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

Abstract

The present invention provides a novel organic compound, a puropyrazine derivative. It is an organic compound having a puropyrazine backbone and represented by the following general formula (G1). In addition, in the general formula (G1), Q represents oxygen or sulfur. Also, Ar1 represents a substituted or unsubstituted condensation direction ring. Also, R1 and R2 each independently represent hydrogen or a group having a total of 1 to 100 carbon atoms, and at least one of R1 and R2 has a hole transport framework.

Description

Technology Field

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. However, one embodiment of the present invention is not limited to the technical fields described above. That is, one embodiment of the present invention relates to an article, a method, a method of manufacturing, or a method of driving. Alternatively, one embodiment of the present invention relates to a process, a machine, a product, or a composition of matter. Furthermore, specifically, semiconductor devices, display devices, liquid crystal display devices, etc., may be cited as examples. Background Technology

[0002] Light-emitting devices (also called organic EL devices) that have an EL layer sandwiched between a pair of electrodes have characteristics such as being thin, lightweight, having high-speed response to input signals, and low power consumption, so displays incorporating them are attracting attention as next-generation flat panel displays.

[0003] In a light-emitting device, by applying a voltage between a pair of electrodes, electrons and holes injected from each electrode recombine in the EL layer, causing the light-emitting material (organic compound) contained in the EL layer to become excited, and light is emitted when the excited state returns to the ground state. Furthermore, as for the types of excited states, the singlet excited state (S * ) and triplet excited state (T * There is ), and emission from the singlet excited state is called fluorescence, and emission from the triplet excited state is called phosphorescence. In addition, their statistical generation ratio in a light-emitting device is S * :T * It is thought to be 1:3. The emission spectrum obtained from a luminescent material is unique to that luminescent material, and by using different types of organic compounds as luminescent materials, a luminescent device exhibiting light of various colors can be obtained.

[0004] As for organic compounds, many types of substances and methods for their synthesis have been developed so far, and their applications and fields of development are diverse. In the field of biochemistry, methods for easily synthesizing substances having a naphthofuropyrazine backbone have been reported (see, for example, Non-Patent Literature 1).

[0005] However, there are no reports yet of new materials being developed using substances containing this naphthofuropyrazine backbone as raw materials. Prior art literature

[0006] K. Shiva Kumar, Raju Adepu, Ravikumar Kapavarapu, D. Rambabu, G. Rama Krishna, C. Malla Reddy, K. Krishna Priya, Kishore VL Parsa, Manojit Pal, "AlCl3 induced C-arylation / cyclization in a single pot: a new route to benzofuran fused N-heterocycles of pharmacological interest", Tetrahedron Letters, 2012, Vol.53, p.1134-1138. The problem to be solved

[0007] Therefore, in one embodiment of the present invention, a novel organic compound is provided using a material having a puropyrazine backbone (including naphthofuropyrazine) as a raw material. In addition, in another embodiment of the present invention, a puropyrazine derivative which is a novel organic compound is provided. In addition, in one embodiment of the present invention, a novel organic compound that can be used in a light-emitting device is provided. In addition, in one embodiment of the present invention, a novel organic compound that can be used in the EL layer of a light-emitting device is provided. In addition, a novel light-emitting device with high reliability using the novel organic compound of one embodiment of the present invention is provided. In addition, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. In addition, the description of these problems does not interfere with the existence of other problems. In addition, one embodiment of the present invention is not necessarily required to solve all of these problems. In addition, other problems are naturally apparent from the description in the specification, drawings, claims, etc., and other problems can be derived from the description in the specification, drawings, claims, etc. means of solving the problem

[0008] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0009] [Chemical Formula 1]

[0010]

[0011] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents a substituted or unsubstituted condensation direction ring. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them has a hole transport skeleton.

[0012] In addition, another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0013] [Chemical Formula 2]

[0014]

[0015] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents any one of substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted chrysene. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them has a hole transport skeleton.

[0016] In addition, another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0017] [Chemical Formula 3]

[0018]

[0019] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents a substituted or unsubstituted condensation direction ring. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them is a group containing a condensation ring.

[0020] In addition, another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0021] [Chemical Formula 4]

[0022]

[0023] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1represents any one of substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted chrysene. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them is a group containing a condensation ring.

[0024] In addition, in the above general formula (G1), Ar 1 It is characterized by being represented by any one of the following general formulas (t1) to (t3).

[0025] [Chemical Formula 5]

[0026]

[0027] In the above general formulas (t1) to (t3), R 3 to R 24 Each represents independently any one of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C3 to C7 cycloalkyl group, and a substituted or unsubstituted C6 to C30 aryl group. Additionally, * represents a link in general formula (G1).

[0028] In addition, in each of the above configurations, the general formula (G1) is characterized as being any one of the following general formulas (G1-1) to general formula (G1-4).

[0029] [Chemical Formula 6]

[0030]

[0031] In the above general formulas (G1-1) to (G1-4), Q represents oxygen or sulfur. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them has a hole transport framework. Also, R3 to R 8 and R 17 to R 24 Each represents independently any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0032] In addition, in each of the above configurations, the hole transport backbone is characterized as being any one of a substituted or unsubstituted diarylamino group, a substituted or unsubstituted condensed aromatic hydrocarbon ring, and a substituted or unsubstituted π-electron excess condensed heteroaromatic ring.

[0033] In addition, in the above-mentioned composition, the condensation ring is characterized as being either a substituted or unsubstituted condensed aromatic hydrocarbon ring or a substituted or unsubstituted π-electron excess condensed heteroaromatic ring. In addition, the condensation ring is characterized as being a substituted or unsubstituted condensed heteroaromatic ring having any one of a dibenzothiophene backbone, a dibenzofuran backbone, and a carbazole backbone. In addition, the condensation ring is characterized as being a substituted or unsubstituted condensed aromatic hydrocarbon ring having any one of a naphthalene backbone, a fluorene backbone, a triphenylene backbone, and a phenanthrene backbone.

[0034] In addition, in each of the above configurations, R in the general formula (G1) 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them is characterized by being represented by the following general formula (u1).

[0035] [Chemical Formula 7]

[0036]

[0037] In the above general formula (u1), α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n represents an integer from 0 to 4. Also, A 1 represents a substituted or unsubstituted aryl group having a total of 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms. Also, * represents a link in the general formula (G1).

[0038] In addition, in the above general formula (u1), A 1 is the following general formula (A 1 -1) to general formula (A 1 -17) is characterized by being one of the following.

[0039] [Chemical Formula 8]

[0040]

[0041] The above general formula (A 1 -1) to general formula (A 1 In -17), R A1 to R A11 Each represents independently any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0042] In addition, in the above general formula (u1), α is characterized as being any one of the following general formulas (Ar-1) to general formula (Ar-14).

[0043] [Chemical Formula 9]

[0044]

[0045] In the above general formulas (Ar-1) to (Ar-14), R B1 to R B14Each represents independently any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0046] Additionally, another embodiment of the present invention is an organic compound represented by any one of structural formula (100), structural formula (123), structural formula (125), structural formula (126), structural formula (133), structural formula (156), structural formula (208), structural formula (238), structural formula (239), structural formula (244), structural formula (245), and structural formula (246).

[0047] [Chemical Formula 10]

[0048]

[0049] In addition, a novel organic compound (see Embodiment 1) that serves as a raw material for synthesizing an organic compound which is one embodiment of the present invention described above is also included in the present invention. In addition, another embodiment of the present invention is a light-emitting device using an organic compound which is one embodiment of the present invention described above. In addition, a light-emitting device having a guest material in addition to the organic compound is also included in the present invention.

[0050] Another embodiment of the present invention is a light-emitting element using an organic compound, which is one embodiment of the present invention described above. Additionally, a light-emitting element formed using an organic compound, which is one embodiment of the present invention, in an EL layer provided between a pair of electrodes or in a light-emitting layer included in the EL layer is also included in the present invention. Furthermore, in addition to the light-emitting element, a light-emitting element having a layer (e.g., a cap layer) in contact with an electrode and having an organic compound is also included in the light-emitting element and is included in the present invention. In addition, a light-emitting device having a transistor, a substrate, etc., in addition to the light-emitting element is also included in the scope of the invention. Furthermore, in addition to these light-emitting devices, an electronic device or lighting device having a microphone, a camera, an operating button, an external connection part, a housing, a cover, a support, or a speaker, etc., is also included in the scope of the invention.

[0051] Furthermore, one embodiment of the present invention includes a light-emitting device having a light-emitting element, and also includes a lighting device having a light-emitting device. Accordingly, in this specification, the term "light-emitting device" refers to an image display device or a light source (including a lighting device). Additionally, modules equipped with connectors such as, for example, an FPC (Flexible Printed Circuit) or a TCP (Tape Carrier Package) on the light-emitting device, modules provided with a printed circuit board at the end of a TCP, or modules in which an IC (Integrated Circuit) is directly mounted on the light-emitting element using the COG (Chip On Glass) method are all included in the light-emitting device. Effects of the invention

[0052] In one embodiment of the present invention, a novel organic compound having a material having a puropyrazine backbone (including naphthofuropyrazine) can be provided. In another embodiment of the present invention, a puropyrazine derivative that is a novel organic compound can be provided. In another embodiment of the present invention, a novel organic compound that can be used in a light-emitting device can be provided. In another embodiment of the present invention, a novel organic compound that can be used in the EL layer of a light-emitting device can be provided. In addition, a novel light-emitting device with high reliability using the novel organic compound of one embodiment of the present invention can be provided. In addition, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. In addition, the description of these effects does not interfere with the existence of other effects. In addition, one embodiment of the present invention is not necessarily required to have all of these problems. In addition, other effects are naturally apparent from the description in the specification, drawings, claims, etc., and other effects can be derived from the description in the specification, drawings, claims, etc. Brief explanation of the drawing

[0053] FIG. 1 is a diagram for explaining the structure of a light-emitting element. FIG. 2 is a drawing for explaining a light-emitting device. FIG. 3 is a drawing for explaining a light-emitting device. FIG. 4 is a drawing for explaining an electronic device. FIG. 5 is a drawing for explaining an electronic device. FIG. 6 is a drawing for explaining an automobile. FIG. 7 is a drawing for explaining a lighting device. FIG. 8 is a drawing for explaining a lighting device. FIG. 9 is of an organic compound represented by structural formula (100). 1 H-NMR chart. FIG. 10 shows the ultraviolet and visible absorption spectrum and emission spectrum of an organic compound represented by structural formula (100). FIG. 11 is a drawing for explaining a light-emitting element. Figure 12 is a diagram showing the current density-luminance characteristics of light-emitting element 1 and comparison light-emitting element 2. Figure 13 is a diagram showing the voltage-luminance characteristics of light-emitting element 1 and comparison light-emitting element 2. FIG. 14 is a diagram showing the luminance-current efficiency characteristics of light-emitting element 1 and comparison light-emitting element 2. FIG. 15 is a diagram showing the voltage-current characteristics of light-emitting element 1 and comparison light-emitting element 2. FIG. 16 is a diagram showing the emission spectra of light-emitting element 1 and comparison light-emitting element 2. FIG. 17 is a diagram showing the reliability of light-emitting element 1 and comparison light-emitting element 2. Figure 18 is a diagram showing the current density-luminance characteristics of light-emitting element 3. FIG. 19 is a diagram showing the voltage-luminance characteristics of light-emitting element 3. FIG. 20 is a diagram showing the luminance-current efficiency characteristics of light-emitting element 3. FIG. 21 is a diagram showing the voltage-current characteristics of light-emitting element 3. FIG. 22 is a diagram showing the emission spectrum of light-emitting element 3. FIG. 23 is a diagram showing the reliability of light-emitting element 3. Figure 24 is a diagram showing the current density-luminance characteristics of light-emitting element 4. FIG. 25 is a diagram showing the voltage-luminance characteristics of light-emitting element 4. FIG. 26 is a diagram showing the luminance-current efficiency characteristics of light-emitting element 4. FIG. 27 is a diagram showing the voltage-current characteristics of light-emitting element 4. FIG. 28 is a diagram showing the emission spectrum of light-emitting element 4. FIG. 29 is a diagram showing the reliability of light-emitting element 4. Figure 30 is a diagram showing the current density-luminance characteristics of light-emitting element 5. Figure 31 is a diagram showing the voltage-luminance characteristics of light-emitting element 5. FIG. 32 is a diagram showing the luminance-current efficiency characteristics of light-emitting element 5. FIG. 33 is a diagram showing the voltage-current characteristics of light-emitting element 5. FIG. 34 is a diagram showing the emission spectrum of light-emitting element 5. FIG. 35 is a diagram showing the reliability of light-emitting element 5. FIG. 36 is an organic compound represented by structural formula (123). 1 H-NMR chart. FIG. 37 is an organic compound represented by structural formula (125). 1 H-NMR chart. FIG. 38 is an organic compound represented by structural formula (126). 1 H-NMR chart. FIG. 39 is an organic compound represented by structural formula (133). 1 H-NMR chart. FIG. 40 is an organic compound represented by structural formula (156). 1 H-NMR chart. FIG. 41 is an organic compound represented by structural formula (208). 1 H-NMR chart. FIG. 42 is an organic compound represented by structural formula (238). 1 H-NMR chart. FIG. 43 is an organic compound represented by structural formula (239). 1 H-NMR chart. FIG. 44 is an organic compound represented by structural formula (244). 1 H-NMR chart. FIG. 45 is an organic compound represented by structural formula (245). 1 H-NMR chart. FIG. 46 is an organic compound represented by structural formula (246). 1 H-NMR chart. Figure 47 is a diagram showing the current density-luminance characteristics of light-emitting element 8. FIG. 48 is a diagram showing the voltage-luminance characteristics of light-emitting element 8. FIG. 49 is a diagram showing the luminance-current efficiency characteristics of light-emitting element 8. FIG. 50 is a diagram showing the voltage-current characteristics of light-emitting element 8. FIG. 51 is a diagram showing the emission spectrum of light-emitting element 8. FIG. 52 is a diagram showing the reliability of light-emitting element 8. Figure 53 is a diagram showing the current density-luminance characteristics of a light-emitting element 9. Figure 54 is a diagram showing the voltage-luminance characteristics of a light-emitting element 9. FIG. 55 is a diagram showing the luminance-current efficiency characteristics of a light-emitting element 9. FIG. 56 is a diagram showing the voltage-current characteristics of a light-emitting element 9. FIG. 57 is a diagram showing the emission spectrum of light-emitting element 9. FIG. 58 is a diagram showing the reliability of the light-emitting element 9. FIG. 59 is a diagram showing the current density-luminance characteristics of light-emitting elements 10 to 15. FIG. 60 is a diagram showing the voltage-luminance characteristics of light-emitting elements 10 to 15. FIG. 61 is a diagram showing the luminance-current efficiency characteristics of light-emitting elements 10 to 15. FIG. 62 is a diagram showing the voltage-current characteristics of light-emitting elements 10 to 15. FIG. 63 is a diagram showing the emission spectra of light-emitting elements 10 to 15. FIG. 64 is a diagram showing the reliability of light-emitting elements 10 to 15. Figure 65 is a diagram showing the current density-luminance characteristics of a light-emitting element 16 and a comparison light-emitting element 17. FIG. 66 is a diagram showing the voltage-luminance characteristics of a light-emitting element 16 and a comparison light-emitting element 17. FIG. 67 is a diagram showing the luminance-current efficiency characteristics of a light-emitting element 16 and a comparison light-emitting element 17. FIG. 68 is a diagram showing the voltage-current characteristics of a light-emitting element 16 and a comparison light-emitting element 17. FIG. 69 is a diagram showing the emission spectra of a light-emitting element 16 and a comparison light-emitting element 17. FIG. 70 is a diagram showing the reliability of a light-emitting element 16 and a comparative light-emitting element 17. Specific details for implementing the invention

[0054] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the description below, and its form and details may be varied without departing from the spirit and scope of the present invention. Accordingly, the present invention is not to be interpreted as being limited to the contents of the embodiments described below.

[0055] In addition, the actual location, size, and range of each component shown in drawings, etc., may not be indicated to facilitate understanding. Therefore, the disclosed invention is not necessarily limited to the location, size, and range shown in drawings, etc.

[0056] In addition, when describing the composition of the invention with reference to the drawings in this specification and others, reference numerals indicating the same thing are used commonly even between different drawings.

[0057] (Embodiment 1)

[0058] In this embodiment, an organic compound that is one form of the present invention is described. Additionally, the organic compound that is one form of the present invention has a naphthofuropyrazine backbone and is represented by the following general formula (G1).

[0059] [Chemical Formula 11]

[0060]

[0061] Also, in the general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents a substituted or unsubstituted condensation direction ring. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them has a hole transport skeleton.

[0062] In addition, another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0063] [Chemical Formula 12]

[0064]

[0065] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents any one of substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted chrysene. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them has a hole transport skeleton.

[0066] In addition, another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0067] [Chemical Formula 13]

[0068]

[0069] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents a substituted or unsubstituted condensation direction ring. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2At least one of them is a group containing a condensation ring.

[0070] In addition, another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0071] [Chemical Formula 14]

[0072]

[0073] In the above general formula (G1), Q represents oxygen or sulfur. Also, Ar 1 represents any one of substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted chrysene. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them is a group containing a condensation ring.

[0074] In addition, in the above general formula (G1), Ar 1 It is represented by any one of the following general formulas (t1) to (t3).

[0075] [Chemical Formula 15]

[0076]

[0077] In the above general formulas (t1) to (t3), R 3 to R 24 Each represents independently any one of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C3 to C7 cycloalkyl group, and a substituted or unsubstituted C6 to C30 aryl group. Additionally, * represents a link in general formula (G1).

[0078] In addition, in each of the above configurations, the general formula (G1) is any one of the following general formulas (G1-1) to general formula (G1-4).

[0079] [Chemical Formula 16]

[0080]

[0081] In the above general formulas (G1-1) to (G1-4), Q represents oxygen or sulfur. Also, R 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them has a hole transport framework. Also, R 3 to R 8 and R 17 to R 24 Each represents independently any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0082] In addition, in each of the above configurations, R 1 and R 2The hole transport backbone having at least one of the following is any one of a substituted or unsubstituted diarylamino group, a substituted or unsubstituted condensed aromatic hydrocarbon ring, and a substituted or unsubstituted π-electron excess condensed heteroaromatic ring. The condensed aromatic hydrocarbon ring preferably has any one of a naphthalene backbone, a fluorene backbone, a triphenylene backbone, and a phenanthrene backbone. Additionally, the π-electron excess condensed heteroaromatic ring preferably is a condensed heteroaromatic ring having any one of a dibenzothiophene backbone, a dibenzofuran backbone, and a carbazole backbone. The above-mentioned condensed heterodirectional ring includes not only carbazole, dibenzothiophene, and dibenzofuran, but also condensed rings having a carbazole backbone, a dibenzothiophene backbone, or a dibenzofuran backbone within the ring structure (i.e., condensed rings in which a ring is further condensed to a carbazole backbone, a dibenzothiophene backbone, or a dibenzofuran backbone), such as benzocarbazole, dibenzocarbazole, indolocarbazole, benzindolocarbazole, dibenzindolobenzocarbazole, benzindolobenzocarbazole, benzonaphthothiophene, and benzonaphthofuran.

[0083] In addition, in each of the above configurations, R 1 and R 2The condensation ring having at least one of the above is either a substituted or unsubstituted condensed aromatic hydrocarbon ring or a substituted or unsubstituted π-electron excess condensed heteroaromatic ring. In particular, it is preferable that the condensation ring is a substituted or unsubstituted condensed aromatic hydrocarbon ring having any one of a naphthalene backbone, a fluorene backbone, a triphenylene backbone, and a phenanthrene backbone. In addition, in particular, it is preferable that the condensation ring is a substituted or unsubstituted condensed heteroaromatic ring having any one of a dibenzothiophene backbone, a dibenzofuran backbone, and a carbazole backbone. The above-mentioned condensed heterodirectional ring includes not only carbazole, dibenzothiophene, and dibenzofuran, but also condensed rings having a carbazole backbone, a dibenzothiophene backbone, or a dibenzofuran backbone within the ring structure (i.e., condensed rings in which a ring is further condensed to a carbazole backbone, a dibenzothiophene backbone, or a dibenzofuran backbone), such as benzocarbazole, dibenzocarbazole, indolocarbazole, benzindolocarbazole, dibenzindolobenzocarbazole, benzindolobenzocarbazole, benzonaphthothiophene, and benzonaphthofuran.

[0084] In addition, in each of the above configurations, R in the general formula (G1) 1 and R 2 Each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms, and R 1 and R 2 At least one of them is a group represented by the following general formula (u1).

[0085] [Chemical Formula 17]

[0086]

[0087] In the above general formula (u1), α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n represents an integer from 0 to 4. Also, A 1 ...represents a substituted or unsubstituted aryl group having a total of 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms.

[0088] In addition, A in the above general formula (u1) 1 represents a substituted or unsubstituted aryl group having a total of 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms, specifically the following general formula (A 1 -1) to general formula (A 1 -17) is characterized by being one of the following.

[0089] [Chemical Formula 18]

[0090]

[0091] The above general formula (A 1 -1) to general formula (A 1 In -17), R A1 to R A11 Each represents independently any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0092] In addition, in the above general formula (u1), α is characterized as being any one of the following general formulas (Ar-1) to general formula (Ar-14).

[0093] [Chemical Formula 19]

[0094]

[0095] In the above general formulas (Ar-1) to (Ar-14), R B1 to R B14 Each represents independently any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0096] In addition, R in the above general formula (G1) and the above general formulas (G1-1) to (G1-4). 1 and R 2Examples of groups having a total of 1 to 100 carbon atoms include substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 7 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. However, R 1 and R 2 At least one of them has the aforementioned hole transport framework or condensation ring.

