Organic Compounds and Light Emitting Devices

Abstract

To provide a novel benzofuropyridazine derivative and to provide a light-emitting device using the compound, and the like.SOLUTION: There is provided an organic compound represented by the following formula. In the formula, Q represents O or S; A is a group having the total carbon number of 12 to 100 and is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring or the like; and R1 to R5 each independently represent H, a 1-6C alkyl group, a 5-7C monocyclic saturated hydrocarbon, a 7-10C polycyclic saturated hydrocarbon, a 6-13C aryl group or a 3-12C heteroaryl group.SELECTED DRAWING: None

Description

[Technical field]

[0001] An aspect of the present invention relates to an organic compound, a light-emitting device, a light-emitting apparatus, an electronic device, and a lighting apparatus. However, an aspect of the present invention is not limited to the above technical fields. That is, an aspect of the present invention relates to an object, a method, a manufacturing method, or a driving method. Alternatively, an aspect of the present invention relates to a process, a machine, a manufacture, or a composition of matter. In addition, specifically, examples of the present invention include a semiconductor device, a display device, and a liquid crystal display device. [Background technology]

[0002] Light-emitting devices (also known as organic EL elements), which consist of an EL layer sandwiched between a pair of electrodes, have properties such as being thin and lightweight, having fast response to input signals, and consuming low power. As a result, displays that use these elements are being developed at a rapid pace and are attracting a great deal of attention.

[0003] In a light-emitting device, when a voltage is applied between a pair of electrodes, electrons and holes injected from each electrode recombine in the EL layer, causing the light-emitting substance (organic compound) contained in the EL layer to enter an excited state, and light is emitted when the excited state returns to the ground state. There are two types of excited states: singlet excited state (S * ) and triplet excited states (T * ) Emission from the singlet excited state is called fluorescence, and emission from the triplet excited state is called phosphorescence. The statistical generation ratio of these in a light-emitting device is S * :T * = 1: 3. The emission spectrum obtained from a luminescent material is specific to that material, and by using different types of organic compounds as luminescent materials, it is possible to obtain light-emitting devices that emit light of a variety of colors.

[0004] In order to improve the characteristics of such light-emitting devices, improvements to element structures and material development have been actively carried out (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2010-182699 A Summary of the Invention [Problem to be solved by the invention]

[0006] Therefore, in one embodiment of the present invention, a novel organic compound is provided. In another embodiment of the present invention, a novel organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton is provided. In another embodiment of the present invention, a novel organic compound that can be used in a light-emitting device is provided. In another embodiment of the present invention, a novel organic compound that can be used in an EL layer of a light-emitting device is provided. In addition, a novel light-emitting device with high reliability using the novel organic compound according to 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. Note that the description of these problems does not preclude the existence of other problems. Note that one embodiment of the present invention does not necessarily need to solve all of these problems. Note that problems other than these will become apparent from the description of the specification, drawings, claims, and the like, and it is possible to extract other problems from the description of the specification, drawings, claims, and the like. [Means for solving the problem]

[0007] One embodiment of the present invention is a benzofuropyridazine derivative, which is an organic compound represented by the following general formula (G1): The organic compound represented by the following general formula (G1) has a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton.

[0008] [ka]

[0009] In the above general formula (G1), Q represents oxygen or sulfur. A represents a group having a total of 12 to 100 carbon atoms, and has one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. R 1 ~R 5 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0010] Another embodiment of the present invention is a benzofuropyridazine derivative, which is an organic compound represented by the following general formula (G2): As represented by the following general formula (G2), the benzofuro[3,2-c]pyridazine skeleton or the benzothieno[3,2-c]pyridazine skeleton has a hole-transporting skeleton at the 3-position.

[0011] [ka]

[0012] In the above general formula (G2), Q represents oxygen or sulfur, α represents a substituted or unsubstituted phenylene group, and n represents an integer of 0 to 4. uni represents a skeleton having hole transport properties. 1 ~R 5 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0013] Another embodiment of the present invention is a benzofuropyridazine derivative, which is an organic compound represented by the following general formula (G3): As represented by the following general formula (G3), the benzofuro[3,2-c]pyridazine skeleton or the benzothieno[3,2-c]pyridazine skeleton has a hole-transporting skeleton at the 3-position.

[0014] [ka]

[0015] In the above general formula (G3), Q represents oxygen or sulfur. uni represents a skeleton having hole transport properties. 1 ~R 5 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0016] In each of the above structures, Ht uni each independently has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure.

[0017] In each of the above structures, Ht uni are each independently represented by any one of the following general formulas (Ht-1) to (Ht-26).

[0018] [ka]

[0019] [ka]

[0020] In the above general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. 2 ~R 71 Each of the groups represents 1 to 4 substituents, and each of the groups independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0021] Another embodiment of the present invention is an organic compound represented by any one of structural formulas (100) and (101).

[0022] [ka]

[0023] Another embodiment of the present invention is a light-emitting device using the organic compound according to one embodiment of the present invention. The present invention also includes a light-emitting device having a guest material in addition to the organic compound.

[0024] Another embodiment of the present invention is a light-emitting device using the organic compound according to one embodiment of the present invention. The present invention also includes a light-emitting device formed by using an organic compound according to one embodiment of the present invention in an EL layer between a pair of electrodes or in a light-emitting layer included in the EL layer. In addition to the above light-emitting devices, a light-emitting device having a layer (e.g., a cap layer) having an organic compound in contact with an electrode is also included in the light-emitting device and is included in the present invention. In addition to light-emitting devices, light-emitting devices having transistors, substrates, and the like are also included in the scope of the present invention. In addition to these light-emitting devices, electronic devices and lighting devices having a microphone, a camera, an operation button, an external connection part, a housing, a cover, a support, a speaker, and the like are also included in the scope of the present invention.

[0025] One embodiment of the present invention includes a light-emitting device having a light-emitting device, and further includes a lighting device having a light-emitting device in its category. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). In addition, the light-emitting device includes a module in which a connector such as an FPC (flexible printed circuit) or a TCP (tape carrier package) is attached to a light-emitting device, a module in which a printed wiring board is provided at the end of a TCP, or a module in which an IC (integrated circuit) is directly mounted on a light-emitting device by a COG (chip on glass) method. Effect of the Invention

[0026] According to one embodiment of the present invention, a novel organic compound can be provided. According to another embodiment of the present invention, a novel organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton can be provided. According to another embodiment of the present invention, a novel organic compound that can be used in a light-emitting device can be provided. According to another embodiment of the present invention, a novel organic compound that can be used in an EL layer of a light-emitting device can be provided. Furthermore, by using the novel organic compound according to one embodiment of the present invention, a novel light-emitting device with high reliability can be provided. Furthermore, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. [Brief description of the drawings]

[0027] [Figure 1] FIG. 1(A), FIG. 1(B), FIG. 1(C), FIG. 1(D), and FIG. 1(E) are diagrams for explaining the structure of a light-emitting device. [Diagram 2] Fig. 2(A) is a diagram for explaining a light emitting device, Fig. 2(B) is a diagram for explaining a light emitting device, and Fig. 2(C) is a diagram for explaining a light emitting device. [Diagram 3] Fig. 3(A) is a top view illustrating the light emitting device, and Fig. 3(B) is a cross-sectional view illustrating the light emitting device. [Figure 4] FIG. 4(A) is a diagram illustrating a mobile computer. FIG. 4(B) is a diagram illustrating a portable image playback device. FIG. 4(C) is a diagram illustrating a digital camera. FIG. 4(D) is a diagram illustrating a portable information terminal. FIG. 4(E) is a diagram illustrating a portable information terminal. FIG. 4(F) is a diagram illustrating a television device. FIG. 4(G) is a diagram illustrating a portable information terminal. [Diagram 5] Fig. 5(A) is a diagram for explaining an electronic device, Fig. 5(B) is a diagram for explaining an electronic device, and Fig. 5(C) is a diagram for explaining an electronic device. [Figure 6] Fig. 6(A) is a diagram for explaining an automobile, and Fig. 6(B) is a diagram for explaining an automobile. [Figure 7] Fig. 7(A) is a diagram for explaining an illumination device, and Fig. 7(B) is a diagram for explaining an illumination device. [Figure 8] FIG. 8 is a 1H-NMR chart of the organic compound represented by the structural formula (100). [Figure 9] FIG. 9 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by the structural formula (100). [Figure 10] FIG. 10 is a phosphorescence spectrum of the organic compound represented by the structural formula (100). [Figure 11] FIG. 11 is a 1H-NMR chart of the organic compound represented by the structural formula (101). [Figure 12] FIG. 12 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organic compound represented by the structural formula (101). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0028] Hereinafter, the embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and the form and details can be changed in various ways without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below.

[0029] In addition, for ease of understanding, the position, size, range, etc. of each component shown in the drawings, etc. may not represent the actual position, size, range, etc. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings, etc.

[0030] In addition, in this specification and the like, when describing the configuration of the invention using drawings, the same reference numerals are used in common between different drawings.

[0031] (Embodiment 1) In this embodiment, an organic compound according to one embodiment of the present invention will be described. The organic compound according to one embodiment of the present invention is an organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton represented by the following general formula (G1).

[0032] [ka]

[0033] In the general formula (G1), Q represents oxygen or sulfur. A represents a group having a total of 12 to 100 carbon atoms, and has one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. 1 ~R 5each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0034] Another embodiment of the present invention is an organic compound represented by the following general formula (G2): The organic compound according to one embodiment of the present invention has a hole-transporting skeleton at the 3-position of a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton as represented by the following general formula (G2).

[0035] [ka]

[0036] In the above general formula (G2), Q represents oxygen or sulfur, α represents a substituted or unsubstituted phenylene group, and n represents an integer of 0 to 4. uni represents a skeleton having hole transport properties. 1 ~R 5 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0037] Another embodiment of the present invention is an organic compound represented by the following general formula (G3): The organic compound according to one embodiment of the present invention has a hole-transporting skeleton at the 3-position of a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton as represented by the following general formula (G3).

[0038] [ka]

[0039] In the above general formula (G3), Q represents oxygen or sulfur. uni represents a skeleton having hole transport properties. 1 ~R 5 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0040] In addition, Ht in the above general formulas (G2) and (G3) uni each independently has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure.

[0041] In addition, Ht in the above general formulas (G2) and (G3) uni are each independently represented by any one of the following general formulas (Ht-1) to (Ht-26).

