organic compounds

Abstract

To provide novel organic compounds, or organic compounds that exhibit good chromatic luminescence. To provide. Or, to provide an organic compound that exhibits blue light emission with good chromaticity. Or, to provide light emission To provide organic compounds with good efficiency, or to provide organic compounds with high carrier transport properties. To provide reliable organic compounds. [Solution] Substituted or unsubstituted naphthobisbenzofuran skeleton, substituted or unsubstituted naphthobisbenzofuran skeleton Tobisbenzothiophene skeleton and substituted or unsubstituted naphthobenzofuranosebenzothiophene One of the benzofuranyl skeletons has a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzofuranyl group. A dibenzothiophenyl group and one of either a substituted or unsubstituted carbazolyl group are bonded together. The present invention provides an organic compound having at least one amino group.

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound and a light-emitting element using the organic compound, a display module This relates to modules, lighting modules, display devices, light-emitting devices, electronic equipment, and lighting devices. One aspect of the present invention is not limited to the above-described technical field. The technical field relates to products, methods, or methods of manufacture. Or, an embodiment of the present invention. The term refers to a process, machine, manufacture, or composition. This relates to matter. Therefore, one aspect of the present invention disclosed more specifically herein The technical fields include semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, and storage devices. Examples include electrical devices, memory devices, imaging devices, methods for driving them, or methods for manufacturing them. It can be listed as follows. [Background technology]

[0002] Display devices and light-emitting devices using organic EL elements have been partially put into practical use, and their applications are expanding. With LCD displays making great progress these days, the next generation of displays is said to be... Naturally, high quality is required for OLED displays.

[0003] Various materials have been developed for use in organic EL displays, but they are not yet practical. There aren't many substances that possess such properties. Also, the diversity of combinations, Considering compatibility and other factors, it's undeniable that having more options is always better.

[0004] Organic EL elements have a functional separation configuration in which multiple functions are handled by different materials. However, among these, in order to improve the luminescent material, especially the luminous efficiency which affects power consumption, and the display quality, There is a great demand for specific colors of light emission.

[0005] Patent Document 1 discloses an organic compound having a naphthobisbenzofuran skeleton. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2014-237682 [Overview of the project] [Problems that the invention aims to solve]

[0007] One aspect of the present invention aims to provide a novel organic compound, or a compound with good color. The objective is to provide an organic compound that exhibits a certain degree of luminescence, or a blue luminescence with good chromaticity. The objective is to provide organic compounds that emit light, or organic compounds with good luminescence efficiency. The purpose is to provide a product, or to provide an organic compound with high carrier transport properties. The objective is to provide reliable organic compounds.

[0008] Furthermore, one aspect of the present invention aims to provide a novel light-emitting element. The objective is to provide a light-emitting element with good efficiency, or a light-emitting element with good chromaticity. The objective is to provide a light-emitting element that emits blue light with good chromaticity. The objective is to provide a light-emitting element with a good lifespan. The objective is to provide a light-emitting element with a low driving voltage.

[0009] Alternatively, another aspect of the present invention relates to a light-emitting device, electronic device, and display device with low power consumption. Each is intended to provide. Alternatively, in another aspect of the present invention, a highly reliable light-emitting device The purpose is to provide a device, electronic equipment, and display device, respectively. Or, another aspect of the present invention. The aim is to provide light-emitting devices, electronic devices, and display devices with high display quality. do.

[0010] The present invention only needs to solve one of the above-mentioned problems. [Means for solving the problem]

[0011] One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0012] [ka]

[0013] However, in the formula, B is a substituted or unsubstituted naphthobisbenzofuran skeleton, substituted or unsubstituted Naphthobisbenzothiophene skeleton and substituted or unsubstituted naphthobenzofuranosethiophene It represents one of the offensive skeletons. Also, Ar 1 These are substituted or unsubstituted carbon atoms with 6 to 25 carbon atoms. Aromatic hydrocarbon groups, substituted or unsubstituted dibenzoflonyl groups, substituted or unsubstituted diben It is either a zothiophenyl group or a substituted or unsubstituted carbazolyl group. A is set Substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, It is either a substituted or unsubstituted carbazolyl group, α 1 ~ α 3 Each is independent It is a divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, either substituted or unsubstituted. Also, l, m n independently represents an integer between 0 and 2, and q is either 1 or 2.

[0014] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0015] [ka]

[0016] However, in the formula, B is a substituted or unsubstituted naphthobisbenzofuran skeleton, or a substituted or unsubstituted naphthobisbenzofuran skeleton. Phthobisbenzothiophene skeleton and substituted or unsubstituted naphthobenzofuranosebenzothio It represents one of the Fen skeletons. Also, Ar 1 These are substituted or unsubstituted carbon atoms with 6 to 25 carbon atoms. Aromatic hydrocarbon group or any one of the groups represented by the following general formulas (g1) to (g3) Furthermore, A is one of the groups represented by the following general formulas (g1) to (g3). Also, α 1 No To α 3 Each is independently a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms. Furthermore, l, m, and n each independently represent integers from 0 to 2, and q is either 1 or 2. ru.

[0017] [ka]

[0018] In general formulas (g1) to (g3), R 1 ~R 9 In this case, one of them represents a single bond. The remaining atoms are, independently, hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, and a ring having 3 to 10 carbon atoms. The formula represents either a hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms. Yes. However, A is a group represented by the general formula (g3), and the group represented by the general formula (g3) in which R 9 represents a single bond, n shall be 1 or 2. Also, Ar 1 is a group represented by the general formula (g3), and when R 9 represents a single bond in (g3), m shall be 1 or 2.

[0019] Alternatively, another aspect of the present invention is that, in the above configuration, when A and / or Ar 1 are each independently a group represented by the above general formula (g1) or general formula (g2), in the group represented by the general formula (g1) or general formula (g2), any one of R 1 to R 3 is a single bond, and when A and / or Ar are a group represented by the above general formula (g3), in the group represented by the general formula 1 (g3), R or R 2 or R 3 is a single bond, it is an organic compound.

[0020] Alternatively, another aspect of the present invention is that, in the above configuration, the organic compound in which the A is a group represented by the general formula (g1) or the general formula (g3), and R in the group represented by the general formula (g1) or the general formula (g3) 2 represents a single bond.

[0021] Alternatively, another aspect of the present invention is that, in the above configuration, it is an organic compound in which the n is 0 .

[0022] Alternatively, another aspect of the present invention is that, in the above configuration, it is an organic compound in which the Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms.

[0023] Alternatively, another aspect of the present invention is an organic compound in which l is 0 in the above configuration. .

[0024] Alternatively, in another aspect of the present invention, in the above configuration, B is the following general formula (B1) to It is an organic compound whose skeleton is one of the structures represented by general formula (B4).

[0025] [ka]

[0026] However, in the above general formulas (B1) to (B4), X 2 and X 3 Each is independent R represents an oxygen atom or a sulfur atom. In the above general formula (B1), R 10 ~R 21 Either one or two of them represent a single bond, and the remaining ones are each independently hydrogen, carbon atoms with 1 to 1 0 hydrocarbon groups, cyclic hydrocarbon groups with 3 to 10 carbon atoms, substituted or unsubstituted groups with 6 to 10 carbon atoms 14 aromatic hydrocarbon groups, substituted or unsubstituted diarylamino groups having 12 to 32 carbon atoms. It represents one of the following. Also, in the above general formula (B2), R 30 ~R 41 either 1 or 2 represent a single bond, and the remaining ones are independently hydrogen and a hydrocarbon group having 1 to 10 carbon atoms. , cyclic hydrocarbon groups having 3 to 10 carbon atoms, substituted or unsubstituted aromatic carbon groups having 6 to 14 carbon atoms The expression represents either a hydrogenated group or a substituted or unsubstituted diarylamino group having 12 to 32 carbon atoms. In addition, in the above general formula (B3), R 50 ~R 61 One or two of the following are single The bond is represented, and the remaining atoms are independently hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a hydrocarbon group with 3 to 10 carbon atoms. 10 cyclic hydrocarbon groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 14 carbon atoms, substituted Alternatively, it represents any of the following: a diarylamino group having 12 to 32 carbon atoms and no substitution. In the general formula (B4), R 70 ~R 81 Either 1 or 2 of them represents a single bond, and the rest Each of these independently consists of hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, and a cyclic carbon group having 3 to 10 carbon atoms. Hydrogen group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, substituted or unsubstituted This represents any diarylamino group having 12 to 32 carbon atoms.

[0027] Alternatively, in another aspect of the present invention, in the above configuration, B is the general formula (B1) to It is an organic compound whose skeleton is one of the structures represented by general formula (B3).

[0028] Alternatively, in another aspect of the present invention, in the above configuration, B is represented by the following general formula (B1) It is an organic compound that forms a skeleton.

[0029] [ka]

[0030] However, in the formula X 2 and X 3 Each of these independently represents either an oxygen atom or a sulfur atom. Also, R 1 0 ~R 21 In this case, 1 or 2 represent a single bond, and the remaining ones independently represent hydrogen, carbon atoms, and number of atoms. 1 to 10 hydrocarbon groups, cyclic hydrocarbon groups having 3 to 10 carbon atoms, substituted or unsubstituted carbon atoms Aromatic hydrocarbon groups having 6 to 14 carbon atoms, or diaryls having 12 to 32 carbon atoms, substituted or unsubstituted. Represents one of the amino groups.

[0031] Alternatively, in another aspect of the present invention, in the above configuration, R in the general formula (B1) 11 , R 12 , R 17 and R 18 It is an organic compound in which one or two of the following represent a single bond.

[0032] Alternatively, in another aspect of the present invention, in the above configuration, q in the general formula (G1) is 2 Therefore, R in the general formula (B1) 11 or R 12 One of them is a single bond. , R 17 or R 18 It is an organic compound in which one of the bonds is a single bond.

[0033] Alternatively, in another aspect of the present invention, in the above configuration, q in the general formula (G1) is 2 Therefore, R in the general formula (B1) 11 and R 17 It is an organic compound in which the bond is a single bond. ru.

[0034] Alternatively, in another aspect of the present invention, in the above configuration, q in the general formula (G1) is 2 Therefore, R in the general formula (B1) 12 and R 18 It is an organic compound in which the bond is a single bond. ru.

[0035] Alternatively, in another aspect of the present invention, in the above configuration, B is represented by the following general formula (B2) It is an organic compound that forms a skeleton.

[0036] [ka]

[0037] However, in the formula X 2 and X 3Each independently represents an oxygen atom or a sulfur atom. Also, R 3 0 to R 41 One or two of them represent a single bond, and the rest are each independently hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, a cyclic hydrocarbon group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamino group having 12 to 32 carbon atoms. 1 to 10, a cyclic hydrocarbon group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 32 carbon atoms. 6 to 14, a substituted or unsubstituted diarylamino group having 12 to 32 carbon atoms. Any one of the amino groups.

[0038] Or, another aspect of the present invention is an organic compound in which, in the above configuration, one or two of R 31 , R 32 , R 37 and R 38 in the general formula (B2) represent a single bond.

[0039] Or, another aspect of the present invention is an organic compound in which, in the above configuration, q in the general formula (G1) is 2 and one of R 31 or R 32 and one of R 37 or R 38 in the general formula (B2) is a single bond.

[0040] Or, another aspect of the present invention is an organic compound in which, in the above configuration, q in the general formula (G1) is 2 and R 31 and R 37 in the general formula (B2) are single bonds.

[0041] Or, another aspect of the present invention is an organic compound in which, in the above configuration, q in the general formula (G1) is 2 and R 32 and R 38 in the general formula (B2) are single bonds.

[0042] ​​ Alternatively, in another aspect of the present invention, in the above configuration, B is represented by the following general formula (B3) It is an organic compound that forms a skeleton.

[0043] [ka]

[0044] However, in the formula X 2 and X 3 Each of these independently represents either an oxygen atom or a sulfur atom. Also, R 5 0 ~R 61 In this case, 1 or 2 represent a single bond, and the remaining ones independently represent hydrogen, carbon atoms, and number of atoms. 1 to 10 hydrocarbon groups, cyclic hydrocarbon groups having 3 to 10 carbon atoms, substituted or unsubstituted carbon atoms Aromatic hydrocarbon groups having 6 to 14 carbon atoms, or diaryls having 12 to 32 carbon atoms, substituted or unsubstituted. Represents one of the amino groups.

[0045] Alternatively, in another aspect of the present invention, in the above configuration, R in the general formula (B3) 51 , R 52 , R 57 and R 58 It is an organic compound in which one or two of the following represent a single bond.

[0046] Alternatively, in another aspect of the present invention, in the above configuration, q in the general formula (G1) is 2 Therefore, R in the general formula (B3) 51 or R 52 and R 57 or R 58 is It is an organic compound that is a bond.

[0047] Alternatively, in another aspect of the present invention, in the above configuration, q in the general formula (G1) is 2 Therefore, R in the general formula (B3) 51and R 57 is an organic compound in which it is a single bond .

[0048] Alternatively, in another aspect of the present invention, in the above configuration, q in the general formula (G1) is 2 , and R in the general formula (B3) 52 and R 58 is an organic compound in which it is a single bond .

[0049] Alternatively, in another aspect of the present invention, in the above configuration, the X 2 and X 3 are both oxygen atoms is an organic compound.

[0050] Alternatively, in another aspect of the present invention, in the above configuration, A is a group represented by the general formula (g1) is an organic compound.

[0051] Alternatively, in another aspect of the present invention, it is an organic compound represented by the following general formula (G1-1).

[0052] [Chemical formula]

[0053] However, in the above general formula (G1-1), B is a group represented by the following general formula (B1-1) or (B3-1) . Also, Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms , and A is a group represented by the following general formula (g0). Also, m represents an integer of 0 to 2 . Also, α 2 is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 14 carbon atoms​​​​​​​​​​

[0055] However, in the above general formula (B1-1) or (B3-1), X 2 and X 3 each represent independently an oxygen atom or a sulfur atom. Also, R 12 , R 18 , R 52 and R 58 each represent a single bond.

[0056]

Chemical formula

[0057] However, in the above general formula (g0), X0 is an oxygen atom or a nitrogen atom bonded with a substituted or unsubstituted phenyl group. Also, R represents a single bond. 2 represents a single bond.

[0058] Or, another aspect of the present invention is the above-described organic compound having a molecular weight of 1300 or less in the above configuration. compound.

[0059] Or, another aspect of the present invention is an organic compound having a molecular weight of 1000 or less in the above configuration. compound.

[0060] Or, another aspect of the present invention is a light-emitting device including an organic compound having the above configuration.

[0061] Or, another aspect of the present invention is a light-emitting device including an organic compound represented by any one of the following structural formulas (iii), (vii), (ix), (x) , (xi), (xiii), and (xv) to (XXiv). compound.

[0062]

Chemical formula

[0063] [ka]

[0064] [ka]

[0065] One aspect of the present invention comprises a light-emitting element having the above configuration, a transistor, or a substrate. It is a light-emitting device.

[0066] Another aspect of the present invention is a light-emitting device having the above configuration, and a sensor, an operating button, a speaker, Alternatively, it is an electronic device having a microphone.

[0067] Another aspect of the present invention is a lighting device having a light-emitting device having the above configuration and a housing. .

[0068] Alternatively, another aspect of the present invention provides a light-emitting element having the above configuration, a substrate, and a transistor. It is a light-emitting device having the following characteristics.

[0069] Alternatively, another aspect of the present invention provides a light-emitting device having the above configuration, a sensor, an operating button, It is an electronic device that has a speaker or a microphone.

[0070] Alternatively, another aspect of the present invention is a lighting device having the above configuration, and a housing, It is a device.

[0071] Furthermore, the term "light-emitting device" in this specification includes image display devices that use light-emitting elements. , a connector to the light-emitting element, for example, an anisotropic conductive film or TCP (Tape Carrier A module with an er Package attached, and a printed circuit board is installed at the end of the TCP. The module or light-emitting element is equipped with a COG (Chip On Glass) system. Modules with directly mounted ICs (integrated circuits) may also be included in the definition of light-emitting devices. Furthermore, Lighting fixtures and similar devices may contain light-emitting devices. [Effects of the Invention]

[0072] In one aspect of the present invention, a novel organic compound can be provided, or a compound with good chromaticity. It is possible to provide organic compounds that exhibit luminescence, or that exhibit blue light emission with good chromaticity. It is possible to provide an organic compound that has good luminescence efficiency. This is possible. Alternatively, it is possible to provide organic compounds with high carrier transport properties. This can provide reliable organic compounds.

[0073] Furthermore, in one aspect of the present invention, a novel light-emitting element can be provided. Or, the luminous efficiency It is possible to provide a light-emitting element with good quality. Or, it is possible to provide a light-emitting element with good chromaticity. It is possible to provide a light-emitting element that emits blue light with good chromaticity. Alternatively, it can provide light-emitting elements with a good lifespan. Alternatively, it can provide driving voltages that are small. A light-emitting element can be provided.

[0074] Alternatively, another aspect of the present invention relates to a light-emitting device, electronic device, and display device with low power consumption. Each can be provided. Alternatively, in another aspect of the present invention, a highly reliable light-emitting device, Electronic devices and display devices can be provided, respectively. Alternatively, in another aspect of the present invention, We can provide light-emitting devices, electronic devices, and display devices, each with excellent display quality.

[0075] 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]

[0076] [Figure 1] Schematic diagram of a light-emitting element. [Figure 2] A diagram illustrating an example of a method for fabricating a light-emitting element. [Figure 3] A diagram illustrating an example of a method for fabricating a light-emitting element. [Figure 4] Conceptual diagram of an active matrix light-emitting device. [Figure 5] Conceptual diagram of an active matrix light-emitting device. [Figure 6] Conceptual diagram of an active matrix light-emitting device. [Figure 7] Conceptual diagram of a passive matrix type light-emitting device. [Figure 8] A diagram representing a lighting device. [Figure 9] A diagram representing electronic devices. [Figure 10] A diagram representing a light source device. [Figure 11] A diagram representing a lighting device. [Figure 12] A diagram representing a lighting device. [Figure 13] A diagram showing an in-vehicle display device and lighting system. [Figure 14] A diagram representing electronic devices. [Figure 15] A diagram representing electronic devices. [Figure 16] 1H NMR spectrum of 3,10FrA2Nbf(IV). [Figure 17] Absorption and emission spectra of 3,10FrA2Nbf(IV) in a toluene solution. [Figure 18]Absorption and emission spectra of 3,10FrA2Nbf(IV) in a thin film state. [Figure 19] MS spectrum of 3,10FrA2Nbf(IV). [Figure 20] 1H NMR spectrum of 2,9PCA2Nbf(III). [Figure 21] Absorption and emission spectra of 2,9PCA2Nbf(III) in a toluene solution. [Figure 22] Absorption and emission spectra of 2,9PCA2Nbf(III) in a thin film state. [Figure 23] MS spectrum of 2,9PCA2Nbf(III). [Figure 24] 3,10PCA2Nbf(IV) 1H NMR spectrum. [Figure 25] Absorption and emission spectra of 3,10PCA2Nbf(IV) in a toluene solution. [Figure 26] Absorption and emission spectra of 3,10PCA2Nbf(IV) in a thin film state. [Figure 27] MS spectrum of 3,10PCA2Nbf(IV). [Figure 28] A diagram showing the brightness-current density characteristics of light-emitting element 1 and comparative light-emitting element 1. [Figure 29] A diagram showing the current efficiency-luminance characteristics of light-emitting element 1 and comparative light-emitting element 1. [Figure 30] A diagram showing the brightness-voltage characteristics of light-emitting element 1 and comparison light-emitting element 1. [Figure 31] A diagram showing the current-voltage characteristics of light-emitting element 1 and comparison light-emitting element 1. [Figure 32] A diagram showing the power efficiency-luminance characteristics of light-emitting element 1 and comparative light-emitting element 1. [Figure 33] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting element 1 and comparative light-emitting element 1. [Figure 34] Emission spectra of light-emitting element 1 and comparison light-emitting element 1. [Figure 35]A diagram showing the normalized brightness-time variation characteristics of light-emitting element 1 and comparison light-emitting element 1. [Figure 36] A diagram showing the brightness-current density characteristics of light-emitting element 2 and comparative light-emitting element 2. [Figure 37] A diagram showing the current efficiency-luminance characteristics of light-emitting element 2 and comparative light-emitting element 2. [Figure 38] A diagram showing the brightness-voltage characteristics of light-emitting element 2 and comparison light-emitting element 2. [Figure 39] A diagram showing the current-voltage characteristics of light-emitting element 2 and comparison light-emitting element 2. [Figure 40] A diagram showing the power efficiency-luminance characteristics of light-emitting element 2 and comparative light-emitting element 2. [Figure 41] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting element 2 and comparative light-emitting element 2. [Figure 42] Emission spectra of light-emitting element 2 and comparison light-emitting element 2. [Figure 43] This figure shows the normalized brightness-time variation characteristics of light-emitting element 2 and comparison light-emitting element 2. [Figure 44] A diagram showing the brightness-current density characteristics of light-emitting element 3 and comparison light-emitting element 3. [Figure 45] A diagram showing the current efficiency-luminance characteristics of light-emitting element 3 and comparative light-emitting element 3. [Figure 46] A diagram showing the brightness-voltage characteristics of light-emitting element 3 and comparison light-emitting element 3. [Figure 47] A diagram showing the current-voltage characteristics of light-emitting element 3 and comparison light-emitting element 3. [Figure 48] A diagram showing the power efficiency-luminance characteristics of light-emitting element 3 and comparative light-emitting element 3. [Figure 49] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting element 3 and comparative light-emitting element 3. [Figure 50] Emission spectra of light-emitting element 3 and comparison light-emitting element 3. [Figure 51] A diagram showing the normalized brightness-time variation characteristics of light-emitting element 3 and comparison light-emitting element 3. [Figure 52] A diagram showing the brightness-current density characteristics of light-emitting element 4 and comparison light-emitting element 4. [Figure 53]A diagram showing the current efficiency-luminance characteristics of light-emitting element 4 and comparative light-emitting element 4. [Figure 54] A diagram showing the brightness-voltage characteristics of light-emitting element 4 and comparison light-emitting element 4. [Figure 55] A diagram showing the current-voltage characteristics of the light-emitting element 4 and the comparison light-emitting element 4. [Figure 56] A diagram showing the power efficiency-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 4. [Figure 57] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting element 4 and comparative light-emitting element 4. [Figure 58] Emission spectra of light-emitting element 4 and comparison light-emitting element 4. [Figure 59] A diagram showing the normalized brightness-time variation characteristics of light-emitting element 4 and comparison light-emitting element 4. [Figure 60] A diagram showing the brightness-current density characteristics of the light-emitting element 5 and the comparative light-emitting element 5. [Figure 61] A diagram showing the current efficiency-luminance characteristics of the light-emitting element 5 and the comparative light-emitting element 5. [Figure 62] A diagram showing the brightness-voltage characteristics of the light-emitting element 5 and the comparison light-emitting element 5. [Figure 63] A diagram showing the current-voltage characteristics of the light-emitting element 5 and the comparison light-emitting element 5. [Figure 64] A diagram showing the power efficiency-luminance characteristics of the light-emitting element 5 and the comparative light-emitting element 5. [Figure 65] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting element 5 and comparative light-emitting element 5. [Figure 66] Emission spectra of light-emitting element 5 and comparative light-emitting element 5. [Figure 67] A diagram showing the normalized brightness-time variation characteristics of the light-emitting element 5 and the comparative light-emitting element 5. [Figure 68] A diagram showing the brightness-current density characteristics of the light-emitting element 6 and the comparative light-emitting element 6. [Figure 69] A diagram showing the current efficiency-luminance characteristics of the light-emitting element 6 and the comparative light-emitting element 6. [Figure 70] A diagram showing the brightness-voltage characteristics of the light-emitting element 6 and the comparison light-emitting element 6. [Figure 71]A diagram showing the current-voltage characteristics of the light-emitting element 6 and the comparison light-emitting element 6. [Figure 72] A diagram showing the power efficiency-luminance characteristics of the light-emitting element 6 and the comparative light-emitting element 6. [Figure 73] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting element 6 and comparative light-emitting element 6. [Figure 74] Emission spectra of light-emitting element 6 and comparison light-emitting element 6. [Figure 75] A diagram showing the normalized brightness-time variation characteristics of light-emitting element 6 and comparative light-emitting element 6. [Figure 76] 1H NMR spectrum of 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dimethoxynaphthalene. [Figure 77] 1H NMR spectrum of 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dihydroxynaphthalene. [Figure 78] 1H NMR spectrum of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran. [Figure 79] 1H NMR spectrum of 1,5-bis(4-chloro-2-fluorophenyl)-2,7-dihydroxynaphthalene. [Figure 80] 1H NMR spectrum of 2,9-dichloronaphtho[2,1-b;6,5-b']bisbenzofuran [Figure 81] 1H NMR spectrum of 2,9PCA2Nbf(III)-02. [Figure 82] Absorption and emission spectra of 2,9PCA2Nbf(III)-02 in a toluene solution. [Figure 83] Absorption and emission spectra of 2,9PCA2Nbf(III)-02 in a thin film state. [Figure 84] MS spectrum of 2,9PCA2Nbf(III)-02. [Figure 85] 1H NMR spectrum of 3,10FrA2Nbf(IV)-02. [Figure 86]Absorption and emission spectra of 3,10FrA2Nbf(IV)-02 in a toluene solution. [Figure 87] Absorption and emission spectra of 3,10FrA2Nbf(IV)-02 in a thin film state. [Figure 88] MS spectrum of 3,10FrA2Nbf(IV)-02. [Figure 89] 3.10PCA2Nbf(IV)-02 1H NMR spectrum. [Figure 90] Absorption and emission spectra of 3,10PCA2Nbf(IV)-02 in a toluene solution. [Figure 91] Absorption and emission spectra of 3,10PCA2Nbf(IV)-02 in a thin film state. [Figure 92] MS spectrum of 3,10PCA2Nbf(IV)-02. [Figure 93] 1H NMR spectrum of 2,6-dihydroxy-1,5-diphenylnaphthalene. [Figure 94] 1H NMR spectrum of 2,6-bis(2-bromo-4-chlorophenoxy)-1,5-diphenylnaphthalene. [Figure 95] 1H NMR spectrum of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran. [Figure 96] 1H NMR spectrum of ph-3,10FrA2Nbf(IV)-II. [Figure 97] MS spectrum of ph-3,10FrA2Nbf(IV)-II. [Figure 98] A diagram showing the brightness-current density characteristics of the light-emitting element 7. [Figure 99] A diagram showing the current efficiency-luminance characteristics of the light-emitting element 7. [Figure 100] A diagram showing the brightness-voltage characteristics of the light-emitting element 7. [Figure 101] A diagram showing the current-voltage characteristics of the light-emitting element 7. [Figure 102] A diagram showing the power efficiency-luminance characteristics of the light-emitting element 7. [Figure 103] A diagram showing the external quantum efficiency-luminance characteristics of the light-emitting element 7. [Figure 104] Emission spectrum of light-emitting element 7. [Figure 105] A diagram showing the normalized brightness-time variation characteristics of the light-emitting element 7. [Figure 106] A diagram showing the brightness-current density characteristics of the light-emitting element 8. [Figure 107] A diagram showing the current efficiency-luminance characteristics of the light-emitting element 8. [Figure 108] A diagram showing the brightness-voltage characteristics of the light-emitting element 8. [Figure 109] A diagram showing the current-voltage characteristics of the light-emitting element 8. [Figure 110] A diagram showing the power efficiency-luminance characteristics of the light-emitting element 8. [Figure 111] A diagram showing the external quantum efficiency-luminance characteristics of the light-emitting element 8. [Figure 112] Emission spectrum of light-emitting element 8. [Figure 113] A diagram showing the normalized brightness-time variation characteristics of the light-emitting element 8. [Figure 114] A diagram showing the brightness-current density characteristics of the light-emitting element 9. [Figure 115] A diagram showing the current efficiency-luminance characteristics of the light-emitting element 9. [Figure 116] A diagram showing the brightness-voltage characteristics of the light-emitting element 9. [Figure 117] A diagram showing the current-voltage characteristics of the light-emitting element 9. [Figure 118] A diagram showing the power efficiency-luminance characteristics of the light-emitting element 9. [Figure 119] A diagram showing the external quantum efficiency-luminance characteristics of the light-emitting element 9. [Figure 120] Emission spectrum of light-emitting element 9. [Figure 121] A diagram showing the normalized brightness-time variation characteristics of the light-emitting element 9. [Figure 122] A diagram showing the relationship between y-chromaticity and external quantum efficiency of bottom emission devices using various blue fluorescent dopants. [Figure 123] This diagram shows the relationship between y-chromaticity and current efficiency of a top-emission element with varying optical path length. [Figure 124] Absorption and emission spectra of ph-3,10FrA2Nbf(IV)-II in a toluene solution. [Figure 125] Absorption and emission spectra of ph-3,10FrA2Nbf(IV)-II in a thin film state. [Figure 126] 3,10PCA2Nbf(II) 1H NMR spectrum. [Figure 127] Absorption and emission spectra of 3,10PCA2Nbf(II) in a toluene solution. [Figure 128] Absorption and emission spectra of 3,10PCA2Nbf(II) in a thin film state. [Figure 129] MS spectrum of 3,10PCA2Nbf(II). [Figure 130] ¹H NMR spectrum of 2,9FrA2Nbf(III)-02. [Figure 131] Absorption and emission spectra of 2,9FrA2Nbf(III)-02 in a toluene solution. [Figure 132] Absorption and emission spectra of 2,9FrA2Nbf(III)-02 in a thin film state. [Figure 133] MS spectrum of 2,9FrA2Nbf(III)-02. [Figure 134] 1H NMR spectrum of ph-2,9FrA2Nbf(III)-II. [Figure 135] Absorption and emission spectra of ph-2,9FrA2Nbf(III)-II in a toluene solution. [Figure 136] Absorption and emission spectra of ph-2,9FrA2Nbf(III)-II in a thin film state. [Figure 137] MS spectrum of ph-2,9FrA2Nbf(III)-II. [Figure 138] 1H NMR spectrum of ph-3,10FrA2Nbf(IV)-02. [Figure 139]Absorption and emission spectra of ph-3,10FrA2Nbf(IV)-02 in a toluene solution. [Figure 140] Absorption and emission spectra of ph-3,10FrA2Nbf(IV)-02 in a thin film state. [Figure 141] MS spectrum of ph-3,10FrA2Nbf(IV)-02. [Figure 142] 1H NMR spectrum of 3,10iPrFrA2Nbf(IV)-02. [Figure 143] Absorption and emission spectra of 3,10iPrFrA2Nbf(IV)-02 in a toluene solution. [Figure 144] Absorption and emission spectra of 3,10iPrFrA2Nbf(IV)-02 in a thin film state. [Figure 145] MS spectrum of 3,10iPrFrA2Nbf(IV)-02. [Figure 146] Absorption and emission spectra of 3,10ThA2Nbf(IV) in a toluene solution. [Figure 147] Absorption and emission spectra of 3,10ThA2Nbf(IV) in a thin film state. [Figure 148] MS spectrum of 3,10ThA2Nbf(IV). [Figure 149] ¹H NMR spectrum of 2,9PCBA2Nbf(III). [Figure 150] Absorption and emission spectra of 2,9PCBA2Nbf(III) in a toluene solution. [Figure 151] Absorption and emission spectra of 2,9PCBA2Nbf(III) in a thin film state. [Figure 152] MS spectrum of 2,9PCBA2Nbf(III). [Figure 153] 1H NMR spectrum of 3,10mmtBuFrA2Nbf(IV)-02. [Figure 154]Absorption and emission spectra of 3,10mmtBuFrA2Nbf(IV)-02 in a toluene solution. [Figure 155] MS spectrum of 3,10 mmtBuFrA2Nbf(IV)-02. [Figure 156] 1H NMR spectrum of 3,10FrBA2Nbf(IV)-II. [Figure 157] Absorption and emission spectra of 3,10FrBA2Nbf(IV)-II in a toluene solution. [Figure 158] Absorption and emission spectra of 3,10FrBA2Nbf(IV)-II in a thin film state. [Figure 159] MS spectrum of 3,10FrBA2Nbf(IV)-II. [Figure 160] A diagram showing the brightness-current density characteristics of light-emitting elements 10 to 15. [Figure 161] A diagram showing the current efficiency-luminance characteristics of light-emitting elements 10 to 15. [Figure 162] A diagram showing the brightness-voltage characteristics of light-emitting elements 10 to 15. [Figure 163] A diagram showing the current-voltage characteristics of light-emitting elements 10 to 15. [Figure 164] A diagram showing the power efficiency-luminance characteristics of light-emitting elements 10 to 15. [Figure 165] A diagram showing the external quantum efficiency-luminance characteristics of light-emitting elements 10 to 15. [Figure 166] Emission spectra of light-emitting elements 10 to 15. [Figure 167] A diagram showing the normalized brightness-time variation characteristics of light-emitting elements 10 to 15. [Modes for carrying out the invention]

