compound

Abstract

To provide novel heterocyclic compounds, and in particular, to provide novel heterocyclic compounds that can improve device characteristics of light-emitting devices.SOLUTION: There is provided a heterocyclic compound represented by the general formula (G1), in which a substituted or unsubstituted dibenzo[f,h]quinoxalinyl group and a substituted or unsubstituted benzobisbenzofuranyl group are bonded to each other via a substituted or unsubstituted arylene group. (In the general formula, DBq represents a substituted or unsubstituted dibenzo [f,h] quinoxalinyl group, Ar1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, n represents 0 or 1, Ar2 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and A represents a substituted or unsubstituted benzobisbenzofuranyl group. When the arylene group represented by Ar1 and Ar2 has substituents, the substituents may be bonded to each other to form a ring.).SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention relates to an article, a method, or a manufacturing method. , machine, manufacture, or composition of matter In particular, one embodiment of the present invention is a semiconductor device, a light-emitting device, a display device, a lighting device, a light-emitting element, Another aspect of the present invention relates to heterocyclic compounds and novel compounds thereof. The present invention also relates to a light-emitting element, a light-emitting device, an electronic device, and a method for producing the heterocyclic compound. However, one embodiment of the present invention is not limited to the above technical field. [Background technology]

[0002] It uses organic compounds as light emitters, which have characteristics such as thinness, light weight, high-speed response, and low DC voltage operation. The light-emitting element is expected to be applied to next-generation flat panel displays. A display device in which light-emitting elements are arranged in a matrix has a longer viewing angle than a conventional liquid crystal display device. It is believed that its advantages lie in its wide angle and excellent visibility.

[0003] The light-emitting mechanism of a light-emitting element is to sandwich an EL layer containing a light-emitting body between a pair of electrodes and apply a voltage. As a result, electrons injected from the cathode and holes injected from the anode are regenerated at the light-emitting centers of the EL layer. They combine to form molecular excitons, which release energy as they relax to the ground state. It is said that the excited state is singlet excited and triplet excited, and the emission is It is believed that either excited state is possible.

[0004] In such light-emitting devices, the EL layer is mainly made of an organic compound, and Since this has a significant impact on improving the device characteristics, various new organic compounds are being developed. For example, see Patent Document 1. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-189001 Summary of the Invention [Problem to be solved by the invention]

[0006] The compound having the dibenzo[f,h]quinoxaline ring reported in the above-mentioned Patent Document 1 The compound has a problem in that it is prone to crystallization due to its planar structure. Light-emitting devices using compounds with a bulky structure tend to have a short lifespan. Therefore, when other skeletons are directly bonded to the dibenzo[f,h]quinoxaline ring, the conjugated system becomes wider. This may cause a decrease in triplet excitation energy. If the compound is lowered, the luminous efficiency will decrease, and the device characteristics of the light-emitting device using such a compound will also decrease. It ends up happening.

[0007] In view of the above, one embodiment of the present invention provides a novel heterocyclic compound. In addition, in one aspect of the present invention, there is provided a novel heterocyclic compound capable of improving the properties. In addition, a novel heterocyclic compound having good luminous efficiency and heat resistance is provided. The present invention provides a novel heterocyclic compound that can be used in a light-emitting element. In this embodiment, a novel heterocyclic compound is provided that can be used in the EL layer of a light-emitting device. Light-emitting elements with high heat resistance, high luminous efficiency and low power consumption, and long lifespan are being developed. In addition, one embodiment of the present invention provides a novel light-emitting element. A novel light-emitting device, a novel electronic device, or a novel lighting device is provided. The description of the subject matter does not necessarily preclude the existence of other problems. It is not necessary to solve all of these problems. Problems other than these may be solved by the specification, drawings, etc. The above will be clear from the description, drawings, claims, etc. It is possible to extract other issues from the description. [Means for solving the problem]

[0008] One aspect of the present invention is a compound comprising a substituted or unsubstituted dibenzo[f,h]quinoxalinyl group and a substituted or unsubstituted dibenzo[f,h]quinoxalinyl group. or an unsubstituted benzobisbenzofuranyl group and a substituted or unsubstituted arylene group It is a heterocyclic compound characterized in that it is bonded via

[0009] One embodiment of the present invention is a heterocyclic compound represented by the following general formula (G1).

[0010] [ka]

[0011] In the general formula (G1), DBq represents a substituted or unsubstituted dibenzo[f,h]quinoxa represents a linyl group, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; , n represents 0 or 1, Ar 2 is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. A represents a substituted or unsubstituted benzobisbenzofuranyl group. r1 and Ar 2 When the arylene group represented by the formula: has substituents, the substituents are bonded to each other. may form a ring.

[0012] Another embodiment of the present invention is a compound represented by the formula (G1), wherein DBq is a substituted or unsubstituted represents a dibenzo[f,h]quinoxalinyl group, and Ar 1 is a substituted or unsubstituted carbon atom with 6 carbon atoms. represents an arylene group having a number of 1 to 13, n represents 0 or 1, and Ar 2 is substituted or unsubstituted A represents an arylene group having 6 to 13 carbon atoms, and A represents a substituted or unsubstituted benzobisbenzo It represents a furanyl group. In addition, the carbon atoms that do not constitute the furan ring in the benzobisbenzofuranyl group Of these, one of the carbon atoms adjacent to the carbon atom bonded to the oxygen atom of the furan ring is Ar 2 Combine with Also, Ar 1 and Ar 2 When the arylene group represented by the formula (I) has a substituent, the substituent is They may be bonded together to form a ring.

[0013] Another embodiment of the present invention is a heterocyclic compound represented by the following general formula (G2).

[0014] [ka]

[0015] In the general formula (G2), A represents a substituted or unsubstituted benzobisbenzofuranyl group. and R 1 ~R 9 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 6 to 4 carbon atoms. 13 represents a substituted or unsubstituted aryl group, Ar 1 is replaced or omitted. represents an arylene group having 6 to 13 carbon atoms, n represents 0 or 1, and Ar 2 also substitutes or an unsubstituted arylene group having 6 to 13 carbon atoms. 1 and Ar 2 Represented by When the arylene group has substituents, the substituents may be bonded to each other to form a ring.

[0016] In the above structure, Ar in general formula (G1) or general formula (G2) 2 is replaced or an unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group, Characteristically, n is 0.

[0017] In the above structure, Ar in general formula (G1) or general formula (G2) 2 is replaced or an unsubstituted m-phenylene group or a substituted or unsubstituted biphenyl-3,3'- It is characterized in that it represents a diyl group and n is 0.

[0018] In each of the above structures, A in the general formula (G1) or (G2) is a group represented by the following general formula: It is any one of general formulas (A1) to (A3), and in general formula (A1) to (A3), Among the carbon atoms that do not constitute the furan ring, the carbon atom adjacent to the carbon atom that bonds to oxygen in the furan ring Any one of Ar 2 It is characterized by binding to

[0019] [ka]

[0020] However, in the general formulae (A1) to (A3), the benzene ring may have a substituent. The substituents are substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted a cycloalkyl group having 5 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, Either:

[0021] Another aspect of the present invention is a compound represented by the following structural formula (101), (107), or (149): It is a heterocyclic compound represented by (150).

