered. The resulting solid was vacuum-dried at approximately 60°C to obtain the desired white solid. 9.5 g was obtained in a yield of 63%. The synthesis scheme for Step 1 is shown in the following equation.

[0460] [ka]

[0461] <Step 2: N-(4-cyclohexylphenyl)-N-(9,9-dimethyl-9H- Synthesis of fluoren-2-ylamine The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 2.

[0462] <Step 3: N-[(3',5'-Ditter-butyl)-1,1'-Biphenyl- 4-yl]-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluore Synthesis of n-2-amine (abbreviation: mmtBuBichPAF) In a three-necked flask, add the 3',5'-diter-butyl-4-chloro- obtained in Step 1. 1,1'-biphenyl 3.2g (10.6 mmol), N-(4- obtained in step 2 Cyclohexylphenyl)-N-(9,9-dimethyl-9H-fluoren-2yl)amide 3.9g (10.6 mmol), sodium tert-butoxide 3.1g (31. Add 8 mmol) and 53 mL of xylene, degas under reduced pressure, and then nitrify the flask. The mixture was substituted with an element. This mixture was heated and stirred to approximately 50°C. Here, di-palladium allyl chloride was added. Merged (II) (abbreviation: [(Allyl)PdCl]2) 39 mg (0.11 mmol), Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine Add 150 mg (0.42 mmol) of the abbreviated name: cBRIDP (registered trademark) to this mixture. It was heated at 120°C for about 3 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL was added, and the solid precipitated. The precipitated solid was filtered off. The filtrate was concentrated to obtain the solution. The solution was purified by silica gel column chromatography. The resulting solution was concentrated, and concentrated toll A toluene solution was obtained. Ethanol was added to this toluene solution, and it was concentrated under reduced pressure to obtain an ethanol suspension. The obtained solid was filtered at approximately 20°C, and the obtained solid was dried under reduced pressure at approximately 80°C. 5.8 g of the target white solid was obtained in a yield of 87%. The synthesis scheme for Step 3 is shown below. This will be shown.

[0463] [ka]

[0464] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 (H-NMR) The analysis results are shown below. Also, 1The 1H-NMR chart is shown in Figure 29. This indicates the synthesis. In the example, N-[(3',5'-ditter-butyl)-1,1'-biphenyl-4 -yl]-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene It was found that -2-amine (abbreviated as mmtBuBichPAF) could be synthesized.

[0465] 1 H-NMR.δ(CDCl3):7.63(d,1H,J=7.5Hz),7.57( d,1H,J=8.0Hz),7.44-7.49(m,2H),7.37-7.42( m,4H),7.31(td,1H,J=7.5Hz,2.0Hz),7.23-7.2 7(m,2H),7.15-7.19(m,2H),7.08-7.14(m,4H), 7.05(dd,1H,J=8.0Hz,2.0Hz),2.43-2.53(brm, 1H),1.81-1.96(m,4H),1.75(d,1H,J=12.5Hz), 1.32-1.48(m,28H),1.20-1.31(brm,1H).

[0466] Next, 3.5 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 255°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 11.8 mL / min. The process was carried out. After sublimation purification, 3.1 g of a slightly yellowish-white solid was obtained with a recovery rate of 89%.

[0467] Next, the ultraviolet-visible absorption spectrum of mmtBuBichPAF in a toluene solution (hereinafter simply The absorption spectrum (also known as the emission spectrum) and emission spectrum were measured. The emission spectrum was measured using a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation). For both measurements, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used, and both measurements were taken at room temperature. The following was performed. A quartz cell was used for the measurement. The obtained absorption spectrum and emission The spectral measurement results are shown in Figure 30. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown in Figure 30 is the absorption spectrum measured by placing a toluene solution in a quartz cell. The following shows the result after subtracting the absorption spectrum measured by placing only toluene in a quartz cell. It is.

[0468] As shown in Figure 30, the organic compound mmtBuBichPAF exhibits an emission peak at 360 nm. He possessed it.

[0469] Next, the organic compound mmtBuBichPAF was analyzed using liquid chromatography-mass spectrometry (Liqu id Chromatography Mass Spectrometry (abbreviation: L Mass (MS) analysis was performed using C / MS analysis.

[0470] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C8 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves mmtBuBichPAF of any concentration in toluene and dilutes it with acetonitrile. After adjusting the solution, the injection volume was set to 5.0 μL.

[0471] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0472] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=631 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 60 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 31 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0473] From the results in Figure 31, mmtBuBichPAF is mainly produced around m / z=631. It was found that ctions were detected. Note that the results shown in Figure 31 are for mmtBuBic Since this shows characteristic results derived from hPAF, the mmt contained in the mixture This can be considered important data for identifying BuBichPAF.

[0474] The flag m / z=473 was observed when measured at a collision energy of 60eV. The ment ion is formed when the CN bond of mmtBuBichPAF is cleaved, resulting in an N-( 3',5'-Diter-butyl-1,1'-biphenyl-4-yl)-N-(9,9 It is presumed to be -dimethyl-9H-fluoren-2yl)amine, mmtBuBichPAF This is one of its characteristics.