[0077] The embodiments of the present invention will be described in detail below with reference to the drawings. However, the present invention is as follows The description is not limited to the present invention, and the form and details may not depart from the spirit and scope of the present invention. Those skilled in the art will readily understand that the parameters can be modified in various ways. Accordingly, the present invention is described below. This should not be interpreted as being limited to the contents described in the embodiment.

[0078] (Embodiment 1) An organic compound according to one aspect of the present invention is an organic compound represented by the following general formula (G1).

[0079] [ka]

[0080] In the above general formula (G1), B is a substituted or unsubstituted naphthobisbenzofuran skeleton. Substituted or unsubstituted naphthobisbenzothiophene skeletons and substituted or unsubstituted naphthobene skeletons. Represents one of the zofuranobenzothiophene skeletons. Skeleton B has one or two substitutions. Or an unsubstituted arylamino group is bonded (i.e., q is 1 or 2), but the aryl Luamines are not amines that have only a phenyl group or only a simple aryl group, but rather substituted or This includes an unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and It is an arylamine having at least one substituted or unsubstituted carbazolyl group. It is characterized by the following.

[0081] In the above general formula (G1), A is a substituted or unsubstituted dibenzofuranyl group, or a substituted or Either an unsubstituted dibenzothiophenyl group or a substituted or unsubstituted carbazolyl group It represents

[0082] Furthermore, in the above general formula (G1), Ar 1 These are substituted or unsubstituted carbon atoms with 6 to 25 carbon atoms. Aromatic hydrocarbon groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzo This represents either a thiophenyl group or a substituted or unsubstituted carbazolyl group.

[0083] In the above general formula (G1), α 1 , α 2 and α 3 These can be substituted or left unsubstituted independently. It is a divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, where l, m, and n are each independently It takes one of the following values: 0, 1, or 2.

[0084] Substituted or unsubstituted naphthobisbenzofuran skeleton, substituted or unsubstituted naphthobisbe Naphthothiophene skeleton, or substitute or unsubstituted naphthobenzofuranose benzothiophene skeleton The crystalline structure is a very useful framework as a light-emitting phosphodiopter in light-emitting devices. The organic compound in question has a high luminescence efficiency. Because it exhibits high and good blue light emission, the light-emitting device using this organic compound has a high light emission effect. This allows for the creation of a blue light-emitting element with good fluorescence efficiency. Various materials have been developed for blue fluorescence. However, this organic compound exhibits blue light emission with very good chromaticity, making it suitable for 8K displays. The color gamut covers the ITU-R BT.2020 standard, which is an international standard for ultra-wide color gamuts. It is a very promising material as a blue light-emitting material for expressing light.

[0085] In particular, the inventors of the present invention have found that these skeletons can be substituted or unsubstituted with the aforementioned dibenzofuranyl dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, and substituted or unsubstituted carbazolyl groups. A light-emitting element using an organic compound having a special arylamine having at least one group We found that the child could become a light-emitting element with even better characteristics. Specifically, the luminous efficiency was improved. This has effects such as improving the image quality and further improving color purity.

[0086] In the above general formula (G1), Ar 1 and / or A may each represent either a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. However, these are preferably groups represented by the following general formula (g1) to general formula (g3). In the above general formula (g1) to general formula (g3), R to R

[0087] [Chemical formula]

[0088] In the above general formula (g1) to general formula (g3), one of R 1 to R 9 represents a single bond, and the rest each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, a cyclic hydrocarbon group having 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms. However, when A is a group represented by the above general formula (g3) and R in the group represented by the above general formula (g 3) represents a single bond, n shall be 1 or 2. Also, when Ar 9 is a group represented by the above general formula (g3) and R in the group represented by the above general formula (g3) represents a single bond, m shall be 1 or 2. 1 When either or both of Ar and A are groups represented by the above general formula (g1), it is preferable that any one of R 9 to R

[0089] is a single bond. When it is a group represented by the above general formula (g2), it is preferable that any one of R 1 to R 1 to R 3 is a single bond. When it is a group represented by the above general formula (g3 ​​​​​If the group is represented by ), R 2 or R 3 It is preferable that the bond is a single bond.

[0090] Note that the single bond referred to here is α in the general formula (G1) above. 2 , α 3 , or nitrogen (A This represents a joint with (Min).

[0091] Furthermore, A in the above general formula (G1) is the group represented by the above general formula (g3) and R 9 Except for single bonds, configurations where n is 0 require fewer synthesis steps and have a lower sublimation temperature. This is preferable. Also, the fact that l and n are 0 regardless of A reduces the number of synthesis steps. Furthermore, the sublimation temperature is also lower, which is desirable.

[0092] In the above general formula (G1), A is the group represented by the above general formula (g3) and R 9 Single In the case of a compound, a configuration where n is 1 is preferred because it is easy to synthesize and chemically stable. Ar 1 The group is represented by the above general formula (g3) and R 9 The same applies when it is a single bond. For this reason, a configuration where m is 1 is preferable.

[0093] Furthermore, A and Ar in general formula (G1) 1 Either one or both of the above general formula A group represented by (g1) or a group represented by the above general formula (g2), preferably the above general formula ( The group represented by g1) indicates that the organic compound represented by the above general formula (G1) emits light at short wavelengths. This is preferable because it becomes light. In this case, the group represented by the above general formula (g1) or the above general formula (g 2) The α of the group represented by 2 , α 3 , or the position of the single bond that bonds with nitrogen (amine) is R 1 or R 2 This is preferable as it results in shorter wavelength emission. Also, the above general formula (g1) is The α of the group that is formed or the group represented by the above general formula (g2) 2 , α 3 , or nitrogen (amine) The position of the single bond that connects to it is R 2 or R 3 This is preferable because it results in a higher emission quantum yield. Also, the position of the single bond is R 2 This is preferable because it narrows the emission spectrum.

[0094] Also, Ar in general formula (G1) 1 If either or both of A are given by the above general formula (g3) It is preferable that the group is represented as such, as this improves reliability.

[0095] Also, Ar 1 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms. A lower temperature is preferable.

[0096] Furthermore, a value of q of 2 is preferable because it results in a higher emission quantum yield. A value of q of 1 is preferable because it results in a lower sublimation temperature. The degree is lower, which is preferable.

[0097] In this specification, sublimation temperature also includes the meaning of evaporation temperature.

[0098] A typical example of the group represented by A in the above general formula (G1) is shown in the following structural formula (Ar-50 These are shown as (Ar-66). Furthermore, these are hydrocarbon groups having 1 to 10 carbon atoms, carbon Cyclic hydrocarbon groups with 3 to 10 prime numbers, substituted or unsubstituted aromatic hydrocarbons with 6 to 14 carbon atoms. It may have substituents such as elementary groups.

[0099] [ka]

[0100] Furthermore, in the above general formula (G1), Ar 1 These are substituted or unsubstituted carbon atoms with 6 to 25 carbon atoms. Aromatic hydrocarbon groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzo Represents either a thiophenyl group or a substituted or unsubstituted carbazolyl group. Unsubstituted aromatic hydrocarbon groups having 6 to 25 carbon atoms include, specifically, phenyl groups and biphenyl groups. Nyl group, terphenyl group, naphthyl group, fluorenyl group, dimethylfluorenyl group, spi fluoroenyl group, diphenylfluoroenyl group, phenanthryl group, anthryl group, diphenylfluoroenyl Examples include the droanthryl group, triphenylenyl group, pyrenyl group, etc. 1 of Typical examples are shown in the following structural formulas (Ar-50) to (Ar-66), (Ar-100) to ( These are shown in Ar-119), (Ar-130) to (Ar-140). Hydrocarbon groups having 1 to 10 carbon atoms, cyclic hydrocarbon groups having 3 to 10 carbon atoms, substituted or unsubstituted. It may have substituents such as aromatic hydrocarbon groups having 6 to 14 carbon atoms.

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] Note that, as in (Ar-50), (Ar-53), and (Ar-54), the carbazolyl group has 9 At this position, α in the general formula (G1) 2 ya alpha 3 , having a structure bonded to nitrogen (amine) The compound is preferred because its conjugation does not easily extend, and short-wavelength emission can be obtained.

[0105] Also, (Ar-51), (Ar-55), (Ar-56), (Ar-57), (Ar-6 As in 0), α in the general formula (G1) 2 ya alpha 3 , nitrogen (amine) has a carbazolyl group The organic compound has a bond at the 3rd position, and the dibenzofuranyl group has a structure in which it is bonded at the 2nd position. Organic compounds, organic compounds having a structure in which a dibenzothiophenyl group is bonded at the 2 position, Effects include easier extension of the role, high hole transportability, long-wavelength emission, and good reliability. This is preferable because it yields a desirable result. The effect is particularly pronounced with the carbazolyl group.

[0106] Also, in general formulas (G1), such as (Ar-52), (Ar-59), and (Ar-62) keru α 2 ya alpha 3 It has a structure in which a carbazolyl group is bonded to the nitrogen (amine) at the 2 position. Organic compounds, organic compounds having a structure in which a dibenzofuranyl group is bonded at the 3-position, dibenzo Organic compounds having a structure in which a thiophenyl group is bonded at the 3rd position exhibit high carrier transport properties. A reduction in the driving voltage can be expected, which is desirable.

[0107] Also, as in (Ar-51), (Ar-52), (Ar-55), (Ar-56), Having an aryl group bonded to the 9th position of the rubazolyl group yields advantages such as improved reliability. Therefore, it is preferable.

[0108] Also, (Ar-58), (Ar-61), (Ar-63) to (Ar-66), α in general formula (G1) 2 ya alpha 3 A dibenzofuranyl group is bonded to the nitrogen (amine) at the 4th position. An organic compound having a structure in which a dibenzothiophenyl group is bonded at the 4th position. The organic compounds possessed by this material exhibit less conjugation extension, yield short-wavelength emission, and have good reliability, preferable.

[0109] Furthermore, those with linked phenyl groups, such as (Ar-100) to (Ar-108), are also The effect is less pronounced and the emission wavelength is short, which is desirable.

[0110] Furthermore, as in (Ar-100) to (Ar-119), a benzene ring, a naphthalene ring, and ful Rings with two or fewer fused rings in a six-membered ring, such as an oren ring, or rings with six members, such as a phenanthrene ring. Even if the number of fused rings in a membered ring is three or more, if the other six-membered rings are only at positions a, c, and e relative to the six-membered ring... Compounds composed of fused rings and hydrocarbons have difficulty expanding conjugation, and luminescence is... This is preferable because it results in a short wavelength.

[0111] α in the above general formula (G1) 1 ~ α 3 Each of these independently represents the number of substituted or unsubstituted carbon atoms. It represents 6 to 25 divalent aromatic hydrocarbon groups, specifically phenylene groups and biphenylene groups. Group, taphenylene group, naphthylene group, fluorenylene group, dimethylfluorenyl group, Examples include α. 1 ~ α 3 Typical examples include the following structural formulas (Ar-1) to (A Groups represented by r-33) can be listed. Furthermore, these may have 1 to 1 carbon atoms. 0 hydrocarbon groups, cyclic hydrocarbon groups with 3 to 10 carbon atoms, substituted or unsubstituted groups with 6 to 10 carbon atoms It may have substituents such as 14 aromatic hydrocarbon groups.

[0112] [ka]

[0113] [ka]

[0114] Note α 1 ~ α 3 (Ar-1) to (Ar-11) are phenylene groups or phenylene groups. If the group consists of several nilen groups linked together, the conjugation does not extend easily, and the singlet excitation level is kept high. It is preferable. In particular, a composition containing a metaphenylene group is preferred because its effect is remarkable. i. Also, α 1 ~ α 3 The configuration in which the paraphenylene group is present makes it highly reliable as a light-emitting material. Furthermore, it is preferable that the substituent is fluorene, such as (Ar-24) to (Ar-27). When linked by carbon atoms with sigma bonds, such as at position 9, conjugation is less likely to extend, and the S1 level is high. Because it is kept in a low state, the emission wavelength becomes shorter, which is preferable.

[0115] If l, m, and n are each 2, then α 1 , α 2 and α 3 These are different substituents They may be linked together. For example, (Ar-17) and (Ar-18) are naphthylene and phenyl It is a combination of two "ren" characters.

[0116] In the organic compound represented by the above general formula (G1), the substituted or unsubstituted B Naphthobisbenzofuran skeleton, substituted or unsubstituted naphthobisbenzothiophene skeleton Alternatively, the substituted or unsubstituted naphthobenzofuranosethiophene skeleton can be represented by the following general formula (B 1) Preferably, the skeleton is one of the forms represented by (B4).

[0117] [ka]

[0118] In the above general formulas (B1) to (B4), X 2 and X 3 Each of them independently produces oxygen It represents an atom or a sulfur atom. Note that for ease of synthesis, both are the same atom. This is preferable. Furthermore, the fact that both are oxygen atoms makes synthesis easy, and singlet excitation is also desirable. This allows for a higher starting level, shorter wavelength emission, and a higher emission quantum yield. It is preferable because it is effective. 2 , X 3 The more oxygen atoms there are, the shorter the wavelength of light emitted. Furthermore, the more sulfur atoms there are, the longer the wavelength of emission it exhibits, thus achieving the desired singlet excitation level or emission wave. It can be selected at the discretion of the leader.

[0119] The organic compound represented by the above general formula (G1) has an emission wavelength determined by the skeleton represented by B. A tendency for change is observed, where B is the framework represented by general formula (B2) and general formula (B4) The wavelengths increase in the order of skeleton, skeleton represented by general formula (B1), and skeleton represented by general formula (B3). Therefore, you should select the above skeleton according to the desired emission color. If light is to be obtained, the compound represented by general formula (B2) is preferred. A relatively long wavelength blue light is desired. If light is to be obtained, the compound represented by general formula (B3) is preferred.

[0120] Furthermore, the organic compound represented by the above general formula (G1) has a skeleton represented by B that is equivalent to the general formula (B3). With a skeleton represented by this, the emission spectrum is narrowed, and emission with high color purity can be obtained. preferable.

[0121] Furthermore, in the skeleton represented by the above general formula (B1), R 10 ~R 21 Choose one of the following In this case, 2 represents a single bond, and the remaining atoms are independently hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and carbon. Cyclic hydrocarbon groups with 3 to 10 prime numbers, substituted or unsubstituted aromatic hydrocarbons with 6 to 14 carbon atoms. It represents either an elementary group, a substituted or unsubstituted diarylamino group having 12 to 32 carbon atoms. Note that single bonds are R 10 ~R 21 R 11 , R 12 , R 17 and R 18 any of It is preferable that the combination be 1 or 2, as this simplifies the synthesis process.

[0122] Furthermore, in the above general formula (B1), R 10 ~R 21 If any two of them are single bonds ( That is, when q in the above general formula (G1) is 2, R 11 or R 12 Noise Either one, and R 17 or R 18 The ease of synthesis depends on whether one of them is a single bond. Therefore, it is preferable. Also, in this case, R 11 and R 17 The fact that it is a single bond allows for long-wavelength emission. From the perspective of obtaining, R 12 and R 18 When it is a single bond, short-wavelength emission is obtained, and the amount of light emitted It is preferable because it has good efficiency, a high molar extinction coefficient, and good reliability when emitting light.

[0123] Furthermore, in the above general formula (B2), R 30 ~R 41 One or two of these are single bonds The remaining parts are, independently, hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a hydrocarbon group with 3 to 10 carbon atoms. A cyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or This represents any of the unsubstituted diarylamino groups with 12 to 32 carbon atoms. Note that single bonds are , R 30 ~R 41 R 31 , R 32 , R 37 and R 38 Either 1 or 2 Having a certain feature is preferable because it simplifies the synthesis process.

[0124] Furthermore, in the above general formula (B2), R 30 ~R 41 If any two of them are single bonds ( That is, when q in the above general formula (G1) is 2, R 31 or R 32 Noise Either one, and R 37 or R 38 The ease of synthesis depends on whether one of them is a single bond. Therefore, it is preferable. Also, in this case, R 31 and R 37 The fact that it is a single bond allows for long-wavelength emission. From the perspective of obtaining, R 32 and R 38 When it is a single bond, short-wavelength emission is obtained, and the amount of light emitted It is preferable because it has good efficiency, a high molar extinction coefficient, and good reliability when emitting light.

[0125] Furthermore, in the above general formula (B3), R 50 ~R 61One or two of these are single bonds The remaining parts are, independently, hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a hydrocarbon group with 3 to 10 carbon atoms. A cyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or R represents any of the unsubstituted diarylamino groups. Note that single bonds are represented by R. 50 ~R 61 of Uchi R 51 , R 52 , R 57 and R 58 It is possible to combine them if either one or two of the following conditions are met. It is preferable because it is feces.

[0126] Furthermore, in the above general formula (B3), R 50 ~R 61 If any two of them are single bonds ( That is, when q in the above general formula (G1) is 2, R 51 or R 52 Noise Either one, and R 57 or R 58 The ease of synthesis depends on whether one of them is a single bond. Therefore, it is preferable. Also, in this case, R 51 and R 57 The fact that it is a single bond allows for long-wavelength emission. From the perspective of obtaining, R 52 and R 58 When it is a single bond, short-wavelength emission is obtained, and the amount of light emitted It is preferable because it has good efficiency, a high molar extinction coefficient, and good reliability when emitting light.

[0127] Furthermore, in the above general formula (B4), R 70 ~R 81 One or two of these are single bonds The remaining parts are, independently, hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a hydrocarbon group with 3 to 10 carbon atoms. A cyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or This represents any of the unsubstituted diarylamino groups with 12 to 32 carbon atoms. Note that single bonds are , R 70 ~R 81 R 71 , R 72 , R 77 and R 78 Either 1 or 2 Having a certain feature is preferable because it simplifies the synthesis process.

[0128] Furthermore, in the above general formula (B4), R 70 ~R 81 If any two of them are single bonds ( That is, when q in the above general formula (G1) is 2, R 71 or R 72 Noise Either one, and R 77 or R 78 The ease of synthesis depends on whether one of them is a single bond. Therefore, it is preferable. Also, in this case, R 71 and R 78 The fact that it is a single bond allows for long-wavelength emission. From the perspective of obtaining, R 72 and R 77 When it is a single bond, short-wavelength emission is obtained, and the amount of light emitted It is preferable because it has good efficiency, a high molar extinction coefficient, and good reliability when emitting light.

[0129] Note that the single bond referred to here is α in the general formula (G1) above. 1 or bonds with nitrogen (amine) It represents.

[0130] Furthermore, in the above general formulas (B1) to (B4), R 10 ~R 21 , R 30 ~ R 41 , R 50 ~R 61 , R 70 ~R 81 Of the substituents represented by , those that are not single bonds It is preferable that the substance be hydrogen because its synthesis is simpler and its sublimation temperature is lower. On the other hand, if the substance is not hydrogen By using a conversion agent, it is possible to improve heat resistance and solubility in solvents, and the emission wavelength can be changed. It can be shifted to longer wavelengths.

[0131] Furthermore, the organic compound represented by the above general formula (G1) is represented by the following general formula (G1-1) It is preferable that it be an organic compound.

[0132] [ka]

[0133] However, in the above general formula (G1-1), B is the same as in the following general formula (B1-1) or (B3-1). It is a group represented by . Also, Ar 1 These are substituted or unsubstituted aromatic carbons with 6 to 25 carbon atoms. It is a hydrogenated group, and A is a group represented by the following general formula (g0). Also, m is a constant from 0 to 2. It represents a number. Also, α 2 These are substituted or unsubstituted divalent aromatic hydrocarbon groups having 6 to 14 carbon atoms. That is the case.

[0134] [ka]

[0135] However, in the above general formula (B1-1) or (B3-1), X 2 and X 3 Each It independently represents an oxygen atom or a sulfur atom. Also, R 12 ,R 18 , R 52 and R 58 is single It represents a combination.

[0136] [ka]

[0137] However, in the above general formula (g0), X0 is an oxygen atom, or a substituted or unsubstituted atom. It is a nitrogen atom to which a phenyl group is bonded. Also, R 2 This represents a single bond.

[0138] Furthermore, the molecular weight of the organic compound represented by the above general formula (G1) or (G1-1) is determined by its sublimation properties. Considering this, it is preferable that it be 1300 or less, preferably 1000 or less. Considering the film quality, It is preferable that the number of offspring be 650 or more.

[0139] Furthermore, if the skeleton or group bonded to the above-mentioned organic compound has substituents, those substituents shall be For example, hydrocarbon groups having 1 to 10 carbon atoms, cyclic hydrocarbon groups having 3 to 10 carbon atoms, and carbon 6 atoms. It is preferably any of the 14 aromatic hydrocarbon groups.

[0140] In the substituent represented by R above, or a substituent further bonded to the substituent, having 1 carbon atom The 10 hydrocarbon groups include methyl, ethyl, propyl, isopropyl, and butyric groups. butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group Examples include carbon atoms, decyl groups, and icosyl groups. Also, cyclic carbon atoms with 3 to 10 carbon atoms. Examples of hydrogenated groups include cyclopropyl groups and cyclohexyl groups. Furthermore, aromatic hydrocarbon groups having 6 to 14 carbon atoms include phenyl groups, biphenyl groups, and naphthium groups. Examples include the tyl group, phenanthryl group, anthryl group, and fluorenyl group.

[0141] Furthermore, if the substituent represented by R is a diarylamino group having 12 to 32 carbon atoms, The two aryl groups of the diarylamino group each independently have 6 to 16 carbon atoms. It is more preferable that the aromatic hydrocarbon group is phenyl fluorenyl group, biphenyl group, naphthyl group, phenanthryl group, anthryl group, fluorenyl group, Examples include naphthylphenyl groups.

[0142] Of these, aromatic hydrocarbon groups having 6 to 14 carbon atoms and groups having 12 to 32 carbon atoms The diarylamino group further consists of an aliphatic hydrocarbon group having 1 to 6 carbon atoms and an alicyclic group having 3 to 6 carbon atoms. It may have substituents such as a hydrocarbon group.

[0143] Examples of organic compounds of the present invention having the above-described structure are shown below.

[0144] [ka]

[0145] [ka]

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150]

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[0151]

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[0152]

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[0153]

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[0154]

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[0155]

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[0156]

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[0157]

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[0158]

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[0159]

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[0160]

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[0161] [ka]

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] [ka]

[0169] In general formulas (B1) to (B4), X 2 and X 3 This is the compound (905) They may be different. However, it is preferable for them to be the same for the skeleton of B in the general formula (G1). The process is simple and preferable.

[0170] When q in general formula (G1) is 2, the diarylamino group is of compound (903) Thus, the substituents do not have to be the same. However, it is preferable if they are the same as it simplifies the synthesis. It seems so.

[0171] In general formula (G1), when q is 2, that is, diarylamino substitutes on skeleton B. If there are two groups, like in compound (901), the substituent is X of B. 2 and X 3 against The bonds may be asymmetrical. However, compound (100), compound (200), and compound compound (300), compound (400), compound (500), compound (600), compound (70 0), compound (800), compound (900), etc., the symmetrical one is the one that synthesizes the skeleton of B. This is simple and preferable.

[0172] In general formula (G1), as in compound (904), one of the two arylamino groups is , substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group and an arylamino group having either a substituted or unsubstituted carbazolyl group, The other arylamino group may be a diarylamino group. However, It is preferable that the two arylamino groups are the same group, as this simplifies the synthesis. Of the arylamino groups, at least one is a substituted or unsubstituted dibenzofuranyl group, A substituted or unsubstituted dibenzothiophenyl group and a substituted or unsubstituted carbazolyl group If the arylamino group has a shift, the light emission when the organic compound is used as a light-emitting material will be The reliability of the element is good, which is desirable.

[0173] If at least one of l, m, and n in general formula (G1) is 2, then compound (907) To the alpha 1 , α 2 and α 3 Each of these can be made up of different interconnected skeletons.

[0174] Next, an example of a method for synthesizing the organic compound of the present invention as described above will be explained. The following are organic compounds represented by the general formula (G1).

[0175] [ka]

[0176] However, in the formula, B is a substituted or unsubstituted naphthobisbenzofuran skeleton, or a substituted or unsubstituted naphthobisbenzofuran skeleton. Phthobisbenzothiophene skeleton and substituted or unsubstituted naphthobenzofuranosebenzothio It represents one of the Fen skeletons. Also, Ar 1 These are substituted or unsubstituted carbon atoms with 6 to 14 carbon atoms. Aromatic hydrocarbon groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzo It is either a thiophenyl group or a substituted or unsubstituted carbazolyl group. A is substituted or an unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and It is either a substituted or unsubstituted carbazolyl group, α 1 ~ α 3 Each is independent It is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 14 carbon atoms. Also, l, m, n represents an independent integer from 0 to 2, and q is either 1 or 2.

[0177] The organic compound represented by the above general formula (G1) is synthesized as shown in the synthesis scheme below. By cross-coupling a1) with an arylamine compound (a2), It is possible. X 1 Examples include halogen groups such as chlorine, bromine, and iodine, and sulfonyl groups. Examples include the base. D 1 If l is 0 (i.e., compound (a1) is a secondary amine), then hydrogen This represents a value of 1 or more (i.e., compound (a1) is a tertiary amine), and if it is 1 or more, it is a boronic acid or a dialkoxy. Boronic acid, arylaluminum, arylzirconium, arylzinc, or aryl This represents tin, etc.

