Organic compound, light-emitting element, electronic device, lighting device and electronic apparatus

Abstract

Organic compound, represented by the following formula (G1), where: A represents a group which is represented by the following formula (gl); B represents a skeleton consisting of a substituted or unsubstituted naphthobisbenzofuran skeleton, a substituted or unsubstituted naphthobisbenzothiophene skeleton, and a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton; and q 1 or 2 is; Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms; Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms; each of R 1 to R 8independently of each other, one consisting of hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms; each of α 1 up to α 4 independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 25 carbon atoms, and Each of l, m, n and p independently represents an integer from 0 to 2.

Description

Technical field

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, an electronic device, a lighting device and an electronic device. State of the art

[0002] Several display and light-emitting devices using organic EL elements are in practical use and are finding increasing applications. Significant progress has recently been made in liquid crystal displays; naturally, organic EL displays, referred to as next-generation displays, are expected to exhibit high quality.

[0003] Although various substances have been developed as materials for organic EL displays, there are not enough substances with properties sufficient for practical application. Furthermore, considering the diversity, affinity, and other factors of the combinations, it is undoubtedly true that the greater the selection, the more advantageous it is.

[0004] An organic EL element has a functionally segregated structure in which different substances each perform one or more functions. This places high demands on light-emitting materials, particularly on their emission efficiencies, which determine power consumption, and on their emission colors for improved display quality.

[0005] Patent document 1 discloses an organic compound with a naphthobisbenzofuran skeleton. [Reference][Patent document]

[0006] [Patent Document 1] Japanese Patent Publication No. 2014-237682

[0007] JP 2010-59147 A relates to an organic electroluminescent compound and an organic electroluminescent element that uses it.

[0008] JP 2013-232521 A relates to an organic electroluminescent element and a material for an organic electroluminescent element. The document also relates to a light-emitting device, a display device, and a lighting device.

[0009] WO 2017 / 043757 A1 concerns an organic compound, an organic optoelectronic component and display devices. Summary of the invention Problem to be solved by the invention

[0010] One object of an embodiment of the present invention is to provide a novel organic compound. Another object is to provide an organic compound that emits light with high chromaticity. Another object is to provide an organic compound that emits blue light with high chromaticity. Another object is to provide an organic compound with high emission efficiency. Another object is to provide an organic compound with high charge carrier transport properties. Another object is to provide a reliable organic compound.

[0011] A further object of an embodiment of the present invention is to provide a novel light-emitting element. A further object is to provide a light-emitting element with high emission efficiency. A further object is to provide a light-emitting element that emits light with high chromaticity. A further object is to provide a light-emitting element that emits blue light with high chromaticity. A further object is to provide a light-emitting element with a long lifetime. A further object is to provide a light-emitting element with a low operating voltage.

[0012] An object of a further embodiment of the present invention is to provide a light-emitting device and an electronic device, each of which has low power consumption. An object of a further embodiment of the present invention is to provide a light-emitting device and an electronic device, each of which is very reliable. An object of a further embodiment of the present invention is to provide a light-emitting device and an electronic device, each of which has high display quality.

[0013] The present invention is intended to fulfill at least one of the problems described above. Means to solve the problem

[0014] One embodiment of the present invention is an organic compound represented by the following formula (G1).

[0015] It should be noted that in formula A, there is a group represented by the following formula (g1), and B represents a substituted or unsubstituted naphthobisbenzofuran skeleton, a substituted or unsubstituted naphthobisbenzothiophene skeleton, or a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton. Furthermore, q is either 1 or 2.

[0016] It should be noted that in formula (g1) Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms and Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms. Furthermore, R 1 to R 8Each independently represents hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. Furthermore, α 1 up to α 4 Each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 25 carbon atoms. Furthermore, I, m, n, and p each independently represent an integer from 0 to 2.

[0017] Another embodiment of the present invention is an organic compound with the above structure, wherein Ar 2 an aromatic hydrocarbon group with 6 to 12 carbon atoms.

[0018] Another embodiment of the present invention is an organic compound with the above structure, in which p equals 0.

[0019] Another embodiment of the present invention is an organic compound with the above structure, wherein p is 1 and α 4 a phenylene group.

[0020] Another embodiment of the present invention is an organic compound with the above structure, wherein I, m and n are each independently 0 or 1 and α 1 up to α 3 each is a phenylene group.

[0021] Another embodiment of the present invention is an organic compound with the above structure, in which I is equal to 0.

[0022] Another embodiment of the present invention is an organic compound with the above structure, wherein B is one of the frameworks represented by the following formulas (B1) to (B4).

[0023] It should be noted that in Formula X 2 and X 3Each represents, independently of one another, an oxygen atom or a sulfur atom. It should be noted that in the above formula (B1), one or two of R 10 to R 21 one group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. Furthermore, in the formula (B2) above, one or two of R represent 30 to R 41One group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. Furthermore, in the formula (B3) above, one or two of R represent 50 to R 61One group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. Furthermore, in the formula (B4) above, one or two of R represent 70 to R 81 one group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms.

[0024] Another embodiment of the present invention is an organic compound with the above structure, wherein B is one of the frameworks represented by the above general formulas (B1) to (B3).

[0025] One embodiment of the present invention is an organic compound with the above structure, wherein B is the framework represented by the following formula (B1).

[0026] It should be noted that in Formula X 2 and X 3 Each represents an oxygen atom or a sulfur atom independently of the other. Furthermore, one or two of R represent 10 to R 21one group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms.

[0027] Another embodiment of the present invention is an organic compound with the above structure, in which one or two of R 11 , R 12 , R 17 and R 18 in the above formula (B1) represents a group which is represented by the above formula (g1).

[0028] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 11 or R 12 as well as R 17 or R 18 in the above formula (B1) each are a group represented by the above formula (g1).

[0029] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 11 and R 17 in the above formula (B1) are a group represented by the above formula (g1).

[0030] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 12 and R 18in the above formula (B1) are a group represented by the above formula (g1).

[0031] One embodiment of the present invention is an organic compound with the above structure, wherein B is the framework represented by the following formula (B2).

[0032] It should be noted that in Formula X 2 and X 3 Each represents an oxygen atom or a sulfur atom independently of the other. Furthermore, one or two of R represent 30 to R 41one group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms.

[0033] Another embodiment of the present invention is an organic compound with the above structure, in which one or two of R 31 , R 32 , R 37 and R 38 in the above formula (B2) represents a group which is represented by the above formula (g1).

[0034] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 31 or R 32 and R 37 or R 38 in the above formula (B2) are a group represented by the above formula (g1).

[0035] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 31 and R 37 in the above formula (B2) are a group represented by the above formula (g1).

[0036] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 32 and R 38in the above formula (B2) are a group represented by the above formula (g1).

[0037] One embodiment of the present invention is an organic compound with the above structure, wherein B is the framework represented by the following formula (B3).

[0038] It should be noted that in Formula X 2 and X 3 Each represents an oxygen atom or a sulfur atom independently of the other. Furthermore, one or two of R represent 50 to R 61one group is represented by the formula (G1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms.

[0039] Another embodiment of the present invention is an organic compound with the above structure, in which one or two of R 51 , R 52 , R 57 and R 58 in the above formula (B3) represents a group which is represented by the above formula (g1).

[0040] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 51 or R 52 and R 57 or R 58 in the above formula (B3) are a group represented by the above formula (g1).

[0041] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 51 and R 57 in the above formula (B3) are a group represented by the above formula (g1).

[0042] Another embodiment of the present invention is an organic compound with the above structure, wherein q in the above formula (G1) is 2 and R 52 and R 58in the above formula (B3) are a group represented by the above formula (g1).

[0043] Another embodiment of the present invention is an organic compound with the above structure, wherein X 2 and X 3 each are an oxygen atom.

[0044] Another embodiment of the present invention is an organic compound having the above structure and a molecular weight of 1300 or less.

[0045] Another embodiment of the present invention is an organic compound having the above structure and a molecular weight of 1200 or less.

[0046] Another embodiment of the present invention is a light-emitting element containing the organic compound with the aforementioned structure.

[0047] Another embodiment of the present disclosure is a light-emitting device comprising the light-emitting element with the aforementioned structure and a transistor or a substrate.

[0048] Another embodiment of the present invention is an electronic device comprising the light-emitting element with the aforementioned structure and a sensor, a control button, a loudspeaker or a microphone.

[0049] Another embodiment of the present invention is a lighting device comprising the light-emitting element with the aforementioned structure and a housing.

[0050] Another embodiment of the present disclosure is a light-emitting device comprising the light-emitting element with the aforementioned structure, a substrate and a transistor.

[0051] Another embodiment of the present invention is an electronic device comprising the organic compound with the aforementioned structure.

[0052] It should be noted that the light-emitting device in this description comprises an image display device with a light-emitting element. The light-emitting device may further comprise a module in which a light-emitting element is provided with a connector, such as an anisotropic conductive film or a TCP (tape carrier package), a module in which a printed circuit board is provided at the end of a TCP, or a module in which an IC (integrated circuit) is directly mounted to a light-emitting element by a COG (chip-on-glass) process. A lighting device or the like may also be included in the light-emitting device. Effects of the invention

[0053] According to one embodiment of the present invention, a novel organic compound can be provided. Alternatively, an organic compound that emits light with high chromaticity can be provided. Alternatively, an organic compound that emits blue light with high chromaticity can be provided. Alternatively, an organic compound with high emission efficiency can be provided. Alternatively, an organic compound with high charge carrier transport properties can be provided. Alternatively, a reliable organic compound can be provided.

[0054] According to another embodiment of the present invention, a novel light-emitting element can be provided. Alternatively, a light-emitting element with high emission efficiency can be provided. Alternatively, a light-emitting element that emits light with high chromaticity can be provided. Alternatively, a light-emitting element that emits blue light with high chromaticity can be provided. Alternatively, a light-emitting element with a long lifetime can be provided. Alternatively, a light-emitting element with a low operating voltage can be provided.

[0055] According to another embodiment of the present invention, a light-emitting device and an electronic device can be provided, each of which has low power consumption. According to another embodiment of the present disclosure, a display device can be provided, which has low power consumption. According to another embodiment of the present invention, a light-emitting device and an electronic device can be provided, each of which is very reliable. According to another embodiment of the present disclosure, a display device can be provided, which is very reliable. According to another embodiment of the present invention, a light-emitting device and an electronic device can be provided, each of which has high display quality.According to another embodiment of the present disclosure, a display device can be provided which has a high display quality.

[0056] It should be noted that the description of these effects does not preclude the existence of further effects. It should be noted that an embodiment of the present invention need not necessarily exhibit all of these effects. It should be noted that further effects may become apparent from the explanation of the description, the drawings, the claims, and the like, and further effects may be derived from the explanation of the description, the drawings, the claims, and the like. Brief description of the drawings [ Fig. 1] Schematic representations of light-emitting elements. [ Fig. 2] Illustrations that represent an example of a manufacturing process for a light-emitting element. [ Fig. 3] A representation that shows an example of a droplet ejection device. [ Fig. 4] Conceptual representations of a light-emitting active matrix device. [ Fig. 5] Conceptual representations of a light-emitting active matrix device. [ Fig. 6] A conceptual representation of a light-emitting active matrix device. [ Fig. 7] Conceptual representations of a light-emitting passive matrix device. [ Fig. 8] Illustrations depicting a lighting device. [ Fig. 9] Illustrations depicting electronic devices. [ Fig. 10] A representation depicting a light source device. [ Fig. 11] A representation depicting a lighting device. [ Fig. 12] A representation depicting a lighting device. [ Fig. 13] A representation depicting display devices and lighting devices in the vehicle. [ Fig. 14] Illustrations depicting an electronic device. [ Fig. 15] Illustrations depicting an electronic device. [ Fig. 16] 1 H-NMR spectra of 3,7-Bis(4-chloro-2-fluorophenyl)-2,6-dimethoxynaphthalene. [ Fig. 17] 1 H-NMR spectra of 3,7-Bis(4-chloro-2-fluorophenyl)-2,6-dihydroxynaphthalene. [ Fig. 18] 1 H-NMR spectra of 3,10-Dichloronaphtho[2,3-b;6,7-b']bisbenzofuran. [ Fig. 19] 1H-NMR spectra of N,N'-Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mMemFLPA2Nbf(IV)). [ Fig. 20] An absorption spectrum and an emission spectrum of 3.10mMemFLPA2Nbf(IV) in a toluene solution. [ Fig. 21] An absorption spectrum and an emission spectrum of 3.10mMemFLPA2Nbf(IV) in a thin-film state. [ Fig. 22] An MS spectrum of 3.10mMemFLPA2Nbf(IV). [ Fig. 23] Luminance-current density properties of a light-emitting element 1 and a light-emitting comparison element 1. [ Fig. 24] Power efficiency-luminance properties of light-emitting element 1 and light-emitting comparison element 1. [ Fig. 25] Luminance-voltage properties of light-emitting element 1 and light-emitting reference element 1. [ Fig. 26] Current-voltage properties of light-emitting element 1 and light-emitting comparison element 1. [ Fig. 27] External quantum efficiency luminance properties of light-emitting element 1 and light-emitting reference element 1. [ Fig. 28] Emission spectra of light-emitting element 1 and light-emitting reference element 1. [ Fig. 29] Luminance-current density properties of a light-emitting element 2. [ Fig. 30] Power efficiency-luminance properties of the light-emitting element 2. [ Fig. 31] Luminance-voltage properties of the light-emitting element 2. [ Fig. 32] Current-voltage properties of the light-emitting element 2. [ Fig. 33] The xy chromaticity of the light-emitting element 2. [ Fig. 34] External quantum efficiency luminance properties of the light-emitting element 2. [ Fig. 35] A diagram showing an emission spectrum of the light-emitting element 2. [ Fig. 36] 1 H-NMR spectra of 3.10mFLPA2Nbf(IV). [ Fig. 37] An absorption spectrum and an emission spectrum of 3.10mFLPA2Nbf(IV) in a toluene solution. [ Fig. 38] An absorption spectrum and an emission spectrum of 3.10mFLPA2Nbf(IV) in a thin-film state. [ Fig. 39] An MS spectrum of 3.10mFLPA2Nbf(IV). [ Fig. 40] Luminance-current density properties of a light-emitting element 3. [ Fig. 41] Power efficiency-luminance properties of the light-emitting element 3. [ Fig. 42] Luminance-voltage properties of the light-emitting element 3. [ Fig. 43] Current-voltage properties of the light-emitting element 3. [ Fig. 44] External quantum efficiency luminance properties of the light-emitting element 3. [ Fig. 45] An emission spectrum of the light-emitting element 3. [ Fig. 46] Normalized luminance-time-vary properties of the light-emitting element 3. [ Fig. 47] Normalized luminance-time-vary properties of the light-emitting element 1. Types of embodiments of the invention

[0057] Embodiments of the present invention are described in detail below with reference to the drawings. It should be noted that the present invention is not limited to the following description, and it is readily apparent to a person skilled in the art that the types and details can be modified in various ways without departing from the concept and scope of the present invention. Therefore, the present invention should not be considered as limited to the description of the embodiments shown below. (Version 1)

[0058] An organic compound of an embodiment of the present invention is an organic compound represented by the following formula (G1).

[0059] In the above formula (G1), B represents a substituted or unsubstituted naphthobisbenzofuran skeleton, a substituted or unsubstituted naphthobisbenzothiophene skeleton, or a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton.

[0060] Furthermore, A is a group represented by the following formula (g1), and one or two of A is / are bound to the preceding framework B (i.e., q is 1 or 2).

[0061] In the above formula (g1), Ar represents 1 a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms and Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms. Furthermore, R 1 to R 8Each independently represents hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms.

[0062] In the above formula (g1) α 1 , α 2 , α 3 and α 4 Each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 25 carbon atoms, and I, m, n and p each independently represent a numerical value of 0, 1 or 2.

[0063] An organic compound with a substituted or unsubstituted naphthobisbenzofuran or naphthobisbenzothiophene framework is a framework that is very useful as a luminophore for a light-emitting element. This organic compound exhibits high emission efficiency and emits a high proportion of blue light; therefore, the light-emitting element in which this organic compound is used can be a blue light-emitting element with high emission efficiency. Various substances have been developed as blue fluorescent materials. The present organic compound, whose chromaticity exhibits very high blue light emission, is a promising material as a blue light-emitting material for representing a color space that covers the ITU-R-BT.2020 standard, i.e., an international standard for an ultrawide color space for an 8K display.

[0064] The present inventors have discovered that, in particular, a light-emitting element in which an organic compound with a specific arylamine, as represented in the above formula (g1) or the like, is used for these frameworks, can be a light-emitting element with further improved properties. In particular, effects such as a further improvement in emission efficiency and a further improvement in color purity are obtained. This is because the 9-position of the fluorene is bonded to the amine (N) side, and therefore the conjugation does not readily extend, and light with a short wavelength is readily emitted.

[0065] It should be noted that in the above formula (g1) there is a structure in which α 1 , α 2 , α 3 and α 4Since each is independently 0, this is preferred because the number of synthesis steps is smaller and the sublimation temperature is lower.

[0066] Furthermore, Ar 1 and Ar 2 preferably an aromatic hydrocarbon group, as it is valued for its high stability following excitation, and a substituted or unsubstituted phenyl group is more strongly preferred.

[0067] Furthermore, Ar 2 preferably a substituted or unsubstituted aromatic hydrocarbon group, as the synthesis can be carried out more easily.

[0068] Ar 2 is preferably a hydrocarbon group, as it is easier to dissolve in an organic solvent, cleaning is simpler and film formation is easier by a wet process.