[0475] Furthermore, Figure 87 shows the refractive index of mmtBuBichPAF measured with a spectroscopic ellipsometer (J.E.). The results of measurements using the M-2000U (manufactured by Woolam Japan Co., Ltd.) are shown below. A film was used in which each layer of material was deposited on a quartz substrate by vacuum deposition, with a thickness of approximately 50 nm. This includes n, Ordinary, which is the refractive index of ordinary light, and n, E, which is the refractive index of extraordinary light. I described it as "xtra-ordinary".

[0476] From this figure, mmtBuBichPAF is in the blue emission region (455nm to 465nm). ) The ordinary refractive index is in the range of 1.50 to 1.75 throughout the entire region, and at 633 nm The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. Understood.

[0477] Next, the Tg of mmtBuBichPAF was measured. Tg is measured using a differential scanning calorimetry system. Using a PYRIS1DSC manufactured by PerkinElmer Japan Co., Ltd., powder is placed on an aluminum cell. The temperature was measured. As a result, the Tg of mmtBuBichPAF was 102°C. [Examples]

[0478] ≪Synthesis Example 7≫ In this embodiment, the organic compound shown as structural formula (106) in Embodiment 1, N,N -Bis(3',5'-Ditterlybutyl-1,1'-Biphenyl-4-yl)-9, Synthesis of 9,-dimethyl-9H-fluoren-2-amine (abbreviation: dmmtBuBiAF) Let's explain the method. The structure of dmmtBuBiAF is shown below.

[0479] [ka]

[0480] <Step 1: 3',5'-Diter-butyl-4-chloro-1,1'-biphenyl Synthesis of > The synthesis was carried out in the same manner as in step 1 of synthesis example 6 in Example 6.

[0481] <Step 2: N,N-bis(3',5'-dether-butyl-1,1'-biphenyl) Lu-4-yl)-9,9,-dimethyl-9H-fluoren-2-amine (abbreviation: dmmt) (BuBiAF) synthesis > 2.8g (13.5ml) of 9,9-dimethyl-9H-fluoren-2-amine in a three-necked flask. mol), 3',5'-ditter-butyl-4-chloro-1 obtained in step 1, 1'-Biphenyl 6.1g (20.3 mmol), sodium tert-butoxide 5 Add 0.8g (60.8mmol) and 70mL of xylene, degass under reduced pressure, and then... The inside of the lasco was purged with nitrogen. This mixture was heated and stirred to approximately 50°C. Here, allyl chloride was added. Palladium dimer(II) (abbreviation: [(Allyl)PdCl]2) 100 mg (0.2 7 mmol), di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl ) Add 381 mg (1.08 mmol) of phosphine (abbreviation: cBRIDP(registered trademark)) It was heated at 120°C for about 3 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was collected by silica gel column chromatography. It was purified by chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and the mixture was concentrated under reduced pressure to obtain an ethanol suspension. At approximately 20°C The precipitate is filtered, and the resulting solid is dried under reduced pressure at approximately 80°C to obtain the target white solid. It was obtained in 0.2g with a yield of 42%. The synthesis scheme for Step 2 is shown in the following equation.

[0482] [ka]

[0483] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The 1H-NMR chart is shown in Figure 32. This indicates the synthesis. In the example, N,N-bis(3',5'-ditter-butyl-1,1'-biphenyl -4-yl)-9,9,-dimethyl-9H-fluoren-2-amine (abbreviation: dmmtB) It was confirmed that uBiAF could be synthesized.

[0484] 1 H-NMR.δ(CDCl3):7.66(d,1H,J=7.5Hz),7.62( d,1H,J=8.0Hz),7.51(d,4H,J=8.5Hz),7.38-7. 44(m,7H),7.26-7.35(m,3H),7.20-7.25(m,4H) ,7.13(dd,1H,J=8.0Hz,1.5Hz),1.45(s,6H),1. 39 (s, 36H).

[0485] Next, 4.0 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 260°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 18.8 mL / min. The process was carried out. After sublimation purification, 2.8 g of a slightly yellowish-white solid was obtained with a recovery rate of 70%.

[0486] Next, the ultraviolet-visible absorption spectrum of dmmtBuBiAF in a toluene solution (hereinafter simply referred to as "absorption") The absorption spectrum (also known as the "absorption spectrum") and emission spectrum were measured. For measuring the absorption spectrum, violet light was used. An external-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) was used to measure the emission spectrum. Both measurements were performed at room temperature using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics Ltd.). A quartz cell was used for the measurement. The obtained absorption spectrum and emission spectrum were then measured. The measurement results for the culvert are shown in Figure 33. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The absorption intensity shown in Figure 33 is obtained from the absorption spectrum measured by placing a toluene solution in a quartz cell. The results shown are obtained by subtracting the absorption spectrum measured with only toluene placed in a quartz cell. ru.

[0487] As shown in Figure 33, the organic compound dmmtBuBiAF has an emission peak at 351 nm. They were doing it.

[0488] Next, we analyze the organic compound, dmmtBuBiAF, using liquid chromatography-mass spectrometry (Liquid Chromatography Mass Spectrometry (Abbreviation: LC / Mass (MS) analysis was performed using MS analysis.

[0489] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C4 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves dmmtBuBiAF of any concentration in toluene and dilutes it with acetonitrile. The amount was adjusted and the injection volume was set to 5.0 μL.