[0178] [ka]

[0179] This reaction can proceed under various conditions, one example being in the presence of a base. A synthesis method using a metal catalyst can be applied. For example, if l is 0, then Ullmanka The Plupling or Hartwig-Buchwald reaction can be used. The Suzuki-Miyaura reaction can be used for the combination.

[0180] Note that here, compound (a2) is reacted with compound (a1) in q equivalent amounts, but q is Two or more substituents, that is, two or more substituents represented by the parentheses q for B in compound (G1). Furthermore, if those substituents are not the same, then compound (a2) is treated as one type of compound (a1). It's okay to have them react to it.

[0181] As described above, an organic compound according to one embodiment of the present invention can be synthesized.

[0182] The above compound (a1) is one of the following general formulas (B1-a1) to (B4-a1). Examples include the following. These are useful compounds for synthesizing compounds according to one embodiment of the present invention. It is a substance. Its raw materials are equally useful. Regarding the synthesis method, the position of halogen substitution... By appropriately modifying the parameters, the components can be synthesized in the same manner as in the embodiments described later.

[0183] [ka]

[0184] In the above general formulas (B1-a1) to (B4-a1), X 2 and X 3 Each These independently represent either an oxygen atom or a sulfur atom.

[0185] Furthermore, in the above general formula (B1-a1), R 10 ~R 21 Either 1 or 2 It represents a halogen, and the remaining ones are independently hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a group with 3 carbon atoms. Cyclic hydrocarbon groups of up to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 14 carbon atoms, This represents either a substituted or unsubstituted diarylamino group with 12 to 32 carbon atoms. Halogen is R 10 ~R 21 R 11 , R 12 , R 17 and R 18 any one Alternatively, having 2 is preferable because it simplifies the synthesis process.

[0186] Furthermore, in the above general formula (B1-a1), R 10 ~R 21 If any two of them are halogens In that case, R 11 or R 12 Either one of the following, and R 17 or R 18 Either one It is preferable that the element is a halogen due to the ease of synthesis. Also, in this case, R 11 and R 1 7 Preferably, is a halogen, or R 12 and R 18 The fact that it is a halogen preferable.

[0187] Furthermore, in the above general formula (B2-a1), R 30 ~R 41 Either 1 or 2 It represents a halogen, and the remaining ones are independently hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a group with 3 carbon atoms. Cyclic hydrocarbon groups of up to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 14 carbon atoms, This represents either a substituted or unsubstituted diarylamino group with 12 to 32 carbon atoms. Halogen is R 30 ~R 41 R 31 , R 32 , R 37 and R 38 any one Alternatively, having 2 is preferable because it simplifies the synthesis process.

[0188] Furthermore, in the above general formula (B2-a1), R 30 ~R 41 If any two of them are halogens In that case, R 31 or R 32 Either one of the following, and R 37 or R 38 Either one It is preferable that the element is a halogen due to the ease of synthesis. Also, in this case, R 31 and R 3 7 Preferably, is a halogen, or R 32 and R 38 The fact that it is a halogen preferable.

[0189] Furthermore, in the above general formula (B3-a1), R 50 ~R 61Either 1 or 2 It represents a single bond, with the remaining atoms independently being hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a hydrocarbon group with 3 carbon atoms. Up to 10 halogen hydrocarbon groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 14 carbon atoms , represents either a substituted or unsubstituted diarylamino group. Note that halogens are represented by R 50 ~R 61 R 51 , R 52 , R 57 and R 58 It must be one or two of the following: It is preferable.

[0190] Furthermore, in the above general formula (B3-a1), R 50 ~R 61 If any two of them are halogens In that case, R 51 or R 52 Either one of the following, and R 57 or R 58 Either one It is preferable that the element is a halogen due to the ease of synthesis. Also, in this case, R 51 and R 5 7 Preferably, is a halogen, or R 52 and R 58 The fact that it is a halogen preferable.

[0191] Furthermore, in the above general formula (B4-a1), R 70 ~R 81 Either 1 or 2 It represents a halogen, and the remaining ones are independently hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, and a group with 3 carbon atoms. Cyclic hydrocarbon groups of up to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 14 carbon atoms, This represents either a substituted or unsubstituted diarylamino group with 12 to 32 carbon atoms. Halogen is R 70 ~R 81 R71 , R 72 , R 77 and R 78 any one Alternatively, it is preferable that it be 2.

[0192] Furthermore, in the above general formula (B4-a1), R 70 ~R 81 If any two of them are halogens In that case, R 71 or R 72 Either one of the following, and R 77 or R 78 Either one It is preferable that the element is a halogen due to the ease of synthesis. Also, in this case, R 71 and R 7 8 Preferably, is a halogen, or R 72 and R 77 The fact that it is a halogen preferable.

[0193] Next, we will explain the synthesis method of the organic compound represented by the general formula (B1-a1) described above. The general formula (B1-a1) is shown below. Each substituent and X 2 and X 3 Regarding this, see the above. It is identical to that thing.

[0194] [ka]

[0195] As shown in the scheme below, naphthalene compounds (C1-11), aryl compounds (C1- 12), and by cross-coupling the aryl compounds (c1-13), A naphthalene compound represented by (c1-14) can be obtained. 1 Ya B 2 Each Examples include boronic acid and dialkoxyboronic acid.3 Ya Y 4 These include chlorine, bromine, etc. This represents halogen groups and sulfonyl groups. Note that Y 3 Ya Y 4 The position shown is just one example, and in this synthesis example... In the above general formula (B1-a1), R 12 and R 18 Y at position 3 Ya Y 4 An example of introducing this is shown. However, Y 3 Ya Y 4 is R 10 ~R 21 It can be installed in any of these positions. , Y 3 or Y 4 It is acceptable to implement only one of them. 3 Ya Y 4 The installation location By making this change, substituents represented by (a2) above can be introduced at various positions. It becomes possible.

[0196] Also, in the following scheme, Y 1 and Y 2 is a halogen such as bromine or iodine or sulfonyl Represents the base. Y 1 and Y 2 is Y 3 Ya Y 4 A more reactive leaving group is preferred.

[0197] [ka]

[0198] This reaction can be carried out under various conditions, but one example is using a metal catalyst in the presence of a base. There is a synthesis method that uses [a specific method]. A concrete example of this synthesis method is the Suzuki-Miyaura reaction. It is possible.

[0199] Here, we will simultaneously use compounds (c1-12) and (c1-13) and compound (c1-1 1) is reacting with it. However, compounds (C1-12) and (C1-13) are different. If the compound has substituents, then compound (C1-11) and compound (C1-12) are combined. Alternatively, the reaction may be carried out and the product may be reacted with compound (C1-13), or in that manner This is preferable because it increases the yield and purity of the target product.

[0200] Next, as shown in the scheme below, from naphthalene compound (c1-14) to (c1-15) Halide naphthobisbenzofuran compounds or halide naphthobisbenzofuran compounds represented by Thiophene compounds can be obtained. Halogenation represented by the following general formula (c1-15) Naphthobisbenzofuran compounds or halogenated naphthobisbenzothiophene compounds, In the organic compound represented by the above general formula (B1-a1), R 12 and R 18 But halogen again This corresponds to an organic compound that has a sulfonyl group.

[0201] [ka]

[0202] This reaction can be carried out under various conditions. For example, naphthalene compounds (C1-14 ) is N-methylpyrrolidone (abbreviated as NMP) or dimethyl sulfoxide (abbreviated as DMSO) The reaction is carried out by dissolving it in a solution, and then adding potassium carbonate or cesium carbonate to the solution and heating it. It is possible to do so.

[0203] Next, we will explain other synthesis methods for the organic compound represented by the general formula (B1-a1) described above. The general formula (B1-a1) is shown below. Each substituent and X2 and X 3 Regarding that, see above This is the same as what was described. Furthermore, this synthesis method is R 14 and R 20 Compounds having substituents at the position It is preferable when it is a physical object. That is, R 14 and R 20 Each of them independently has 1 carbon atom. Hydrocarbon groups with up to 10 carbon atoms, halogen hydrocarbon groups with 3 to 10 carbon atoms, substituted or unsubstituted carbon atoms. One of 6 to 14 aromatic hydrocarbon groups, or any substituted or unsubstituted diarylamino groups. It is preferable that this be the case.

[0204] [ka]

[0205] As shown in the scheme below, naphthalene compounds (C1-21), aryl compounds (C1- 22) and aryl compounds (c1-23) are reacted to form (c1-24) A naphthalene compound can be obtained. 3 Ya Y 4 These are halogen groups such as chlorine and bromine. It represents a sulfonyl group. 3 Ya Y 4 The position shown is just one example, and in this synthesis example, the above general formula... (B1-a1) R 12 and R 18 Y at position 3 Ya Y 4 An example of introducing Y was shown, 3 Ya Y 4 is R 10 ~R 21 It can be introduced at any of the positions. Also, Y 3 Also is Y 4 It is acceptable to implement only one of them. 3 Ya Y 4 Change the installation location. This makes it possible to introduce substituents represented by (a2) above at various positions. Yes.

[0206] Also, Y 1 and Y 2 Y represents a halogen or sulfonyl group such as bromine or iodine. 1 Reach biY 2 is Y 3 Ya Y 4 A more reactive leaving group is preferred.

[0207] Furthermore, in the subsequent reactions, Y is selectively applied to the alpha position of the naphthalene ring of the naphthalene compound. 1 and Y 2 To react and cyclize, R 14 and R 20 It is a substituent other than hydrogen. This is preferable. Specifically, the naphthalene compound (c1-21) in the scheme below is R 1 4 and R 20 It is preferable that the organic compound has a substituent at the position indicated.

[0208] [ka]

[0209] This reaction can be carried out under various conditions. For example, naphthalene compounds (C1-21 ), aryl compounds (C1-22) and aryl compounds (C1-23) are N-methyl phosphate Dissolve it in rolidone (abbreviated as NMP) or dimethyl sulfoxide (abbreviated as DMSO), The reaction can be carried out by adding potassium carbonate or cesium carbonate to the solution and heating it. .

[0210] Here, compounds (c1-22) and (c1-23) are used simultaneously. 21) is reacting with compound (c1-22) and compound (c1-23) in different positions. If the compound has a commutative group, first, compound (c1-21) and compound (c1-22) are converted. The product may be reacted with compound (C1-23). ​​This is more effective for obtaining the desired product. This results in higher yield and purity, which is preferable.

[0211] Next, as shown in the scheme below, from the naphthalene compound (c1-24), (c1-15 ) represented by a halogenated naphthobisbenzofuran compound or halogenated naphthobisben Zothiophene compounds can be obtained. Halogens represented by the following general formulas (c1-15) Naphthobisbenzofuran compounds or halogenated naphthobisbenzothiophene compounds , in the organic compound represented by the above general formula (B1-a1), R 12 and R 18 but halogen These correspond to organic compounds that have a sulfonyl group.

[0212] [ka]

[0213] This reaction can be carried out under various conditions, but one example is using a metal catalyst in the presence of a base. There is a synthesis method that uses [a specific method]. A concrete example of this synthesis method is the Suzuki-Miyaura reaction. It is possible.

[0214] Next, we will explain the synthesis method of the organic compound represented by the general formula (B3-a1) mentioned above. The general formula (B3-a1) is shown below. Each substituent and X 2 and X 3 Regarding this, see the above. It is identical to that thing.

[0215] [ka]

[0216] As shown in the scheme below, a naphthalene compound (C3-11) and an aryl compound (C3 -12) By cross-coupling aryl compounds (C3-13), A naphthalene compound represented by (c3-14) can be obtained. 100 and R 10 1 Each of these represents an alkyl group such as a methyl group. 1 Ya B 2 These are boronic acid and diamine, respectively. Examples include lucoxyboronic acid. 3 Ya Y 4 These include chlorine, halogen groups such as bromine, and sulfon It represents the nyl group, etc. Note that Y 3 Ya Y 4 The position shown is just one example, and in this synthesis example, the above general formula (B R in 3-a1) 52 and R 58 Y at position 3 Ya Y 4 An example of introducing Y was shown, 3 or Y 4 is R 50 ~R 61 It can be introduced at any of the positions. Also, Y 3 or Y 4 It is acceptable to implement only one of them. 3 Ya Y 4 By changing the installation location Therefore, it becomes possible to introduce substituents represented by (a2) above at various positions.

[0217] Also, Y 1 and Y 2 Y represents a halogen or sulfonyl group such as bromine or iodine. 1 Reach biY 2 is Y3 Ya Y 4 A more reactive leaving group is preferred.

[0218] [ka]

[0219] This reaction can be carried out under various conditions, but one example is using a metal catalyst in the presence of a base. There is a synthesis method that uses [a specific method]. A concrete example of this synthesis method is the Suzuki-Miyaura reaction. It is possible.

[0220] Here, we will consider compound (c3-12) and compound (c3-13) simultaneously with compound (c3-1 1) is reacted with compound (C3-12) and compound (C3-13) but the substitutions are different. If the compound has a group, first react compound (C3-11) with compound (C3-12). Alternatively, the product may be reacted with compound (C3-13). This method may yield a higher yield of the desired product. The higher the ratio and purity, the better.

[0221] Next, as shown in the scheme below, the naphthalene compound (C3-14) is subjected to a dealkylation reaction. This allows us to obtain a naphthalene compound represented by (c3-15).

[0222] [ka]

[0223] This reaction can be carried out under various conditions, but one example is dichloromethane. Examples of reactions involving Lewis acids such as boron tribromide in solvents such as those mentioned above include:

[0224] Next, as shown in the scheme below, from the naphthalene compound (c3-15), (c3-16) Halide naphthobisbenzofuran compounds or halide naphthobisbenzofuran compounds represented by Thiophene compounds can be obtained. Organic compounds represented by the following general formula (c3-16) This refers to R in the organic compound represented by the above general formula (B3-a1). 52 and R 58 halogen Alternatively, it corresponds to an organic compound that has a sulfonyl group.

[0225] [ka]

[0226] This reaction can be carried out under various conditions. For example, naphthalene compounds (C3-15 ) is N-methylpyrrolidone (abbreviated as NMP) or dimethyl sulfoxide (abbreviated as DMSO) The reaction is carried out by dissolving it in a solution, and then adding potassium carbonate or cesium carbonate to the solution and heating it. It is possible to do so.

[0227] Next, we will explain other synthesis methods for the organic compound represented by the general formula (B3-a1) described above. The general formula (B3-a1) is shown below. Each substituent and X 2 and X 3 Regarding this, see above. It is identical to the beta product. Note that this synthesis method is R 54 and R 60 Compounds having substituents at the position This is preferable in the case of R 54 and R 60 Each of them independently has 1 or more carbon atoms. 10 hydrocarbon groups, halogen hydrocarbon groups with 3 to 10 carbon atoms, substituted or unsubstituted carbon atoms One of 6 to 14 aromatic hydrocarbon groups, or substituted or unsubstituted diarylamino groups It is preferable to have one.

[0228] [ka]

[0229] As shown in the scheme below, the dealkylation reaction of the naphthalene compound (C3-21) A naphthalene compound represented by (c3-22) can be obtained. 100 and R 1 01 Each of these represents an alkyl group, such as a methyl group.

[0230] Furthermore, in the subsequent reactions, Y is selectively applied to the beta position of the naphthalene ring of the naphthalene compound. 1 and Y 2 To react and cyclize, R 54 and R 60 It is a substituent other than hydrogen. This is preferable. Specifically, the naphthalene compound (c3-21) in the scheme below is R 5 4 and R 60 It is preferable that the organic compound has a substituent at the position indicated.

[0231] [ka]

[0232] This reaction can be carried out under various conditions, but one example is dichloromethane. Examples of reactions involving Lewis acids such as boron tribromide in solvents such as those mentioned above include:

[0233] Next, as shown in the scheme below, naphthalene compounds (C3-22), aryl compounds (C3-23) reacts with the aryl compound (C3-24) to produce (C3-2 A naphthalene compound represented by 5) can be obtained. 3 Ya Y 4 These include chlorine, bromine, etc. This represents halogen groups and sulfonyl groups. Note that Y 3 Ya Y 4 The position shown is just one example, and in this synthesis example... In the above general formula (B3-a1), R 52 and R 58 Y at position 3 Ya Y 4 An example of introducing this is shown. However, Y 3 Ya Y 4 is R 50 ~R 61 It can be installed in any of these positions. , Y 3 or Y 4 It is acceptable to implement only one of them. 3 Ya Y 4 Introduction By changing the position, substituents represented by (a2) above can be introduced to various positions. This becomes possible.

[0234] Also, Y 1 and Y 2 Y represents a halogen or sulfonyl group such as bromine or iodine. 1 Reach biY 2 is Y 3 Ya Y 4 A more reactive leaving group is preferred.

[0235] [ka]

[0236] This reaction can be carried out under various conditions. For example, N-methylpyrrolidone (abbreviated as: Potassium carbonate and carbonic acid in solutions such as NMP or dimethyl sulfoxide (DMSO) The reaction can be carried out by adding cesium and heating it.

[0237] Here, compound (c3-23) and compound (c3-24) are used simultaneously. 22) is reacting with it. However, compound (C3-23) and compound (C3-24) are different. If the compound has a substituent, then compound (C3-22) and compound (C3-23) First, the reaction may be carried out, and then the product may be reacted with compound (C3-24), or the This method is preferable because it results in a higher yield and purity of the target product.

[0238] Next, as shown in the scheme below, from the naphthalene compound (c3-25), (c3-16) Halide naphthobisbenzofuran compounds or halide naphthobisbenzofuran compounds represented by Thiophene compounds can be obtained. Halogenation represented by the following general formula (c3-16) Naphthobisbenzofuran compounds or halogenated naphthobisbenzothiophene compounds, In the organic compound represented by the above general formula (B3-a1), R 52 and R 58 But halogen again This corresponds to an organic compound that has a sulfonyl group.

[0239] [ka]

[0240] This reaction can be carried out under various conditions, but one example is using a metal catalyst in the presence of a base. There is a synthesis method that uses [a specific method]. A concrete example of this synthesis method is the Suzuki-Miyaura reaction. It is possible.

[0241] (Embodiment 2) An example of a light-emitting element, which is one aspect of the present invention, will be described in detail below with reference to Figure 1(A).

[0242] The light-emitting element in this embodiment comprises a pair of electrodes consisting of an anode 101 and a cathode 102, It consists of an EL layer 103 provided between the anode 101 and the cathode 102.

[0243] Anode 101 is a metal, alloy, or conductive compound with a large work function (specifically, 4.0 eV or more). It is preferable to form them using materials and mixtures thereof. Specifically, for example, Indium tin oxide (ITO), silicon, etc. Or silicon dioxide-containing indium oxide-tin oxide, indium oxide-zinc oxide, oxide Examples include indium oxide (IWZO) containing tungsten and zinc oxide. These conductive metal oxide films are usually deposited by sputtering, but sol- It is also acceptable to use methods such as the gel method for fabrication. An example of a fabrication method is indium oxide-acid Zinc oxide is a target made by adding 1 wt% to 20 wt% zinc oxide to indium oxide. Methods include forming it using sputtering with a tungsten tungsten. Indium oxide (IWZO) containing zinc oxide is compared to indium oxide with tan oxide. Contains 0.5 wt% to 5 wt% gusten and 0.1 wt% to 1 wt% zinc oxide. It can also be formed by sputtering using a target that has been prepared. In addition, gold ( Au, Platinum (Pt), Nickel (Ni), Tungsten (W), Chromium (Cr), Molybdenum Butene (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), a Examples include luminium (Al) or nitrides of metallic materials (e.g., titanium nitride). Furthermore, graphene can also be used. When using composite materials containing other substances, regardless of the work function, select electrode materials other than those mentioned above. You can also choose.

[0244] The hole injection layer 111 can be formed from a first material with relatively high acceptability. A composite material comprising a first substance having septal properties and a second substance having hole-transporting properties. It is preferable that it is formed by the above. Composite material is used as the material for the hole injection layer 111. In this case, the first substance is a substance that exhibits acceptability toward the second substance. When one substance extracts electrons from the second substance, electrons are generated in the first substance, and when electrons are extracted... A hole is generated in the second substance. The extracted electron and the generated hole are then subjected to an electric field, which causes an electron to be removed. The water flows to the anode 101, and the holes are injected into the light-emitting layer 113 via the hole transport layer 112, so It is possible to obtain light-emitting elements with low dynamic voltage.

[0245] The first substance is a transition metal oxide or a metal belonging to Group 4 through Group 8 of the periodic table. Oxides and organic compounds having electron-withdrawing groups (halogen groups or cyano groups) are preferred.

[0246] The above transition metal oxides are oxides of metals belonging to groups 4 through 8 of the periodic table. For example, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdic acid Oxides, tungsten oxide, manganese oxide, rhenium oxide, titanium oxide, ruthenium Zirconium oxide, hafnium oxide, and silver oxide have high acceptability. It is preferable. In particular, molybdenum oxide is stable in the atmosphere, has low hygroscopicity, and is easy to handle. It is suitable because it is easy to use.

[0247] Organic compounds having the above-mentioned electron-withdrawing groups (halogen groups or cyano groups) include 7,7,8,8- Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ) , chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12 -Hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexa Examples include fluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), etc. 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.

[0248] The second substance is a hole-transporting substance, 10 -6 cm 2 Hole mobility of / Vs or greater It is preferable that it has the following. The second material that can be used is N,N' -di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDP) PA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino ]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl) [amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-di Amine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenic acid) Aromatic amines such as 3-[N-phenylamino]benzene (abbreviation: DPA3B), 3-[N -(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole Bazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole- 3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) ), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino ]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazole (Lyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)f [phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-antryl) Phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazole) Carbazole derivatives such as zolyl)phenyl]-2,3,5,6-tetraphenylbenzene , 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-Bu DNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,1 0-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-ter t-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuD BA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diph Phenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation) :t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviated) Name: DMNA), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phen [Lu]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2 ,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6 ,7-Tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-biant Lyl, 10,10'-diphenyl-9,9'-biantryl, 10,10'-bis(2- Phenylphenyl)-9,9'-biantryl,10,10'-bis[(2,3,4,5 ,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetrace N, pentacene, coronene, rubren, perylene, 2,5,8,11-tetra(tert Examples include aromatic hydrocarbons such as butyl)perylene. Aromatic hydrocarbons have a vinyl skeleton. It may be done. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-vinyl group. Su(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4 Examples include -(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA). It can be done. Also, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphen 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-phenylfluoren-9-yl) truffle Phenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene -9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9 -phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1B) P), 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: PCBAN) B) 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl ru-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-fluore N-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H -Carbazole-3-yl)phenyl]-spiro-9,9'-bifluoren-2-amine Compounds having an aromatic amine skeleton, such as (abbreviation: PCBASF), 1,3-bis(N-ka Rubazolylbenzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (Abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarb Zol (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation) Compounds having a carbazole skeleton such as PCCP, 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-9 H-Fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DB) Compounds having a thiophene skeleton such as TFLP-IV, 4,4',4''-(benzene -1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{ 3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibene Compounds containing a furan skeleton, such as Zofuran (abbreviation: mmDBFFLBi-II), are used. This is possible. Among the above, compounds having an aromatic amine skeleton or a carbazole skeleton The compounds possess good reliability, high hole transport properties, and contribute to reducing the driving voltage. Therefore, it is preferable.

[0249] Furthermore, the organic compound according to one embodiment of the present invention is also a substance that has hole transport properties and can be used as a second substance. It is possible to be there.

[0250] Furthermore, the hole injection layer 111 can also be formed by a wet method. In this case, poly(ethylenedi) Oxythiophene / poly(styrene sulfonic acid) aqueous solution (PEDOT / PSS), poly Aniline / Campagne Sulfonic Acid Aqueous Solution (PANI / CSA), PTPDES, Et-P TPDEK, or PPBA, polyaniline / poly(styrene sulfonate)(PANI / Conductive polymer compounds with added acids such as PSS can be used.

[0251] The hole transport layer 112 is a layer containing a material having hole transport properties. As for the material, the same material as the second material listed above as the material constituting the hole injection layer 111 is used. It can be used. The hole transport layer 112 may be formed as a single layer or as multiple layers. It is acceptable if it is formed in multiple layers, to facilitate hole injection, The HOMO levels deepen in a stepwise manner, moving from the layer on the injection layer 111 side toward the layer on the emission layer 113 side. It is preferable that the configuration progresses in this way. Such a configuration is preferable for the host in the light-emitting layer 113. The material is highly suitable for blue fluorescent light-emitting devices with a deep HOMO level.

[0252] Furthermore, the hole transport layer 112 is deepened in a stepwise manner towards the light-emitting layer 113, with its HOMO level being adjusted accordingly. The configuration formed by multiple layers includes a hole injection layer 111, and an organic acceptor (the electron-withdrawing group described above). It is particularly suitable for devices formed from organic compounds (containing halogen groups or cyano groups), and This allows for the creation of a very good element with excellent rear injection characteristics and low drive voltage.

[0253] Furthermore, the organic compound according to one aspect of the present invention is also a substance that has hole transport properties, and has hole transport properties It can be used as a material.

[0254] The hole transport layer 112 can also be formed by a wet process. When forming, use poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyl Triphenylamine (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-di Phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacryl [Mido] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N Using polymer compounds such as '-bis(phenyl)benzidine' (abbreviation: Poly-TPD) It is possible.

[0255] The light-emitting layer 113 consists of a layer containing a fluorescent light-emitting material, a layer containing a phosphorescent light-emitting material, and a thermally activated delayed fluorescence ( Layers containing materials that emit TADF, layers containing quantum dots, and metal halogen perovskite The layer may contain any luminescent material, such as a layer containing threads, but this will be explained in Embodiment 1. It is preferable to include an organic compound according to one aspect of the present invention as a luminescent substance. By using organic compounds as luminescent materials, it is possible to achieve high efficiency and very high chromaticity. This makes it easier to obtain high-quality light-emitting elements.

[0256] Furthermore, the light-emitting layer 113 may be a single layer or consist of multiple layers. When forming a light-emitting layer, the layer containing phosphorescent material and the layer containing fluorescent material are stacked together. Layers may be used. In this case, the layer containing phosphorescent material utilizes the excitation complex described later. It is preferable to do so.

[0257] Furthermore, the organic compound according to one aspect of the present invention is also a substance that has a good quantum yield and is used as a luminescent material. It can be used.

[0258] Examples of fluorescent materials that can be used include the following: The following fluorescent luminescent substances can also be used: 5,6-bis[4-(10-phenyl-9-an [Tolyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[ 4'-(10-phenyl-9-antryl)biphenyl-4-yl]-2,2'-bipyri Zin (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9- Phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine, N,N '-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorine [Len-9-yl]phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPA) Prn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N '-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H- Luvazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10- Diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9- Diphenyl-N-[4-(10-phenyl-9-antryl)phenyl]-9H-carb Zole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(te) rt-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-antryl)- 4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: P) CBAPA), N,N''-(2-tert-butylanthracene-9,10-dibutyldi -4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine [Min] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl Lu-2-antryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAP) PA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N', N'-triphenyl-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- (9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole -3-amine (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 '-Triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10 -Bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl) Phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), Kumari N545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,1 2-Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviated) :BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methylaminophenyl) Chil-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2 -methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]k Noridine-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]fluoranthene- 3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2- (1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo [ij]Quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedi Nitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7 ,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quino Lysine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviated) Name: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]eth 2) Propanedinitrile (abbreviation: BisDCM), 2 -{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6, 7-Tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4 Examples include H-pyran-4-ylidene propanedinitrile (abbreviation: BisDCJTM). This is particularly true of pyrenediamine compounds such as 1,6mMemFLPAPrn. These condensed aromatic diamine compounds have high hole-trapping properties and excellent luminescence efficiency and reliability. Therefore, it is preferable.

[0259] Examples of materials that can be used as phosphorescent materials in the light-emitting layer 113 include, for example, Examples include the following: Tris{2-[5-(2-methylphenyl)-4-(2 ,6-dimethylphenyl)-4H-1,2,4-triazole-3-yl-κN2]phen Iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), Tri Su(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium( III) (abbreviation: [Ir(Mptz)3]), Tris[4-(3-biphenyl)-5-I Sopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) Abbreviated as [Ir(iPrptz-3b)3]), it has a 4H-triazole skeleton. iridium metal complexes and tris[3-methyl-1-(2-methylphenyl)-5-phenyl [Ir-1H-1,2,4-Triazolat] Iridium(III) (Abbreviation: [Ir(Mpt z1-mp)3]), Tris(1-methyl-5-phenyl-3-propyl-1H-1,2 ,4-Triazolat) Iridium(III) (Abbreviation: [Ir(Prptz1-Me)3] ) Organometallic iridium complexes having a 1H-triazole skeleton, such as fac-tris [1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole] Dium(III) (abbreviation: [Ir(iPrpmi)3]), Tris[3-(2,6-dimethyl (Tylphenyl)-7-methylimidazo[1,2-f]phenantridinato]iridium III) (abbreviation: [Ir(dmpimpt-Me)3]) has an imidazole skeleton organometallic iridium complexes and bis[2-(4',6'-difluorophenyl)pyridium Nato-N,C 2 '] Iridium(III) tetrakis(1-pyrazolyl) borate (abbreviation) :FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2 ' Iridium(III) picolinate (abbreviation: Firpic), bis{2-[3',5' -Bis(trifluoromethyl)phenyl]pyridinate-N,C 2 Iridium (III ) Picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), Bis[2-(4', 6'-Difluorophenyl)pyridinate-N,C 2 Iridium(III) acetylated Phenylpyridine derivatives with electron-withdrawing groups, such as setnat (abbreviated as FIracac). Examples include organometallic iridium complexes that use the iridium body as a ligand. These exhibit blue phosphorescence. It is a compound that has an emission spectrum peak between 440 nm and 520 nm. be.