[0097] In addition, where the substituted or unsubstituted condensed aromatic ring in the above general formula (G1) has a substituent, where the substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted chrysene in the above general formula (G1) have a substituent, where the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or the substituted or unsubstituted aryl group having 6 to 30 carbon atoms have a substituent in the above general formulas (t1) to (t3), where the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or the substituted or unsubstituted aryl group having 6 to 30 carbon atoms have a substituent in the above general formulas (G1-1) to (G1-4), where the substituted or unsubstituted condensed aromatic hydrocarbon ring or the substituted or unsubstituted Where the π-electron excess type condensed hetero-directional ring has a substituent, where the substituted or unsubstituted arylene group having 6 to 25 carbon atoms in the general formula (u1), the substituted or unsubstituted aryl group having a total of 6 to 30 carbon atoms, or the substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms has a substituent, where the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or the substituted or unsubstituted aryl group having 6 to 30 carbon atoms has a substituent, or R in the general formula (G1) and the general formulas (G1-1) to (G1-4) 1 and R 2In the case where a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms has a substituent, the substituent may be an alkyl group having 1 to 7 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, or a hexyl group; a cycloalkyl group having 5 to 7 carbon atoms such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or an 8,9,10-trinobonanyl group; or an aryl group having 6 to 12 carbon atoms such as a phenyl group, a naphthyl group, or a biphenyl group.

[0098] In addition, the above general formulas (t1) to (t3), the above general formulas (G1-1) to (G1-4), or the general formula (A 1 -1) to general formula (A 1 Specific examples of alkyl groups having 1 to 6 carbon atoms in -17) include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group, etc.

[0099] In addition, the above general formulas (t1) to (t3), the above general formulas (G1-1) to (G1-4), or the general formula (A 1 -1) to general formula (A 1 Specific examples of cycloalkyl groups having 3 to 7 carbon atoms in -17) include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, 1-methylcyclohexyl groups, 2,6-dimethylcyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc.

[0100] In addition, the above general formulas (t1) to (t3), the above general formulas (G1-1) to (G1-4), or the general formula (A 1 -1) to general formula (A 1 Specific examples of aryl groups having 6 to 30 carbon atoms in -17) include phenyl groups, o-tolyl groups, m-tolyl groups, p-tolyl groups, mesithyl groups, o-biphenyl groups, m-biphenyl groups, p-biphenyl groups, 1-naphthyl groups, 2-naphthyl groups, fluorenyl groups, 9,9-dimethylfluorenyl groups, spirofluorenyl groups, phenanthreneyl groups, anthraceneyl groups, fluorantheneyl groups, etc.

[0101] In addition, among the above general formula (G1) and the above general formulas (G1-1) to (G1-4), R 1 and R 2 Specific examples of aryl groups having 6 to 30 carbon atoms in the group having a total of 1 to 100 carbon atoms include phenyl groups, o-tolyl groups, m-tolyl groups, p-tolyl groups, mesithyl groups, o-biphenyl groups, m-biphenyl groups, p-biphenyl groups, 1-naphthyl groups, 2-naphthyl groups, fluorenyl groups, 9,9-dimethylfluorenyl groups, spirofluorenyl groups, phenanthreneyl groups, anthraceneyl groups, fluorantheneyl groups, etc. In addition, R 1 and R 2 Specific examples of heteroaryl groups having 3 to 30 carbon atoms in a group having 1 to 100 carbon atoms include monovalent groups such as carbazole, benzocarbazole, dibenzocarbazole, indolocarbazole, benzindolocarbazole, dibenzindolocarbazole, benzindolobenzocarbazole, dibenzothiophene, benzonaphthothiophene, dibenzofuran, and benzonaphthofuran.

[0102] Next, specific structural formulas of organic compounds that are one embodiment of the present invention described above are shown below. However, the present invention is not limited to these.

[0103] [Chemical Formula 20]

[0104]

[0105] [Chemical Formula 21]

[0106]

[0107] [Chemical Formula 22]

[0108]

[0109] [Chemical Formula 23]

[0110]

[0111] [Chemical Formula 24]

[0112]

[0113] [Chemical Formula 25]

[0114]

[0115] [Chemical Formula 26]

[0116]

[0117] [Chemical Formula 27]

[0118]

[0119] [Chemical Formula 28]

[0120]

[0121] [Chemical Formula 29]

[0122]

[0123] [Chemical Formula 30]

[0124]

[0125] [Chemical Formula 31]

[0126]

[0127] [Chemical Formula 32]

[0128]

[0129] [Chemical Formula 33]

[0130]

[0131] Additionally, the organic compound represented by the above structural formula (100) to structural formula (251) is an example of the organic compound represented by the above general formula (G1), but the organic compound that is one form of the present invention is not limited thereto.

[0132] Next, an example of a method for synthesizing an organic compound represented by the following general formula (G1'), which is one form of the present invention, will be described. In addition, the organic compound represented by the following general formula (G1') is a puropyrazine derivative in which the condensation direction ring is condensed or a thienopyrazine derivative in which the condensation direction ring is condensed, and is one form of the organic compound represented by the general formula (G1).

[0133] [Chemical Formula 34]

[0134]

[0135] In the general formula (G1'), Q represents oxygen or sulfur. R 1 represents a group having 1 to 100 carbon atoms, and R 1 represents the hole transport framework. Also, Ar 1 It represents a substituted or unsubstituted condensation direction ring.

[0136] <<Synthesization method of organic compounds represented by the general formula (G1')>>

[0137] Various reactions can be applied to the synthesis of the organic compound represented by the above general formula (G1'), and, for example, the organic compound represented by the general formula (G1') can be synthesized by a simple method shown in the synthesis scheme below.

[0138] First, as shown in the following scheme (A-1), an intermediate (a3) ​​is obtained by coupling an arylboronic acid (a1) substituted with a methyloxy group or a methylthiogenic group with a pyrazine derivative (a2) substituted with an amino group and a halogen, and then the intermediate (a3) ​​is reacted with tert-butyl nitrite and cyclized to obtain a puropyrazine derivative with a condensed condensation direction ring or a thienopyrazine derivative (a4) with a condensed condensation direction ring. In addition, Y in the pyrazine derivative (a4) 1 In the case of this halogen, the boronic acid of the aromatic ring containing the halogen (Y 3 -B 1 The intermediate (a5) obtained by coupling ) can also be used in subsequent reactions, just like the pyrazine derivative (a4).

[0139] [Chemical Formula 35]

[0140]

[0141] Also, in the synthesis scheme (A-1), Q represents oxygen or sulfur. Also, Ar 1 represents a substituted or unsubstituted condensation direction ring. Also, Y 1 represents a halogen or an aromatic ring containing a halogen, and Y 1 is one or two. Also, Y 2 represents a halogen. Also, Y 3 represents an aromatic ring containing a halogen, and Y 3 is one or two. Also, B 1 ... represents boronic acid, boronic acid ester, or cyclic triolborate salt, etc. In addition, as the cyclic triolborate salt, potassium salt or sodium salt may be used in addition to lithium salt.

[0142] In addition, in the above synthesis scheme (A-1), the organic compound represented by general formula (a4) and general formula (a5) is a raw material for an organic compound that is one form of the present invention, as shown in the synthesis scheme (A-2) below. Furthermore, the organic compound represented by general formula (a4) and general formula (a5) is a novel organic compound and is included in one form of the present invention. The specific structural formula of the organic compound represented by general formula (a4) and general formula (a5) is shown below.

[0143] [Chemical Formula 36]

[0144]

[0145] [Chemical Formula 37]

[0146]

[0147] [Chemical Formula 38]

[0148]

[0149] Additionally, the organic compound represented by the above structural formulas (300) to (347) is an example of the organic compound represented by the above general formula (a4) and general formula (a5), but the organic compound that is one form of the present invention is not limited thereto.

[0150] Next, as shown in the following scheme (A-2), an organic compound represented by the general formula (G1') is obtained by coupling a boronic acid compound (b1) with a condensed puropyrazine derivative or a condensed thienopyrazine derivative (a4) obtained by the scheme (A-1).

[0151] [Chemical Formula 39]

[0152]

[0153] Also, in the synthesis scheme (A-2), Q represents oxygen or sulfur. Also, R 1 represents a group having 1 to 100 carbon atoms, and R 1 It has a hole transport framework. Also, Ar1 represents a substituted or unsubstituted condensation direction ring. Also, Y 1 represents one or two halogens, and B 2 represents boronic acid, boronic acid ester, or cyclic triolborate salt, etc. In addition, as the cyclic triolborate salt, potassium salt or sodium salt may be used in addition to lithium salt.

[0154] In addition, since the arylboronic acid (a1) substituted with a methyloxy group or a methylthio group, the pyrazine derivative (a2) substituted with an amino group and a halogen, and the boronic acid compound (b1) used in the above synthesis schemes (A-1) and (A-2) are commercially available or synthesizable in various forms, the puropyrazine derivative or thienopyrazine derivative with a condensed

[0155] Up to this point, an example of a puropyrazine derivative in which a condensation direction ring is condensed or a thienopyrazine derivative in which a condensation direction ring is condensed, and a method of synthesizing the same, which is one embodiment of the present invention, has been described, but the present invention is not limited thereto and may be synthesized using any other synthesis method.

[0156] Furthermore, in this embodiment, one embodiment of the present invention has been described. In addition, in another embodiment, one embodiment of the present invention will be described. However, one embodiment of the present invention is not limited to these. That is, since various forms of the invention are described in this embodiment and other embodiments, one embodiment of the present invention is not limited to a specific form.

[0157] The configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0158] (Embodiment 2)

[0159] In this embodiment, a light-emitting element using the organic compound described in Embodiment 1 is described with reference to FIG. 1.

[0160] <<Basic Structure of Light-Emitting Devices>>

[0161] First, the basic structure of the light-emitting element is described. Figure 1 (A) illustrates a light-emitting element having an EL layer containing a light-emitting layer between a pair of electrodes. Specifically, it has a structure in which an EL layer (103) is sandwiched between a first electrode (101) and a second electrode (102).

[0162] In addition, FIG. 1 (B) illustrates a light-emitting device having a stacked structure (tandem structure) having a plurality of EL layers (103a and 103b) (two layers in FIG. 1 (B)) between a pair of electrodes and a charge generating layer (104) between the EL layers. Since the light-emitting device of the tandem structure can be driven at a low voltage, a light-emitting device with low power consumption can be realized.

[0163] The charge generating layer (104) has the function of injecting electrons into one of the EL layer (103a) and the EL layer (103b) and injecting holes into the other when a voltage is applied to the first electrode (101) and the second electrode (102). Accordingly, in (B) of FIG. 1, when a voltage is applied such that the potential of the first electrode (101) becomes higher than the potential of the second electrode (102), electrons are injected into the EL layer (103a) from the charge generating layer (104), and holes are injected into the EL layer (103b).

[0164] Additionally, the charge generating layer (104) is preferably transparent to visible light in terms of light extraction efficiency (specifically, the transmittance of visible light to the charge generating layer (104) is 40% or more). Additionally, the charge generating layer (104) functions even if its conductivity is lower than that of the first electrode (101) or the second electrode (102).

[0165] Additionally, (C) of FIG. 1 illustrates a stacked structure of an EL layer (103) of a light-emitting element, which is one embodiment of the present invention. However, in this case, the first electrode (101) functions as an anode. The EL layer (103) has a structure in which a hole injection layer (111), a hole transport layer (112), a light-emitting layer (113), an electron transport layer (114), and an electron injection layer (115) are sequentially stacked on the first electrode (101). Furthermore, even in the case of having multiple EL layers as in the tandem structure shown in (B) of FIG. 1, each EL layer is sequentially stacked from the anode side as described above. Also, when the first electrode (101) is a cathode and the second electrode (102) is a positive electrode, the stacking order is reversed.

[0166] Since the light-emitting layer (113) included in the EL layers (103, 103a, and 103b) each has a light-emitting material or a combination of multiple materials appropriately combined, it can be configured to obtain fluorescent light emission or phosphorescent light emission that exhibits a desired light emission color. Additionally, the light-emitting layer (113) may be configured as a stacked structure with different light emission colors. In this case, the light-emitting material or other materials used in each stacked light-emitting layer may be different materials. Additionally, it may be configured such that different light emission colors are obtained from each of the multiple EL layers (103a and 103b) shown in (B) of FIG. 1. In this case as well, the light-emitting material or other materials used in each light-emitting layer may be different materials.

[0167] In addition, in a light-emitting device which is one embodiment of the present invention, for example, the first electrode (101) shown in (C) of FIG. 1 is made into a reflective electrode and the second electrode (102) is made into a semi-transparent / semi-reflective electrode and thus forms a micro-light resonator (microcavity) structure, so that the light emitted from the light-emitting layer (113) included in the EL layer (103) is resonated between the two electrodes, thereby making the light emitted from the second electrode (102) stronger.

[0168] In addition, when the first electrode (101) of the light-emitting element is a reflective electrode formed by a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by controlling the thickness of the transparent conductive film. Specifically, with respect to the wavelength λ of light obtained from the light-emitting layer (113), it is preferable to adjust the distance between the first electrode (101) and the second electrode (102) to be around mλ / 2 (where m is a natural number).

[0169] In addition, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer (113), it is preferable to adjust the optical distance from the first electrode (101) to the region (light-emitting region) where the desired light of the light-emitting layer (113) is obtained, and the optical distance from the second electrode (102) to the region (light-emitting region) where the desired light of the light-emitting layer (113) is obtained, so that they are each (2m'+1)λ / 4 (where m' is a natural number). In addition, the light-emitting region here refers to the recombination region between holes and electrons in the light-emitting layer (113).

[0170] By making such optical adjustments, the spectrum of a specific monochromatic light obtained from the light-emitting layer (113) can be narrowed to obtain light emission with good color purity.

[0171] However, in this case, the optical distance between the first electrode (101) and the second electrode (102) can be strictly defined as the sum of the thicknesses from the reflection area at the first electrode (101) to the reflection area at the second electrode (102). However, since it is difficult to accurately determine the reflection area at the first electrode (101) or the second electrode (102), the above-described effect can be sufficiently obtained by assuming an arbitrary position of the first electrode (101) and the second electrode (102) as the reflection area. In addition, the optical distance between the first electrode (101) and the light-emitting layer where the desired light is obtained can be strictly defined as the optical distance between the reflection area at the first electrode (101) and the light-emitting area at the light-emitting layer where the desired light is obtained. However, since it is difficult to strictly determine the reflection area at the first electrode (101) or the light-emitting area at the light-emitting layer where the desired light is obtained, it is assumed that the above-described effect can be sufficiently obtained by assuming an arbitrary position of the first electrode (101) as the reflection area and an arbitrary position of the light-emitting layer where the desired light is obtained as the light-emitting area.

[0172] Since the light-emitting element shown in (C) of Fig. 1 has a microcavity structure, it is possible to extract light of different wavelengths (monochromatic light) even with the same EL layer. Therefore, separate coloring (e.g., RGB) to obtain different light emission colors becomes unnecessary. Consequently, it is easy to achieve high precision. In addition, it can be combined with a coloring layer (color filter). Furthermore, since the light emission intensity in the frontal direction of a specific wavelength can be increased, low power consumption can be achieved.

[0173] The light-emitting element shown in (E) of FIG. 1 is an example of a light-emitting element having a tandem structure shown in (B) of FIG. 1, and as shown in the drawing, it has a structure in which three EL layers (103a, 103b, and 103c) are stacked with charge generating layers (104a and 104b) interposed. In addition, each of the three EL layers (103a, 103b, and 103c) has a light-emitting layer (113a, 113b, and 113c), and the light-emitting color of each light-emitting layer can be freely combined. For example, the light-emitting layer (113a) can be blue, the light-emitting layer (113b) can be any one of red, green, and yellow, and the light-emitting layer (113c) can be blue, but the light-emitting layer (113a) can be red, the light-emitting layer (113b) can be any one of blue, green, and yellow, and the light-emitting layer (113c) can be red.

[0174] In addition, in a light-emitting device which is one embodiment of the present invention described above, at least one of the first electrode (101) and the second electrode (102) is made of a light-transmitting electrode (transparent electrode, semi-transparent / semi-reflective electrode, etc.). When the light-transmitting electrode is a transparent electrode, the transmittance of visible light of the transparent electrode is 40% or more. In addition, when it is a semi-transparent / semi-reflective electrode, the reflectance of visible light of the semi-transparent / semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. In addition, these electrodes have a resistivity of 1×10 -2 It is desirable that it be Ωcm or less.

[0175] In addition, in the light-emitting element which is one embodiment of the present invention described above, when one of the first electrode (101) and the second electrode (102) is a reflective electrode (reflective electrode), the reflectance of visible light of the reflective electrode is 40% or more and 100% or less, preferably 70% or more and 100% or less. In addition, this electrode has a resistivity of 1×10 -2 It is desirable that it be Ωcm or less.

[0176] <<Specific Structure and Fabrication Method of Light-Emitting Devices>>

[0177] Next, a specific structure and manufacturing method of a light-emitting element, which is one embodiment of the present invention, will be described with reference to FIG. 1. Additionally, a light-emitting element having a tandem structure and a microcavity structure as shown in FIG. 1 (B) will also be described with reference to FIG. 1 (D). In the case where the light-emitting element shown in FIG. 1 (D) has a microcavity structure, a first electrode (101) is formed as a reflective electrode, and a second electrode (102) is formed as a semi-transparent / semi-reflective electrode. Accordingly, one or more types of desired electrode materials can be used to form a single layer or a stack. Furthermore, the second electrode (102) is formed by selecting a material as described above after forming the EL layer (103b). Additionally, sputtering or vacuum deposition methods may be used for manufacturing these electrodes.

[0178] <First electrode and second electrode>

[0179] As for the materials forming the first electrode (101) and the second electrode (102), materials described below may be appropriately combined and used as long as they satisfy the functions of both electrodes described above. For example, metals, alloys, electrically conductive compounds, and mixtures thereof may be appropriately used. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, and In-W-Zn oxide may be used. In addition, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), and neodymium (Nd), and alloys containing any of these metals in appropriate combination may be used. Furthermore, elements belonging to Group 1 or Group 2 of the periodic table not exemplified above (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing any of these metals in appropriate combination may be used, or graphene, etc.

[0180] In the light-emitting element shown in (D) of FIG. 1, when the first electrode (101) is an anode, the hole injection layer (111a) and the hole transport layer (112a) of the EL layer (103a) are sequentially stacked and formed on the first electrode (101) by vacuum deposition. After the EL layer (103a) and the charge generation layer (104) are formed, the hole injection layer (111b) and the hole transport layer (112b) of the EL layer (103b) are similarly sequentially stacked and formed on the charge generation layer (104).

[0181] Hole Injection Layer and Hole Transport Layer

[0182] The hole injection layer (111, 111a, and 111b) is a layer that injects holes into the EL layer (103, 103a, and 103b) from the first electrode (101), which is the positive electrode, or the charge generation layer (104), and is a layer containing a material with high hole injection capability.

[0183] Materials with high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. Other materials that may be used include phthalocyanine compounds such as phthalocyanine (abbreviated: H2Pc) and copper phthalocyanine (abbreviated: CuPC), aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated: DPAB) and N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated: DNTPD), or polymer compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviated: PEDOT / PSS).

[0184] Additionally, as a material with high hole injection properties, a composite material including a hole transport material and an acceptor material (electron accepting material) may be used. In this case, electrons are extracted from the hole transport material by the acceptor material, and holes are generated in the hole injection layer (111, 111a, and 111b), and holes are injected into the light-emitting layer (113, 113a, and 113b) through the hole transport layer (112, 112a, and 112b). Additionally, the hole injection layer (111, 111a, and 111b) may be formed as a single layer made of a composite material including a hole transport material and an acceptor material (electron accepting material), but may also be formed by stacking the hole transport material and the acceptor material (electron accepting material) into separate layers.

[0185] The hole transport layer (112, 112a, and 112b) is a layer that transports holes injected from the first electrode (101) or the charge generation layer (104) to the light-emitting layer (113, 113a, and 113b) by the hole injection layer (111, 111a, and 111b). Additionally, the hole transport layer (112, 112a, and 112b) is a layer comprising a hole-transporting material. It is preferable that the HOMO level of the hole-transporting material used in the hole transport layer (112, 112a, and 112b) is equal to or close to the HOMO level of the hole injection layer (111, 111a, and 111b).

[0186] As an acceptor material used in the hole injection layer (111, 111a, and 111b), oxides of metals belonging to groups 4 to 8 of the periodic table may be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide may be used. Among these, molybdenum oxide is particularly preferred because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranyl derivatives, and hexa-azatriphenylene derivatives may be used. Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated: F4-TCNQ), chloranyl, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated: HAT-CN), etc. may be used.

[0187] As a hole transportable material used in the hole injection layer (111, 111a, and 111b) and the hole transport layer (112, 112a, and 112b), the hole mobility is 10 -6 cm 2 Materials with a value greater than / Vs are preferred. Additionally, materials other than these may be used if they have higher hole transport than electron transport.

[0188] As hole-transporting materials, π-electron-excess heteroaromatic compounds (e.g., carbazole derivatives or indole derivatives) or aromatic amine compounds are preferred, and specific examples include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated: BPAFLP), and 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated: mBPAFLP). 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated: PCBA1BP), 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviated: PCPPn), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine (abbreviated: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), 4,4',4''-tris(carbazole-9-yl)triphenylamine (abbreviation: TCTA), 4,4',4''-Tris(N,N-Diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',Compounds having an aromatic amine backbone such as 4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 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), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), Compounds having a carbazole backbone such as 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophen) (abbreviation: DBT3P-II), and 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophen (abbreviation: DBTFLP-III), Examples include compounds having a thiophene backbone such as 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), compounds having a furan backbone such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).

[0189] In addition, polymer compounds such as poly(N-vinylcarbazole) (abbreviated: PVK), poly(4-vinyltriphenylamine) (abbreviated: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated: Poly-TPD) may also be used.