[0069] Furthermore, q is preferably 2, as this increases the quantum yield; q is preferably 1, as the sublimation temperature is lower in this case. It should be noted that in the case where q is 2, two groups bonded to B and represented by the above formula (g1) may have different structures.

[0070] Preferably, the above formula (g1) comprises a substituent, and the substituent is a hydrocarbon group, which leads to the following effects: the molecule is steric, the sublimation temperature is lower, an excimer is not readily formed, and the like. Furthermore, such a compound is preferred because it dissolves more readily in an organic solvent and is easier to purify.

[0071] It should be noted that in this description, the sublimation temperature also refers to the evaporation temperature.

[0072] Furthermore, Ar 1 In the preceding formula (g1), a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms is represented. In particular, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dimethylfluorenyl group, a spirofluorenyl group, a diphenylfluorenyl group, a phenanthryl group, anthryl group, a dihydroanthryl group, a triphenylenyl group, a pyrenyl group, and the like can be specified as a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms. 1are shown in the following structural formulas (Ar-100) to (Ar-119) and (Ar-130) to (Ar-140). It should be noted that these may further include a substituent, such as a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a trimethylsilyl group.

[0073] It should be noted that, as in (Ar-100) to (Ar-108), a group to which a phenyl group is bonded is preferred because the conjugation does not expand easily and the emission wavelength is a short wavelength.

[0074] Furthermore, as in (Ar-100) to (Ar-119), a group of hydrocarbons in which the number of six-membered fused rings is two or less, such as a benzene ring, a naphthalene ring or a fluorene ring, or in which the number of six-membered fused rings is three or more, wherein a six-membered ring is fused with another six-membered ring only at position a, position c or position e, such as a phenanthrene ring, is preferred because the conjugation does not expand easily and light with a short wavelength is emitted.

[0075] Furthermore, Ar 2 In the above formula (g1), an aromatic hydrocarbon group with 6 to 25 carbon atoms is represented. The same aromatic hydrocarbon groups with 6 to 25 carbon atoms as Ar can be used. 1 be specified.

[0076] In the above formula (g1) α 1 up to α 4Each group, independently of one another, represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 25 carbon atoms; in particular, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenediyl group, a dimethylfluorenediyl group, and the like are specified. It should be noted that in the case where I, m, n, and p are each two, the two bonded α groups may have different structures.

[0077] Typical examples of α 1 up to α 4Groups represented by the following structural formulas (Ar-1) to (Ar-33) can be specified. It should be noted that these may further include a substituent, such as a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms.

[0078] It should be noted that as in (Ar-1) to (Ar-11) α 1 up to α 4Preferably, each group consists of a phenylene group or a group in which several phenylene groups are linked together, since the conjugation does not expand easily and the singlet excitation level is kept high. In particular, a structure with a meta-phenylene group exhibits excellent effects and is therefore preferred. This structure is also preferred because the molecule is steric and the sublimation temperature is lower. Furthermore, a structure in which α 1 up to α 4The presence of para-phenylene groups increases the reliability as a light-emitting material. Furthermore, the case in which substituents are linked via carbon with a sigma bond, such as at the 9 position of fluorene, as in (Ar-24) to (Ar-27), is preferred because the conjugation does not expand easily and the S1 level is kept high, resulting in a shorter emission wavelength.

[0079] In the organic compound represented by the above formula (G1), the substituted or unsubstituted naphthobisbenzofuran skeleton or the substituted or unsubstituted naphthobisbenzothiophene skeleton represented by B is preferably one of the skeletons represented by the following formulas (B1) to (B4).

[0080] In the case where I, m, n and p are each 2, then at α 1 , α 2 , α 3and α 4 Different substituents can be linked together. For example, in (Ar-17) and (Ar-18) naphthylene and phenylene are linked together.

[0081] In the formulas (B1) to (B4) above, X represents 2 and X 3 Each represents, independently of one another, an oxygen atom or a sulfur atom. It should be noted that, for the sake of simplicity of synthesis, the two atoms are preferably the same. Furthermore, the two are preferably oxygen atoms, since effects such as simple synthesis, a high singlet excitation level, light emission with a shorter wavelength, and a high emission yield can be obtained. It should be noted that at X 2 and X 3The number of oxygen atoms or sulfur atoms can be appropriately selected depending on the desired singlet excitation level or emission wavelength; if the number of oxygen atoms is greater, light with a shorter wavelength is emitted, while light with a longer wavelength is emitted if the number of sulfur atoms is greater.

[0082] The wavelength of the framework, represented as B in formula (G1), tends to become longer in the following order: the preceding formula (B2), the preceding formula (B4), the preceding formula (B1), and the preceding formula (B3); accordingly, any one of them can be selected according to the desired emission color. To obtain a blue light emission with a shorter wavelength, the compound represented by formula (B2) is preferred. To obtain a blue light emission with a relatively long wavelength, the compound represented by formula (B3) is preferred.

[0083] In an organic compound represented by the above formula (G1), wherein the above formula (B1) is B, one or two of R further constitute 10 to R 21One group is represented by the preceding formula (g1), and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. It should be noted that the group represented by the preceding formula (g1) preferably comprises one or two of R 11 , R 12 , R 17 and R 18 from R 10 to R 21 This is because the synthesis is simple.

[0084] In an organic compound represented by the above formula (G1), where the above formula (B1) is B, in the case where two of R are 10 to R 21is a group represented by the above formula (g1) (i.e., in the case where q in the above formula (G1) is 2), for the simple synthesis it is preferable that R is 11 or R 12 as well as R 17 or R 18 is a group represented by the formula (g1) above. In this case, R is also 11 and R 17 preferably a group represented by the preceding formula (g1) to obtain light emission with a long wavelength. Preferably R 12 and R 18 to a group represented by the above formula (g1) since a light emission with a short wavelength is obtained, the emission quantum efficiency is high and also high reliability in the light emission is achieved.

[0085] In an organic compound represented by the above formula (G1), wherein the above formula (B2) is B, one or two of R further constitute 30 to R 41 One group is represented by the preceding formula (g1), and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. It should be noted that the group represented by the preceding formula (g1) preferably comprises one or two of R 31 , R 32 , R 37 and R 38 from R 30 to R 41 This is because the synthesis is simple.

[0086] In an organic compound represented by the above formula (G1), where the above formula (B2) is B, in the case where two of R are 30 to R 41 is a group represented by the above formula (g1) (i.e., in the case where q in the above formula (G1) is 2), for the simple synthesis it is preferable that R is 31 or R 32 as well as R 37 or R 38 is a group represented by the formula (g1) above. In this case, R is also 31 and R 37 preferably a group represented by the preceding formula (g1) to obtain light emission with a long wavelength. Preferably R 32 and R 38to a group represented by the above formula (g1) since a light emission with a short wavelength is obtained, the emission quantum efficiency is high and also high reliability in the light emission is achieved.

[0087] In an organic compound represented by the above formula (G1), wherein the above formula (B3) is B, one or two of R further constitute 50 to R 61One group is represented by the formula (g1) above, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. It should be noted that one or two of R 51 , R 52 , R 57 and R 58 from R 50 to R 61 preferably a single binding.

[0088] In an organic compound represented by the above formula (G1), where the above formula (B3) is B, in the case where two of R are 50 to R 61is a group represented by the above formula (g1) (i.e., in the case where q in the above formula (G1) is 2), for the simple synthesis it is preferable that R is 51 or R 52 as well as R 57 or R 58 is a group represented by the formula (g1) above. In this case, R is also 51 and R 57 preferably a group represented by the preceding formula (g1) to obtain light emission with a long wavelength. Preferably R 52 and R 58 to a group represented by the above formula (g1) since a light emission with a short wavelength is obtained, the emission quantum efficiency is high and also high reliability in the light emission is achieved.

[0089] In an organic compound represented by the above formula (G1), wherein the above formula (B4) is B, one or two of R further constitute 70 to R 81 One group is represented by the preceding formula (g1), and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. It should be noted that the group represented by the preceding formula (g1) preferably comprises one or two of R 71 , R 72 , R 77 and R 78 from R 70 to R 81 it.

[0090] In an organic compound represented by the above formula (G1), where the above formula (B4) is B, in the case where two of R are 70 to R 81 is a group represented by the above formula (g1) (i.e., in the case where q in the above formula (G1) is 2), for the simple synthesis it is preferable that R is 71 or R 72 as well as R 77 or R 78 is a group represented by the formula (g1) above. In this case, R is also 71 and R 78 preferably a group represented by the preceding formula (g1) to obtain light emission with a long wavelength. Preferably R 72 and R 77to a group represented by the above formula (g1) since a light emission with a short wavelength is obtained, the emission quantum efficiency is high and also high reliability in the light emission is achieved.

[0091] Furthermore, in the above formulas (B1) to (B4), the substituents are those represented by R. 10 to R 21 , R 30 to R 41 , R 50 to R 61 and R 70 to R 81 Apart from those represented by the preceding formula (g1), they may preferably be prepared using hydrogen, since the synthesis is simpler and the sublimation temperature is lower. On the other hand, if substituents other than hydrogen are used, the heat resistance, solubility in a solvent, and the like can be improved.

[0092] It should be noted that, with regard to sublimation capability, the molecular weight of the organic compound represented by the preceding formula (G1) is preferably 1300 or less, more preferably 1000 or less. With regard to film quality, a molecular weight of 650 or more is preferred.

[0093] In the case where a framework or group bonded to the organic compound described above comprises a substituent, the substituent is preferably a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, an aromatic hydrocarbon group with 6 to 14 carbon atoms, or a trimethylsilyl group.

[0094] As a hydrocarbon group with 1 to 10 carbon atoms, which act as substituents, through R 1 to R 81The following can be selected as the cyclic hydrocarbon group, which is represented as a carbon atom or as a substituent bonded to another substituent: a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an icosyl group, and the like. Furthermore, a cyclopropyl group, a cyclohexyl group, and the like can be selected as cyclic hydrocarbon groups with 3 to 10 carbon atoms. Additionally, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a fluorenyl group, and the like can be selected as aromatic hydrocarbon groups with 6 to 14 carbon atoms.Furthermore, with respect to the diarylamino group with 12 to 32 carbon atoms, its respective aryl groups are preferably, independently of one another, an aromatic hydrocarbon group with 6 to 16 carbon atoms. The aromatic hydrocarbon group can be a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a fluorenyl group, a naphthylphenyl group, and the like. It should be noted that the substituents defined by R. 1 to R 81 They can be represented as substituents, furthermore having an aliphatic hydrocarbon group with 1 to 6 carbon atoms, an alicyclic hydrocarbon group with 3 to 6 carbon atoms or the like.

[0095] Examples of the organic compounds of the present invention, which have the aforementioned structures, are shown below.

[0096] In formula (g1) of embodiment 1, in the case where one of I, m, n and p 2 is, α can be 1 , α 2 , α 3 and α 4 Different divalent aromatic hydrocarbon groups are linked together. For example, in compound (305) n 2, paraphenylenes and metaphenylenes are represented as α 3 interconnected.

[0097] An example of a method for synthesizing the organic compounds of the present invention described above is then described by using as an example an organic compound represented by formula (G1-1), which is an organic compound of an embodiment of the present invention. The organic compound represented by formula (G1-1) is shown below.

[0098] It should be noted that in formula B, a substituted or unsubstituted naphthobisbenzofuran skeleton, a substituted or unsubstituted naphthobisbenzothiophene skeleton, or a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton is represented. Furthermore, Ar represents 1 a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms and Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms. Furthermore, R 1 to R 8 Each independently represents hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. Furthermore, α 1 up to α 4Each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 25 carbon atoms. Furthermore, I, m, n, and p each independently represent an integer from 0 to 2, and q is either 1 or 2.

[0099] As shown in the following synthesis scheme, the organic compound represented by formula (G1-1) can be obtained by a cross-coupling reaction of compound (a1) with an arylamine compound (a2). Examples of X 1 A halogen group, such as chlorine, bromine, or iodine, and a sulfonyl group can be specified. In the case where I equals 0 (i.e., compound (a2) is a secondary amine), D represents 1 hydrogen; in the case of 1 or more (i.e. compound (a2) is a tertiary amine) it represents a boronic acid, a dialkoxyboronic acid, arylaluminum, arylzirconium, arylzinc, aryltin or the like.

[0100] This reaction can proceed under various conditions. For example, a synthesis procedure using a metal catalyst in the presence of a base can be employed. For instance, if I is 0, the Ullmann coupling or the Hartwig-Buchwald reaction can be used. If I is 1 or more, the Suzuki-Miyaura reaction can be used.

[0101] It should be noted that here q-equivalents of compound (a2) are reacted with compound (a1), in the case where q is 2 or more, i.e. the number of substituents shown in the brackets of q with respect to B in compound (G1) is 2 or more, and these substituents are not equal, any type of compound (a2) can be reacted with compound (a1).

[0102] The organic compound of an embodiment of the present invention can be synthesized in the manner described above.

[0103] It should be noted that the aforementioned compound (a1) can be compounds represented by the following formulas (B1-a1) to (B4-a1). These are effective compounds for the synthesis of compounds of an embodiment of the present invention. Likewise, their starting materials are effective for this purpose. Regarding the synthesis method, by appropriately modifying the substitution site of a halogen, the synthesis can be carried out in a manner similar to the examples described below.

[0104] In the preceding formulas (B1-a1) to (B4-a1), X represents 2 and X 3 Each represents either an oxygen atom or a sulfur atom, independently of the other.

[0105] Furthermore, in the above formula (B1-a1) one or two of R represent 10 to R 21One halogen is represented, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. It should be noted that one halogen is preferably one or two of R 11 , R 12 , R 17 and R 18 from R 10 to R 21 This is because the synthesis is simple.

[0106] Furthermore, in the case where there are two of R 10 to R 21 Since in the above formula (B1-a1) each is a halogen, for the simple synthesis it is preferable that R is 11 or R 12 as well as R 17 or R 18 Each is a halogen. In this case, R is also 11 and R 17each preferably by a halogen and at R 12 and R 18 each preferably involving a halogen.

[0107] Furthermore, in the above formula (B2-a1), one or two of R represent 30 to R 41 One halogen is represented, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. It should be noted that one halogen is preferably one or two of R 31 , R 32 , R 37 and R 38 from R 30 to R 41 This is because the synthesis is simple.

[0108] Furthermore, in the case where there are two of R 30 to R 41Since in the above formula (B2-a1) each is a halogen, for the simple synthesis it is preferable that R is 31 or R 32 as well as R 37 or R 38 Each is a halogen. In this case, R is also 31 and R 37 each preferably by a halogen and at R 32 and R 38 each preferably involving a halogen.

[0109] Furthermore, in the above formula (B3-a1), one or two of R represent 50 to R 61 One of the atoms represents a single bond, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a halogenated hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. It should be noted that one halogen is preferably one or two of R 51 , R52 , R 57 and R 58 from R 50 to R 61 it.

[0110] Furthermore, in the case where there are two of R 50 to R 61 Since in the above formula (B3-a1) each is a halogen, for the simple synthesis it is preferable that R is 51 or R 52 as well as R 57 or R 58 Each is a halogen. In this case, R is also 51 and R 57 each preferably by a halogen and at R 52 and R 58 each preferably involving a halogen.

[0111] Furthermore, in the above formula (B4-a1), one or two of R represent 70 to R 81One halogen is represented, and the others each independently represent hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. It should be noted that one halogen is preferably one or two of R 71 , R 72 , R 77 and R 78 from R 70 to R 81 it.

[0112] Furthermore, in the case where there are two of R 70 to R 81 Since in the above formula (B4-a1) each is a halogen, for the simple synthesis it is preferable that R is 71 or R 72 as well as R 77 or R 78 Each is a halogen. In this case, R is also 71 and R 78each preferably by a halogen and at R 72 and R 77 each preferably involving a halogen. (Version 2)

[0113] An example of a light-emitting element that is an embodiment of the present invention is described below with reference to Fig. 1(A) described in detail.

[0114] In this embodiment, the light-emitting element comprises a pair of electrodes consisting of an anode 101 and a cathode 102, as well as an EL layer 103 located between the anode 101 and the cathode 102. The EL layer 103 is formed by stacking several functional layers, each containing at least one light-emitting layer 113. Typical examples of functional layers include a hole injection layer 111, a hole transport layer 112, the emitting layer 113, an electron transport layer 114, an electron injection layer 115, and the like. Furthermore, the functional layer may include a charge carrier blocking layer, an exciton blocking layer, a charge generation layer, or the like.

[0115] The anode 101 is preferably formed using a metal, alloy, or conductive compound with a high work function (particularly 4.0 eV or more), a mixture thereof, or the like. Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, and indium oxide containing tungsten oxide and zinc oxide (IWZO). Films of these conductive metal oxides are usually formed by a sputtering process, but they can also be formed by a sol-gel process or the like. Examples of the formation process include a process in which indium zinc oxide is formed by sputtering using a target containing 1 wt.% or more and 20 wt.% or less zinc oxide relative to the indium oxide.Furthermore, indium oxide containing tungsten oxide and zinc oxide (IWZO) can also be formed by a sputtering process using a target containing 0.5 wt% or more and 5 wt% or less tungsten oxide and 0.1 wt% or more and 1 wt% or less zinc oxide relative to indium oxide. Other suitable materials include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), aluminum (Al), a nitride of a metallic material (e.g., titanium nitride), and the like. Graphene can also be used. It should be noted that if a composite material containing a first substance and a second substance is used for the hole injection layer 111, an electrode material other than the one described above can be selected, regardless of the work function.