[0260] 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 or more. It has an emission spectrum peak at 600 nm. Note that it is an organometallic compound with a pyrimidine skeleton. Iridium complexes are particularly preferred because they offer outstanding reliability and luminescence efficiency.

[0261] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrim [Dinato] Iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), Su[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Dium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di (Naphthalene-1-yl)pyrimidinato](Dipivaloylmethanato) Iridium (III) Organic compounds having a pyrimidine skeleton, such as (abbreviation: [Ir(d1npm)2(dpm)]) Metallic iridium complexes, and (acetylacetonato)bis(2,3,5-triphenylpyridine Nat(tppr)Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), Bis(2 ,3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III)( Abbreviation: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bi [Ir(4-fluorophenyl)quinoxalinato] Iridium(III) (abbreviation: [Ir(F Organometallic iridium complexes having a pyrazine skeleton such as dpq)2(acac)]), Tris(1-phenylisoquinolinato-N,C)2 ') Iridium (III) (abbreviation: [I r(piq)3]), bis(1-phenylisoquinolinato-N,C 2 ') Iridium (I II) Pyrrhizic acid like acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with a din skeleton, 2, 3, 7, 8, 12, 13, 17, 1 8-Octaethyl-21H,23H-Porphyrin Platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monof Phenanthroline Europium(III) (Abbreviation: [Eu(DBM)3(Phen)]) Tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monofena (Eu(TTA)3(Phen)) Examples include rare earth metal complexes. These are compounds that exhibit red phosphorescence, and 6 It has emission spectral peaks from 00 nm to 700 nm. It also possesses a pyrazine skeleton. The organometallic iridium complex yields a red emission with good chromaticity.

[0262] Furthermore, in addition to the phosphorescent compounds mentioned above, various phosphorescent light-emitting materials can also be selected and used. good.

[0263] TADF materials include fullerenes and their derivatives, acridines and their derivatives, and eosin. Magnesium derivatives can be used. Also, magnesium (Mg), zinc (Zn), cadmium Cd, tin (Sn), platinum (Pt), indium (In), or palladium ( Metal-containing porphyrins containing Pd, etc., can be used. For example, the protoporphyrin-tin fluoride complex (SnF) shown in the following structural formula 2(Proto IX)), Mesoporphyrin-Tin Fluoride Complex (SnF2(Meso IX), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro I II-4Me)), Octaethylporphyrin-Tin Fluoride Complex (SnF2(OEP)) , etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethyl phosphate Examples include rufirin-platinum chloride complex (PtCl2OEP).

[0264] [ka]

[0265] 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), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-3-yl) Luvazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated) Name: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl ]-4,6-diphenyl-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-di Methyl-9H-acridin-10-yl)-9H-xanthene-9-one (abbreviation: ACR) XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a π electrons such as clidine-9,9'-anthracene]-10'-one (abbreviated as ACRSA). Heterocyclic compounds containing both excess heteroaromatic rings and π-electron-deficient heteroaromatic rings can also be used. Yes, it is possible. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring. Therefore, it is preferable as it has high electron transport and hole transport properties. Substances in which a ring and a π-electron-deficient heteroaromatic ring are directly bonded are donors of π-electron-rich heteroaromatic rings. Both the sex and the acceptor nature of the π-electron-deficient complex aromatic ring become stronger, and the e of the S1 and T1 levels Because the energy difference becomes smaller, thermally activated delayed fluorescence can be obtained efficiently, which is particularly desirable. In addition, instead of a π-electron-deficient heteroaromatic ring, an electron-withdrawing group such as a cyano group may be attached. Aromatic rings may also be used.

[0266] [ka]

[0267] Furthermore, the quantum dots include elements from Group 14, Group 15, Group 16, and multiple elements from Group 14. Compounds consisting of group elements, compounds of elements belonging to groups 4 through 14 and group 16 elements, Compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, Group 13 Compounds of an element and a Group 17 element, compounds of a Group 14 element and a Group 15 element, Group 11 element Compounds with Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, various Examples of nano-sized particles include semiconductor clusters and metal halogen perovskites. can.

[0268] Specifically, cadmium selenide (CdSe), cadmium sulfide (CdS), and telluride Cadmium (CdTe), zinc selenide (ZnSe), zinc oxide (ZnO), zinc sulfide ( ZnS), zinc telluride (ZnTe), mercury sulfide (HgS), mercury selenide (HgSe) Mercury telluride (HgTe), indium arsenide (InAs), indium phosphide (InP ), gallium arsenide (GaAs), gallium phosphide (GaP), indium nitride (InN) Gallium nitride (GaN), indium antimonide (InSb), gallium antimonide Aluminum (GaSb), aluminum phosphide (AlP), aluminum arsenide (AlAs), aluminum Aluminum timonide (AlSb), lead(II) selenide (PbSe), lead(I) telluride I)(PbTe), lead(II) sulfide(PbS), indium selenide(In2Se3), Indium telluride (In2Te3), indium sulfide (In2S3), galium selenide (Ga2Se3), arsenic(III) sulfide (As2S3), arsenic(III) selenide (A s2Se3), arsenic(III) telluride (As2Te3), antimony(III) sulfide ( Sb2S3), antimony(III) selenide (Sb2Se3), antimony telluride ( (III)(Sb2Te3), bismuth(III)(Bi2S3) sulfide, bismuth selenide (III)(Bi2Se3), bismuth telluride (III)(Bi2Te3), silicon ( Si), silicon carbide (SiC), germanium (Ge), tin (Sn), selenium (Se), Tellurium (Te), boron (B), carbon (C), phosphorus (P), boron nitride (BN), phosphide Boron (BP), boron arsenide (BAs), aluminum nitride (AlN), aluminum sulfide Barium (Al2S3), barium sulfide (BaS), barium selenide (BaSe), telluride Barium (BaTe), calcium sulfide (CaS), calcium selenide (CaSe), Calcium telluride (CaTe), beryllium sulfide (BeS), beryllium selenide (B eSe), beryllium telluride (BeTe), magnesium sulfide (MgS), selenide Magnesium (MgSe), Germanium sulfide (GeS), Germanium selenide (GeS e) Germanium telluride (GeTe), tin(IV) sulfide (SnS2), tin(II) sulfide )(SnS), tin(II) selenide (SnSe), tin(II) telluride (SnTe), acid Lead(II) chloride (PbO), copper(I) fluoride (CuF), copper(I) chloride (CuCl), bromide Copper(I) (CuBr), copper(I) iodide (CuI), copper(I) oxide (Cu2O), selenium Copper(I) oxide (Cu2Se), nickel(II) oxide (NiO), cobalt(II) oxide ( CoO), cobalt(II) sulfide (CoS), triiron tetroxide (Fe3O4), iron(II) sulfide (FeS), manganese(II) oxide (MnO), molybdenum(IV) sulfide (MoS2) Vanadium(II) oxide (VO2), vanadium(IV) oxide (VO2), tungsten oxide Tene (IV) (WO2), tantalum (V) oxide (Ta2O5), titanium oxide (TiO2, Ti2O5, Ti2O3, Ti5O9, etc.), zirconium oxide (ZrO2), silicon nitride Element (Si3N4), germanium nitride (Ge3N4), aluminum oxide (Al2O3) Barium titanate (BaTiO3), a compound of selenium, zinc, and cadmium (CdZnS) e) Compounds of indium, arsenic, and phosphorus (InAsP), and compounds of cadmium, selenium, and sulfur. Compound (CdSeS), compound of cadmium, selenium, and tellurium (CdSeTe), indiu Compounds of indium, gallium, and arsenic (InGaAs), compounds of indium, gallium, and selenium (InGaSe), a compound of indium, selenium, and sulfur (InSeS), copper, and indium Examples include sulfur compounds (e.g., CuInS2) and combinations thereof. However, it is not limited to these. Also, there are so-called alloy-type quantum particles whose composition can be expressed in any ratio. You may also use a . For example, CdS x Se 1-x (where x is any number from 0 to 1) These alloy-type quantum dots can change their emission wavelength by changing x, so they emit blue light. It is one of the effective methods for obtaining light emission.

[0269] Quantum dot structures include core type, core-shell type, and core-multishell type. Either of these can be used, but another inorganic ion with a wider band gap can be used to cover the core. By forming a shell with the material, defects and dangling bones present on the nanocrystalline surface can be eliminated. The effects of the luminescence can be reduced. This greatly improves the quantum efficiency of the luminescence. It is preferable to use A-shell type or core-multi-shell type quantum dots. Examples of materials include zinc sulfide (ZnS) and zinc oxide (ZnO).

[0270] Furthermore, because quantum dots have a high proportion of surface atoms, they are highly reactive and prone to aggregation. Therefore, a protective agent is attached to the surface of the quantum dot or a protective group is provided. It is preferable that the protective agent is attached or a protective group is provided. This prevents aggregation and increases solubility in the solvent. Furthermore, it reduces reactivity and electrical... It is also possible to improve stability. Examples of protective agents (or protective groups) include polio Polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene Polyoxyethylene alkyl ethers such as ethylene oleyl ether, tripropyl phosphate Fins, tributylphosphine, trihexylphosphine, trioctylphosphine, etc. Trialkylphosphines, polyoxyethylene n-octylphenyl ether, polio Polyoxyethylene alkylphenyl ethers such as xyethylene n-nonylphenyl ether Tel compounds, tri(n-hexyl)amines, tri(n-octyl)amines, tri(n-decyl) ) Tertiary amines such as amines, tripropylphosphine oxide, tributylphosphine Oxide, trihexylphosphine oxide, trioctylphosphine oxide, tridec Organophosphorus compounds such as sylphosphine oxide, polyethylene glycol dilaurate, Polyethylene glycol diesters such as polyethylene glycol distearate, and Organic nitrogen compounds such as nitrogen-containing aromatic compounds like pyridine, lutidine, colidine, and quinolines. , hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine aminoalkanes such as hexadecylamine and octadecylamine, and dibutyl sulfide Dialkyl sulfides such as dipropyl sulfate, dipropyl sulfate such as dimethyl sulfoxide and dibutyl sulfoxide Organic sulfur compounds such as sulfur-containing aromatic compounds including sulfur sulfoxides and thiophenes, palmite Higher fatty acids such as tinic acid, stearic acid, and oleic acid, alcohols, and sorbitan fatty acid Polyesters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethylene Examples include mines, etc.

[0271] Note that the quantum dot may also be a rod-shaped quantum rod. The quantum rod is polarized in the c-axis direction. Because it exhibits light with a specific directionality, by using a quantum rod as the light-emitting material, This allows for the creation of a light-emitting element with good external quantum efficiency.

[0272] Furthermore, when forming a light-emitting layer by dispersing the quantum dots as a light-emitting material in a host, Disperse quantum dots in a host material, or dissolve the host material and quantum dots in a suitable liquid medium. Dissolve or disperse and perform wet processes (spin coating, casting, die coating, etc.) Roll coating method, inkjet method, printing method, spray coating method, car After forming a layer using methods such as the Tencoat method or the Langmuir-Bludget method, remove the liquid medium. It can be formed by removing or firing the material.

[0273] Examples of liquid media used in wet processes include methyl ethyl ketone and cyclohexyl ester. Ketones such as xanone, fatty acid esters such as ethyl acetate, and halogens such as dichlorobenzene Aromatic hydrocarbons such as toluene, xylene, mesitylene, and cyclohexylbenzene. Hydrocarbons, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, dimethylform Organic solvents such as humic acid (DMF) and dimethyl sulfoxide (DMSO) can be used. Cut.

[0274] When using a fluorescent material as the host material for the light-emitting layer, use 9-phenyl-3-[4 -(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCz) PA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (Abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]- 9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl) )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6 -[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[ 1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-furan) phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}anthracene (abbreviation) Materials having an anthracene skeleton, such as FLPPA, are preferred. When such a substance is used as a host material for a fluorescent material, it exhibits good luminescence efficiency and durability. Layers can be implemented, particularly CzPA, cgDBCzPA, and 2mBnfPPA. PCzPA exhibits very good characteristics, making it a preferred choice.

[0275] When using materials other than those mentioned above as host materials, materials with electron transport properties or hole transport properties may be used. Various carrier transport materials, including materials with specific properties, can be used.

[0276] Examples of materials with electron transport properties include bis(10-hydroxybenzo[h]quinoli Sodium beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolate) )(4-phenylphenolate)aluminum(III) (abbreviation: BAlq), bis(8- Zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) [Phenolate]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolate zinc(II) (abbreviation: ZnBTZ) and 2-(4-biphenyl Ryl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation) :PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butyl) Enyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl) Phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5 -Benzenetriyl)tris(1-phenyl-1H-benzoimidazole) (abbreviation: TP) BI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H -Polyazole skeletons such as benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds, and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]Quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothio [fen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2 mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)bipheni [Lu-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6 -Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn) P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation) Heterocyclic compounds having a diazine skeleton, such as 4,6 mDBTP2Pm-II, and 3,5 -Bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCz) PPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmP) Examples include heterocyclic compounds having a pyridine skeleton, such as yPB. Among those mentioned above, dia Heterocyclic compounds with a din skeleton or a pyridine skeleton are highly reliable. Yes, it is preferable. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are It has high electron transport properties and contributes to reducing the drive voltage.

[0277] Examples of materials with hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-fe [Nylamino]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 [Amino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene) 4-phenyl-3'-(9-9-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- Luvazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-na Phthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (Abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9) H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-di Methyl-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]spiro-9,9'-bifluore Compounds having an aromatic amine skeleton such as n-2-amine (abbreviation: PCBASF), and 1, 3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene Lyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9 -Phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-C) Compounds having a carbazole skeleton such as rubazole (abbreviated as PCCP), and 4,4', 4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DB) T3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene- 9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4- (9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothio Compounds containing a thiophene skeleton, such as Fen (abbreviation: DBTFLP-IV), and 4,4' ,4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF) 3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl The furan skeleton, such as phenyl dibenzofuran (abbreviation: mmDBFFLBi-II), Examples of compounds that possess this feature include compounds having an aromatic amine skeleton and carba. Compounds with a zole skeleton have good reliability and high hole transport properties, and the driving voltage It is preferable because it also contributes to reduction. In addition to the hole transport materials mentioned above, among various other materials... You may select and use a hole transport material from among them.

[0278] When using a fluorescent substance as the light-emitting material, use 9-phenyl-3-[4-(10-phenyl Nyl-9-antryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[ 4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCP) N), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazo CzPA (abbreviation: CzPA), 7-[4-(10-phenyl-9-antryl)phenyl]- 7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9, 10-Diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]f Ran (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H- Fluoren-9-yl)-biphenyl-4'-yl}-anthracene (abbreviation: FLPPA) Materials having an anthracene skeleton, such as those described above, are preferred. When used as a host material for light-emitting substances, it enables the creation of a light-emitting layer with excellent luminescence efficiency and durability. This is possible, especially with CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA. It exhibits very good characteristics, making it a preferred choice.

[0279] The host material may be a mixture of multiple substances, and the mixed host material When using this method, mix an electron-transporting material with a hole-transporting material. This is preferable. By mixing an electron-transporting material with a hole-transporting material This allows for easy adjustment of the transport properties of the light-emitting layer 113, and also enables simple control of the recombination region. It is possible. The ratio of the content of hole-transporting material to electron-transporting material is the ratio of hole-transporting material. The ratio of transportable material to electron-transportable material should be 1:9 to 9:1.

[0280] Furthermore, these mixed host materials may form excited complexes. These excited complexes are The wavelength of the lowest energy absorption band of fluorescent materials, phosphorescent materials, and TADF materials By selecting combinations that form excitation complexes that exhibit overlapping luminescence, energy Energy transfer becomes smoother, and light emission can be obtained more efficiently. Furthermore, this configuration is This is preferable because it can also reduce dynamic voltage.

[0281] The light-emitting layer 113 having the above configuration can be produced by co-deposition using vacuum deposition or by using a mixed solution. Methods include gravure printing, offset printing, inkjet printing, spin coating, and It can be manufactured using methods such as dip coating.

[0282] The electron transport layer 114 is a layer containing a substance that has electron transport properties. Examples include electron-transporting materials that can be used as the host material, and anthrace Materials having a skeletal structure can be used.

[0283] Furthermore, a layer for controlling the movement of electron carriers may be provided between the electron transport layer and the light-emitting layer. This involves adding a small amount of a substance with high electron-trapping properties to a material with high electron-transporting properties as described above. It is a layer that regulates carrier balance by suppressing the movement of electron carriers. This becomes possible. This configuration occurs when electrons penetrate the light-emitting layer. It is highly effective in suppressing problems such as reduced device lifespan.

[0284] Furthermore, an electron injection layer 115 is placed between the electron transport layer 114 and the cathode 102, in contact with the cathode 102. It may be provided. The electron injection layer 115 may be lithium fluoride (LiF) or cesium fluoride. Alkali metals or alkaline earth metals such as calcium fluoride (CaF2), (CsF), etc. The genus or compounds thereof can be used. For example, a substance having electron transport properties. A layer containing alkali metals, alkaline earth metals, or compounds thereof is used. This is possible. Furthermore, an electride may be used in the electron injection layer 115. For example, a mixture of calcium and aluminum oxide with a high concentration of electrons added. Quality and other factors are mentioned. Furthermore, the electron injection layer 115 is a layer made of a material that has electron transport properties. By using one containing an alkali metal or alkaline earth metal, the cathode 10 This is preferable because electron injection from 2 is performed efficiently.

[0285] 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 above-mentioned acceptor material and a hole transport material. It may also be constructed by laminating a film containing a material. By applying a potential to the P-type layer 117, Electrons are injected into the electron transport layer 114 and holes into the cathode 102, causing the light-emitting element to operate. The electron transport layer 114 contains an organic compound according to one embodiment of the present invention at a position in contact with the charge generation layer 116. The presence of this layer suppresses the decrease in brightness that occurs due to the accumulation of operating time of the light-emitting element, extending its lifespan. This allows for the creation of light-emitting elements with long lifespans.

[0286] 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.

[0287] 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 this is between the LUMO level of the material contained in the layer in contact with it. Electron relay layer 1 Specific energy levels of LUMO levels in electron-transporting materials used in 18 The voltage should be -5.0 eV or higher, preferably -5.0 eV to -3.0 eV. Oh, as for electron-transporting materials used in the electron relay layer 118, phthalocyanine-based It is preferable to use a material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0288] 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)).

[0289] 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.

[0290] As the material that forms cathode 102, gold with a small work function (specifically, 3.8 eV or less) is used. Compounds, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of cathode materials include alkali metals such as lithium (Li) and cesium (Cs). , and elements such as magnesium (Mg), calcium (Ca), and strontium (Sr). Elements belonging to Group 1 or Group 2 of the periodic table, and alloys containing them (MgAg, AlL i) Rare earth metals such as europium (Eu) and ytterbium (Yb), and those containing these Examples include alloys, etc. However, between the cathode 102 and the electron transport layer, an electron injection layer is provided. By providing this, regardless of the magnitude of the work function, Al, Ag, ITO, silicon, or acid Various conductive materials such as indium oxide-tin oxide containing silicon dioxide are used as cathode 102. These conductive materials can be produced using dry methods such as vacuum deposition and sputtering. It is possible to deposit films using methods such as inkjet printing and spin coating. Furthermore, sol- It may be formed by a wet process using the gel method, or by forming it by a wet process using a paste of a metal material. That's fine.

[0291] Various methods can be used to form the EL layer 103, regardless of whether they are dry or wet methods. Yes, it is possible. For example, vacuum deposition and wet process methods (spin coating, casting, die coating). Coating method, blade coating method, roll coating method, inkjet method, printing method (gravure printing) Printing methods (offset printing, screen printing, etc.), spray coating, curtain coating You may also use methods such as the Langmuir-Bludget method.

[0292] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0293] Here, we will use Figure 2 to describe a method for forming a layer 786 containing a light-emitting material using the droplet ejection method. Let me explain. Figures 2(A) to 2(D) illustrate the method for fabricating the layer 786 containing the luminescent material. This is a cross-sectional view.

[0294] First, a conductive film 772 is formed on the planar insulating film 770, and a portion of the conductive film 772 is covered An insulating film 730 is formed thereon (see Figure 2(A)).

[0295] Next, droplets are dispensed from the droplet dispensing device 783 onto the exposed portion of the conductive film 772, which is an opening in the insulating film 730. 784 is dispensed to form a layer 785 containing the composition. The droplet 784 contains the solvent-containing composition. Yes, it adheres to the conductive film 772 (see Figure 2(B)).

[0296] The process of dispensing the droplet 784 may also be carried out under reduced pressure.

[0297] Next, the solvent is removed from layer 785 containing the composition and solidified to form a layer containing the luminescent material. Forms 786 (see Figure 2(C)).

[0298] The solvent can be removed by either a drying or heating process.

[0299] Next, a conductive film 788 is formed on the layer 786 containing the light-emitting material to form a light-emitting element 782. See Figure 2(D).

[0300] When a layer 786 containing a light-emitting substance is formed by droplet ejection in this manner, the composition is selectively ejected. This allows for reducing material waste. Also, it is possible to process the shape. Since lithography is not required, the process can be simplified, resulting in lower costs. can.

[0301] The droplet dispensing method described above refers to a nozzle having a dispensing port for the composition, or one or This term refers to devices that have means for dispensing droplets, such as heads with multiple nozzles.

[0302] Next, the droplet dispensing device used in the droplet dispensing method will be explained using Figure 3. Figure 3 shows droplets This is a conceptual diagram illustrating the discharge device 1400.

[0303] The droplet dispensing device 1400 has a droplet dispensing means 1403. It has head 1405, head 1412, and head 1416.

[0304] Heads 1405 and 1412 are connected to control means 1407, which then processes them using a computer. By controlling it with the TA1410, it is possible to draw on a pre-programmed pattern. Cut.

[0305] Furthermore, as for the timing of drawing, for example, the marker 14 formed on the substrate 1402 You can use 11 as the reference point. Alternatively, you can determine the reference point by using the outer edge of substrate 1402 as the reference point. It is also acceptable. Here, the marker 1411 is detected by the imaging means 1404, and the image processing means 14 The signal converted to digital in step 09 is recognized by computer 1410, which then generates a control signal. Then send it to control means 1407.

[0306] The imaging means 1404 may include a charge-coupled device (CCD) or a complementary metal-oxide-semiconductor (C) Image sensors using MOS (Motion Sensors) can be used. The information of the pattern to be formed is stored in the storage medium 1408, and this information Based on this, a control signal is sent to the control means 1407, and the individual heads 14 of the droplet dispensing means 1403 Heads 1412 and 1416 can be controlled individually. The material to be dispensed is From material supply sources 1413, 1414, and 1415, through the piping to the head It is supplied to head 1405, head 1412, and head 1416, respectively.

[0307] The interior of heads 1405, 1412, and 1416 is as shown by the dotted line 1406. It has a structure that includes a space for filling with liquid material and a nozzle that serves as the discharge port. However, head 1412 has the same internal structure as head 1405. By providing nozzles of different sizes for the 1412, it is possible to draw different materials simultaneously with different widths. It is possible to eject and draw with multiple types of light-emitting materials using a single head. This is possible, and when drawing over a wide area, multiple nozzles are used to improve throughput. It can simultaneously dispense and draw materials. When using a large substrate, head 1405, Heads 1412 and 1416 move on the circuit board in the directions of the X, Y, and Z arrows shown in Figure 3. The area to be scanned and drawn can be freely set, and the same pattern can be repeated on a single substrate. Numbers can be drawn.

[0308] Furthermore, the process of extruding the composition may be carried out under reduced pressure. The substrate may be heated during extruding. Alternatively, after the composition is extruded, one or both of the drying and / or calcination steps are performed. Both processes involve heat treatment, but their purpose, temperature, and time differ. The firing process is carried out under normal or reduced pressure using laser irradiation, instantaneous heat annealing, or heating furnaces. This is done by methods such as those listed above. However, the timing and number of times this heat treatment is performed are not particularly limited. No. In order to carry out the drying and firing processes properly, the temperature at that time depends on the material and composition of the substrate. It depends on the properties of the material.

[0309] As described above, a layer 786 containing a light-emitting substance can be fabricated using a droplet dispensing device.

[0310] When producing a layer 786 containing a light-emitting substance using a droplet ejection device, various organic materials and A wet method using a composition obtained by dissolving or dispersing organic-inorganic halogen perovskites in a solvent. When formed by the above, various organic solvents can be used to make a coating composition. Organic solvents that can be used in the product include benzene, toluene, xylene, and methylcellulose. N, tetrahydrofuran, dioxane, ethanol, methanol, n-propanol, i Sopropanol, n-butanol, t-butanol, acetonitrile, dimethyl sulfoxide HCl, dimethylformamide, chloroform, methylene chloride, carbon tetrachloride, acetate Various organic solvents such as benzoyl hydrate, hexane, and cyclohexane can be used. In particular, benzyl hydrate By using low-polarity benzene derivatives such as toluene, xylene, and mesitylene, It is possible to create a solution of a certain concentration, and the materials contained in the ink will not deteriorate due to oxidation, etc. This is preferable because it prevents the following: Furthermore, it takes into account the uniformity of the film after fabrication and the uniformity of the film thickness. Then, it is preferable that the boiling point is 100°C or higher, and toluene, xylene, and mesitylene are further It is preferable.

[0311] The above configuration may be combined with other embodiments or other configurations within this embodiment as appropriate. This is possible.

[0312] Next, we will discuss the configuration of a light-emitting element (also called a stacked element) in which multiple light-emitting units are stacked. This will be explained with reference to Figure 1(C). This light-emitting element has multiple elements between the anode and the cathode. This is a light-emitting element having a light-emitting unit. One light-emitting unit is the EL shown in Figure 1(A). It has a similar configuration to layer 103. In other words, the light-emitting element shown in Figure 1(A) or Figure 1(B) is The light-emitting element has one light-emitting unit, and the light-emitting element shown in Figure 1(C) has multiple light-emitting units. It can be described as a light-emitting element having a light unit.

[0313] In Figure 1(C), a first light-emitting unit is placed between the first electrode 501 and the second electrode 502. The first light-emitting unit 511 and the second light-emitting unit 512 are stacked, and the first light-emitting unit 511 and A charge generation layer 513 is provided between the first electrode 5 and the second light-emitting unit 512. 01 and the second electrode 502 correspond to the anode 101 and cathode 102 in Figure 1(A), respectively. The same thing described in the explanation of Figure 1(A) can be applied. Also, the first light emission Whether unit 511 and the second light-emitting unit 512 have the same configuration or different configurations good.

[0314] When a voltage is applied to the first electrode 501 and the second electrode 502, the charge generation layer 513 generates a charge. It has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. In other words, in Figure 1(C), the potential of the first electrode is higher than the potential of the second electrode. When a voltage is applied in this manner, the charge generation layer 513 generates electrons in the first light-emitting unit 511. Any method that injects a hole into the second light-emitting unit 512 is acceptable.

[0315] 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.

[0316] Furthermore, if an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer layer is located on the anode side. Because it plays the role of an electron injection layer in the light unit, it is not necessarily superimposed on the light-emitting unit. There is no need to form an electron injection layer.

[0317] Figure 1(C) illustrates a light-emitting element having two light-emitting units, but there are three or more The same configuration can also be applied to light-emitting elements formed by stacking light-emitting units. As in the light-emitting element according to this embodiment, multiple light-emitting units are charged between a pair of electrodes. By separating and arranging the elements with the blue layer 513, high-brightness light emission is possible while maintaining a low current density. Furthermore, it enables the creation of elements with an even longer lifespan. In addition, it allows for low-voltage operation and low power consumption of light-emitting devices. This makes placement possible.

[0318] Furthermore, by making the light-emitting color of each light-emitting unit different, the entire light-emitting element... This allows you to obtain light emission of the desired color.

[0319] (Embodiment 3) This embodiment describes a light-emitting device using the light-emitting element described in Embodiment 1.