[0490] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0491] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=737 component is ionized in the collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 50 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 34 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0492] From the results in Figure 34, dmmtBuBiAF primarily produces products around m / z = 738. It was found that ions were detected. Note that the results shown in Figure 34 are for dmmtBuBiAF Since it shows characteristic results derived from dmmtBuB in the mixture, This can be considered important data for identifying iAFs.

[0493] The flag m / z=473 was observed when measured at a collision energy of 50eV. The ment ion is generated when the CN bond of dmmtBuBiAF is cleaved, and it has an N-(3' ,5'-Di-tert-butyl-1,1'-biphenyl-4-yl)-N-(9,9-di Presumed to be (methyl-9H-fluoren-2-yl)amine, a characteristic of dmmtBuBiAF is one of them.

[0494] Also, Fig. 88 shows the results of measuring the refractive index of dmmtBuBiAF using a spectroscopic ellipsometer (M-2000U manufactured by J. A. Woollam Japan Co., Ltd.). For the measurement, a film with each layer of material vapor-deposited to a thickness of about 50 nm on a quartz substrate by vacuum evaporation was used. In the figure, n, Ordinary, the refractive index of the ordinary ray, and n, Ext ra-ordinary, the refractive index of the extraordinary ray, are described.

[0495] From this figure, it can be seen that dmmtBuBiAF has an ordinary refractive index in the range of 1.50 or more and 1.75 or less throughout the blue light emission region (455 nm or more and 465 nm or less), and also has an ordinary refractive index at 633 nm in the range of 1.45 or more and 1.70 or less, indicating that it is a material with a low refractive index. was found.

[0496] Next, the Tg of dmmtBuBiAF was measured. Tg was measured using a differential scanning calorimeter (PYRIS1DSC manufactured by PerkinElmer Japan Co., Ltd.) with the powder placed in an aluminum cell. As a result, the Tg of dmmtBuBiAF was 120 °C.

Example

[0497] ≪Synthesis Example 8≫ In this example, the synthesis method of the organic compound shown as Structural Formula (107) in Embodiment 1, N-( 3,5-ditert-butylphenyl)-N-(3’,5’-ditert-butyl -1,1’-biphenyl-4-yl)-9,9-dimethyl-9H-fluorene-2-a mine (abbreviation: mmtBuBimmtBuPAF) will be described. mmtB​ The structure of uBimmtBuPAF is shown below.

[0498] [ka]

[0499] <Step 1: 3',5'-Diter-butyl-4-chloro-1,1'-biphenyl Synthesis of > The synthesis was carried out in the same manner as in step 1 of synthesis example 6 in Example 6.

[0500] <Step 2: N-(3',5'-Ditter-butyl-1,1'-biphenyl-4- Synthesis of (yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)amine 2.8g (13.5ml) of 9,9-dimethyl-9H-fluoren-2-amine in a three-necked flask. mol), 3',5'-ditter-butyl-4-chloro-1 obtained in step 1, 1'-Biphenyl 6.1g (20.3 mmol), sodium tert-butoxide 5 Add 0.8g (60.8mmol) and 70mL of xylene, degass under reduced pressure, and then... The inside of the lasco was purged with nitrogen. This mixture was heated and stirred to approximately 50°C. Here, allyl chloride was added. Palladium dimer(II) (abbreviation: [(Allyl)PdCl]2) 100 mg (0.2 7 mmol), di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl ) Add 381 mg (1.08 mmol) of phosphine (abbreviation: cBRIDP(registered trademark)) It was heated at 120°C for about 3 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was collected by silica gel column chromatography. It was purified by chromatography. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the toluene solution, and the mixture was concentrated under reduced pressure to obtain an ethanol suspension. At approximately 20°C The precipitate is filtered, and the resulting solid is dried under reduced pressure at approximately 80°C to obtain a brownish oily substance containing N- (3',5'-Diter-butyl-1,1'-biphenyl-4-yl)-N-(9, 2.9 g of 9-dimethyl-9H-fluoren-2-yl)amine was obtained in a yield of 46%. The synthesis scheme for step 2 is shown in the following equation.

[0501] [ka]

[0502] <Step 3: N-(3,5-Ditermylbutylphenyl)-N-(3',5',- Ditase-butyl-1,1'-biphenyl-4-yl)-9,9,-dimethyl-9H Synthesis of fluorene-2-amine (abbreviation: mmtBuBimmtBuPAF) In a three-necked flask, the N-(3',5'-ditter-butyl-1, obtained in step 2 1'-biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl) ) 2.7g (5.7mmol) amine, 3,5-diter-butyl-1-bromobene Zen 1.5g (5.7 mmol), sodium tert-butoxide 1.6g (17. Add 0 mmol) and 30 mL of xylene, degas under reduced pressure, and then nitrify the flask. The mixture was substituted with an element. This mixture was heated and stirred to approximately 50°C. Here, di-palladium allyl chloride was added. Merged (II) (abbreviation: [(Allyl)PdCl]2) 21 mg (0.057 mmol) Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine Add 73 mg (0.208 mmol) of (abbreviation: cBRIDP(registered trademark)) and heat at 120°C. It was heated for about 7 hours. After that, the flask temperature was returned to about 60°C, and about 1 mL of water was added. The precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was subjected to silica gel column chromatography. It was purified using a filtration system. The resulting solution was concentrated to obtain a concentrated toluene solution. Ethanol was added to the liquid and concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at approximately 20°C. The mixture was then dried under reduced pressure at approximately 80°C to obtain 3.6 g of the target white solid, yielding a yield of 3.6 g. It was obtained with 95% accuracy. The synthesis scheme for Step 3 is shown in the following equation.