[0042] [ka]

[0043] [ka]

[0044] In the above general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. 2 ~R 71 Each of the groups represents 1 to 4 substituents, and each of the groups independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

[0045] In addition, in the above general formulae (G1), (G2), and (G3), when the substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, the substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, the substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or the substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms has a substituent, examples of the substituent include 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 a 8,9,10-trinorbornanyl group; an aryl group having 6 to 12 carbon atoms such as a phenyl group, a naphthyl group, or a biphenyl group; and a heteroaryl group having 6 to 13 carbon atoms such as a dibenzothiophenyl group, a dibenzofuranyl group, or a carbazolyl group.

[0046] In addition, R in the above general formulae (G1), (G2), and (G3) 1 ~R 5 When represents a monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, specific examples include a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, and a cycloheptyl group.

[0047] In addition, R in the above general formulae (G1), (G2), and (G3) 1 ~R 5 When represents a polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, specific examples include a norbornyl group, an adamantyl group, a decalin group, and a tricyclodecyl group.

[0048] In addition, R in the above general formulae (G1), (G2), and (G3) 1 ~R 5 Specific examples of the aryl group having 6 to 13 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, a 2-naphthyl group, and a fluorenyl group.

[0049] In addition, R in the above general formulae (G1), (G2), and (G3) 1 ~R 5 Specific examples of when represents an alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, a 2,3-dimethylbutyl group, and the like.

[0050] In addition, R in the above general formulae (G1), (G2), and (G3) 1 ~R 5 Specific examples of when represents a heteroaryl group having 3 to 12 carbon atoms include a triazinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a benzothienyl group, a benzofuranyl group, an indolyl group, a dibenzothienyl group, a dibenzofuranyl group, and a carbazolyl group.

[0051] In addition, R in the above general formulae (G1), (G2), and (G3) 1 ~R 5 However, by having the groups represented by the specific examples above, the organic compound according to one embodiment of the present invention has high thermal stability and physicochemical stability. 3 However, when the material has a group as shown in the specific examples above, the thermal stability is improved due to the structure, and the LUMO is stabilized, resulting in high electron tolerance. Therefore, by using this material to fabricate a light-emitting device, a highly reliable light-emitting device can be obtained.

[0052] Next, specific structural formulae of the organic compounds according to embodiments of the present invention will be shown below, although the present invention is not limited thereto.

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] Note that the organic compounds represented by the structural formulas (100) to (121) above are examples of the organic compounds represented by the general formula (G1) above, but the organic compounds which are embodiments of the present invention are not limited thereto.

[0057] <Method for synthesizing organic compound represented by general formula (G1)> Next, a method for synthesizing an organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton, which is one embodiment of the present invention and is represented by the following general formula (G1), will be described.

[0058] [ka]

[0059] In the general formula (G1), Q represents oxygen or sulfur. A represents a group having a total of 12 to 100 carbon atoms and has one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. 1 ~R 5 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0060] The synthesis scheme (A) of the organic compound represented by the above general formula (G1) is shown below. The compound represented by the general formula (G1) can be obtained by reacting a halogen compound (A1) having a benzofuropyridazine skeleton or a benzothienopyridazine skeleton with a boronic acid compound (A2) and a boronic acid compound (A3), as shown in the synthesis scheme (A) below.

[0061] [ka]

[0062] In the synthesis scheme (A), Q represents oxygen or sulfur. A represents a group having a total of 12 to 100 carbon atoms and has one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. 1 ~R 5 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 1 , X 2 represents a halogen, preferably chlorine, bromine or iodine. 1 , Y 2 represents a boronic acid, a boronic acid ester, a cyclic triol borate salt, etc. In addition to the lithium salt, the cyclic triol borate salt may also be a potassium salt or a sodium salt.

[0063] The halogen compound (A1) used in the above synthesis scheme (A) is R 1When is hydrogen, it can be synthesized as shown in the following synthesis scheme (B). That is, intermediate (B3) can be obtained by reacting halogenated benzofuran-3-one derivative or benzothiophen-3-one derivative (B1) with glyoxylic acid ester (B2), and then intermediate (B4) can be obtained by reacting with hydrazine monohydrate. By reacting this intermediate (B4) with a halogenating agent, halogenated compound (A1) having a benzofuropyridazine skeleton or benzothienopyridazine skeleton can be synthesized.

[0064] [ka]

[0065] In the above synthesis scheme (B), Q represents oxygen or sulfur. 1 , X 2 represents a halogen, preferably chlorine, bromine or iodine. 6 represents an alkyl group, preferably a methyl group or an ethyl group. The glyoxylic acid ester (B2) may be prepared in a solution or in a polymer form.

[0066] The halogen compound (A1) used in the synthesis scheme (A) can also be synthesized by the method shown in the following synthesis scheme (C) by cyclizing an intermediate (C3) obtained by reacting a dihalogen compound (C1) with a pyridazine compound (C2) substituted with a hydroxyl group or a sulfanyl group.

[0067] [ka]

[0068] In the synthesis scheme (C), Q represents oxygen or sulfur. 1 ~X 4 represents a halogen, and X 1 ~X 3 is preferably chlorine, bromine or iodine, X 4is preferably fluorine or chlorine.

[0069] Note that various types of the compounds (A1), (A2), (A3), (B1), (B2), (B3), (C1), (C2), and (C3) used in the above synthesis schemes (A) to (C) are commercially available or can be synthesized, so that many types of organic compounds represented by General Formula (G1) can be synthesized. Thus, the organic compounds of one embodiment of the present invention are abundant in variety.

[0070] Although an example of a method for synthesizing an organic compound according to one embodiment of the present invention has been described above, the present invention is not limited to this example, and any other synthesis method may be used for synthesis.

[0071] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiment modes.

[0072] (Embodiment 2) In this embodiment mode, a light-emitting device using the organic compound shown in Embodiment Mode 1 will be described with reference to FIG.

[0073] <Basic structure of light-emitting devices> First, the basic structure of a light-emitting device will be described. Figure 1(A) shows an example of a light-emitting device having an EL layer including a light-emitting layer between a pair of electrodes. Specifically, the device has a structure in which an EL layer 103 is sandwiched between a first electrode 101 and a second electrode 102.

[0074] 1B shows an example of a light-emitting device having a stacked structure (tandem structure) including a plurality of EL layers (103a, 103b) (two layers in FIG. 1B) between a pair of electrodes and a charge generating layer 104 between the EL layers. The number of stacked EL layers is not limited to two, and may be three or more.

[0075] The charge generation layer 104 has a function of injecting electrons into one EL layer (103a or 103b) and injecting holes into the other EL layer (103b or 103a) when a voltage is applied between the first electrode 101 and the second electrode 102. Therefore, in FIG. 1B, when a voltage is applied to the first electrode 101 so that the first electrode 101 has a higher potential than the second electrode 102, electrons are injected from the charge generation layer 104 into the EL layer 103a and holes are injected into the EL layer 103b.

[0076] From the viewpoint of light extraction efficiency, the charge generation layer 104 is preferably transparent to visible light (specifically, the visible light transmittance of the charge generation layer 104 is 40% or more). The charge generation layer 104 functions even if it has a lower conductivity than the first electrode 101 and the second electrode 102.

[0077] FIG. 1C shows an example of the case where the EL layer 103 shown in FIG. 1A (the same applies to the case where the EL layers (103a, 103b) in FIG. 1B have a stacked structure) has a stacked structure. In this case, however, 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 stacked in this order on the first electrode 101. Note that even in the case where a plurality of EL layers are provided as in the tandem structure shown in FIG. 1B, the EL layers are stacked in this order from the anode side as shown in FIG. 1D. 1D, each EL layer includes a hole injection layer (111a, 111b), a hole transport layer (112a, 112b), a light emitting layer (113a, 113b), an electron transport layer (114a, 114b), and an electron injection layer (115a, 115b). When the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order of the EL layers is reversed.

[0078] The light-emitting layer 113 included in the EL layer (103, 103a, 103b) may have a light-emitting substance or a combination of a plurality of substances, and may have a structure in which fluorescence or phosphorescence with a desired emission color can be obtained. The light-emitting layer 113 may have a stacked structure with different emission colors. In this case, different materials may be used as the light-emitting substance and other substances used in each stacked light-emitting layer. A structure in which different emission colors can be obtained from the plurality of EL layers (103a, 103b) shown in FIG. 1B may also be used. In this case, different materials may be used as the light-emitting substance and other substances used in each light-emitting layer. An organic compound which is one embodiment of the present invention can be used for the light-emitting layer 113.

[0079] In addition, in the light-emitting device according to one embodiment of the present invention, the light emitted from the EL layer (103, 103a, 103b) may be resonated between both electrodes to enhance the light emission. For example, in FIG. 1C, the first electrode 101 is a reflective electrode and the second electrode 102 is a semi-transmissive and semi-reflective electrode to form a micro-optical resonator (microcavity) structure, which enhances the light emission from the EL layer 103.

[0080] In addition, when the first electrode 101 of the light-emitting device is a reflective electrode having a laminated structure of a conductive material having reflectivity and a conductive material having light transmission (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. Specifically, it is preferable to adjust the inter-electrode distance between the first electrode 101 and the second electrode 102 to be approximately mλ / 2 (where m is a natural number) for the wavelength λ of the light obtained from the light-emitting layer 113.

[0081] 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) in the light-emitting layer 113 where the desired light is obtained, and the optical distance from the second electrode 102 to the region (light-emitting region) in the light-emitting layer 113 where the desired light is obtained, to be approximately (2m'+1)λ / 4 (where m' is a natural number). Note that the light-emitting region here refers to a recombination region of holes and electrons in the light-emitting layer 113.

[0082] By carrying out such optical adjustment, it is possible to narrow the spectrum of the specific monochromatic light obtained from the light-emitting layer 113, and to obtain light emission with good color purity.

[0083] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 can be strictly said to be the total thickness from the reflection area in the first electrode 101 to the reflection area in the second electrode 102. However, since it is difficult to strictly determine the reflection area in the first electrode 101 or the second electrode 102, it is assumed that the above-mentioned effect can be sufficiently obtained by assuming any position of the first electrode 101 or the second electrode 102 as the reflection area. Furthermore, the optical distance between the first electrode 101 and the light-emitting layer from which the desired light is obtained can be strictly said to be the optical distance between the reflection area in the first electrode 101 and the light-emitting area in the light-emitting layer from which the desired light is obtained. However, since it is difficult to strictly determine the reflection area in the first electrode 101 or the light-emitting area in the light-emitting layer from which the desired light is obtained, it is assumed that the above-mentioned effect can be sufficiently obtained by assuming any position of the first electrode 101 as the reflection area and any position of the light-emitting layer from which the desired light is obtained as the light-emitting area.