[0022] [ka]

[0023] The heterocyclic compound according to one embodiment of the present invention is a material with a high T1 level, and therefore, phosphorus It can be used as a host material that can be combined with a light-emitting substance (dopant) such as an optical material. This can be done.

[0024] Furthermore, the heterocyclic compound of one embodiment of the present invention is a material with a high electron-transporting property. The present invention can be applied to the EL light-emitting layer of an optical element, as well as to an electron transport layer. The heterocyclic compound of the present invention is a light-emitting material. It can be used not only as a host material in combination with a substance, but also as an emitting material. Therefore, a light-emitting element using a heterocyclic compound according to one embodiment of the present invention can be This is included in the embodiments.

[0025] That is, another embodiment of the present invention is a substituted or unsubstituted dibenzo[f,h]quinoxalyl a substituted or unsubstituted benzobisbenzofuranyl group and a substituted or unsubstituted benzobisbenzofuranyl group The present invention is a light-emitting device using a heterocyclic compound characterized in that the heterocyclic compound is bonded via an arylene group represented by the formula: .

[0026] Another embodiment of the present invention is a substituted or unsubstituted dibenzo[f,h]quinoxalinyl and a substituted or unsubstituted benzobisbenzofuranyl group. The benzobisbenzofuranyl group is bonded via an arylene group and does not constitute a furan ring. Among the carbons, one of the carbons adjacent to the carbon bonded to oxygen in the furan ring is The light-emitting device uses a heterocyclic compound that is bonded to an arylene group.

[0027] In each of the above structures, the light-emitting element has a light-emitting layer, and the light-emitting layer contains the heterocyclic compound and and a luminescent material.

[0028] Another embodiment of the present invention is not only a light-emitting device having a light-emitting element, but also a lighting device having a light-emitting device. Therefore, the light-emitting device in this specification includes an image display device. It also refers to a light source (including lighting equipment) with a connector, such as an FP C (Flexible printed circuit) or TCP (Tape Module with Carrier Package attached, printed on TCP A module with a wiring board or a light emitting element with COG (Chip On Glass) All modules in which an IC (integrated circuit) is directly mounted using the ) method are also included in the light-emitting device. do. [Effects of the Invention]

[0029] According to one embodiment of the present invention, a novel heterocyclic compound can be provided. It is possible to provide a novel heterocyclic compound capable of improving molecular properties. According to one embodiment of the present invention, a novel heterocyclic compound having good luminous efficiency and heat resistance can be provided. In addition, in one embodiment of the present invention, a novel heterocyclic compound that can be used for a light-emitting element is In addition, in one embodiment of the present invention, a compound that can be used for an EL layer of a light-emitting element can be provided. In particular, it is possible to provide a novel heterocyclic compound which can be used as a light-emitting element having high heat resistance, It is possible to provide a light-emitting element that is highly efficient and consumes less power, and that has a long lifetime. According to one embodiment of the present invention, a novel light-emitting element can be provided. A novel electronic device or a novel lighting device can be provided. [Brief explanation of the drawings]

[0030] [Figure 1] 1A to 1C illustrate a structure of a light-emitting element. [Figure 2] 1A to 1C illustrate a structure of a light-emitting element. [Figure 3] 1A and 1B illustrate a light-emitting device. [Figure 4] 1A and 1B illustrate a light-emitting device. [Figure 5] 1A and 1B are diagrams illustrating electronic devices. [Figure 6] 1A and 1B are diagrams illustrating electronic devices. [Figure 7] FIG. [Figure 8] 1A and 1B are diagrams illustrating a lighting device. [Figure 9] 1A and 1B are diagrams illustrating a lighting device. [Figure 10] FIG. 1 is a diagram showing an example of a touch panel. [Figure 11] FIG. 1 is a diagram showing an example of a touch panel. [Figure 12] FIG. 1 is a diagram showing an example of a touch panel. [Figure 13] 1A and 1B are a block diagram and a timing chart of a touch sensor. [Figure 14] Circuit diagram of a touch sensor. [Figure 15] 1H-NMR chart of the heterocyclic compound shown in structural formula (101). [Figure 16] UV-visible absorption and emission spectra of the heterocyclic compound shown in structural formula (101). [Figure 17] 1H-NMR chart of the heterocyclic compound shown in structural formula (107). [Figure 18] UV-visible absorption and emission spectra of the heterocyclic compound shown in structural formula (107). [Figure 19] 1H-NMR chart of the heterocyclic compound shown in structural formula (149). [Figure 20] UV-visible absorption and emission spectra of the heterocyclic compound shown in structural formula (149). [Figure 21] 1H-NMR chart of the heterocyclic compound shown in structural formula (150). [Figure 22] UV-visible absorption and emission spectra of the heterocyclic compound shown in structural formula (150). [Figure 23] 1A and 1B are diagrams illustrating light-emitting elements. [Figure 24] FIG. 10 is a graph showing current density-luminance characteristics of Light-emitting Elements 1 to 4. [Figure 25] FIG. 10 is a graph showing voltage-luminance characteristics of Light-Emitting Elements 1 to 4. [Figure 26] FIG. 10 shows luminance-current efficiency characteristics of Light-Emitting Elements 1 to 4. [Figure 27] FIG. 10 is a graph showing voltage-current characteristics of Light-Emitting Elements 1 to 4. [Figure 28] FIG. 10 shows emission spectra of Light-Emitting Elements 1 to 4. [Figure 29] 10 shows the reliability of Light-Emitting Elements 1 to 4. [Figure 30] 10 is a graph showing changes over time in the external quantum efficiency characteristics of the light-emitting elements 1 to 3 and the comparative light-emitting element 5. FIG. [Figure 31] Mass spectrum of 2mBbfPDBq. [Figure 32] Mass spectrum of 2mBbfPDBq. DETAILED DESCRIPTION OF THE INVENTION

[0031] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the embodiments described below. It is not to be construed as being limited to the

[0032] The words "film" and "layer" may be used interchangeably depending on the situation. For example, the term "conductive layer" can be replaced with "conductive film." ". Alternatively, for example, the term "insulating film" may be used. It may be possible to change the term to "insulating layer."

[0033] (Embodiment 1) In this embodiment, a heterocyclic compound which is one embodiment of the present invention will be described.

[0034] The heterocyclic compound shown in this embodiment is a substituted or unsubstituted dibenzo[f,h]quinoxa a substituted or unsubstituted benzobisbenzofuranyl group; The heterocyclic compound is characterized in that the ring is bonded via a substituted arylene group.