[0503] [ka]

[0504] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 ( 1 Analysis results by H-NMR The results are shown below. Also, 1 The H-NMR chart is shown in Figure 35. From this, it can be seen that the synthesis example is In this case, N-(3,5-ditter-butylphenyl)-N-(3',5',-ditter (Sharrybutyl-1,1'-biphenyl-4-yl)-9,9,-dimethyl-9H-flu It was found that olen-2-amine (abbreviation: mmtBuBimmtBuPAF) could be synthesized. .

[0505] 1 H-NMR.δ(CDCl3):7.64(d,1H,J=7.5Hz),7.57( d,1H,J=8.0Hz),7.48(d,2H,J=8.0Hz),7.43(m, 2H),7.39(m,2H),7.31(td,1H,J=6.0Hz,1.5Hz) ,7.15-7.25(m,4H),6.97-7.02(m,4H),1.42(s, 6H), 1.38(s,18H), 1.25(s,18H).

[0506] Next, 3.2 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 210°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 19.3 mL / min. The process was carried out. After sublimation purification, 3.0 g of a slightly yellowish-white solid was obtained with a recovery rate of 94%.

[0507] Next, the ultraviolet-visible absorption spectrum of the toluene solution of mmtBuBimmtBuPAF (see below) The absorption spectrum (simply called the "absorption spectrum") and emission spectrum were measured. For the determination, an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) was used to analyze the emission spectrum. For the measurements, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used, and both measurements were taken at room temperature. Measurements were performed using a quartz cell. The obtained absorption spectrum and The measurement results of the emission spectrum are shown in Figure 36. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. This represents the degree. The absorption intensity shown in Figure 36 is measured by placing a toluene solution in a quartz cell. The result obtained by subtracting the absorption spectrum measured with only toluene in a quartz cell from the cult. This indicates that.

[0508] As shown in Figure 36, the organic compound mmtBuBimmtBuPAF emits light at 362 nm. It had a peak.

[0509] Next, the organic compound mmtBuBimmtBuPAF was analyzed by liquid chromatography-mass spectrometry (L iquid chromatography mass spectrometry (abbreviation) Mass (MS) analysis was performed using LC / MS analysis.

[0510] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C4 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. Pull dissolves mmtBuBimmtBuPAF at any concentration in toluene, and acetonitrile The solution was diluted and prepared, and the injection volume was 5.0 μL.

[0511] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0512] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the m / z=661 component is ionized in a collision cell using argon gas. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 50 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 37 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0513] From the results in Figure 37, mmtBuBimmtBuPAF is mainly around m / z = 662. Product ions were detected. Note that the results shown in Figure 37 are mmtBu Since it shows characteristic results derived from BimmtBuPAF, it is contained in the mixture. This can be considered important data for identifying the mmtBuBimmtBuPAF that is produced.

[0514] The flag for m / z=397 was observed when measured at a collision energy of 50eV. The ment ion is generated when the CN bond of mmtBuBimmtBuPAF is cleaved. N-(3,5-Diter-butylbenzene-1-yl)-N-(9,9-dimethyl- It is presumed to be 9H-fluoren-2-yl)amine, and the characteristics of mmtBuBimmtBuPAF It is one of the signs.

[0515] Furthermore, Figure 89 shows the refractive index of mmtBuBimmtBuPAF using a spectroscopic ellipsometer (Ge The results of measurements using the M-2000U (manufactured by A. Woolam Japan Co., Ltd.) are shown below. For this, a film was used in which each layer of material was deposited on a quartz substrate by vacuum deposition, with a thickness of approximately 50 nm. Oh, the diagram shows n, the refractive index of ordinary light, and n, the refractive index of extraordinary light. Extraordinary was noted.

[0516] From this figure, mmtBuBimmtBuPAF is in the blue emission region (455nm and above, 465nm and above). The entire region (below m) has a normal refractive index in the range of 1.50 to 1.75, and also at 633nm. The refractive index in this material is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. I found out.

[0517] Next, the Tg of mmtBuBimmtBuPAF was measured. Tg was measured using a differential scanning calorimetry system. Using a PerkinElmer Japan PYRIS1DSC, powder is placed in an aluminum cell. The end was placed on top and measured. As a result, the Tg of mmtBuBimmtBuPAF was 101℃. . [Examples]

[0518] ≪Synthesis Example 9≫ In this embodiment, the organic compound shown as structural formula (108) in Embodiment 1, N,N -Bis(4-cyclohexylphenyl)-9,9-dipropyl-9H-fluorene-2- This document describes the synthesis method of amine (abbreviation: dchPAPrF). The construction is shown below.