[0084] When the light-emitting device shown in Fig. 1(C) has a microcavity structure, it is possible to extract light of different wavelengths (monochromatic light) even if the EL layer is the same. Therefore, it is not necessary to paint different colors (e.g., RGB) to obtain different luminescent colors, and high definition is possible. It is also possible to combine it with a colored layer (color filter). In addition, it is possible to increase the luminescent intensity of a specific wavelength in the front direction, which allows for low power consumption.

[0085] The light-emitting device shown in FIG. 1(E) is an example of the light-emitting device having the stacked structure (tandem structure) shown in FIG. 1(B), and has a structure in which three EL layers (103a, 103b, 103c) are stacked with charge generating layers (104a, 104b) sandwiched therebetween, as shown in the figure. The three EL layers (103a, 103b, 103c) each have a light-emitting layer (113a, 113b, 113c), and the light-emitting colors of the light-emitting layers can be freely combined. For example, the light-emitting layer 113a can be blue, the light-emitting layer 113b can be red, green, or yellow, and the light-emitting layer 113c can be blue, but it is also possible to make the light-emitting layer 113a red, the light-emitting layer 113b blue, green, or yellow, and the light-emitting layer 113c red.

[0086] In the light-emitting device according to one embodiment of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is an electrode having translucency (such as a transparent electrode or a semi-transparent / semi-reflective electrode). When the electrode having translucency is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. When the electrode is a semi-transparent / semi-reflective electrode, the visible light reflectance of the semi-transparent / semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Furthermore, these electrodes have a resistivity of 1×10 -2 It is preferable to set it to Ωcm or less.

[0087] In the above-described light-emitting device according to one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%.-2 It is preferable to set it to Ωcm or less.

[0088] <Specific structure and manufacturing method of light-emitting device> Next, a specific structure and a manufacturing method of the light-emitting device shown in FIG. 1, which is one embodiment of the present invention, will be described. Here, not only the light-emitting devices in which the EL layer 103 has a single-layer structure as shown in FIG. 1(A) and FIG. 1(C), but also the light-emitting devices having a tandem structure as shown in FIG. 1(B), FIG. 1(D), and FIG. 1(E) will be described. When each light-emitting device shown in FIG. 1 has a microcavity structure, for example, the first electrode 101 may be formed as a reflective electrode, and the second electrode 102 may be formed as a semi-transmissive and semi-reflective electrode. In addition, a single or multiple desired electrode materials may be used to form a single layer or a stacked layer. In addition, the second electrode 102 is formed by selecting a material in the same manner as described above after forming the EL layers (103, 103b). In addition, a sputtering method or a vacuum deposition method may be used to manufacture these electrodes.

[0089] <First Electrode and Second Electrode> As the material for forming the first electrode 101 and the second electrode 102, the following materials can be used in appropriate combination as long as the above-mentioned functions of both electrodes are satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used appropriately. Specific examples include In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, and In-W-Zn oxide. 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), as well as alloys containing these in appropriate combinations, can also be used. Other examples that can be used include elements belonging to Group 1 or 2 of the periodic table (e.g., lithium (Li), cesium (Cs), calcium (Ca), and strontium (Sr)) that are not listed above, rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing appropriate combinations of these, as well as graphene.

[0090] In the light-emitting device shown in Fig. 1, when the EL layer 103 has a laminated structure as shown in Fig. 1(C) and the first electrode 101 is an anode, the hole injection layer 111 and the hole transport layer 112 of the EL layer 103 are laminated in sequence by a vacuum deposition method on the first electrode 101. In addition, when a plurality of EL layers (103a, 103b) having a laminated structure are laminated with the charge generation layer 104 sandwiched therebetween as shown in Fig. 1(D) and the first electrode 101 is an anode, not only are the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a laminated in sequence by a vacuum deposition method on the first electrode 101, but also, after the EL layer 103a and the charge generation layer 104 are laminated in sequence, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are similarly laminated in sequence on the charge generation layer 104.

[0091] <Hole injection layer and hole transport layer> The hole injection layers (111, 111a, 111b) are layers that inject holes from the first electrode 101, which is an anode, or the charge generation layer (104) to the EL layers (103, 103a, 103b), and contain a material with high hole injection properties.

[0092] Examples of materials with high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. 2 Pc) and copper phthalocyanine (abbreviation: CuPc) and other phthalocyanine-based compounds can be used.

[0093] In addition, the low molecular weight compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-( Aromatic amine compounds such as 4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) can be used.

[0094] Also, polymer compounds (oligomers, dendrimers, polymers, etc.) such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc. can be used. Alternatively, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), etc. can also be used.

[0095] In addition, a composite material containing a hole transport material and an acceptor material (electron accepting material) can also be used as a material with high hole injection properties. In this case, electrons are extracted from the hole transport material by the acceptor material, generating holes in the hole injection layer (111, 111a, 111b), and the holes are injected into the light emitting layer (113, 113a, 113b) through the hole transport layer (112, 112a, 112b). Note that the hole injection layer (111, 111a, 111b) may be formed as a single layer made of a composite material containing a hole transport material and an acceptor material (electron accepting material), or may be formed by laminating the hole transport material and the acceptor material (electron accepting material) in separate layers.

[0096] The hole transport layers (112, 112a, 112b) are layers that transport holes injected from the first electrode 101 by the hole injection layers (111, 111a, 111b) to the light emitting layers (113, 113a, 113b). The hole transport layers (112, 112a, 112b) are layers that contain a hole transport material. It is particularly preferable to use a hole transport material used for the hole transport layers (112, 112a, 112b) that has a HOMO level that is the same as or close to the HOMO level of the hole injection layers (111, 111a, 111b).

[0097] As an acceptor material used for the hole injection layers (111, 111a, 111b), an oxide of a metal belonging to Groups 4 to 8 of the periodic table can be used. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. As a material having an electron-withdrawing group (a halogen group or a cyano group), 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), etc. In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and preferable. In addition, radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group)[3] are preferred because they have very high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropane triylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropane triylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropane triylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile].

[0098] The hole transport material used in the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 112b) has a hole mobility of 1×10 -6 cm 2A substance having a hole mobility of / Vs or more is preferable. Note that other substances can be used as long as they have a higher hole transporting property than an electron transporting property.

[0099] As the hole transporting material, a material having a high hole transporting property, such as a π-electron-rich heteroaromatic compound (for example, a carbazole derivative or a furan derivative) or an aromatic amine (a compound having an aromatic amine skeleton), is preferable.

[0100] Examples of the carbazole derivatives (compounds having a carbazole skeleton) include bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives) and aromatic amines having a carbazolyl group.

[0101] Specific examples of bicarbazole derivatives (e.g., 3,3'-bicarbazole derivatives) include 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9,9'-bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole, 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), and 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCCP).

[0102] Specific examples of aromatic amines having a carbazolyl group include 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl] )phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), Phenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9 ,9-Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1- naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), 4,4',4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA), etc.

[0103] In addition to the above, examples of the carbazole derivative include 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 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), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), and 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA).

[0104] Specific examples of the furan derivative (compound having a furan skeleton) include compounds having a thiophene skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 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).

[0105] Specific examples of the aromatic amine include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl- 3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino] Spiro-9,9'-bifluorene (abbreviation: DPASF), 2,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro-9,9'-bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-M TDATA), N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), etc.

[0106] As the hole transporting material, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used.

[0107] However, the hole transport material is not limited to the above, and one or a combination of various known materials can be used as the hole transport material for the hole injection layers (111, 111a, 111b) and the hole transport layers (112, 112a, 112b). Each of the hole transport layers (112, 112a, 112b) may be formed of a plurality of layers. That is, for example, a first hole transport layer and a second hole transport layer may be laminated.

[0108] In the light-emitting device shown in Fig. 1, the light-emitting layers (113, 113a) are formed by vacuum deposition on the hole transport layers (112, 112a) of the EL layers (103, 103a). In the case of a light-emitting device having a tandem structure shown in Fig. 1(D), after the EL layer 103a and the charge generation layer 104 are formed, the light-emitting layer 113b is also formed by vacuum deposition on the hole transport layer 112b of the EL layer 103b.

[0109] <Light-emitting layer> The light-emitting layers (113, 113a, 113b, 113c) are layers containing light-emitting substances. As the light-emitting substances, substances that emit light of a color such as blue, purple, blue-purple, green, yellow-green, yellow, orange, or red are appropriately used. In addition, by using different light-emitting substances in the multiple light-emitting layers (113a, 113b, 113c), a structure that emits different light colors (for example, white light emission obtained by combining light-emitting colors that are complementary to each other) can be obtained. Furthermore, a single light-emitting layer may have a stacked structure containing different light-emitting substances.

[0110] The light-emitting layers (113, 113a, 113b, and 113c) may contain one or more organic compounds (host materials or the like) in addition to a light-emitting substance (guest material). As the one or more organic compounds, an organic compound according to one embodiment of the present invention, or one or both of a hole-transporting material and an electron-transporting material described in this embodiment can be used.

[0111] There are no particular limitations on the light-emitting substances that can be used in the light-emitting layers (113, 113a, 113b, 113c), and light-emitting substances that convert singlet excitation energy into emission in the visible light range, or light-emitting substances that convert triplet excitation energy (the energy difference between the ground state and the triplet excited state) into emission in the visible light range can be used.

[0112] Examples of other light-emitting substances include the following:

[0113] Examples of luminescent substances that convert singlet excitation energy into luminescence include substances that emit fluorescence (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, naphthalene derivatives, etc. Pyrene derivatives are particularly preferred because of their high luminescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N, N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), etc.

[0114] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)phenyl]- N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4' -(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-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-phenyl) N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), and the like can be used.

[0115] Furthermore, examples of luminescent substances that convert triplet excitation energy into luminescence include substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence.

[0116] Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), rare earth metal complexes, etc. Since each substance exhibits a different emission color (emission peak), an appropriate material is selected and used as needed.

[0117] Examples of phosphorescent materials that exhibit blue or green light and have an emission spectrum with a peak wavelength of 450 nm or more and 570 nm or less include the following substances.