[0190] However, the hole transportable material is not limited to the above, and various known materials may be used in combination of one or more types for the hole injection layer (111, 111a, and 111b) and the hole transport layer (112, 112a, and 112b). Additionally, the hole transport layer (112, 112a, and 112b) may each be formed into multiple layers. That is, for example, a first hole transport layer and a second hole transport layer may be stacked.

[0191] In the light-emitting device illustrated in (D) of FIG. 1, a light-emitting layer (113a) is formed by vacuum deposition on the hole transport layer (112a) of the EL layer (103a). Additionally, after the EL layer (103a) and the charge generation layer (104) are formed, a light-emitting layer (113b) is formed by vacuum deposition on the hole transport layer (112b) of the EL layer (103b).

[0192] <Luminous layer>

[0193] The light-emitting layers (113, 113a, 113b, and 113c) are layers containing a light-emitting material. Additionally, as the light-emitting material, a material exhibiting a light-emitting color such as blue, purple, bluish-purple, green, yellowish-green, yellow, orange, or red is appropriately used. Furthermore, by using different light-emitting materials in the plurality of light-emitting layers (113a, 113b, and 113c), a configuration exhibiting different light-emitting colors (for example, white light obtained by combining light-emitting colors that are in a complementary relationship) can be achieved. Additionally, a single light-emitting layer may have a stacked structure having different light-emitting materials.

[0194] Additionally, the light-emitting layer (113, 113a, 113b, and 113c) may have one or more types of organic compounds (host material, assist material) in addition to the light-emitting material (guest material). Furthermore, as one or both types of organic compounds, one or both of the organic compound which is an embodiment of the present invention described in Embodiment 1, and the hole transport material and electron transport material described in this embodiment may be used.

[0195] As a light-emitting material that can be used in the light-emitting layer (113, 113a, 113b, and 113c), a light-emitting material that converts singlet excitation energy into light emission in the visible light region, or a light-emitting material that converts triplet excitation energy into light emission in the visible light region may be used.

[0196] In addition, other luminescent materials are, for example, as follows.

[0197] Examples of luminescent materials that convert singlet excitation energy into luminescence include fluorescent materials (fluorescent materials), such as pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, and naphthalene derivatives. Pyrene derivatives are particularly desirable due to their high luminescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated: 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviated: 1,6FrAPrn), and N,N'-bis(dibenzothiophen-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviated: 1,6ThAPrn). Examples include N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviated: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviated: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviated: 1,6BnfAPrn-03).

[0198] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviated: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviated: PAPP2BPy), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviated: 2YGAPPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPBA), Perylene, 2,5,8,11-Tetra(tert-butyl)Perylene (abbreviation: TBP), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated: 2DPAPPA), etc. can be used.

[0199] In addition, as luminescent materials that convert triplet excitation energy into luminescence, there are, for example, phosphorescent materials (phosphorescent materials) or thermally activated delayed fluorescence (TADF) materials that emit thermally activated delayed fluorescence.

[0200] Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since these materials exhibit different emission colors (emission peaks), they are appropriately selected and used as needed.

[0201] Phosphorescent materials that exhibit blue or green light and have a peak wavelength of the emission spectrum of 450 nm or more and 570 nm or less include the following materials.

[0202] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazole-3-yl-κN2]phenyl-κC}iridium(III) (abbreviated: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazoleate)iridium(III) (abbreviated: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazoleate]iridium(III) (abbreviated: [Ir(iPrptz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazoleate]iridium(III) (abbreviated: Organometallic complexes having a 4H-triazole backbone such as [Ir(iPr5btz)3]), organometallic complexes having a 1H-triazole backbone such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazoleto]iridium(III) (abbreviated: [Ir(Mptz1-mp)3]), and organometallic complexes having a 1H-triazole backbone such as tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazoleto)iridium(III) (abbreviated: [Ir(Prptz1-Me)3]), fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviated: [Ir(iPrpmi)3]), Organometallic complexes having an imidazole backbone such as tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenantridinato]iridium(III) (abbreviated: [Ir(dmpimpt-Me)3]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2']Iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]Iridium(III)picolinate (abbreviated: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2'}Iridium(III)picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2' There are organometallic complexes having phenylpyridine derivatives having electron-withdrawing groups, such as iridium(III) acetylacetonate (abbreviated: Fir(acac)), as ligands.

[0203] The following materials can be cited as phosphorescent materials that exhibit green or yellow color and have a peak wavelength of the emission spectrum between 495 nm and 590 nm.

[0204] For example, tris(4-methyl-6-phenylpyrimidineto)iridium(III) (abbreviated: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidineto)iridium(III) (abbreviated: [Ir(tBuppm)3]), (acetylacetonate)bis(6-methyl-4-phenylpyrimidineto)iridium(III) (abbreviated: [Ir(mppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidineto)iridium(III) (abbreviated: [Ir(tBuppm)2(acac)]), (acetylacetonate)bis[6-(2-norvonyl)-4-phenylpyrimidineto]iridium(III) (abbreviated: Organometallic iridium complexes having a pyrimidine backbone, such as [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviated: [Ir(mpmppm)2(acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviated: [Ir(dmppm-dmp)2(acac)]), and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviated: [Ir(dppm)2(acac)]). Organometallic iridium complexes having a pyrazine backbone, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazineto)iridium(III) (abbreviated: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazineto)iridium(III) (abbreviated: [Ir(mppr-iPr)2(acac)]), tris(2-phenylpyridineto-N,C 2' )Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinate-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,C2' )Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C 2' Organometallic iridium complexes having a pyridine backbone such as iridium(III)acetylacetonate (abbreviated: [Ir(pq)2(acac)]), [2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviated: [Ir(ppy)2(4dppy)]), and bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC], bis(2,4-diphenyl-1,3-oxazolato-N,C 2' )Iridium(III)acetylacetonate (abbreviation: [Ir(dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridinate-N,C 2'}Iridium(III)acetylacetonate (abbreviation: [Ir(p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolate-N,C 2' In addition to organometallic complexes such as iridium(III) acetylacetonate (abbreviated: [Ir(bt)2(acac)]), there are rare earth metal complexes such as tris(acetylacetonate)(monophenantroline)terbium(III) (abbreviated: [Tb(acac)3(Phen)]).

[0205] Phosphorescent materials that exhibit yellow or red color and have a peak wavelength of the emission spectrum of 570 nm or more and 750 nm or less include the following materials.

[0206] For example, organic compounds having a pyrimidine backbone, such as (diisobutyrylmetaneto)bis[4,6-bis(3-methylphenyl)pyrimidineto]iridium(III) (abbreviated: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidineto](dipivaloylmetaneto)iridium(III) (abbreviated: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidineto](dipivaloylmetaneto)iridium(III) (abbreviated: [Ir(d1npm)2(dpm)]), and tris(4-t-butyl-6-phenylpyrimidineto)iridium(III) (abbreviated: [Ir(tBuppm)3]). Metal complex, (acetylacetonato)bis(2,3,5-triphenylpyrazineto)iridium(III)(abbreviated: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazineto)(dipivaloylmetaneto)iridium(III)(abbreviated: [Ir(tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedioneto-κ 2 O,O')iridium(III)(abbreviation: [Ir(dmdppr-P)2(dibm)]), bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptaneto-κ 2 O,O')iridium(III)(abbreviation: [Ir(dmdppr-dmCP)2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalineto-N,C 2' ]Iridium(III)(abbreviation: [Ir(mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalineto-N,C 2')Iridium(III)(abbreviation: [Ir(dpq)2(acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalineto)]iridium(III)(abbreviation: [Ir(Fdpq)2(acac)]), bis{4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedioneto-κ 2 Organometallic complexes having a pyrazine skeleton such as O,O')iridium(III) (abbreviated: [Ir(dmdppr-m5CP)2(dpm)]), tris(1-phenylisoquinolinato-N,C 2' )Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2' )Iridium(III)acetylacetonate (abbreviation: [Ir(piq)2(acac)]), bis[4,6-dimethyl-2-(2-quinorinyl-κN)phenyl-κC](2,4-pentanedioneto-κ 2 There are organometallic complexes having a pyridine backbone such as O,O')iridium(III), platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated: [PtOEP]), rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedioto)(monophenantroline)europium(III) (abbreviated: [Eu(DBM)3(Phen)]), and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenantroline)europium(III) (abbreviated: [Eu(TTA)3(Phen)]).

[0207] As for the organic compounds (host materials, assist materials) used in the emitting layers (113, 113a, 113b, and 113c), it is preferable to select and use one or more types of materials having an energy gap larger than the energy gap of the emitting material (guest material). When multiple organic compounds are used in the emitting layers (113, 113a, 113b, and 113c), it is preferable to use a compound that forms an excited complex mixed with a phosphorescent emitting material. Furthermore, by adopting this configuration, luminescence can be obtained using Exciplex-Triplet Energy Transfer (ExTET), which is energy transfer from the excited complex to the emitting material. In this case, various organic compounds can be appropriately combined and used, but in order to efficiently form the excited complex, it is particularly preferable to combine a compound that readily accepts holes (hole transport material) and a compound that readily accepts electrons (electron transport material). In addition, the organic compound that is one form of the present invention described in Embodiment 1 is suitable as a compound that has a low LUMO level and readily accepts electrons.

[0208] When the emitting material is a fluorescent material, it is preferable to use an organic compound as the host material that has a large energy level in the singlet excited state and a small energy level in the triplet excited state. For example, it is preferable to use an anthracene derivative or a tetracene derivative. Specifically, 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviated: 2mBnfPPA), Examples include 9-phenyl-10-{4-(9-phenyl-9H-fluorene-9-yl)biphenyl-4'-yl}anthracene (abbreviated: FLPPA), 5,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl)tetracene, etc.

[0209] When the emitting material is a phosphorescent material, as a host material, it is preferable to select an organic compound having a triplet excitation energy greater than the triplet excitation energy of the emitting material (the energy difference between the ground state and the triplet excitation state). In particular, the organic compound of one embodiment of the present invention described in Embodiment 1 is suitable as a host material when the emitting material is a phosphorescent material because the triplet excitation state is stable. In particular, it is suitable when the phosphorescent material is red due to the triplet excitation energy level. In addition, as other examples, zinc or aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, aromatic amines, or carbazole derivatives may be used as host materials.

[0210] As a host material, more specifically, for example, the following hole transport materials and electron transport materials can be used.

[0211] Examples of host materials with high hole transportability include aromatic amine compounds such as N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated: DPA3B).

[0212] In addition, 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviated: PCzTPN2), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzPCA2), Examples of carbazole derivatives include 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated: PCzPCN1). In addition, as carbazole derivatives, in addition to those mentioned above, 4,4'-di(N-carbazolyl)biphenyl (abbreviated: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviated: TCPB), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. may be used.

[0213] In addition, as host materials with high hole transport, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated: TPD), 4,4',4''-tris(carbazole-9-yl)triphenylamine (abbreviated: TCTA), 4,4',4''-tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviated: 1-TNATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated: TDATA), and 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated: m-MTDATA), 4,4'-bis[N-(spyro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluorene-2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2-yl)amino]-9H-fluorene-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluorene-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazole-3-yl)amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazole-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N''-tris(9-phenylcarbazole-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), Aromatic amine compounds such as N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), 2-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazole-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), and N,N'-bis[4-(carbazole-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F). You can use the back. In addition, 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated: PCPN), 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviated: PCPPn), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated: PCCP), 1,3-bis(N-carbazolyl)benzene (abbreviated: mCP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated: CzTP), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviated: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviated: DBF3P-II), 1,3,5-tri(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophen (abbreviation: DBTFLP-III),Carbazole compounds such as 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and 4-[3-(triphenylene-2-yl)phenyl]dibenzothiophene (abbreviation: mDBTPTp-II), thiophene compounds, furan compounds, fluorene compounds, triphenylene compounds, phenanthrene compounds, etc., may be used.

[0214] As host materials with high electron transportability, for example, in addition to the organic compound which is one form of the present invention described in Embodiment 1, there are metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as tris(8-quinolinoleto)aluminum(III) (abbreviated: Alq), tris(4-methyl-8-quinolinoleto)aluminum(III) (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated: BeBq2), bis(2-methyl-8-quinolinoleto)(4-phenylphenolato)aluminum(III) (abbreviated: BAlq), and bis(8-quinolinoleto)zinc(II) (abbreviated: Znq). In addition, metal complexes having oxazole-based or thiazole-based ligands, such as bis[2-(2-benzoxazolyl)phenolate]zinc(II) (abbreviated: ZnPBO) and bis[2-(2-benzothiazolyl)phenolate]zinc(II) (abbreviated: ZnBTZ), may also be used. In addition, in addition to metal complexes, oxadiazole derivatives such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated: OXD-7), and 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated: CO11), or triazole derivatives such as 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated: TAZ), Compounds having an imidazole backbone such as 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) and 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) (especially benzimidazole derivatives), or compounds having an oxazole backbone such as 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs) (especially benzoxazole derivatives), or vasofenanthroline (abbreviation: Bphen), vasocuproin (abbreviation: BCP), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,Phenanthroline derivatives such as 10-phenanthroline (abbreviation: NBphen), or 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-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), Heterocyclic compounds having a diazine backbone, such as 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated: 6mDBTPDBq-II), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviated: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviated: 4,6mDBTP2Pm-II), and 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviated: 4,6mCzP2Pm), or Heterocyclic compounds having a triazine backbone, such as 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) and 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), or heterocyclic compounds having a pyridine backbone, such as 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), may also be used. Also, poly(2,5-pyridinediyl) (abbreviated: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,Polymer compounds such as 6'-diyl (abbreviated: PF-BPy) may also be used.

[0215] In addition, condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives may be used as host materials, and specifically, 9,10-diphenylanthracene (abbreviated: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviated: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated: PCAPBA), 2PCAPA, 6,12-dimethoxy-5,11-diphenylchrysene, DBC1, 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-biantrile (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), etc. can be used.

[0216] In addition, when multiple organic compounds are used in the light-emitting layer (113, 113a, 113b, and 113c), two types of compounds (a first compound and a second compound) that form an excited complex may be mixed and used with an organometallic complex. In this case, various organic compounds may be appropriately combined and used, but in order to efficiently form the excited complex, it is particularly desirable to combine a compound that readily accepts holes (hole transport material) and a compound that readily accepts electrons (electron transport material). Furthermore, as the hole transport material and the electron transport material, the materials specifically described in this embodiment may be used. With this configuration, high efficiency, low voltage, and long lifespan can be realized simultaneously.

[0217] A TADF material refers to a material capable of up-converting (crossing between inverse terms) from a triplet excited state to a singlet excited state by a small amount of thermal energy, and efficiently exhibiting luminescence (fluorescence) from the singlet excited state. Furthermore, conditions for efficiently obtaining thermally activated delayed fluorescence include an energy difference between the energy levels of the triplet excited state and the singlet excited state being 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Additionally, delayed fluorescence in TADF materials refers to luminescence that has a significantly longer lifetime while possessing a spectrum similar to general fluorescence. Its lifetime is 10 -6 At least 10 seconds, preferably 10 -3 It is more than a second.

[0218] Examples of TADF materials include fullerene or its derivatives, acridin derivatives such as proflavin, eosin, etc. In addition, metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be used. Examples of metal-containing porphyrins include, for instance, protoporphyrin-tin fluoride complex (abbreviated: SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (abbreviated: SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (abbreviated: SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviated: SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviated: SnF2(OEP)), ethioporphyrin-tin fluoride complex (abbreviated: SnF2(Etio I)), octaethylporphyrin-platinum chloride complex (abbreviated: PtCl2OEP), etc.

[0219] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviated: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviated: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazine (abbreviated: Heterocyclic compounds having π-electron excess heterocyclic rings and π-electron deficient heterocyclic rings, such as 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), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), can be used. In addition, a material in which a π-electron-excess heterocyclic ring and a π-electron-deficient heterocyclic ring are directly bonded is particularly desirable because both the donor nature of the π-electron-excess heterocyclic ring and the acceptor nature of the π-electron-deficient heterocyclic ring are strengthened, thereby reducing the energy difference between the singlet excited state and the triplet excited state.

[0220] In addition, when using TADF materials, they may also be used in combination with other organic compounds. In particular, it is preferable to use an organic compound, which is one form of the present invention described in Embodiment 1, as a host material for a TADF material that can be combined with the aforementioned host material, hole transport material, and electron transport material.

[0221] In the light-emitting element illustrated in (D) of FIG. 1, an electron transport layer (114a) is formed on the light-emitting layer (113a) of the EL layer (103a) by vacuum deposition. Additionally, after the EL layer (103a) and the charge generation layer (104) are formed, an electron transport layer (114b) is formed on the light-emitting layer (113b) of the EL layer (103b) by vacuum deposition.

[0222] Electron transport layer

[0223] The electron transport layer (114, 114a, and 114b) is a layer that transports electrons injected from the second electrode (102) or the charge generation layer (104) by the electron injection layer (115, 115a, and 115b) to the light-emitting layer (113, 113a, 113b). Additionally, the electron transport layer (114, 114a, and 114b) is a layer comprising an electron transportable material. The electron transportable material used in the electron transport layer (114, 114a, and 114b) is 1×10 -6 cm 2 A material having an electron mobility of / Vs or higher is preferred. Additionally, other materials may be used as long as they have higher electron transportability than holes. Furthermore, the organic compound, which is one form of the present invention described in Embodiment 1, can also be used as an electron transport layer because it has excellent electron transportability.

[0224] Examples of electron transport materials include metal complexes having quinoline ligands, benzoquinoline ligands, oxazole ligands, or thiazole ligands, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, pyridine derivatives, bipyridine derivatives, etc. In addition, π-electron deficient heteroaromatic compounds, such as nitrogen-containing heteroaromatic compounds, may be used.

[0225] Specifically, metal complexes such as Alq3, tris(4-methyl-8-quinolinolenate)aluminum(III) (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated: BeBq2), BAlq, bis[2-(2-hydroxyphenyl)benzoxazolato]zinc(II) (abbreviated: Zn(BOX)2), bis[2-(2-hydroxyphenyl)benzothiazolate]zinc(II) (abbreviated: Zn(BTZ)2), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated: PBD), Heteroaromatic compounds such as OXD-7,3-(4'-tert-butylphenyl)-4-phenyl―5-(4''-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), vasophenanthroline (abbreviation: Bphen), vasocuproin (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), Quinoxaline or dibenzoquinoxaline derivatives such as 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated: 2mDBTBPDBq-II), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated: 6mDBTPDBq-II) may be used.

[0226] In addition, polymer compounds such as poly(2,5-pyridinediyl) (abbreviated: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated: PF-BPy) may also be used.

[0227] In addition, the electron transport layer (114, 114a, and 114b) may be a single layer, or a structure in which two or more layers made of the material are stacked.

[0228] In the light-emitting device illustrated in (D) of FIG. 1, an electron injection layer (115a) is formed on the electron transport layer (114a) of the EL layer (103a) by vacuum deposition. After that, the EL layer (103a) and the charge generation layer (104) are formed, and after the electron transport layer (114b) of the EL layer (103b) is formed, an electron injection layer (115b) is formed on top of it by vacuum deposition.

[0229] Electron injection layer

[0230] The electron injection layer (115, 115a, and 115b) is a layer containing a material with high electron injection properties. The electron injection layer (115, 115a, and 115b) contains lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiO2). x Alkali metals, alkaline earth metals, or compounds thereof such as ) may be used. Additionally, rare earth metal compounds such as erbium fluoride (ErF3) may be used. Furthermore, an electride may be used in the electron injection layer (115, 115a, and 115b). Examples of electrides include, for instance, a material in which electrons are added at a high concentration to a mixed oxide of calcium and aluminum. Additionally, the material constituting the electron transport layer (114, 114a, and 114b) described above may be used.

[0231] In addition, a composite material formed by mixing an organic compound and an electron donor (donor) may be used in the electron injection layer (115, 115a, and 115b). Since electrons are generated in the organic compound by the electron donor, such a composite material has excellent electron injection and electron transport properties. In this case, as the organic compound, it is preferable that the material has excellent transport of the generated electrons, and specifically, for example, an electron transport material (such as a metal complex or a heteroaromatic compound) used in the electron transport layer (114, 114a, 114b) described above may be used. As the electron donor, it is preferable that the material exhibits electron-donating properties with respect to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides or alkaline earth metal oxides are preferred, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, Lewis bases such as magnesium oxide may be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated: TTF) may also be used.

[0232] Additionally, for example, when amplifying light obtained from the light-emitting layer (113b), it is preferable that the optical distance between the second electrode (102) and the light-emitting layer (113b) be less than 1 / 4 of the wavelength λ of the light emitted by the light-emitting layer (113b). In this case, the optical distance can be adjusted by changing the thickness of the electron transport layer (114b) or the electron injection layer (115b).

[0233] Charge generation layer

[0234] The charge generation layer (104) has the function of injecting electrons into the EL layer (103a) and injecting holes into the EL layer (103b) when a voltage is applied between the first electrode (anode) (101) and the second electrode (negative electrode) (102). Additionally, the charge generation layer (104) may be configured such that an electron acceptor is added to a hole-transporting material, or an electron donor is added to an electron-transporting material. Additionally, both of these configurations may be stacked. Furthermore, by forming the charge generation layer (104) using the above-described material, the increase in driving voltage when the EL layer is stacked can be suppressed.

[0235] In the charge generation layer (104), when the configuration is such that an electron acceptor is added to a hole-transporting material, the material described in this embodiment may be used as the hole-transporting material. In addition, examples of electron acceptors include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated: F4-TCNQ), chloranyl, etc. In addition, oxides of metals belonging to groups 4 to 8 of the periodic table may be used. Specifically, examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc.