[0035] Generally, by increasing the number of fused rings that form the molecular structure of an organic compound, The organic compound with this structure has higher heat resistance as the molecular weight increases, and is used in light-emitting devices. However, simply increasing the number of fused rings is not enough. The molecular structure is more planar, which makes it easier for thin films of organic compounds to crystallize. This can lead to a decrease in the heat resistance of the compound, a decrease in the triplet excited level (T1 level) of the compound, and even the solubility of the compound. This leads to the problem that the synthesis and purification of the compound becomes difficult due to the reduced hydrolysis. In contrast, the heterocyclic compound according to one embodiment of the present invention is an organic compound formed by using a fused ring containing a heteroatom. By extending the molecular skeleton, compounds with high T1 levels can be obtained. The highly planar dibenzo[f,h]quinoxalinyl group and benzobisbenzofuranyl group are By bonding via the olefin group, a bulky compound is formed, which suppresses crystallization and improves heat resistance. Therefore, the heterocyclic compound described in this embodiment can be expressed by the following general formula ( G1) is a heterocyclic compound having a structure represented by the formula:

[0036] [ka]

[0037] In the general formula (G1), DBq is a substituted or unsubstituted dibenzo[f,h]quinoxa represents a linyl group, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; , n represents 0 or 1, Ar 2 is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. A represents a substituted or unsubstituted benzobisbenzofuranyl group. r 1 and Ar 2 When the arylene group represented by the formula: has substituents, the substituents are bonded to each other. may form a ring.

[0038] In addition, in another embodiment, in the heterocyclic compound represented by the general formula (G1), DBq represents a substituted or unsubstituted dibenzo[f,h]quinoxalinyl group, and Ar 1 is replaced or an unsubstituted arylene group having 6 to 13 carbon atoms, n represents 0 or 1, Ar 2 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and A represents a substituted or It represents an unsubstituted benzobisbenzofuranyl group. Among the carbon atoms that do not constitute the furan ring, either the carbon atom that is bonded to the oxygen atom of the furan ring or the carbon atom adjacent to it One, Ar 2 Also, Ar 1 and Ar 2 The arylene group represented by When present, the substituents may be bonded to each other to form a ring.

[0039] Ar in general formula (G1) 1 or Ar 2 As an arylene group having 6 to 13 carbon atoms represented by is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, ... and substituted or unsubstituted biphenyldiyl groups, and substituted or unsubstituted fluorenediyl groups. More specifically, the arylene groups shown in the following structural formulas (α1) to (α15) can be mentioned. can be.

[0040] [ka]

[0041] In the general formula (G1), the substituted or unsubstituted benzobisbenzofuran represented by A is Among the furanyl groups, the unsubstituted benzobisbenzofuranyl group is represented by the following general formula (A1) to general formula (A2). (A7) is either one of the following.

[0042] [ka]

[0043] In addition, in the general formula (G1), the benzobisbenzofuranyl group represented by A has a substituent. In this case, the benzene ring in the general formulae (A1) to (A7) may have a substituent. The substituents include substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, Substituted cycloalkyl groups having 5 to 7 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms Examples of such groups include aryl groups.

[0044] In addition, when the general formulae (A1) to (A7) have an alkyl group having 1 to 6 carbon atoms as a substituent, Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a s ec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, s ec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl group, sec-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3- Examples include a dimethylbutyl group.

[0045] In addition, the general formulae (A1) to (A7) each have a cycloalkyl group having 5 to 7 carbon atoms as a substituent. Specific examples of such groups include cyclopentyl, cyclohexyl, and cycloheptyl groups. Examples include:

[0046] Furthermore, the general formulae (A1) to (A7) each have an aryl group having 6 to 13 carbon atoms as a substituent. Specific examples of the alkyl group include a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, an iridium group, and an aryl group. Examples thereof include an aryl group and an aryl group.

[0047] The substitution in the general formula (G1) is preferably a methyl group, an ethyl group, an n-propyl group, or an n-propyl group. butyl group, isopropyl group, sec-butyl group, tert-butyl group, n-pentyl group, Alkyl groups with 1 to 6 carbon atoms, such as n-hexyl groups, phenyl groups, o-tolyl groups, m- Tolyl group, p-tolyl group, 1-naphthyl group, 2-naphthyl group, 2-biphenyl group, 3-biphenyl group phenyl group, aryl group having 6 to 12 carbon atoms such as 4-biphenyl group, These substituents may be bonded to each other to form a ring. For example, the fluorene-diyl group, which is an arylene group, has two phenyl groups at the 9-position as substituents. When the phenyl is a 9,9-diphenyl-9H-fluorene-2,7-diyl group having the formula Even if the fluorenyl groups are bonded to each other to form a spiro-9,9'-bifluorene-2,7-diyl group, good.

[0048] Another structure of the heterocyclic compound of one embodiment of the present invention is a heterocyclic compound represented by the following general formula (G2): It is a heterocyclic compound having the structure:

[0049] [ka]

[0050] In the general formula (G2), A represents a substituted or unsubstituted benzobisbenzofuranyl group. and R 1 ~R 9 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 6 to 6 carbon atoms. 13 represents a substituted or unsubstituted aryl group, Ar 1 is replaced or omitted. represents an arylene group having 6 to 13 carbon atoms, n represents 0 or 1, and Ar 2 also substitutes or an unsubstituted arylene group having 6 to 13 carbon atoms. 1 and Ar 2 Represented by When the arylene group has substituents, the substituents may be bonded to each other to form a ring.

[0051] Ar in general formula (G2) 1 or Ar 2 Specific examples of arylene groups having 6 to 13 carbon atoms are Examples include arylene groups represented by the following structural formulas (α1) to (α15).

[0052] [ka]

[0053] In addition, in the general formula (G2), the substituted or unsubstituted benzobisbenzofuran represented by A is Among the furanyl groups, the unsubstituted benzobisbenzofuranyl group is represented by the following general formula (A1) to general formula (A2). (A7) is either one of the following.

[0054] [ka]

[0055] In addition, in the general formula (G2), the benzobisbenzofuranyl group represented by A has a substituent. In this case, the benzene ring in the general formulae (A1) to (A7) may have a substituent. The substituents include substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, Substituted cycloalkyl groups having 5 to 7 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms Examples of such groups include aryl groups.

[0056] In addition, when the general formulae (A1) to (A7) have an alkyl group having 1 to 6 carbon atoms as a substituent, Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a s ec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, s ec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl group, sec-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3- Examples include a dimethylbutyl group.

[0057] In addition, the general formulae (A1) to (A7) each have a cycloalkyl group having 5 to 7 carbon atoms as a substituent. Specific examples of such groups include cyclopentyl, cyclohexyl, and cycloheptyl groups. Examples include:

[0058] Furthermore, the general formulae (A1) to (A7) each have an aryl group having 6 to 13 carbon atoms as a substituent. Specific examples of the alkyl group include a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, an iridium group, and an aryl group. Examples thereof include an aryl group and an aryl group.