[0116] The hole injection layer 111 can be formed from a first substance with a relatively high acceptor property. It is also preferably formed from a composite material in which the first substance with an acceptor property and a second substance with a hole transport property are mixed. In the case where the composite material is used as the material of the hole injection layer 111, a substance exhibiting an acceptor property with respect to the second substance is used as the first substance. The first substance extracts electrons from the second substance, thus generating electrons in the first substance and creating holes in the second substance from which the electrons were extracted.Regarding the extracted electrons and the generated holes, an electric field causes the electrons to flow into the anode 101 and the holes to be injected via the hole transport layer 112 into the light-emitting layer 113. Thus, a light-emitting element with a low operating voltage can be obtained.

[0117] The first substance is preferably a transition metal oxide, an oxide of a metal belonging to one of groups 4 to 8 of the periodic table, an organic compound with an electron-withdrawing group (a halogen group or a cyano group) or the like.

[0118] The transition metal oxides or oxides of metals belonging to groups 4 to 8 of the periodic table, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, titanium oxide, ruthenium oxide, zirconium oxide, hafnium oxide, and silver oxide are preferred due to their high acceptor properties. Molybdenum oxide is particularly preferred because of its high stability in air, low hygroscopicity, and ease of handling.

[0119] Examples of organic compounds containing an electron-withdrawing group (a halogen group or a cyano group) 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-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and the like. In particular, a compound in which electron-withdrawing groups are bonded to a fused aromatic ring with a multitude of heteroatoms, such as HAT-CN, is thermally stable and preferable.

[0120] The second substance is a substance with a hole transport property and preferably has a hole mobility of 10 -6 cm 2 / Vs or higher. Materials that can be used as the second substance include aromatic amines, such as N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 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'-diamine (abbreviation: DNTPD) and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), carbazole derivatives, such as...3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-Di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-Tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA) and 1,4-Bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, as well as aromatic hydrocarbons, such as e.g.2-tert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-Butyl-9,10-di(1-naphthyl)anthracene, 9,10-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-Butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-Di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-Diphenylanthracene (abbreviation: DPAnth), 2-tert-Butylanthracene (abbreviation: t-BuAnth), 9,10-Bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) 2-tert-Butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-Tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-Bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, pentacene, coronene, rubrene, perylene and 2,5,8,11-Tetra(tert-butyl)perylene. The aromatic hydrocarbon may comprise a vinyl skeleton.Examples of aromatic hydrocarbons with a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi) and 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA). Alternatively, a compound with an aromatic amine skeleton, such as...4,4'-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-Phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-Phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-Diphenyl-4"-(9-phenyl-9-H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-Naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)-triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-fluoren-2-amine (abbreviation: PCBAF) or N-Phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), a compound with a carbazole skeleton, such as... B.1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP) or 3,3'-Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), a compound with a thiophene skeleton, such as... B. 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) or 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), or a compound with a furan skeleton, such as 4,4',4"-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) or 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).Among the above, the compound with an aromatic amine framework and the compound with a carbazole framework are preferred because they are reliable, have high hole transport properties and contribute to a reduction in operating voltage.

[0121] The organic compound of an embodiment of the present invention is also a substance with a hole transport property and can be used as a second substance.

[0122] Furthermore, the hole injection layer 111 can also be formed by a wet process. In this case, a conductive high-molecular-weight compound or the like can be used, to which an acid, such as an aqueous solution of poly(ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), an aqueous solution of polyaniline / camphorsulfonic acid (PANI / CSA), PTPDES, Et-PTPDEK, PPBA, or polyaniline / poly(styrenesulfonic acid) (PANI / PSS), is added.

[0123] The hole transport layer 112 is a layer containing a material with hole transport properties. The same material with hole transport properties as that used for the second substance specified in the preceding hole injection layer 111 can be used. The hole transport layer 112 can be formed from a single layer or from a plurality of layers. In the case where it is formed from a plurality of layers, it preferably has a structure for easy hole injection in which the HOMO level decreases stepwise from a layer on the side of the hole injection layer 111 towards a layer on the side of the light-emitting layer 113. Such a structure is very suitable for a blue fluorescent emitting element in which a host material in the light-emitting layer 113 has a low HOMO level.

[0124] It should be noted that the structure of the aforementioned hole transport layer 112, which is formed from a plurality of layers and in which the HOMO level decreases stepwise towards the light-emitting layer 113, is particularly suitable for an element in which the hole injection layer 111 is formed from an organic acceptor (an organic compound with the aforementioned electron-withdrawing group (a halogen group or a cyano group)); thus, a very advantageous element can be obtained which has good charge carrier injection properties and a low operating voltage.

[0125] The organic compound of an embodiment of the present invention is also a substance with a hole transport property and can be used as a material with a hole transport property.

[0126] It should be noted that the hole transport layer 112 can also be formed by a wet process. In the case where the hole transport layer 112 is formed by a wet process, a high molecular weight compound such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA) or poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: poly-TPD) can be used.

[0127] The light-emitting layer 113 can be a layer containing any light-emitting substance, such as a layer containing a fluorescent substance, a layer containing a phosphorescent substance, a layer containing a substance that emits thermally activated delayed fluorescence (TADF), a layer containing quantum dots, or a layer containing metal halide perovskites. Preferably, the organic compound described in embodiment 1 of an embodiment of the present invention is included as the light-emitting substance. By using the organic compound of an embodiment of the present invention as the light-emitting substance, a light-emitting element with high efficiency and very high chromaticity can be readily obtained.

[0128] Furthermore, the light-emitting layer 113 can consist of a single layer or a plurality of layers. In the case where a light-emitting layer is formed from a plurality of layers, a layer containing a phosphorescent substance and a layer containing a fluorescent substance can be arranged one above the other. Preferably, an exciplex described below is used in the layer containing the phosphorescent substance.

[0129] The organic compound of an embodiment of the present invention is also a substance with high quantum yield and can therefore be used as a light-emitting material.

[0130] The following substances, for example, can be used as fluorescent agents. Alternatively, other fluorescent substances can also be used. These include 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), (N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine), and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1.6mMemFLPAPrn). N,N'-Bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), Perylene, 2,5,8,11-Tetra(tert-butyl)perylene (abbreviation: TBP)4-(10-Phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), N,N"-(2-tert-Butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-Diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-Diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N",N",N"',N"'-Octaphenyldibenzo[g,p]chrysen-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N-(9,10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-Diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-Bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-Triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-Diphenylquinacridone (abbreviation: DPQd), Rubren, 5,12-Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(Dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanenitrile (abbreviation: DCM1), 2-{2-Methyl-6-[2-(2,3,6, 7-tetrahydro-1H,5H-benzo[i / ]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanenitrile (abbreviation: DCM2), N,N,N',N'-Tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-Diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-Isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanenitrile (abbreviation: DCJTI), 2-{2-tert-Butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-Bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM) and the like are specified. In particular, a condensed aromatic diamine compound, typically a pyrenediamine compound such as 1,6mMemFLPAPRn, is preferred because it has high hole-trapping properties and is characterized by emission efficiency and reliability.

[0131] Examples of materials that can be used as phosphorescent substances in the light-emitting layer 113 include a metal-organic iridium complex with a 4H-triazole framework, such as... B. Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]) or Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]), an organometallic iridium complex with a 1H-triazole skeleton, such as e.g. B. Tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) or Tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), a metal-organic iridium complex with an imidazole skeleton, such asfac-Tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]) or Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), as well as an organometallic iridium complex in which a phenylpyridine derivative with an electron-withdrawing group serves as a ligand, such as Bis[2-(4',6'-difluorophenyl)pyridinato-N,C. 2' ]iridium(III)-tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]iridium(III) picolinate (abbreviation: FIrpic), Bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2'}iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) or Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' [Iridium(III) acetylacetonate (abbreviation: Flracac) is listed. These are compounds that emit blue phosphorescence and have an emission peak at 440 nm to 520 nm.

[0132] Furthermore, a metal-organic iridium complex with a pyrimidine framework, such as... B. Tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (Acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (Acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (Acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]) or (Acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), a metal-organic iridium complex with a pyrazine backbone, such as(Acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) or (Acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), a metal-organic iridium complex with a pyridine skeleton, such as Tris(2-phenylpyridinato-N,C. 2' )iridium(III) (abbreviation: [Ir(ppy)3]), Bis(2-phenylpyridinato-N,C 2' )iridium(III)-acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), Bis(benzo[h]quinolinato)iridium(III)-acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), Tris(2-phenylquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(pq)3]) or bis(2-phenylquinolinato-N,C 2'Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]) and a rare-earth metal complex, such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]), are specified. These are compounds that mainly emit green phosphorescence and exhibit emission peaks at 500 nm to 600 nm. It should be noted that a metal-organic iridium complex with a pyrimidine framework is particularly preferred, as it is distinguished by both reliability and emission efficiency.

[0133] Furthermore, a metal-organic iridium complex with a pyrimidine backbone, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]) or bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), a metal-organic iridium complex with a pyrazine backbone, such as... B. (Acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), Bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]) or (Acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), an organometallic iridium complex with a pyridine skeleton, such as Tris(1-phenylisoquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(piq)3]) or Bis(1-phenylisoquinolinato-N,C 2')iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), a platinum complex, such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatin(II) (abbreviation: PtOEP), and a rare earth metal complex, such as Tris(1,3-diphenyl-1,3-propanediumato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) or Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]). These are compounds that emit red phosphorescence and exhibit emission peaks at 600 nm to 700 nm. Furthermore, a high-chromatic red light emission can be obtained from a metal-organic iridium complex with a pyrazine framework.

[0134] In addition to the above phosphorescent compounds, various phosphorescent materials can be selected and used.

[0135] A fullerene, a derivative thereof, an acridine, a derivative thereof, an eosin derivative, or the like can be used as the TADF material. Furthermore, a metal-containing porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), or the like can be used. Examples of metal-containing porphyrins include a protoporphyrin-tin fluoride complex (SnF2(Proto IX)), a mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), a hematoporphyrin-tin fluoride complex (SnF2(Hämato IX)), a coproporphyrin-tetramethyl ester-tin fluoride complex (SnF2(Kopro III-4Me)), an octaethylporphyrin-tin fluoride complex (SnF2(OEP)), an etioporphyrin-tin fluoride complex (SnF2(Etio I)) and an octaethylporphyrin-platinum chloride complex (PtCl2OEP), which are represented by the following structural formulas.

[0136] Furthermore, a heterocyclic compound comprising both a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring, such as... B. 2-(Biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn) (Abbreviation: PXZ-TRZ), 3-[4-(5-Phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), Bis[4-(9,9-dimethyl-9,10-dihydroacridin)phenyl]sulfone (abbreviation: DMAC-DPS) or 10-Phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), which are represented by the following structural formulas.Since the heterocyclic compound comprises a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring, both its electron transport and hole transport properties are high, which is preferable. It should be noted that a substance in which a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring are directly bonded to one another is particularly preferred, as both the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-poor heteroaromatic ring are enhanced, and the energy difference between the S1 level and the T1 level is reduced, thus enabling thermally activated delayed fluorescence to be obtained efficiently. It should be noted that an aromatic ring to which an electron-withdrawing group, such as...a cyano group, which is bound, can be used instead of the π-electron-deficient heteroaromatic ring.

[0137] Furthermore, nanometer-sized particles of an element of group 14, an element of group 15, an element of group 16, a compound of a multitude of elements of group 14, a compound of an element belonging to one of groups 4 to 14 and an element of group 16, a compound of an element of group 2 and an element of group 16, a compound of an element of group 13 and an element of group 15, a compound of an element of group 13 and an element of group 17, a compound of an element of group 14 and an element of group 15, a compound of an element of group 11 and an element of group 17, as well as those of iron oxides, titanium oxides, spinel chalcogenides, semiconductor clusters, metal halide perovskites and the like, can be specified as quantum dots.

[0138] In particular, but not limited to, cadmium selenide (CdSe), cadmium sulfide (CdS), cadmium telluride (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 (GaSb), aluminum phosphide (AIP), aluminum arsenide (AlAs), aluminum antimonide (AlSb), lead(II) selenide (PbSe), lead(II) telluride (PbTe), Lead(II) sulfide (PbS), indium selenide (In2Se3), indium telluride (In2Te3), indium sulfide (In2S3), gallium selenide (Ga2Se3), arsenic(III) sulfide (As2S3), arsenic(III) selenide (As2Se3), arsenic(III) telluride (As2Te3), antimony(III) sulfide (Sb2S3), antimony(III)selenide (Sb2Se3), antimony(III)telluride (Sb2Te3), bismuth(III)sulfide (Bi2S3), bismuth(III)selenide (Bi2Se3), bismuth(III)telluride (Bi2Te3), silicon (Si),Silicon Carbide (SiC), Germanium (Ge), Zinc (Sn), Selenium (Se), Tellurium (Te), Boron (B), Carbon (C), Phosphorus (P), Bornitride (BN), Borphosphide (BP), Borarsenide (BAs), Aluminum Nitride (AIN), Aluminum Sulfide (Aluminum Sulfide), Barium (S2S3), Barium Selenide (BaSe), Barium Telluride (BaTe), Calcium Sulfide (CaS), Calcium Selenide (CaSe), Calcium Telluride (CaTe), Beryllium Sulfide (BeS), Beryllium Selenide (BeSe), Beryllium Telluride (BeTe), Magnesium Sulfide (MgS), Magnesium Sulfide (MgS (GeS), Germanium selenide (GeSe), Germanium telluride (GeTe), Zinc(IV)sulfide (SnS2), Zinc(II)sulfide (SnS), Zinc(II)selenide (SnSe), Zinc(II)telluride (SnTe), Lead(II)oxide (PbO), Copper(I)Fluoride, Cupric(I)fluoride (CuCl), Copper(I)bromide (CuBr), Copper(I)iodide (CuI), Copper(I)oxide (Cu2O), Copper(I)selenide (Cu2Se), Nickel(II)oxide (NiO), Cobalt(II)oxide (CoO), Cobalt(II)sulfide (CoS), Trioxide (CoS), Trioxide Iron(II)sulfide (FeS), Manganese(II)oxide (MnO), Molybdenum(IV)sulfide (MoS2), Vanadium(II)oxide (VO),Vanadium(IV) oxide (VO2), tungsten(IV) oxide (WO2), tantalum(V) oxide (Ta2O5), titanium oxide (e.g., TiO2, Ti2O5, Ti2O3, or Ti5O9), zirconium oxide (ZrO2), silicon nitride (Si3N4), germanium nitride (Ge3N4), aluminum oxide (Al2O3), barium titanate (BaTiO3), a compound of selenium, zinc, and cadmium (CdZnSe), a compound of indium, arsenic, and phosphorus (InAsP), a compound of cadmium, selenium, and sulfur (CdSeS), a compound of cadmium, selenium, and tellurium (CdSeTe), a compound of indium, gallium, and arsenic (InGaAs), a compound of indium, gallium, and selenium (InGaSe), a compound of indium, selenium, and sulfur (InSeS), a compound of copper, indium, and sulfur (e.g., CuInS2), and Combinations thereof can be specified. Furthermore, a so-called alloyed quantum dot can be used, the composition of which is represented by a given ratio. For example, an alloyed quantum dot composed of CdS, x See 1-x(x is a given number from 0 to 1) is represented as an effective means of obtaining blue light emission, since the emission wavelength can be changed by changing x.

[0139] The quantum dot structure can be a core-type, core-shell, core-multishell, or similar design, and any one of these can be used. When a core is covered with a shell made of another inorganic material with a wider band gap, the influence of a defect or free bond present on the surface of a nanocrystal can be reduced. This greatly improves the quantum efficiency of light emission; therefore, a core-shell or core-multishell quantum dot is preferred. Examples of shell materials include zinc sulfide (ZnS) and zinc oxide (ZnO).

[0140] Furthermore, quantum dots are highly reactive due to their high surface atom content and readily cohere with each other. For this reason, a protecting agent or protecting group is preferably applied to the surfaces of the quantum dots. Applying the protecting agent or providing the protecting group can prevent cohesion and increase solubility in a solvent. It can also reduce reactivity and improve electrical stability. Examples of protecting agents (or protecting groups) include polyoxyethylene alkyl ethers, such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; trialkyl phosphines, such as tripropyl phosphine, tributyl phosphine, trihexyl phosphine, and trioctyl phosphine; polyoxyethylene alkyl phenyl ethers, such as polyoxyethylene n-octyl phenyl ether and polyoxyethylene n-nonyl phenyl ether; and tertiary amines, such as...Tri(n-hexyl)amine, tri(n-octyl)amine and tri(n-decyl)amine, organophosphorus compounds, such as tripropylphosphine oxide, tributylphosphine oxide, trihexylphosphine oxide, trioctylphosphine oxide and tridecylphosphine oxide, polyethylene glycol diesters, such as polyethylene glycol dilaurate and polyethylene glycol distearate, organic nitrogen compounds, such as nitrogenous aromatic compounds, for example pyridines, lutidines, collidines and quinolines, aminoalkanes, such as hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine and octadecylamine, dialkyl sulfides, such as dibutyl sulfide, dialkyl sulfoxides, such as dimethyl sulfoxide and dibutyl sulfoxide, organic sulfur compounds, such as... B. sulfur-containing aromatic compounds, such as thiophene, higher fatty acids, such as e.g.Palmitic acid, stearic acid and oleic acid, alcohols, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes and polyethyleneimines are listed.

[0141] It should be noted that quantum dots can also be rod-shaped quantum rods. A quantum rod emits directional light that is polarized along the c-axis; therefore, by using quantum rods as the light-emitting material, a light-emitting element with high external quantum efficiency can be obtained.

[0142] It should be noted that in the case where a light-emitting layer is formed in which the quantum dots are dispersed as light-emitting material in a host, it can be formed as follows: The quantum dots are dispersed in the host material, or the host material and the quantum dots are dissolved or dispersed in a suitable liquid medium, a wet process (e.g., a rotary coating process, a casting process, a nozzle coating process, a blade coating process, a roller coating process, an inkjet process, a printing process, a spray coating process, a curtain coating process, or a Langmuir-Blodgett process) is carried out to form a layer, and then the solvent is removed or baking is carried out.