[0236] In the charge generation layer (104), when the electron donor is added to the electron transport material, the material described in this embodiment may be used as the electron transport material. Additionally, as the electron donor, alkali metals, alkaline earth metals, rare earth metals, or metals belonging to groups 2 and 13 of the periodic table, as well as their oxides and carbonates, may be used. Specifically, it is preferable to use lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, etc. Additionally, organic compounds such as tetracyanaptacene may be used as the electron donor.

[0237] In addition, the EL layer (103c) of (E) in FIG. 1 may be configured in the same way as the EL layers (103, 103a, and 103b) described above. In addition, the charge generating layers (104a and 104b) may also be configured in the same way as the charge generating layer (104) described above.

[0238] <Circuit Board>

[0239] The light-emitting element described in this embodiment can be formed on various substrates. In addition, the type of substrate is not limited to a specific one. Examples of substrates include semiconductor substrates (e.g., single-crystal substrates or silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates, metal substrates, stainless steel substrates, substrates having stainless steel foil, tungsten substrates, substrates having tungsten foil, flexible substrates, bonding films, paper containing fibrous materials, or substrate films.

[0240] In addition, examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, or soda-lime glass. In addition, examples of flexible substrates, bonding films, and substrate films include plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), synthetic resins such as acrylic, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid, epoxy, inorganic deposition films, or paper.

[0241] In addition, vacuum processes such as deposition methods or solution processes such as spin coating or inkjet methods may be used for fabricating the light-emitting device described in this embodiment. When using a deposition method, physical vapor deposition (PVD) methods such as sputtering, ion plating, ion beam deposition, molecular beam deposition, and vacuum deposition, or chemical vapor deposition (CVD) methods may be used. In particular, the functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a, 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114, 114a, 114b), electron injection layer (115, 115a, 115b), and charge generation layer (104, 104a, 104b)) included in the EL layer of the light-emitting device can be formed by a deposition method (vacuum deposition method, etc.), a coating method (dip coating method, die coating method, bar coating method, spin coating method, spray coating method, etc.), a printing method (inkjet method, screen printing method, offset printing method, flexographic printing method, gravure method, micro contact printing method, etc.).

[0242] In addition, each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a, 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114, 114a, 114b), electron injection layer (115, 115a, 115b) or charge generation layer (104, 104a, 104b)) constituting the EL layer (103, 103a, 103b) of the light-emitting element described in this embodiment is not limited to the materials described above, and materials other than the materials described above may be used in combination as long as they can satisfy the function of each layer. For example, polymer compounds (oligomers, dendrimers, polymers, etc.), medium-molecular compounds (compounds in the intermediate range between low-molecular and high-molecular weights: molecular weight 400 to 4000), inorganic compounds (quantum dot materials, etc.) can be used. In addition, as quantum dot materials, colloidal quantum dot materials, alloy-type quantum dot materials, core-shell type quantum dot materials, core-type quantum dot materials, etc. can be used.

[0243] The configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0244] (Embodiment 3)

[0245] In this embodiment, a light-emitting device that is one form of the present invention is described. In addition, the light-emitting device shown in FIG. 2 (A) is an active matrix type light-emitting device in which a transistor (FET) (202) on a first substrate (201) and light-emitting elements (203R, 203G, 203B, and 203W) are electrically connected, and a plurality of light-emitting elements (203R, 203G, 203B, and 203W) have a common EL layer (204) and have a microcavity structure in which the optical distance between the electrodes of each light-emitting element is adjusted according to the light emission color of each light-emitting element. In addition, it is a top emission type light-emitting device in which light obtained from the EL layer (204) is emitted through a color filter (206R, 206G, and 206B) formed on a second substrate (205).

[0246] The light-emitting device illustrated in (A) of FIG. 2 is formed such that the first electrode (207) functions as a reflective electrode. Additionally, the second electrode (208) is formed such that it functions as a semi-transparent / semi-reflective electrode. Furthermore, the electrode material forming the first electrode (207) and the second electrode (208) may be appropriately used by referring to the description of other embodiments.

[0247] In addition, in (A) of FIG. 2, for example, when the light-emitting element (203R) is a red light-emitting element, the light-emitting element (203G) is a green light-emitting element, the light-emitting element (203B) is a blue light-emitting element, and the light-emitting element (203W) is a white light-emitting element, as shown in (B) of FIG. 2, the light-emitting element (203R) is adjusted so that the distance between the first electrode (207) and the second electrode (208) becomes an optical distance (200R), the light-emitting element (203G) is adjusted so that the distance between the first electrode (207) and the second electrode (208) becomes an optical distance (200G), and the light-emitting element (203B) is adjusted so that the distance between the first electrode (207) and the second electrode (208) becomes an optical distance (200B). Additionally, as shown in (B) of FIG. 2, optical adjustment can be performed by stacking a conductive layer (210R) on the first electrode (207) in the light-emitting element (203R) and stacking a conductive layer (210G) in the light-emitting element (203G).

[0248] Color filters (206R, 206G, and 206B) are formed on the second substrate (205). Additionally, a color filter is a filter that transmits light in a specific wavelength range among visible light and blocks light in a specific wavelength range. Accordingly, as shown in (A) of FIG. 2, by providing a color filter (206R) that transmits only light in a red wavelength range at a position overlapping with the light-emitting element (203R), red light emission can be obtained from the light-emitting element (203R). Additionally, by providing a color filter (206G) that transmits only light in a green wavelength range at a position overlapping with the light-emitting element (203G), green light emission can be obtained from the light-emitting element (203G). Additionally, by providing a color filter (206B) that transmits only light in a blue wavelength range at a position overlapping with the light-emitting element (203B), blue light emission can be obtained from the light-emitting element (203B). However, the light-emitting element (203W) can obtain white light emission even without providing a color filter. Additionally, a black layer (black matrix) (209) may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, and 206B) and the black layer (209) may be covered with an overcoat layer made of a transparent material.

[0249] Although FIG. 2 (A) illustrates a light-emitting device with a structure (top emission type) that extracts light toward the second substrate (205), it may also be a light-emitting device with a structure (bottom emission type) that extracts light toward the first substrate (201) where the FET (202) is formed, as shown in FIG. 2 (C). In addition, in the case of a bottom emission type light-emitting device, the first electrode (207) is formed to function as a semi-transparent / semi-reflective electrode, and the second electrode (208) is formed to function as a reflective electrode. In addition, at least a transparent substrate is used for the first substrate (201). In addition, color filters (206R', 206G', and 206B') may be provided toward the first substrate (201) side rather than the light-emitting elements (203R, 203G, and 203B), as shown in FIG. 2 (C).

[0250] In addition, although (A) of FIG. 2 describes cases where the light-emitting element is a red light-emitting element, a green light-emitting element, a blue light-emitting element, or a white light-emitting element, the light-emitting element of one embodiment of the present invention is not limited to such configurations and may have a configuration having a yellow light-emitting element or an orange light-emitting element. Furthermore, regarding the material used for the EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer, etc.) to manufacture these light-emitting elements, it may be appropriately used by referring to the description of other embodiments. In addition, in such cases, it is necessary to appropriately select a color filter according to the light-emitting color of the light-emitting element.

[0251] By configuring as described above, a light-emitting device having a light-emitting element that emits a plurality of light-emitting colors can be obtained.

[0252] In addition, the configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0253] (Embodiment 4)

[0254] In this embodiment, a light-emitting device, which is one form of the present invention, is described.

[0255] By applying the device configuration of a light-emitting element, which is one embodiment of the present invention, an active matrix type light-emitting device or a passive matrix type light-emitting device can be manufactured. Furthermore, the active matrix type light-emitting device has a configuration combining a light-emitting element and a transistor (FET). Accordingly, both the passive matrix type light-emitting device and the active matrix type light-emitting device are included in one embodiment of the present invention. Additionally, the light-emitting element described in other embodiments may be applied to the light-emitting device described in this embodiment.

[0256] In this embodiment, an active matrix type light-emitting device is described with reference to FIG. 3.

[0257] Additionally, FIG. 3 (A) is a top view illustrating a light-emitting device, and FIG. 3 (B) is a cross-sectional view of FIG. 3 (A) taken along the dashed line A-A'. The active matrix type light-emitting device has a pixel portion (302), a driving circuit portion (source line driving circuit) (303), and a driving circuit portion (gate line driving circuit) (304a, 304b) provided on a first substrate (301). The pixel portion (302) and the driving circuit portions (303, 304a, and 304b) are sealed between the first substrate (301) and the second substrate (306) by means of a real (305).

[0258] Additionally, lead wiring (307) is provided on the first substrate (301). The lead wiring (307) is connected to an external input terminal, an FPC (308). Additionally, the FPC (308) transmits signals (e.g., video signals, clock signals, start signals, reset signals, etc.) or potentials from the outside to the driving circuit portions (303, 304a, and 304b). Additionally, a printed circuit board (PWB) may be provided on the FPC (308). Additionally, the state in which these FPCs or PWBs are provided falls within the category of a light-emitting device.

[0259] Next, the cross-sectional structure is shown in (B) of Fig. 3.

[0260] The pixel portion (302) is formed by a plurality of pixels having an FET (switching FET) (311), an FET (current control FET) (312), and a first electrode (313) electrically connected to the FET (312). Additionally, the number of FETs in each pixel is not particularly limited and can be provided appropriately as needed.

[0261] The FETs (309, 310, 311, and 312) are not specifically limited and, for example, transistors such as staggered or reverse staggered types may be used. In addition, transistor structures such as top gate type or bottom gate type may also be used.

[0262] In addition, the crystallinity of the semiconductor that can be used for these FETs (309, 310, 311, and 312) is not particularly limited, and any of the amorphous semiconductor or a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single-crystal semiconductor, or a semiconductor having a crystalline region in part) may be used. In addition, it is desirable to use a crystalline semiconductor so that the degradation of transistor characteristics can be suppressed.

[0263] In addition, as these semiconductors, examples include Group 14 elements, compound semiconductors, oxide semiconductors, and organic semiconductors. Representative examples include semiconductors containing silicon, semiconductors containing gallium arsenide, and oxide semiconductors containing indium.

[0264] The driving circuit section (303) has an FET (309) and an FET (310). Additionally, the FET (309) and the FET (310) may be formed as a circuit including a unipolar transistor (only one of N-type and P-type), or as a CMOS circuit including an N-type transistor and a P-type transistor. Additionally, it may be configured to have an external driving circuit.

[0265] The end of the first electrode (313) is covered with an insulating material (314). Additionally, the insulating material (314) may be an organic compound such as a negative-type photosensitive resin or a positive-type photosensitive resin (acrylic resin), or an inorganic compound such as silicon oxide, silicon nitride oxide, or silicon nitride. It is preferable that a curved surface having curvature be formed on the upper or lower part of the insulating material (314). This allows the coverage of the film formed on the insulating material (314) to be good.

[0266] An EL layer (315) and a second electrode (316) are laminated on the first electrode (313). The EL layer (315) has a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc.

[0267] In addition, the configuration of the light-emitting element (317) described in this embodiment may be configured or materials described in other embodiments. Also, although not shown here, the second electrode (316) is electrically connected to an external input terminal, the FPC (308).

[0268] In addition, although only one light-emitting element (317) is shown in the cross-sectional view illustrated in FIG. 3 (B), a plurality of light-emitting elements are arranged in a matrix within the pixel portion (302). By selectively forming light-emitting elements that produce three types of light (R, G, B) in the pixel portion (302), a light-emitting device capable of full-color display can be formed. Furthermore, the light-emitting element is not limited to those producing three types of light (R, G, B); for example, light-emitting elements producing white (W), yellow (Y), magenta (M), cyan (C), etc., may also be formed. For example, by adding the light-emitting elements producing various types of light as described above to the light-emitting elements producing three types of light (R, G, B), effects such as improved color purity and reduced power consumption can be obtained. Additionally, the light-emitting device capable of full-color display may be formed by combining it with a color filter. In addition, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), etc. can be used as types of color filters.

[0269] FETs (309, 310, 311, and 312) or light-emitting elements (317) on the first substrate (301) are provided in a space (318) surrounded by the first substrate (301), the second substrate (306), and the actual material (305) by joining the second substrate (306) and the first substrate (301) by the actual material (305). Additionally, the space (318) may be filled with an inert gas (such as nitrogen or argon) or an organic material (including the actual material (305)).

[0270] In the actual material (305), an epoxy resin or glass frit may be used. Additionally, it is preferable to use a material that does not allow moisture or oxygen to pass through as much as possible in the actual material (305). Furthermore, the second substrate (306) may be any material that can be used for the first substrate (301). Thus, various substrates described in other embodiments may be appropriately used. As for the substrate, in addition to glass substrates or quartz substrates, plastic substrates made of FRP (Fiber-Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, or acrylic may be used. When glass frit is used as the actual material, it is preferable that the first substrate (301) and the second substrate (306) be glass substrates in terms of adhesion.

[0271] Thus, an active matrix type light-emitting device can be obtained.

[0272] In addition, when forming an active matrix type light-emitting device on a flexible substrate, the FET and light-emitting element may be formed directly on the flexible substrate, but the FET and light-emitting element may also be formed on another substrate having a release layer, and then the FET and light-emitting element may be peeled off from the release layer and transferred to the flexible substrate by applying heat, force, or laser irradiation. In addition, as the release layer, for example, an inorganic film laminate of a tungsten film and a silicon oxide film, or an organic resin film such as polyimide, may be used. In addition, as a flexible substrate, in addition to a substrate capable of forming a transistor, examples include a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a fabric substrate (including natural fibers (silk, cotton, hemp), synthetic fibers (nylon, polyurethane, polyester), or recycled fibers (acetate, cupro, rayon, recycled polyester), etc.), a leather substrate, or a rubber substrate. By using these substrates, durability and heat resistance are improved, and lightweighting and thinning can be achieved.

[0273] In addition, the configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0274] (Embodiment 5)

[0275] In this embodiment, examples of various electronic devices or automobiles completed by applying a light-emitting device, which is one form of the present invention, and a display device having a light-emitting element, which is one form of the present invention, will be described.

[0276] The electronic device illustrated in FIG. 4 (A) to (E) may have a housing (7000), a display unit (7001), a speaker (7003), an LED lamp (7004), an operation key (7005) (including a power switch or an operation switch), a connection terminal (7006), a sensor (7007) (including a function to measure force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, longitude, electric field, current, voltage, power, radiation, flow rate, humidity, inclination, vibration, smell, or infrared radiation), a microphone (7008), etc.

[0277] Figure 4 (A) illustrates a mobile computer and may have a switch (7009) and an infrared port (7010), etc., in addition to what is described above.

[0278] Figure 4 (B) illustrates a portable image playback device (e.g., a DVD player) having a recording medium, and may have a second display unit (7002), a recording medium reader (7011), etc. in addition to what is described above.

[0279] Figure 4 (C) illustrates a goggle-type display and may have a second display part (7002), a support part (7012), an earphone (7013), etc. in addition to the above.

[0280] Figure 4 (D) illustrates a digital camera having a television receiving function, and in addition to the above, it may have an antenna (7014), a shutter button (7015), a receiving unit (7016), etc.

[0281] Figure 4 (E) illustrates a mobile phone (including a smartphone) and may have a display unit (7001), a microphone (7019), a speaker (7003), a camera (7020), an external connection unit (7021), an operation button (7022), etc. in a housing (7000).

[0282] Figure 4 (F) illustrates a large television device (also referred to as a television or television receiver) and may include a housing (7000), a display unit (7001), etc. In addition, the configuration shown here is one in which the housing (7000) is supported by a stand (7018). In addition, the operation of the television device may be performed by a separate remote controller (7111), etc. In addition, the display unit (7001) may have a touch sensor, or the display unit (7001) may be operated by touching it with a finger, etc. The remote controller (7111) may have a display unit that displays information output from the remote controller (7111). Channels can be operated and volume adjusted by the operation keys or touch panel of the remote controller (7111), and images displayed on the display unit (7001) can be operated.

[0283] The electronic devices illustrated in FIGS. 4 (A) to (F) may have various functions. For example, they may have a function to display various information (still images, video, text images, etc.) on a display unit, a touch panel function, a function to display a calendar, date or time, a function to control processing by various software (programs), a wireless communication function, a function to connect to various computer networks using the wireless communication function, a function to transmit and receive various data using the wireless communication function, and a function to read programs or data recorded on a recording medium and display them on a display unit. In addition, an electronic device having multiple display units may have a function to mainly display image information on one display unit and mainly display text information on another display unit, or a function to display a three-dimensional image by displaying an image that takes parallax into account on multiple display units. In addition, an electronic device having a receiving unit may have a function to capture a still image, a function to capture a video, a function to automatically or manually correct the captured image, a function to save the captured image to a recording medium (external or built into the camera), and a function to display the captured image on a display unit. In addition, the functions that the electronic devices illustrated in (A) to (F) of FIG. 4 may have are not limited to these, and may have various functions.

[0284] Figure 4 (G) illustrates a smart watch and has a housing (7000), a display unit (7001), operation buttons (7022 and 7023), a connection terminal (7024), a band (7025), a buckle (7026), etc.

[0285] A display unit (7001) mounted on a housing (7000) that also serves as a bezel has a non-rectangular display area. The display unit (7001) can display an icon (7027) indicating time, other icons (7028), etc. Additionally, the display unit (7001) may be a touch panel (input / output device) equipped with a touch sensor (input device).

[0286] In addition, the smart watch illustrated in (G) of FIG. 4 may have various functions. For example, it may have a function to display various information (still images, videos, text images, etc.) on the display unit, a touch panel function, a function to display a calendar, date or time, a function to control processing by various software (programs), a wireless communication function, a function to connect to various computer networks using the wireless communication function, a function to transmit and receive various data using the wireless communication function, and a function to read programs or data recorded on a recording medium and display them on the display unit.

[0287] Additionally, the housing (7000) may have a speaker, a sensor (including a function to measure force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, longitude, electric field, current, voltage, power, radiation, flow rate, humidity, inclination, vibration, smell, or infrared), a microphone, etc.

[0288] In addition, a light-emitting device and a display device having a light-emitting element, which are embodiments of the present invention, can be used in each display part of the electronic device described in the present embodiment, thereby enabling the realization of an electronic device with a long lifespan.

[0289] Additionally, as an electronic device to which a light-emitting device is applied, a foldable portable information terminal illustrated in FIG. 5 (A) to (C) can be cited. FIG. 5 (A) illustrates a portable information terminal (9310) in an unfolded state. FIG. 5 (B) illustrates a portable information terminal (9310) in a state that is in the middle of changing from an unfolded state to a folded state, or vice versa. FIG. 5 (C) illustrates a portable information terminal (9310) in a folded state. The portable information terminal (9310) in a folded state has excellent portability, and the portable information terminal (9310) in an unfolded state has a wide, seamless display area, so the visibility of the display is excellent.

[0290] The display unit (9311) is supported by three housings (9315) connected by a hinge (9313). Additionally, the display unit (9311) may be a touch panel (input / output device) equipped with a touch sensor (input device). Furthermore, by using the hinge (9313) to bend the two housings (9315) together, the display unit (9311) can reversibly deform the portable information terminal (9310) from an unfolded state to a folded state. Additionally, a light-emitting device of one form of the present invention may be used in the display unit (9311). Furthermore, a long-life electronic device can be realized. The display area (9312) of the display unit (9311) is a display area located on the side when the portable information terminal (9310) is in a folded state. The display area (9312) can display information icons or shortcuts for frequently used applications and programs, etc., so that information can be checked and applications can be launched smoothly.

[0291] Additionally, a vehicle equipped with a light-emitting device is illustrated in FIGS. 6 (A) and (B). That is, the light-emitting device can be provided as an integral part of the vehicle. Specifically, it can be applied to the light (5101) (including the rear part of the vehicle body) on the exterior of the vehicle (as shown in FIG. 6 (A)), the wheel (5102) of the tire, part or all of the door (5103), etc. Additionally, it can be applied to the display part (5104), steering wheel (5105), shift lever (5106), seat (5107), inner rearview mirror (5108), etc. on the interior of the vehicle (as shown in FIG. 6 (B)). Furthermore, it may be applied to part of the window.

[0292] Thus, an electronic device or automobile equipped with a light-emitting device or a display device, which is one embodiment of the present invention, can be obtained. In addition, in such cases, an electronic device with a long lifespan can be realized. Furthermore, the electronic device or automobile to which it can be applied is not limited to those described in this embodiment, but can be applied in various fields.

[0293] In addition, the configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0294] (Embodiment 6)

[0295] In this embodiment, the configuration of a lighting device manufactured by applying a light-emitting device, which is one form of the present invention, or a light-emitting element, which is a part thereof, will be explained with reference to FIG. 7.

[0296] Figures 7 (A) to (D) illustrate examples of cross-sectional views of lighting devices. Additionally, Figures 7 (A) and (B) illustrate a bottom-emission type lighting device that extracts light toward a substrate, and Figures 7 (C) and (D) illustrate a top-emission type lighting device that extracts light toward a sealed substrate.

[0297] The lighting device (4000) illustrated in FIG. 7 (A) has a light-emitting element (4002) on a substrate (4001). Additionally, on the outer side of the substrate (4001), there is a substrate (4003) having irregularities. The light-emitting element (4002) has a first electrode (4004), an EL layer (4005), and a second electrode (4006).

[0298] The first electrode (4004) is electrically connected to the electrode (4007), and the second electrode (4006) is electrically connected to the electrode (4008). Additionally, an auxiliary wiring (4009) electrically connected to the first electrode (4004) may be provided. Additionally, an insulating layer (4010) is formed on the auxiliary wiring (4009).

[0299] Additionally, the substrate (4001) and the sealing substrate (4011) are bonded together with a real material (4012). Additionally, it is preferable to provide a desiccant (4013) between the sealing substrate (4011) and the light-emitting element (4002). Furthermore, since the substrate (4003) has irregularities such as (A) in FIG. 7, the extraction efficiency of light generated from the light-emitting element (4002) can be improved.