[0519] [ka]

[0520] <Step 1: Synthesis of 2-bromo-9,9-dipropyl-9H-fluorene> Place 24.5g (100 mmol) of 2-bromo-9H-fluorene into a three-necked flask, The inside of the flask was depressurized and then purged with nitrogen. Sodium-tert-butyric acid was added to this flask. Add 28.8g (300mmol) of side and 500mL of anhydrous dimethyl sulfoxide, and stir. This flask was heated to approximately 95°C. 37.4g of 1-iodopropane was added to this mixture. The mixture was added dropwise (220 mmol) and allowed to react. This mixture was then cooled by air for approximately 14 minutes. The mixture was stirred for a certain amount of time. After cooling, 500 mL each of toluene and water were added to the mixture and stirred. Mixed. This mixture was separated into an organic layer and an aqueous layer. To the resulting aqueous layer, approximately 500 mL of toluene was added. Add the extract and separate the liquid. Repeat this process twice. Mix the resulting organic layer with the extract and add water. The mixture was washed and separated. This was repeated twice. Magnesium sulfate was added to the resulting organic layer. The water was dried and the solution was concentrated. The resulting solution was purified by silica gel column chromatography. The obtained solution was concentrated and dried under vacuum. 23.8 g of the target white solid was obtained. The yield was 72%. The synthesis scheme for Step 1 is shown in the following equation.

[0521] [ka]

[0522] <Step 2: Synthesis of 4-cyclohexylaniline> The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 3 in Example 3.

[0523] Step 3: N-(4-cyclohexylphenyl)-N-(9,9-dipropyl-9H Synthesis of fluoren-2-yl)amine The 2-bromo-9,9-dipropyl-9H-fluore obtained in Step 1 is placed in a three-necked flask. 11.0 g (33.3 mmol), 4-cyclohexylaniline obtained in step 2. 5.8g (33.3 mmol), sodium tert-butoxide 9.6g (100 ml) A mole of xylene was added, and the flask was depressurized and purged with nitrogen. 170 mL of xylene was added to this flask. After adding the mixture and degassing it under reduced pressure, the flask was purged with nitrogen. This mixture was then heated to approximately 50°C. It was heated and stirred until it reached this point. Here, allyl palladium chloride dimer(II) (abbreviated as [(Ally l)PdCl]2) 122 mg (0.33 mmol), di-tert-butyl (1-methicone) (2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP (registered trademark)) 547 mg (1.33 mmol) was added, and this mixture was heated at 90°C for approximately 3 hours. Then, the flask temperature was returned to approximately 60°C, approximately 2 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was purified by silica gel column chromatography. The solution was concentrated to obtain a concentrated toluene solution. This toluene solution was then heated under vacuum at approximately 40°C. The product was dried under reduced pressure to obtain 9.1 g of the target brown oily substance in a yield of 64%. Step 3 The scheme is shown in the following equation.

[0524] [ka]

[0525] <Step 4: N,N-bis(4-cyclohexylphenyl)-9,9-dipropyl-9 Synthesis of H-fluoren-2-amine (abbreviation: dchPAPrF) In a three-necked flask, place the N-(4-cyclohexylphenyl)-N-(9, obtained in step 3) into a three-necked flask. 9-Dipropyl-9H-Fluoren-2-yl)amine 4.2g (10 mmol), 1- Bromo-4-cyclohexylbenzene 2.4g (10 mmol), sodium tert - Add 2.9g (30 mmol) of butoxide and 50mL of xylene, and degas under reduced pressure. Afterward, the flask was purged with nitrogen. This mixture was heated and stirred to approximately 50°C. Here, Allyl palladium chloride dimer (II) (abbreviation: [(Allyl)PdCl]2) 37 mg (0.10 mmol), di-tert-butyl(1-methyl-2,2-diphenylcyclo Propylphosphine (abbreviation: cBRIDP(registered trademark)) 141 mg (0.40 mmol) l) was added, and this mixture was heated at 100°C for about 3 hours. After that, the temperature of the flask was The solution was returned to approximately 60°C, approximately 2 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solid was obtained. The solution was purified by silica gel column chromatography. The resulting solution was concentrated, and a concentrated solution was obtained. A toluene solution was obtained. Ethanol was added to this toluene solution, and it was concentrated under reduced pressure to form an ethanol suspension. A turbid liquid was obtained. The precipitate was filtered at approximately 20°C, and the resulting solid was dried under reduced pressure at approximately 80°C. 4.7 g of the target substance, a white solid, was obtained in a yield of 81%. The synthesis scheme for Step 4 is given by the following equation. show.

[0526] [ka]

[0527] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 4 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The H-NMR chart is shown in Figure 38. In the example, N,N-bis(4-cyclohexylphenyl)-9,9-dipropyl-9 It was found that H-fluoren-2-amine (abbreviated as dchPAPrF) could be synthesized.

[0528] 1 H-NMR.δ(CDCl3):7.58(m,1H),7.51(d,1H,J=8 .0Hz),7.28(t,2H,J=7.5Hz),7.19-7.24(m,1H) ,7.11(d,1H,J=1.5Hz),7.00-7.19(m,8H),6.97 (dd,1H,J=8.0Hz,1.5Hz),2.40-2.50(brm,2H), 1.70-1.94(m,14H),1.33-1.46(m,8H),1.18-1. 30 (brm, 2H), 0.60-0.78 (m, 10H).

[0529] Next, 4.0 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 225°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 19.0 mL / min. The process was carried out. After sublimation purification, 3.1 g of a slightly yellowish-white solid was obtained with a recovery rate of 77%.