[0143] Examples of liquid media used for the wet process include organic solvents such as ketones, e.g., methyl ethyl ketone and cyclohexanone; fatty acid esters, e.g., ethyl acetate; halogenated hydrocarbons, e.g., dichlorobenzene; aromatic hydrocarbons, e.g., toluene, xylene, mesitylene and cyclohexylbenzene; aliphatic hydrocarbons, e.g., cyclohexane, decalin and dodecane; dimethylformamide (DMF); and dimethyl sulfoxide (DMSO).

[0144] In the case where a fluorescent substance is used, a material with an anthracene framework, such as... B. 9-Phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-Naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-Phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-Diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA) or 9-Phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}anthracene (abbreviation: FLPPA) is preferred as the host material for the light-emitting layer. When a substance with an anthracene backbone is used as the host material for a fluorescent substance, a light-emitting layer can be obtained with both high emission efficiency and stability.In particular, CzPA, cgDBCzPA, 2mBnfPPA and PCzPA have excellent properties and are therefore preferably selected.

[0145] In the case where a material other than the aforementioned materials is used as the host material, various charge carrier transport materials, such as a material with an electron transport property and a material with a hole transport property, can be used.

[0146] Examples of materials with electron transport properties include a metal complex, such as bis(10-hydroxybenzo[h]-quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) or bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), a heterocyclic compound with a polyazole skeleton, such as...2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-Biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-Bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) or 2-[3-(Dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), a heterocyclic compound with a diazine backbone, such as e.g.2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-Carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm) or 4,6-Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), as well as a heterocyclic compound with a Pyridine skeletons, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) or 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), are specified. Of the above, the heterocyclic compound with a diazine skeleton and the heterocyclic compound with a pyridine skeleton are preferred because they are reliable.In particular, the heterocyclic compound with a diazine (pyrimidine or pyrazine) framework exhibits high electron transport properties and also contributes to a reduction in operating voltage.

[0147] Materials with hole transport properties can include compounds with an aromatic amine skeleton, such as...4,4'-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-Phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-Phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-Diphenyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-Naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF) or N-Phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), a compound with a carbazole skeleton, such as1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP) or 3,3'-Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), a compound with a thiophene skeleton, such as... B. 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) or 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), as well as a compound with a furan skeleton, such as 4,4',4"-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) or 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).Among the above, the compound with an aromatic amine framework and the compound with a carbazole framework are preferred because they are reliable, exhibit high hole transport properties, and contribute to a reduction in operating stress. In addition to the above hole transport materials, a hole transport material selected from various substances can be used.

[0148] In the case where a fluorescent substance is used as a light-emitting substance, a material with an anthracene framework, such as... B. 9-Phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-Naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-Phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-Diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA) or 9-Phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}anthracene (abbreviation: FLPPA), preferably. When a substance with an anthracene backbone is used as a host material for a fluorescent substance, a light-emitting layer can be obtained in which both emission efficiency and stability are advantageous.In particular, CzPA, cgDBCzPA, 2mBnfPPA and PCzPA have excellent properties and are therefore preferably selected.

[0149] It should be noted that a host material can be a mixture of several types of substances; in the case of using a mixed host material, a material with electron transport properties and a material with hole transport properties are preferably mixed together. By mixing a material with electron transport properties and a material with hole transport properties, the transport properties of the light-emitting layer 113 can be easily controlled, and the control of a recombination region can be carried out in a simple manner. The following ratio of the content of the material with hole transport properties to that of the material with electron transport properties can apply: the material with hole transport properties : the material with electron transport properties = 1:9 to 9:1.

[0150] Furthermore, these mixed host materials can form an exciplex. Regarding the exciplex, a combination is selected such that an exciplex is formed which emits light with a wavelength that overlaps those of the absorption bands on the lowest energy side of a fluorescent substance, a phosphorescent substance, and a TADF material, thereby enabling rapid and easy energy transfer and efficient light emission. Moreover, such a structure is preferred because the operating voltage can also be reduced.

[0151] The light-emitting layer 113 with the above structure can be formed by co-evaporation using a vacuum evaporation process or by a process using a mixed solution, such as a gravure printing process, an offset printing process, an inkjet printing process, a rotary coating process, a dip coating process or the like.

[0152] The electron transport layer 114 is a layer containing a substance with electron transport properties. The substance with electron transport properties can be a material specifically designated as having electron transport properties, or a material with an anthracene framework that can be used as the host material.

[0153] A layer controlling electron carrier transport can also be provided between the electron transport layer and the light-emitting layer. This layer consists of a small amount of a substance with high electron capture properties added to the aforementioned material with high electron transport properties. By preventing electron carrier transport, this layer regulates the charge carrier balance. Such a structure is very effective in preventing problems (such as a reduction in the element's lifetime) that occur when electrons pass through the light-emitting layer.

[0154] An electron injection layer 115 can also be provided in contact with the cathode 102 between the electron transport layer 114 and the cathode 102. An alkali metal, an alkaline earth metal, or a compound thereof, such as lithium fluoride (LiF), cesium fluoride (CsF), or calcium fluoride (CaF₂), can be used for the electron injection layer 115. For example, a layer consisting of a substance with electron transport properties and containing an alkali metal, an alkaline earth metal, or a compound thereof can be used. An electride can also be used for the electron injection layer 115. An electride, for example, is a substance in which electrons are added to a calcium-aluminum mixed oxide in high concentrations.It should be noted that a layer consisting of a substance with an electron transport property and containing an alkali metal or an alkaline earth metal is preferably used as an electron injection layer 115, in which case electron injection from the cathode 102 is carried out efficiently.

[0155] Instead of the electron injection layer 115, a charge generation layer 116 can also be provided ( Fig. 1(B)). The charge-generating layer 116 is a layer that can inject holes into a layer in contact with the cathode side of this layer and electrons into a layer in contact with the anode side when a potential is applied to it. The charge-generating layer 116 comprises at least one P-type layer 117. The P-type layer 117 is preferably formed using the composite material identified above as a material suitable for the hole-injection layer 111. Furthermore, the P-type layer 117 can have a structure in which a film containing the aforementioned acceptor material as a component of the composite material and a film containing a hole-transport material are arranged one above the other.When a potential is applied 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. If a layer containing the organic compound of an embodiment of the present invention exists at the position in the electron transport layer 114 where it is in contact with the charge-generating layer 116, a decrease in luminance during the operating lifetime of the light-emitting element can be prevented, thus enabling a long-life light-emitting element.

[0156] It should be noted that the charge generation layer 116 is preferably provided with an electron conduction layer 118 and / or an electron injection buffer layer 119 in addition to the P-type layer 117.

[0157] The electron conduction layer 118 contains at least one substance with electron transport properties and has a function for preventing interaction between the electron injection buffer layer 119 and the P-type layer 117, in order to transfer electrons quickly and easily. The LUMO level of the substance with electron transport properties contained in the electron conduction layer 118 is preferably between the LUMO level of an acceptor substance in the P-type layer 117 and the LUMO level of a substance contained in a layer located in the electron transport layer 114 and in contact with the charge generation layer 116. The specific LUMO energy level of the substance with an electron transport property used for the electron conduction layer 118 is particularly preferably higher than or equal to -5.0 eV, more preferably higher than or equal to -5.0 eV and lower than or equal to -3.0 eV.It should be noted that the substance with an electron transport property used for the electron conduction layer 118 is preferably a phthalocyanine-based material or a metal complex comprising a metal-oxygen bond and an aromatic ligand.

[0158] For the electron injection buffer layer 119, a substance with high electron injection properties can be used, such as an alkali metal, an alkaline earth metal, a rare earth metal or a compound thereof (an alkali metal compound (including an oxide, such as lithium oxide, a halide and a carbonate, such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide and a carbonate) or a rare earth metal compound (including an oxide, a halide and a carbonate)).

[0159] Furthermore, in the case where the electron injection buffer layer 119 is designed to contain the substance with an electron transport property and a donor substance, an organic compound such as tetrathianaphthacene (abbreviation: TTN), nickelocene or decamethylnickelocene can also be used as the donor substance, as well as an alkali metal, an alkaline earth metal, a rare earth metal and a compound thereof (an alkali metal compound (including an oxide, such as lithium oxide, a halide and a carbonate, such as lithium carbonate or cesium carbonate), an alkaline earth metal compound (including an oxide, a halide and a carbonate) or a rare earth metal compound (including an oxide, a halide and a carbonate)).It should be noted that a material similar to the material described above for the electron transport layer 114 can be used as a substance with an electron transport property.

[0160] The substance used to form the cathode 102 can be a metal, alloy, or electrically conductive compound with a low work function (especially 3.8 eV or lower), a mixture thereof, or the like. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (MgAg and AlLi), rare-earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. However, once the electron injection layer between the cathode 102 and the electron transport layer is provided, various conductive materials can be used for the cathode 102, such as...Aluminum, silver, ITO, or indium oxide-tin oxide containing silicon or silicon oxide can be used, regardless of the work function. These conductive materials can be deposited by a dry process, such as vacuum evaporation, sputtering, inkjet printing, spin coating, or similar methods. Alternatively, they can be formed by a wet process using a sol-gel process, or by a wet process using a paste of the metallic material.

[0161] Various processes can be used to form the EL layer 103, regardless of whether it is a dry or wet process. For example, a vacuum evaporation process or a wet process (such as a rotary coating process, a casting process, a nozzle coating process, a blade coating process, a roller coating process, an inkjet process, a printing process (e.g., a gravure printing process, an offset printing process, or a screen printing process), a spray coating process, a curtain coating process, or a Langmuir-Blodgett process) can be used.

[0162] The electrodes or layers described above can be formed by different deposition processes.

[0163] Now, a process in which a layer 786 containing a light-emitting substance is formed by a droplet ejection process is described using the following examples: Fig. 2 described. Fig. 2(A) to Fig. 2(D) are cross-sectional views showing a formation process of layer 786 containing a light-emitting substance.

[0164] First, a guiding film 772 is formed over an isolating planarizing film 770, and an isolating film 730 is formed such that it covers part of the guiding film 772 (see Fig. 2(A)).

[0165] Next, a droplet 784 is ejected from a droplet ejection device 783 onto an exposed section of the conductive film 772, i.e., an opening in the insulating film 730, so that a layer 785 containing a composition is formed. The droplet 784 is a composition containing a solvent and adheres to the conductive film 772 (see Fig. 2(B)).

[0166] It should be noted that the step to eject droplet 784 can be carried out under reduced pressure.

[0167] Next, the solvent is removed from layer 785 containing a composition, and then a solidification process is carried out to form layer 786 containing a light-emitting substance (see Fig. 2(C)).

[0168] It should be noted that a drying step or a heating step can be used as a method for removing the solvent.

[0169] Next, a conductive film 788 is formed over the layer 786 containing a light-emitting substance; consequently, a light-emitting element 782 is formed (see Fig. 2(D)).

[0170] If the layer 786 containing a light-emitting substance is formed in this way by a droplet ejection process, the composition can be selectively ejected; consequently, material loss can be reduced. Furthermore, no lithography process or the like is required for forming, and therefore the process can also be simplified and a cost reduction can be achieved.

[0171] It should be noted that the droplet ejection method described above is a general term for a method using a droplet ejection means, such as a nozzle incorporating a composition ejection orifice, or a head incorporating one or more nozzles.

[0172] Next, a droplet ejection device used in the droplet ejection process will be described using the following examples: Fig. 3 described. Fig. Figure 3 is a conceptual representation depicting a droplet ejection device 1400.

[0173] The droplet ejection device 1400 includes a droplet ejection medium 1403. The droplet ejection medium 1403 further includes a head 1405, a head 1412 and a head 1416.

[0174] The head 1405, the head 1412 and the head 1416 are connected to a control device 1407 which is controlled by a computer 1410; consequently, a pre-programmed pattern can be drawn.

[0175] Furthermore, the drawing can be carried out, for example, at a time based on a marking 1411 formed on a substrate 1402. Alternatively, the reference point can be determined based on an outer edge of the substrate 1402. Here, the marking 1411 is detected by an imaging device 1404 and converted into a digital signal by an image processing device 1409. The computer 1410 recognizes this signal, generates a control signal, and transmits it to the control device 1407.

[0176] An image sensor or the like, in which a charge-coupled device (CCD) or a complementary metal-oxide semiconductor (CMOS) is used, can be used as the imaging device 1404. It should be noted that information about a pattern to be formed on the substrate 1402 is stored in a storage medium 1408 and that a control signal based on this information is transmitted to the control device 1407, so that the head 1405, the head 1412, and the head 1416 of the droplet ejection device 1403 can be controlled separately. Materials to be ejected are supplied to the head 1405, the head 1412, and the head 1416 from a material supply source 1413, a material supply source 1414, and a material supply source 1415, respectively, via tubes.

[0177] Head 1405 has an internal structure that includes a chamber, represented by a dashed line 1406, filled with a liquid material, and a nozzle serving as an outlet. Although not shown, the internal structures of heads 1412 and 1416 are similar to those of head 1405. If the nozzles of heads 1405, 1412, and 1416 are provided in such a way that they are of different sizes, different materials of varying widths can be ejected simultaneously. Each head can eject several types of light-emitting materials or the like for drawing. In the case of drawing over a wide area, the same material can be ejected from a multitude of nozzles simultaneously to improve throughput.In the case of using a large substrate, the head 1405, the head 1412 and the head 1416 can move the substrate in the directions of the arrows X, Y and Z shown in . Fig. As shown in the 3 examples, the area can be freely scanned, and the area to be drawn can be freely defined. Therefore, the same pattern can be drawn multiple times on a substrate.

[0178] Furthermore, the ejection step can be performed under reduced pressure. During ejection, the substrate can be heated. Ejection is followed by a drying and / or baking step. Both steps—drying and baking—are heat treatment steps; however, they differ in purpose, temperature, and duration. The drying and baking steps are performed by laser irradiation, rapid thermal curing, a heating oven, or similar methods under normal or reduced pressure. It should be noted that there is no particular restriction regarding the timing of these heat treatments or the number of treatments. The appropriate temperature for the drying and baking steps depends on the substrate material and the properties of the composition.

[0179] In the above manner, the layer 786 containing a light-emitting substance can be formed with the droplet ejection device.

[0180] In the case where the layer 786 containing a light-emitting substance is formed by a wet process using a composition in which organic materials or organic-inorganic halide perovskites are dissolved or dispersed in a solvent, various organic solvents can be used to obtain a coating composition. Various organic solvents, such as benzene, toluene, xylene, mesitylene, tetrahydrofuran, dioxane, ethanol, methanol, n-propanol, isopropanol, n-butanol, t-butanol, acetonitrile, dimethyl sulfoxide, dimethylformamide, chloroform, methylene chloride, carbon tetrachloride, ethyl acetate, hexane, and cyclohexane, can be used for the above composition. In particular, a slightly polar benzene derivative, such as...Benzene, toluene, xylene, or mesitylene are preferably used because a solution with a suitable concentration can be prepared and deterioration of a material contained in an ink due to oxidation or the like can be prevented. Furthermore, toluene, xylene, or mesitylene are preferred because a boiling point of 100°C or higher is desirable when considering the uniformity of the formed film, the uniformity of the film thickness, and the like.

[0181] It should be noted that the above structure can be appropriately combined with other structures of the other embodiments and this embodiment.

[0182] The following describes an embodiment of a light-emitting element in which several light-emitting units are arranged one above the other (also referred to as a multilayer element), using the following examples: Fig. 1(C) described. This light-emitting element is a light-emitting element that includes a plurality of light-emitting units between an anode and a cathode. A light-emitting unit has a structure similar to that of the one described in Fig. The EL layer 103 shown in 1(A) is similar. In other words, the one shown in Fig. 1(A) or Fig. 1(B) the light-emitting element shown is a light-emitting element that includes a single light-emitting unit, whereas the one in Fig. The light-emitting element shown in Figure 1(C) is a light-emitting element that includes a plurality of light-emitting units.

[0183] In Fig. 1(C) is an EL layer 503 comprising a first light-emitting unit 511 and a second light-emitting unit 512, arranged between a first electrode 501 and a second electrode 502, and a charge-generating layer 513 is provided between the first light-emitting unit 511 and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the anode 101 and the cathode 102, respectively, in Fig. 1(A), and the description of Fig. 1(A) can be applied to it. Furthermore, the first light-emitting unit 511 and the second light-emitting unit 512 can have the same structure or different structures.

[0184] The charge-generating layer 513 has a function for injecting electrons into one of the light-emitting units and for injecting holes into the other light-emitting unit when a voltage is applied between the first electrode 501 and the second electrode 502. That is to say, in Fig. 1(C) the charge-generating layer 513 injects electrons into the first light-emitting unit 511 and injects holes into the second light-emitting unit 512 when a voltage is applied such that the potential of the first electrode is higher than the potential of the second electrode.

[0185] Preferably, the charge generation layer 513 is formed with a structure similar to that of the one described by Fig. The charge-generating layer 116 described in Section 1(B) is similar. A composite material consisting of an organic compound and a metal oxide exhibits charge carrier injection and charge carrier transport properties; therefore, low-voltage and low-current operation can be achieved. It should be noted that if a surface of a light-emitting unit on the anode side is in contact with the charge-generating layer 513, the charge-generating layer 513 can also serve as a hole injection layer for the light-emitting unit; therefore, a hole injection layer does not necessarily have to be provided in the light-emitting unit.

[0186] In the case where the charge generation layer 513 is further provided with the electron injection buffer layer 119, this layer serves as an electron injection buffer layer in the light-emitting unit on the anode side; therefore, a further electron injection layer does not necessarily have to be formed in the light-emitting unit.