[0300] In addition, instead of the substrate (4003), a diffuser plate (4015) may be provided on the outside of the substrate (4001), such as the lighting device (4100) shown in (B) of FIG. 7.

[0301] The lighting device (4200) illustrated in (C) of FIG. 7 has a light-emitting element (4202) on a substrate (4201). The light-emitting element (4202) has a first electrode (4204), an EL layer (4205), and a second electrode (4206).

[0302] The first electrode (4204) is electrically connected to the electrode (4207), and the second electrode (4206) is electrically connected to the electrode (4208). Additionally, an auxiliary wiring (4209) electrically connected to the second electrode (4206) may be provided. Additionally, an insulating layer (4210) may be provided below the auxiliary wiring (4209).

[0303] A substrate (4201) and a sealing substrate (4211) having irregularities are bonded together with an actual material (4212). Additionally, a barrier film (4213) and a planarization film (4214) may be provided between the sealing substrate (4211) and the light-emitting element (4202). Furthermore, since the sealing substrate (4211) has irregularities such as (C) of FIG. 7, the extraction efficiency of light generated from the light-emitting element (4202) can be improved.

[0304] In addition, instead of a sealed substrate (4211), a diffuser plate (4215) may be provided on the light-emitting element (4202), such as the lighting device (4300) shown in (D) of FIG. 7.

[0305] In addition, as described in the present embodiment, by applying a light-emitting device which is one form of the present invention, or a light-emitting element which is a part thereof, a lighting device having a desired color can be provided.

[0306] In addition, the configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0307] (Embodiment 7)

[0308] In this embodiment, an application example of a lighting device manufactured by applying a light-emitting device, which is one form of the present invention, or a light-emitting element, which is a part thereof, will be described with reference to FIG. 8.

[0309] As an indoor lighting device, it can be applied as a ceiling light (8001). The ceiling light (8001) can be a ceiling-mounted type or a ceiling-recessed type. In addition, such a lighting device is constructed by combining a light-emitting device with a housing or cover. Furthermore, it can also be applied as a cord pendant type (a method of suspending from the ceiling with a cord).

[0310] In addition, the footlight (8002) can increase safety underfoot by illuminating the floor. For example, it is effective to use it in bedrooms, stairs, or passageways. In that case, the size or shape can be appropriately changed according to the area or structure of the room. In addition, it can be made into a stationary lighting device composed of a light-emitting device and a support.

[0311] In addition, the sheet-type lighting (8003) is a thin sheet-type lighting device. Since it is attached to a wall, it does not take up space and can be used for a wide range of applications. It is also easy to make it large. It can also be used on curved walls or housings.

[0312] In addition, a lighting device (8004) that controls light from a light source only in the desired direction may also be used.

[0313] In addition to the above, by applying a light-emitting device, which is one form of the present invention, or a light-emitting element, which is a part thereof, to a part of furniture installed indoors, it can be made into a lighting device that functions as furniture.

[0314] As described above, various lighting devices incorporating a light-emitting device can be obtained. Furthermore, these lighting devices are included in one embodiment of the present invention.

[0315] In addition, the configuration described in this embodiment can be used in appropriate combination with the configuration described in other embodiments.

[0316] (Example 1)

[0317] <<Synthesized Example 1>>

[0318] In this embodiment, a method for synthesizing the organic compound 9-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mDBtBPNfpr), which is one form of the present invention represented by the structural formula (100) of Embodiment 1, is described. Additionally, the structure of 9mDBtBPNfpr is shown below.

[0319] [Chemical Formula 40]

[0320]

[0321] <Step 1: Synthesis of 6-chloro-3-(2-methoxynaphthalene-1-yl)pyrazine-2-amine>

[0322] First, 4.37 g of 3-bromo-6-chloropyrazine-2-amine, 4.23 g of 2-methoxynaphthalene-1-boronic acid, 4.14 g of potassium fluoride, and 75 mL of dehydrated tetrahydrofuran were placed in a 3-neck flask equipped with a reflux tube, and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 0.57 g of tris(dibenzylideneacetone)dipalladium (O) (abbreviated: Pd2(dba)3) and 4.5 mL of tri-tert-butylphosphine (abbreviated: P(tBu)3) were added, and the mixture was reacted by stirring at 80°C for 54 hours.

[0323] After a predetermined amount of time had elapsed, the obtained mixture was filtered by suction and the filtrate was concentrated. Subsequently, the mixture was purified by silica gel column chromatography using toluene:ethyl acetate = 9:1 as the developing solvent to obtain the desired pyrazine derivative (yellowish-white powder, quantity 2.19 g, yield 36%). The synthesis scheme of Step 1 is shown in the following formula (a-1).

[0324] [Chemical Formula 41]

[0325]

[0326] <Step 2: Synthesis of 9-Chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine>

[0327] Next, 2.18 g of 6-chloro-3-(2-methoxynaphthalene-1-yl)pyrazine-2-amine obtained in Step 1, 63 mL of dehydrated tetrahydrofuran, and 84 mL of glacial acetic acid were placed in a three-necked flask, and the interior was purged with nitrogen. After cooling the flask to -10°C, 2.8 mL of tert-butyl nitrite was added dropwise, and the mixture was stirred for 30 minutes at -10°C and for 3 hours at 0°C. After the specified time had elapsed, 250 mL of water was added to the resulting suspension and suction filtration was performed to obtain the desired pyrazine derivative (yellowish-white powder, quantity 1.48 g, yield 77%). The synthesis scheme for Step 2 is shown in the following formula (a-2).

[0328] [Chemical Formula 42]

[0329]

[0330] <Step 3: Synthesis of 9-[(3'-Dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mDBtBPNfpr)>

[0331] In addition, 1.48 g of 9-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine obtained in Step 2 above, 3.41 g of 3'-(4-dibenzothiophen)-1,1'-biphenyl-3-boronic acid, 8.8 mL of 2 M aqueous potassium carbonate solution, 100 mL of toluene, and 10 mL of ethanol were placed in a three-necked flask, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.84 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviated: Pd(PPh3)2Cl2) was added, and the mixture was reacted by stirring at 80°C for 18 hours.

[0332] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using a mixed solvent of toluene and hexane to obtain the target product (pale yellow solid, quantity 2.66 g, yield 82%).

[0333] The obtained pale yellow solid 2.64 g was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 315°C while flowing argon gas at a flow rate of 15 mL / min under a pressure of 2.6 Pa. After sublimation purification, the target pale yellow solid was obtained with a quantity of 2.34 g and a yield of 89%. The synthesis scheme for Step 3 is shown in the following equation (a-3).

[0334] [Chemical Formula 43]

[0335]

[0336] In addition, nuclear magnetic resonance spectroscopy of the pale yellow solid obtained in step 3 above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 9. From this result, it was found that in this embodiment, an organic compound 9mDBtBPNfpr represented by the structural formula (100) described above was obtained.

[0337] 1 H-NMR.δ(CD2Cl2): 7.47-7.51 (m, 2H), 7.60-7.69 (m, 5H), 7.79-7.89 (m, 6H), 8.05 (d, 1H), 8.10-8.11 (m, 2H), 8.18-8.23 (m, 3H), 8.53(s, 1H), 9.16(d, 1H), 9.32(s, 1H).

[0338] Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as the 'absorption spectrum') and emission spectrum of 9mDBtBPNfpr in a toluene solution are shown in (A) of FIG. 10. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0339] A UV-visible spectrophotometer (model V550 manufactured by JASCO Corporation) was used to measure the absorption spectrum. The absorption spectrum of 9mDBtBPNfpr in a toluene solution was calculated by subtracting the absorption spectrum obtained by measuring with toluene in a quartz cell from the absorption spectrum obtained by measuring with a toluene solution of 9mDBtBPNfpr in a quartz cell. In addition, a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics KK) was used to measure the emission spectrum. The emission spectrum of 9mDBtBPNfpr in a toluene solution was measured by placing a toluene solution of 9mDBtBPNfpr in a quartz cell.

[0340] Figure 10 (A) shows that absorption peaks are identified at around 370 nm and 380 nm in a toluene solution of 9 mDBtBPNfpr, and emission wavelength peaks are identified at around 400 nm and 421 nm (excitation wavelength: 291 nm).

[0341] Next, the absorption and emission spectra of the 9mDBtBPNfpr solid thin film were measured. The solid thin film was fabricated on a quartz substrate by vacuum deposition. In addition, the absorption spectrum of the thin film is the absorbance (-log) obtained from the transmittance and reflectance including the substrate 10It was calculated from [%T / (100-%R)]). In addition, %T represents transmittance and %R represents reflectance. A UV-visible spectrophotometer (U-4100, manufactured by Hitachi High-Technologies Corporation) was used to measure the absorption spectrum. Additionally, a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK) was used to measure the emission spectrum. The measurement results of the absorption and emission spectra of the obtained solid thin film are shown in Figure 10 (B). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0342] Figure 10 (B) shows that absorption peaks are identified at around 377 nm and 395 nm in the solid thin film of 9 mDBtBPNfpr, and a peak of emission wavelength is identified at around 489 nm (excitation wavelength: 370 nm).

[0343] Therefore, it can be seen that the organic compound 9mDBtBPNfpr, which is one embodiment of the present invention, is a host material suitable for phosphorescent materials that emit red light and energy on the longer wavelength side. In addition, the organic compound 9mDBtBPNfpr, which is one embodiment of the present invention, can also be used as a host material or a light-emitting material for phosphorescent materials in the visible region.

[0344] Next, the LUMO level value of 9mDBtBPNfpr is presented. The LUMO level value is the reduction potential obtained by cyclic voltammetry (CV) measurement in dimethylformamide solvent and the reference electrode (Ag / Ag + It was estimated from the value of the potential energy (approximately -4.94 eV relative to the vacuum level). Specifically, it was set as "-4.94 [eV] - (value of reduction potential) = LUMO level". The measured value of the LUMO level calculated using this equation was -3.05 eV. Therefore, it can be seen that 9mDBtBPNfpr readily accepts electrons and has high electron stability.

[0345] (Example 2)

[0346] In this embodiment, the device structure, fabrication method, and characteristics thereof of light-emitting device 1, which uses 9-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mDBtBPNfpr) (structural formula (100)) described in Example 1 as a light-emitting device of one form of the present invention, and comparative light-emitting device 2, which uses 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated: 2mDBTBPDBq-II) as a light-emitting device, are described. In addition, the device structure of the light-emitting device used in this embodiment is shown in FIG. 11, and the specific configuration is shown in Table 1. Furthermore, the chemical formula of the material used in this embodiment is shown below.

[0347] [Table 1]

[0348]

[0349] * 9mDBtBPNfpr:PCBBiF:[Ir(dmdppr-P)2(dibm)](0.75:0.25:0.1 40nm)

[0350] ** 2mDBTBPDBq-II:PCBBiF:[Ir(dmdppr-P)2(dibm)](0.75:0.25:0.1 40nm)

[0351] [Chemical Formula 44]

[0352]

[0353] <<Fabrication of Light-Emitting Devices>>

[0354] As shown in FIG. 11, the light-emitting element described in this embodiment has a structure in which a hole injection layer (911), a hole transport layer (912), a light-emitting layer (913), an electron transport layer (914), and an electron injection layer (915) are sequentially stacked on a first electrode (901) formed on a substrate (900), and a second electrode (903) is stacked on the electron injection layer (915).

[0355] First, a first electrode (901) was formed on the substrate (900). The electrode area is 4 mm 2 (2mm × 2mm). In addition, a glass substrate was used for the substrate (900). In addition, the first electrode (901) was formed by depositing an indium tin oxide (ITSO) containing silicon oxide to a thickness of 70nm by sputtering.

[0356] Here, as a pretreatment, the substrate surface was cleaned with water and calcined at 200°C for 1 hour, followed by UV ozone treatment for 370 seconds. Afterward, the internal pressure was approximately 10 -4 A substrate was introduced into a vacuum deposition apparatus with reduced pressure to Pa, vacuum firing was performed at 170°C for 30 minutes in a heating chamber inside the vacuum deposition apparatus, and then the substrate was cooled for about 30 minutes.

[0357] Next, a hole injection layer (911) was formed on the first electrode (901). The hole injection layer (911) is formed by 10 pressure inside the vacuum deposition apparatus. -4 After reducing the pressure to Pa, 1,3,5-tri(dibenzothiophen-4-yl)benzene (abbreviated: DBT3P-II) and molybdenum oxide were co-deposited in a ratio of DBT3P-II:molybdenum oxide = 2:1 (mass ratio) to form a thickness of 75 nm.

[0358] Next, a hole transport layer (912) was formed on the hole injection layer (911). The hole transport layer (912) was formed by using 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BPAFLP) and depositing it to a thickness of 20 nm.

[0359] Next, a light-emitting layer (913) was formed on the hole transport layer (912).

[0360] In the case of light-emitting element 1, the light-emitting layer (913) is, in addition to 9mDBtBPNfpr and N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as PCBBiF), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptaneto-κ) as a guest material (phosphorescent light-emitting material). 2 O,O')iridium(III) (abbreviated: [Ir(dmdppr-P)2(dibm)]) was used and co-deposited with a weight ratio of 9mDBtBPNfpr:PCBBiF:[Ir(dmdppr-P)2(dibm)] = 0.75:0.25:0.1. In addition, the thickness was set to 40 nm. In addition, for comparative light-emitting element 2, [Ir(dmdppr-P)2(dibm)] was used as a guest material (phosphorescent light-emitting material) in addition to 2mDBTBPDBq-II and PCBBiF, and co-deposited with a weight ratio of 2mDBTBPDBq-II:PCBBiF:[Ir(dmdppr-P)2(dibm)] = 0.75:0.25:0.1. In addition, the thickness was set to 40 nm.

[0361] Next, an electron transport layer (914) was formed on the light-emitting layer (913). In the case of light-emitting element 1, the electron transport layer (914) was formed by sequentially depositing a film thickness of 9mDBtBPNfpr such that the film thickness was 30nm and a film thickness of 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBphen) such that the film thickness was 15nm. In addition, in the case of comparative light-emitting element 2, the electron transport layer was formed by sequentially depositing a film thickness of 2mDBTBPDBq-II such that the thickness was 30nm and a film thickness of NBphen such that the thickness was 15nm.

[0362] Next, an electron injection layer (915) was formed on the electron transport layer (914). The electron injection layer (915) was formed by using lithium fluoride (LiF) and depositing it to a thickness of 1 nm.

[0363] Next, a second electrode (903) was formed on the electron injection layer (915). The second electrode (903) was formed using aluminum by a deposition method to have a thickness of 200 nm. In addition, in this embodiment, the second electrode (903) functions as a cathode.

[0364] Through the process described above, a light-emitting element including an EL layer between a pair of electrodes was formed on a substrate (900). In addition, the hole injection layer (911), hole transport layer (912), light-emitting layer (913), electron transport layer (914), and electron injection layer (915) described in the process above are functional layers constituting an EL layer of one form of the present invention. Furthermore, in the deposition process of the fabrication method described above, a deposition method by resistance heating was used for all of them.

[0365] Additionally, the light-emitting element fabricated as described above is sealed with another substrate (not shown). Furthermore, when sealing using another substrate (not shown), another substrate (not shown) coated with a substance that solidifies by ultraviolet light in a glove box under a nitrogen atmosphere is fixed onto the substrate (900), and the substrates are bonded so that the substance is attached around the light-emitting element formed on the substrate (900). During sealing, ultraviolet light of 365 nm is applied at 6 J / cm² 2 The material was solidified by investigation, and stabilized by heat treatment at 80°C for 1 hour.

[0366] <<Operating Characteristics of Light-Emitting Devices>>

[0367] The operating characteristics of each fabricated light-emitting device were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25°C). Furthermore, as a result of the operating characteristics of each light-emitting device, the current density-luminance characteristics are shown in Fig. 12, the voltage-luminance characteristics in Fig. 13, the luminance-current efficiency characteristics in Fig. 14, and the voltage-current characteristics in Fig. 15, respectively.

[0368] Also, 1000 cd / m² 2The main initial characteristic values ​​of each light-emitting element in the vicinity are shown in Table 2 below.

[0369] [Table 2]

[0370]

[0371] As can be seen from the above results, the light-emitting element 1 fabricated in this embodiment exhibits good efficiency.

[0372] In addition, 2.5 mA / cm² for light-emitting element 1 and comparison light-emitting element 2 2 The emission spectrum when current is passed at a current density is shown in FIG. 16. As shown in FIG. 16, the emission spectra of light-emitting element 1 and comparison light-emitting element 2 have a peak around 640 nm, and both are suggested to originate from the emission of [Ir(dmdppr-P)2(dibm)] included in the light-emitting layer (913).

[0373] Next, reliability tests were performed on light-emitting element 1 and comparison light-emitting element 2. The results of the reliability test are shown in Fig. 17. In Fig. 17, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 50 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0374] As can be seen from the results of the reliability test, light-emitting element 1 has higher reliability than comparative light-emitting element 2. This is thought to be due to the difference in molecular structure between 9mDBtBPNfpr and 2mDBTBPDBq-II, namely the difference between the naphthofuropyrazine backbone and the dibenzoquinoxaline backbone, and thus can be said to indicate the robustness of the puropyrazine derivative, which is one embodiment of the present invention. Therefore, using the organic compound 9mDBtBPNfpr (structural formula (100)), which is one embodiment of the present invention, can be said to be useful for improving the device characteristics of the light-emitting element.

[0375] (Example 3)

[0376] In this embodiment, as a light-emitting element of one form of the present invention, a light-emitting element 3 is fabricated using the 9mDBtBPNfpr (structural formula (100)) described in Example 1 in the light-emitting layer, and the results of measuring the characteristics thereof are described.

[0377] In addition, in the fabrication of the light-emitting element 3, the first electrode (901) and the hole injection layer (911) were formed in the same way as the light-emitting element 1 described in Example 2.

[0378] In addition, the hole transport layer (912) formed on the hole injection layer (911) was formed by using 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBBi1BP) and depositing it to a thickness of 20 nm.

[0379] Additionally, the light-emitting layer (913) formed on the hole transport layer (912) uses 9mDBtBPNfpr and PCBBiF, and as a guest material (phosphorescent light-emitting material), bis[4,6-dimethyl-2-(2-quinorinyl-κN)phenyl-κC](2,4-pentanedioneto-κ 2 O,O')iridium(III) (abbreviated: [Ir(dmpqn)2(acac)]) was used, and formed by co-deposition with a weight ratio of 9mDBtBPNfpr:PCBBiF:[Ir(dmpqn)2(acac)]=0.8:0.2:0.1. In addition, the thickness was set to 40 nm.

[0380] In addition, the electron transport layer (914) formed on the light-emitting layer (913) was formed by sequentially depositing 9mDBtBPNfpr with a thickness of 30nm and NBphen with a thickness of 15nm.

[0381] Since the electron injection layer (915) and up to the second electrode (903) are formed in the same way as the light-emitting element 1 described in Example 2, the description is omitted. The specific configuration of the light-emitting element 3 is shown in Table 3. In addition, the chemical formula of the material used in this example is shown below.

[0382] [Table 3]

[0383]

[0384] * 9mDBtBPNfpr:PCBBiF:[Ir(dmpqn)2(acac)](0.8:0.2:0.1 40nm)

[0385] [Chemical Formula 45]

[0386]

[0387] <<Operating Characteristics of Light-Emitting Element 3>>

[0388] The operating characteristics of the fabricated light-emitting device 3 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0389] The current density-luminance characteristics of light-emitting element 3 are shown in Fig. 18, the voltage-luminance characteristics in Fig. 19, the luminance-current efficiency characteristics in Fig. 20, and the voltage-current characteristics in Fig. 21, respectively.

[0390] Also, 1000 cd / m² 2 The main initial characteristic values ​​of light-emitting element 3 in the vicinity are shown in Table 4 below.

[0391] [Table 4]

[0392]

[0393] As can be seen from the above results, the light-emitting element 3 fabricated in this embodiment exhibits good efficiency.

[0394] In addition, 2.5 mA / cm² for light-emitting element 3 2The emission spectrum when current is passed at a current density is shown in FIG. 22. As shown in FIG. 22, the emission spectrum of the light-emitting element has a peak around 626 nm and is suggested to originate from the emission of [Ir(dmpqn)2(acac)] included in the light-emitting layer (913).

[0395] Next, a reliability test was performed on light-emitting element 3. The results of the reliability test are shown in Fig. 23. In Fig. 23, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 75 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0396] As can be seen from the results of the reliability test, the light-emitting element 3 has high reliability. Therefore, using the organic compound 9mDBtBPNfpr (structural formula (100)), which is one form of the present invention, can be said to be useful for improving the device characteristics of the light-emitting element.

[0397] (Example 4)

[0398] In this embodiment, as a light-emitting element which is one form of the present invention, a light-emitting element 4 is fabricated using the 9mDBtBPNfpr (structural formula (100)) described in Example 1 in the light-emitting layer, and the results of measuring the characteristics thereof are described.

[0399] In addition, in the fabrication of the light-emitting element 4, the first electrode (901) and the hole injection layer (911) were formed in the same way as the light-emitting element 1 described in Example 2.

[0400] In addition, the hole transport layer (912) formed on the hole injection layer (911) was formed by using PCBBiF and depositing it to a thickness of 20 nm.

[0401] Additionally, the light-emitting layer (913) formed on the hole transport layer (912) uses 9mDBtBPNfpr and PCBBiF, and as a guest material (phosphorescent light-emitting material), bis{4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptaneto-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-m5CP)2(dpm)]) was used, and formed by co-deposition with a weight ratio of 9mDBtBPNfpr:PCBBiF:[Ir(dmdppr-m5CP)2(dpm)]=0.8:0.2:0.1. In addition, the thickness was set to 40 nm.

[0402] In addition, the electron transport layer (914) formed on the light-emitting layer (913) was formed by sequentially depositing 9mDBtBPNfpr with a thickness of 30nm and NBphen with a thickness of 15nm.