[0530] Next, the ultraviolet-visible absorption spectrum of dchPAPrF in a toluene solution (hereinafter simply referred to as "absorption spectrum") The "spectrum" (also known as the emission spectrum) and emission spectrum were measured. For measuring the absorption spectrum, ultraviolet light was used. Using a visual spectrophotometer (V550 model, manufactured by JASCO Corporation), the emission spectrum was measured using fireflies. Both measurements were performed at room temperature using a photophotometer (FS920, manufactured by Hamamatsu Photonics Ltd.). Furthermore, a quartz cell was used for the measurement. The obtained absorption spectrum and emission spectrum The measurement results are shown in Figure 39. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Figure 3 The absorption intensity shown in 9 is obtained from the absorption spectrum measured by placing a toluene solution in a quartz cell. This shows the result after subtracting the absorption spectrum measured by placing only Luen in a quartz cell.

[0531] As shown in Figure 39, the organic compound dchPAPrF has an emission peak at 355 nm. there was.

[0532] Next, the organic compound was analyzed using liquid chromatography-mass spectrometry (Liquid C) on dchPAPrF. chromatography mass spectrometry (abbreviation: LC / MS) Mass (MS) analysis was performed.

[0533] LC / MS analysis uses LC (liquid chromatography) separation with Waters Acqui. ty UPLC® allows MS analysis (mass spectrometry) to be performed using Waters Xevo The separation was performed using G2 Tof MS. The column used for LC separation was Acquity UPL. A C BEH C4 column (2.1 × 100 mm, 1.7 μm) was used, and the column temperature was set to 40°C. The mobile phase consisted of acetonitrile as mobile phase A and a 0.1% formic acid aqueous solution as mobile phase B. The pull is prepared by dissolving dchPAPrF of any concentration in toluene and diluting it with acetonitrile. The solution was adjusted, and the injection volume was set to 5.0 μL.

[0534] LC separation is defined as the ratio of mobile phase A to mobile phase B from 0 to 10 minutes after the start of measurement, where mobile phase A: The mobile phase B was set to 95:5.

[0535] MS analysis uses electrospray ionization. Ionization was performed using ionization (abbreviated as ESI). The capillary voltage at this time was 3 The sample cone voltage was set to 0.0kV, and detection was performed in positive mode. Under these conditions, the ionized m / z=581 component is subjected to argon gas in the collision cell. It was collided with a argon atom to dissociate it into product ions. The energy used when colliding with argon ( The collision energy was set to 50 eV. The mass range measured was m / z (mass charge). The ratio was set to 100-1500. Figure 40 shows the dissociated product ions with a time of flight (T The results detected by the OF) type MS are shown.

[0536] From the results in Figure 40, dchPAPrF is mainly product io around m / z = 582. It was found that n was detected. Note that the results shown in Figure 40 are derived from dchPAPrF. The results exhibit characteristic properties, allowing for the identification of dchPAPrF contained in the mixture. This can be considered important data for that purpose.

[0537] The flag m / z=423 was observed when measured at a collision energy of 50eV. The ment ion is formed when the CN bond of dchPAPrF is cleaved, resulting in an N-(4-cyclic ion). Rohexylphenyl)-N-(9,9-dipropyl-9H-fluoren-2-yl)amide This is presumed to be one of the characteristics of dchPAPrF.

[0538] Furthermore, Figure 90 shows the refractive index of dchPAPrF measured with a spectroscopic ellipsometer (J.A.W. The results of measurements taken using a Ram Japan M-2000U are shown. A quartz substrate was used for the measurements. A film was used on top, in which each layer of material was deposited by vacuum deposition to a thickness of approximately 50 nm. Note that the figure is not shown. n, Ordinary, is the refractive index of a ray, and n, Extra, is the refractive index of an extraordinary ray. -ordinary was written.

[0539] From this figure, dchPAPrF is observed throughout the entire blue emission region (455nm to 465nm). The ordinary refractive index is in the range of 1.50 to 1.75, and the ordinary refractive index at 633 nm is... The refractive index was also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. . [Examples]

[0540] ≪Synthesis Example 10≫ In this example, the organic compound shown as structural formula (109) in Embodiment 1, N-[ (3',5'-dicyclohexyl)-1,1'-biphenyl-4-yl]-N-(4-cy Chlohexylphenyl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: m This section describes the synthesis method of mchBichPAF. The structure of mmchBichPAF is described below. The following is shown.

[0541] [ka]

[0542] <Step 1: Synthesis of 3,5-dicyclohexyl-1-methoxybenzene> 36.3 g (137 mmol) of 3,5-dibromo-1-methoxybenzene in a three-necked flask. The flask was then depressurized and subsequently purged with nitrogen. 1000mL, Tris(dibenzylideneacetone)dipalladium(0) 1.88g (2. 0.5 mmol), 2-(dicyclohexylphosphino)-2',4',6'-triisopropyl alcohol Add 1.95g (4.10 mmol) of ropilbiphenyl (abbreviation: XPhos), and approximately 65 It was heated to °C. 30 ml of a 1.0 M solution of cyclohexyl magnesium bromide was added to this mixture. The mixture was added dropwise and allowed to react. After cooling, the mixture was stirred at room temperature for approximately 14 hours. Then, 200 mL of water was added dropwise, and the mixture was separated into an organic layer and an aqueous layer. Then, approximately 500 mL of ethyl acetate was added, and the mixture was extracted, separating into an aqueous layer and an organic layer. This process was repeated twice. The separated organic layers were mixed and washed with saturated sodium bicarbonate solution, separating the aqueous layer from the organic layer. The mixture was separated. Magnesium sulfate was added to the resulting organic layer, and the water was dried and concentrated. The solution was purified by silica gel column chromatography. The resulting solution was concentrated and then vacuum filtered. It was dried. 32.9 g of the target product, a colorless oily substance, was obtained in a yield of 88%. Step 1 The synthesis scheme is shown in the following equation.