[0187] The light-emitting element, which contains two light-emitting units, is defined by Fig. 1(C); however, the present invention can also be applied to a light-emitting element in which three or more light-emitting units are arranged one above the other. If, as in the light-emitting element of this embodiment, a plurality of light-emitting units separated by the charge-generating layer 513 are arranged between a pair of electrodes, an element can be obtained that can emit light with high luminance at a low current density and has a longer lifetime. Furthermore, a light-emitting device can be obtained that can be operated at a low voltage and has low power consumption.

[0188] Furthermore, if the emission colors of the light-emitting units differ from one another, a light emission of a desired color can be obtained from the light-emitting element as a whole. (Version 3)

[0189] In this embodiment, a light-emitting device is described in which the light-emitting element described in embodiment 1 is used.

[0190] A light-emitting device of an embodiment of the present invention is described by means of Fig. 4 described. It should be noted that Fig. 4(A) a top view showing the light-emitting device is and Fig. 4(B) is a cross-sectional view obtained by cutting from Fig. 4(A) along AB and CD. This light-emitting device includes a driver circuit section (source line driver circuit) 601, a pixel section 602, and a driver circuit section (gate line driver circuit) 603, which control the light emission of a light-emitting element and are represented by dotted lines. Additionally, 604 represents a sealing substrate, 605 represents a sealing agent, and a space 607 is located in an inner part surrounded by the sealing agent 605.

[0191] It should be noted that a connecting line 608 is a line for transmitting signals input to the source line driver circuit 601 and the gate line driver circuit 603, and it receives a video signal, a clock signal, a start signal, a reset signal, and the like from an FPC (flexible printed circuit) 609, which serves as an external input terminal. It should be noted that, although only the FPC is shown here, a printed circuit board (PWB) can be attached to this FPC. The light-emitting device in this description includes not only the light-emitting device itself, but also any device fitted with the FPC or the PWB.

[0192] Next, a cross-sectional structure will be created based on... Fig. 4(B) described. The driver circuit section and the pixel section are formed on an element substrate 610. Here, the source line driver circuit 601, which is the driver circuit section, and a pixel in the pixel section 602 are shown.

[0193] It should be noted that the source line driver circuit 601 is a CMOS circuit in which an n-channel FET 623 and a p-channel FET 624 are combined. Furthermore, the driver circuit can be configured from various CMOS, PMOS, or NMOS circuits. In addition, a driver-integrated type is described in this embodiment, in which the driver circuit is implemented above the substrate; however, the driver circuit does not necessarily have to be implemented above the substrate and can be implemented externally.

[0194] Furthermore, the pixel section 602 is formed from a plurality of pixels, each containing a switching FET 611, a current-controlling FET 612, and a first electrode 613 electrically connected to its drain. Not limited to this, a pixel section can be used in which three or more FETs are combined with a capacitor.

[0195] There is no particular restriction regarding the type and crystallinity of a semiconductor used for the FETs; an amorphous semiconductor or a crystalline semiconductor may be used. Semiconductors used for the FETs may include, for example, Group 13 semiconductors, Group 14 semiconductors, compound semiconductors, oxide semiconductors, and organic semiconductors. Oxide semiconductors are preferred in particular. Examples of oxide semiconductors include In-Ga oxide and In-M-Zn oxide (where M is Al, Ga, Y, Zr, La, Ce, or Nd). It should be noted that an oxide semiconductor material having an energy gap of 2 eV or more, preferably 2.5 eV or more, and more preferably 3 eV or more, is preferred, in which case the reverse current of the transistors may be reduced.

[0196] It should be noted that an insulator 614 is designed such that it covers an end section of the first electrode 613. Here, it can be formed using a positive photosensitive acrylic resin film.

[0197] To improve coverage, the insulator 614 is also designed to have a curved surface with a curvature at its upper or lower end section. For example, if a positive photosensitive acrylic is used as the material of the insulator 614, preferably only the upper end section of the insulator 614 has a curved surface with a radius of curvature (0.2 µm to 3 µm). Additionally, either a negative photosensitive resin or a positive photosensitive resin can be used as the insulator 614.

[0198] Above the first electrode 613, an EL layer 616 and a second electrode 617 are formed. These correspond to the anode 101, the EL layer 103 and the cathode 102, which are defined by Fig. 1(A) have been described, or the first electrode 501, the EL layer 503 and the second electrode 502, which are based on Fig. have been described in 1(C).

[0199] The EL layer 616 preferably contains a metal-organic complex. The metal-organic complex is preferably used as an emission center substance in the light-emitting layer.

[0200] Furthermore, the sealing substrate 604 is attached to the element substrate 610 by means of the sealing agent 605, thus obtaining a structure in which a light-emitting element 618 is provided in the space 607 enclosed by the element substrate 610, the sealing substrate 604, and the sealing agent 605. It should be noted that the space 607 is filled with a filler; in some cases, it is filled with an inert gas (e.g., nitrogen or argon), and in other cases, it is filled with the sealing agent 605. Preferably, a depression is formed in the sealing substrate to provide a desiccant; thus, deterioration due to the influence of moisture can be prevented.

[0201] An epoxy-based resin or a glass frit is preferably used as the sealant 605. Furthermore, these materials are preferably materials that allow as little moisture or oxygen permeation as possible. Additionally, a plastic substrate made of FRP (fiber-reinforced plastic), PVF (polyvinyl fluoride), polyester, acrylic, or the like, as well as a glass substrate or a quartz substrate, can be used as materials for the element substrate 610 and the sealant substrate 604.

[0202] In this description and similar examples, a transistor and a light-emitting element can be formed using various substrates. The substrate type is not limited to any one particular type. Examples of substrates include a semiconductor substrate (e.g., a single-crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate containing stainless steel foil, a tungsten substrate, a substrate containing tungsten foil, a flexible substrate, a mounting film, paper containing a fiber material, and a base material film. Examples of glass substrates include barium borosilicate glass, aluminum borosilicate glass, and soda-lime glass. Examples of flexible substrates, mounting films, base material films, and the like include the following.These examples include plastics, such as typically polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES). Another example is a synthetic resin, such as acrylic. Further examples are polytetrafluoroethylene (PTFE), polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Other examples include polyamide, polyimide, aramid, epoxy, an evaporation-formed inorganic film, and paper. When transistors are fabricated using a semiconductor substrate, a single-crystal substrate, an SOI substrate, or the like, small transistors can be produced with minimal variation in properties, size, shape, or the like, and which exhibit high current capability. When a circuit is formed from such transistors, the circuit's power consumption can be reduced, and the circuit can be integrated to a higher degree.

[0203] Furthermore, a flexible substrate can be used, and the transistor or light-emitting element can be formed directly on top of the flexible substrate. Alternatively, a separating layer can be provided between the substrate and the transistor or between the substrate and the light-emitting element. The separating layer can be used to separate a semiconductor device, partially or completely formed on top of it, from the substrate and transfer it to another substrate. The transistor can also be transferred to a substrate with low thermal resistance or to a flexible substrate.It should be noted that for the separating layer described above, for example, a structure in which inorganic films, namely a tungsten film and a silicon oxide film, are arranged on top of each other, or a structure in which an organic resin film made of polyimide or the like is formed over a substrate can be used.

[0204] In other words, the transistor or light-emitting element can be formed using a substrate, and then the transistor or light-emitting element can be transferred to another substrate to position the transistor or light-emitting element above the other substrate. Examples of the substrate onto which the transistor or light-emitting element is transferred include, in addition to the substrates described above over which the transistor can be formed, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a rock substrate, a wood substrate, a fabric substrate (including a natural fiber (silk, cotton, or hemp), a synthetic fiber (nylon, polyurethane, or polyester), a regenerated fiber (acetate, cupro, viscose, or regenerated polyester), or the like), a leather substrate, and a rubber substrate.Using such a substrate allows for the creation of a transistor with excellent properties, a transistor with low power consumption, the production of a durable device, the imparting of heat resistance, a reduction in weight, or a reduction in thickness.

[0205] Fig. Figure 5 presents examples of a light-emitting device in which a light-emitting element emitting white light is formed and color layers (color filters) and the like are provided to enable a full-color display. Fig. 5(A) represents a substrate 1001, an insulating base film 1002, a gate insulating film 1003, gate electrodes 1006, 1007 and 1008, a first insulating intermediate film 1020, a second insulating intermediate film 1021, a peripheral section 1042, a pixel section 1040, a driver circuit section 1041, first electrodes 1024W, 1024R, 1024G and 1024B of light-emitting elements, a partition 1025, an EL layer 1028, a cathode 1029 of the light-emitting elements, a sealing substrate 1031, a sealing agent 1032 and the like.

[0206] In Fig. 5(A) further provides color layers (a red color layer 1034R, a green color layer 1034G, and a blue color layer 1034B) on a transparent base material 1033. Additionally, a black layer (black matrix) 1035 can be provided. The transparent base material 1033, which is provided with the color layers and the black layer, is positioned and attached to the substrate 1001. It should be noted that the color layers and the black layer are covered with a protective layer. Furthermore, Fig. 5(A) represents a light-emitting layer whose light is not transmitted to the outside via a color layer, and a light-emitting layer whose light is transmitted to the outside via a corresponding color layer. Since light that is not transmitted via a color layer is white, and light that is transmitted via a color layer is red, blue, or green, an image can be represented using pixels of the four colors.

[0207] Fig. Figure 5(B) provides an example in which the color layers (the red color layer 1034R, the green color layer 1034G, and the blue color layer 1034B) are formed between the gate insulating film 1003 and the first insulating intermediate film 1020. In this way, the color layers can be provided between the substrate 1001 and the sealing substrate 1031.

[0208] Furthermore, the light-emitting device described above is a light-emitting device with a structure in which light is extracted towards the side of the substrate 1001 above which the FETs are formed (bottom-emission type); however, a light-emitting device with a structure in which light is extracted towards the side of the sealing substrate 1031 (top-emission type) can also be used. Fig. Figure 6 shows a cross-sectional view of a top-emission light-emitting device. In this case, an opaque substrate can be used as substrate 1001. The fabrication is carried out in a similar manner to the bottom-emission light-emitting device until a connecting electrode is formed, through which the FET and the anode of the light-emitting element are connected. Then, a third insulating intermediate film 1037 is formed such that it covers an electrode 1022. This insulating film can have a flattening function. The third insulating intermediate film 1037 can be formed using a material similar to that of the second insulating intermediate film or using other different materials.

[0209] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting elements serve as anodes here, but they can also function as cathodes. Furthermore, the light-emitting device is of the top-emission type, as in Fig. 6. The first electrodes are preferably reflective electrodes. The EL layer 1028 has a structure similar to the structure of the EL layer 103 in Fig. 1(A) or the EL layer 503 in Fig. 1(B) is similar; an element structure is used in which a white light emission can be obtained.

[0210] With a top-emission structure like in Fig. 6. Sealing can be carried out using the sealing substrate 1031, on which the color layers (the red color layer 1034R, the green color layer 1034G, and the blue color layer 1034B) are provided. The sealing substrate 1031 can be provided with the black layer (black matrix) 1035, which is positioned between pixels. The color layers (the red color layer 1034R, the green color layer 1034G, and the blue color layer 1034B) and the black layer can be covered with a cover layer. It should be noted that a translucent substrate is used as the sealing substrate 1031.

[0211] Furthermore, no special restriction is imposed on the example shown here for a full-color display with four colors, namely red, green, blue and white; a full-color display with three colors, namely red, green and blue, or with four colors, namely red, green, blue and yellow, can also be carried out.

[0212] Fig. Figure 7 represents a light-emitting passive matrix device, which is an embodiment of the present invention. It should be noted that Fig. 7(A) a perspective view showing the light-emitting device is and Fig. 7(B) is a cross-sectional view obtained by cutting from Fig. 7(A) is obtained along XY. In Fig. In Figure 7, an EL layer 955 is provided between an electrode 952 and an electrode 956 above a substrate 951. An end section of the electrode 952 is covered with an insulating layer 953. Furthermore, a partition layer 954 is provided above the insulating layer 953. The side walls of the partition layer 954 are inclined such that the distance between one side wall and the other side wall decreases towards the surface of the substrate. This means that a cross-section in the direction of the short side of the partition layer 954 is trapezoidal and that the lower side (the side facing the direction corresponding to the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the upper side (the side facing the direction corresponding to the surface direction of the insulating layer 953 and not in contact with the insulating layer 953).The partition layer 954 provided in this way can prevent defects in the light-emitting element due to static electricity or the like.

[0213] In the light-emitting device described above, many very small light-emitting elements arranged in a matrix can be separately controlled by the FETs formed in the pixel section; consequently, the light-emitting device can be advantageously used as a display device that presents an image. < <beleuchtungsvorrichtung>>

[0214] A lighting device, which is an embodiment of the present invention, is described by means of Fig. 8 described. Fig. Figure 8(B) is a top view of the lighting device, and Fig. 8(A) is a cross-sectional view along ef in Fig. 8(B).

[0215] In the lighting device, a first electrode 401 is formed above a substrate 400, which serves as a support and is transmissive to light. The first electrode 401 corresponds to the anode 101 in Fig. 1(A) and Fig. 1(B). In the case where light is taken from the side of the first electrode 401, the first electrode 401 is formed using a material with light transmittance.

[0216] A pad 412 for supplying a voltage to a second electrode 404 is formed above the substrate 400.

[0217] An EL layer 403 is formed above the first electrode 401. The EL layer 403 corresponds to the EL layer 103 in Fig. 1(A) and Fig. 1(B), the EL layer 503, or the like. It should be noted that reference should be made to the corresponding description regarding their structures.

[0218] The second electrode 404 is configured to cover the EL layer 403. The second electrode 404 corresponds to the cathode 102 in Fig. 1(A). In the case where light is extracted from the side of the first electrode 401, the second electrode 404 is designed to contain a material with high reflectivity. The second electrode 404 is connected to the pad 412, thereby applying a voltage.

[0219] The first electrode 401, the EL layer 403, and the second electrode 404 form a light-emitting element. The light-emitting element and a sealing substrate 407 are joined together with sealants 405 and 406, thus completing the lighting device. Additionally, if a double sealant is formed, the inner sealant can be mixed with a desiccant, which adsorbs moisture and increases reliability.

[0220] Furthermore, if the pad 412 and the first electrode 401 are provided in such a way that they extend partially to the outside of the sealing materials 405 and 406, external input connections can be obtained. An IC chip 420 or the like, mounted with a converter or the like, can also be provided. <<Elektronisches Gerät> >

[0221] Examples of an electronic device that is an embodiment of the present invention are described. Examples of the electronic device include a television set (also called a TV or television receiver), a computer monitor or the like, a digital camera, a digital video camera, a digital photo frame, a mobile phone (also called a cell phone or mobile phone device), a portable game console, a portable information terminal, an audio playback device, and a large gaming machine, such as a pinball machine. Specific examples of these electronic devices are shown below.

[0222] Fig. Figure 9(A) represents an example of a television set. In this television set, a display section 7103 is installed in a housing 7101. The housing 7101 is also supported by a base 7105. Images can be displayed on the display section 7103, and light-emitting elements are arranged in a matrix within the display section 7103.

[0223] The television can be operated using a control switch on the housing 7101 or a separate remote control 7110. The remote control 7110's control buttons 7109 allow the television channels and volume to be adjusted, and images displayed on the screen 7103 can be controlled. Furthermore, the remote control 7110 can be equipped with a screen 7107 for displaying information output by the remote control 7110.

[0224] It should be noted that the television set is equipped with a receiver, a modem, and the like. The receiver can receive general television broadcasts. Furthermore, when connected wirelessly or via the modem to a communication network, unidirectional (from a sender to a receiver) or bidirectional (e.g., between a sender and a receiver or between receivers) data communication can take place.

[0225] Fig. Figure 9(B1) represents a computer comprising a main unit 7201, a case 7202, a display section 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. It should be noted that this computer is manufactured by arranging light-emitting elements in a matrix and using them for the display section 7203. The computer in Fig. 9(B1) can also be in a form like in Fig. 9(B2). The computer in Fig. 9(B2) is equipped with a second display section 7210 in place of the keyboard 7204 and the pointing device 7206. The second display section 7210 is a touchscreen, and input can be performed by controlling the input display shown on the second display section 7210 with a finger or an associated stylus. Furthermore, the second display section 7210 can also display images other than the input display. The display section 7203 can also be a touchscreen. Connecting the two screens by means of a hinge prevents problems such as the screens cracking or being damaged during storage or transport.

[0226] Fig. 9(C) and Fig. Figure 9(D) provides examples of a portable information terminal. The portable information terminal is equipped with a display section 7402, which is installed in a housing 7401, as well as control knobs 7403, an external connection port 7404, a loudspeaker 7405, a microphone 7406, and the like. It should be noted that the portable information terminal includes the display section 7402, which is produced by arranging light-emitting elements in a matrix.

[0227] The in Fig. 9(C) and Fig. The portable information terminals shown in Figure 9(D) may also have a structure in which information can be entered by touching the display section 7402 with a finger or the like. In this case, operations such as making a call and writing an email can be performed by touching the display section 7402 with a finger or the like.

[0228] The screen of display section 7402 has three main modes. The first is a display mode primarily for showing images. The second is an input mode primarily for entering information, such as text. The third is a display+input mode, in which the two modes, namely the display mode and the input mode, are combined.

[0229] For example, when making a call or writing an email, display section 7402 is switched to a text input mode primarily for entering text, allowing the text displayed on the screen to be entered. In this case, a keyboard or number keys are preferably displayed on almost the entire screen of display section 7402.