[0320] A light-emitting device according to one aspect of the present invention will be described with reference to Figure 4. Figure 4(A) shows the light-emitting device. Figure 4(B) is a top view showing the position, and Figure 4(A) is a cross-sectional view obtained by cutting along AB and CD. This light-emitting device controls the light emission of the light-emitting element, and the drive circuit section shown by the dotted line ( Includes source line drive circuit 601, pixel section 602, and drive circuit section (gate line drive circuit) 603. It is. Also, 604 is the sealing substrate, and 605 is the sealing material, and it is surrounded by the sealing material 605. The inside of this space is 607.

[0321] 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.

[0322] Next, the cross-sectional structure will be explained using Figure 4(B). The drive circuit section is located on the element substrate 610. And a pixel section is formed, but here, the source line drive circuit 601 which is the drive circuit section and One pixel in the pixel section 602 is shown.

[0323] The source line drive circuit 601 consists of an n-channel FET 623 and a p-channel FET 624. A CMOS circuit is formed by combining these. Furthermore, the drive circuit consists of various CMOS circuits. It may be formed using PMOS or NMOS circuits. In this embodiment, on the substrate This shows a driver-integrated type with a drive circuit formed therein, but this is not necessarily required, and the drive circuit is based It can also be formed on the outside rather than on the board.

[0324] 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.

[0325] There are no particular limitations on the type and crystallinity of semiconductors used in FETs; amorphous semiconductors are used. Alternatively, a crystalline semiconductor may be used. An example of a semiconductor used in an FET is the 13th Using Group 14 semiconductors, Group 14 semiconductors, compound semiconductors, oxide semiconductors, and organic semiconductor materials. This is possible, but it is particularly preferable to use an oxide semiconductor. Examples of such oxide semiconductors include In-Ga oxide, In-M-Zn oxide (where M is Al, Ga, Y, Zr, La, Ce) Examples include , or Nd). Furthermore, the energy gap is 2eV or more, preferably 2 Using an oxide semiconductor material with a voltage of 0.5 eV or higher, and more preferably 3 eV or higher, is possible. This is preferable because it can reduce the off-current of the zista.

[0326] 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.

[0327] Furthermore, in order to ensure good coverage, the upper or lower end of the insulator 614 has a curvature. A curved surface is formed. For example, as the material for the insulator 614, a positive-type photosensitive aluminum When using rill resin, the radius of curvature (0.2 μm to 3 μm) is only at the upper end of the insulator 614. It is preferable to give it a curved surface having the following characteristics. Also, as the insulator 614, a negative-type photosensitive resin Either a fat or a positive-type photosensitive resin can be used.

[0328] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. These are the anode 101, EL layer 103, and cathode 10, respectively, as explained in Figures 1(A) and (B). 2 or the first electrode 501, EL layer 503 and second electrode 502 as described in Figure 1(C) It is correct.

[0329] The EL layer 616 preferably contains an organometallic complex. The organometallic complex is the light-emitting layer. It is preferable to use it as a luminescence central material in the context of [the application of this technology].

[0330] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, A light-emitting element 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 618. Furthermore, the space 607 is filled with a filler material. In addition to cases where an inert gas (such as nitrogen or argon) is used for filling, the sealant 605 is used for filling. In some cases, a recess is formed in the encapsulating substrate and a desiccant is placed there, which can lead to deterioration due to moisture. This can be suppressed, which is preferable.

[0331] It is preferable to use epoxy resin or glass frit for the sealant 605. These materials should preferably be as impermeable to moisture and oxygen as possible. In addition to glass substrates and quartz substrates, FRP (F) is also used as a material for the plate 610 and the sealing substrate 604. Polyvinyl Fluoride (PVF), Reinforced Plastics ), a plastic substrate made of polyester or acrylic resin can be used. .

[0332] For example, in this specification, transistors and light-emitting elements are formed using various substrates. It is possible. The type of circuit board is not limited to a specific one. As an example of such a circuit board... For example, semiconductor substrates (e.g., single crystal substrates or silicon substrates), SOI substrates, glass substrates, and stone British circuit boards, plastic circuit boards, metal circuit boards, stainless steel circuit boards, stainless steel... Substrate with foil, tungsten substrate, substrate with tungsten foil, flexible group Examples include sheets, laminated films, paper containing fibrous materials, or base films. Examples of substrates include barium borosilicate glass, aluminobrosilicate glass, or saw Examples include dalime glass. Examples include flexible substrates, laminated films, and base films. Examples include the following: For example, polyethylene terephthalate (PET), Polyethylene naphthalate (PEN) and polyethersulfone (PES) are representative examples. There is plastic. Or, for example, there is synthetic resin such as acrylic resin. For example, polytetrafluoroethylene (PTFE), polypropylene, and poly Examples include esters, polyvinyl fluoride, or polyvinyl chloride. Alternatively, as an example, Examples include polyamides, polyimides, aramids, epoxy, inorganic vapor-deposited films, and paper. In particular, the manufacturing of transistors using semiconductor substrates, single crystal substrates, or SOI substrates. This results in less variation in characteristics, size, or shape, and high current capacity. It is possible to manufacture transistors with small dimensions. Such transistors can be used in circuits. By configuring it this way, it is possible to reduce the power consumption of the circuit or increase the integration of the circuit.

[0333] Furthermore, a flexible substrate is used as the substrate, and transistors and light-emitting elements are directly mounted on the flexible substrate. Alternatively, a release layer may be formed between the substrate and the transistor, or between the substrate and the light-emitting element. It may be done. The delamination layer is applied to the substrate after the semiconductor device has been partially or completely completed on it. It can be separated and used to transfer to another substrate. In this case, the transistor has heat resistance. It can also be transferred to substrates with inferior properties or flexible substrates. Furthermore, the aforementioned release layer can be, for example, tungsten. The structure of an inorganic film layered with a silicon oxide film, or an organic resin such as polyimide on a substrate. A structure in which a lipid film is formed can be used.

[0334] In other words, transistors and light-emitting elements are formed using one substrate, and then transistors are transferred to another substrate. The transistors and light-emitting elements may be relocated and placed on a different substrate. An example of a substrate on which transistors or light-emitting elements are transposed is the one on which the above-mentioned transistors are formed. In addition to substrates that can be used, paper substrates, cellophane substrates, aramid film substrates, and polyimide substrates are also available. Film substrates, stone substrates, wood substrates, cloth substrates (natural fibers (silk, cotton, hemp), synthetic fibers (nails) (Iron, polyurethane, polyester) or regenerated fibers (acetate, cupro, rayon) These include yon, recycled polyester, etc., leather substrates, or rubber substrates. By using a substrate, it is possible to form transistors with good characteristics and transistors with low power consumption. It is possible to form a tangible structure, manufacture a durable device, provide heat resistance, reduce weight, or make it thinner. ru.

[0335] Figure 5 shows a light-emitting element that emits white light, with a colored layer (color filter) provided. An example of a light-emitting device that has been made full-color is shown. Figure 5(A) shows the substrate 1001 and the underlying insulation. Film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, first Interlayer insulating film 1020, second interlayer insulating film 1021, peripheral portion 1042, pixel portion 1040, drive Dynamic circuit section 1041, first electrodes 1024W, 1024R, 1024G, 102 4B, partition wall 1025, EL layer 1028, cathode of light-emitting element 1029, sealing substrate 1031, Materials such as 1032 are shown in the illustration.

[0336] Furthermore, Figure 5(A) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer (1034B) is provided on the transparent substrate 1033. In addition, the black layer (black matrix A rix) 1035 may be further provided. A transparent substrate 1 having a colored layer and a black layer. 033 is aligned and fixed to the substrate 1001. Note that the colored layer and the black layer are O It is covered with a bar coat layer 1036. Also, in Figure 5(A), light is transmitted through the colored layer. There are two types of light-emitting layers: one that emits light to the outside without passing through, and another that emits light to the outside by passing through the colored layers of each color. Light that does not pass through the colored layer is white, and light that passes through the colored layer is red, blue, and green, thus creating a four-color image. It can express images naturally.

[0337] Figure 5(B) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer Example of forming layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. This was shown. Thus, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's good too.

[0338] Furthermore, in the light-emitting device described above, light is taken to the substrate 1001 side on which the FET is formed. Although a light-emitting device with a bottom-emission structure was used, the light emission was taken from the sealing substrate 1031 side. It can also be used as a light-emitting device with a projection structure (top emission type). A cross-sectional view of the light-emitting device is shown in Figure 6. In this case, the substrate 1001 is a substrate that does not transmit light. This can be done. Until the connecting electrode that connects the FET and the anode of the light-emitting element is fabricated, the bottom edge It is formed in the same way as a mission-type light-emitting device. Then, the third interlayer insulating film 1037 is attached to electrode 1 It is formed by covering 022. This insulating film may also play a planar role. Third interlayer insulating The border film 1037 can be formed using the same material as the second interlayer insulating film, as well as various other materials. It is possible.

[0339] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are the anodes here. However, it can also be a cathode. Also, a top-emission type light-emitting device as shown in Figure 6. In this case, it is preferable that the first electrode be a reflective electrode. The configuration of the EL layer 1028 is as follows: As explained in Figures 1(A) and (B) as EL layer 103 or Figure 1(C) as EL layer 503 The device has a configuration that allows for the emission of white light.

[0340] In the top emission structure shown in Figure 6, the colored layer (red colored layer 1034R, green colored layer) The sealing is performed using a sealing substrate 1031 having a color layer 1034G and a blue colored layer 1034B. This can be done. The encapsulating substrate 1031 has a black layer (black mark) positioned between the pixels. A trix (1035) may be provided. Colored layer (red colored layer 1034R, green colored layer 1034G, the blue colored layer (1034B), and the black layer are covered by an overcoat layer. It is also acceptable to do so. Furthermore, the sealing substrate 1031 shall be a light-transmitting substrate.

[0341] 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 three colors (red, green, and blue) or four colors (red, green, blue, and yellow).

[0342] Figure 7 shows a passive matrix type light-emitting device, which is one embodiment of the present invention. Figure 7(A) is a perspective view showing the light-emitting device, and Figure 7(B) is a cross-sectional view of Figure 7(A) cut along the X and Y lines. In Figure 7, on the substrate 951, an EL layer 955 is placed between electrode 952 and electrode 956. It is provided. The end of the electrode 952 is covered with an insulating layer 953. And the insulating layer 95 A partition layer 954 is provided on 3. The side walls of the partition layer 954 become closer to the substrate surface This means that it has a slope such that the distance between one side wall and the other side wall becomes narrower. The cross-section of the partition layer 954 in the short-side direction is trapezoidal, and the base (similar to the surface direction of the insulating layer 953) The side facing the direction and in contact with the insulating layer 953 is the upper side (in the same direction as the surface direction of the insulating layer 953). It faces in a direction that is shorter than the side that does not come into contact with the insulating layer 953. In this way, the partition layer 954 is provided. This prevents defects in the light-emitting element caused by static electricity, etc.

[0343] The light-emitting device described above has a large number of tiny light-emitting elements arranged in a matrix, which form the pixel section Since each FET can be controlled by the FETs formed therein, the display device that represents the image This is a light-emitting device that can be suitably used as a placement device.

[0344] Lighting equipment A lighting device according to one aspect of the present invention will be described with reference to Figure 8. Figure 8(B) shows the lighting device. The top view, Figure 8(A), is a cross-sectional view of ef in Figure 8(B).

[0345] The lighting device has a first electrode 401 formed on a translucent substrate 400 which serves as a support. The first electrode 401 corresponds to the anode 101 in Figures 1(A) and (B). When light emission is extracted from the electrode 401 side, the first electrode 401 is formed from a light-transmitting material. do.

[0346] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0347] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is shown in Figure 1(A), ( This corresponds to EL layer 103 in B) or EL layer 503 in Figure 1(C), etc. Please refer to the relevant description for further details.

[0348] The second electrode 404 is formed by covering the EL layer 403. The second electrode 404 is shown in Figure 1(A), ( This corresponds to cathode 102 in B). When light emission is taken from the first electrode 401 side, the second electrode 404 is formed from a material with high reflectivity. The second electrode 404 is connected to the pad 412. Voltage is supplied by doing so.

[0349] A light-emitting element is formed by the first electrode 401, the EL layer 403, and the second electrode 404. The light-emitting element and the sealing substrate 407 are fixed and sealed using sealing materials 405 and 406. The lighting device is completed by doing this. Either sealing material 405 or 406 is acceptable. Furthermore, a desiccant can be mixed into the inner sealant 406, thereby absorbing moisture. It can be worn, leading to improved reliability.

[0350] Furthermore, the pad 412 and a portion of the first electrode 401 are extended outside the sealing materials 405 and 406. By providing this, it can be used as an external input terminal. Furthermore, a converter or similar device can be placed on top of it. An IC chip 420 or similar, which incorporates this technology, may also be provided.

[0351] ≪Electronic equipment≫ An example of an electronic device according to one aspect of the present invention will be described. An example of an electronic device is a television. Television equipment (also called television or television receiver), monitors for computers, etc. Digital cameras, digital video cameras, digital photo frames, mobile phones (portable) (Also called a mobile phone or cell phone device), portable game console, personal digital assistant, sound playback device, pachinko Examples include large game consoles such as pachinko machines. Specific examples of these electronic devices are shown below.

[0352] Figure 9(A) shows an example of a television system. The television system has a housing 710 The display unit 7103 is incorporated into part 1. Also, the housing is connected by the stand 7105. This shows the configuration supporting 7101. The display unit 7103 can display video. The display unit 7103 is configured by arranging light-emitting elements in a matrix.

[0353] 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.

[0354] 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.

[0355] Figure 9(B1) is a computer, consisting of the main unit 7201, the casing 7202, the display unit 7203, and a key - Includes board 7204, external connection port 7205, pointing device 7206, etc. Furthermore, this computer uses a matrix arrangement of light-emitting elements in the display unit 7203. It is manufactured by doing so. The computer in Figure 9(B1) is in the form shown in Figure 9(B2) It's fine to have it. The computer in Figure 9 (B2) has a keyboard 7204, a pointing desk A second display unit 7210 is provided in place of the vice 7206. Second display unit 721 0 is a touch panel type, and the input display shown on the second display unit 7210 points to the input display. Input can be performed by operating with a dedicated pen. Also, the second display unit 72 Unit 10 can display not only input but also other images. Also, the display unit 7 The 203 could also be a touchscreen. The two screens are connected by a hinge. This also prevents problems such as scratching or damaging the screen during storage or transport. It is possible.

[0356] Figures 9(C) and 9(D) show an example of a personal digital assistant (PDTA). The PDTA is housed in casing 7401. In addition to the display unit 7402 incorporated into it, there are operation buttons 7403, an external connection port 7404, and It is equipped with a Pika 7405, a Mic 7406, etc. Furthermore, the portable information terminal uses a light-emitting element. It has a display unit 7402 that is made by arranging the components in a matrix.

[0357] The portable information terminal shown in Figures 9(C) and (D) allows the user to touch the display unit 7402 with their finger or the like. It can also be configured to allow information to be entered. In this case, you can make a phone call, or Operations such as composing an email can be performed by touching the display unit 7402 with your finger. can.

[0358] 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.

[0359] 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.

[0360] Furthermore, the mobile information terminal has sensors that detect tilt, such as a gyroscope and an accelerometer. By providing a detection device, the orientation of the mobile information terminal (portrait or landscape) is determined, and the display unit 7402 The screen display can be set to switch automatically.

[0361] 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.

[0362] 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.

[0363] 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.

[0364] Furthermore, the above-mentioned electronic device can be used by appropriately combining the configurations shown in this specification. .

[0365] Furthermore, it is preferable to use a light-emitting element according to one embodiment of the present invention in the display unit. The light-emitting element emits light. It is possible to create a light-emitting element with good efficiency. Furthermore, it is possible to create a light-emitting element with a low driving voltage. This makes it possible. For this reason, an electronic device including a light-emitting element according to one aspect of the present invention has low power consumption. It can be used as an electronic device.

[0366] Figure 10 shows an example of a liquid crystal display device in which a light-emitting element is applied as a backlight. The liquid crystal display device consists of a housing 901, a liquid crystal layer 902, a backlight unit 903, and a housing 90 It has 4, and the liquid crystal layer 902 is connected to the driver IC 905. Backlight unit A light-emitting element is used in terminal 903, and current is supplied to it via terminal 906.

[0367] It is preferable to use a light-emitting element according to one aspect of the present invention, and the light-emitting element is used in a liquid crystal display. By applying this to the backlight of a display device, a backlight with reduced power consumption can be obtained. It can be done.

[0368] Figure 11 shows an example of a desk lamp according to one aspect of the present invention. The desk lamp shown in Figure 11 is A lighting device comprising a housing 2001 and a light source 2002, wherein the light source 2002 is a light-emitting element. It is being used.

[0369] Figure 12 shows an example of an indoor lighting device 3001. This lighting device 3001 is an embodiment of the present invention. It is preferable to use a light-emitting element of a certain type.

[0370] Figure 13 shows an automobile according to one aspect of the present invention. This automobile has a windshield and a dashboard. The unit is equipped with a light-emitting element. Display areas 5000 to 5005 are equipped with light-emitting elements. This is a display area provided using a light-emitting element according to one embodiment of the present invention. This allows power consumption to be reduced in display areas 5000 to 5005, making it suitable for automotive applications. It is suitable.

[0371] Display area 5000 and display area 5001 are light-emitting elements provided on the windshield of an automobile. This is a display device that uses a light-emitting element. The first electrode and the second electrode are made of a light-transmitting material. By fabricating it with electrodes, the display device becomes transparent, allowing you to see through to the other side, a so-called see-through display device. It can be placed on the windshield of a car. If it is a see-through display, it can be installed on the windshield of a car. Even if installed, it can be placed without obstructing the view. When installing transistors, organic transistors made of organic semiconductor materials or oxide semiconductors may be used. It is preferable to use transistors that are transparent to light, such as transistors that use conductors.

[0372] Display area 5002 is a display device that uses light-emitting elements provided in the pillar portion. 5002 displays images from an imaging device installed on the vehicle body, and the pillars... It can compensate for obstructed vision. Also, similarly, it is provided on the dashboard. The display area 5003 is used to capture the view obstructed by the vehicle body, using an imaging means located on the outside of the vehicle. By displaying these images, blind spots can be compensated for, and safety can be enhanced. By displaying images that complement the surrounding area, safety checks can be performed more naturally and without any sense of incongruity. It is possible.

[0373] Display areas 5004 and 5005 display navigation information, speedometer, engine RPM, and mileage. It can also provide various other information such as fuel level, gear status, and air conditioning settings. The display items and layout can be changed as needed to suit the user's preferences. Furthermore, this information can also be displayed in display areas 5000 to 5003. Display areas 5000 to 5005 can also be used as lighting devices.

[0374] Figures 14(A) and 14(B) show examples of foldable tablet devices. (A) is in the open state, and the tablet terminal consists of a housing 9630, a display unit 9631a, Display unit 9631b, display mode selector switch 9034, power switch 9035, power saving The tablet has a power mode switching switch 9036 and a fastener 9033. The terminal type includes a light-emitting device equipped with a light-emitting element according to one aspect of the present invention, with a display unit 9631a and a display unit 96 It is produced by using one or both of 31b.

[0375] The display unit 9631a can be partially designated as a touch panel area 9632a, and the displayed Data can be entered by touching the operation key 9637. Note that the display unit 9631 In case a, for example, one half of the area has a configuration that only has a display function, and the other half of the area is The diagram shows a configuration with touch panel functionality, but is not limited to this configuration. Display unit 9631 The entire area of ​​a may also be configured to have touch panel functionality. For example, display unit 963 The entire surface of 1a is used as a touch panel with keyboard buttons, and the display unit 9631b is displayed. It can be used as a screen.

[0376] Furthermore, in the display unit 9631b, similar to the display unit 9631a, a part of the display unit 9631b This can be designated as the touch panel area 9632b. Also, the keyboard area of ​​the touch panel... By touching the location where the display toggle button 9639 is displayed with your finger or stylus, the display will change. Keyboard buttons can be displayed on the display unit 9631b.

[0377] Also, touching both the touch panel area 9632a and the touch panel area 9632b simultaneously is also possible. You can also input data.

[0378] Additionally, the display mode switch 9034 changes the display orientation, such as portrait or landscape. You can switch between modes, such as switching between black and white and color displays. Power saving mode switching... The Itch 9036 detects ambient light during use using a light sensor built into the tablet device. The display brightness can be optimized according to the amount of light. The tablet terminal uses optical sensors. In addition to the sensor, other detection devices such as gyroscopes, accelerometers, and other sensors that detect tilt are also used. It can be built-in.

[0379] Furthermore, Figure 14(A) shows an example where the display area of ​​display unit 9631b and display unit 9631a are the same. However, this is not particularly limited, and one size may be different from the other. The quality of these components may also differ. For example, one display panel may be capable of displaying higher resolution than the other. That is also acceptable.

[0380] Figure 14(B) shows the closed state, and in this embodiment, the tablet terminal has a housing. 9630, Solar cell 9633, Charge / discharge control circuit 9634, Battery 9635, DC-DC An example with a converter 9636 is shown. Note that in Figure 14(B), the charge / discharge control circuit 9634 As an example, a configuration having a battery 9635 and a DC-DC converter 9636 is shown. They are doing it.

[0381] Since the tablet device is foldable, the casing 9630 can be closed when not in use. Therefore, the display units 9631a and 9631b can be protected, thus providing durability. We can provide tablet devices that are highly durable and reliable from the perspective of long-term use.

[0382] In addition, the tablet devices shown in Figures 14(A) and 14(B) can also be used for various purposes. Features for displaying information (still images, videos, text images, etc.), calendar, date or time, etc. A function to display information on the display unit, and a touch input function to perform touch input operations or edit the information displayed on the display unit. It has functions such as power control and the ability to control processing by various software (programs). It is possible.

[0383] The solar cell 9633 mounted on the surface of the tablet device powers the touch panel. It can be supplied to the display unit or the video signal processing unit, etc. Note that the solar cell 9633 is If provided on one or two sides of the housing 9630, it allows for efficient charging of the battery 9635. This configuration is preferable because it allows for the implementation of the desired behavior.

[0384] Furthermore, the configuration and operation of the charge / discharge control circuit 9634 shown in Figure 14(B) are shown in Figure 14(C). The block diagram is shown and explained in Figure 14(C). Solar cell 9633, battery 96 35. DC-DC converter 9636, converter 9638, switch SW1 to SW3, The display unit 9631 is shown, along with the battery 9635 and the DC-DC converter 9636. The converter 9638 and switches SW1 to SW3 control the charge / discharge cycle shown in Figure 14(B). This corresponds to the section of road 9634.

[0385] First, let's explain an example of operation when electricity is generated by the solar cell 9633 using ambient light. The electricity generated by the solar panel is converted to a DCD (Digital-to-Collar) voltage to charge the 9635 battery. The C converter 9636 performs either a boost or a buck. Then, the operation of the display unit 9631 is performed. When power charged by the solar cell 9633 is used, turn on switch SW1 and convert The 9638 will boost or lower the voltage to the required level for the display unit 9631. When you do not want to display anything on the display unit 9631, turn SW1 off and turn SW2 on. The configuration should be designed to charge the Terry 9635.

[0386] Note that while the solar cell 9633 is shown as an example of a power generation method, the power generation method is not particularly limited. It is not fixed, and other power generation methods such as piezoelectric elements (piezo elements) and thermoelectric elements (Peltier elements) are used. The configuration may also include charging of the battery 9635 depending on the stage. A contactless power transmission module that sends and receives signals for charging, or a combination of other charging methods. It can be configured in any way, and does not necessarily require a means of generating electricity.

[0387] Furthermore, if the above-mentioned display unit 9631 is provided, an electronic device equipped with a light-emitting element according to one aspect of the present invention The tablet device used as a device is not limited to the tablet device with the shape shown in Figure 14.

[0388] Figures 15(A) to (C) also show a foldable portable information terminal 9310. Figure 15 (A) shows the portable information terminal 9310 in its unfolded state. Figure 15(B) shows the unfolded state or This shows the portable information terminal 9310 in an intermediate state, transitioning from one folded state to the other. Figure 15(C) shows the folded state of the personal digital assistant 9310. Personal digital assistant 9310 It offers excellent portability when folded and a seamless, wide display area when unfolded. This provides excellent readability in the display.

[0389] 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 in the display panel 9311. Display area 931 in the display panel 9311 2 is the display area located on the side of the folded portable information terminal 9310. Area 9312 contains information icons and shortcuts to frequently used apps and programs. It can display information and allow for smoother information checking and app launching. ru.

[0390] Furthermore, an organic compound according to one aspect of the present invention can be used in electronic devices such as organic thin-film solar cells. This is possible. More specifically, because it has carrier transport properties, it can be used in a carrier transport layer and carrier injection. It can be used in layers. Furthermore, by using a mixed film with an acceptor material, charge generation can be achieved. It can be used as a biomass. Furthermore, because it is photoexcited, it can be used as a power generation layer. ru. [Examples]

[0391] (Synthesis Example 1) In this synthesis example, the structural formula (704) shown in Embodiment 1 is 3,10-bis[N-(di [benzofuran-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b'] Detailed information on the synthesis method of bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)) Let me explain. The structural formula for 3,10FrA2Nbf(IV) is shown below.

[0392] [ka]

[0393] <Step 1: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dimethyl Synthesis of synaphthalene Dissolve 11 g (24 mmol) of 3,7-diiodo-2,6-dimethyl in a 500 mL three-necked flask. Xynaphthalene and 14 g (78 mmol) of 4-chloro-2-fluorophenylborone Acid, 22g (0.16mol) potassium carbonate, and 0.74g (2.4 mmol) Lith(2-methylphenyl)phosphine was added. To this mixture, 120 mL of toluene was added. Added [ingredient]. This mixture was degassed by stirring under reduced pressure. 0.11g [ingredient] was added to this mixture. (0.49 mmol) of palladium(II) acetate is added, and the mixture is heated at 110°C for 50°C under a nitrogen atmosphere. It was stirred for 5 hours.

[0394] After stirring, add toluene to this mixture and add Florizil (Wako Pure Chemical Industries, Ltd., catalog). Number: 540-00135), Celite (Wako Pure Chemical Industries, Ltd., Catalog Number: 531) (-16855) The material was filtered by suction through alumina to obtain the filtrate. The filtrate was concentrated to obtain a solid. .

[0395] The obtained solid was subjected to silica gel column chromatography (eluent: toluene:hexane = The solution was purified in a 1:1 ratio. The resulting solid was recrystallized with ethyl acetate, and 5.7 g of the white solid was obtained. It was obtained with a 53% success rate. The synthesis scheme for Step 1 is shown below.

[0396] [ka]

[0397] The obtained solid 1 The 1H NMR data is shown in Figure 76, and the numerical data is shown below. 1 H NMR(CDCl3,300MHz):δ=3.88(s,6H),7.18-7 .24(m,6H),7.37(t,J1=7.2Hz,2H),7.65(s,2H) .

[0398] <Step 2: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dihydro Synthesis of xynaphthalene Dissolve 5.7 g (13 mmol) of 3,7-bis(4-chloro-2-) in a 200 mL three-necked flask. Fluorophenyl)-2,6-dimethoxynaphthalene was added, and the flask was purged with nitrogen. 32 mL of dichloromethane was added to this flask. 28 mL of (28 mmol) was added to this solution. l) Boron tribromide (approximately 1.0 mol / L dichloromethane solution) and 20 mL of dichloromethane The tung solution was added dropwise. After the addition was complete, the solution was stirred at room temperature.

[0399] After stirring, approximately 20 mL of water was added to the solution under ice cooling and stirred. After stirring, the organic layer and aqueous layer were separated. The layers were separated and the aqueous layer was extracted with dichloromethane and ethyl acetate. The extract and the organic layer were then combined. The organic layer was washed with saturated saline solution and saturated sodium bicarbonate solution. The organic layer was then treated with magnesium sulfate. The mixture was dried and then naturally filtered. The resulting filtrate was concentrated, and a white solid was obtained. g was obtained. The synthesis scheme for Step 2 is shown below.

[0400] [ka]

[0401] The obtained solid 1 The 1H NMR data is shown in Figure 77, and the numerical data is shown below. 1 H NMR(DMSO-d6,300MHz):δ=7.20(s,2H),7.37 (dd,J1=8.4Hz,J2=1.8Hz,2H),7.46-7.52(m,4H ), 7.59 (s, 2H), 9.71 (s, 2H).

[0402] <Step 3: 3,10-Dichloronaphtho[2,3-b;6,7-b']bisbenzofura Synthesis of n> Dissolve 5.4 g (13 mmol) of 3,7-bis(4-chloro-2) in a 200 mL three-necked flask. -Fluorophenyl)-2,6-dihydroxynaphthalene and 7.1 g (52 mmol) Potassium carbonate was added. To this mixture, 130 mL of N-methyl-2-pyrrolidone was added. The mixture was degassed by stirring under reduced pressure. After degassing, the mixture was subjected to a nitrogen stream. The mixture was stirred at 120°C for 7 hours. After stirring, water was added to the mixture, and the precipitated solid was filtered off. This solid was washed with water and ethanol. Ethanol was added to the resulting solid, and after heating and stirring... The mixture was filtered to obtain a solid. Ethyl acetate was added to the obtained solid, heated and stirred, then filtered to obtain a pale yellow solid. 4.5 g of the body was obtained with a yield of 92%. The synthesis scheme for Step 3 is shown below.