[0543] [ka]

[0544] <Step 2: Synthesis of 3,5-dicyclohexylphenol> The 3,5-dicyclohexyl-1-methoxybenzene obtained in Step 1 is placed in a three-necked flask. 32.0 g (117.5 mmol) was added, and the flask was depressurized and purged with nitrogen. 400 mL of dichloromethane was added to the solution and cooled to -20°C. Boron tribromide was added to this solution. 123 mL (123 mmol) of plain 1.0 M dichloromethane solution was added dropwise. The mixture was heated to room temperature and stirred at room temperature for approximately 14 hours. Approximately 200 ml of tap water was added to this mixture. L was added, and the mixture was separated into an organic layer and an aqueous layer. Approximately 200 mL of dichloromethane was added to the resulting aqueous layer. The mixture was extracted and separated. The two resulting organic layers were mixed and saturated with sodium bicarbonate. The mixture was washed with an aqueous solution and separated. Magnesium sulfate was added to the resulting organic layer, and the water was dried. The solution was filtered. The resulting dichloromethane solution was concentrated and subjected to silica gel column chromatography. - It was purified. The resulting solution was concentrated to obtain a colorless oil. This oil was then processed under vacuum for approximately The mixture was dried at 40°C to obtain 26.0 g of the target product, a colorless oily substance, in a yield of 86%. The synthesis scheme for P2 is shown in the following equation.

[0545] [ka]

[0546] Step 3: Mix trifluoromethanesulfonic acid-3,5-dicyclohexylbenzene > The 3,5-dicyclohexyl-1-methoxybenzene obtained in Step 1 is placed in a three-necked flask. 32.0 g (117.5 mmol) was added, and the flask was depressurized and purged with nitrogen. 400 mL of dichloromethane was added to the solution and cooled to -20°C. Trifluor 37.0 g (131 mmol) of lomethanesulfonic acid anhydride was added dropwise. This mixture The mixture was heated to room temperature and stirred at room temperature for approximately 14 hours. Approximately 200 mL of water was added to this mixture. The mixture was separated into an organic layer and an aqueous layer. Approximately 200 mL of dichloromethane was added to the resulting aqueous layer and extracted. The two organic layers obtained by the separation were mixed and treated with saturated sodium bicarbonate aqueous solution. The mixture was washed and separated. Magnesium sulfate was added to the resulting organic layer, the water was dried, and the mixture was filtered. The obtained dichloromethane solution was concentrated and purified by silica gel column chromatography. The obtained solution was concentrated to obtain a colorless oily substance. This oily substance was dried under vacuum at approximately 60°C. This yielded 33.4 g of the target product, a colorless oily substance, in a yield of 85%. Step 3 Synthesis Chiem is shown in the following equation.

[0547] [ka]

[0548] <Step 4: Compound 3',5'-dicyclohexyl-4-chloro-1,1'-biphenyl > 9g of trifluoromethanesulfonic acid-3,5-dicyclohexylbenzene in a three-necked flask. 8g (25mmol), 4-chlorophenylboronic acid 4.3g (27.5mmol), charcoal 8.8g sodium phosphate (82.5 mmol), 125mL 1,4-dioxane, 4ml tap water After adding 1 mL and degassing under reduced pressure, the flask was purged with nitrogen. To this mixture, Palladium acetate 112 mg (0.50 mmol), triphenylphosphine 266 mg ( (1.0 mmol) was added, and the mixture was heated at 50°C for approximately 4 hours. Afterwards, it was left to room temperature. The organic layer and aqueous layer were separated. Magnesium sulfate was added to this solution, and the water was dried to concentrate it. The obtained toluene solution was purified by silica gel column chromatography. The solution was concentrated and allowed to dry. Then, hexane was added and recrystallized. The precipitated white solid was frozen. After cooling, it was filtered. This solid was vacuum-dried at approximately 60°C to obtain the target white solid. 5g was obtained with a yield of 63%. The synthesis scheme for Step 4 is shown in the following equation.

[0549] [ka]

[0550] <Step 5: N-[(3',5'-dicyclohexyl)-1,1'-biphenyl-4- Il]-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene- Synthesis of 2-amine (abbreviation: mmchBichPAF) In a three-necked flask, place the 3',5'-dicyclohexyl-4-chloro-1 obtained in step 4 into a three-necked flask. 3.5 g (10.0 mmol) of 1'-biphenyl, and 3,5-disic synthesized in step 2. Lohexylphenol 3.7g (10.0 mmol), sodium-tert-butoxy Add 2.9g (30.0 mmol) of xylene and 50mL of xylene, then degass under reduced pressure. The flask was then purged with nitrogen. This mixture was heated and stirred to approximately 50°C. Here, allyl Palladium chloride dimer(II) (abbreviation: [(Allyl)PdCl]2) 37 mg (0. 10 mmol), di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl) Phosphine (abbreviation: cBRIDP(registered trademark)) 141 mg (0.40 mmol) In addition, this mixture was heated at 100°C for approximately 3 hours. After that, the temperature of the flask was reduced to approximately 60°C. The solution was returned to °C, approximately 2 mL of water was added, and the precipitated solid was filtered off. The filtrate was concentrated, and the resulting solution was obtained. The solution was purified by silica gel column chromatography. The resulting solution was concentrated and then concentrated True A toluene solution was obtained. Ethanol was added to this toluene solution, and the solution was concentrated under reduced pressure to obtain an ethanol suspension. The precipitate was filtered at approximately 20°C, and the resulting solid was dried under reduced pressure at approximately 80°C to obtain the target substance. A white solid was obtained in 6.0 g with a yield of 88%. Step 5: mmchBichPAF The scheme is shown in the following equation.