[0230] Furthermore, if a detection device incorporating a sensor for detecting inclination, such as a gyroscope sensor or an accelerometer, is provided within the portable information terminal, the display on the screen of display section 7402 can be automatically switched by determining the orientation of the portable information terminal (vertical or horizontal).

[0231] The screen modes are switched by touching the display section 7402 or by operating the control buttons 7403 on the housing 7401. Alternatively, the switching can be performed depending on the type of image displayed on the display section 7402. For example, if the signal of an image displayed on the display section is data from a moving image, the switch to display mode is performed. If it is text data, the switch to input mode is performed.

[0232] Furthermore, in the case where there is no input by touching the display section 7402 for a certain time in input mode, while a signal detected by an optical sensor in the display section 7402 is being detected, the screen mode can be controlled such that it switches from input mode to display mode.

[0233] The display section 7402 can also function as an image sensor. For example, when the display section 7402 is touched with a palm or finger, an image of the handprint, fingerprint, or the like is captured, enabling personal authentication. Furthermore, an image of a finger vein, palm vein, or the like can be captured by using a near-infrared backlight or a near-infrared scanning light source for the display section.

[0234] It should be noted that a combination of the structures described in this description may be appropriately used in the aforementioned electronic devices.

[0235] Furthermore, the light-emitting element of an embodiment of the present invention is preferably used for the display section. The light-emitting element can be one with high emission efficiency. Additionally, a light-emitting element with a low operating voltage can be obtained. Therefore, the electronic device incorporating the light-emitting element of an embodiment of the present invention can be a low-power electronic device.

[0236] Fig. Figure 10 presents an example of a liquid crystal display device in which a light-emitting element is used for backlighting. The in Fig. Figure 10 shows a liquid crystal display device comprising a housing 901, a liquid crystal layer 902, a backlight unit 903, and a housing 904. The liquid crystal layer 902 is connected to a driver IC 905. The light-emitting element is used for the backlight unit 903, which is supplied with current via a terminal 906.

[0237] Preferably, the light-emitting element of an embodiment of the present invention is used. By using the light-emitting element for the backlighting of the liquid crystal display device, a backlighting with reduced power consumption can be obtained.

[0238] Fig. Figure 11 represents an example of a table lamp that is an embodiment of the present invention. The Fig. Figure 11 shows a table lamp comprising a housing 2001 and a light source 2002, and a lighting device in which a light-emitting element is used is used as the light source 2002.

[0239] Fig. Figure 12 represents an example of an interior lighting device 3001. The light-emitting element of an embodiment of the present invention is preferably used for the lighting device 3001.

[0240] Fig. Figure 13 represents a car that is an embodiment of the present invention. In the car, light-emitting elements are mounted on a windshield and a dashboard. Display areas 5000 to 5005 are provided using light-emitting elements. Preferably, the light-emitting element of an embodiment of the present invention is used, which can reduce the power consumption of display areas 5000 to 5005, and it is therefore suitable for use in a car.

[0241] Display areas 5000 and 5001 are display devices installed in the car windshield, employing light-emitting elements. By using translucent electrodes as the first and second electrodes of these light-emitting elements, so-called transparent display devices, through which the opposite side can be seen, can be obtained. A transparent display can be provided without obstructing the view, even when mounted on the car windshield. It should be noted that if a driver transistor or the like is provided, a translucent transistor, such as an organic transistor containing an organic semiconductor material or a transistor using an oxide semiconductor, is preferably used.

[0242] Display area 5002 is a display device provided in a pillar section and uses a light-emitting element. Display area 5002 can compensate for the view obstructed by the pillar by displaying an image captured by an imaging device provided in the vehicle body. Furthermore, display area 5003, provided in a part of the instrument panel, can also compensate for the view obstructed by the vehicle body by displaying an image captured by an imaging device provided outside the vehicle. Therefore, blind spots can be eliminated to increase safety. By displaying images in such a way as to compensate for areas that are not visible, safety can be assessed more easily and without inconvenience.

[0243] Display areas 5004 and 5005 can provide various information, such as navigation information, a speedometer, a tachometer, an odometer, a fuel gauge, a gear shift indicator, and climate control settings. The content or layout of the display can be modified according to user preference. It should be noted that this information can also be displayed on display areas 5000 to 5003. Display areas 5000 to 5005 can also be used as illumination devices.

[0244] Fig. 14(A) and Fig. Figure 14(B) provides an example of a bifold tablet computer. Fig. Figure 14(A) represents an open state, and the tablet computer comprises a housing 9630, a display section 9631a, a display section 9631b, a switch 9034 for switching the display modes, a power switch 9035, a switch 9036 for switching to a power-saving mode, and a clasp 9033. It should be noted that the tablet computer is manufactured by using a light-emitting device, which includes the light-emitting element of an embodiment of the present invention, for the display section 9631a and / or the display section 9631b.

[0245] Part of the display section 9631a can serve as a touchscreen area 9632a, and data can be entered when a displayed control button 9637 is touched. It should be noted that the structure of the display section 9631a is not limited to the exemplary structure shown, where half the area has only a display function and the other half has a touchscreen function. A structure can also be used in which the entire area of ​​the display section 9631a has a touchscreen function. For example, the entire area of ​​the display section 9631a can display keyboard buttons to serve as a touchscreen, and the display section 9631b can be used as a display screen.

[0246] As with display section 9631a, a portion of display section 9631b can also serve as a touchscreen area 9632b. If the area where a button for switching the keyboard display 9639 is shown on the touchscreen is touched with a finger, a stylus, or the like, keyboard buttons can be displayed on display section 9631b.

[0247] Furthermore, touch input can be performed simultaneously on touchscreen area 9632a and touchscreen area 9632b.

[0248] Switch 9034, used to change display modes, allows the user to select different orientations, such as portrait, landscape, monochrome, or color. Switch 9036, used to activate power-saving mode, optimizes the display brightness according to the ambient light level, which is detected by an optical sensor integrated into the tablet computer. In addition to the optical sensor, the tablet computer may also incorporate another sensor, such as a tilt sensor (e.g., a gyroscope or accelerometer).

[0249] In the Fig. In the example shown in Figure 14(A), display section 9631a and display section 9631b have the same display area. Without being particularly restricted, the size of one of them may differ from the size of the other, and their display qualities may differ. For example, one of them may be a display screen suitable for high-resolution display compared to the other.

[0250] Fig. Figure 14(B) represents a folded state. In this embodiment, an example is shown in which the tablet computer includes the housing 9630, a solar cell 9633, a charge / discharge control circuit 9634, a battery 9635, and a DC-DC converter 9636. It should be noted that Fig. Figure 14(B) shows an exemplary structure in which the charge / discharge control circuit 9634 includes the battery 9635 and the DC voltage converter 9636.

[0251] It should be noted that, since the tablet computer can be folded in two stages, the housing 9630 can be folded when not in use. Therefore, the display section 9631a and the display section 9631b can be protected, resulting in a tablet computer that offers excellent durability and reliability for long-term use.

[0252] Additionally, the in Fig. 14(A) and Fig. 14(B) The tablet computers shown have a function for displaying various types of information (e.g., a still image, a moving image, and a text image), a function for displaying a calendar, date, time, or the like on the display section, a touch input function for operating or editing information displayed on the display section by touch input, a function for controlling processing by various types of software (programs), and the like.

[0253] The solar cell 9633, which is attached to a surface of the tablet computer, can supply energy to the touchscreen, the display section, an image signal processing section, or the like. It should be noted that the solar cell 9633 is preferably provided on one or two surfaces of the housing 9630, in which case the battery 9635 can be efficiently charged.

[0254] Furthermore, the structure and working methods of the in Fig. The charging / discharging control circuit 9634 shown in 14(B) is illustrated in a block diagram in Fig. 14(C) described. Fig. 14(C) represents the solar cell 9633, the battery 9635, the DC-DC converter 9636, a converter 9638, switches SW1 to SW3, and the display section 9631. The battery 9635, the DC-DC converter 9636, the converter 9638, and the switches SW1 to SW3 correspond to the one shown in Fig. 14(B) shown charging / discharging control circuit 9634.

[0255] First, an example of the operation is described in the case where energy is generated by solar cell 9633 using external light. The voltage of the energy generated by the solar cell is increased or decreased by DC-DC converter 9636 to provide a voltage for charging battery 9635. Subsequently, when the energy charged by solar cell 9633 is used to operate display section 9631, switch SW1 is turned on, and the voltage is increased or decreased by converter 9638 to a voltage required for display section 9631. Additionally, when no display is being performed on display section 9631, battery 9635 can be charged by turning off SW1 and turning on SW2.

[0256] It should be noted that although the solar cell 9633 is described as an example of a power source, there is no particular restriction regarding the power source and that the battery 9635 can also be charged by another power source, such as a piezoelectric element (piezoelectric element) or a thermoelectric converter element (Peltier element). Charging can also be carried out by a contactless power transfer module that wirelessly (contactlessly) transmits and receives energy, or by a combination with another charging device; the power source does not necessarily have to be provided.

[0257] Furthermore, the tablet computer is not compatible with the tablet computer with the in Fig. 14 limited to the form shown, as long as the preceding display section 9631 is provided.

[0258] Fig. 15(A) to Fig. 15(C) represent a foldable, portable information terminal 9310. Fig. Figure 15(A) shows the portable information terminal 9310 in an open position. Fig. Figure 15(B) shows the portable information terminal 9310 in a state in which it is changed from the unfolded state to a folded state or vice versa. Fig. Figure 15(C) depicts the 9310 portable information terminal in its folded state. The 9310 portable information terminal is highly portable when folded. When unfolded, the seamless large display area provides excellent searchability.

[0259] A display screen 9311 is supported by three housings 9315, which are connected to each other by hinges 9313. It should be noted that the display screen 9311 can be a touchscreen (an input / output device) on which a touch sensor (an input device) is mounted. Furthermore, the shape of the portable information terminal 9310 can be reversibly changed from the unfolded state to the folded state by folding the display screen 9311 at the hinges 9313 between two housings 9315. The light-emitting device of an embodiment of the present invention can be used for the display screen 9311. A display area 9312 of the display screen 9311 is a display area that is positioned on a side surface of the portable information terminal 9310 in the folded state.The display area 9312 can show information icons, shortcuts to frequently used applications or programs, and the like, and confirmation of information and starting an application can be carried out quickly and easily.

[0260] Furthermore, the organic compound of an embodiment of the present invention can be used for an electronic device, such as an organic thin-film solar cell. In particular, it exhibits charge carrier transport properties and can therefore be used for a charge carrier transport layer or a charge carrier injection layer. Additionally, a film in which it is mixed with an acceptor substance can be used as a charge generation layer. It can also be used for an energy generation layer, since it is excited by light. [Example 1](Synthesis Example 1)

[0261] This synthesis example describes in detail a method for synthesizing N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mMemFLPA2Nbf(IV)), which is represented as structural formula (102) in embodiment 1. The structural formula of 3,10mMemFLPA2Nbf(IV) is shown below. <Schritt 1: Synthese von 3,7-Bis(4-chlor-2-fluorphenyl)-2,6-dimethoxynaphthalen>

[0262] Into a 500 mL three-necked flask, 11 g (24 mmol) of 3,7-diiodo-2,6-dimethoxynaphthalene, 14 g (78 mmol) of 4-chloro-2-fluorophenylboronic acid, 22 g (0.16 mol) of potassium carbonate, and 0.74 g (2.4 mmol) of tris(2-methylphenyl)phosphine were added. 120 mL of toluene were added to this mixture. While the pressure was reduced, the mixture was stirred to degas. 0.11 g (0.49 mmol) of palladium(II) acetate was added to this mixture, and stirring was carried out for 50.5 hours under a nitrogen stream at 110°C.

[0263] After stirring, toluene was added to this mixture, and suction filtration was performed over Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135), Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-16855), and aluminum oxide to obtain a filtrate. The filtrate was concentrated to obtain a solid.

[0264] The resulting solid was purified by silica gel column chromatography (eluent: toluene:hexane = 1:1). The resulting solid was recrystallized from ethyl acetate to yield 5.7 g of a white solid in a 53% yield. The synthesis scheme for step 1 is shown below.

[0265] Fig. 16 shows 1 H-NMR data of the obtained solid, the numerical data of which are shown below. 1 H NMR (CDCl3, 300 MHz): δ = 3.88 (s, 6H), 7.18-7.24 (m, 6H), 7.37 (t, J1 = 7.2 Hz, 2H), 7.65 (s, 2H). <Schritt 2: Synthese von 3,7-Bis(4-chlor-2-fluorphenyl)-2,6-dihydroxynaphthalen>

[0266] 5.7 g (13 mmol) of 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dimethoxynaphthalene were placed in a 200 mL three-necked flask, and the air in the flask was replaced with nitrogen. 32 mL of dichloromethane were added to this flask. 28 mL (28 mmol) of boron tribromide (approximately 1.0 mol / L of a dichloromethane solution) and 20 mL of dichloromethane were added dropwise to this solution. After the dropwise addition, the solution was stirred at room temperature.

[0267] After stirring, approximately 20 ml of water were added to this solution while cooling with ice, and stirring was performed. After stirring, an organic layer and an aqueous layer were separated, and the aqueous layer was subjected to extraction with dichloromethane and ethyl acetate. The extraction solution and the organic layer were combined and washed with a saturated salt solution and a saturated aqueous sodium bicarbonate solution. Moisture in the organic layer was adsorbed by magnesium sulfate, and after drying, this mixture was subjected to gravity filtration. The resulting filtrate was concentrated to obtain 5.4 g of a white solid. The synthesis scheme of step 2 is shown below.

[0268] Fig. 17 shows 1 H-NMR data of the obtained solid, the numerical data of which are shown below. 1 H-NMR (DMSO-d6, 300 MHz): δ = 7,20 (s, 2H), 7,37 (dd, J1 = 8,4 Hz, J2 = 1,8 Hz, 2H), 7,46-7,52 (m, 4H), 7,59 (s, 2H), 9,71 (s, 2H). <Schritt 3: Synthese von 3,10-Dichlornaphtho[2,3-b;6,7-b']bisbenzofuran>

[0269] In a 200 mL three-necked flask, 5.4 g (13 mmol) of 3,7-bis(4-chloro-2-fluorophenyl)-2,6-dihydroxynaphthalene and 7.1 g (52 mmol) of potassium carbonate were added. 130 mL of N-methyl-2-pyrrolidone were added to this mixture, and the mixture was stirred to degas while the pressure was reduced. After degassing, the mixture was stirred under a stream of nitrogen at 120 °C for 7 hours. After stirring, water was added to the mixture, and a precipitated solid was collected by filtration. This solid was washed with water and ethanol. Ethanol was added to the resulting solid; after heating and stirring, filtration was carried out to obtain a final solid. Ethyl acetate was added to the final solid. After heating and stirring, filtration was carried out, yielding 4.5 g of a pale yellow solid in a yield of 92%. The synthesis scheme for step 3 is shown below.

[0270] Fig. 18 shows 1 H-NMR data of the obtained solid, the numerical data of which are shown below. 1 H NMR (1,1,2,2-tetrachloroethane-D2, 300 MHz): δ = 7.44 (dd, J1 = 8.1 Hz, J2 = 1.5 Hz, 2H), 7.65 (d, J1 = 1.8 Hz, 2H), 8.05 (d, J1 = 8.4 Hz, 2H), 8.14 (s, 2H), 8.52 (s, 2H). <Schritt 4: Synthese von N,N'-Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamin (Abkürzung: 3,10mMemFLPA2Nbf(IV))>

[0271] Into a 200 mL three-necked flask, 0.82 g (2.2 mmol) of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran, 2.8 g (6.5 mmol) of N-(3-methylphenyl)-3-(9-phenyl-9H-fluoren-9-yl)phenylamine, 78 mg (0.22 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.3 g (13 mmol) of sodium tert-butoxide were added. 25 mL of xylene were added to this mixture. While the pressure was reduced, the mixture was stirred to degas. 25 mg (43 µmol) of bis(dibenzylideneacetone)palladium(0) were added to this mixture, and stirring was carried out for 9.5 hours under a nitrogen stream at 150 °C.

[0272] After stirring, toluene was added to this mixture, and suction filtration over Florisil, Celite, and aluminum oxide was performed to obtain a filtrate. The filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (eluent: toluene). The resulting solid was reprecipitated from toluene / ethyl acetate, and a solid was collected. The resulting solid was recrystallized twice from toluene, yielding 1.3 g of a yellow solid in 50% yield.

[0273] 1.1 g of the obtained solid were purified by sublimation using a train sublimation process. The sample was heated at 390 °C under conditions where the pressure was 1.1 × 10 -2 The Pa value was 0 ml / min and the argon flow rate was 0 ml / min. After sublimation purification, 0.52 g of a yellow solid was obtained with a recovery rate of 42%. The synthesis scheme for step 4 is shown below.

[0274] Fig. 19 shows 1 ¹H NMR data of the obtained solid, the numerical data of which are shown below, were obtained from these data. It was determined that 3.10 mMemFLPA2Nbf(IV), which is the organic compound of an embodiment of the present invention, was obtained in this synthesis example. 1 H-NMR (1,1,2,2-tetrachloroethane-D2, 300 MHz): δ = 2.30 (s, 6H), 6.74 (d, J1 = 7.8 Hz, 2H), 6.90-7.00 (m, 8H), 7.05-7.32 (m, 24H), 7.36-7.41 (m, 8H), 7.76-7.79 (m, 4H), 7.85 (d, J1 = 8.1 Hz, 2H), 8.02 (s, 2H), 8.37 (s, 2H).