[0059] In addition, R in general formula (G2) 1 ~R 9 Specific examples of alkyl groups having 1 to 6 carbon atoms include: is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, Isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group , tert-pentyl group, neopentyl group, hexyl group, isohexyl group, sec-hexyl group Cyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2-methylpentyl group butyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group etc.

[0060] In addition, R in general formula (G2) 1 ~R 9 Specific examples of the aryl group having 6 to 13 carbon atoms include For example, phenyl group, biphenyl group, tolyl group, naphthyl group, xylyl group, fluorenyl group and indenyl groups.

[0061] The substitution in the general formula (G2) is preferably a methyl group, an ethyl group, an n-propyl group, or an n-propyl group. butyl group, isopropyl group, sec-butyl group, tert-butyl group, n-pentyl group, Alkyl groups with 1 to 6 carbon atoms, such as n-hexyl groups, phenyl groups, o-tolyl groups, m- Tolyl group, p-tolyl group, 1-naphthyl group, 2-naphthyl group, 2-biphenyl group, 3-biphenyl group phenyl group, aryl group having 6 to 12 carbon atoms such as 4-biphenyl group, These substituents may be bonded to each other to form a ring. For example, the fluorene-diyl group, which is an arylene group, has two phenyl groups at the 9-position as substituents. When the phenyl is a 9,9-diphenyl-9H-fluorene-2,7-diyl group having the formula Even if the fluorenyl groups are bonded to each other to form a spiro-9,9'-bifluorene-2,7-diyl group, good.

[0062] Next, specific structural formulas of the heterocyclic compound according to one embodiment of the present invention are shown below. However, the present invention is not limited to these.

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066]

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[0076]

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[0081]

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[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] The heterocyclization compounds represented by the above structural formulas (101) to (184) and (201) to (400) are The compound is an example of the heterocyclic compound represented by the above general formula (G1) or (G2), The heterocyclic compound according to one embodiment of the present invention is not limited to these.

[0092] Next, a method for synthesizing a heterocyclic compound represented by the following general formula (G1), which is one embodiment of the present invention, will be described. An example will be described. The organic compound represented by general formula (G1) can be synthesized by the following method. Various reactions can be applied. For example, the following method can be used to convert a compound represented by the general formula (G1 However, an organic compound represented by the general formula ( The synthesis method of the organic compound represented by G1) is not limited to the following synthesis method.

[0093] [ka]

[0094] In the general formula (G1), DBq is a substituted or unsubstituted dibenzo[f,h]quinoxa represents a linyl group, and Ar1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; , n represents 0 or 1, Ar 2 is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. A represents a substituted or unsubstituted benzobisbenzofuranyl group. r 1 and Ar 2 When the arylene group represented by the formula: has substituents, the substituents are bonded to each other. A ring may be formed by a carbon atom not constituting the furan ring of the benzobisbenzofuranyl group. In the above, one of the carbon atoms adjacent to the carbon atom bonded to the oxygen atom of the furan ring is Ar 2 Combined with That's fine.

[0095] The synthesis scheme (A) of the heterocyclic compound represented by the general formula (G1) is shown below. As shown in the synthesis scheme (A), a dibenzo[f,h]quinoxaline compound (compound 1) and By coupling with a benzobisbenzofuran compound (compound 2), A heterocyclic compound represented by formula (G1) can be synthesized.

[0096] [ka]

[0097] In the synthetic scheme (A), DBq is a substituted or unsubstituted dibenzo[f,h ] represents a quinoxalinyl group, and Ar 1 is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. represents an alkyl group, n represents 0 or 1, and Ar 2 is a substituted or unsubstituted group having 6 to 13 carbon atoms. A represents an arylene group represented by the formula: Also, Ar 1 and Ar 2When the arylene group represented by the formula (I) has a substituent, the substituent is They may be bonded together to form a ring.

[0098] In addition, in synthetic scheme (A), the Suzuki-Miyaura coupling reaction using a palladium catalyst When responding, X 1 and X 2 is a halogen group, a boronic acid group, an organic boron group, or a triflate The halogen group is preferably iodine, bromine or chlorine. In the reaction, bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride palladium compounds such as tetrakis(triphenylphosphine)palladium(0) and tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexyl Cylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexyl Phosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine Ligands such as the following can be used.

[0099] In addition, in the reaction shown in the synthesis scheme (A), an organic salt such as sodium tert-butoxide is used. and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used. In addition, toluene, xylene, benzene, tetrahydrofuran, dioxane, The solvents that can be used include ethanol, methanol, water, etc. The reagents are not limited to those mentioned above.

[0100] In addition, the reaction in synthetic scheme (A) is not limited to the Suzuki-Miyaura coupling reaction. Instead, the Migita-Kosugi-Stille coupling reaction using organotin compounds and the Grignard Kumada-Tamao-Colew coupling reaction using a reagent, and Negishi coupling reaction using an organozinc compound A pulling reaction, a reaction using copper or a copper compound, or the like may also be used.

[0101] In the synthetic scheme (A), when the Migita-Kosugi-Stille coupling reaction is used, X 1 and X 2 One of the groups represents an organotin group, and the other represents a halogen group. Either Compound 1 or Compound 2 represents an organotin compound.

[0102] In the synthetic scheme (A), when the Kumada-Tamao-Corleau coupling reaction is used, X 1 and X 2 One of them represents a magnesium halide group, and the other represents a halogen group. That is, either Compound 1 or Compound 2 represents a Grignard reagent.

[0103] In the synthetic scheme (A), when the Negishi coupling reaction is used, X 1 and X 2 Hado One of them represents an organic zinc group, and the other represents a halogen group. Either one of Compound 2 represents an organic zinc compound.

[0104] In the synthesis of the organic compound (G1) of the present invention, the synthesis method is not limited to the synthesis scheme (A). It is not something that can be done.

[0105] An example of a method for synthesizing a heterocyclic compound has been described above as one embodiment of the present invention. is not limited to this, and may be synthesized by other synthesis methods.

[0106] Note that the heterocyclic compound according to one embodiment of the present invention has an electron-transport property and a hole-transport property. Therefore, it can be used as a host material in the light-emitting layer, or in the electron transport layer or hole transport layer. In addition, since it is a material with a high T1 level, it can be used as a material that emits phosphorescence (phosphorescent material). It is preferable to use them in combination as a host material. These heterocyclic compounds can be used as light-emitting materials in light-emitting devices. A light-emitting element including the substance is also included in one embodiment of the present invention.

[0107] Furthermore, by using the heterocyclic compound of one embodiment of the present invention, a light-emitting element and an emitter element with high emission efficiency can be obtained. It is possible to realize an optical device, an electronic device, or a lighting device. An element, a light-emitting device, an electronic device, or a lighting device can be realized.