[0551] [ka]

[0552] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 5 above ( 1 (H-NMR) The analysis results are shown below. Also, 1 The 1H-NMR chart is shown in Figure 41. From this, we can see the results of this synthesis. In the example, N-[(3',5'-dicyclohexyl)-1,1'-biphenyl-4-i [L]-N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluorene-2 -It was found that the amine (abbreviated as mmchBichPAF) could be synthesized.

[0553] 1 H-NMR.δ(CDCl3):7.63(d,1H,J=7.5Hz),7.57( d,1H,J=8.5Hz),7.46(d,2H,J=8.5Hz),7.39(d, 1H,J=7.5Hz),7.31(td,1H,J=7.5Hz,1.5Hz),7. 21-7.28(m,4H),7.07-7.18(m,6H),7.02-7.06( m,1H),7.01(s,1H),2.44-2.57(brm,3H),1.89- 1.96(m,6H),1.81-1.88(m,6H),1.71-1.78(m,3 H),1.34-1.53(m,18H),1.20-1.32(m,3H).

[0554] Next, 5.0 g of the obtained solid was purified by sublimation using the train sublimation method. The manufacturing process involved heating at 270°C under conditions of a pressure of 3.0 Pa and an argon flow rate of 19.8 mL / min. The process was carried out. After sublimation purification, 3.5 g of a slightly yellowish-white solid was obtained with a recovery rate of 70%.

[0555] Next, the ultraviolet-visible absorption spectrum of mmchBichPAF (hereinafte...

Claims

1. An organic compound represented by the following general formula (G1). 【Chemistry 1】 (In the above general formula (G1), Ar1 and Ar2 each independently represent a biphenyl group or a terphenyl group. However, one or both of Ar1 and Ar2 have one or more C1 to C12 hydrocarbon groups (excluding adamantyl groups) in which the carbon atoms form bonds only in sp3 hybrid orbitals, the total number of carbon atoms in all of the hydrocarbon groups bonded to Ar1 and Ar2 is 8 or more, and the total number of carbon atoms in the hydrocarbon groups bonded to either Ar1 or Ar2 is 6 or more. Note that if Ar1 or Ar2 has multiple C1 to C2 linear alkyl groups as the hydrocarbon groups, these linear alkyl groups may be bonded to each other to form a ring. In one or both of Ar1 and Ar2, the benzene ring bonded to nitrogen is unsubstituted. R1 and R2 each independently represent a C1 to C4 alkyl group. Note that R R1 and R2 may be bonded to each other to form a ring. R3 represents an alkyl group having 1 to 4 carbon atoms, and u is an integer from 0 to 4. The hydrocarbon group is either an alkyl group having 3 to 8 carbon atoms or a monocyclic cycloalkyl group having 6 to 12 carbon atoms.

2. An organic compound represented by the following general formula (G1). 【Chemistry 2】 (In the above general formula (G1), Ar1 and Ar2 each independently represent a biphenyl group or a terphenyl group. However, one or both of Ar1 and Ar2 have one or more C1 to C12 hydrocarbon groups (excluding adamantyl groups) in which the carbon atoms form bonds only in sp3 hybrid orbitals, the total number of carbon atoms in all of the hydrocarbon groups bonded to Ar1 and Ar2 is 8 or more, and the total number of carbon atoms in the hydrocarbon groups bonded to either Ar1 or Ar2 is 6 or more. Note that if Ar1 or Ar2 has multiple C1 to C2 linear alkyl groups as the hydrocarbon groups, these linear alkyl groups may be bonded to each other to form a ring. In one or both of Ar1 and Ar2, the benzene ring bonded to nitrogen is unsubstituted. R1 and R2 each independently represent a C1 to C4 alkyl group. Note that R R1 and R2 may be bonded to each other to form a ring. R3 represents an alkyl group having 1 to 4 carbon atoms, and u is an integer from 0 to 4. The hydrocarbon group is one of the following: an alkyl group having 3 to 8 carbon atoms, a cyclohexyl group, a 4-methylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a decahydronaphthyl group, a cycloundecyl group, and a cyclododecyl group.

3. In claim 1 or claim 2, An organic compound in which the proportion of carbon atoms that form bonds solely through sp3 hybrid orbitals is between 23% and 55% of the total number of carbon atoms in the molecule.

4. A light-emitting device having the organic compound according to any one of claims 1 to 3.

5. An electronic device comprising the light-emitting device described in claim 4, and a sensor, an operation button, a speaker, or a microphone.

6. A light-emitting device comprising the light-emitting device described in claim 4 and a transistor or substrate.

7. A lighting device having a light-emitting device according to claim 4 and a housing.

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