[0275] Next, we will show Fig. 20 the measurement results of the absorption spectrum and the emission spectrum of 3.10mMemFLPA2Nbf(IV) in a toluene solution. Fig. Figure 21 shows the absorption and emission spectra of a thin film. The solid, thin film was formed by vacuum evaporation over a quartz substrate. The absorption spectrum of the toluene solution was measured with a UV-VIS spectrophotometer (V550, manufactured by JASCO Corporation) and is shown as the spectrum from which a spectrum measured on toluene alone in a quartz cell has been subtracted. The absorption spectrum of the thin film was measured with a spectrophotometer (U-4100 spectrophotometer, manufactured by Hitachi High-Technologies Corporation). The emission spectrum of the thin film was measured with a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). The emission spectrum in solution and the quantum yield were measured with an absolute PL quantum yield measurement system (Quantaurus-QY, manufactured by Hamamatsu Photonics KK).

[0276] As in Fig. As shown in Figure 20, 3.10 mMemFLPA2Nbf(IV) in toluene solution exhibits absorption peaks at approximately 425 nm, 402 nm, 309 nm, 297 nm, and 282 nm, as well as emission wavelength peaks at approximately 439 nm and 466 nm (excitation wavelength: 400 nm). As shown in Fig. As shown in Figure 21, the thin film of 3.10 mMemFLPA2Nbf(IV) exhibits absorption peaks at approximately 428 nm, 406 nm, 307 nm, 275 nm, and 262 nm, as well as emission wavelength peaks at approximately 454 nm and 482 nm (excitation wavelength: 410 nm). From these results, it was determined that 3.10 mMemFLPA2Nbf(IV) emits blue light and can be used as a host for a light-emitting substance or a substance that emits fluorescence in the visible range.

[0277] Furthermore, the measured quantum yield in the toluene solution was very high, namely 93%, which suggests suitability as a light-emitting material.

[0278] Next, 3.10mMemFLPA2Nbf(IV) obtained in this example was analyzed by liquid chromatography coupled with mass spectrometry (LC / MS).

[0279] For LC / MS, LC (liquid chromatographic) separation was performed using Ultimate 3000, manufactured by Thermo Fisher Scientific KK, and MS (mass spectrometry) was performed using Q Exactive, manufactured by Thermo Fisher Scientific KK.

[0280] For the LC separation, a given column was used, with the column temperature set to 40 °C, and the solution was introduced under the following conditions: A solvent was appropriately selected, the sample was adapted by dissolving 3.10 mMemFLPA2Nbf(IV) at a given concentration in an organic solvent, and the injection volume was 5.0 µl.

[0281] Through a targeted MS 2 -Procedure was an MS 2 - Measurement of a component with m / z = 1150.45, corresponding to an ion originating from 3.10 mMemFLPA2Nbf(IV). The settings of the Targeted-MS 2 The parameters are as follows: The mass range of the targeting element was set to m / z = 1150.45 ± 2.0 (isolation window = 4), and it was acquired in a positive mode. During the measurement, the normalized collision energy (NCE) for accelerating the targeting element in a collision cell was set to 50. Fig. Figure 22 shows the obtained MS spectrum.

[0282] From the results in Fig. 22. It was found that productions of 3.10 mMemFLPA2Nbf(IV) are mainly recorded at m / z = approximately 1060, 910, 834, 729, 487 and 241. It should be noted that the in Fig. The results shown in Figure 22 are characteristic results derived from 3.10mMemFLPA2Nbf(IV); therefore, they can be considered important data for identifying 3.10mMemFLPA2Nbf(IV) contained in a mixture.

[0283] It should be noted that the production with m / z = approximately 1060 is presumably a cation in a state where a 3-methylphenyl group has been eliminated from 3.10 mMemFLPA2Nbf(IV), indicating that 3.10 mMemFLPA2Nbf(IV) contains a 3-methylphenyl group. The production with m / z = approximately 834 is presumably a cation in a state where a 3-(9-phenyl-9H-fluoren-9-yl)phenyl group has been eliminated from 3.10 mMemFLPA2Nbf(IV), indicating that 3.10 mMemFLPA2Nbf(IV) contains a 3-(9-phenyl-9H-fluoren-9-yl)phenyl group.

[0284] Furthermore, the production with m / z = approximately 729 is presumably a cation in a state in which an N-(3-methylphenyl)-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]amino group has been eliminated from 3.10mMemFLPA2Nbf(IV), which suggests that 3.10mMemFLPA2Nbf(IV) contains an N-(3-methylphenyl)-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]amino group. [Example 2]

[0285] In this example, a light-emitting element 1, which is a light-emitting element of an embodiment of the present invention described in the embodiments, and a light-emitting comparison element 1, which is a light-emitting element of a comparison example, are described in detail. The structural formulas of organic compounds used for the light-emitting element 1 and the light-emitting comparison element 1 are shown below. (Manufacturing process of the light-emitting element 1)

[0286] First, indium tin oxide containing silicon oxide (ITSO) was deposited onto a glass substrate by sputtering to form anode 101. It should be noted that the thickness was 70 nm and the electrode area was 4 mm². 2 (2 mm × 2 mm).

[0287] Next, as a pretreatment to form a light-emitting element above the substrate, a surface of the substrate was washed with water and baked at 200 °C for one hour, and then a UV ozone treatment was carried out for 370 seconds.

[0288] The substrate was then transferred to a vacuum evaporation unit, where the pressure was increased to approximately 10 -4 After the Pa was reduced, vacuum baking was carried out for 30 minutes at 170 °C in a heating chamber of the vacuum evaporation device, and then the substrate was cooled for approximately 30 minutes.

[0289] Next, the substrate on which the anode 101 was formed was attached to a substrate holder provided in the vacuum evaporation apparatus such that the surface on which the anode 101 was formed was facing downwards, and 3-[4-(9-Phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), represented by the above structural formula (i), and molybdenum(VI) oxide in a weight ratio of 4:2 (= PCPPn:molybdenum oxide) were deposited by co-evaporation using an evaporation process employing resistance heating to a thickness of 10 nm over the anode 101, thereby forming the hole injection layer 111.

[0290] Next, PCPPn was vapor-deposited onto the hole injection layer 111 in a thickness of 30 nm, thereby forming the hole transport layer 112.

[0291] Subsequently, 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), represented by the above structural formula (ii), and N,N'-Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mMemFLPA2Nbf(IV)), represented by the above structural formula (iii), were deposited in a weight ratio of 1:0.03 (= cgDBCzPA: 3,10mMemFLPA2Nbf(IV)) by co-evaporation to a thickness of 25 nm, forming the light-emitting layer 113.

[0292] Subsequently, cgDBCzPA was deposited onto the light-emitting layer 113 in a thickness of 15 nm, and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), represented by the above structural formula (iv), was deposited onto it in a thickness of 10 nm, thereby forming the electron transport layer 114.

[0293] After forming the electron transport layer 114, lithium fluoride (LiF) was deposited to a thickness of 1 nm, forming the electron injection layer 115, and subsequently aluminum was deposited to a thickness of 200 nm, forming the cathode 102. In this way, the light-emitting element 1 was produced. (Manufacturing process of the light-emitting reference element 1)

[0294] The light-emitting reference element 1 was prepared as follows: The light-emitting layer 113 was formed using 3,10-bis(diphenylamino)naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10DPhA2Nbf(IV)), represented by the above structural formula (v), instead of 3,10mMemFLPA2Nbf(IV), which had been used for the light-emitting layer 113 of the light-emitting element 1, and the electron transport layer 114 was formed using bathophenanthroline (abbreviation: BPhen), represented by the above structural formula (vi), instead of NBPhen, which had been used for the electron transport layer 114 of the light-emitting element 1. 3,10DPhA2Nbf(IV), which was used for the light-emitting reference element 1, and 3,10mMemFLPA2Nbf(IV), which was used for the light-emitting element 1, are substances that have the same basic structure, i.e.Naphthobisbenzofuran, but differ from each other in the structure of the amine bound to it.

[0295] The element structures of light-emitting element 1 and light-emitting comparison element 1 are summarized in the following table. [Table 1] Lochinjektionsschicht Lochtransportschicht Licht emittierende Schicht Elektronentransportschicht Elektroneninjektionsschicht 10 nm 30 nm 25 nm 15 nm 10 nm 1 nm Licht emittierendesElement 1 PCPPn:MoOx(4:2) PCPPn cgDBCzPA:3,10mMemFLPA2Nbf(IV)(1:0,03) -cgDBCzPA NBPhen LiF Licht emittierendesVergleichselement1 cgDBCzPA:3,10DPhA2Nbf(IV)(1:0,03) BPhen

[0296] Light-emitting element 1 and light-emitting reference element 1 were each sealed with glass substrates in a glove box containing a nitrogen atmosphere, such that the light-emitting element was not exposed to air (a sealant was applied around the element, and UV treatment and a one-hour heat treatment at 80 °C were performed during sealing). The initial properties of these light-emitting elements were then measured. It should be noted that the measurement was carried out at room temperature (in an atmosphere maintained at 25 °C).

[0297] Fig. Figure 23 shows the luminance-current density properties of light-emitting element 1 and light-emitting comparison element 1. Fig. Figure 24 shows its power efficiency-luminance properties. Fig. Figure 25 shows its luminance-voltage properties. Fig. Figure 26 shows its current-voltage properties. Fig. Figure 27 shows its external quantum efficiency luminance properties. Fig. Figure 28 shows their emission spectra. Furthermore, their elemental properties are shown at a luminance of approximately 1000 cd / m². 2 summarized in Table 2. [Table 2] Spannung(V) Strom(mA) Current density (mA / cm³) 2 ) Chromatizitätx Chromatizitäty Stromeffizienz (cd / A) external quantum efficiency (%) Light-emitting element 1 3,2 0,49 12,3 0,14 0,08 8,4 10,7 Light-emitting reference element 1 3,2 0,66 16,6 0,14 0,11 6,5 6,8

[0298] In Fig. 23 to Fig. Figure 28 and Table 2 show that the light-emitting element 1 achieves very good results, namely an external quantum efficiency of 1000 cd / m². 2 of 10.7%. Furthermore, it was found that light-emitting element 1 is a light-emitting element with a higher efficiency than light-emitting reference element 1. Moreover, its chromaticity exhibits a smaller peak on the long wavelength side and a narrower spectrum than light-emitting reference element 1, indicating that it emits excellent blue light.

[0299] A light-emitting element with the same structure as light-emitting element 1 was subjected to operational tests. Fig. Figure 47 shows a diagram illustrating the change in luminance as a function of operating time under the following conditions: The current was 2 mA, and the current density was constant. As in Fig. As shown in Figure 47, it was found that the light-emitting element with the structure is a long-life light-emitting element.

[0300] This means that it has been found that 3.10mMemFLPA2Nbf(IV), which is an embodiment of the present invention, is suitable for a blue light emitting material with high emission efficiency, high color purity and high reliability. [Example 3]

[0301] In this example, a light-emitting element 2, which is a light-emitting element of an embodiment of the present invention as described in the embodiments, is described in detail. The structural formulas of organic compounds used for the light-emitting element 2 are shown below. (Manufacturing process of the light-emitting element 2)

[0302] First, indium tin oxide containing silicon oxide (ITSO) was deposited onto a glass substrate by sputtering to form anode 101. It should be noted that the thickness was 70 nm and the electrode area was 4 mm². 2 (2 mm × 2 mm).

[0303] Next, as a pretreatment to form a light-emitting element above the substrate, a surface of the substrate was washed with water and baked at 200 °C for one hour, and then a UV ozone treatment was carried out for 370 seconds.

[0304] The substrate was then transferred to a vacuum evaporation unit, where the pressure was increased to approximately 10 -4 After the Pa was reduced, vacuum baking was carried out for 30 minutes at 170 °C in a heating chamber of the vacuum evaporation device, and then the substrate was cooled for approximately 30 minutes.

[0305] Next, the substrate on which the anode 101 was formed was attached to a substrate holder provided in the vacuum evaporation apparatus such that the surface on which the anode 101 was formed was facing downwards, and 3-[4-(9-Phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), represented by the above structural formula (i), and molybdenum(VI) oxide in a weight ratio of 4:2 (= PCPPn:molybdenum oxide) were deposited by co-evaporation using an evaporation process employing resistance heating to a thickness of 10 nm over the anode 101, thereby forming the hole injection layer 111.

[0306] Next, 3-[4-(9-Phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), represented by the above structural formula (i), was vapor-deposited to a thickness of 30 nm onto the hole injection layer 111, thereby forming the hole transport layer 112.

[0307] Subsequently, 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), represented by the above structural formula (ii), and N,N'-Bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mMemFLPA2Nbf(IV)), represented by the above structural formula (iii), were deposited in a weight ratio of 1:0.03 (= cgDBCzPA: 3,10mMemFLPA2Nbf(IV)) by co-evaporation to a thickness of 25 nm, forming the light-emitting layer 113.

[0308] Subsequently, 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), represented by the above structural formula (viii), was evaporated onto the light-emitting layer 113 in a thickness of 15 nm, and 2,9-Bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), represented by the above structural formula (iv), was evaporated onto it in a thickness of 10 nm, thereby forming the electron transport layer 114.

[0309] After forming the electron transport layer 114, lithium fluoride (LiF) was deposited to a thickness of 1 nm, forming the electron injection layer 115, and subsequently aluminum was deposited to a thickness of 200 nm, forming the cathode 102. In this way, the light-emitting element 2 of this example was produced.

[0310] The element structure of the light-emitting element 2 is summarized in the following table. [Table 3] Hole injection layer Hole transport layer light-emitting layer electron transport layer Electron injection layer 10 nm 30 nm 25 nm 15 nm 10 nm 1 nm Light-emitting element 2 PCPPn:MoOx(4:2) PCPPn cgDBCzPA:3.10mMemFLPA2Nbf(IV)(1:0.03) 2mDBTBPDBq-II NB Phen LiF

[0311] Light-emitting element 2 was sealed with glass substrates in a glove box containing a nitrogen atmosphere, such that the light-emitting element was not exposed to air (a sealant was applied around the element, and UV treatment and a one-hour heat treatment at 80 °C were performed during sealing). The initial properties of this light-emitting element were then measured. It should be noted that the measurement was carried out at room temperature (in an atmosphere maintained at 25 °C).

[0312] Fig. Figure 29 shows the luminance-current density properties of the light-emitting element 2. Fig. Figure 30 shows its power efficiency-luminance properties. Fig. Figure 31 shows its luminance-voltage properties. Fig. Figure 32 shows its current-voltage properties. Fig. Figure 33 shows their xy chromaticity coordinates. Fig. Figure 34 shows its external quantum efficiency luminance properties. Fig. Figure 35 shows their emission spectra. Furthermore, their elemental properties are shown at a luminance of approximately 1000 cd / m². 2 summarized in Table 4. [Table 4] Voltage (V) Current (mA) Current density (mA / cm³) 2 ) Chromaticityx Chromaticity Power efficiency (cd / A) external quantum efficiency (%) Light-emitting element 2 3,2 0,37 9,3 0,14 0,08 8,2 11,3

[0313] Out of Fig. 29 to Fig. 35 and Table 4 showed that the light-emitting element 2 is a light-emitting element that has excellent properties, namely an external quantum efficiency of 1000 cd / m². 2 of 11.3%. Furthermore, it was determined that light-emitting element 2 is an element that emits light with high efficiency. In addition, it was found that its chromaticity exhibits excellent blue light emission. [Example 4](Synthesis Example 2)

[0314] This synthesis example describes in detail a procedure for the synthesis of N,N'-diphenyl-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b,6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mFLPA2Nbf(IV)). The structural formula of 3,10mFLPA2Nbf(IV) is shown below. <Schritt 1: Synthese von 3,7-Bis(4-chlor-2-fluorphenyl)-2,6-dimethoxynaphthalen>

[0315] The synthesis was carried out in a similar manner to step 1 of synthesis example 1 in Example 1. <Schritt 2: Synthese von 3,7-Bis(4-chlor-2-fluorphenyl)-2,6-dihydroxynaphthalen>

[0316] The synthesis was carried out in a similar manner to step 2 of synthesis example 1 in Example 1. <Schritt 3: Synthese von 3,10-Dichlornaphtho[2,3-b;6,7-b']bisbenzofuran>

[0317] The synthesis was carried out in a similar manner to step 3 of synthesis example 1 in Example 1. <Schritt 4: Synthese von 3,10mFLPA2Nbf(IV)>

[0318] Into a 200 mL three-necked flask, 0.84 g (2.2 mmol) of 3,10-dichloronaphtho[2,3-b;6,7-b']bisbenzofuran, 2.7 g (6.7 mmol) of 3-(9-phenyl-9H-fluoren-9-yl)diphenylamine, 80 mg (0.22 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.3 g (13 mmol) of sodium tert-butoxide were added. 25 mL of xylene were added to this mixture. While the pressure was reduced, the mixture was stirred to degas. 26 mg (45 µmol) of bis(dibenzylideneacetone)palladium(0) were added to this mixture, and stirring was carried out for 7 hours under a nitrogen stream at 150 °C.

[0319] After stirring, toluene was added to this mixture, and suction filtration over Florisil, Celite, and aluminum oxide was carried out to obtain a filtrate. The filtrate was concentrated to obtain a solid. This solid was purified by silica gel column chromatography (silica gel, mobile phase: hexane:toluene = 2:1) to obtain a solid. The resulting solid was recrystallized three times from toluene, yielding 2.2 g of a yellow solid in 87% yield.

[0320] 1.2 g of the obtained solid were purified by sublimation using a train sublimation process. This involved heating at 385 °C under conditions where the pressure was 1.8 × 10 -2 Pa was and the argon flow rate was 0 ml / min. After sublimation purification, 1 g of a yellow solid was obtained with a recovery rate of 88%. The synthesis scheme of step 4 is shown below.