[0403] Since the electron injection layer (915) and up to the second electrode (903) are formed in the same way as the light-emitting element 1 described in Example 2, the description is omitted. The specific configuration of the light-emitting element 4 is shown in Table 5. In addition, the chemical formula of the material used in this example is shown below.

[0404] [Table 5]

[0405]

[0406] * 9mDBtBPNfpr:PCBBiF:[Ir(dmdppr-m5CP)2(dpm)](0.8:0.2:0.1 40nm)

[0407] [Chemical Formula 46]

[0408]

[0409] <<Operating Characteristics of Light-Emitting Element 4>>

[0410] The operating characteristics of the fabricated light-emitting element 4 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0411] The current density-luminance characteristics of light-emitting element 4 are shown in Fig. 24, the voltage-luminance characteristics in Fig. 25, the luminance-current efficiency characteristics in Fig. 26, and the voltage-current characteristics in Fig. 27, respectively.

[0412] Also, 1000 cd / m² 2 The main initial characteristic values ​​of light-emitting element 4 in the vicinity are shown in Table 6 below.

[0413] [Table 6]

[0414]

[0415] As can be seen from the above results, the light-emitting element 4 fabricated in this embodiment exhibits good efficiency.

[0416] In addition, 2.5 mA / cm² at light-emitting element 4 2 The emission spectrum when current is passed at a current density is shown in FIG. 28. As shown in FIG. 28, the emission spectrum of the light-emitting element has a peak around 648 nm and is suggested to originate from the emission of [Ir(dmdppr-m5CP)2(dpm)] included in the light-emitting layer (913).

[0417] Next, a reliability test was performed on light-emitting element 4. The results of the reliability test are shown in Fig. 29. In Fig. 29, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 75 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0418] As can be seen from the results of the reliability test, the light-emitting element 4 has high reliability. Therefore, using the organic compound 9mDBtBPNfpr (structural formula (100)), which is one form of the present invention, can be said to be useful for improving the device characteristics of the light-emitting element.

[0419] (Example 5)

[0420] In this embodiment, as a light-emitting element of one form of the present invention, a light-emitting element 5 is fabricated using the 9mDBtBPNfpr (structural formula (100)) described in Example 1 in the light-emitting layer, and the results of measuring the characteristics thereof are described.

[0421] The specific configuration of the light-emitting element 5 is shown in Table 7. In the table, APC represents an alloy of silver, palladium, and copper (Ag-Pd-Cu). Additionally, regarding the stacking of the light-emitting element, refer to FIG. 11. However, the light-emitting element 5 is a light-emitting element including a cap layer formed in contact with the second electrode (903). Furthermore, the chemical formula of the material used in this embodiment is shown below.

[0422] [Table 7]

[0423]

[0424] * 9mDBtBPNfpr:PCBBiF:[Ir(dmdppr-m5CP)2(dpm)](0.8:0.2:0.04 40nm)

[0425] [Chemical Formula 47]

[0426]

[0427] <<Operating Characteristics of Light-Emitting Element 5>>

[0428] The operating characteristics of the fabricated light-emitting element 5 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0429] The current density-luminance characteristics of light-emitting element 5 are shown in Fig. 30, the voltage-luminance characteristics in Fig. 31, the luminance-current efficiency characteristics in Fig. 32, and the voltage-current characteristics in Fig. 33, respectively.

[0430] Also, 1000 cd / m² 2 The main initial characteristic values ​​of light-emitting element 5 in the vicinity are shown in Table 8 below.

[0431] [Table 8]

[0432]

[0433] As can be seen from the above results, the light-emitting element 5 fabricated in this embodiment exhibits good efficiency.

[0434] In addition, 2.5 mA / cm at light-emitting element 5 2 The emission spectrum when current is passed at a current density is shown in FIG. 34. As shown in FIG. 34, the emission spectrum of the light-emitting element has a peak around 635 nm and is suggested to originate from the emission of [Ir(dmdppr-m5CP)2(dpm)] included in the light-emitting layer (913). Therefore, it can be seen that the organic compound 9mDBtBPNfpr, which is one embodiment of the present invention, is a host material suitable for a phosphorescent material that emits red light and energy on the longer wavelength side.

[0435] Next, a reliability test was performed on light-emitting element 5. The results of the reliability test are shown in Fig. 35. In Fig. 35, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 12.5 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0436] As can be seen from the results of the reliability test, the light-emitting element 5 has high reliability. Therefore, using the organic compound 9mDBtBPNfpr (structural formula (100)), which is one form of the present invention, can be said to be useful for improving the device characteristics of the light-emitting element.

[0437] Here, assuming a panel of a top emission structure formed by combining light-emitting element 5 with other light-emitting elements (light-emitting element 6 and light-emitting element 7) having the device structure shown in Table 9 and the operating characteristics shown in Table 10, the aperture ratio is 15% (each pixel of R, G, and B is 5%), the attenuation of light emission by a circular polarizer, etc. is 60%, and D65 and 300 cd / m² 2 A simulation was performed in the case where everything was displayed in white.

[0438] [Table 9]

[0439]

[0440] In addition, the chemical formulas of some materials used in each light-emitting element of Table 9 are shown below.

[0441] [Chemical Formula 48]

[0442]

[0443] [Table 10]

[0444]

[0445] Table 11 shows the data used in the simulation among the measurement results of the light-emitting element above.

[0446] [Table 11]

[0447]

[0448] According to a simulation using the data in Table 11, when the chromaticity (x, y) of each light-emitting element was calculated from the CIE1976 chromaticity coordinates (u'v' chromaticity coordinates), the result showed that the area ratio of the BT.2020 standard color gamut in a panel formed by combining light-emitting element 5 (R), light-emitting element 6 (G), and light-emitting element 7 (B) was 97%.

[0449] (Example 6)

[0450] <<Synthesized Example 2>>

[0451] In this embodiment, a method for synthesizing the organic compound 9-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9PCCzNfpr), which is one form of the present invention represented by the structural formula (123) of Embodiment 1, is described. Additionally, the structure of 9PCCzNfpr is shown below.

[0452] [Chemical Formula 49]

[0453]

[0454] 0.94 g of 9-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 2 of Example 1, 1.69 g of 9'-phenyl-3,3'-bi-9H-carbazole, and 37 mL of mesitylene were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 1.23 g of sodium tert-butoxide, 0.021 g of tris(dibenzylideneacetone)dipalladium (O) (abbreviated: Pd2(dba)3), and 0.030 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated: S-Phos) were added, and the mixture was reacted by stirring at 120°C for 8 hours.

[0455] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using a mixed solvent of toluene and hexane to obtain the target product (yellow solid, quantity 0.85g, yield 36%).

[0456] 0.84 g of the obtained yellow solid was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 350°C while flowing argon gas at a flow rate of 10 mL / min under a pressure of 2.5 Pa. After sublimation purification, the target yellow solid was obtained with a quantity of 0.64 g and a yield of 76%. The synthesis scheme of the above synthesis method is shown in the following equation (b-1).

[0457] [Chemical Formula 50]

[0458]

[0459] In addition, nuclear magnetic resonance spectroscopy of the yellow solid obtained by the above synthesis method ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 36. From this result, it was found that in this embodiment, an organic compound 9PCCzNfpr represented by the structural formula (123) described above was obtained.

[0460] 1 H-NMR.δ(CDCl3):7.32-7.35(m, 1H), 7.42-7.57(m, 6H), 7.63-7.70(m, 5H), 7.80-7.90(m, 4H), 8.09(d, 2H), 8.14(d, 2H), 8.27(d, 2H), 8.49(d, 2H), 9.20(d, 1H), 9.27(s, 1H).

[0461] (Example 7)

[0462] <<Synthesized Example 3>>

[0463] In this embodiment, a method for synthesizing the organic compound 9-[3-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mPCCzPNfpr), which is one form of the present invention represented by the structural formula (125) of Embodiment 1, is described. Additionally, the structure of 9mPCCzPNfpr is shown below.

[0464] [Chemical Formula 51]

[0465]

[0466] <Step 1: Synthesis of 9-(3-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine>

[0467] 2.12 g of 9-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 2 of Example 1, 1.41 g of 3-chlorophenylboronic acid, 14 mL of 2 M aqueous potassium carbonate solution, 83 mL of toluene, and 8.3 mL of ethanol were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.19 g of palladium(II) acetate (abbreviated: Pd(OAc)2) and 1.12 g of tris(2,6-dimethoxyphenyl)phosphine (abbreviated: P(2,6-MeOPh)3) were added, and the mixture was reacted by stirring at 90°C for 7 and a half hours.

[0468] After a predetermined amount of time had elapsed, the obtained mixture was filtered by suction and washed with ethanol. Subsequently, it was purified by silica gel column chromatography using toluene as the developing solvent to obtain the desired pyrazine derivative (yellowish-white powder, quantity 1.97 g, yield 73%). The synthesis scheme of Step 1 is shown in the following formula (c-1).

[0469] [Chemical Formula 52]

[0470]

[0471] <Step 2: Synthesis of 9mPCCzPNfpr>

[0472] Next, 1.45 g of 9-(3-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine obtained in Step 1, 1.82 g of 9'-phenyl-3,3'-bi-9H-carbazole, and 22 mL of mesitylene were placed in a 3-neck flask, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.85 g of sodium tert-butoxide, 0.025 g of tris(dibenzylideneacetone)dipalladium (O) (abbreviated: Pd2(dba)3), and 0.036 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated: S-Phos) were added, and the mixture was reacted by stirring at 150°C for 7 hours.

[0473] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using a mixed solvent of toluene and hexane to obtain the target product (yellow solid, quantity 2.22 g, yield 71%).

[0474] The obtained yellow solid 2.16 g was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 385°C under a pressure of 2.6 Pa while flowing argon gas at a flow rate of 18 mL / min. After sublimation purification, the target yellow solid was obtained with a quantity of 1.67 g and a yield of 77%. The synthesis scheme for Step 2 is shown in the following equation (c-2).

[0475] [Chemical Formula 53]

[0476]

[0477] In addition, nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 2 above ( 1 The analysis results by H-NMR are shown below. In addition, 1The H-NMR chart is shown in FIG. 37. From this result, it was found that in this embodiment, an organic compound 9mPCCzPNfpr represented by the structural formula (125) described above was obtained.

[0478] 1 H-NMR.δ(CD2Cl2):7.31-7.39(m, 2H), 7.43-7.59(m, 6H), 7.64-7.69(m, 6H), 7.78-7.88(m, 6H), 8.09(d, 1H), 8.15(d, 1H), 8.26(d, 1H), 8.30(d, 1H), 8.34(d, 1H), 8.51-8.55(m, 3H), 9.15(d, 1H), 9.35(s, 1H).

[0479] (Example 8)

[0480] <<Synthesized Example 4>>

[0481] In this embodiment, a method for synthesizing the organic compound 9-[3-(9'-phenyl-2,3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mPCCzPNfpr-02), which is one form of the present invention represented by the structural formula (126) of Embodiment 1, is described. Additionally, the structure of 9mPCCzPNfpr-02 is shown below.

[0482] [Chemical Formula 54]

[0483]

[0484] 1.19 g of 9-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 2 of Example 1, 3.51 g of 3-(9'-phenyl-2,3'-bi-9H-carbazole-9-yl)phenylboronic acid pinacol ester, 6.0 mL of 2 M potassium carbonate aqueous solution, 60 mL of toluene, and 6 mL of ethanol were placed in a three-necked flask, and the interior was purged with nitrogen. After degassing by stirring under reduced pressure, 0.33 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviated: Pd(PPh3)2Cl2) was added, and the mixture was reacted by stirring at 90°C for 16 hours.

[0485] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using a mixed solvent of toluene and hexane to obtain the target product (yellow solid, quantity 3.01 g, yield 90%).

[0486] 3.00 g of the obtained yellow solid was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 380°C under a pressure of 2.7 Pa while flowing argon gas at a flow rate of 16 mL / min. After sublimation purification, the target yellow solid was obtained with a quantity of 2.47 g and a yield of 82%. The synthesis scheme is shown in the following equation (d-1).

[0487] [Chemical Formula 55]

[0488]

[0489] In addition, nuclear magnetic resonance spectroscopy of the yellow solid obtained above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 38. From this result, it was found that in this embodiment, an organic compound 9mPCCzPNfpr-02 represented by the structural formula (126) described above was obtained.

[0490] 1 H-NMR.δ(CD2Cl2):7.22-7.25(m, 1H), 7.34-7.42(m, 3H), 7.46-7.49(m, 3H), 7.55-7.66(m, 6H), 7.72-7.88(m, 7H), 8.07(d, 1H), 8.13(d, 1H), 8.19-8.22(m, 2H), 8.28(d, 1H), 8.33(d, 1H), 8.46(s, 1H), 8.54(s, 1H), 9.14(d, 1H), 9.34(s, 1H).

[0491] (Example 9)

[0492] <<Synthesized Example 5>>

[0493] In this embodiment, a method for synthesizing the organic compound 10-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 10mDBtBPNfpr), which is one form of the present invention represented by the structural formula (133) of Embodiment 1, is described. Additionally, the structure of 10mDBtBPNfpr is shown below.

[0494] [Chemical Formula 56]

[0495]

[0496] <Step 1: Synthesis of 5-chloro-3-(2-methoxynaphthalene-1-yl)pyrazine-2-amine>

[0497] First, 5.01 g of 3-bromo-5-chloropyrazine-2-amine, 6.04 g of 2-methoxynaphthalene-1-boronic acid, 5.32 g of potassium fluoride, and 86 mL of dehydrated tetrahydrofuran were placed in a 3-neck flask equipped with a reflux tube, and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 0.44 g of tris(dibenzylideneacetone)dipalladium (O) (abbreviated: Pd2(dba)3) and 3.4 mL of tri-tert-butylphosphine (abbreviated: P(tBu)3) were added, and the mixture was reacted by stirring at 80°C for 22 hours.

[0498] After a predetermined amount of time had elapsed, the obtained mixture was filtered by suction and the filtrate was concentrated. Subsequently, the mixture was purified by silica gel column chromatography using toluene:ethyl acetate = 10:1 as the developing solvent to obtain the desired pyrazine derivative (yellowish-white powder, quantity 5.69 g, yield 83%). The synthesis scheme of Step 1 is shown in the following formula (e-1).

[0499] [Chemical Formula 57]

[0500]

[0501] <Step 2: Synthesis of 10-Chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine>

[0502] Next, 5.69 g of 5-chloro-3-(2-methoxynaphthalene-1-yl)pyrazine-2-amine obtained in Step 1, 150 mL of dehydrated tetrahydrofuran, and 150 mL of glacial acetic acid were placed in a three-necked flask, and the interior was purged with nitrogen. After cooling the flask to -10°C, 7.1 mL of tert-butyl nitrite was added dropwise, and the mixture was stirred for 1 hour at -10°C and for 3.5 hours at 0°C. After the specified time had elapsed, 1 L of water was added to the obtained suspension and the desired pyrazine derivative was obtained by suction filtration (yellowish-white powder, quantity 4.06 g, yield 81%). The synthesis scheme for Step 2 is shown in the following equation (e-2).

[0503] [Chemical Formula 58]

[0504]

[0505] <Step 3: Synthesis of 10mDBtBPNfpr>

[0506] In addition, 1.18 g of 10-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine obtained in Step 2 above, 2.75 g of 3'-(4-dibenzothiophen)-1,1'-biphenyl-3-boronic acid, 7.5 mL of 2 M aqueous potassium carbonate solution, 60 mL of toluene, and 6 mL of ethanol were placed in a three-necked flask, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.66 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviated: Pd(PPh3)2Cl2) was added, and the mixture was reacted by stirring at 90°C for 22 and a half hours.

[0507] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using a mixed solvent of toluene and hexane to obtain the target product (white solid, quantity 2.27 g, yield 87%).

[0508] The obtained white solid 2.24 g was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 310°C under a pressure of 2.3 Pa while flowing argon gas at a flow rate of 16 mL / min. After sublimation purification, the target white solid was obtained with a quantity of 1.69 g and a yield of 75%. The synthesis scheme for Step 3 is shown in the following equation (e-3).

[0509] [Chemical Formula 59]

[0510]

[0511] In addition, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 39. From this result, it was found that in this embodiment, an organic compound 10mDBtBPNfpr represented by the structural formula (133) described above was obtained.

[0512] 1 H-NMR.δ(CDCl3):7.43(t, 1H), 7.48(t, 1H), 7.59-7.62(m, 3H), 7.68-7.86(m, 8H), 8.05(d, 1H), 8.12(d, 1H), 8.18(s, 1H), 8.20-8.24(m, 3H), 8.55(s, 1H), 8.92(s, 1H), 9.31(d, 1H).

[0513] (Example 10)

[0514] <<Synthesized Example 6>>

[0515] In this embodiment, a method for synthesizing the organic compound 10-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 10PCCzNfpr), which is one form of the present invention represented by the structural formula (156) of Embodiment 1, is described. Additionally, the structure of 10PCCzNfpr is shown below.

[0516] [Chemical Formula 60]

[0517]

[0518] 1.80 g of 10-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 2 of Example 9, 3.10 g of 9'-phenyl-3,3'-bi-9H-carbazole, and 71 mL of mesitylene were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 2.21 g of sodium tert-butoxide, 0.041 g of tris(dibenzylideneacetone)dipalladium (O) (abbreviated: Pd2(dba)3), and 0.061 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated: S-Phos) were added, and the mixture was reacted by stirring at 120°C for 2 hours.

[0519] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using a mixed solvent of toluene and hexane to obtain the target product (orange solid, quantity 3.47 g, yield 78%).

[0520] The obtained orange solid 3.42 g was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 350°C under a pressure of 2.4 Pa while flowing argon gas at a flow rate of 16 mL / min. After sublimation purification, the target orange solid was obtained with a quantity of 2.86 g and a yield of 84%. The synthesis scheme for Step 3 is shown in the following equation (f-1).

[0521] [Chemical Formula 61]

[0522]

[0523] In addition, nuclear magnetic resonance spectroscopy of the orange solid obtained by the above synthesis method ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 40. From this result, it was found that in this embodiment, an organic compound 10PCCzNfpr represented by the structural formula (156) described above was obtained.

[0524] 1 H-NMR.δ(CDCl3):7.32-7.35(m, 1H), 7.43-7.57(m, 6H), 7.63-7.68(m, 5H), 7.79-7.84(m, 2H), 7.89-7.91(m, 2H), 8.01(d, 1H), 8.07-8.09(m, 2H), 8.18(d, 1H), 8.27(d, 1H), 8.30(d, 1H), 8.51(s, 2H), 8.85(s, 1H), 9.16(d, 1H).

[0525] (Example 11)

[0526] <<Synthesized Example 7>>

[0527] In this embodiment, a method for synthesizing the organic compound 12-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]phenantro[9',10':4,5]furo[2,3-b]pyrazine (abbreviated: 12mDBtBPPnfpr), which is one form of the present invention represented by the structural formula (208) of Embodiment 1, is described. Additionally, the structure of 12mDBtBPPnfpr is shown below.

[0528] [Chemical Formula 62]

[0529]

[0530] <Step 1: Synthesis of 9-Methoxyphenanthrene>

[0531] First, 4.02 g of 9-bromo-phenanthrene, 7.80 g of cesium carbonate, 16 mL of toluene, and 16 mL of methanol were placed in a three-necked flask equipped with a reflux tube, and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 0.11 g of palladium(II) acetate (abbreviated: Pd(OAc)2) and 0.41 g of 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (abbreviated: tBuXPhos) were added, and the mixture was reacted by stirring at 80°C for 17 hours.

[0532] After a predetermined amount of time had elapsed, the obtained mixture was filtered by suction and the filtrate was concentrated. Subsequently, the product was purified by silica gel column chromatography using toluene:hexane = 1:3 as the developing solvent to obtain the target product (white powder, quantity 2.41 g, yield 74%). The synthesis scheme of Step 1 is shown in the following formula (g-1).

[0533] [Chemical Formula 63]

[0534]

[0535] <Step 2: Synthesis of 9-Bromo-10-Methoxyphenanthrene>

[0536] Next, 2.75 g of 9-methoxyphenanthrene obtained in Step 1, 0.18 mL of diisopropylamine, 150 mL of dehydrated dichloromethane, and 2.52 g of N-bromosuccinimide (abbreviated: NBS) were placed in a triangular flask and stirred at room temperature for 18 hours. After the specified time had elapsed, the mixture was washed with water and an aqueous sodium thiosulfate solution and concentrated. Subsequently, the product was purified by silica gel column chromatography using hexane:ethyl acetate = 5:1 as the developing solvent to obtain the target product (yellowish-white powder, quantity 2.46 g, yield 65%). The synthesis scheme of Step 2 is shown in the following formula (g-2).

[0537] [Chemical Formula 64]

[0538]

[0539] <Step 3: Synthesis of 10-Methoxyphenanthren-9-Boronic Acid>

[0540] Next, 8.49 g of 9-bromo-10-methoxyphenanthrene obtained in Step 2 above and 250 mL of dehydrated THF were placed in a three-necked flask, and the interior was purged with nitrogen. After cooling the flask to -78°C, 22 mL of n-butyllithium (1.6 M hexane solution) was added, and the mixture was stirred at -78°C for 3 hours. Subsequently, 5.7 mL of tetramethylethylenediamine and 4.3 mL of trimethyl borate were added, and the reaction was carried out by stirring at room temperature for 18 hours.

[0541] After a predetermined amount of time had elapsed, 50 mL of 1 M hydrochloric acid was added and stirred at room temperature for 1 hour. Subsequently, the target product was obtained by performing extraction with toluene (light orange powder, quantity 2.87 g, yield 39%). The synthesis scheme of Step 3 is shown in the following formula (g-3).