[0403] [ka]

[0404] The obtained solid 1 The 1H NMR data is shown in Figure 78, and the numerical data is shown below. 1 H NMR(1,1,2,2-Tetrachloroethane-D2,300M Hz):δ=7.44(dd,J1=8.1Hz,J2=1.5Hz,2H),7.65 (d,J1=1.8Hz,2H),8.05(d,J1=8.4Hz,2H),8.14 (s,2H), 8.52(s,2H).

[0405] <Step 4: 3,10-bis[N-(dibenzofuran-2-yl)-N-phenylamine [no]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2N) Synthesis of bf(IV)> Dissolve 1.2 g (3.0 mmol) of 3,10-dichloronaphthate in a 200 mL three-necked flask [2 [3-b;6,7-b']bisbenzofuran and 2.4 g (9.1 mmol) of 2-ani Rinodibenzofuran and 0.11g (0.30 mmol) of di(1-adamantyl)-n -Butylphosphine and 1.8 g (18 mmol) of sodium tert-butoxide [The following ingredients were added]. 30 mL of xylene was added to this mixture. The mixture was stirred under reduced pressure. Degassing was performed by adding 35 mg (61 μmol) of bis(dibenzylidene) to this mixture. Ceton palladium (0) was added, and the mixture was stirred at 150°C for 13 hours under a nitrogen atmosphere.

[0406] After stirring, add toluene to this mixture and add Florizil (Wako Pure Chemical Industries, Ltd., catalog). Number: 540-00135), Celite (Wako Pure Chemical Industries, Ltd., Catalog Number: 531) (-16855) The filtrate was obtained by suction filtration through alumina. The obtained filtrate was concentrated and solidified. We obtained [the desired result]. This solid was purified by silica gel column chromatography (eluent: toluene). A solid was obtained. The obtained solid was recrystallized three times with toluene, yielding 1.8 g of yellow solid, with a yield of 7. I obtained it at 2%.

[0407] The obtained solid (1.1 g) was purified by sublimation using the train sublimation method at a pressure of 3.1p. a. The sample was heated to 390°C under conditions of an argon flow rate of 15 mL / min. After sublimation purification, 0.93 g of yellow solid was obtained with a recovery rate of 87%. The synthesis scheme of Step 4 was The following is shown.

[0408] [ka]

[0409] The obtained solid 1 The 1H NMR data is shown in Figure 16, and the numerical data is shown below. This allows us to... In this synthesis example, 3,10FrA2Nbf(IV), an organic compound according to one embodiment of the present invention, It was found that this was obtained. 1 H NMR(1,1,2,2-Tetrachloroethane-D2,300M Hz):δ=7.08-7.13(m,4H),7.22-7.24(m,6H),7. 31-7.36(m,8H),7.49(t,J1=7.2Hz,2H),7.56-7 .62(m,4H),7.83-7.90(m,6H),7.98(s,2H),8.3 5(s,2H).

[0410] Next, the absorption spectrum and emission spectrum of a toluene solution of 3,10FrA2Nbf(IV) The results of the measurement of the cleats are shown in Figure 17. Also, the thin film of 3,10FrA2Nbf(IV) The absorption and emission spectra are shown in Figure 18. The solid thin film was vacuum deposited onto a quartz substrate. The sample was prepared using the following method. The absorption spectrum of the toluene solution was obtained using a UV-Vis spectrophotometer (Nippon Bunsen Co., Ltd.). The spectral data was measured using a Hikari V550 model, with only toluene placed in a quartz cell. The result is shown after subtracting the ru. Furthermore, a spectrophotometer ((Nippon Co., Ltd.) is used to measure the absorption spectrum of the thin film. A spectrophotometer (U4100) manufactured by Tachi High Technologies was used. In addition, the emission spectrum of the thin film was measured. A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the fluorescence of the solution. For measuring light spectra and emission quantum yield, an absolute PL quantum yield analyzer (Hamamatsu Photonics Corporation) is used. We used a Quantaurus-QY (manufactured by S).

[0411] Figure 17 shows that the toluene solution of 3,10FrA2Nbf(IV) is at 424 nm and 401 nm. Absorption peaks were observed at 300nm, 289nm, and 283nm, and the emission wavelength peak was 44 The wavelengths were 0 nm and 465 nm (excitation wavelength 410 nm). Also, from Figure 18, 3,10Fr Thin films of A2Nbf(IV) are available at 432nm, 407nm, 380nm, 302nm, and 28nm. Absorption peaks were observed at 9 nm and 251 nm, and emission wavelength peaks at 460 nm and 484 nm. It was observed at nm (excitation wavelength 390 nm). From this result, 3,10FrA2Nbf(IV) ) was confirmed to emit blue light, and it was found to be useful as a host for luminescent materials and fluorescent materials in the visible region. It was found to be usable.

[0412] Furthermore, the emission spectrum of 3,10FrA2Nbf(IV) in a toluene solution shows that the long wavelength side The intensity of the second peak around 465nm is small, and the full width at half maximum is 25nm. It was found that the emission was narrow in line width.

[0413] Furthermore, when the luminescence quantum yield in a toluene solution was measured, it was found to be very high at 86%, indicating that the luminescent material... It was found to be suitable as such.

[0414] Due to the narrow linewidth of the emission spectrum and the high emission quantum yield, one aspect of the present invention, 3, 10FrA2Nbf(IV) was found to be an organic compound that can emit light efficiently.

[0415] Next, the 3,10FrA2Nbf(IV) obtained in this example was subjected to liquid chromatography by mass. Analysis(Liquid Chromatography Mass Spectrometer The analysis was performed using y (abbreviated as LC / MS analysis).

[0416] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. Liquid chromatography (LC) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS analysis) was performed using a Q Exactive from IFIC.

[0417] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. Then, dissolve 3,10FrA2Nbf(IV) in an organic solvent to achieve the desired concentration of the sample. The amount was adjusted and the injection volume was set to 5.0 μL.

[0418] Targeted MS 2 According to the law, the ions originate from 3,10FrA2Nbf(IV). MS of component m / z = 822.25 2 Measurements were taken using Targeted-MS. 2 setting The target ion mass range is m / z = 822.25 ± 2.0 (isolatio The detection was performed in positive mode with n window=4. - Energy that accelerates ion-reactive ions: NCE (Normalized Collision Energy) The measurement was performed with n Energy set to 50. The obtained MS spectrum is shown in Figure 19.

[0419] From the results in Figure 19, 3,10FrA2Nbf(IV) is mainly m / z=746, 65 Product ions were detected around 6, 565, 487, 397, and 258. Furthermore, the results shown in Figure 19 are characteristic of 3,10FrA2Nbf(IV) Since this shows the effect, the 3,10FrA2Nbf(IV) contained in the mixture is the same This can be considered important data for making determinations.

[0420] Furthermore, the product ion around m / z=746 is 3,10FrA2Nbf(IV) It is presumed to be a cation in which the phenyl group has been removed, and is 3,10FrA2Nbf(IV) However, this suggests that it contains a phenyl group. Also, around m / z=656 The roduct ion undergoes the removal of the dibenzofuranyl group at 3,10FrA2Nbf(IV). It is presumed to be a cation in the state described above, and 3,10FrA2Nbf(IV) is dibenzofuranyl This suggests that it contains a group. Furthermore, product ions around m / z=565 are 3,10FrA2Nbf(IV) Catio in a state where the N-(dibenzofuran-2-yl)-N-phenylamino group has been removed. It is estimated that 3,10FrA2Nbf(IV) is N-(dibenzofuran-2-yl) This suggests the presence of an N-phenylamino group. [Examples]

[0421] (Synthesis Example 2) In this synthesis example, the structural formula (509) shown in Embodiment 1 is 2,9-bis[N-(9- Phenyl-9H-carbazole-3-yl)-N-phenylamino]naphtho[2,1-b Synthesis method of 6,5-b']bisbenzofuran (abbreviation: 2,9PCA2Nbf(III)) The law will be explained in detail. The structural formula of 2,9PCA2Nbf(III) is shown below.

[0422] [ka]

[0423] <Step 1: 1,5-bis(4-chloro-2-fluorophenyl)-2,7-dihydro Synthesis of xynaphthalene Dissolve 6.2 g (19 mmol) of 1,5-dibromo-2,6-dihyphenate in a 500 mL three-necked flask. Droxynaphthalene and 7.5 g (43 mmol) of 5-chloro-2-fluorophenyl Boronic acid, 25g (78 mmol) of cesium carbonate, and 0.80g (1.9 mmol) 2-dicyclohexylphosphino-2'-6'-dimethoxy-1,1'-biphenyl ( A substance (abbreviated as Sphos) was added. 195 mL of toluene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 0.17 g (0.78 mmol) was added to this mixture. Palladium(II) acetate was added, and the mixture was stirred at 110°C for 7 hours under a nitrogen atmosphere. After stirring, Toluene is added to the mixture, and Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-1) is added. The filtrate was obtained by suction filtration through (6855). The obtained filtrate was concentrated to obtain a solid. The solid was subjected to silica gel column chromatography (neutral silica gel, developing solvent: toluene). It was purified to obtain a solid.

[0424] The obtained solid was recrystallized with toluene to obtain 2.9 g of a white solid in a yield of 35%. The synthesis scheme for 1 is shown below.

[0425] [ka]

[0426] The obtained solid 1 The 1H NMR data is shown in Figure 79, and the numerical data is shown below. 1 H NMR(CDCl3,300MHz):δ=4.78(s,2H),7.15(d ,J1=9.3Hz,2H),7.30-7.38(m,8H).

[0427] <Step 2: 2,9-Dichloronaphtho[2,1-b;6,5-b']bisbenzofuran Synthesis of > Dissolve 2.8 g (6.8 mmol) of 1,5-bis(4-chloro- 2-Fluorophenyl)-2,7-dihydroxynaphthalene and 3.7g (27 mmol) Potassium carbonate was added. To this mixture, 70 mL of N-methyl-2-pyrrolidone was added. The mixture was degassed by stirring under reduced pressure. After degassing, the mixture was subjected to a nitrogen stream. The mixture was stirred at 120°C for 7.5 hours. After stirring, water was added to the mixture, and the precipitated solid was filtered off. This solid was washed with water and ethanol. Ethanol was added to the resulting solid and heated and stirred. After mixing, the solid was collected. Toluene was added to the obtained solid, and after heating and stirring, the precipitated solid was rotated. The mixture was harvested, yielding 2.3 g of a white solid in 91% yield. The synthesis scheme for Step 2 is shown below. .

[0428] [ka]

[0429] The obtained solid 1 The 1H NMR data is shown in Figure 80, and the numerical data is shown below. 1 H NMR(1,1,2,2-Tetrachloroethane-D2,300M Hz):δ=7.56(dd,J1=8.1Hz,J2=1.5Hz,2H),7.81 (d,J1=1.8Hz,2H),8.06(d,J1=8.7Hz,2H),8.40 (d,J1=8.4Hz,2H),8.73(d,J1=8.7Hz,2H).

[0430] <Step 3: 2,9-bis[N-(9-phenyl-9H-carbazol-3-yl)- N-phenylamino]naphtho[2,1-b;6,5-b']bisbenzofuran (abbreviation: 2 Synthesis of ,9PCA2Nbf(III)> Dissolve 1.2 g (3.1 mmol) of 2,9-dichloronaphthate [2, [1-b;6,5-b']bisbenzofuran and 3.1 g (9.2 mmol) of 3-aniline No-9-phenyl-9H-carbazole and 0.11 g (0.31 mmol) of di(1- Adamantyl)-n-butylphosphine and 1.8 g (18 mmol) of sodium t ert-butoxide was added. 30 mL of xylene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 35 mg (62 μmol) of bisphosphonate was added to this mixture. (Dibenzylideneacetone) Add palladium(0) and incubate under a nitrogen stream at 150°C for 11 hours. It was stirred.

[0431] After stirring, add toluene to this mixture and add Florizil (Wako Pure Chemical Industries, Ltd., catalog). Number: 540-00135), Celite (Wako Pure Chemical Industries, Ltd., Catalog Number: 531) (-16855) The filtrate was obtained by suction filtration through alumina. The obtained filtrate was concentrated and solidified. This solid was obtained. This solid was then subjected to silica gel column chromatography (neutral silica gel, developing solvent: The solution was purified with toluene:hexane (1:1) to obtain a solid. The obtained solid was recrystallized with toluene. Then, 2.0 g of yellow solid was obtained with a yield of 66%.

[0432] The obtained solid (1.2 g) was purified by sublimation using the train sublimation method. Pressure: 1.8 × 10 -2 Under conditions of Pa and argon flow rate of 0 mL / min, the sample was heated to 405°C. went. After sublimation purification, 0.96 g of a yellow solid was obtained with a recovery rate of 80%. The synthesis scheme of Step 3 was The following is shown.

[0433] [ka]

[0434] The obtained solid 1 The 1H NMR data is shown in Figure 20, and the numerical data is shown below. This allows us to... In this synthesis example, 2,9PCA2Nbf(III), an organic compound according to one embodiment of the present invention, It was found that this was obtained. 1 H NMR(DMSO-d6,300MHz):δ=7.08(t,J1=7.2Hz ,2H),7.15-7.27(m,8H),7.30-7.47(m,14H),7. 53-7.58(m,2H),7.67-7.73(m,8H),8.05(d,J1= 9.3Hz,2H),8.18(d,J1=2.1Hz,2H),8.21(d,J1= 7.2Hz,2H),8.50(d,J1=8.7Hz,2H),8.71(d,J1= 8.7Hz, 2H).

[0435] Next, the absorption spectrum and emission spectrum of a toluene solution of 2,9PCA2Nbf(III) The results of the measurement of the cleats are shown in Figure 21. Also, the thin film of 2,9PCA2Nbf(III) The absorption and emission spectra are shown in Figure 22. The solid thin film was vacuum deposited onto a quartz substrate. The sample was prepared using the following method. The absorption spectrum of the toluene solution was obtained using a UV-Vis spectrophotometer (Nippon Bunsen Co., Ltd.). The spectral data was measured using a Hikari V550 model, with only toluene placed in a quartz cell. The result is shown after subtracting the ru. Furthermore, a spectrophotometer ((Nippon Co., Ltd.) is used to measure the absorption spectrum of the thin film. A spectrophotometer (U4100) manufactured by Tachi High Technologies was used. In addition, the emission spectrum of the thin film was measured. A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the fluorescence of the solution. For measuring light spectra and emission quantum yield, an absolute PL quantum yield analyzer (Hamamatsu Photonics Corporation) is used. We used a Quantaurus-QY (manufactured by S).

[0436] Figure 21 shows that the toluene solution of 2,9PCA2Nbf(III) is at 424 nm and 405 nm. Absorption peaks were observed around 381nm, 346nm, and 299nm, and the emission wavelength peak was The wavelengths were around 447 nm and 472 nm (excitation wavelength 400 nm). Also, from Figure 22, 2, Thin films of 9PCA2Nbf(III) are available at 431nm, 409nm, 383nm, and 350nm. Absorption peaks were observed around m, 300 nm, and 238 nm, and the emission wavelength peak was 487 It was observed near nm (excitation wavelength 405 nm). From this result, 2,9PCA2Nbf(I II) Confirm that it emits blue light, and use it as a host for luminescent materials and fluorescent materials in the visible region. It was found to be available.

[0437] Furthermore, the emission spectrum of 2,9PCA2Nbf(III) in a toluene solution has a full width at half maximum. It was found that the wavelength is 47nm.

[0438] Furthermore, the emission quantum yield of 2,9PCA2Nbf(III) in a toluene solution was measured. Furthermore, it was found to be very high at 87%, making it suitable as a light-emitting material.

[0439] Next, the 2,9PCA2Nbf(III) obtained in this example was analyzed by LC / MS. It was analyzed.

[0440] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. LC (liquid chromatography) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS) analysis was performed using Q Exactive from IFIC.

[0441] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. The sample is prepared by dissolving 2,9PCA2Nbf(III) of any concentration in an organic solvent. The injection volume was set at 5.0 μL.

[0442] Targeted MS 2 According to the law, the ions are derived from 2,9PCA2Nbf(III). MS of component m / z = 972.35 2 Measurements were taken using Targeted-MS. 2 setting The target ion mass range is m / z = 972.35 ± 2.0 (isolatio The detection was performed in positive mode with n window=4. The energy NCE (Numerical Energy) used to accelerate the acquired ions was set to 50 for measurement. The resulting MS spectrum... The torque is shown in Figure 23.

[0443] From the results in Figure 23, 2,9PCA2Nbf(III) is mainly m / z=333, 25 Product ions were detected near point 5. Note that the results shown in Figure 23 are for 2 Since this shows characteristic results derived from 9PCA2Nbf(III), the mixture This is important data for identifying 2,9PCA2Nbf(III) contained in the material. Yes, I can.

[0444] Furthermore, the product ion around m / z=333 is 2,9PCA2Nbf(III) 2-[N-(9-phenyl-9H-carbazole-3-yl)-N-phenylamino ]Naphtho[2,1-b;6,5-b']Cation with the bisbenzofuranyl group removed It is estimated that 2,9PCA2Nbf(III) is 2-[N-(9-phenyl-9H- Luvazole-3-yl)-N-phenylamino]naphtho[2,1-b;6,5-b']bi This suggests the presence of a benzofuranyl group. [Examples]

[0445] (Synthesis Example 3) In this synthesis example, the structural formula (705) shown in Embodiment 1 is 3,10-bis[N-(9 -phenyl-9H-carbazole-3-yl)-N-phenylamino]naphtho[2,3- Synthesis of [b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)) The method will be explained in detail. The structural formula of 3,10PCA2Nbf(IV) is shown below.

[0446] [ka]

[0447] <Step 1: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dimethyl Synthesis of synaphthalene The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1 in Example 1.

[0448] <Step 2: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dihydro Synthesis of xynaphthalene The synthesis was carried out in the same manner as in step 2 of synthesis example 1 in Example 1.

[0449] <Step 3: 3,10-Dichloronaphtho[2,3-b;6,7-b']bisbenzofura Synthesis of n> The synthesis was carried out in the same manner as in step 3 of synthesis example 1 in Example 1.

[0450] <Step 4: 3,10-bis[N-(9-phenyl-9H-carbazole-3-yl) -N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: Synthesis of 3,10PCA2Nbf(IV)) Dissolve 1.2 g (3.1 mmol) of 3,10-dichloronaphthate in a 200 mL three-necked flask [2 [3-b;6,7-b']bisbenzofuran and 3.1 g (9.2 mmol) of 3-ani Linol-9-phenyl-9H-carbazole and 0.11 g (0.31 mmol) of di(1 -Adamantyl)-n-butylphosphine and 1.8 g (18 mmol) sodium tert-butoxide was added. 30 mL of xylene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 35 mg (62 μmol) of bisphosphonate was added to this mixture. Add dibenzylideneacetone and palladium (0), and incubate under a nitrogen stream at 150°C for 6 hours. It was stirred.

[0451] After stirring, add toluene to this mixture and add Florizil (Wako Pure Chemical Industries, Ltd., catalog). Number: 540-00135), Celite (Wako Pure Chemical Industries, Ltd., Catalog Number: 531) (-16855) The filtrate was obtained by suction filtration through alumina. The obtained filtrate was concentrated and solidified. This solid was obtained. This solid was then subjected to silica gel column chromatography (eluent: toluene:hexa The mixture was purified using a ratio of 1:2 to obtain a solid.

[0452] The obtained solid was recrystallized with toluene to yield 0.92 g of yellow solid in a yield of 31%.

[0453] The obtained solid (0.85 g) was purified by sublimation using the train sublimation method. Pressure: 3.2 ×10 -2 Under conditions of Pa and argon flow rate of 0 mL / min, the sample was heated to 375°C. The procedure was carried out. After sublimation purification, 0.55 g of yellow solid was obtained with a recovery rate of 65%. Synthesis in Step 4 The scheme is shown below.

[0454] [ka]

[0455] The obtained solid 1 The 1H NMR data is shown in Figure 24, and the numerical data is shown below. This allows us to... In this synthesis example, 3,10PCA2Nbf(IV), an organic compound according to one embodiment of the present invention, It was found that this was obtained. 1 H NMR(DMSO-d6,300MHz):δ=7.00-7.11(m,6H) ,7.20-7.25(m,6H),7.30-7.45(m,12H),7.54(t ,J1=6.6Hz,2H),7.61-7.71(m,8H),8.00(d,J1= 8.7Hz,2H),8.08-8.16(m,6H),8.52(s,2H).

[0456] Next, the absorption spectrum and emission spectrum of a toluene solution of 3,10PCA2Nbf(IV) are shown. The results of the measurement of the cleats are shown in Figure 25. Also, the thin film of 3,10PCA2Nbf(IV) The absorption and emission spectra are shown in Figure 26. The solid thin film was vacuum deposited onto a quartz substrate. The sample was prepared using the following method. The absorption spectrum of the toluene solution was obtained using a UV-Vis spectrophotometer (Nippon Bunsen Co., Ltd.). The spectral data was measured using a Hikari V550 model, with only toluene placed in a quartz cell. The result is shown after subtracting the ru. Furthermore, a spectrophotometer ((Nippon Co., Ltd.) is used to measure the absorption spectrum of the thin film. A spectrophotometer (U4100) manufactured by Tachi High Technologies was used. In addition, the emission spectrum of the thin film was measured. A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the fluorescence of the solution. For measuring light spectra and emission quantum yield, an absolute PL quantum yield analyzer (Hamamatsu Photonics Corporation) is used. We used a Quantaurus-QY (manufactured by S).

[0457] Figure 25 shows that the toluene solution of 3,10PCA2Nbf(IV) has wavelengths of 430 nm and 408 nm. Absorption peaks were observed around 383nm, 307nm, 292nm, and 283nm. The peak in light wavelength was around 455 nm (excitation wavelength 410 nm). Also, as shown in Figure 26, 3.10PCA2Nbf(IV) thin films are available at 435nm, 415nm, 385nm, and 29 Absorption peaks are observed around 2 nm and 244 nm, while the emission wavelength peak is around 494 nm. (Excitation wavelength 400 nm) was observed. From this result, 3,10PCA2Nbf(IV) It has been confirmed to emit blue light and can be used as a host for light-emitting materials and fluorescent materials in the visible region. It turned out to be Noh theater.

[0458] Furthermore, the emission spectrum of 3,10PCA2Nbf(IV) in a toluene solution has a full width at half maximum. It was found that the wavelength is 42nm.

[0459] Furthermore, the emission quantum yield of 3,10PCA2Nbf(IV) in a toluene solution was measured. Furthermore, it was found to be very high at 88%, making it suitable as a light-emitting material.

[0460] Next, the 3,10PCA2Nbf(IV) obtained in this example was analyzed by LC / MS. It was analyzed.

[0461] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. LC (liquid chromatography) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS) analysis was performed using Q Exactive from IFIC.

[0462] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. The sample is prepared by dissolving 3,10PCA2Nbf(IV) of any concentration in an organic solvent. The injection volume was set at 5.0 μL.

[0463] Targeted MS2 According to the law, the ions are derived from 3,10PCA2Nbf(IV) MS of component m / z = 972.35 2 Measurements were taken using Targeted-MS. 2 setting The target ion mass range is m / z = 972.35 ± 2.0 (isolatio The detection was performed in positive mode with n window=4. The energy NCE (Nutrient Energy) for accelerating the acquired ions was set to 60 and measured. The obtained MS spectrum... The torque is shown in Figure 27.

[0464] From the results in Figure 27, 3,10PCA2Nbf(IV) is mainly m / z = 894, 72 Product ions were detected around 8, 652, 332, and 255. The results shown in Figure 27 are characteristic results derived from 3,10PCA2Nbf(IV). Therefore, in order to identify 3,10PCA2Nbf(IV) contained in the mixture This can be considered important data.

[0465] Furthermore, the product ion around m / z=894 is 3,10PCA2Nbf(IV) It is presumed to be a cation in which the phenyl group has been removed, and is 3,10PCA2Nbf(IV) However, this suggests that it contains a phenyl group. Also, around m / z=728 The roduct ion is 9-phenylcarbazolyl in 3,10PCA2Nbf(IV). It is presumed to be a cation in a state where the group has been removed, and 3,10PCA2Nbf(IV) is 9-Fe This suggests the presence of a nilccarbazolyl group. Furthermore, the product ion around m / z=332 is 3,10PCA2Nbf(IV) 3-[N-(9-phenyl-9H-carbazole-3-yl)-N-phenylamino ]Naphtho[2,1-b;6,5-b']Cation with the bisbenzofuranyl group removed It is estimated that 3,10PCA2Nbf(IV) is 3-[N-(9-phenyl-9H- Luvazole-3-yl)-N-phenylamino]naphtho[2,1-b;6,5-b']bi This suggests the presence of a benzofuranyl group. [Examples]

[0466] In this embodiment, the light-emitting element 1 and the light-emitting element according to one embodiment of the present invention described in the embodiment The comparative example, comparative light-emitting element 1, will be described in detail. The structural formula of the organic compound used in light-emitting element 1 is shown below.

[0467] [ka]

[0468] (Method for fabricating light-emitting element 1) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm 2 (2mm x 2mm)

[0469] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0470] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0471] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. By the method of adhesion, 9-phenyl-3-[4-(10-phenyl-9] is represented by the above structural formula (i). -Anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA) and molybdenum oxide (VI) and 10nm together so that the weight ratio is 4:2 (=PCzPA: molybdenum oxide) A hole injection layer 111 was formed by vapor deposition.

[0472] Next, a 30 nm layer of PCzPA is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0473] Next, 7-[4-(10-phenyl-9-anthryl), represented by the above structural formula (ii), is shown. )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), The above structural formula (iii) represents 2,9-bis[N-(9-phenyl-9H-carbazol] [Lu-3-yl)-N-phenylamino]naphtho[2,1-b;6,5-b']bisbenzo Fran (abbreviation: 2,9PCA2Nbf(III)) and cgDB in a weight ratio of 1:0.03 A 25nm co-deposited layer was created so that it would be CzPA:2,9PCA2Nbf(III)) to form the emissive layer 1. 13 was formed.

[0474] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above Bathophenanthroline (abbreviated as BPhen), represented by structural formula (iv), is filmed at a thickness of 10 nm. The electron transport layer 114 was formed by depositing the material in a specific manner.

[0475] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed and a light-emitting element 1 was fabricated.

[0476] (Method for fabricating comparative light-emitting element 1) The comparative light-emitting element 1 uses 2,9PCA2Nbf(I) in the light-emitting layer 113 of the light-emitting element 1. II) is represented by the above structural formula (v) 2,9-bis(diphenylamino)naphtho[2,1 -b;6,5-b']bisbenzofuran (abbreviation: 2,9DPhA2Nbf(III)) The light-emitting layer 113 is formed by changing the structure, and cgDBCzPA is deposited to a thickness of 10 nm. After that, BPhen is deposited to a thickness of 15 nm to form an electron transport layer 114. It was fabricated using the following: 2,9DPhA2Nbf(III) used in comparative light-emitting element 1, and light-emitting element The 2,9PCA2Nbf(III) used in child 1 has naphthobisbenzofuran as its main skeleton. These substances have the same structure, but differ in the structure of the amine they bind to.

[0477] The element structures of light-emitting element 1 and comparative light-emitting element 1 are summarized in the table below.

[0478] [Table 1]

[0479] The light-emitting element 1 and the comparative light-emitting element 1 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0480] Figure 28 shows the luminance-current density characteristics of light-emitting element 1 and comparison light-emitting element 1, and the current efficiency-luminance characteristics. Figure 29 shows the luminance-voltage characteristics, Figure 30 shows the current-voltage characteristics, and Figure 31 shows the power efficiency-luminance characteristics. The characteristics are shown in Figure 32, the external quantum efficiency-luminance characteristics in Figure 33, and the emission spectrum in Figure 34. Also, the brightness is 1000 cd / m². 2 Table 2 summarizes the element characteristics in the vicinity.

[0481] [Table 2]

[0482] From Figures 28 to 33 and Table 2, the light-emitting element 1 has a capacitance of 1000 cd / m². 2 External quantum effect in The efficiency was a good 7.4%. Furthermore, light-emitting element 1 was more efficient than comparative light-emitting element 1. It was found to be a good light-emitting element.

[0483] Furthermore, the change in brightness with respect to operating time under the condition of a current value of 2mA and a constant current density. A graph illustrating this is shown in Figure 35. As shown in Figure 35, the light-emitting element 1 after 100 hours of operation It also maintained over 90% of its initial brightness, indicating that it is a light-emitting element with a good lifespan. Furthermore, it was found that light-emitting element 1 had a better lifespan than comparative light-emitting element 1. [Examples]

[0484] In this embodiment, the light-emitting element 2 and the light-emitting element according to one embodiment of the present invention described in the embodiment are shown. Comparative light-emitting element 2, which is a comparative example, will be described in detail. Light-emitting element 2 and comparative The structural formula of the organic compound used in light-emitting element 2 is shown below.