[0321] Fig. 36 shows 1 ¹H NMR data of the obtained solid, the numerical data of which are shown below. It should be noted that Fig. 36(B) is a diagram showing an enlarged portion of the range from 6.5 ppm to 8.5 ppm in Fig. Figure 36(A) shows. From these, it was determined that 3.10mFLPA2Nbf(IV), which is the organic compound of an embodiment of the present invention, was obtained in this synthesis example. 1 H NMR (1,1,2,2-tetrachloroethane-D2, 300 MHz): δ =6.76 (d, J1 = 8.1 Hz, 2H), 6.98-7.33 (m, 32H), 7.36-7.40 (m, 8H), 7.76-7.79 (m, 4H), 7.85 (d, J1 = 8.4 Hz, 2H), 8.02 (s, 2H), 8.38 (s, 2H).

[0322] Next, we will show Fig. 37 the measurement results of the absorption spectrum and the emission spectrum of 3.10mFLPA2Nbf(IV) in a toluene solution, and Fig. Figure 38 shows the absorption and emission spectra of a thin film of toluene solution. The solid thin film was formed by vacuum evaporation over a quartz substrate. The absorption spectrum of the toluene solution was measured with a UV-VIS spectrophotometer (V550, manufactured by JASCO Corporation) and is shown as the spectrum from which a spectrum measured on toluene alone in a quartz cell has been subtracted. The absorption spectrum of the thin film was measured with a spectrophotometer (U-4100 spectrophotometer, manufactured by Hitachi High-Technologies Corporation). The emission spectrum of the thin film was measured with a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). The emission spectrum in the toluene solution and the quantum yield were measured with an absolute PL quantum yield measurement system (Quantaurus-QY, manufactured by Hamamatsu Photonics KK).

[0323] In Fig. 37 exhibits 3.10 mFLPA2Nbf(IV) in toluene solution absorption peaks at 424 nm, 401 nm, 308 nm and 282 nm and emission wavelength peaks at 437 nm and 464 nm (excitation wavelength: 410 nm). Fig. 38 further shows that the thin film of 3.10 mFLPA2Nbf(IV) exhibits absorption peaks at 427 nm, 406 nm, 308 nm, 278 nm and 260 nm, as well as emission wavelength peaks at 453 nm and 480 nm (excitation wavelength: 400 nm). From these results, it was determined that 3.10 mFLPA2Nbf(IV) emits blue light and can be used as a host for a light-emitting substance or a substance that emits fluorescence in the visible range.

[0324] Furthermore, the measured quantum yield in the toluene solution was very high, namely 96%, which suggests suitability as a light-emitting material.

[0325] Next, 3.10mFLPA2Nbf(IV) obtained in this example was analyzed by liquid chromatography coupled with mass spectrometry (LC / MS).

[0326] For LC / MS, liquid chromatography (LC) separation was performed using Ultimate 3000, manufactured by Thermo Fisher Scientific KK, and mass spectrometry (MS) was performed using Q Exactive, manufactured by Thermo Fisher Scientific KK.

[0327] For the LC separation, a given column was used, with the column temperature set to 40 °C, and the solution was introduced under the following conditions: A solvent was appropriately selected, the sample was adapted by dissolving 3.10 mFLPA2Nbf(IV) at a given concentration in an organic solvent, and the injection volume was 5.0 µl.

[0328] Through a targeted MS 2 -Procedure was an MS 2 - Measurement of a component with m / z = 1122.42, corresponding to an ion originating from 3.10 mFLPA2Nbf(IV). The settings of the Targeted-MS 2 The parameters are as follows: The mass range of the targeting element was set to m / z = 1122.42 ± 2.0 (isolation window = 4), and it was acquired in a positive mode. During the measurement, the normalized collision energy (NCE) for accelerating the targeting element in a collision cell was set to 50. Fig. Figure 39 shows the obtained MS spectrum.

[0329] From the results in Fig. 39. It was determined that in the case where NCE is 50, productions of 3.10mFLPA2Nbf(IV) are mainly recorded at m / z = approximately 1046, 989, 882, 806, 715, 640, 564, 473, 397, 317 and 241. It should be noted that the in Fig. The results shown in Figure 39 are characteristic results derived from 3.10mFLPA2Nbf(IV); therefore, they are important data for identifying 3.10mFLPA2Nbf(IV) contained in a mixture.

[0330] It should be noted that the production with m / z = approximately 1046 is presumably a cation in a state where a phenyl group has been eliminated from 3.10mFLPA2Nbf(IV), indicating that 3.10mFLPA2Nbf(IV) contains a phenyl group. The production with m / z = approximately 882 is presumably a cation in a state where a 9-phenylfluorenyl group has been eliminated from 3.10mFLPA2Nbf(IV), indicating that 3.10mFLPA2Nbf(IV) contains a 9-phenylfluorenyl group.

[0331] Furthermore, the production with m / z = approximately 806 is presumably a cation in a state in which a 3-(9-phenyl-9H-fluoren-9-yl)phenyl group has been eliminated from 3,10mFLPA2Nbf(IV), which suggests that 3,10mFLPA2Nbf(IV) contains a 3-(9-phenyl-9H-fluoren-9-yl)phenyl group.

[0332] The production with m / z = approximately 715 is presumably a cation in a state in which a 3-(9-phenyl-9H-fluoren-9-yl)diphenylamino group has been eliminated from 3,10mFLPA2Nbf(IV), which suggests that 3,10mFLPA2Nbf(IV) contains a 3-(9-phenyl-9H-fluoren-9-yl)diphenylamino group.

[0333] The production with m / z = approximately 640 is presumably a cation in a state in which two 9-phenylfluorenyl groups have been eliminated from 3.10mFLPA2Nbf(IV), which suggests that 3.10mFLPA2Nbf(IV) contains two 9-phenylfluorenyl groups. [Example 5]

[0334] In this example, a light-emitting element 3, which is a light-emitting element of an embodiment of the present invention described in the embodiments, is described in detail. The structural formulas of organic compounds used for the light-emitting element 3 are shown below. (Manufacturing process of the light-emitting element 3)

[0335] First, indium tin oxide containing silicon oxide (ITSO) was deposited onto a glass substrate by sputtering to form anode 101. It should be noted that the thickness was 70 nm and the electrode area was 4 mm². 2 (2 mm × 2 mm).

[0336] Next, as a pretreatment to form a light-emitting element above the substrate, a surface of the substrate was washed with water and baked at 200 °C for one hour, and then a UV ozone treatment was carried out for 370 seconds.

[0337] The substrate was then transferred to a vacuum evaporation unit, where the pressure was increased to approximately 10 -4 After the Pa was reduced, vacuum baking was carried out for 30 minutes at 170 °C in a heating chamber of the vacuum evaporation device, and then the substrate was cooled for approximately 30 minutes.

[0338] Next, the substrate on which the anode 101 was formed was attached to a substrate holder provided in the vacuum evaporation apparatus such that the surface on which the anode 101 was formed was facing downwards, and 3-[4-(9-Phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), represented by the above structural formula (i), and molybdenum(VI) oxide in a weight ratio of 4:2 (= PCPPn:molybdenum oxide) were deposited by co-evaporation using an evaporation process employing resistance heating to a thickness of 10 nm over the anode 101, thereby forming the hole injection layer 111.

[0339] Next, PCPPn was vapor-deposited onto the hole injection layer 111 in a thickness of 30 nm, thereby forming the hole transport layer 112.

[0340] Subsequently, 7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), represented by the above structural formula (ii), and N,N'-Diphenyl-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mFLPA2Nbf(IV)), represented by the above structural formula (ix), were deposited in a weight ratio of 1:0.03 (= cgDBCzPA: 3,10mFLPA2Nbf(IV)) by co-evaporation to a thickness of 25 nm, forming the light-emitting layer 113.

[0341] Subsequently, cgDBCzPA was deposited onto the light-emitting layer 113 in a thickness of 15 nm, and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), represented by the above structural formula (iv), was deposited onto it in a thickness of 10 nm, thereby forming the electron transport layer 114.

[0342] After forming the electron transport layer 114, lithium fluoride (LiF) was deposited to a thickness of 1 nm, forming the electron injection layer 115, and subsequently aluminum was deposited to a thickness of 200 nm, forming the cathode 102. In this way, the light-emitting element 3 was produced.

[0343] The elemental structure of the light-emitting element 3 is summarized in the following table. [Table 5] Hole injection layer Hole transport layer light-emitting layer Electronic transport Electron injection layer 10 nm 30 nm 25 nm 15nm 10 nm 1 nm Light-emitting element 3 PCPPn:MoOx(4:2) PCPPn cgDBCzPA:3.10mFLPA2Nbf(IV)(1:0.03) cgDBCzPA NB Phen LiF

[0344] Light-emitting element 3 was sealed with glass substrates in a glove box containing a nitrogen atmosphere, such that the light-emitting element was not exposed to air (a sealant was applied around the element, and UV treatment and a one-hour heat treatment at 80 °C were performed during sealing). The initial properties of this light-emitting element were then measured. It should be noted that the measurement was carried out at room temperature (in an atmosphere maintained at 25 °C).

[0345] Fig. Figure 40 shows the luminance-current density properties of the light-emitting element 3. Fig. Figure 41 shows its power efficiency-luminance properties. Fig. Figure 42 shows its luminance-voltage properties. Fig. Figure 43 shows its current-voltage properties. Fig. Figure 44 shows its external quantum efficiency luminance properties. Fig. Figure 45 shows their emission spectra. Furthermore, their elemental properties are shown at a luminance of approximately 1000 cd / m². 2 summarized in Table 6. [Table 6] Voltage (V) Current (mA) Current density (mA / cm³) 2 ) Chromaticityx Chromaticity Power efficiency (cd / A) external quantum efficiency (%) Light-emitting element 3 3,2 0,48 12,1 0,14 0,09 8,1 9,8

[0346] In Fig. 40 to Fig. Figure 44 and Table 6 show that the light-emitting element 3 achieves very good results, namely an external quantum efficiency of 1000 cd / m². 2 of 9.8%. Furthermore, its chromaticity exhibits a small peak on the long wavelength side and a narrow half-width of the spectrum, indicating that it emits excellent blue light.

[0347] Light-emitting element 3 was subjected to operational tests. Fig. Figure 46 shows a diagram illustrating the change in luminance as a function of operating time under the following conditions: The current was 2 mA, and the current density was constant. As in Fig. As shown in Figure 46, the light-emitting element 3 retains 85% or more of its initial luminance even after 100 hours, indicating that it is a long-life light-emitting element.

[0348] This means that it was found that 3.10mFLPA2Nbf(IV), which is an embodiment of the present invention, is suitable for a blue light emitting material with high emission efficiency, high color purity and high reliability. Explanation of reference symbols

[0349] 101: Anode, 102: Cathode, 103: EL layer, 111: Hole injection layer, 112: Hole transport layer, 113: Light-emitting layer, 114: Electron transport layer, 115: Electron injection layer, 116: Charge generation layer, 117: P-type layer, 118: Electron conduction layer, 119: Electron injection buffer layer, 400: Substrate, 401: First electrode, 403: EL layer, 404: Second electrode, 405: Sealant, 406: Sealant, 407: Sealing substrate, 412: Pad, 420: IC chip, 501: First electrode, 502: Second electrode, 503: EL layer, 511: First light-emitting unit, 512: Second light Emitting unit, 513: Charge generation layer, 601: Source line driver section, 602: Pixel section, 603: Gate line driver section, 604: Sealing substrate, 605: Sealant, 607: Space, 608: Conduit, 609: FPC (flexible printed circuit), 610: Element substrate, 611: Switching FET612: Current-controlling FET, 613: First electrode, 614: Insulator, 616: EL layer, 617: Second electrode, 618: Light-emitting element, 623: n-channel FET, 624: p-channel FET, 730: Insulating film, 770: Insulating planarization film, 772: Conducting film, 782: Light-emitting element, 783: Droplet ejection device, 784: Droplet, 785: Layer, 786: Light-emitting substance-containing layer, 788: Conducting film, 901: Package, 902: Liquid crystal layer, 903: Backlight unit, 904: Package, 905: Driver IC, 906: Terminal, 951: Substrate, 952: Electrode 953: insulating layer, 954: partition layer, 955: EL layer, 956: electrode, 1001: substrate, 1002: insulating base film, 1003: gate insulating film, 1006: gate electrode, 1007: gate electrode, 1008: gate electrode, 1020: first insulating intermediate film, 1021: second insulating intermediate film, 1022: electrode, 1024W: first electrode of the light-emitting element,1024R: first electrode of the light-emitting element, 1024G: first electrode of the light-emitting element, 1024B: first electrode of the light-emitting element, 1025: partition, 1028: EL layer, 1029: cathode, 1031: sealing substrate, 1032: sealing compound, 1033: transparent base material, 1034R: red color layer, 1034G: green color layer, 1034B: blue color layer, 1035: black layer (black matrix), 1037: third insulating intermediate film, 1040: pixel section, 1041: driver circuit section, 1042: peripheral section, 1400: droplet ejection device, 1402: substrate, 1403: droplet ejection compound, 1404: Imaging means, 1405: head, 1406: dashed line, 1407: control means, 1408: storage medium, 1409: image processing means, 1410: computer, 1411: marker, 1412: head, 1413: material supply source, 1414: material supply source, 1415: material supply source, 1416: head, 2001: housing, 2002: light source, 3001: lighting device,5000: Display area, 5001: Display area, 5002: Display area, 5003: Display area, 5004: Display area, 5005: Display area, 7101: Housing, 7103: Display section, 7105: Foot, 7107: Display section, 7109: Control button, 7110: Remote control, 7201: Main body, 7202: Housing, 7203: Display section, 7204: Keypad, 7205: External connection port, 7206: Pointing device, 7210: Second display section, 7401: Housing, 7402: Display section, 7403: Control knob, 7404: External connection port, 7405: Speaker, 7406: Microphone, 9033: Close, 9034: Switch, 9035: Power switch, 9036: Switch, 9310: Portable information terminal, 9311: Display screen, 9312: Display area, 9313: Joint, 9315: Housing, 9630: Housing, 9631: Display section, 9631a: Display section, 9631b: Display section, 9632a: Touchscreen area, 9632b: Touchscreen area, 9633: Solar cell, 9634: Charge / discharge control circuit, 9635: Battery, 9636: DC-DC converter, 9637: Control button,9638: Converter, 9639: Button,< / beleuchtungsvorrichtung>

Claims

[1] Organic compound represented by the following formula (G1), where: A represents a group which is represented by the following formula (gl); B represents a skeleton consisting of a substituted or unsubstituted naphthobisbenzofuran skeleton, a substituted or unsubstituted naphthobisbenzothiophene skeleton, and a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton; and q 1 or 2 is; Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms; Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group with 6 to 25 carbon atoms; each of R 1 to R 8independently of each other, one consisting of hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms; each of α 1 up to α 4 independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 25 carbon atoms, and Each of l, m, n and p independently represents an integer from 0 to 2. [2] Organic compound according to claim 1, wherein Ar 2 an aromatic hydrocarbon group with 6 to 12 carbon atoms. [3] Organic compound according to claim 1, wherein p is equal to 0. [4] Organic compound according to claim 1, wherein p is 1 and α 4 a phenylene group. [5] Organic compound according to claim 1, where each of l, m and n is independently 0 or 1, and where each of α 1 up to α 3 a phenylene group. [6] Organic compound according to claim 1, wherein 1 equals 0. [7] Organic compound according to claim 1, wherein B is a framework represented by the following formula (B1), and wherein: each of X 2 and X 3 independently represents an oxygen atom or a sulfur atom; one or two of R 10 to R 21 represent a group that is represented by the formula (gl); and each of the others from R 10 to R 21independently of each other, one consisting of hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, and a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. [8] Organic compound according to claim 7, wherein one or two of R 11 , R 12 , R 17 and R 18 represent a group that is represented by the formula (gl). [9] Organic compound according to claim 1, wherein B is a framework represented by the following formula (B2), and wherein: each of X 2 and X 3 independently represents an oxygen atom or a sulfur atom; one or two of R 30 to R 41represent a group that is represented by the formula (gl); and each of the others from R 30 to R 41 independently of each other, one consisting of hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, and a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. [10] Organic compound according to claim 9, wherein one or two of R 31 , R 32 , R 37 and R 38 represent a group that is represented by the formula (gl). [11] Organic compound according to claim 1, wherein B is a framework represented by the following formula (B3), and wherein: each of X 2 and X 3independently represents an oxygen atom or a sulfur atom; one or two of R 50 to R 61 represent a group that is represented by the formula (gl); and each of the others from R 50 to R 61 independently of each other, one consisting of hydrogen, a hydrocarbon group with 1 to 10 carbon atoms, a cyclic hydrocarbon group with 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms, and a substituted or unsubstituted diarylamine group with 12 to 32 carbon atoms. [12] Organic compound according to claim 11, wherein one or two of R 51 , R 52 , R 57 and R 58 represent a group that is represented by the formula (gl). [13] Organic compound according to one of claims 7, 9 or 11, wherein X 2and X 3 These are oxygen atoms. [14] Organic compound according to any one of claims 1, 7, 9 or 11, wherein the molecular weight of the organic compound is 1300 or less. [15] Organic compound according to any one of claims 1, 7, 9 or 11, wherein the molecular weight of the organic compound is 1200 or less. [16] Light-emitting element comprising the organic compound according to any one of claims 1, 7, 9 or 11. [17] Electronic device comprising: the light-emitting element according to claim 16; and at least one consisting of a sensor, a control button, a speaker and a microphone. [18] Lighting device comprising: the light-emitting element according to claim 16; and a case. [19] Electronic device comprising the organic compound according to any one of claims 1, 7, 9 or 11.

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