[0108] Note that one embodiment of the present invention has been described in this embodiment. However, the present invention is not limited to these embodiments. In other words, various inventive aspects are described in this and other embodiments. Therefore, one embodiment of the present invention is not limited to a specific embodiment. Although an example in which the present invention is applied to a light-emitting element is shown, one embodiment of the present invention is not limited thereto. Depending on the situation, one embodiment of the present invention may be applied to devices other than light-emitting elements. Depending on the situation, one embodiment of the present invention does not necessarily need to be applied to a light-emitting element.

[0109] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiments. can be done.

[0110] (Embodiment 2) In this embodiment, a light-emitting element which is one embodiment of the present invention will be described with reference to FIGS.

[0111] The light-emitting element shown in this embodiment has a pair of electrodes (a first electrode (anode) 101 and a second electrode ( An EL layer 102 including a light-emitting layer 113 is sandwiched between the cathode 103 and the cathode 104. The EL layer 102 is In addition to the light-emitting layer 113, a hole injection layer 111, a hole transport layer The electron transport layer 112, the electron transport layer 114, the electron injection layer 115, and the like are formed.

[0112] When a voltage is applied to such a light-emitting element, holes injected from the first electrode 101 side and the electrons injected from the second electrode 103 side recombine in the light-emitting layer 113, The energy generated by the photo-irradiation causes the light-emitting material, such as an organometallic complex, contained in the light-emitting layer 113 to emit light. will light up.

[0113] The hole injection layer 111 in the EL layer 102 is a hole transport layer 112 or a light emitting layer 113. For example, a layer that can inject holes into a material with high hole transport properties and an access In this case, the hole is absorbed by the acceptor material. When electrons are extracted from a material with high transport properties, holes are generated. Holes are injected from the hole injection layer 111 to the light emitting layer 113 via the hole transport layer 112. The hole injection layer 111 may be made of a material with high hole injection properties. Butane oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide Other examples include phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine. Phthalocyanine compounds such as phthalocyanine (CuPC), 4,4'-bis[N-(4-diphenyl N,N'-phenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) -Bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl -(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD) and other aromatic amines compounds, or poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonyl ester) The hole injection layer 111 may also be formed from a polymer such as PEDOT / PSS (abbreviation: PEDOT / PSS). It is possible.

[0114] A specific example of manufacturing the light-emitting element described in this embodiment mode will be described below.

[0115] The first electrode (anode) 101 and the second electrode (cathode) 103 are made of a metal, an alloy, an electrically conductive material, or the like. In particular, indium oxide, Indium tin oxide, silicon or silicon oxide containing Indium oxide-tin oxide, Indium oxide-zinc oxide (Indium Zinc Oxide) ide), indium oxide containing tungsten oxide and zinc oxide, gold (Au), platinum (Pt), Nickel (Ni), Tungsten (W), Chromium (Cr), Molybdenum (Mo ), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti) In addition to these, elements belonging to Groups 1 and 2 of the periodic table, such as lithium (Li) and cesium (Ce), Alkali metals such as cesium (Cs), calcium (Ca), strontium (Sr), etc. alkaline earth metals, magnesium (Mg), and alloys containing these (MgAg, Al rare earth metals such as Li, europium (Eu), ytterbium (Yb) and It is possible to use alloys containing graphene, graphene compounds such as graphene and graphene oxide. The first electrode (anode) 101 and the second electrode (cathode) 103 may be, for example, The film can be formed by a sputtering method, a vapor deposition method (including a vacuum vapor deposition method), or the like.

[0116] The hole-injecting layer 111 and the hole-transporting layer 112 may be formed of a material having a high hole-transporting property. Aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, polymer compounds (oligomers, Various organic compounds such as dendrimer, polymer, etc. can be used. , 1×10 -6 cm 2 It is preferable that the material has a hole mobility of .gtoreq. / Vs. The layer formed using a substance having a high hole transporting property may be a single layer or a stack of two or more layers. Specific examples of organic compounds that can be used as hole transporting materials are listed below. do.

[0117] For example, the aromatic amine compound is N,N'-di(p-tolyl)-N,N'-diphenyl Nyl-p-phenylenediamine (DTDPPA), 4,4'-bis[N-(4-diphenyl phenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DN TPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyla] 4,4'-bis[N-(1-naphthyl)-N-phenyl]benzene (abbreviation: DPA3B), N,N'-bis(3-phenylamino)biphenyl (abbreviation: NPB or α-NPD) (1,1'-diphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamino TPD, 4,4',4''-tris(carbazol-9-yl)triphenyl Tris(N,N-diphenylamino) Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methyl (triphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4, 4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino] ]biphenyl (abbreviation: BSPB), and the like.

[0118] Specific examples of carbazole derivatives include 3-[N-(9-phenylcarbazole) [N-3-yl]-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPC A1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenyla 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzPCA2), -N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazol Other examples include 4,4'-di(N- Carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)biphenyl] 9-[4-(10-phenyl-9-anthoxyphenyl)phenyl]benzene (abbreviation: TCPB), 1,4-bis[4- (N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. It is possible.

[0119] Furthermore, examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthalene) butyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di (1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene Helical (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl) 9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene 9,10-diphenylanthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2 -tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methylanthracene) 2-tert-butyl-9,1 0-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1- naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1 -naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene 10,10'-diphenyl-9,9'-bianthryl, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl anthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'- Bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetracene tetra(tert-butyl)perylene, etc. In addition, pentacene, coronet, etc. In this way, 1×10 -6 cm 2 / Vs or more hole mobility It is more preferable to use aromatic hydrocarbons having 14 to 42 carbon atoms. The aromatic hydrocarbon may have a vinyl skeleton. Examples of the diphenyl ether include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: D PVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene Examples include DPVPA (abbreviation: DPVPA).

[0120] Furthermore, poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenyl ether) Nylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl amino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide]( abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. can.

[0121] The acceptor materials used in the hole injection layer 111 and the hole transport layer 112 are , 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation :F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4 , 5,8,9,12-hexaazatriphenylene (HAT-CN) and other electron-withdrawing groups (halo In particular, compounds with hydroxyl groups such as HAT-CN can be mentioned. Compounds in which electron-withdrawing groups are bonded to condensed aromatic rings containing multiple heteroatoms are thermally stable. Further, oxides of metals belonging to groups 4 to 8 in the periodic table are preferred. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, Molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide have high electron-accepting properties. Among these, molybdenum oxide is particularly preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. It is preferable because it is easy to do.

[0122] The light-emitting layer 113 is a layer containing a light-emitting substance. The phosphorescent light-emitting material may be specifically an organic In the light-emitting layer 113, an organic metal complex (guest material) is used. In this case, a substance with a higher triplet excitation energy than the organometallic complex is used as the host material. In addition to the light-emitting material, the light-emitting layer 113 preferably contains When carriers (electrons and holes) recombine in the excited state, an exciplex (also called an exciplex) is formed. Two types of organic compounds (the above-mentioned host materials) that can be combined to form a In order to efficiently form an exciplex, To achieve this, we need compounds that readily accept electrons (materials with electron transport properties) and compounds that readily accept holes. It is particularly preferable to combine the compound with a hole-transporting compound. A material with electron transport properties and a material with hole transport properties are combined to form an exciplex. When the host material is a mixture of a material having electron transport properties and a material having hole transport properties, By adjusting the ratio, the carrier balance between holes and electrons in the light-emitting layer can be optimized. By optimizing the carrier balance between holes and electrons in the light-emitting layer, This can prevent the recombination of electrons and holes from occurring in a biased region in the light-emitting layer. By suppressing the bias in the region, the reliability of the light-emitting element can be improved.