[0485] [ka]

[0486] (Method for fabricating light-emitting element 2) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm 2 (2mm x 2mm)

[0487] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0488] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0489] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. 3-[4-(9-phenanthryl)-phenyl, represented by the above structural formula (vi) by the bonding method. ]-9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum(VI) oxide Co-deposited 10 nm of material so that the weight ratio of material is 4:2 (=PCPPn: molybdenum oxide). A hole injection layer 111 was formed.

[0490] Next, a 30 nm layer of PCPPn is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0491] Next, the 7-[4-(10-phenyl-9-antryl) represented by the above structural formula (ii) Phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and above 2,9-bis[N-(9-phenyl-9H-carbazole], represented by structural formula (iii) [-3-yl)-N-phenylamino]naphtho[2,1-b;6,5-b']bisbenzof Ran (abbreviation: 2,9PCA2Nbf(III)) and a weight ratio of 1:0.03 (=cgDBC) A 25nm co-deposited layer was formed to create the light-emitting layer 11, such that zPA:2,9PCA2Nbf(III)). Formed 3.

[0492] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above Bathophenanthroline (abbreviated as BPhen), represented by structural formula (iv), is filmed at a thickness of 10 nm. The electron transport layer 114 was formed by depositing the material in a specific manner.

[0493] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed, and the light-emitting element 2 of this embodiment was fabricated.

[0494] (Method for fabricating comparative light-emitting element 2) The comparative light-emitting element 2 uses 2,9PCA2Nbf(I) in the light-emitting layer 113 of the light-emitting element 2. II) is represented by the above structural formula (v) 2,9-bis(diphenylamino)naphtho[2,1 -b;6,5-b']bisbenzofuran (abbreviation: 2,9DPhA2Nbf(III)) The light-emitting layer 113 is formed by changing the structure, and cgDBCzPA is deposited to a thickness of 10 nm. After that, BPhen is deposited to a thickness of 15 nm to form an electron transport layer 114. It was fabricated using the following: 2,9DPhA2Nbf(III) used in the comparative light-emitting element 2, and the light-emitting element The 2,9PCA2Nbf(III) used in sub-product 2 has naphthobisbenzofuran as its main skeleton. These substances have the same structure, but differ in the structure of the amine they bind to.

[0495] The element structures of light-emitting element 2 and comparative light-emitting element 2 are summarized in the table below.

[0496] [Table 3]

[0497] The light-emitting element 2 and the comparative light-emitting element 2 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0498] Figure 36 shows the brightness-current density characteristics of light-emitting element 2 and comparison light-emitting element 2, and the current efficiency-brightness characteristics. Figure 37 shows the luminance-voltage characteristics, Figure 38 shows the current-voltage characteristics, and Figure 39 shows the power efficiency-luminance characteristics. The characteristics are shown in Figure 40, the external quantum efficiency-luminance characteristics in Figure 41, and the emission spectrum in Figure 42. Also, the brightness is 1000 cd / m². 2 Table 4 summarizes the element characteristics in the vicinity.

[0499] [Table 4]

[0500] From Figures 36 to 41 and Table 4, the light-emitting element 2 has a wavelength of 1000 cd / m². 2 External quantum effect in It was found that the light-emitting element exhibited good characteristics with a ratio of 10.0%. Furthermore, light-emitting element 2 Furthermore, it was found that this element emits light with better efficiency than comparative light-emitting element 2.

[0501] Furthermore, assuming a current value of 2mA, the change in brightness with respect to the operating time under the condition of constant current density is... The graph showing this is shown in Figure 43. As shown in Figure 43, the light-emitting element 2 continues to function even after 100 hours of operation. It was found to be a light-emitting element with a very good lifespan, maintaining over 90% of its initial brightness. Furthermore, it was found that light-emitting element 2 had a better lifespan than comparative light-emitting element 2. .

[0502] Therefore, one embodiment of the present invention has an amino group containing a carbazolyl group as a substituent. The fluorobisbenzofuran compounds were found to be materials with good lifespan. [Examples]

[0503] In this embodiment, the light-emitting element 3 and the light-emitting element described in the embodiment are light-emitting elements according to one aspect of the present invention. The comparative example, comparative light-emitting element 3, will be described in detail. The structural formula of the organic compound used in the light-emitting element 3 is shown below.

[0504] [ka]

[0505] (Method for fabricating the light-emitting element 3) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm 2 (2mm x 2mm)

[0506] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0507] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0508] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. By the method of adhesion, 9-phenyl-3-[4-(10-phenyl-9] is represented by the above structural formula (i). -Anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA) and molybdenum oxide (VI) and 10nm together so that the weight ratio is 4:2 (=PCzPA: molybdenum oxide) A hole injection layer 111 was formed by vapor deposition.

[0509] Next, a 30 nm layer of PCzPA is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0510] Next, 7-[4-(10-phenyl-9-anthryl), represented by the above structural formula (ii), is shown. )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 3,10-bis[N-(9-phenyl-9H-carbazo], represented by the above structural formula (vii). [Il-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisben Zofran (abbreviation: 3,10PCA2Nbf(IV)) and cgD in a weight ratio of 1:0.03 (=cgD A 25nm co-deposited layer was created to form BCzPA:3,10PCA2Nbf(IV)) to create the emissive layer. Formed 113.

[0511] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above Bathophenanthroline (abbreviated as BPhen), represented by structural formula (iv), is filmed at a thickness of 10 nm. The electron transport layer 114 was formed by depositing the material in a specific manner.

[0512] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed and a light-emitting element 3 was fabricated.

[0513] (Method for fabricating comparative light-emitting element 3) The comparative light-emitting element 3 uses 3,10PCA2Nbf( IV) 3,10-bis(diphenylamino)naphtho, represented by the above structural formula (viii) [2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10DPhA2Nbf(I It was fabricated by forming the light-emitting layer 113 in place of V). ,10DPhA2Nbf(IV) and 3,10PCA2Nbf(IV) used in the light-emitting element 3 ) has the same naphthobisbenzofuran structure as its main skeleton, but the structure of the bonded amine is different. They are substances with different compositions.

[0514] The element structures of light-emitting element 3 and comparative light-emitting element 3 are summarized in the table below.

[0515] [Table 5]

[0516] The light-emitting element 3 and the comparative light-emitting element 3 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0517] Figure 44 shows the brightness-current density characteristics of light-emitting element 3 and comparison light-emitting element 3, and the current efficiency-brightness characteristics. Figure 45 shows the luminance-voltage characteristics, Figure 46 shows the current-voltage characteristics, and Figure 47 shows the power efficiency-luminance characteristics. The characteristics are shown in Figure 48, the external quantum efficiency-luminance characteristics in Figure 49, and the emission spectrum in Figure 50. Also, the brightness is 1000 cd / m². 2 Table 6 summarizes the element characteristics in the vicinity.

[0518] [Table 6]

[0519] From Figures 44 to 49 and Table 6, the light-emitting element 3 has a light intensity of 1000 cd / m². 2 External quantum effect in The efficiency was a good 8.7%. Furthermore, the light-emitting element 3 was more efficient than the comparative light-emitting element 3. It was found to be a good light-emitting element.

[0520] Furthermore, the change in brightness with respect to operating time under the condition of a current value of 2mA and a constant current density. A graph illustrating this is shown in Figure 51. As shown in Figure 51, the light-emitting element 3 after 100 hours of operation It also maintained over 90% of its initial brightness, indicating that it is a light-emitting element with a good lifespan. Furthermore, it was found that light-emitting element 3 had a better lifespan than comparative light-emitting element 3. [Examples]

[0521] In this embodiment, the light-emitting element 4 and the light-emitting element according to one aspect of the present invention described in the embodiment are shown. The comparative example, comparative light-emitting element 4, will be described in detail. The structural formula of the organic compound used in the light-emitting element 4 is shown below.

[0522] [ka]

[0523] (Method for fabricating the light-emitting element 4) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm 2 (2mm x 2mm)

[0524] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0525] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0526] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. 3-[4-(9-phenanthryl)-phenyl, represented by the above structural formula (vi) by the bonding method. ]-9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum(VI) oxide Co-deposited 10 nm of material so that the weight ratio of material is 4:2 (=PCPPn: molybdenum oxide). A hole injection layer 111 was formed.

[0527] Next, a 30 nm layer of PCPPn is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0528] Next, 7-[4-(10-phenyl-9-anthryl), represented by the above structural formula (ii), is shown. )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 3,10-bis[N-(9-phenyl-9H-carbazo], represented by the above structural formula (vii). [Il-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisben Zofran (abbreviation: 3,10PCA2Nbf(IV)) and cgD in a weight ratio of 1:0.03 (=cgD A 25nm co-deposited layer was created to form BCzPA:3,10PCA2Nbf(IV)) to create the emissive layer. Formed 113.

[0529] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above Bathophenanthroline (abbreviated as BPhen), represented by structural formula (iv), is filmed at a thickness of 10 nm. The electron transport layer 114 was formed by depositing the material in a specific manner.

[0530] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed, and the light-emitting element 4 of this embodiment was fabricated.

[0531] (Method for fabricating comparative light-emitting element 4) The comparative light-emitting element 4 uses 3,10PCA2Nbf( IV) 3,10-bis(diphenylamino)naphtho, represented by the above structural formula (viii) [2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10DPhA2Nbf(I It was fabricated by forming the light-emitting layer 113 in place of V). ,10DPhA2Nbf(IV) and 3,10PCA2Nbf(IV) used in the light-emitting element 4 ) has the same naphthobisbenzofuran structure as its main skeleton, but the structure of the bonded amine is different. They are substances with different compositions.

[0532] The element structures of the light-emitting element 4 and the comparative light-emitting element 4 are summarized in the table below.

[0533] [Table 7]

[0534] The light-emitting element 4 and the comparative light-emitting element 4 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0535] Figure 52 shows the luminance-current density characteristics of light-emitting element 4 and comparison light-emitting element 4, and the current efficiency-luminance characteristics. Figure 53 shows the luminance-voltage characteristics, Figure 54 shows the current-voltage characteristics, and Figure 55 shows the power efficiency-luminance characteristics. The characteristics are shown in Figure 56, the external quantum efficiency-luminance characteristics in Figure 57, and the emission spectrum in Figure 58. Also, the brightness is 1000 cd / m². 2 Table 8 summarizes the element characteristics in the vicinity.

[0536] [Table 8]

[0537] From Figures 52 to 57 and Table 8, the light-emitting element 4 has a light intensity of 1000 cd / m². 2 External quantum effect in It was found that the light-emitting element exhibited good characteristics with a ratio of 11.8%. Furthermore, the light-emitting element 4 It was also found that this element emits light with better efficiency than comparative light-emitting element 4.

[0538] Furthermore, the change in brightness with respect to operating time under the condition of a current value of 2mA and a constant current density. A graph illustrating this is shown in Figure 59. As shown in Figure 59, the light-emitting element 4 after 100 hours of operation It maintains over 85% of its initial brightness, indicating that it is a light-emitting element with a very good lifespan. Furthermore, it was found that light-emitting element 4 had a better lifespan than comparative light-emitting element 4. Ta.

[0539] Therefore, one embodiment of the present invention has an amino group containing a carbazolyl group as a substituent. The fluorobisbenzofuran compounds were found to be materials with good lifespan. [Examples]

[0540] In this embodiment, the light-emitting element 5 and the light-emitting element according to one embodiment of the present invention described in the embodiment are shown. The comparative example, comparative light-emitting element 5, will be described in detail. The structural formula of the organic compound used in the light-emitting element 5 is shown below.

[0541] [ka]

[0542] (Method for fabricating the light-emitting element 5) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm2 (2mm x 2mm)

[0543] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0544] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0545] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. By the method of adhesion, 9-phenyl-3-[4-(10-phenyl-9] is represented by the above structural formula (i). -Anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA) and molybdenum oxide (VI) and 10nm together so that the weight ratio is 4:2 (=PCzPA: molybdenum oxide) A hole injection layer 111 was formed by vapor deposition.

[0546] Next, a 30 nm layer of PCzPA is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0547] Next, 7-[4-(10-phenyl-9-anthryl), represented by the above structural formula (ii), is shown. )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), The above structural formula (ix) represents 3,10-bis[N-(dibenzofuran-2-yl)-N -phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3, 10FrA2Nbf(IV)) and a weight ratio of 1:0.03 (=cgDBCzPA:3,10 A light-emitting layer 113 was formed by co-depositing 25 nm of material (FrA2Nbf(IV)) to create a light-emitting layer.

[0548] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above Bathophenanthroline (abbreviated as BPhen), represented by structural formula (iv), is filmed at a thickness of 10 nm. The electron transport layer 114 was formed by depositing the material in a specific manner.

[0549] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed and a light-emitting element 5 was fabricated.

[0550] (Method for fabricating comparative light-emitting element 5) The comparative light-emitting element 5 uses 3,10FrA2Nbf( IV) 3,10-bis(diphenylamino)naphtho, represented by the above structural formula (viii) [2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10DPhA2Nbf(I It was fabricated by forming the light-emitting layer 113 in place of V). ,10DPhA2Nbf(IV) and 3,10FrA2Nbf(IV) used in the light-emitting element 5 ) has the same naphthobisbenzofuran structure as its main skeleton, but the structure of the bonded amine is different. They are substances with different compositions.

[0551] The element structures of the light-emitting element 5 and the comparative light-emitting element 5 are summarized in the table below.

[0552] [Table 9]

[0553] The light-emitting element 5 and the comparative light-emitting element 5 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0554] Figure 60 shows the brightness-current density characteristics of light-emitting element 5 and comparison light-emitting element 5, and the current efficiency-brightness characteristics. Figure 61 shows the luminance-voltage characteristics, Figure 62 shows the current-voltage characteristics, and Figure 63 shows the power efficiency-luminance characteristics. The characteristics are shown in Figure 64, the external quantum efficiency-luminance characteristics in Figure 65, and the emission spectrum in Figure 66. Also, the brightness is 1000 cd / m². 2 Table 10 summarizes the element characteristics in the vicinity.

[0555] [Table 10]

[0556] From Figures 60 to 66 and Table 10, the light-emitting element 5 has a capacitance of 1000 cd / m². 2 External quantum It showed a good result with an efficiency of 6.9%. Furthermore, the light-emitting element 5 was more efficient than the comparative light-emitting element 5. It was found to be a good light-emitting element.

[0557] Furthermore, the change in brightness with respect to operating time under the condition of a current value of 2mA and a constant current density. A graph illustrating this is shown in Figure 67. As shown in Figure 67, the light-emitting element 5 after 100 hours of operation It also maintained over 85% of its initial brightness, indicating that it is a light-emitting element with a good lifespan. Furthermore, it was found that light-emitting element 5 had a better lifespan than comparative light-emitting element 5.

[0558] Therefore, one embodiment of the present invention has an amino group containing a dibenzofuranyl group as a substituent. The naphthobisbenzofuran compound was found to be a material with a good lifespan. [Examples]

[0559] In this embodiment, the light-emitting element 6 and the light-emitting element described in the embodiment of the present invention are shown. The comparative example, comparative light-emitting element 6, will be described in detail. The structural formula of the organic compound used in the light-emitting element 6 is shown below.

[0560] [ka]

[0561] (Method for fabricating the light-emitting element 6) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm 2 (2mm x 2mm)

[0562] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0563] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0564] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. 3-[4-(9-phenanthryl)-phenyl, represented by the above structural formula (vi) by the bonding method. ]-9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum(VI) oxide Co-deposited 10 nm of material so that the weight ratio of material is 4:2 (=PCPPn: molybdenum oxide). A hole injection layer 111 was formed.

[0565] Next, a 30 nm layer of PCPPn is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0566] Next, 7-[4-(10-phenyl-9-anthryl), represented by the above structural formula (ii), is shown. )phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), The above structural formula (ix) represents 3,10-bis[N-(dibenzofuran-2-yl)-N -phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3, 10FrA2Nbf(IV)) and a weight ratio of 1:0.03 (=cgDBCzPA:3,10 A light-emitting layer 113 was formed by co-depositing 25 nm of material (FrA2Nbf(IV)) to create a light-emitting layer.

[0567] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above Bathophenanthroline (abbreviated as BPhen), represented by structural formula (iv), is filmed at a thickness of 10 nm. The electron transport layer 114 was formed by depositing the material in a specific manner.

[0568] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed, and the light-emitting element 6 of this embodiment was fabricated.

[0569] (Method for fabricating comparative light-emitting element 6) The comparative light-emitting element 6 uses 3,10FrA2Nbf( IV) 3,10-bis(diphenylamino)naphtho, represented by the above structural formula (viii) [2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10DPhA2Nbf(I It was fabricated by forming the light-emitting layer 113 in place of V). ,10DPhA2Nbf(IV) and 3,10FrA2Nbf(IV) used in the light-emitting element 6 ) has the same naphthobisbenzofuran structure as its main skeleton, but the structure of the bonded amine is different. They are substances with different compositions.

[0570] The element structures of the light-emitting element 6 and the comparative light-emitting element 6 are summarized in the table below.

[0571] [Table 11]

[0572] The light-emitting element 6 and the comparative light-emitting element 6 are placed in a glove box under a nitrogen atmosphere, and the light-emitting element The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (applying a sealing material around the element). After clothing, UV treatment during sealing, and heat treatment at 80°C for 1 hour, these light-emitting elements undergo initial processing. The characteristics were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0573] Figure 68 shows the brightness-current density characteristics of light-emitting element 6 and comparison light-emitting element 6, and the current efficiency-brightness characteristics. Figure 69 shows the luminance-voltage characteristics, Figure 70 shows the luminance-voltage characteristics, Figure 71 shows the current-voltage characteristics, and Figure 71 shows the power efficiency-luminance characteristics. The characteristics are shown in Figure 72, the external quantum efficiency-luminance characteristics in Figure 73, and the emission spectrum in Figure 74. Also, the brightness is 1000 cd / m². 2 The element characteristics in the vicinity are summarized in Table 12.

[0574] [Table 12]

[0575] From Figures 68 to 74 and Table 12, the light-emitting element 6 has a capacitance of 1000 cd / m². 2 External quantum It was found that the light-emitting element exhibits good characteristics with an efficiency of 9.4%. Furthermore, the light-emitting element 6 It was also found that this element emits light with better efficiency than comparative light-emitting element 6.

[0576] Furthermore, the change in brightness with respect to operating time under the condition of a current value of 2mA and a constant current density. A graph illustrating this is shown in Figure 75. As shown in Figure 75, the light-emitting element 6 after 100 hours of operation It also maintained more than 75% of its initial brightness, indicating that it is a light-emitting element with a good lifespan. Furthermore, it was found that light-emitting element 6 has a better lifespan than the comparative light-emitting element 6.

[0577] Therefore, one embodiment of the present invention has an amino group containing a dibenzofuranyl group as a substituent. The naphthobisbenzofuran compound was found to be a material with a good lifespan. [Examples]

[0578] (Synthesis Example 4) In this synthesis example, the structural formula (510) shown in Embodiment 1 is 2,9-bis[N -(9-phenyl-9H-carbazole-3-yl)-N-phenylamino]naphtho[2 ,1-b;6,5-b']bisbenzofuran (abbreviation: 2,9PCA2Nbf(III)- The synthesis method of 02) will be explained in detail. The construction formula is shown below.

[0579] [ka]

[0580] <Step 1: 1,5-bis(4-chloro-2-fluorophenyl)-2,7-dihydro Synthesis of xynaphthalene The synthesis was carried out in the same manner as in step 1 of synthesis example 2 in Example 2.

[0581] <Step 2: 2,9-Dichloronaphtho[2,1-b;6,5-b']bisbenzofuran Synthesis of > The synthesis was carried out in the same manner as in step 2 of synthesis example 2 in Example 2.

[0582] <Step 3: 2,9-bis[N-(9-phenyl-9H-carbazol-3-yl)- N-phenylamino]naphtho[2,1-b;6,5-b']bisbenzofuran (abbreviation: 2 Synthesis of 9PCA2Nbf(III)-02) Dissolve 0.90 g (2.4 mmol) of 2,9-dichloronaphthate in a 200 mL three-necked flask [2 [1-b;6,5-b']bisbenzofuran and 2.0 g (6.0 mmol) of 2-ani Rhino-9-phenyl-9H-carbazole and 86 mg (0.24 mmol) of di(1- Adamantyl-n-butylphosphine and 1.4 g (14 mmol) of sodium t ert-butoxide was added. 25 mL of xylene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 28 mg (48 μmol) of bisphosphonate was added to this mixture. (Dibenzylideneacetone) Add palladium(0) and incubate under a nitrogen stream at 150°C for 11 hours. The mixture was stirred. After stirring, toluene was added to the mixture, and then Fluorizil, Celite, and alumina were added. The filtrate was obtained by suction filtration. The obtained filtrate was concentrated to obtain a solid. This solid was then processed into silica gel. The solid was obtained by purification using toluene column chromatography (eluent). The body was recrystallized three times with toluene to obtain 0.76 g of a yellow solid in a yield of 33%.

[0583] The obtained solid (0.76 g) was purified by sublimation using the train sublimation method. Pressure: 1.7 ×10 -2 The procedure was performed by heating at 380°C under conditions of Pa and argon flow rate of 0 mL / min. After sublimation purification, 0.63 g of yellow solid was obtained with a recovery rate of 83%. Step 3 Synthesizing ski The following is an example of the term "Mu".

[0584] [ka]

[0585] The obtained solid 1 The 1H NMR data is shown in Figure 81, and the numerical data is shown below. This allows us to... In this synthesis example, 2,9PCA2Nbf(III), an organic compound according to one embodiment of the present invention, It was found that -02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=7.07(tt,J1=7.5Hz ,J2=1.5Hz,2H),7.13(dd,J1=8.1Hz,J2=1.8Hz, 2H),7.19-7.33(m,14H),7.35-7.40(m,8H),7.5 1-7.53(m,8H),7.91(d,J1=8.7Hz,2H),8.07-8. 11(m,4H),8.26(d,J1=8.7Hz,2H),8.60(d,J1=8 .7Hz, 2H).

[0586] Next, the absorption spectrum and emission of a toluene solution of 2,9PCA2Nbf(III)-02 The results of the optical spectrum measurement are shown in Figure 82. Also, 2,9PCA2Nbf(III)- The absorption and emission spectra of the 02 thin film are shown in Figure 83. Sample preparation and measurement The determination method was carried out in the same manner as in Synthesis Example 3.

[0587] From Figure 82, the toluene solution of 2,9PCA2Nbf(III)-02 is 423 nm, 40 Absorption peaks are observed around 3nm, 347nm, 317nm, and 281nm, indicating the emission wavelength. The peaks were around 441 nm and 463 nm (excitation wavelength 410 nm). Also, from Figure 83... The thin film of 2,9PCA2Nbf(III)-02 has wavelengths of 428nm, 408nm, and 347nm. Absorption peaks are observed around m, 265 nm, and 235 nm, and the emission wavelength peak is 460 It was observed at around 481 nm (excitation wavelength 410 nm). From this result, 2,9PCA We confirmed that 2Nbf(III)-02 emits blue light, and we also confirmed the emission of light-emitting materials and fluorescence in the visible region. It was found that it can be used as a host for photomaterials.

[0588] Furthermore, the emission spectrum of 2,9PCA2Nbf(III)-02 in a toluene solution is half It was found that the value width is 43 nm.

[0589] Furthermore, the emission quantum yield of 2,9PCA2Nbf(III)-02 in a toluene solution was measured. The results showed a very high luminescence rate of 89%, indicating its suitability as a light-emitting material.

[0590] Next, the 2,9PCA2Nbf(III)-02 obtained in this example was subjected to LC / MS analysis. This was the analysis. The method of sample preparation, measurement method, and conditions were the same as in Synthesis Example 3 in Example 3. That is the case.

[0591] Targeted MS 2 According to the law, io derived from 2,9PCA2Nbf(III)-02 The MS component of m / z = 972.35 is 2 Measurements were taken using Targeted-MS. 2 The setting is that the mass range of the target ion is m / z = 972.35 ± 2.0 (isola The tion window was set to 4, and detection was performed in positive mode. Collision cell The energy NCE (Natural Energy Efficiency) used to accelerate the target ions within the atmosphere was set to 50 for measurement. The resulting MS The spectrum is shown in Figure 84.

[0592] From the results in Figure 84, 2,9PCA2Nbf(III)-02 is mainly m / z = 896 Product ions were detected near 731, 640, 333, and 256. The results shown in Figure 84 are derived from 2,9PCA2Nbf(III)-02. Since it shows characteristic results, the 2,9PCA2Nbf(II) contained in the mixture This can be considered important data for identifying I)-02.

[0593] The product ion around m / z=896 is 2,9PCA2Nbf(III)-0 It is presumed to be a cation in which the phenyl group in 2 has been removed, and 2,9PCA2Nbf(I II)-02 suggests that it contains a phenyl group. Also, m / z=7 The product ion near 31 is 9-f in 2,9PCA2Nbf(III)-02. It is presumed to be a cation in which the phenylcarbazolyl group has been removed, and is 2,9PCA2Nbf(I II)-02 suggests that it contains a 9-phenyl-9H-carbazolyl group. That is the case. The product ion around m / z=640 is 2,9PCA2Nbf(III)-0 N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino in 2 It is presumed to be a cation in a state where the group has been removed, and 2,9PCA2Nbf(III)-02 is N It contains a -(9-phenyl-9H-carbazole-2-yl)-N-phenylamino group. This suggests that... Furthermore, the product ion around m / z=333 is 2,9PCA2Nbf(III)-0 2-[N-(9-phenyl-9H-carbazol-2-yl)-N-phenyl [amino]naphtho[2,1-b;6,5-b']bisbenzofuranyl group removed It is presumed to be thion, and 2,9PCA2Nbf(III)-02 is 2-[N-(9-pheni Lu-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,1-b;6, This suggests the presence of a 5-b']bisbenzofuranyl group. [Examples]

[0594] (Synthesis Example 5) In this synthesis example, the structural formula (701) shown in Embodiment 1 is 3,10-bis[ N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7 -b'] Method for synthesizing bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02) This will be explained in detail. The structural formula of 3,10FrA2Nbf(IV)-02 is shown below. .

[0595] [ka]

[0596] <Step 1: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dimethyl Synthesis of synaphthalene The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1 in Example 1.

[0597] <Step 2: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dihydro Synthesis of xynaphthalene The synthesis was carried out in the same manner as in step 2 of synthesis example 1 in Example 1.

[0598] <Step 3: 3,10-Dichloronaphtho[2,3-b;6,7-b']bisbenzofura Synthesis of n> The synthesis was carried out in the same manner as in step 3 of synthesis example 1 in Example 1.

[0599] <Step 4: 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamine [no]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2N) bf(IV)-02) synthesis > Dissolve 1.2 g (3.0 mmol) of 3,10-dichloronaphthate in a 200 mL three-necked flask [2 [3-b;6,7-b']bisbenzofuran and 2.0 g (7.7 mmol) of N-(di Benzofuran-3-yl)-N-phenylamine, 0.11 g (0.30 mmol) (1-adamantyl)-n-butylphosphine, 1.8 g (18 mmol) sodium tert-butoxide was added. 30 mL of xylene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 35 mg (61 μmol) of this mixture was added. Add bis(dibenzylideneacetone)palladium(0) and bake at 150°C under a nitrogen atmosphere for 32 Stirred for a while.

[0600] After stirring, toluene and water were added to the mixture, and the mixture was filtered by suction to obtain a solid. Luen was added, and the filtrate was obtained by suction filtration through Florizil, Celite, and alumina. The filtrate was concentrated to obtain a solid. This solid was then subjected to silica gel column chromatography ( The substance was purified with toluene (opening solvent) to obtain a solid. The obtained solid was recrystallized three times in toluene to obtain a yellow 1.8 g of colored solid was obtained with a yield of 71%.

[0601] The obtained solid (1.2 g) was purified by sublimation using the train sublimation method. Pressure: 2.3 × 10 -2 The procedure was performed by heating at 380°C under conditions of Pa and argon flow rate of 0 mL / min. After sublimation purification, 1.0 g of yellow solid was obtained with a recovery rate of 88%. The synthesis scheme of Step 4 was The following is shown.

[0602] [ka]

[0603] The obtained solid 1 The 1H NMR data is shown in Figure 85, and the numerical data is shown below. This allows us to... In this synthesis example, 3,10FrA2Nbf(IV), an organic compound according to one embodiment of the present invention, It was found that -02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=7.12-7.21(m,6H), 7.23-7.26(m,4H),7.28(d,J1=2.1Hz,2H),7.32 -7.40(m,8H),7.44(dd,J1=7.5Hz,J2=1.2Hz,2H ),7.53(d,J1=7.8Hz,2H),7.88(d,J1=8.1Hz,2H ),7.91-7.96(m,4H),8.01(s,2H),8.41(s,2H).