[0542] [Chemical Formula 65]

[0543]

[0544] <Step 4: Synthesis of 5-chloro-3-(10-methoxyphenanthren-9-yl)pyrazine-2-amine>

[0545] Next, 3.69 g of 10-methoxyphenanthrene-9-boronic acid obtained in step 3, 3.02 g of 3-bromo-5-chloropyrazine-2-amine, 70 mL of toluene, and 35 mL of 2 M aqueous sodium carbonate solution were placed in a 3-neck flask equipped with a reflux tube, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.16 g of tetrakis(triphenylphosphine)palladium (O) (abbreviated: Pd(PPh3)4) was added, and the reaction was carried out by stirring at 110°C for 7 and a half hours.

[0546] After a predetermined amount of time had elapsed, extraction with toluene was performed. Subsequently, the product was purified by flash column chromatography using dichloromethane:ethyl acetate = 50:1 as the developing solvent to obtain the desired pyrazine derivative (yellowish-white powder, quantity 3.00 g, yield 62%). The synthesis scheme of Step 4 is shown in the following formula (g-4).

[0547] [Chemical Formula 66]

[0548]

[0549] <Step 5: Synthesis of 12-Chlorophenantro[9',10':4,5]furo[2,3-b]pyrazine>

[0550] Next, 2.92 g of 5-chloro-3-(10-methoxyphenanthren-9-yl)pyrazine-2-amine obtained in step 4, 60 mL of dehydrated tetrahydrofuran, and 60 mL of glacial acetic acid were placed in a 3-neck flask, and the interior was purged with nitrogen. After cooling the flask to -10°C, 3.1 mL of tert-butyl nitrite was added dropwise, and the mixture was stirred for 1 hour at -10°C and for 22 hours at 0°C.

[0551] After a predetermined amount of time had elapsed, 200 mL of water was added to the obtained suspension and suction filtration was performed to obtain the desired pyrazine derivative (yellowish-white powder, quantity 2.06 g, yield 80%). The synthesis scheme of Step 5 is shown in the following formula (g-5).

[0552] [Chemical Formula 67]

[0553]

[0554] <Step 6: Synthesis of 12-(3-chlorophenyl)phenantro[9',10':4,5]furo[2,3-b]pyrazine>

[0555] Next, 1.02 g of 12-chlorophenantro[9',10':4,5]furo[2,3-b]pyrazine obtained in step 5 above, 0.56 g of 3-chlorophenylboronic acid, 5 mL of 2 M aqueous potassium carbonate solution, 33 mL of toluene, and 3.3 mL of ethanol were placed in a 3-neck flask, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.074 g of palladium(II) acetate (abbreviated: Pd(OAc)2) and 0.44 g of tris(2,6-dimethoxyphenyl)phosphine (abbreviated: P(2,6-MeOPh)3) were added, and the mixture was reacted by stirring at 90°C for 5 and a half hours.

[0556] After a predetermined amount of time had elapsed, the obtained mixture was filtered by suction and the filtrate was concentrated. Subsequently, the mixture was purified by silica gel column chromatography using toluene as the developing solvent to obtain the desired pyrazine derivative (white powder, quantity 0.87 g, yield 70%). The synthesis scheme of Step 6 is shown in the following formula (g-6).

[0557] [Chemical Formula 68]

[0558]

[0559] <Step 7: Synthesis of 12mDBtBPPnfpr>

[0560] Next, 0.85 g of 12-(3-chlorophenyl)phenantro[9',10':4,5]furo[2,3-b]pyrazine obtained in step 6 above, 0.73 g of 3-(4-dibenzothiophene)phenylboronic acid, 1.41 g of tripotassium phosphate, 0.49 g of tert-butyl alcohol, and 18 mL of diethylene glycol dimethyl ether (abbreviated as diglyme) were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 9.8 mg of palladium(II) acetate (abbreviated: Pd(OAc)2) and 32 mg of di(1-adamantyl)-n-butylphosphine (abbreviated: CataCXium A) were added, and the mixture was reacted by stirring at 140°C for 11 and a half hours.

[0561] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filtration aid layered in the order of celite, alumina, and celite, and then recrystallized using toluene to obtain the target product (white solid, quantity 0.74g, yield 55%).

[0562] 0.73 g of the obtained white solid was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 330°C while flowing argon gas at a flow rate of 11 mL / min under a pressure of 2.6 Pa. After sublimation purification, the target white solid was obtained with a quantity of 0.49 g and a yield of 67%. The synthesis scheme of Step 7 is shown in the following formula (g-7).

[0563] [Chemical Formula 69]

[0564]

[0565] In addition, nuclear magnetic resonance spectroscopy of the white solid obtained in step 7 above ( 1 The analysis results by H-NMR are shown below. In addition, 1The H-NMR chart is shown in FIG. 41. From this result, it was found that in this embodiment, an organic compound 12mDBtBPPnfpr represented by the structural formula (208) described above was obtained.

[0566] 1 H-NMR.δ(CD2Cl2):7.45(t, 1H), 7.50(t, 1H), 7.62-7.66(m, 2H), 7.70-7.89(m, 10H), 8.21-8.28(m, 4H), 8.58-8.61(m, 2H), 8.80(d, 1H), 8.84(d, 1H), 8.94(s, 1H), 9.37(d, 1H).

[0567] (Example 12)

[0568] <<Synthesized Example 8>>

[0569] In this embodiment, a method for synthesizing the organic compound 9-[4-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9pPCCzPNfpr), which is one form of the present invention represented by the structural formula (238) of Embodiment 1, is described. Additionally, the structure of 9pPCCzPNfpr is shown below.

[0570] [Chemical Formula 70]

[0571]

[0572] <Step 1: Synthesis of 9-(4-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine>

[0573] 4.10 g of 9-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 2 of Example 1, 2.80 g of 4-chlorophenylboronic acid, 27 mL of 2 M aqueous potassium carbonate solution, 160 mL of toluene, and 16 mL of ethanol were placed in a 3-neck flask, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.36 g of palladium(II) acetate (abbreviated: Pd(OAc)2) and 2.08 g of tris(2,6-dimethoxyphenyl)phosphine (abbreviated: P(2,6-MeOPh)3) were added, and the mixture was reacted by stirring at 90°C for 7 hours.

[0574] After a predetermined amount of time had elapsed, the obtained mixture was filtered by suction and washed with ethanol. Subsequently, it was purified by silica gel column chromatography using toluene as the developing solvent to obtain the desired pyrazine derivative (yellowish-white powder, quantity 2.81 g, yield 52%). The synthesis scheme of Step 1 is shown in the following formula (h-1).

[0575] [Chemical Formula 71]

[0576]

[0577] <Step 2: Synthesis of 9pPCCzPNfpr>

[0578] Next, 1.39 g of 9-(4-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine obtained in Step 1, 1.72 g of 9'-phenyl-3,3'-bi-9H-carbazole, and 21 mL of mesitylene were placed in a 3-neck flask, and the interior was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.81 g of sodium tert-butoxide, 0.024 g of tris(dibenzylideneacetone)dipalladium (O) (abbreviated: Pd2(dba)3), and 0.034 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated: S-Phos) were added, and the mixture was reacted by stirring at 150°C for 6 hours.

[0579] After a predetermined amount of time had elapsed, extraction with toluene was performed on the reaction solution. The solid obtained by concentrating the extraction solution was purified by silica gel column chromatography using toluene as the developing solvent, and the target product was obtained by recrystallizing three times using toluene (yellow solid, quantity 1.84 g, yield 62%).

[0580] The obtained yellow solid 1.81 g was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 380°C under a pressure of 2.7 Pa while flowing argon gas at a flow rate of 18 mL / min. After sublimation purification, the target yellow solid was obtained with a quantity of 1.35 g and a yield of 75%. The synthesis scheme for Step 2 is shown in the following equation (h-2).

[0581] [Chemical Formula 72]

[0582]

[0583] In addition, nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 2 above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 42. From this result, it was found that in this embodiment, the organic compound 9pPCCzPNfpr represented by the structural formula (238) described above was obtained.

[0584] 1 H-NMR.δ(CD2Cl2):7.32-7.39(m, 2H), 7.44-7.56(m, 5H), 7.61(d, 1H), 7.64-7.69(m, 6H), 7.83-7.91(m, 6H), 8.11(d, 1H), 8.17(d, 1H), 8.28(d, 2H), 8.49-8.53(m, 4H), 9.18(d, 1H), 9.40(s, 1H).

[0585] (Example 13)

[0586] <<Synthesized Example 9>>

[0587] In this embodiment, a method for synthesizing the organic compound 9-[4-(9'-phenyl-2,3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9pPCCzPNfpr-02), which is one form of the present invention represented by the structural formula (239) of Embodiment 1, is described. Additionally, the structure of 9pPCCzPNfpr-02 is shown below.

[0588] [Chemical Formula 73]

[0589]

[0590] 1.76 g of 9-(4-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine, described in Step 1 of Example 12, 2.22 g of 9'-phenyl-2,3'-bi-9H-carbazole, and 27 mL of mesitylene were placed in a 3-neck flask and the interior was nitrogen-substituted. After degassing by stirring the flask under reduced pressure, 1.09 g of sodium tert-butoxide, 0.031 g of tris(dibenzylideneacetone)dipalladium (0) (abbreviated: Pd2(dba)3), and 0.045 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated: S-Phos) were added and reacted by stirring at 150°C for 6 hours.

[0591] After a predetermined amount of time had elapsed, the obtained suspension was subjected to suction filtration, and the filtrate was washed with water and ethanol. The obtained solid was purified by silica gel column chromatography using toluene as the developing solvent, and the target product was obtained by recrystallization using a mixed solvent of toluene and hexane (yellow solid, quantity 1.95 g, yield 52%).

[0592] The obtained yellow solid 1.94 g was purified by sublimation purification using the train sublimation method. Sublimation purification was performed by heating the solid at 380°C while flowing argon gas at a flow rate of 18 mL / min under a pressure of 2.7 Pa. After sublimation purification, the target yellow solid was obtained with a quantity of 1.62 g and a yield of 84%. The synthesis scheme is shown in the following equation (i-1).

[0593] [Chemical Formula 74]

[0594]

[0595] In addition, nuclear magnetic resonance spectroscopy of the yellow solid obtained above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 43. From this result, it was found that in this embodiment, the organic compound 9pPCCzPNfpr-02 represented by the structural formula (239) described above was obtained.

[0596] 1 H-NMR.δ(CD2Cl2):7.28-7.31(m, 1H), 7.36(t, 1H), 7.40-7.44(m, 2H), 7.46-7.51(m, 3H), 7.57-7.69(m, 6H), 7.74(d, 1H), 8.78(d, 1H), 7.84(t, 1H), 7.81-7.88(m, 4H), 8.10(d, 1H), 8.16(d, 1H), 8.22(d, 2H), 8.28(d, 1H), 8.46(s, 1H), 8.50(d, 2H), 9.17(d, 1H), 9.38(s, 1H).

[0597] (Example 14)

[0598] <<Synthesized Example 10>>

[0599] In this embodiment, a method for synthesizing the organic compound 9-[3'-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mBnfBPNfpr), which is one form of the present invention represented by the structural formula (244) of Embodiment 1, is described. Additionally, the structure of 9mBnfBPNfpr is shown below.

[0600] [Chemical Formula 75]

[0601]

[0602] 1.28 g of 9-(3-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine, described in Step 1 of Example 7, 2.26 g of 3-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)phenylboronic acid pinacol ester, 2.53 g of tripotassium phosphate, 0.89 g of tert-butyl alcohol, and 32 mL of diethylene glycol dimethyl ether (abbreviated as diglyme) were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 8.8 mg of palladium(II) acetate (abbreviated: Pd(OAc)2) and 28 mg of di(1-adamantyl)-n-butylphosphine (abbreviated: CataCXium A) were added, and the mixture was reacted by stirring at 140°C for 8 and a half hours.

[0603] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was purified by silica gel column chromatography using toluene as the developing solvent, and the target product was obtained by recrystallization using toluene (yellow solid, quantity 0.66 g, yield 25%). The synthesis scheme is shown in the following formula (j-1).

[0604] [Chemical Formula 76]

[0605]

[0606] In addition, nuclear magnetic resonance spectroscopy of the yellow solid obtained above ( 1The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 44. From this result, it was found that in this embodiment, an organic compound 9mBnfBPNfpr represented by the structural formula (244) described above was obtained.

[0607] 1 H-NMR.δ(CD2Cl2):7.24-7.28(m, 3H), 7.61-7.72(m, 5H), 7.78-7.87(m, 6H), 7.98-8.00(m, 3H), 8.08(d, 1H), 8.11-8.15(m, 3H), 8.25(d, 1H), 8.48(s, 1H), 8.51-8.53(m, 2H), 8.75(d, 1H), 9.15(d, 1H), 9.32(s, 1H).

[0608] (Example 15)

[0609] <<Synthesized Example 11>>

[0610] In this embodiment, a method for synthesizing the organic compound 9-[3'-(6-phenyldibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mDBtBPNfpr-02), which is one form of the present invention represented by the structural formula (245) of Embodiment 1, is described. Additionally, the structure of 9mDBtBPNfpr-02 is shown below.

[0611] [Chemical Formula 77]

[0612]

[0613] 1.19 g of 9-(3-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 1 of Example 7, 1.97 g of 3-(6-phenyldibenzothiophen-4-yl)phenylboronic acid pinacol ester, 2.29 g of tripotassium phosphate, 0.82 g of tert-butyl alcohol, and 29 mL of diethylene glycol dimethyl ether (abbreviated as diglyme) were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 16 mg of palladium acetate (II) (abbreviated: Pd(OAc)2) and 52 mg of di(1-adamantyl)-n-butylphosphine (abbreviated: CataCXium A) were added, and the mixture was reacted by stirring at 140°C for 15 hours.

[0614] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was purified by silica gel column chromatography using toluene as the developing solvent, and the target product was obtained by recrystallization using toluene (yellowish-white solid, quantity 1.17 g, yield 52%). The synthesis scheme is shown in the following formula (k-1).

[0615] [Chemical Formula 78]

[0616]

[0617] In addition, nuclear magnetic resonance spectroscopy of the yellowish-white solid obtained above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 45. From this result, it was found that in this embodiment, the organic compound 9mDBtBPNfpr-02 represented by the structural formula (245) described above was obtained.

[0618] 1H-NMR.δ(CD2Cl2):7.39(t, 1H), 7.47-7.51(m, 3H), 7.58-7.67(m, 6H), 7.73(d, 2H), 7.78-7.85(m, 5H), 8.02(s, 1H), 8.06(d, 1H), 8.10(d, 1H), 8.18(d, 1H), 8.23(t, 2H), 8.49(s, 1H), 9.17(d, 1H), 9.30(s, 1H).

[0619] (Example 16)

[0620] <<Synthesized Example 12>>

[0621] In this embodiment, a method for synthesizing the organic compound 9-{3-[6-(9,9-dimethylfluorene-2-yl)dibenzothiophen-4-yl]phenyl}naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mFDBtPNfpr), which is one form of the present invention represented by the structural formula (246) of Embodiment 1, is described. Additionally, the structure of 9mFDBtPNfpr is shown below.

[0622] [Chemical Formula 79]

[0623]

[0624] 1.01 g of 9-(3-chlorophenyl)naphtho[1',2':4,5]furo[2,3-b]pyrazine, the synthesis method described in Step 1 of Example 7, 1.46 g of 3-[6-(9,9-dimethylfluorene-2-yl)dibenzothiophen-4-yl]phenylboronic acid, 1.89 g of tripotassium phosphate, 0.67 g of tert-butyl alcohol, and 24 mL of diethylene glycol dimethyl ether (abbreviated as diglyme) were placed in a 3-neck flask and the interior was purged with nitrogen. After degassing by stirring the flask under reduced pressure, 27 mg of palladium acetate (II) (abbreviated: Pd(OAc)2) and 88 mg of di(1-adamantyl)-n-butylphosphine (abbreviated: CataCXium A) were added, and the mixture was reacted by stirring at 140°C for 30 hours.

[0625] After a predetermined amount of time had elapsed, the obtained suspension was filtered by suction and washed with water and ethanol. The obtained solid was purified by silica gel column chromatography using toluene as the developing solvent, and then the target product was obtained by recrystallization using a mixed solvent of toluene and hexane (yellowish-white solid, quantity 0.75 g, yield 37%). The synthesis scheme is shown in the following formula (l-1).

[0626] [Chemical Formula 80]

[0627]

[0628] In addition, nuclear magnetic resonance spectroscopy of the yellowish-white solid obtained above ( 1 The analysis results by H-NMR are shown below. In addition, 1 The H-NMR chart is shown in FIG. 46. From this result, it was found that in this embodiment, an organic compound 9mFDBtPNfpr represented by the structural formula (246) described above was obtained.

[0629] 1 H-NMR.δ(CD2Cl2): 1.47(s, 6H), 7.27-7.32(m, 2H), 7.38(d, 1H), 7.61-7.76(m, 8H), 7.79-7.85(m, 4H), 7.89(d, 1H), 8.08(d, 1H), 8.13(d, 1H), 8.24-8.31(m, 3H), 8.59(s, 1H), 9.14(d, 1H), 9.31(s, 1H).

[0630] (Example 17)

[0631] <<Synthesized Example 13>>

[0632] In this embodiment, a method for synthesizing an organic compound 11-(3-naphtho[1',2':4,5]furo[2,3-b]pyrazine-9-yl-phenyl)-12-phenylindolo[2,3-a]carbazole (abbreviated: 9mIcz(II)PNfpr), which is one form of the present invention represented by the structural formula (247) of Embodiment 1, is described. Additionally, the structure of 9mIcz(II)PNfpr is shown below.

[0633] [Chemical Formula 81]

[0634]

[0635] In addition, the synthesis method of 9mIcz(II)PNfpr is shown in the synthesis scheme of the following formula (m-1).

[0636] [Chemical Formula 82]

[0637]

[0638] (Example 18)

[0639] <<Synthesized Example 14>>

[0640] In this embodiment, a method for synthesizing the organic compound 3-naphtho[1',2':4,5]furo[2,3-b]pyrazine-9-yl-N,N-diphenylbenzeneamine (abbreviated as 9mTPANfpr), which is one form of the present invention represented by the structural formula (248) of Embodiment 1, is described. Additionally, the structure of 9mTPANfpr is shown below.

[0641] [Chemical Formula 83]

[0642]

[0643] In addition, the synthesis method of 9mTPANfpr is shown in the synthesis scheme of the following formula (n-1).

[0644] [Chemical Formula 84]

[0645]

[0646] (Example 19)

[0647] In this embodiment, as a light-emitting element of one form of the present invention, a light-emitting element 8 is fabricated using the 10mDBtBPNfpr (structural formula (133)) described in Example 9 in the light-emitting layer, and the results of measuring the characteristics thereof are described.

[0648] In addition, the device structure of light-emitting element 8 fabricated in this embodiment has the same structure as that of FIG. 11 referenced in Example 2, but the specific configuration of each layer constituting the device structure is as shown in Table 12. Also, the chemical formula of the material used in this embodiment is shown below.

[0649] [Table 12]

[0650]

[0651] * 10mDBtBPNfpr:PCBBiF:[Ir(dmpqn)2(acac)](0.75:0.25:0.1 40nm)

[0652] [Chemical Formula 85]

[0653]

[0654] <<Operating Characteristics of Light-Emitting Element 8>>

[0655] The operating characteristics of the fabricated light-emitting element 8 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0656] The current density-luminance characteristics of light-emitting element 8 are shown in Fig. 47, the voltage-luminance characteristics in Fig. 48, the luminance-current efficiency characteristics in Fig. 49, and the voltage-current characteristics in Fig. 50, respectively.

[0657] Also, 1000 cd / m² 2 The main initial characteristic values ​​of light-emitting element 8 in the vicinity are shown in Table 13 below.

[0658] [Table 13]

[0659]

[0660] In addition, 2.5 mA / cm² at light-emitting element 8 2 The emission spectrum when current is passed at a current density is shown in FIG. 51. As shown in FIG. 51, the emission spectrum of the light-emitting element has a peak around 626 nm and is suggested to originate from the emission of [Ir(dmpqn)2(acac)] included in the light-emitting layer (913).

[0661] Next, a reliability test was performed on light-emitting element 8. The results of the reliability test are shown in Fig. 52. In Fig. 52, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 75 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0662] As can be seen from the results of the reliability test, the light-emitting device 8 using the organic compound 10mDBtBPNfpr, which is one embodiment of the present invention, has high reliability. Therefore, it can be said that using the organic compound, which is one embodiment of the present invention, is useful for improving the reliability of the light-emitting device.

[0663] (Example 20)

[0664] In this embodiment, as a light-emitting element of one form of the present invention, a light-emitting element 9 is fabricated using the 12mDBtBPPnfpr (structural formula (208)) described in Example 11 in the light-emitting layer, and the results of measuring the characteristics thereof are described.

[0665] In addition, the device structure of the light-emitting element 9 fabricated in this embodiment has the same structure as that of FIG. 11 referenced in Example 2, but the specific configuration of each layer constituting the device structure is as shown in Table 14. Also, the chemical formula of the material used in this embodiment is shown below.

[0666] [Table 14]

[0667]

[0668] * 12mDBtBPPnfpr:PCBBiF:[Ir(dmpqn)2(acac)](0.75:0.25:0.1 40nm)

[0669] [Chemical Formula 86]

[0670]

[0671] <<Operating Characteristics of Light-Emitting Element 9>>

[0672] The operating characteristics of the fabricated light-emitting device 9 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0673] The current density-luminance characteristics of the light-emitting element 9 are shown in Fig. 53, the voltage-luminance characteristics in Fig. 54, the luminance-current efficiency characteristics in Fig. 55, and the voltage-current characteristics in Fig. 56, respectively.

[0674] Also, 1000 cd / m² 2 The main initial characteristic values ​​of the light-emitting element 9 in the vicinity are shown in Table 15 below.