[0123] In addition, a compound that is easy to accept electrons and is preferably used to form the above exciplex ( As materials with electron transport properties, π-electron deficient heteroaromatic compounds such as nitrogen-containing heteroaromatic compounds are Aromatic compounds and metal complexes can be used. Specifically, bis(10-hydroxybenzoates) Bis(2-methyl-8-benzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), -quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq ), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzo[ oxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzo[ zothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and other metal complexes, such as 2- (4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxazolidinyl Azole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-te rt-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[ 5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzyl Benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazo 2,2',2''-(2-yl)phenyl]-9H-carbazole (abbreviation: CO11) -(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) ) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1- Polyazolidinedione such as phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds with a phenyl skeleton and 2-[3-(dibenzothiophen-4-yl)phenyl] ]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'- (Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxa Phosphorus (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9- 2mCzBPD Bq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl] Dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzyl) (benzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mD BTPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl] Dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-bis[ 3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm ), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6 mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl] Heterocyclization of diazine skeletons such as 4,6mCzP2Pm Compounds such as 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl]-9H-carbazol-3-yl 4,6-diphenyl-1,3,5-triazine (abbreviated as '4,6-diphenyl-1,3,5-triazine- ...') Heterocyclic compounds with triazine skeletons such as PCCzPTzn and 3,5-bis[ 3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) , 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) Among the above, heterocyclic compounds having a pyridine skeleton, such as Heterocyclic compounds with triazine skeletons and heterocyclic compounds with pyridine skeletons are reliable. In particular, diazine (pyrimidine or pyrazine) skeletons and triazine The heterocyclic compound having a skeleton has a high electron transport property and also contributes to a reduction in driving voltage.

[0124] In addition, a compound that is easy to accept holes and is preferable for use in forming the above exciplex ( As a material with hole transport properties, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives) In particular, an aromatic amine or an indole derivative can be suitably used. , 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro- 9,9'-Bifluorene (abbreviation: PCASF), 4,4',4''-tris[N-(1- Naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 2 ,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro- 9,9'-bifluorene (abbreviation: DPA2SF), N,N'-bis(9-phenylcarbamoyl) (3-phenyl-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA) 2B), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl ) Diphenylamine (abbreviation: DPNF), N,N',N''-triphenyl-N,N', N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triazol-1 amine (abbreviation: PCA3B), 2-[N-(4-diphenylaminophenyl)-N-phenyl N,N'-bis[4 -(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylphenyl Fluorene-2,7-diamine (abbreviation: YGA2F), NPB, N,N'-bis(3-methyl) (1,1'-biphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl] 4-phenyl-4'-(9-phenylamino)biphenyl (abbreviation: DPAB), BSPB, (phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl mBPA FLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-di Methyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2-yl] 1H-amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL) , PCzPCA1, 3-[N-(4-diphenylaminophenyl)-N-phenylamino ]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-di phenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), DNTPD, 3,6-bis[N-(4-diphenylaminophenyl) -N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2) , PCzPCA2, 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl) 1,4'-diphenyl-4''-( 9-Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi) 1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl) 4,4'-di(1-naphthyl)-4' '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BNBB), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl )amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 9,9-dimethyl- N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] Fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl (9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2- Amine (abbreviation: PCBASF), N-(4-biphenyl)-N-(9,9-dimethyl-9 H-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-fluorene-2 -amine (abbreviated as PCBBiF), and compounds with aromatic amine skeletons such as 1,3-biphenylsulfonyl ether ... mCP, CBP, 3,6-bis(3,5-diaminobenzoyl)benzene (phenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 9-phenyl-9 H-3-(9-phenyl-9H-carbazol-3-yl)carbazole (abbreviation: PCC P), and compounds with a carbazole skeleton such as 4,4',4''-(benzene-1,3 ,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-di Phenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibene Diazolidinylthiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorophenyl)-

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[0104]

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[0122] [ -IV), and 4,4',4''-(benzene-1, 3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[ 3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofura Examples of compounds include compounds with a furan skeleton such as mmDBFFLBi-II. Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are It is preferable because it has good reliability, high hole transport properties, and contributes to reducing the driving voltage. stomach.

[0125] In the light-emitting layer 113, the above-mentioned organometallic complex (guest material) and the host material are contained. By forming the light-emitting layer 113 in this manner, phosphorescence with high luminous efficiency can be obtained. Cut.

[0126] In addition, the light-emitting layer 113 is not limited to the single-layer structure shown in FIG. 1(A) in the light-emitting element. It may have a laminated structure of two or more layers as shown in (B). For example, the first light-emitting layer 113 (a1 ) is configured to emit fluorescent light, and the second light-emitting layer 113 (a 2) can be configured to obtain phosphorescence. In the layer from which phosphorescence is obtained, the energy from the exciplex to the dopant may be It is preferable to use a structure in which light is emitted by energy transfer. The color of light emitted from one layer may be different from the color of light emitted from the other layer even if they are the same. However, if they are different, for example, a structure in which blue light is emitted from one layer may be used. On the other hand, the other layer can be configured to emit orange or yellow light. Furthermore, each layer may contain multiple types of dopants.

[0127] When the light-emitting layer 113 has a laminated structure, the singlet excitation energy is converted into light emission. Luminescent substances, or luminescent substances that convert triplet excitation energy into luminescence, are used alone or in combination. In this case, the following can be mentioned as examples:

[0128] Examples of luminescent materials that convert singlet excitation energy into luminescence include fluorescent materials (fluorescent materials). photoactive compounds).

[0129] Fluorescent substances include N,N'-bis[4-(9H-carbazol-9-yl)fluorene] [phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S) , 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl) Triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4 '-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAP PA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]phenyl ]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,1 1-Tetra(tert-butyl)perylene (TBP), 4-(10-phenyl-9 -anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenyl Amine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9 ,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4 -phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9 ,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine( Abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl] 2DPAP PA), N,N,N',N',N'',N'',N''',N'''-octaphenyldi Benzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Marine 30, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9 H-Carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazo N-(9,10-diphenyl-2-amine) tolyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DP APA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl ]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABP hA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-cal 2Y GABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhA PhA), Coumarin 545T, N,N'-diphenylquinacridone, (abbreviation: DPQd) , rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyl BPT, 2-(2-[4-(dimethylamino)phenyl] ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: D CM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H -benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}p Propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl) (phenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl Nyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a ]Fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl propyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro- 1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-yl 2-(2-tert-butyl-6- (DCJTI) [2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H- Benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}pro Pandinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)methyl {4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl 2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-yl {4H-pyran-4-ylidene}propanedinitrile (abbreviated as BisDC JTM) and others.