[0604] Next, the absorption spectrum and emission of a toluene solution of 3,10FrA2Nbf(IV)-02 The results of the optical spectrum measurement are shown in Figure 86. Also, 3,10FrA2Nbf(IV)- The absorption and emission spectra of the thin film 02 are shown in Figure 87. The method of sample preparation and The measurement method is the same as in synthesis example 3.

[0605] From Figure 86, the toluene solution of 3,10FrA2Nbf(IV)-02 is 427 nm, 40 Absorption peaks are observed at 4nm, 350nm, and 282nm, while the emission wavelength peak is at 441nm. The excitation wavelength was 468 nm (excitation wavelength 400 nm). Also, from Figure 87, 3,10FrA2N Thin films of bf(IV)-02 are available at 432nm, 412nm, 353nm, and 257nm. Absorption peaks are observed, and emission wavelength peaks are at 462 nm and 488 nm (excitation wavelength 400 nm). This was observed. From this result, it was found that 3,10FrA2Nbf(IV)-02 emits blue light. It is confirmed that it can be used as a host for luminescent materials and fluorescent materials in the visible region. Understood.

[0606] Furthermore, the emission spectrum of 3,10FrA2Nbf(IV)-02 in a toluene solution is long The intensity of the second peak near 468 nm, which is on the wavelength side, is small, and the full width at half maximum is 22 nm. It was found that the emission was extremely narrow in line width.

[0607] Furthermore, when the luminescence quantum yield in a toluene solution was measured, it was found to be very high at 97%, indicating that the luminescent material... It was found to be suitable as such.

[0608] Furthermore, the molar extinction coefficient ε from a toluene solution of 3,10FrA2Nbf(IV)-02 is: It was found to be extremely high at 427nm, at 120,000 [M-1·cm-1]. Therefore, one aspect of the present invention, 3,10FrA2Nbf(IV)-02, is used as a light-emitting material ( When dispersed in a host material as a host material, energy transfer from the host material is efficient. This is suggested to be a common practice. That is, the compound in one aspect of the present invention is a host-guest compound. In obtaining high luminescence efficiency in the light-emitting system, it has properties that make it advantageous as a guest material. ru.

[0609] Due to the narrow linewidth of the emission spectrum and the high emission quantum yield, one aspect of the present invention, 3, 10FrA2Nbf(IV)-02 has been found to be an organic compound capable of efficient luminescence. .

[0610] Next, the 3,10FrA2Nbf(IV)-02 obtained in this example was subjected to LC / MS analysis. This was the analysis. The method of sample preparation, measurement method, and conditions were the same as in Synthesis Example 3 in Example 3. That is the case.

[0611] Targeted MS 2 According to the law, io derived from 3,10FrA2Nbf(IV)-02 The MS component of m / z = 822.25 2 Measurements were taken using Targeted-MS. 2 The setting is that the mass range of the target ion is m / z = 822.25 ± 2.0 (isola The tion window was set to 4, and detection was performed in positive mode. Collision cell The energy NCE (Natural Energy Efficiency) used to accelerate the target ions within the atmosphere was set to 60 for measurement. The resulting MS The spectrum is shown in Figure 88.

[0612] From the results in Figure 88, 3,10FrA2Nbf(IV)-02 is mainly m / z = 744 Product ions were detected near 654, 563, 487, 397, 258, and 230. It was found that this was the case. Furthermore, the results shown in Figure 88 are 3,10FrA2Nbf(IV)- Since this shows characteristic results derived from 02, 3,10F is present in the mixture. This can be considered important data for identifying rA2Nbf(IV)-02.

[0613] The product ion around m / z=744 is 3,10FrA2Nbf(IV)-0 It is presumed to be a cation in which the phenyl group in 2 has been removed, and 3,10FrA2Nbf( IV)-02 suggests that it contains a phenyl group. Also, m / z=6 Product ions around 54 are diben in 3,10FrA2Nbf(IV)-02. It is presumed to be a cation in which the zofuranil group has been removed, and is 3,10FrA2Nbf(IV)- This suggests that 02 contains a dibenzofuranyl group.

[0614] The product ion around m / z=563 is 3,10FrA2Nbf(IV)-0 The state in 2 where the N-(dibenzofuran-3-yl)-N-phenylamino group has been removed. It is presumed to be a cation, and 3,10FrA2Nbf(IV)-02 is N-(dibenzofuran). This suggests the presence of a -3-yl)-N-phenylamino group. The product ion around / z=258 is in 3,10FrA2Nbf(IV)-02. 3-[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b It is presumed to be a cation in which the ;6,7-b']bisbenzofuranyl group has been removed, and 3,10 FrA2Nbf(IV)-02 is 3-[N-(dibenzofuran-3-yl)-N-fe This contains the `nylamino` [naphtho[2,3-b;6,7-b']bisbenzofuranyl group This suggests that... [Examples]

[0615] (Synthesis Example 6) In this synthesis example, the structural formula (707) shown in Embodiment 1 is 3,10-bis[N-( 9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3 -b;6,7-b']Bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02 The synthesis method of ) will be explained in detail. Structural formula of 3,10PCA2Nbf(IV)-02 The following is shown.

[0616] [ka]

[0617] <Step 1: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dimethyl Synthesis of synaphthalene The synthesis was carried out in the same manner as in Step 1 of Synthesis Example 1 in Example 1.

[0618] <Step 2: 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dihydro Synthesis of xynaphthalene The synthesis was carried out in the same manner as in step 2 of synthesis example 1 in Example 1.

[0619] <Step 3: 3,10-Dichloronaphtho[2,3-b;6,7-b']bisbenzofura Synthesis of n> The synthesis was carried out in the same manner as in step 3 of synthesis example 1 in Example 1.

[0620] <Step 4: 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl) -N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: Synthesis of 3,10PCA2Nbf(IV)-02) Dissolve 0.97 g (2.6 mmol) of 3,10-dichloronaphthate in a 200 mL three-necked flask. [2,3-b;6,7-b']bisbenzofuran and 2.6 g (7.7 mmol) of 2-A Nirino-9-phenyl-9H-carbazole, 92 mg (0.26 mmol) di(1- Adamantyl-n-butylphosphine, 1.5g (15 mmol) of sodium te rt-butoxide was added. 26 mL of xylene was added to this mixture. Degassing was performed by stirring under reduced pressure. 30 mg (51 μmol) of bis( Add dibenzylideneacetone (palladium(0)) and stir at 150°C for 7 hours under a nitrogen atmosphere. After stirring, toluene was added to this mixture, and Fluorisyl, Celite, and alumina were passed through it. The mixture was filtered by suction to obtain a filtrate. The obtained filtrate was concentrated to obtain a solid. This solid was then placed in a silica gel container. The solid was purified by Lamb chromatography (eluent: toluene). The solution was recrystallized twice with toluene, yielding 1.6 g of a yellow solid in a yield of 62%.

[0621] The obtained solid (1.1 g) was purified by sublimation using the train sublimation method. Pressure: 1.7 × 10 -2 The procedure was performed by heating at 375°C under conditions of Pa and argon flow rate of 0 mL / min. After sublimation purification, 0.57 g of yellow solid was obtained with a recovery rate of 51%. Synthesis scheme of Step 4 The following is shown.

[0622] [ka]

[0623] The obtained solid 1 The 1H NMR data is shown in Figure 89, and the numerical data is shown below. This allows us to... In this synthesis example, 3,10PCA2Nbf(IV), an organic compound according to one embodiment of the present invention, It was found that -02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=7.05-7.14(m,6H), 7.19-7.24(m,8H),7.26-7.33(m,6H),7.36-7.4 1(m,6H),7.50-7.56(m,8H),7.88(d,J1=8.4Hz, 2H),7.97(s,2H),8.08-8.12(m,4H),8.35(s,2H) ).

[0624] Next, the absorption spectrum and emission of 3,10PCA2Nbf(IV)-02 in a toluene solution. The results of the optical spectrum measurement are shown in Figure 90. Also, 3,10PCA2Nbf(IV)- The absorption and emission spectra of the thin film 02 are shown in Figure 91. The method of sample preparation and The measurement method is the same as in synthesis example 3.

[0625] From Figure 90, the toluene solution of 3,10PCA2Nbf(IV)-02 is 430 nm, 40 Absorption peaks were observed at 8nm, 346nm, and 282nm, while the emission wavelength peak was at 448nm. The excitation wavelength was 476 nm (excitation wavelength 410 nm). Also, from Figure 91, 3,10PCA2N The thin films of bf(IV)-02 are available in 436nm, 415nm, 350nm, 264nm and An absorption peak is observed at 236 nm, and the emission wavelength peak is at 476 nm (excitation wavelength 410 nm). This was observed. From this result, it was found that 3,10PCA2Nbf(IV)-02 emits blue light. It is confirmed that it can be used as a host for luminescent materials and fluorescent materials in the visible region. Understood.

[0626] Furthermore, the emission spectrum of 3,10PCA2Nbf(IV)-02 in toluene solution is long The intensity of the second peak near 476 nm, located on the wavelength side, is low, and the full width at half maximum is 26 nm. It was found that the emission had an extremely narrow linewidth of m.

[0627] Furthermore, when the emission quantum yield in a toluene solution was measured, it was found to be very high at 93%, indicating that the luminescent material... It was found to be suitable as such.

[0628] Furthermore, the molar extinction coefficient ε from the toluene solution of 3,10PCA2Nbf(IV)-02 is: It was found that the value at 430 nm is 110,000 [M-1·cm-1]. Furthermore, 3,10PCA2Nbf(IV)-02, which is one aspect of the present invention, is used as a light-emitting material (guest material When dispersed in a host material as a material, energy transfer from the host material is performed efficiently. It is suggested that the compound in one embodiment of the present invention is a host-guest system It possesses properties that make it advantageous as a guest material for achieving high luminescence efficiency in optical devices.

[0629] Due to the narrow linewidth of the emission spectrum and the high emission quantum yield, one aspect of the present invention, 3, 10PCA2Nbf(IV)-02 has been found to be an organic compound that can emit light efficiently. .

[0630] Next, the 3,10PCA2Nbf(IV)-02 obtained in this example was subjected to LC / MS analysis. This was the analysis. The method of sample preparation, measurement method, and conditions were the same as in Synthesis Example 3 in Example 3. That is the case.

[0631] Targeted MS 2According to the law, io derived from 3,10PCA2Nbf(IV)-02 The MS component of m / z = 972.35 is 2 Measurements were taken using Targeted-MS. 2 The setting is that the mass range of the target ion is m / z = 972.35 ± 2.0 (isola The tion window was set to 4, and detection was performed in positive mode. Collision cell The energy NCE (Natural Energy Efficiency) used to accelerate the target ions within the atmosphere was set to 50 for measurement. The resulting MS The spectrum is shown in Figure 92.

[0632] From the results in Figure 92, 3,10PCA2Nbf(IV)-02 is mainly m / z = 896 Product ions were detected near 869, 731, 640, 333, and 256. This was found. Furthermore, the results shown in Figure 92 are based on 3,10PCA2Nbf(IV)-02. Since it exhibits characteristic results, the 3,10PCA2N contained in the mixture This can be considered important data for identifying bf(IV)-02.

[0633] The product ion around m / z=896 is 3,10PCA2Nbf(IV)-0 It is presumed to be a cation in which the phenyl group in 2 has been removed, and 3,10PCA2Nbf( IV)-02 suggests that it contains a phenyl group. Also, m / z=7 Product ions around 31 are 9-f in 3,10PCA2Nbf(IV)-02. It is presumed to be a cation in which the phenylcarbazolyl group has been removed, and 3,10PCA2Nbf( This suggests that IV)-02 contains a 9-phenylcarbazolyl group. Furthermore, the product ion around m / z=640 is 3,10PCA2Nbf(IV)-0 N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino in 2 It is presumed to be a cation in a state where the group has been removed, and 3,10PCA2Nbf(IV)-02 is N It contains a -(9-phenyl-9H-carbazole-2-yl)-N-phenylamino group. This suggests that... Also, the product ion around m / z=333 is 3,1 3-[N-(9-phenyl-9H-carbazol in 0PCA2Nbf(IV)-02] [Lu-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzo It is presumed to be a cation in which the furanyl group has been removed, and is 3,10PCA2Nbf(IV)-0 2 is 3-[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamine This suggests the presence of the [no]naphtho[2,3-b;6,7-b']bisbenzofuranyl group. It is what it is. [Examples]

[0634] (Synthesis Example 7) In this synthesis example, 3,10-bis[N-(dibenzofuran-4-yl)-N-phenylamine [no]-6,13-diphenylnaphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated) This document provides a detailed explanation of the synthesis method for the compound ph-3,10FrA2Nbf(IV)-II. The structural formula for ph-3,10FrA2Nbf(IV)-II is shown below.

[0635] [ka]

[0636] <Step 1: Synthesis of 2,6-dihydroxy-1,5-diphenylnaphthalene> Dissolve 9.5 g (30 mmol) of 1,5-dibromo-2,6-dihydrox in a 1 L three-necked flask. Synaphthalene, 8.0g (66mmol) of phenylboronic acid, 37g (120mmol) ) Cesium carbonate and 1.2 g (3.0 mmol) of SPhos were added. 300 mL of toluene was added to the substance. This mixture was then degassed by stirring under reduced pressure. To this mixture, 0.27 g (1.2 mmol) of palladium(II) acetate was added, and nitrogen The mixture was stirred at 110°C for 7 hours under an airflow. After stirring, toluene was added to the mixture and passed through Celite. The mixture was then filtered by suction to obtain a filtrate. The obtained filtrate was concentrated to obtain a solid. The obtained solid was then processed using silica gel. Purified by toluene column chromatography (neutral silica gel, developing solvent: toluene), the solution turned yellow. 4.3 g (crude) of the body was obtained. The synthesis scheme for Step 1 is shown below.

[0637] [ka]

[0638] The obtained solid 1 The 1H NMR data is shown in Figure 93, and the numerical data is shown below. This allows us to... In this synthesis example, the organic compound 2,6-dihydroxy-1,5- is an organic compound according to one aspect of the present invention. It was found that diphenylnaphthalene was obtained. 1 H NMR(DMSO-d6,300MHz):δ=7.07(d,J1=9.3Hz ,2H),7.19(d,J1=8.7Hz,2H),7.25-7.41(m,6H) 7.45-7.51 (m, 4H), 9.07 (s, 2H).

[0639] <Step 2: 2,6-bis(2-bromo-4-chlorophenoxy)-1,5-diphen Lunaphthalene synthesis > Add 4.3 g (crude) of 2,6-dihydroxy-1,5- to a 200 mL three-necked flask. Diphenylnaphthalene, 8.6 g (0.42 mol) of 1-bromo-4-chloro-2-ph Luorobenzene and 13 g (41 mmol) of cesium carbonate were added to this mixture. Add 70 mL of N-methyl-2-pyrrolidone and stir the mixture under reduced pressure. The mixture was degassed. After degassing, the mixture was stirred under a nitrogen stream at 120°C for 13.5 hours. After mixing, add 2.9 g (14 mmol) of 1-bromo-4-chloro-2-fluorobenzene. The mixture was then stirred under a nitrogen atmosphere at 120°C for 13.5 hours.

[0640] After stirring, water was added to the mixture, and after irradiation with ultrasound, it was filtered to obtain a solid. The obtained solid was then mixed with water. The solid was then washed with ethanol. This solid was then subjected to silica gel column chromatography (eluent: It was purified with toluene. This solid was recrystallized in a mixed solvent of toluene and ethanol, resulting in a pale yellow substance. 6.3 g of solid was obtained with a yield of 66%. The synthesis scheme for Step 2 is shown below.

[0641] [ka]

[0642] The obtained solid 1 The 1H NMR data is shown in Figure 94, and the numerical data is shown below. This allows us to... In this synthesis example, 2,6-bis(2-bromo-4-) is an organic compound according to one embodiment of the present invention. It was found that chlorophenoxy)-1,5-diphenylnaphthalene was obtained. 1 H NMR(DMSO-d6,300MHz):δ=6.90(d,J1=1.8Hz ,2H),7.06(dd,J1=8.1Hz,J2=2.4Hz,2H),7.28( d,J1=9.3Hz,2H),7.39-7.51(m,10H),7.56-7.6 1 (m, 4H).

[0643] <Step 3: 3,10-dichloro-6,13-diphenylnaphtho[2,3-b;6,7 -b'] Synthesis of bisbenzofuran > Dissolve 6.2 g (9.0 mmol) of 2,6-bis(2-bromo-) in a 200 mL three-necked flask. 4-Chlorophenoxy)-1,5-diphenylnaphthalene and 0.47g (1.8mO I) added triphenylphosphine and 7.1 g (22 mmol) of cesium carbonate. Add 45 mL of N-methyl-2-pyrrolidone to the mixture and stir the mixture under reduced pressure. The mixture was degassed by stirring. After degassing, the mixture was stirred at 120°C for 15 hours under a nitrogen stream. Ta.

[0644] After stirring, water was added to the mixture, and after irradiation with ultrasound, the mixture was filtered to obtain a solid. The solution was dissolved in ene, filtered by suction through Fluorizil, Celite, and alumina, and the filtrate was obtained. The obtained filtrate was concentrated to obtain a solid. The obtained solid was recrystallized with toluene to obtain a yellow solid. It was obtained in 0.2g with a yield of 67%. The synthesis scheme for Step 3 is shown below.

[0645] [ka]

[0646] The obtained solid 1 The 1H NMR data is shown in Figure 95, and the numerical data is shown below. This allows us to... In this synthesis example, the organic compound 3,10-dichloro-6,13- ​​is an organic compound according to one aspect of the present invention. It was found that diphenylnaphtho[2,3-b;6,7-b']bisbenzofuran was obtained. . 1H NMR(1,1,2,2-Tetrachloroethane-D2,300M Hz):δ=7.32(dd,J1=8.4Hz,J2=1.5Hz,2H),7.55 (d,J1=1.5Hz,2H),7.65-7.76(m,10H),7.93(d, J1 = 8.1 Hz, 2 hours), 8.47 (s, 2 hours).

[0647] <Step 4: 3,10-bis[N-(dibenzofuran-4-yl)-N-phenylamine [no]-6,13-diphenylnaphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated) Synthesis of (ph-3,10FrA2Nbf(IV)-II) Dissolve 1.4 g (2.6 mmol) of 3,10-dichloro-6,13 in a 200 mL three-necked flask. -Diphenylnaphtho[2,3-b;6,7-b']bisbenzofuran and 1.7g (6. N-(dibenzofuran-4-yl)-N-phenylamine (4 mmol), 92 mg (0 0.26 mmol) di(1-adamantyl)-n-butylphosphine, 1.5 g (15 ml) (mol) sodium tert-butoxide was added. To this mixture, 25 mL of xylamine was added. Len was added. This mixture was degassed by stirring under reduced pressure. 29m of this mixture was added. Add 51 μmol of bis(dibenzylideneacetone)palladium (0) and nitrogen gas The mixture was allowed to flow and stirred at 150°C for 15 hours.

[0648] After stirring, toluene is added to the mixture and filtered by suction through Fluorisyl, Celite, and alumina. The filtrate was obtained. The obtained filtrate was concentrated to obtain a solid. This solid was subjected to silica gel column chromatography. Matrixography (developing solvent: toluene:hexane = 1:2, then toluene:hexane = It was purified using a 2:3 ratio. The resulting solid was recrystallized in a mixed solvent of toluene and ethyl acetate, and was yellow. 2.0 g of solid was obtained with an 80% yield. 1.1 g of the obtained solid was subjected to train sublimation. The product was purified by sublimation according to the law. Pressure: 2.7 × 10⁻⁶ -2 Conditions: Pa, argon flow rate 0 mL / min The process was then carried out by heating at 380°C. After sublimation purification, 0.94 g of yellow solid was obtained with a recovery rate of 84%. The synthesis scheme for Step 4 is shown below.

[0649] [ka]

[0650] The obtained solid 1 The 1H NMR data is shown in Figure 96, and the numerical data is shown below. This allows us to... In this synthesis example, the organic compound ph-3,10FrA2Nbf( It was found that IV)-II was obtained. 1 H NMR(DMSO-d6,300MHz):δ=6.87(dd,J1=8.7H z,J2=2.4Hz,2H),6.96(d,J1=2.4Hz,2H),7.10- 7.18(m,6H),7.28-7.64(m,24H),7.94(d,J1=8. 1Hz,2H),8.05(d,J1=7.8Hz,J2=1.5Hz,2H),8.1 6(dd,J1=6.9Hz,J2=1.5Hz,2H),8.24(s,2H).

[0651] Next, the ph-3,10FrA2Nbf(IV)-II obtained in this example was analyzed by LC / MS. Analysis was performed by spectroscopy. The sample preparation method, measurement method, and conditions were the same as those in Synthesis Example 3 of Example 3. It is similar to that.

[0652] Targeted MS 2 According to the law, derived from ph-3,10FrA2Nbf(IV)-II MS of the component with m / z = 974.31, which is an ion of 2 Measurements were taken. Targeted -MS 2 The setting is that the mass range of the target ion is m / z = 974.31 ± 2.0 (is The isolation window was set to 4, and detection was performed in positive mode. The energy NCE (Natural Energy Efficiency) used to accelerate the target ion within the ion cell was set to 60 and measured. The MS spectrum is shown in Figure 97.

[0653] From the results in Figure 97, ph-3,10FrA2Nbf(IV)-II is mainly m / z = Product ions were detected near 898, 808, 717, 639, 549, 520, and 458. It was found that it was produced. Furthermore, the results shown in Figure 97 are ph-3,10FrA2Nbf( IV)-II shows characteristic results, therefore, p contained in the mixture This can be considered important data for identifying h-3,10FrA2Nbf(IV)-II. ru.

[0654] Furthermore, the product ion around m / z=898 is ph-3,10FrA2Nbf(IV) It is presumed to be a cation in the state where the phenyl group in )-II has been removed, and ph-3,10Fr This suggests that A2Nbf(IV)-II contains a phenyl group. The product ion around m / z=808 is ph-3,10FrA2Nbf(IV)- It is presumed to be a cation in which the dibenzofuranyl group in II has been removed, and pH-3,10 This suggests that FrA2Nbf(IV)-II contains a dibenzofuranyl group. That is the case.

[0655] Furthermore, the product ion around m / z=717 is ph-3,10FrA2Nbf(IV) The N-(dibenzofuran-4-yl)-N-phenylamino group in )-II was removed. It is presumed to be a cation in a certain state, and ph-3,10FrA2Nbf(IV)-II is N-( This suggests the presence of a benzofuran-4-yl)-N-phenylamino group. Also, the product ion around m / z=458 is ph-3,10FrA2Nbf( IV)-II has two N-(dibenzofuran-4-yl)-N-phenylamino groups It is presumed to be a detached cation, and ph-3,10FrA2Nbf(IV)-II is This suggests the presence of two N-(dibenzofuran-4-yl)-N-phenylamino groups. It is what it is.

[0656] Furthermore, the product ion around m / z=257 is ph-3,10FrA2Nbf(IV) )-II 3-[N-(dibenzofuran-4-yl)-N-phenylamino]-6 ,13-diphenylnaphtho[2,3-b;6,7-b']bisbenzofuranyl group is removed It is presumed to be a cation in a certain state, and ph-3,10FrA2Nbf(IV)-II is 3-[ N-(dibenzofuran-4-yl)-N-phenylamino]-6,13-diphenylnaph This suggests the presence of a [2,3-b;6,7-b']bisbenzofuranyl group. That is the case.

[0657] Next, the absorption spectrum of a toluene solution of pH-3,10FrA2Nbf(IV)-II The results of measuring the emission spectrum are shown in Figure 124. Also, ph-3,10FrA2N The absorption and emission spectra of the bf(IV)-II thin film are shown in Figure 125. The body thin film was fabricated on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was obtained in the ultraviolet range. Measurements were taken using a visible spectrophotometer (JASCO Corporation, Model V550), and toluene alone was found in quartz. The spectrum measured in the cell was subtracted and shown. Furthermore, the absorption spectrum of the thin film was measured. For the measurement, a spectrophotometer (Hitachi High-Technologies Corporation, Spectrophotometer U4100) was used. Furthermore, for measuring the emission spectrum of thin films, a fluorometer (Hamamatsu Photonics Ltd. F) is used. S920 was used. The emission spectrum and emission quantum yield of the solution were measured using the absolute PL quantum yield. A measuring device (Quantaurus-QY, manufactured by Hamamatsu Photonics Ltd.) was used.

[0658] From Figure 124, the toluene solution of pH-3,10FrA2Nbf(IV)-II is 428n Absorption peaks were observed at m, 402nm, 317nm, and 285nm, and the emission wavelength peak was 4 The wavelengths were 41 nm and 469 nm (excitation wavelength 400 nm). Also, from Figure 125, ph-3 The thin film of 10FrA2Nbf(IV)-II has wavelengths of 434nm, 408nm, and 380nm. Absorption peaks were observed at 322nm and 286nm, and emission wavelength peaks were at 459nm and 4 It was observed at 88 nm and 531 nm (excitation wavelength 400 nm). From this result, ph-3,1 We confirmed that 0FrA2Nbf(IV)-II emits blue light, and we investigated the luminescent material and the visible region. It was found that it can be used as a host for fluorescent materials.

[0659] Furthermore, when the luminescence quantum yield in a toluene solution was measured, it was a high 86%, indicating its potential as a luminescent material. It was found to be suitable. [Examples]

[0660] In this embodiment, the light-emitting element 7, which is a light-emitting element according to one embodiment of the present invention described in the embodiment, I will explain in detail below. The structural formula of the organic compound used in the light-emitting element 7 is shown below.

[0661] [ka]

[0662] (Method for fabricating the light-emitting element 7) First, indium tin oxide (ITSO) containing silicon oxide is sputtered onto a glass substrate. A film was deposited using the 3D method to form the anode 101. The film thickness was 70 nm, and the electrode area was 4 mm 2 (2mm x 2mm)

[0663] Next, as a pretreatment for forming light-emitting elements on the substrate, the substrate surface is washed with water, and 200 After firing at ℃ for 1 hour, UV ozone treatment was performed for 370 seconds.

[0664] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0665] Next, the substrate on which the anode 101 is formed is turned so that the surface with the anode 101 is facing downwards. The substrate is fixed to a substrate holder provided inside the vapor deposition apparatus, and vapor deposition is carried out on the anode 101 using resistance heating. 3-[4-(9-phenanthryl)-phenyl, represented by the above structural formula (vi) by the bonding method. ]-9-phenyl-9H-carbazole (abbreviation: PCPPn) and molybdenum(VI) oxide Co-deposited 10 nm of material so that the weight ratio of material is 4:2 (=PCPPn: molybdenum oxide). A hole injection layer 111 was formed.

[0666] Next, a 30 nm layer of PCPPn is deposited on the hole injection layer 111 to form a hole transport layer 112. Ta.

[0667] Next, the 7-[4-(10-phenyl-9-antryl) represented by the above structural formula (ii) Phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and above The structure shown (x) represents 2,9-bis[N-(9-phenyl-9H-carbazole-2 -yl)-N-phenylamino]naphtho[2,1-b;6,5-b']bisbenzofuran (Abbreviation: 2,9PCA2Nbf(III)-02) and a weight ratio of 1:0.03 (=cgDB) CzPA:2,9PCA2Nbf(III)-02) is produced by co-depositing 25nm. A photon layer 113 was formed.

[0668] Subsequently, cgDBCzPA is deposited onto the light-emitting layer 113 to a thickness of 15 nm, and the above 2,9-bis(naphthalene-2-yl)-4,7-diphenyl, represented by structural formula (xii) 1,10-phenanthroline (abbreviated as NBPhen) is vapor-deposited to a film thickness of 10 nm. This formed an electron transport layer 114.

[0669] After forming the electron transport layer 114, lithium fluoride (LiF) is vapor-deposited to a thickness of 1 nm. This forms an electron injection layer 115, and then aluminum is vapor-deposited to a thickness of 200 nm. By attaching the material, a cathode 102 was formed, and the light-emitting element 7 of this embodiment was fabricated.

[0670] The element structure of the light-emitting element 7 is summarized in the table below.

[0671] [Table 13]

[0672] The light-emitting element 7 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element is not exposed to the atmosphere. The process involves sealing with a glass substrate (applying a sealing material around the element and UV treatment during sealing). After heat treatment (at 80°C for 1 hour), the initial characteristics of this light-emitting element were measured. The measurements were taken at room temperature.

[0673] Figure 98 shows the brightness-current density characteristics of the light-emitting element 7, and Figure 99 shows the current efficiency-brightness characteristics. The pressure characteristics are shown in Figure 100, the current-voltage characteristics in Figure 101, ...

Claims

[Claim 1] An organic compound represented by the following general formula (G1). 【Chemistry 1】 (However, in the formula, B is one of the following: a substituted or unsubstituted naphthobisbenzofuran skeleton, a substituted or unsubstituted naphthobisbenzothiophene skeleton, or a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton.) １ A is one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. A is one of a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group, and α １ ~ α ３ Each of these is independently a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms. l, m, and n each independently represent an integer from 0 to 2, and q is 1 or 2.

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