[0118] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp) 3 ]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz) 3 ]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b) 3 ]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz) 3 ]), organometallic complexes with a 4H-triazole skeleton such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp) 3 ]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me) 3 ]), organometallic complexes with a 1H-triazole skeleton such as fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi) 3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me 3 Organometallic complexes with imidazole skeletons such as bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(CF 3 ppy) 2 (pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ] Examples include organometallic complexes with phenylpyridine derivatives having electron-withdrawing groups as ligands, such as iridium(III) acetylacetonate (abbreviation: FIr(acac)).

[0119] Examples of phosphorescent materials that exhibit green or yellow color and have an emission spectrum with a peak wavelength of 495 nm or more and 590 nm or less include the following substances.

[0120] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm) 3 ]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) 3 ]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm) 2 (acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) 2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm) 2 (acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm) 2 (acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp) 2 (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) 2 (Acac)]), an organometallic iridium complex having a pyrimidine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me 2 (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinate)iridium(III) (abbreviation: [Ir(mppr-iPr) 2 Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinato-N,C(acac)]) 2’ ) Iridium(III) (abbreviation: [Ir(ppy) 3 ]), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy) 2 (acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq) 2 (acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq) 3 ]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3 ]), bis(2-phenylquinolinato-N,C 2’) Iridium(III) acetylacetonate (abbreviation: [Ir(pq) 2 (acac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy) 2 (4dppy)]), organometallic iridium complexes with pyridine skeletons such as bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC], and bis(2,4-diphenyl-1,3-oxazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(dpo) 2 (acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir(p-PF-ph) 2 (acac)]), bis(2-phenylbenzothiazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(bt) 2 In addition to organometallic complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)]), 3 Examples of rare earth metal complexes include those described above.

[0121] Examples of phosphorescent materials that exhibit yellow or red color and have an emission spectrum with a peak wavelength of 570 nm or more and 750 nm or less include the following substances.

[0122] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm) 2(dpm)]), (dipivaloylmethanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm) 2 (acetylacetonato)bis(2,3,5-triphenylpyrazinate)iridium(III) (abbreviation: [Ir(tppr)]) 2 (acac)]), bis(2,3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [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-heptanedionato-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-heptanedionato-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2 (dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalinato-N,C 2’ ]Iridium(III) (abbreviation: [Ir(mpq) 2 (acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(dpq) 2 (acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) 2 Organometallic complexes with pyrazine skeletons such as tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq) 3 ]), bis(1-phenylisoquinolinato-N,C 2’) Iridium(III) acetylacetonate (abbreviation: [Ir(piq) 2 (acac)]), bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 Organometallic complexes with pyridine skeletons such as iridium(III), platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: [PtOEP]), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM) 3 (Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA) 3 Examples of rare earth metal complexes include those described above.

[0123] As the organic compound (host material or the like) used in the light-emitting layers (113, 113a, 113b, 113c), one or more substances having a larger energy gap than the energy gap of the light-emitting substance (guest material) may be selected and used.

[0124] Therefore, when the light-emitting substance used in the light-emitting layer (113, 113a, 113b, 113c) is a fluorescent material, it is preferable to use an organic compound (host material) used in combination with the light-emitting substance, which has a high energy level in a singlet excited state and a low energy level in a triplet excited state. As the organic compound (host material) used in combination with the light-emitting substance, in addition to the organic compound of one embodiment of the present invention shown in Embodiment 1, and the hole-transporting material (described above) and the electron-transporting material (described later) shown in this embodiment, a bipolar material or the like can be used. By using the organic compound of one embodiment of the present invention shown in Embodiment 1 in the light-emitting layer (particularly by using it as a host material), initial deterioration of the light-emitting device can be suppressed and reliability can be improved.

[0125] Although some of the examples overlap with the above specific examples, specific examples of organic compounds are shown below from the viewpoint of preferable combinations with light-emitting substances (fluorescent materials, phosphorescent materials).

[0126] When the light-emitting substance is a fluorescent material, examples of an organic compound (host material) that can be used in combination with the light-emitting substance include condensed polycyclic aromatic compounds such as anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives. In addition, it is preferable to use the organic compound according to one embodiment of the present invention described in Embodiment 1.

[0127] Specific examples of organic compounds (host materials) used in combination with fluorescent light-emitting substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10 -phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-di Phenylchrysene, N,N,N',N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2 mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}-anthracene (abbreviation: FLPPA), 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'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,Examples include 9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,12-diphenyltetracene, and 5,12-bis(biphenyl-2-yl)tetracene.

[0128] Furthermore, when the light-emitting substance is a phosphorescent material, an organic compound having a triplet excitation energy larger than that of the light-emitting substance may be selected as an organic compound (host material) used in combination with the light-emitting substance. In particular, the organic compound according to one embodiment of the present invention shown in Embodiment 1 is suitable. Note that when a plurality of organic compounds (e.g., a first host material and a second host material (or assist material)) are used in combination with the light-emitting substance to form an exciplex, it is preferable to mix these organic compounds with the phosphorescent material.

[0129] With such a structure, light emission using ExTET (Exciplex-Triplet Energy Transfer), which is an energy transfer from an exciplex to a light-emitting material, can be efficiently obtained. Note that as a combination of a plurality of organic compounds, those that easily form an exciplex are preferable, and it is particularly preferable to combine a compound that easily receives holes (hole transporting material) with a compound that easily receives electrons (electron transporting material). Note that the organic compound according to one embodiment of the present invention described in Embodiment 1 has a stable triplet excited state, and is therefore suitable as a host material when the light-emitting material is a phosphorescent material. When the above-mentioned exciplex is formed, it is suitable as an electron transporting material. In particular, it is suitable when used in combination with a phosphorescent material that exhibits green light emission due to its triplet excited energy level.

[0130] In addition, examples of organic compounds (host materials, assist materials) that can be used in combination with the light-emitting substance when the light-emitting substance is a phosphorescent material include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, zinc- or aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, and phenanthroline derivatives.

[0131] Among the above, specific examples of the aromatic amine (compound having an aromatic amine skeleton) which is an organic compound having a high hole-transporting property include the same as the specific examples of the hole-transporting material shown above.

[0132] Specific examples of the carbazole derivative, which is an organic compound having a high hole transporting property, include the same as the specific examples of the hole transporting material given above.

[0133] Specific examples of dibenzothiophene derivatives and dibenzofuran derivatives, which are organic compounds with high hole transport properties, include 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 1,3,5-tri(dibenzothiophene-4-yl)-benzene ( abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4-[3-(triphenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mDBTPTp-II), and the like.

[0134] Specific examples of zinc or aluminum metal complexes, which are organic compounds with high electron transport properties, include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq), etc. 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), and other metal complexes having a quinoline skeleton or a benzoquinoline skeleton.

[0135] In addition, metal complexes having oxazole or thiazole ligands, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), can also be used.

[0136] Specific examples of organic compounds with high electron transport properties, such as oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, and phenanthroline derivatives, include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole- 2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazolyl) [4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II).

[0137] Specific examples of heterocyclic compounds having a diazine skeleton, a heterocyclic compound having a triazine skeleton, and a heterocyclic compound having a pyridine skeleton, which are organic compounds with high electron transport properties, include 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and the like. In particular, the organic compound which is one embodiment of the present invention described in Embodiment 1 can also be used.

[0138] In addition, as organic compounds with high electron transport properties, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.

[0139] In addition, when a plurality of organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c), two kinds of compounds (a first compound and a second compound) that form an exciplex may be mixed with an organometallic complex. In this case, various organic compounds can be used in appropriate combination, but in order to efficiently form an exciplex, it is particularly preferable to combine a compound that easily receives holes (a hole transporting material) with a compound that easily receives electrons (an electron transporting material). As specific examples of the hole transporting material and the electron transporting material, the materials shown in this embodiment mode can be used. With this configuration, high efficiency, low voltage, and long life can be simultaneously achieved.

[0140] A TADF material is a material that can upconvert a triplet excited state to a singlet excited state by a small amount of thermal energy (reverse intersystem crossing), and efficiently emits light (fluorescence) from the singlet excited state. Conditions for efficiently obtaining thermally activated delayed fluorescence include an energy difference between the triplet excited level and the singlet excited level of 0 eV or more and 0.2 eV or less, and preferably 0 eV or more and 0.1 eV or less. Delayed fluorescence in TADF materials refers to light emission that has a spectrum similar to that of normal fluorescence, but has a significantly long lifetime. The lifetime is approximately 10 -6 seconds or more, preferably 10 -3 More than seconds.

[0141] Examples of TADF materials include fullerene and its derivatives, acridine derivatives such as proflavine, and eosin. Examples of metal-containing porphyrins include those containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complexes (abbreviated as SnF 2 (Proto IX)), mesoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Meso IX)), hematoporphyrin-tin fluoride complex (abbreviation: SnF 2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF 2 (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF 2 (OEP)), etioporphyrin-tin fluoride complex (abbreviation: SnF 2 (Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl 2 OEP) etc.

[0142] Other examples include 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), Examples of heterocyclic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring include bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), and the like. In addition, a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded to each other is particularly preferable because the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-deficient heteroaromatic ring are both strong, and the energy difference between the singlet excited state and the triplet excited state is small.

[0143] In addition, when a TADF material is used, it can be used in combination with other organic compounds. In particular, it is preferable to use the organic compound which can be combined with the above-mentioned host material, hole transport material, and electron transport material and which is one embodiment of the present invention described in Embodiment 1 as a host material for the TADF material.

[0144] The above materials can be used to form the light-emitting layers (113, 113a, 113b) by combining them with low-molecular-weight materials or polymeric materials. For film formation, known methods (such as vapor deposition, coating, and printing) can be used as appropriate.

[0145] In the light-emitting device shown in Fig. 1, electron transport layers (114, 114a) are formed on the light-emitting layers (113, 113a) of the EL layers (103, 103a). In the case of a light-emitting device having a tandem structure shown in Fig. 1(D), after the EL layer 103a and the charge generation layer 104 are formed, an electron transport layer 114b is also formed on the light-emitting layer 113b of the EL layer 103b.

[0146] <Electron transport layer> The electron transport layers (114, 114a, 114b) are layers that transport electrons injected from the second electrode 102 by the electron injection layers (115, 115a, 115b) to the light-emitting layers (113, 113a, 113b). The electron transport layers (114, 114a, 114b) are layers that contain an electron transport material. The electron transport material used in the electron transport layers (114, 114a, 114b) has an electron mobility of 1×10 at a square root of an electric field strength [V / cm] of 600. -6 cm 2 A substance having an electron mobility of 1000 nm or more is preferable. Note that any substance having a higher electron transporting property than a hole transporting property can be used other than the above. In addition, the organic compound which is one embodiment of the present invention described in Embodiment 1 has a high electron transporting property and can therefore also be used as an electron transporting layer.