[0130] Examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials (phosphors Fluorescent compounds and TADF materials that exhibit TADF The delayed fluorescence in TADF materials is similar to that of ordinary fluorescence. It is a type of light emission that has a spectrum and has a remarkably long lifetime. Its lifetime is 1×10-6 seconds or more Above, preferably 1 x 10 -3 More than a second.

[0131] Phosphorescent substances include bis{2-[3',5'-bis(trifluoromethyl)phenyl]phenyl} Nyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(C F3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridin Nat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIracac ), tris(2-phenylpyridinato)iridium(III) (abbreviation: [Ir(ppy) 3]), bis(2-phenylpyridinato)iridium(III) acetylacetonate ( Abbreviation: [Ir(ppy)2(acac)]), tris(acetylacetonato)(monophenyl Anthroline) terbium(III) (abbreviation: [Tb(acac)3(Phen)]), Bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [ Ir(bzq)2(acac)]), 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’ ) Iriji Ir(bt)2(acac) [2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C 3’ ]iridium( III) Acetylacetonate (abbreviation: [Ir(btp)2(acac)]), bis(1 -Phenylisoquinolinato-N,C 2’ ) Iridium(III) acetylacetonate ( Abbreviation: [Ir(piq)2(acac)]), (acetylacetonato)bis[2,3-bis(acetylacetonato) [Ir(F dpq)2(acac)]), (acetylacetonato)bis(3,5-dimethyl-2-furan [Ir(mppr-Me)2(aca c)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenyl [Ir(mppr-iPr)2(acac) ]), (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium (III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-trifluoromethyl) (phenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(t ppr)2(dpm)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium Ir(III) (abbreviation: [Ir(dppm)2(acac)]), 2,3,7,8,12, 13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), tris(1,3-diphenyl-1,3-propanedionato)(monofena (Eu(DBM)3(Phen)]), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthate) Examples include [Eu(TTA)3(Phen)], It can be obtained.

[0132] TADF materials include, for example, fullerenes and their derivatives, and activators such as proflavine. Lysine derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), Cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or para Examples of the metal-containing porphyrin include metal-containing porphyrins containing palladium (Pd). For example, protoporphyrin-tin fluoride complex (abbreviated as SnF2 (Proto IX), mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (abbreviated as SnF2(Hemato IX)), Coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III-4Me), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(O EP), etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), Examples include octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP). Furthermore, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2, 3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ ) and other heterocyclic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring. In addition, a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring can be directly bonded to each other. The resulting materials exhibit the donor properties of π-electron-rich heteroaromatic rings and the acceptor properties of π-electron-deficient heteroaromatic rings. This is particularly preferable because the bond strength between S1 and T1 is increased and the energy difference between S1 and T1 is reduced.

[0133] The electron transport layer 114 is a layer containing a substance with a high electron transport property (also referred to as an electron transport compound). The electron transport layer 114 is made of tris(8-quinolinolato)aluminum (abbreviation: Alq3 ), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), Be Bq2, BAlq, bis[2-(2-hydroxyphenyl)benzoxazolato]zinc ( Abbreviation: Zn(BOX)2), bis[2-(2-hydroxyphenyl)benzothiazol-ato] Metal complexes such as zinc (abbreviated as Zn(BTZ)2) can be used. OXD-7, TAZ, 3-(4-tert-butylphenyl)-4-(4-ethylphenyl) p-EtTAZ , Bathophenanthroline (abbreviated as Bphen), Bathocuproine (abbreviated as BCP), 4 ,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs Heteroaromatic compounds such as poly(2,5-pyridinediyl) can also be used. ) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co -(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctyl fluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] Polymer compounds such as PF-BPy (abbreviation: PF-BPy) can also be used. is mainly 1×10 -6 cm 2 It is a material with electron mobility of 1 / Vs or more. Any substance other than those mentioned above may be used for the electron-transporting layer 114 as long as it has a higher electron-transporting property than the above-mentioned substances. Good too.

[0134] The electron transport layer 114 may be a single layer or may be a laminate of two or more layers made of the above-mentioned materials. The structure may be such that:

[0135] The electron injection layer 115 is a layer containing a substance with high electron injection properties. Lithium fluoride (LiF), Cesium fluoride (CsF), Calcium fluoride (CaF2), Alkali metals, alkaline earth metals, or their derivatives, such as lithium oxide (LiOx) Compounds such as erbium fluoride (ErF3) can also be used. Alternatively, an electride may be used for the electron injection layer 115. The electride may be, for example, a mixed oxide of calcium and aluminum with electrons. The material constituting the electron transport layer 114 may be a material containing a high concentration of can also be used.

[0136] The electron injection layer 115 is made of a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials are formed by electron donors generating electrons in organic compounds. In this case, the organic compound is: It is preferable that the material has excellent transport properties for the generated electrons. Specifically, for example, the above-mentioned The substance constituting the electron transport layer 114 (metal complex, heteroaromatic compound, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to organic compounds. The metals are preferably alkali metals, alkaline earth metals, or rare earth metals, and more preferably lithium, cesium, magnesium, or the like. Examples of the metals include magnesium, calcium, erbium, and ytterbium. Metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, Examples of the base include barium oxide. In addition, a Lewis base such as magnesium oxide can be used. It is also possible to use organic compounds such as tetrathiafulvalene (TTF). It is also possible.

[0137] The hole injection layer 111, the hole transport layer 112, the light emitting layer 113, and the electron transport layer 114 The electron injection layer 115 can be formed by a deposition method (including a vacuum deposition method), a printing method (for example, a letterpress printing method), or the like, respectively. printing method, intaglio printing method, gravure printing method, lithographic printing method, stencil printing method, etc.), inkjet method The method may be a coating method or a combination of methods. In addition, a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron In addition to the above-mentioned materials, the injection layer 115 may contain inorganic compounds such as quantum dots or polymer compounds. (oligomers, dendrimers, polymers, etc.) may also be used.

[0138] In this manner, a light-emitting element having an EL layer sandwiched between a pair of electrodes can be manufactured.

[0139] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0140] (Embodiment 3) In this embodiment, a light-emitting element having a structure including a plurality of EL layers (hereinafter, This section explains the tandem light-emitting device.

[0141] The light-emitting element shown in this embodiment has a pair of electrodes (first electrode 201) as shown in FIG. and second electrode 204) via a charge generating layer 205. The light emitting element is a tandem type light emitting element having a first EL layer 202(1) and a second EL layer 202(2).