[0675] [Table 15]

[0676]

[0677] In addition, 2.5 mA / cm² at light-emitting element 9 2 The emission spectrum when current is passed at a current density is shown in FIG. 57. As shown in FIG. 57, the emission spectrum of the light-emitting element has a peak around 626 nm and is suggested to originate from the emission of [Ir(dmpqn)2(acac)] contained in the light-emitting layer (913).

[0678] Next, a reliability test was performed on light-emitting element 9. The results of the reliability test are shown in Fig. 58. In Fig. 58, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 75 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0679] As can be seen from the results of the reliability test, the light-emitting device 9 using the organic compound 12mDBtBPPnfpr, which is one embodiment of the present invention, has high reliability. Therefore, it can be said that using the organic compound, which is one embodiment of the present invention, is useful for improving the reliability of the light-emitting device.

[0680] (Example 21)

[0681] In this embodiment, as a light-emitting element of one form of the present invention, a light-emitting element 10 using 9PCCzNfpr (structural formula (123)) described in Example 6 in the light-emitting layer, a light-emitting element 11 using 10PCCzNfpr (structural formula (156)) described in Example 10 in the light-emitting layer, a light-emitting element 12 using 9mPCCzPNfpr (structural formula (125)) described in Example 7 in the light-emitting layer, a light-emitting element 13 using 9mPCCzPNfpr-02 (structural formula (126)) described in Example 8 in the light-emitting layer, a light-emitting element 14 using 9pPCCzPNfpr (structural formula (238)) described in Example 12 in the light-emitting layer, and a light-emitting element 15 using 9pPCCzPNfpr-02 (structural formula (239)) described in Example 13 in the light-emitting layer are each fabricated, and the results of measuring their characteristics are described.

[0682] In addition, the device structures of light-emitting elements 10, emitting elements 11, emitting elements 12, emitting elements 13, emitting elements 14, and emitting elements 15 fabricated in this embodiment have the same structure as light-emitting element 3 described in Example 3, but the specific configuration of each layer constituting the device structure is as shown in Table 16. In addition, the chemical formulas of the materials used in this embodiment are shown below.

[0683] [Table 16]

[0684]

[0685] * 9PCCzNfpr:[Ir(dmpqn)2(acac)](1.0:0.1 40nm)

[0686] ** 10PCCzNfpr:[Ir(dmpqn)2(acac)](1.0:0.1 40nm)

[0687] *** 9mPCCzPNfpr:[Ir(dmpqn)2(acac)](1.0:0.1 40nm)

[0688] **** 9mPCCzPNfpr-02:[Ir(dmpqn)2(acac)](1.0:0.1 40nm)

[0689] ***** 9pPCCzPNfpr:[Ir(dmpqn)2(acac)](1.0:0.1 40nm)

[0690] ****** 9pPCCzPNfpr-02:[Ir(dmpqn)2(acac)](1.0:0.1 40nm)

[0691] [Chemical Formula 87]

[0692]

[0693] [Chemical Formula 88]

[0694]

[0695] <<Operating Characteristics of Light-Emitting Devices>>

[0696] The operating characteristics of the fabricated light-emitting elements 10, 11, 12, 13, 14, and 15 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0697] The current density-luminance characteristics of each light-emitting element are shown in Fig. 59, the voltage-luminance characteristics in Fig. 60, the luminance-current efficiency characteristics in Fig. 61, and the voltage-current characteristics in Fig. 62, respectively.

[0698] Also, 1000 cd / m² 2 The main initial characteristic values ​​of each light-emitting element in the vicinity are shown in Table 17 below.

[0699] [Table 17]

[0700]

[0701] In addition, 2.5 mA / cm² for each light-emitting element 2 The emission spectrum when current is passed at a current density is shown in FIG. 63. As shown in FIG. 63, the emission spectrum of the light-emitting element has a peak around 629 nm and is suggested to originate from the emission of [Ir(dmpqn)2(acac)] contained in the light-emitting layer (913).

[0702] Next, a reliability test was performed on each of the above-mentioned light-emitting elements. The results of the reliability test are shown in Fig. 64. In Fig. 64, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. In addition, for the reliability test, 75 mA / cm 2 A constant current driving test was performed by flowing a constant current at a current density.

[0703] As can be seen from the results of the reliability test, each light-emitting device using the organic compounds 9PCCzNfpr, 10PCCzNfpr, 9mPCCzPNfpr, 9mPCCzPNfpr-02, 9pPCCzPNfpr, and 9pPCCzPNfpr-02, which are one embodiment of the present invention, in each light-emitting layer has high reliability. Therefore, it can be said that using the organic compounds of one embodiment of the present invention is useful for improving the reliability of the light-emitting device.

[0704] (Example 22)

[0705] <<Synthesized Example 15>>

[0706] In this embodiment, a method for synthesizing the organic compound 10-[4-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 10mPCCzPNfpr), which is one form of the present invention represented by the structural formula (158) of Embodiment 1, is described. Additionally, the structure of 10mPCCzPNfpr is shown below.

[0707] [Chemical Formula 89]

[0708]

[0709] In addition, the synthesis method of 10mPCCzPNfpr is shown in the synthesis schemes of the following formulas (o-1) to (o-4).

[0710] [Chemical Formula 90]

[0711]

[0712] [Chemical Formula 91]

[0713]

[0714] [Chemical Formula 92]

[0715]

[0716] [Chemical Formula 93]

[0717]

[0718] (Example 23)

[0719] <<Synthesized Example 16>>

[0720] In this embodiment, a method for synthesizing the organic compound 11-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]phenantro[9',10':4,5]furo[2,3-b]pyrazine (abbreviated: 11mDBtBPPnfpr), which is one form of the present invention represented by the structural formula (178) of Embodiment 1, is described. Additionally, the structure of 11mDBtBPPnfpr is shown below.

[0721] [Chemical Formula 94]

[0722]

[0723] In addition, the synthesis method of 11mDBtBPPnfpr is shown in the synthesis schemes of the following formulas (p-1) to (p-7).

[0724] [Chemical Formula 95]

[0725]

[0726] [Chemical Formula 96]

[0727]

[0728] [Chemical Formula 97]

[0729]

[0730] [Chemical Formula 98]

[0731]

[0732] [Chemical Formula 99]

[0733]

[0734] [Chemical Formula 100]

[0735]

[0736] [Chemical Formula 101]

[0737]

[0738] (Example 24)

[0739] <<Synthesized Example 17>>

[0740] In this embodiment, a method for synthesizing the organic compound 10-[3-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 10pPCCzPNfpr), which is one form of the present invention represented by the structural formula (240) of Embodiment 1, is described. Additionally, the structure of 10pPCCzPNfpr is shown below.

[0741] [Chemical Formula 102]

[0742]

[0743] In addition, the synthesis method of 10pPCCzPNfpr is shown in the synthesis schemes of the following formulas (q-1) to (q-4).

[0744] [Chemical Formula 103]

[0745]

[0746] [Chemical Formula 104]

[0747]

[0748] [Chemical Formula 105]

[0749]

[0750] [Chemical Formula 106]

[0751]

[0752] (Example 25)

[0753] <<Synthesized Example 18>>

[0754] In this embodiment, a method for synthesizing the organic compound 9-[3-(7H-dibenzo[c,g]carbazole-7-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mcgDBCzPNfpr), which is one form of the present invention represented by the structural formula (242) of Embodiment 1, is described. Additionally, the structure of 9mcgDBCzPNfpr is shown below.

[0755] [Chemical Formula 107]

[0756]

[0757] In addition, the synthesis method of 9mcgDBCzPNfpr is shown in the synthesis schemes of formulas (r-1) to (r-4) below.

[0758] [Chemical Formula 108]

[0759]

[0760] [Chemical Formula 109]

[0761]

[0762] [Chemical Formula 110]

[0763]

[0764] [Chemical Formula 111]

[0765]

[0766] (Example 26)

[0767] <<Synthesized Example 19>>

[0768] In this embodiment, a method for synthesizing the organic compound 9-{3'-[6-(biphenyl-3-yl)dibenzothiophen-4-yl]biphenyl-3-yl}naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mDBtBPNfpr-03), which is one form of the present invention represented by the structural formula (249) of Embodiment 1, is described. Additionally, the structure of 9mDBtBPNfpr-03 is shown below.

[0769] [Chemical Formula 112]

[0770]

[0771] In addition, the synthesis method of 9mDBtBPNfpr-03 is shown in the synthesis schemes of the following formulas (s-1) to (s-4).

[0772] [Chemical Formula 113]

[0773]

[0774] [Chemical Formula 114]

[0775]

[0776] [Chemical Formula 115]

[0777]

[0778] [Chemical Formula 116]

[0779]

[0780] (Example 27)

[0781] <<Synthesized Example 20>>

[0782] In this embodiment, a method for synthesizing the organic compound 9-{3'-[6-(biphenyl-4-yl)dibenzothiophen-4-yl]biphenyl-3-yl}naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated: 9mDBtBPNfpr-04), which is one form of the present invention represented by the structural formula (250) of Embodiment 1, is described. Additionally, the structure of 9mDBtBPNfpr-04 is shown below.

[0783] [Chemical Formula 117]

[0784]

[0785] In addition, the synthesis method of 9mDBtBPNfpr-04 is shown in the synthesis schemes of the following formulas (t-1) to (t-4).

[0786] [Chemical Formula 118]

[0787]

[0788] [Chemical Formula 119]

[0789]

[0790] [Chemical Formula 120]

[0791]

[0792] [Chemical Formula 121]

[0793]

[0794] (Example 28)

[0795] <<Synthesized Example 21>>

[0796] In this embodiment, a method for synthesizing an organic compound 11-[3'-(6-phenyldibenzothiophen-4-yl)biphenyl-3-yl]phenantro[9',10':4,5]furo[2,3-b]pyrazine (abbreviated: 11mDBtBPPnfpr-02), which is one form of the present invention represented by the structural formula (251) of Embodiment 1, is described. Additionally, the structure of 11mDBtBPPnfpr-02 is shown below.

[0797] [Chemical Formula 122]

[0798]

[0799] In addition, the synthesis method of 11mDBtBPPnfpr-02 is shown in the synthesis schemes of the following formulas (u-1) to (u-7).

[0800] [Chemical Formula 123]

[0801]

[0802] [Chemical Formula 124]

[0803]

[0804] [Chemical Formula 125]

[0805]

[0806] [Chemical Formula 126]

[0807]

[0808] [Chemical Formula 127]

[0809]

[0810] [Chemical Formula 128]

[0811]

[0812] [Chemical Formula 129]

[0813]

[0814] (Example 29)

[0815] In this embodiment, as a light-emitting element of one form of the present invention, a light-emitting element 16 is fabricated using 12mDBtBPPnfpr (structural formula (208)) described in Example 11 in the light-emitting layer, and a comparative light-emitting element 17 is fabricated using 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated: 2mDBTBPDBq-II) in the light-emitting layer as a comparative light-emitting element, and the results of measuring the characteristics of these are described.

[0816] In addition, the device structure of the light-emitting element 16 and the comparative light-emitting element 17 fabricated in this embodiment has the same structure as that of FIG. 11 referenced in Example 2, but the specific configuration of each layer constituting the device structure is as shown in Table 18. In addition, the chemical formula of the material used in this embodiment is shown below.

[0817] [Table 18]

[0818]

[0819] * 12mDBtBPPnfpr:PCBBiF:[Ir(dppm)2(acac)](0.75:0.25:0.075 40nm)

[0820] ** 2mDBTBPDBq-II:PCBBiF:[Ir(dppm)2(acac)](0.75:0.25:0.075 40nm)

[0821] [Chemical Formula 130]

[0822]

[0823] <<Operating Characteristics of Light-Emitting Devices>>

[0824] The operating characteristics of the fabricated light-emitting device 16 and the comparison light-emitting device 17 were measured. In addition, the measurements were performed at room temperature (an atmosphere maintained at 25℃).

[0825] The current density-luminance characteristics of light-emitting element 16 and comparison light-emitting element 17 are shown in Fig. 65, the voltage-luminance characteristics in Fig. 66, the luminance-current efficiency characteristics in Fig. 67, and the voltage-current characteristics in Fig. 68, respectively.

[0826] Also, 1000 cd / m² 2 The main initial characteristic values ​​of the light-emitting element 16 and the comparison light-emitting element 17 in the vicinity are shown in Table 19 below.

[0827] [Table 19]

[0828]

[0829] In addition, 2.5 mA / cm² for each light-emitting element 2 The emission spectrum when current is passed at a current density is shown in FIG. 69. As shown in FIG. 69, the emission spectrum of each emitting element has a peak around 586 nm and is suggested to originate from the emission of [Ir(dppm)2(acac)] contained in the emitting layer (913).

[0830] Next, reliability tests were performed on each light-emitting element. The results of the reliability tests are shown in Fig. 70. In Fig. 70, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. Additionally, for the reliability test, 75 mA / cm² 2 A constant current driving test was performed by flowing a constant current at a current density.

[0831] As can be seen from the results of the reliability test, the light-emitting device 16 using the organic compound 12mDBtBPPnfpr, which is one embodiment of the present invention, has higher reliability than the comparative light-emitting device 17 using 2mDBTBPDBq-II. This is thought to be due to the difference in the molecular structures of 12mDBtBPPnfpr and 2mDBTBPDBq-II, namely the difference between the phenantropuropyrazine backbone and the dibenzoquinoxaline backbone, and thus indicates the robustness of the puropyrazine derivative of one embodiment of the present invention. Therefore, using the organic compound of one embodiment of the present invention can be said to be useful for improving the reliability of the light-emitting device. Explanation of the symbols

[0832] 101: First electrode 102: Second electrode 103: EL layer 103a, 103b, 103c: EL layer 104: Charge generation layer 111, 111a, 111b: Hole injection layer 112, 112a, 112b: Hole transport layer 113, 113a, 113b, 113c: Emissive layer 114, 114a, 114b: Electron transport layer 115, 115a, 115b: Electron injection layer 200R, 200G, 200B: Optical distance 201: First substrate 202: Transistor (FET) 203R, 203G, 203B, 203W: Light-emitting elements 204: EL layer 205: Second substrate 206R, 206G, 206B: Color Filters 206R', 206G', 206B': Color Filters 207: First electrode 208: Second electrode 209: Black Matrix 210R, 210G: Challenge layer 301: First substrate 302: Pixel section 303: Driving circuit section (source line driving circuit) 304a, 304b: Driving circuit section (gate wire driving circuit) 305: Reality 306: Second substrate 307: Lead wiring 308: FPC 309: FET 310: FET 311: FET 312: FET 313: First electrode 314: Insulator 315: EL layer 316: Second electrode 317: Light-emitting element 318: Space 900: Board 901: First electrode 902: EL layer 903: Second electrode 911: Hole injection layer 912: Precision Transport Layer 913: Emissive layer 914: Electron transport layer 915: Electron injection layer 4000: Lighting device 4001: Board 4002: Light-emitting element 4003: Board 4004: First electrode 4005: EL layer 4006: Second electrode 4007: Electrode 4008: Electrode 4009: Auxiliary Wiring 4010: Insulating layer 4011: Sealed substrate 4012: Reality 4013: Desiccant 4015: Diffusion plate 4100: Lighting device 4200: Lighting device 4201: Board 4202: Light-emitting element 4204: First electrode 4205: EL layer 4206: Second electrode 4207: Electrode 4208: Electrode 4209: Auxiliary Wiring 4210: Insulating layer 4211: Sealing substrate 4212: Reality 4213: Barrier 4214: Flattening film 4215: Diffusion Plate 4300: Lighting device 5101: Light 5102: Tire wheel 5103: Door 5104: Display unit 5105: Handle 5106: Shift Lever 5107: Seat Seat 5108: inner rearview mirror 7000: Housing 7001: Display unit 7002: Second display unit 7003: Speaker 7004: LED lamp 7005: Control Keys 7006: Connection terminal 7007: Sensor 7008: Microphone 7009: Switch 7010: Infrared port 7011: Recording medium reader 7012: Jijibu 7013: Earphones 7014: Antenna 7015: Shutter button 7016: Award Division 7018: Stand 7019: Microphone 7020: Camera 7021: External connection part 7022, 7023: Control buttons 7024: Connection terminal 7025: Band 7026: Buckle 7027: Icon indicating the time 7028: Other icons 8001: Lighting devices 8002: Lighting device 8003: Lighting device 8004: Lighting device 9310: Portable Information Terminal 9311: Display unit 9312: Display area 9313: Hinge 9315: Housing

Claims

Claim 1 A light-emitting device comprising a light-emitting layer, wherein the light-emitting layer comprises a light-emitting material, a first organic compound represented by the following formula (G1), and a second organic compound which is a hole transport material. In the above equation (G1), Q represents oxygen, and Ar 1 represents unsubstituted naphthalene or unsubstituted phenanthrene, and R 2 represents hydrogen, and R 1 is a unit represented by the following equation (u1), and In the above formula (u1), α represents a phenylene group, n represents an integer from 0 to 2, and A 1 represents any one of a substituted or unsubstituted dibenzothiophen backbone, a substituted or unsubstituted dibenzofuran backbone, and a substituted or unsubstituted carbazole backbone, where, A 1 In the case of the above-mentioned substituted dibenzothiophen backbone, the above-mentioned substituted dibenzofuran backbone, or the above-mentioned substituted carbazole backbone, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms, and * represents the linkage portion in the above-mentioned formula (G1). Claim 2 A light-emitting device comprising a light-emitting layer, wherein the light-emitting layer comprises a light-emitting material, a first organic compound represented by the following formula (G1), and a second organic compound which is a hole transport material and forms an excited complex with the first organic compound. In the above equation (G1), Q represents oxygen, and Ar 1 represents unsubstituted naphthalene or unsubstituted phenanthrene, and R 1 and R 2 One of them is a unit represented by the following equation (u1), and In the above formula (u1), α represents a phenylene group, n represents an integer from 0 to 2, and A 1 represents any one of a substituted or unsubstituted dibenzothiophen backbone, a substituted or unsubstituted dibenzofuran backbone, and a substituted or unsubstituted carbazole backbone, where, A 1 In the case of representing the above-mentioned substituted dibenzothiophen backbone, the above-mentioned substituted dibenzofuran backbone, or the above-mentioned substituted carbazole backbone, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms, * indicates a linkage in the above-mentioned formula (G1), and R 1 and R 2 Another one represents hydrogen. Claim 3 delete Claim 4 In claim 1 or 2, Ar in the above formula (G1) 1 A light-emitting device that is either of the following equations (t1) and (t3). In the above equations (t1) and (t3), R 3 to R 8 and R 17 to R 24 Each represents hydrogen, and * represents the bonding part in the above formula (G1). Claim 5 A light-emitting device according to claim 1 or 2, wherein the formula (G1) is any one of the following formulas (G1-1) to (G1-4). In the above equations (G1-1) to (G1-4), R 3 to R 8 and R 17 to R 24 Each represents hydrogen. Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 In claim 1 or 2, A in the above formula (u1) 1 is the following formula (A 1 -11) or formula (A 1 -17) A light-emitting device, which is one of the following. The above formula (A 1 -11) or formula (A 1 In -17), R A1 to R A8 It independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms. Claim 10 delete Claim 11 A light-emitting device according to claim 1 or 2, wherein n in the formula (u1) represents an integer of 1 or 2. Claim 12 delete Claim 13 A light-emitting device comprising a light-emitting layer, wherein the light-emitting layer comprises a light-emitting material, a first organic compound, and a second organic compound which is a hole transport material, wherein the first organic compound is represented by any one of structural formula (100), structural formula (123), structural formula (125), structural formula (126), structural formula (133), structural formula (156), structural formula (208), structural formula (238), structural formula (239), structural formula (244), structural formula (245), structural formula (246), structural formula (247), structural formula (158), structural formula (178), structural formula (240), structural formula (242), structural formula (249), structural formula (250), and structural formula (251). Claim 14 A light-emitting device according to claim 13, wherein the first organic compound and the second organic compound form an excited complex. Claim 15 A light-emitting device according to any one of claims 1, 2, and 13, wherein the light-emitting material is any one of a fluorescent material, a phosphorescent material, and a thermally activated delayed fluorescent material. Claim 16 A composite material comprising a first organic compound represented by the following formula (G1) and a second organic compound which is a hole transport material. In the above equation (G1), Q represents oxygen, and Ar 1 represents unsubstituted naphthalene or unsubstituted phenanthrene, and R 2 represents hydrogen, and R 1 is a unit represented by the following equation (u1), and In the above formula (u1), α represents a phenylene group, n represents an integer from 0 to 2, and A 1 represents any one of a substituted or unsubstituted dibenzothiophen backbone, a substituted or unsubstituted dibenzofuran backbone, and a substituted or unsubstituted carbazole backbone, where, A 1 In the case of the above-mentioned substituted dibenzothiophen backbone, the above-mentioned substituted dibenzofuran backbone, or the above-mentioned substituted carbazole backbone, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms, and * represents the linkage portion in the above-mentioned formula (G1). Claim 17 A composite material comprising a first organic compound represented by the following formula (G1), and a second organic compound which is a hole transport material and forms an excited complex with the first organic compound. In the above equation (G1), Q represents oxygen, and Ar 1 represents unsubstituted naphthalene or unsubstituted phenanthrene, and R 1 and R 2 One of them is a unit represented by the following equation (u1), and In the above formula (u1), α represents a phenylene group, n represents an integer from 0 to 2, and A 1 represents any one of a substituted or unsubstituted dibenzothiophen backbone, a substituted or unsubstituted dibenzofuran backbone, and a substituted or unsubstituted carbazole backbone, where, A 1 In the case of representing the above-mentioned substituted dibenzothiophen backbone, the above-mentioned substituted dibenzofuran backbone, or the above-mentioned substituted carbazole backbone, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms, * indicates a linkage in the above-mentioned formula (G1), and R 1 and R 2 Another one represents hydrogen. Claim 18 In claim 16 or 17, the composite material is a composite material for a light-emitting element.

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