[0147] Examples of the electron-transporting material that can be used include metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, and metal complexes having a thiazole skeleton, as well as materials with high electron-transporting properties, such as oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives having a quinoline ligand, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other π-electron-deficient heteroaromatic compounds including nitrogen-containing heteroaromatic compounds.

[0148] A specific example of an electron transport material is tris(8-quinolinolato)aluminum(III) (abbreviation: Alq 3 ), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), Bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), and other metal complexes having a quinoline skeleton or a benzoquinoline skeleton; and metal complexes having an oxazole skeleton or a thiazole skeleton, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and other metal complexes having an oxazole skeleton or a thiazole skeleton.

[0149] In addition to metal complexes, oxadiazole derivatives such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), and 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4'-tert-butylphenyl)-4-phenyl-5-(4''-bi ... triazole derivatives such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), imidazole derivatives such as 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), Conductors (including benzimidazole derivatives), oxazole derivatives such as 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), phenanthroline derivatives such as bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq) -II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), or dibenzoquinoxaline derivatives, pyridine derivatives such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and 4,6-bis[3-(phenanthren-9-yl)phenyl] Pyrimidine derivatives such as pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), and 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), and triazine derivatives such as 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) can be used. In particular, the organic compound which is one embodiment of the present invention shown in Embodiment 1 can also be used.

[0150] In addition, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.

[0151] In addition, the electron transport layer (114, 114a, 114b) may be not only a single layer, but also a laminate structure of two or more layers made of the above-mentioned substances.

[0152] 1D, the electron injection layer 115a is formed on the electron transport layer 114a of the EL layer 103a by vacuum deposition. Then, the EL layer 103a and the charge generation layer 104 are formed, and the electron transport layer 114b of the EL layer 103b is formed, and then the electron injection layer 115b is formed thereon by vacuum deposition.

[0153] <Electron injection layer> The electron injection layer (115, 115a, 115b) is a layer containing a substance with high electron injection properties. The electron injection layer (115, 115a, 115b) contains lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiO x Alkali metals, alkaline earth metals, or compounds thereof, such as erbium fluoride (ErF 3 A rare earth metal compound such as ZnO, ZnS, ZnO ...

[0154] In addition, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer (115, 115a, 115b). Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned electron transport material (metal complex, heteroaromatic compound, etc.) used for the electron transport layer (114, 114a, 114b) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of the electron donor include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and examples of the oxide include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide can also be used. In addition, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0155] 1D, when the light obtained from the light-emitting layer 113b is amplified, the optical distance between the second electrode 102 and the light-emitting layer 113b is preferably less than ¼ 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-transporting layer 114b or the electron-injecting layer 115b.

[0156] <Charge generation layer> In the light-emitting device shown in FIG. 1(D), the charge generation layer 104 has a 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 (cathode) 102. The charge generation layer 104 may be a structure in which an electron acceptor is added to a hole transporting material, or a structure in which an electron donor is added to an electron transporting material. In addition, both of these structures may be laminated. By forming the charge generation layer 104 using the above-mentioned material, it is possible to suppress an increase in driving voltage when EL layers are laminated.

[0157] In the case where the charge generation layer 104 has a structure in which an electron acceptor is added to a hole-transporting material, the material described in this embodiment mode can be used as the hole-transporting material. In addition, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, etc. Also included are oxides of metals belonging to Groups 4 to 8 of the periodic table. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.

[0158] In the case where the charge generation layer 104 has a structure in which an electron donor is added to an electron transporting material, the material shown in this embodiment can be used as the electron transporting material. In addition, as the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or a metal belonging to Groups 2 and 13 of the periodic table, and an oxide or carbonate thereof can be used. Specifically, it is preferable to use lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like. In addition, an organic compound such as tetrathianaphthacene may be used as the electron donor.

[0159] 1E may have the same structure as the above-described EL layers (103, 103a, 103b). Also, the charge generation layers 104a and 104b may have the same structure as the above-described charge generation layer 104.

[0160] <Substrate> The light-emitting device shown in this embodiment mode can be formed on various substrates. The type of substrate is not limited to a specific one. Examples of the substrate include a semiconductor substrate (e.g., a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having stainless steel foil, a tungsten substrate, a substrate having tungsten foil, a flexible substrate, a laminated film, a paper containing a fibrous material, or a base film.

[0161] Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, soda lime glass, etc. Examples of flexible substrates, laminated films, base films, etc. include plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), synthetic resins such as acrylic resins, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic deposition film, and paper.

[0162] In addition, the light-emitting device shown in this embodiment can be manufactured by a vacuum process such as a deposition method, or a solution process such as a spin coating method or an ink-jet method. When a deposition method is used, a physical deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam deposition method, a molecular beam deposition method, or a vacuum deposition method, a chemical deposition method (CVD method), or the like can be used. In particular, the functional layers (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 (screen printing) method, offset (lithographic printing) method, flexo (relief printing) method, gravure method, microcontact method, nanoimprint method, etc.), or the like.

[0163] In addition, the functional layers (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)) constituting the EL layer (103, 103a, 103b) of the light emitting device shown in this embodiment are not limited to the above-mentioned materials, and other materials can be used in combination as long as they can fulfill the functions of each layer. As an example, a polymer compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (a compound in the intermediate range between a low molecular weight and a polymer: molecular weight 400 to 4000), an inorganic compound (quantum dot material, etc.), etc. can be used. As the quantum dot material, colloidal quantum dot materials, alloy type quantum dot materials, core-shell type quantum dot materials, core type quantum dot materials, etc. can be used.

[0164] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments.

[0165] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described. The light-emitting device shown in FIG. 2(A) is an active matrix type light-emitting device in which a transistor (FET) 202 and light-emitting devices (203R, 203G, 203B, 203W) on a first substrate 201 are electrically connected, and the light-emitting devices (203R, 203G, 203B, 203W) have a common EL layer 204 and have a microcavity structure in which the optical distance between the electrodes of each light-emitting device is adjusted according to the light-emitting color of each light-emitting device. In addition, the light-emitting device is a top-emission type light-emitting device in which light emitted from the EL layer 204 is emitted through color filters (206R, 206G, 206B) formed on a second substrate 205.

[0166] 2A, a first electrode 207 is formed to function as a reflective electrode. A second electrode 208 is formed to function as a semi-transmissive and semi-reflective electrode. Note that the electrode materials for forming the first electrode 207 and the second electrode 208 may be appropriately selected from those described in other embodiments.

[0167] 2(A), for example, when light-emitting device 203R is a red light-emitting device, light-emitting device 203G is a green light-emitting device, light-emitting device 203B is a blue light-emitting device, and light-emitting device 203W is a white light-emitting device, as shown in FIG. 2(B), light-emitting device 203R is adjusted so that the optical distance between first electrode 207 and second electrode 208 is 200R, light-emitting device 203G is adjusted so that the optical distance between first electrode 207 and second electrode 208 is 200G, and light-emitting device 203B is adjusted so that the optical distance between first electrode 207 and second electrode 208 is 200B. Note that, as shown in FIG. 2(B), optical adjustment can be performed by stacking conductive layer 210R on first electrode 207 in light-emitting device 203R and stacking conductive layer 210G on first electrode 207 in light-emitting device 203G.

[0168] Color filters (206R, 206G, 206B) are formed on the second substrate 205. The color filters are filters that pass a specific wavelength range of visible light and block a specific wavelength range. Therefore, as shown in FIG. 2(A), by providing a color filter 206R that passes only a red wavelength range at a position overlapping the light emitting device 203R, red light can be emitted from the light emitting device 203R. By providing a color filter 206G that passes only a green wavelength range at a position overlapping the light emitting device 203G, green light can be emitted from the light emitting device 203G. By providing a color filter 206B that passes only a blue wavelength range at a position overlapping the light emitting device 203B, blue light can be emitted from the light emitting device 203B. However, the light emitting device 203W can emit white light without providing a color filter. A black layer (black matrix) 209 may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material.

[0169] FIG. 2(A) shows a light-emitting device having a structure (top emission type) in which light is extracted on the second substrate 205 side, but as shown in FIG. 2(C), a light-emitting device having a structure (bottom emission type) in which light is extracted on the first substrate 201 side on which the FET 202 is formed may be used. In the case of a bottom emission type light-emitting device, the first electrode 207 is formed to function as a semi-transmissive / semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. The first substrate 201 is at least a light-transmitting substrate. The color filters (206R', 206G', 206B') may be provided on the first substrate 201 side of the light-emitting devices (203R, 203G, 203B) as shown in FIG. 2(C).

[0170] 2A shows the cases where the light-emitting device is a red light-emitting device, a green light-emitting device, a blue light-emitting device, and a white light-emitting device, but the light-emitting device according to one embodiment of the present invention is not limited to these configurations, and may have a yellow light-emitting device or an orange light-emitting device. Note that materials used in the EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer, etc.) for manufacturing these light-emitting devices may be appropriately selected by referring to the descriptions of other embodiments. Note that in this case, it is also necessary to appropriately select a color filter according to the light-emitting color of the light-emitting device.

[0171] With the above-mentioned configuration, a light emitting device including light emitting devices that emit light of a plurality of colors can be obtained.

[0172] Note that the structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments.

[0173] (Embodiment 4) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0174] By applying the element configuration of the light-emitting device which is one embodiment of the present invention, an active matrix light-emitting device or a passive matrix light-emitting device can be manufactured. Note that an active matrix light-emitting device has a configuration in which a light-emitting device and a transistor (FET) are combined. Therefore, both a passive matrix light-emitting device and an active matrix light-emitting device are included in one embodiment of the present invention. Note that the light-emitting device described in the other embodiments can be applied to the light-emitting device shown in this embodiment.

[0175] In this embodiment mode, an active matrix light emitting device will be described with reference to FIG.

[0176] 3(A) is a top view showing the light-emitting device, and FIG. 3(B) is a cross-sectional view taken along dashed line A-A' in FIG. 3(A). The active matrix light-emitting device has a pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate line driver circuit) (304a, 304b) provided on a first substrate 301. The pixel portion 302 and the driver circuit portion (303, 304a, 304b) are sealed between the first substrate 301 and a second substrate 306 by a sealant 305.

[0177] Moreover, on the first substrate 301, lead wiring 307 is provided. The lead wiring 307 is electrically connected to an FPC 308 which is an external input terminal. The FPC 308 transmits signals (e.g., video signals, clock signals, start signals, reset signals, etc.) and potentials from the outside to the drive circuit units (303, 304a, 304b). A printed wiring board (PWB) may be attached to the FPC 308. The state in which the FPC and PWB are attached is included in the light-emitting device.

[0178] Next, a cross-sectional structure is shown in FIG.

[0179] The pixel section 302 is formed by a plurality of pixels each having a FET (switching FET) 311, a FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312. The number of FETs each pixel has is not particularly limited, and may be appropriately provided as necessary.

[0180] The FETs 309, 310, 311, and 312 are not particularly limited, and may be, for example, staggered or inverted staggered transistors, or may have a top-gate or bottom-gate transistor structure.

[0181] Note that the crystallinity of a semiconductor that can be used for these FETs 309, 310, 311, and 312 is not particularly limited, and any of an amorphous semiconductor and a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in a part) may be used. Note that the use of a semiconductor having crystallinity is preferable because it can suppress deterioration of transistor characteristics.

[0182] Examples of the semiconductor that can be used include Group 14 elements, compound semiconductors, oxide semiconductors, and organic semiconductors. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, and an oxide semiconductor containing indium can be used.

[0183] The driver circuit unit 303 has an FET 309 and an FET 310. The driver circuit unit 303 may be formed of a circuit including transistors of the same polarity (either N-type or P-type), or may be formed of a CMOS circuit including N-type transistors and P-type transistors. Also, the driver circuit unit 303 may be configured to have an external driver circuit.

[0184] An end of the first electrode 313 is covered with an insulator 314. For the insulator 314, an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin), or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride can be used. The upper end or lower end of the insulator 314 preferably has a surface with a curvature. This can improve the coverage of the film formed on the upper layer of the insulator 314.

[0185] An EL layer 315 and a second electrode 316 are stacked over 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, and the like.

[0186] Note that the structures and materials described in the other embodiments can be applied to the structure of the light-emitting device 317 shown in this embodiment. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.

[0187] In addition, although only one light-emitting device 317 is illustrated in the cross-sectional view shown in FIG. 3B, a plurality of light-emitting devices are arranged in a matrix in the pixel portion 302. In the pixel portion 302, light-emitting devices capable of emitting three types of light (R, G, B) can be selectively formed, respectively, to form a light-emitting device capable of full-color display. In addition to the light-emitting devices capable of emitting three types of light (R, G, B), light-emitting devices capable of emitting, for example, white (W), yellow (Y), magenta (M), cyan (C), etc., may be formed. For example, by adding the above-mentioned light-emitting devices capable of emitting several types of light to the light-emitting device capable of emitting three types of light (R, G, B), effects such as improved color purity and reduced power consumption can be obtained. In addition, a light-emitting device capable of full-color display may be formed by combining with a color filter. Note that the types of color filters that can be used include red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), etc.

[0188] The FETs (309, 310, 311, 312) and the light emitting device 317 on the first substrate 301 have a structure in which they are provided in a region 318 surrounded by the first substrate 301, the second substrate 306, and the sealant 305 by bonding the second substrate 306 and the first substrate 301 with the sealant 305. The region 318 may be filled with an inert gas (nitrogen, argon, etc.) or an organic substance (including the sealant 305).

[0189] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material that is as impermeable to moisture and oxygen as possible for the sealing material 305. The second substrate 306 can be made of the same material as the first substrate 301. Therefore, it is possible to use various substrates described in other embodiments as appropriate. As the substrate, in addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic resin, or the like can be used. When glass frit is used as the sealing material, it is preferable that the first substrate 301 and the second substrate 306 are glass substrates from the viewpoint of adhesion.

[0190] In this manner, an active matrix light emitting device can be obtained.

[0191] In addition, when forming an active matrix type light emitting device on a flexible substrate, the FET and the light emitting device may be formed directly on the flexible substrate, or the FET and the light emitting device may be formed on another substrate having a peeling layer, and then the FET and the light emitting device may be peeled off at the peeling layer by applying heat, force, laser irradiation, or the like, and then transferred to the flexible substrate to fabricate the device. As the peeling layer, for example, a laminate of inorganic films of a tungsten film and a silicon oxide film, or an organic resin film such as polyimide, etc. may be used. In addition to substrates on which transistors can be formed, examples of the flexible substrate include paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, cloth substrates (including natural fibers (silk, cotton, hemp), synthetic fibers (nylon, polyurethane, polyester) or regenerated fibers (acetate, cupra, rayon, regenerated polyester), etc.), leather substrates, and rubber substrates. By using these substrates, it is possible to achieve excellent durability and heat resistance, and to achieve lighter weight and thinner thickness.

[0192] Note that the structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiment modes.

[0193] (Embodiment 5) In this embodiment, examples of various electronic devices and automobiles completed by applying a light-emitting device according to one embodiment of the present invention and a light-emitting device having a light-emitting device according to one embodiment of the present invention will be described. Note that the light-emitting device can be applied mainly to a display portion in the electronic devices described in this embodiment.

[0194] The electronic devices shown in Figures 4(A) to 4(E) may have a housing 7000, a display unit 7001, a speaker 7003, an LED lamp 7004, operation keys 7005 (including a power switch or an operation switch), a connection terminal 7006, a sensor 7007 (including a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), a microphone 7008, etc.

[0195] FIG. 4A shows a mobile computer, which may have, in addition to the above, a switch 7009, an infrared port 7010, and the like.

[0196] FIG. 4B shows a portable image reproducing device (for example, a DVD reproducing device) equipped with a recording medium, which can further include a second display portion 7002, a recording medium reading portion 7011, and the like in addition to the above-mentioned components.

[0197] FIG. 4C shows a digital camera with a television receiving function, which can have an antenna 7014, a shutter button 7015, an image receiving unit 7016, and the like in addition to the above components.

[0198] 4D shows a portable information terminal. The portable information terminal has a function of displaying information on three or more surfaces of a display unit 7001. Here, an example is shown in which information 7052, information 7053, and information 7054 are displayed on different surfaces. For example, a user can check information 7053 displayed in a position that can be observed from above the portable information terminal while the portable information terminal is stored in a breast pocket of clothes. The user can check the display without taking the portable information terminal out of the pocket and determine, for example, whether to answer a call.

[0199] FIG. 4E shows a portable information terminal (including a smartphone), which may have a display unit 7001, operation keys 7005, and the like in a housing 7000. The portable information terminal may also be provided with a speaker 9003, a connection terminal 7006, a sensor 9007, and the like. The portable information terminal may also display text and image information on a plurality of surfaces. Here, an example is shown in which three icons 7050 are displayed. Information 7051, indicated by a dashed rectangle, may also be displayed on another surface of the display unit 7001. Examples of the information 7051 include notifications of incoming e-mail, SNS, and phone calls, titles of e-mail and SNS, sender name, date and time, time, remaining battery level, and antenna reception strength. Alternatively, the icon 7050 may be displayed at the position where the information 7051 is displayed.

[0200] FIG. 4F shows a large television set (also referred to as a television or a television receiver), which may include a housing 7000, a display portion 7001, and the like. Here, the housing 7000 is supported by a stand 7018. The television set can be operated using a separate remote control unit 7111 or the like. Note that the display portion 7001 may be provided with a touch sensor, and the display portion 7001 may be operated by touching it with a finger or the like. The remote control unit 7111 may have a display portion that displays information output from the remote control unit 7111. Using operation keys or a touch panel provided in the remote control unit 7111, the channel and volume can be operated, and an image displayed on the display portion 7001 can be operated.

[0201] The electronic devices shown in Fig. 4(A) to Fig. 4(F) can have various functions. For example, they can have a function of displaying various information (still images, videos, text images, etc.) on the display unit, a touch panel function, a function of displaying a calendar, date or time, etc., a function of controlling processing by various software (programs), a wireless communication function, a function of connecting to various computer networks using the wireless communication function, a function of transmitting or receiving various data using the wireless communication function, a function of reading out a program or data recorded on a recording medium and displaying it on the display unit, etc. Furthermore, electronic devices having multiple display units can have a function of mainly displaying image information on one display unit and mainly displaying text information on another display unit, or a function of displaying a stereoscopic image by displaying an image taking into account parallax on multiple display units, etc. Furthermore, electronic devices having an image receiving unit can have a function of taking still images, a function of taking videos, a function of automatically or manually correcting the taken images, a function of saving the taken images on a recording medium (external or built-in to the camera), a function of displaying the taken images on the display unit, etc. Note that the functions that the electronic devices illustrated in FIGS. 4A to 4F can have are not limited to those shown in FIG. 4A to FIG. 4F, and the electronic devices can have various functions.

[0202] FIG. 4G shows a wristwatch-type portable information terminal, which can be used as, for example, a smart watch. This wristwatch-type portable information terminal includes a housing 7000, a display portion 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a microphone 7026, a sensor 7029, a speaker 7030, and the like. The display surface of the display portion 7001 is curved, and display can be performed along the curved display surface. This portable information terminal can also perform hands-free conversation by mutual communication with, for example, a headset capable of wireless communication. Note that the connection terminal 7024 can also perform data transmission to and from another information terminal and charging. Charging can also be performed by wireless power supply.

[0203] A display unit 7001 mounted on a housing 7000 that also serves as a bezel portion has a non-rectangular display area. The display unit 7001 can display an icon 7027 indicating the time, other icons 7028, and the like. The display unit 7001 may also be a touch panel (input / output device) equipped with a touch sensor (input device).

[0204] The smart watch shown in Fig. 4(G) can have various functions. For example, it can have a function of displaying various information (still images, videos, text images, etc.) on the display unit, a touch panel function, a function of displaying a calendar, date or time, etc., a function of controlling processing by various software (programs), a wireless communication function, a function of connecting to various computer networks using the wireless communication function, a function of transmitting or receiving various data using the wireless communication function, a function of reading out a program or data recorded on a recording medium and displaying it on the display unit, etc.

[0205] The housing 7000 may also have a speaker, sensors (including functions to measure force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), microphone, etc. inside the housing 7000.

[0206] Note that the light-emitting device which is one embodiment of the present invention and a display device including the light-emitting device which is one embodiment of the present invention can be used in each display portion of the electronic devices described in this embodiment, and the electronic devices can have a long lifetime.

[0207] An example of an electronic device to which a light-emitting device is applied is a foldable portable information terminal as shown in Figures 5(A) to 5(C). Figure 5(A) shows the portable information terminal 9310 in an unfolded state. Figure 5(B) shows the portable information terminal 9310 in a state in the process of changing from an unfolded state to the other state, either unfolded or folded. Figure 5(C) shows the portable information terminal 9310 in a folded state. The portable information terminal 9310 has excellent portability in a folded state, and has excellent viewability of a display due to a seamless wide display area in an unfolded state.

[0208] The display portion 9311 is supported by three housings 9315 connected by hinges 9313. Note that the display portion 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). The display portion 9311 can be reversibly transformed from an unfolded state of the portable information terminal 9310 to a folded state by bending the two housings 9315 via the hinges 9313. Note that the light-emitting device of one embodiment of the present invention can be used for the display portion 9311. In addition, an electronic device with a long life can be realized. A display region 9312 in the display portion 9311 is a display region located on a side surface of the portable information terminal 9310 in the folded state. In the display region 9312, information icons, frequently used apps, shortcuts to programs, and the like can be displayed, and thus information can be checked and apps can be started smoothly.

[0209] 6(A) and 6(B) show automobiles to which the light emitting device is applied. That is, the light emitting device can be provided integrally with the automobile. Specifically, the light emitting device can be applied to an exterior light 5101 (including the rear of the vehicle), a tire wheel 5102, a part or the whole of a door 5103, and the like, of the automobile shown in FIG. 6(A). The light emitting device can also be applied to a display unit 5104, a steering wheel 5105, a shift lever 5106, a seat 5107, an inner rear view mirror 5108, and the like, inside the automobile shown in FIG. 6(B). In addition, the light emitting device may be applied to a part of a glass window.

[0210] In the above manner, an electronic device or an automobile to which the light-emitting device or the display device according to one embodiment of the present invention is applied can be obtained. In that case, an electronic device with a long life can be realized. Note that the electronic devices and automobiles to which the present invention can be applied are not limited to those described in this embodiment, and can be applied in any field.

[0211] Note that the structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiment modes.

[0212] (Embodiment 6) In this embodiment, a structure of a lighting device manufactured using a light-emitting device which is one embodiment of the present invention or a light-emitting device which is a part of the light-emitting device will be described with reference to FIGS.

[0213] Figures 7(A) and (B) show examples of cross-sectional views of lighting devices. Note that Figure 7(A) shows a bottom emission type lighting device that extracts light on the substrate side, and Figure 7(B) shows a top emission type lighting device that extracts light on the sealing substrate side.

[0214] 7A includes a light-emitting device 4002 over a substrate 4001. A substrate 4003 having projections and recesses is also included on the outer side of the substrate 4001. The light-emitting device 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.

[0215] The first electrode 4004 is electrically connected to an electrode 4007, and the second electrode 4006 is electrically connected to an electrode 4008. In addition, an auxiliary wiring 4009 electrically connected to the first electrode 4004 may be provided. Note that an insulating layer 4010 is formed over the auxiliary wiring 4009.

[0216] The substrate 4001 and the sealing substrate 4011 are bonded with a sealant 4012. A desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting device 4002. Since the substrate 4003 has projections and recesses as shown in FIG. 7A, the efficiency of extracting light generated in the light-emitting device 4002 can be improved.

[0217] 7B includes a light-emitting device 4202 over a substrate 4201. The light-emitting device 4202 includes a first electrode 4204, an EL layer 4205, and a second electrode 4206.

[0218] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. In addition, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. In addition, an insulating layer 4210 may be provided under the auxiliary wiring 4209.

[0219] The substrate 4201 and a sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. A barrier film 4213 and a planarizing film 4214 may be provided between the sealing substrate 4211 and the light-emitting device 4202. Since the sealing substrate 4211 has projections and recesses as shown in FIG. 7B, the efficiency of extracting light generated in the light-emitting device 4202 can be improved.

[0220] An example of the application of these lighting devices is a ceiling light for indoor lighting. Ceiling lights include a direct ceiling type and a ceiling recessed type. Such lighting devices are constructed by combining a light-emitting device with a housing and a cover.

[0221] In addition, it can be applied to footlights that can irradiate light onto the floor surface and increase the safety of the feet. Footlights are effective for use in bedrooms, stairs, and corridors, for example. In such cases, the size and shape can be changed appropriately according to the size and structure of the room. It is also possible to make a stationary lighting device that is configured by combining a light-emitting device with a support base.

[0222] It can also be used as a sheet-type lighting device (sheet lighting). Sheet lighting is attached to a wall surface, so it does not take up much space and can be used for a wide range of purposes. It can also be easily made larger. It can also be used on curved walls and housings.

[0223] In addition to the above, the light-emitting device according to one embodiment of the present invention or a light-emitting device that is a part of the light-emitting device can be used as a lighting device having a function as the furniture in a room.

[0224] As described above, various lighting devices using the light-emitting device can be obtained. Note that these lighting devices are included in one embodiment of the present invention.

[0225] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiment modes. EXAMPLES

[0226] <Synthesis Example 1> Example 1 This example describes a synthesis method for 3-[3-(dibenzothiophen-4-yl)phenyl]-7-phenyl[1]benzofuro[3,2-c]pyridazine (abbreviation: 7Ph-3mDBtPBfpd), an organic compound according to one embodiment of the present invention, represented by structural formula (100) in Embodiment 1. The structure of 7Ph-3mDBtPBfpd is shown below.

[0227] [ka]

[0228] <Step 1; Synthesis of ethyl 2-(6-chloro-3-oxo-1-benzofuran-2-yl)-2-hydroxyacetate> First, 24 mL of ethyl glyoxylate (polymer type) (47% toluene solution) was added to a three-neck flask, the flask was replaced with nitrogen, and 230 mL of toluene was added. In an ice bath, 0.54 g (4.7 mmol) of trifluoroacetic acid was added to this mixture and stirred at 0°C for 30 minutes. 30 g (178 mmol) of 6-chlorobenzofuran-3-one was added thereto, and the mixture was heated to 50°C and stirred for 39 hours. After a predetermined time had passed, the precipitated solid was filtered by suction, and the solid was washed with water, ethanol, and toluene to obtain 7.2 g of the target white solid. Water was added to the filtrate obtained here, and the aqueous layer and the organic layer were separated.

[0229] The organic layer was washed with saturated saline, dried by adding anhydrous magnesium sulfate, and then naturally filtered. The obtained filtrate was concentrated, and the obtained solid was washed with toluene to obtain 4.0 g of the target white solid. The obtained filtrate was purified by silica gel column chromatography. Toluene was used as the developing solvent at first, and the amount of ethyl acetate added was increased so that the final ratio of toluene:ethyl acetate was 2:1, gradually increasing the polarity. The obtained fraction was concentrated, and the obtained solid was washed with toluene to obtain 5.4 g of the target white solid (total 17 g, yield 52%). The synthesis scheme of step 1 is shown in (a-1).

[0230] [ka]

[0231] <Step 2: Synthesis of 7-chloro[1]benzofuro[3,2-c]pyridazin-3-one> Next, 22 g (81 mmol) of ethyl 2-(6-chloro-3-oxo-1-benzofuran-2-yl)-2-hydroxyacetate obtained in step 1 above and 340 mL of ethanol were added to a three-neck flask, and 12 g (240 mmol) of hydrazine monohydrate was added thereto, and the mixture was stirred at room temperature overnight, and then heated to reflux for 40 hours. The resulting reaction mixture was poured into water and stirred at room temperature. The mixture was suction filtered, and the solid was washed with ethanol to obtain 5.5 g of the target pale orange solid in a yield of 30%. The synthesis scheme of step 2 is shown in (a-2).

[0232] [ka]

[0233] <Step 3: Synthesis of 3,7-dichloro[1]benzofuro[3,2-c]pyridazine> Next, 5.5 g (25 mmol) of 7-chloro[1]benzofuro[3,2-c]pyridazin-3-one obtained in step 2 above and 80 mL of toluene were added to a three-neck flask, to which 19 g (125 mmol) of phosphoryl chloride and 0.1 mL of dimethylformamide were added and heated to reflux for 12 hours.

[0234] The resulting reaction mixture was neutralized by gradually adding it to an aqueous solution of sodium hydroxide in an ice bath. The aqueous and organic layers were separated, and the aqueous layer was extracted with toluene. The resulting organic layer was washed with saturated saline and dried by adding anhydrous magnesium sulfate. The resulting mixture was gravity filtered, and the filtrate was concentrated to obtain a solid. This solid was dissolved in heated toluene and suction filtered through a filter material layered in the order of Celite, alumina, and Celite. The resulting filtrate was concentrated, and the solid was washed with ethanol to obtain 3.7 g of the desired white solid in a yield of 63%. The synthesis scheme of step 3 is shown in (a-3).

[0235] [ka]

[0236] <Step 4; Synthesis of 7-chloro-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine> Next, 3.1g (13mmol) of 3,7-dichloro[1]benzofuro[3,2-c]pyridazine obtained in step 3 above, 4.4g (14mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 9.1g (43mmol) of tripotassium phosphate, 0.22g (0.52mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-phos), and 130mL of xylene were placed in a reaction vessel, and the inside of the reaction vessel was degassed and replaced with nitrogen. 63mg (0.28mmol) of palladium (II) acetate was added to this mixture and heated and stirred at 120°C for 12 hours. 0.22g (0.52mmol) of S-phos and 63mg (0.28mmol) of palladium (II) acetate were added to this mixture and heated and stirred at 130°C for 8.5 hours. To this, 0.95g (3.1mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 2.0g (9.4mmol) of tripotassium phosphate, 0.21g (0.52mmol) of S-phos, and 59mg (0.27mmol) of palladium (II) acetate were added and heated and stirred for 14 hours at 130°C. To this, 0.95g (3.1mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 2.0g (9.4mmol) of tripotassium phosphate, 0.21g (0.52mmol) of S-phos, and 54mg (0.24mmol) of palladium (II) acetate were added and heated and stirred for 7 hours at 130°C. To this, 0.95 g (3.1 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 1.9 g (9.0 mmol) of tripotassium phosphate, 0.23 g (0.56 mmol) of S-phos, and 71 mg (0.32 mmol) of palladium (II) acetate were added and heated and stirred at 130 ° C for 4 hours. The resulting reaction mixture was suction filtered, and the solid was washed with water and ethanol. This solid was dissolved in heated toluene, 90 g of alumina was added, and the mixture was heated and stirred at 90 ° C. This mixture was suction filtered through Celite, and washed with heated toluene. The obtained filtrate was concentrated to obtain a brown solid. This solid was recrystallized in toluene to obtain 1.6 g of the target white solid in a yield of 27%. The synthesis scheme of step 4 is shown in (a-4).

[0237] [ka]

[0238] <Step 5: Synthesis of 3-[3-(dibenzothiophen-4-yl)phenyl]-7-phenyl[1]benzofuro[3,2-c]pyridazine (abbreviation: 7Ph-3mDBtPBfpd)> Next, 0.53 g (1.1 mmol) of 7-chloro-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine obtained in step 4 above, 0.18 g (1.4 mmol) of phenylboronic acid, 0.62 g (4.1 mmol) of cesium fluoride, and 30 mL of xylene were placed in a reaction vessel, and the inside of the vessel was replaced with nitrogen. After heating the mixture to 60°C while stirring, 27 mg (0.029 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 25 mg (0.069 mmol) of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added, and the temperature was raised to 110°C and the mixture was heated and stirred for 23 hours.

[0239] After a predetermined time had elapsed, 25 mg (0.029 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 26 mg (0.069 mmol) of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added to the mixture, and the mixture was heated and stirred at 120°C for 39 hours.

[0240] After a predetermined time had elapsed, 0.086 g (0.70 mmol) of phenylboronic acid, 0.3 g (2.0 mmol) of cesium fluoride, 12 mg (0.013 mmol) of tris(dibenzylideneacetone)dipalladium(0), and 13 mg (0.036 mmol) of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added to the mixture and heated with stirring for 13 hours.

[0241] Water was added to the resulting mixture, which was then suction filtered and the solid was washed with ethanol. This solid was dissolved in heated toluene and suction filtered through a filter material layered in the order of Celite, alumina, and Celite. The filtrate was concentrated to obtain a solid. This solid was recrystallized in toluene to obtain 0.23 g of the desired white solid in a yield of 40%. The synthesis scheme for step 5 is shown in the following formula (a-5).

[0242] [ka]

[0243] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 5 above ( 1 The results of the analysis by H-NMR are shown below. 1 The H-NMR chart is shown in Fig. 8. From the results, it was found that in this example, the organic compound 7Ph-3mDBtPBfpd, which is one embodiment of the present invention and is represented by the above structural formula (100), was obtained.

[0244] 1 H-NMR.δ(CDCl 3 ):7.44-7.55(m,5H),7.60-7.64(m,2H),7.71-7.76(m,3H),7.80(dd,1H),7.86-7.88(m,2H ),7.92(ddd,1H),8.05(s,1H),8.21-8.24(m,2H),8.32(d,1H),8.51(d,1H),8.57(dd,1H).

[0245] <Physical properties of 7Ph-3mDBtPBfpd> Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution of 7Ph-3mDBtPBfpd were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics Corporation). The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 9. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity.

[0246] From the results in FIG. 9, in the toluene solution of 7Ph-3mDBtPBfpd, absorption peaks were observed near 333 nm and 281 nm, and an emission wavelength peak was observed near 449 nm.

[0247] Next, the phosphorescence spectrum of the toluene solution of 7Ph-3mDBtPBfpd was measured. To measure the phosphorescence spectrum, an absolute PL quantum yield measurement device (C11347-01, manufactured by Hamamatsu Photonics Co., Ltd.) was used. In a glove box (LABstarM13 (1250 / 780, manufactured by Bright Co., Ltd.), the deoxygenated toluene solution was placed in a quartz cell under a nitrogen atmosphere, sealed, and measured at liquid nitrogen temperature. The measurement results of the obtained phosphorescence spectrum are shown in Figure 10. The horizontal axis represents the wavelength, and the vertical axis represents the emission intensity.

[0248] From the results in FIG. 10, a phosphorescence spectrum was observed at 479 nm from a toluene solution of 7Ph-3mDBtPBfpd at liquid nitrogen temperature.

[0249] The organic compound 7Ph-3mDBtPBfpd according to one embodiment of the present invention has a high T1 level and can be said to be a host material suitable for a phosphorescent material (guest material) that emits light in the green range. The organic compound 7Ph-3mDBtPBfpd according to one embodiment of the present invention can also be used as a host material or light-emitting material for phosphorescent light-emitting materials in the visible range. EXAMPLES

[0250] <Synthesis Example 2> Example 1 This example describes a synthesis method for 7-(1,1'-biphenyl-3-yl)-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine (abbreviation: 7mBP-3mDBtPBfpd), an organic compound according to one embodiment of the present invention represented by structural formula (101) in Embodiment 1. The structure of 7mBP-3mDBtPBfpd is shown below.

[0251] [ka]

[0252] <Step 1; Synthesis of 7mBP-3mDBtPBfpd> 1.6 g (3.5 mmol) of 7-chloro-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine obtained in Step 4 of Example 1 (Synthesis Example 1) above, 0.71 g (3.5 mmol) of 3-biphenylboronic acid, 2.2 g (11 mmol) of tripotassium phosphate, 35 mL of diglyme, and 0.79 g (11 mmol) of tert-butanol were placed in a reaction vessel, and the inside of the vessel was degassed and replaced with nitrogen.

[0253] The mixture was heated to 60°C, and 16 mg (0.070 mmol) of palladium (II) acetate and 50 mg (0.14 mmol) of di(1-adamantyl)-n-butylphosphine (cataCXiumA) were added and stirred at 90°C for 6.5 hours. 8 mg (0.035 mmol) of palladium (II) acetate and 25 mg (0.070 mmol) of cataCXiumA were further added and stirred at 90°C for 8 hours. Water was added to the resulting reaction mixture, and the solid was filtered by suction and washed with ethanol. The solid was dissolved in heated toluene and filtered by suction through a filter material layered with Celite-alumina-Celite.

[0254] The obtained filtrate was concentrated to obtain an oily product. This oily product was purified by silica gel column chromatography. Toluene was used as the developing solvent, followed by a mixed solvent of toluene:ethyl acetate = 9:1. Ethanol was added to the oily product obtained by concentrating the obtained fraction, and the solid was precipitated by irradiating with ultrasound. This solid was filtered by suction to obtain 1.45 g of the target white solid with a yield of 71%. The synthesis scheme of step 1 is shown in the following formula (b-1).

[0255] [ka]

[0256] The obtained white solid (1.4 g) was purified by train sublimation. The conditions for the sublimation purification were a pressure of 2.13 Pa and a heating temperature of 325°C. After the sublimation purification, the recovered white solid (0.72 g) was again purified by sublimation. The conditions for the sublimation purification were a pressure of 2.45 Pa and a heating temperature of 310°C. After the sublimation purification, the target product 7-(1,1'-biphenyl-3-yl)-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine (abbreviation: 7mBP-3mDBtPBfpd) was obtained in a yield of 0.57 g (white solid, recovery rate 79%).

[0257] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 The results of the analysis by H-NMR are shown below. 1 The H-NMR chart is shown in Fig. 11. From the results, it was found that in this example, the organic compound 7mBP-3mDBtPBfpd, which is one embodiment of the present invention and is represented by the above structural formula (101), was obtained.

[0258] 1 H-NMR.δ(CD 2 Cl 2 ):7.39-7.42(m,1H),7.49-7.54(m,4H),7.60-7.79(m,8H),7.89-7.91(m,2H),7.93(ddd,1H ),7.97-7.98(m,2H),8.10(s,1H),8.25-8.27(m,2H),8.31(d,1H),8.52(d,1H),8.60(t,1H).

[0259] <<Physical properties of 7mBP-3mDBtPBfpd>> Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of the toluene solution of 7mBP-3mDBtPBfpd were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). The emission spectrum was measured using a fluorometer (FP8600, manufactured by JASCO Corporation). The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Figure 12. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity.

[0260] From the results in FIG. 12, in the toluene solution of 7mBP-3mDBtPBfpd, absorption peaks were observed near 333 nm and 281 nm, and an emission wavelength peak was observed near 368 nm.

[0261] The organic compound 7mBP-3mDBtPBfpd according to one embodiment of the present invention has a high T1 level and can be said to be a host material suitable for a phosphorescent material (guest material) that emits light in the green range. The organic compound 7mBP-3mDBtPBfpd according to one embodiment of the present invention can also be used as a host material or light-emitting material for phosphorescent light-emitting materials in the visible range. [Explanation of symbols]

[0262] 101 First electrode 102 Second electrode 103 EL layer 103a, 103b EL layer 104 Charge generating layer 111, 111a, 111b Hole injection layer 112, 112a, 112b hole transport layer 113, 113a, 113b Light-emitting 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 Devices 204 EL layer 205 Second Board 206R, 206G, 206B Color Filters 206R', 206G', 206B' Color Filters 207 First Electrode 208 Second Electrode 209 Black layer (black matrix) 210R, 210G conductive layer 301 First Substrate 302 Pixel section 303 Driver circuit section (source line driver circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Second Board 307 Wiring 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulation 315 EL layer 316 Second Electrode 317 Light Emitting Devices 318 areas 900 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting Equipment 4001 Substrate 4002 Light-emitting devices 4003 Substrate 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4200 Lighting Equipment 4201 Substrate 4202 Light-emitting devices 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rear view mirror 7000 Chassis 7001 Display section 7002 2nd display section 7003 Speaker 7004 LED Lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7022, 7023 Operation buttons 7024 Connection terminal 7025 Band 7026 Microphone 7029 Sensor 7030 Speaker 7052, 7053, 7054 Information 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 Case

Claims

1. An organic compound represented by general formula (G1) (excluding the compound represented by formula (2-26)). 【Chemistry 1】 In formula (G1), Q represents oxygen or sulfur. A represents a group having a total of 12 to 100 carbon atoms, and has one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. R １ ~R ５ each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 【Chemistry 2】

2. An organic compound represented by general formula (G2): 【Chemistry 3】 In formula (G2), Q represents oxygen or sulfur, α represents a phenylene group which may have a substituent, and n represents an integer of 0 to 4. ｕｎｉ R has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure. １ ~R ５ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

3. An organic compound represented by general formula (G3): 【Chemistry 4】 In formula (G3), Q represents oxygen or sulfur. n represents an integer of 0 to 4. ｕｎｉ R has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure. １ ~R ５ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

4. In claim 2 or 3, The Ht uni is an organic compound represented by any one of the following general formulas (Ht-1) to (Ht-26). 【Chemistry 5】 【Chemistry 6】 (In formulae (Ht-1) to (Ht-26), Q represents oxygen or sulfur. R 2 to R 71 each represent 1 to 4 substituents, and each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.)

5. An organic compound represented by structural formula (100) or (101). 【Chemistry 7】

6. A light-emitting device comprising an organic compound according to any one of claims 1 to 5.

Images