[0142] In this embodiment, the first electrode 201 is an electrode that functions as an anode, and the second electrode The electrode 204 functions as a cathode. 04 can have the same structure as in Embodiment 2. In addition, a plurality of EL layers (first The EL layer 202(1) and the second EL layer 202(2) are the same as the EL layer shown in the second embodiment. Both may have the same configuration, or either one may have the same configuration. That is, the first EL layer 202(1) and the second EL layer 202(2) may have the same structure but different If the configuration is the same, the second embodiment can be applied.

[0143] In addition, a plurality of EL layers (first EL layer 202(1), second EL layer 202(2)) are provided between the EL layers. The charge generating layer 205 is formed by applying a voltage to the first electrode 201 and the second electrode 204. When the organic layer is turned on, electrons are injected into one EL layer and holes are injected into the other EL layer. In this embodiment, the first electrode 201 is set to have a higher potential than the second electrode 204. When a voltage is applied in this manner, electrons are injected from the charge generating layer 205 into the first EL layer 202(1). As a result, holes are injected into the second EL layer 202(2).

[0144] The charge generating layer 205 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, it is preferable that the visible light transmittance of the charge generating layer 205 is 40% or more.) In addition, the charge generating layer 205 has a lower conductivity than the first electrode 201 and the second electrode 204. It also works.

[0145] The charge generation layer 205 is formed by adding an electron acceptor to an organic compound having high hole transport properties. Even if the structure is such that an electron donor (donor) is added to an organic compound with high electron transport properties, Alternatively, both of these structures may be stacked.

[0146] In the case where an electron acceptor is added to an organic compound having high hole transport properties, As the organic compound with high transportability, the hole injection layer 111 and the hole transport layer 1 The materials shown in 12 as having high hole transport properties can be used. For example, N Aromatic amine compounds such as PB, TPD, TDATA, MTDATA, and BSPB are used. The materials mentioned here are mainly 1×10 -6 cm 2 Hole mobility above / Vs However, if the organic compound has a higher hole transporting property than the electron transporting property, Other materials may also be used.

[0147] The electron acceptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene. Examples include fluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, etc. Further examples include oxides of metals belonging to groups 4 to 8 of the periodic table. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, Tungsten oxide, manganese oxide, and rhenium oxide are preferred because of their high electron-accepting properties. In particular, molybdenum oxide is preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. stomach.

[0148] On the other hand, in the case where an electron donor is added to an organic compound having high electron transport properties, As the organic compound having a high electron transporting property, the electron transporting compound used for the electron transport layer 114 in the second embodiment is The materials shown as having high conductivity can be used. For example, Alq, Almq3, Metal complexes with quinoline or benzoquinoline skeletons, such as BeBq2 and BAlq In addition, other oxides such as Zn(BOX)2 and Zn(BTZ)2 can be used. Metal complexes having thiazole or thiazole ligands can also be used. In addition to metal complexes, PBD, OXD-7, TAZ, Bphen, BCP, etc. can also be used. The substances mentioned here are mainly 1×10 -6 cm 2 / Vs or higher electron mobility In addition, any organic compound that has a higher electron transporting property than hole transporting property can be used. You can also use quality.

[0149] The electron donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or The metals belonging to Groups 2 and 13 of the periodic table and their oxides and carbonates are used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg) , calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, It is preferable to use cesium carbonate. The compound may be used as the electron donor.

[0150] The charge generating layer 205 is formed using the above-mentioned materials, and thus the EL layer is laminated. In addition, the formation of the charge generating layer 205 can suppress the increase in the driving voltage. The methods include deposition methods (including vacuum deposition methods), printing methods (e.g., letterpress printing, intaglio printing, etc.), , gravure printing, lithography, stencil printing, etc.), inkjet printing, coating, etc. They can be formed using either alone or in combination.

[0151] In this embodiment mode, a light-emitting element having two EL layers has been described. In this way, n (where n is 3 or more) EL layers (202(1) to 202(n)) are stacked. The same can be applied to the light emitting device according to the present embodiment. When there are multiple EL layers between a pair of electrodes, as in the case of a device, By arranging the charge generation layers (205(1) to 205(n-1)), the current density can be kept low. It is possible to emit light in a high brightness range while maintaining a low current density, which allows for long-life elements. It can be achieved.

[0152] In addition, by making the luminescent color of each EL layer different, the desired luminescent color can be obtained as a whole. For example, in a light-emitting element having two EL layers, the first By making the luminescent color of the first EL layer and the luminescent color of the second EL layer complementary to each other, It is also possible to obtain a light emitting element that emits white light as a whole. This refers to the relationship between colors that become achromatic. In other words, when light of complementary colors is mixed with each other, Specifically, blue light is emitted from the first EL layer, and white light is emitted from the second EL layer. In this case, a combination in which yellow or orange light is emitted from the EL layer of the second electrode is possible. Both the blue and yellow (or orange) emissions are the same fluorescent or phosphorescent emissions It is not necessary that the blue emission is fluorescent and the yellow (or orange) emission is phosphorescent. A combination of these may also be used, or vice versa.

[0153] The same applies to a light-emitting element having three EL layers. For example, the light-emitting element of the first EL layer The light color of the first EL layer is red, the light color of the second EL layer is green, and the light color of the third EL layer is blue. In some cases, the light emitting element as a whole can emit white light.

[0154] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0155] (Fourth embodiment) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0156] The light emitting device may be a passive matrix light emitting device or an active matrix light emitting device. The light-emitting device described in this embodiment may be a light-emitting device. Optical elements can be applied.

[0157] In this embodiment mode, an active matrix light emitting device will be described with reference to FIG. do.

[0158] 3A is a top view showing the light emitting device, and FIG. 3B is a top view showing the light emitting device along the dashed line AA in FIG. 3A. The active matrix light emitting device is formed on an element substrate 301. A pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate The pixel section 302 includes a gate line driving circuit 304 (304a and 304b). The path portion 303 and the drive circuit portions 304a and 304b are attached to the element substrate by a sealing material 305. It is sealed between the plate 301 and a sealing substrate 306 .

[0159] Further, on the element substrate 301, a driving circuit section 303 and a driving circuit section 304 are provided. signals (e.g., video signals, clock signals, start signals, reset signals, etc.) and potentials. A wiring 307 is provided for connecting the external input terminals for transmitting the signal. An example is shown in which an FPC (flexible printed circuit) 308 is provided as an internal input terminal. Although only the FPC is shown here, this FPC also includes a printed wiring board. The light emitting device in this specification may include a light emitting device body. This also includes the state in which an FPC or PWB is attached to it.

[0160] Next, the cross-sectional structure will be described with reference to FIG. and a pixel portion are formed, but here, a driver circuit portion 303 which is a source line driver circuit and , a pixel portion 302 is shown.

[0161] The driving circuit section 303 is exemplified by a configuration in which an FET 309 and an FET 310 are combined. The driving circuit section 303 is a transistor of a single polarity (either N-type or P-type). It may be formed by a circuit including an N-type transistor and a P-type transistor. In this embodiment, the driver circuit may be formed on a substrate. Although this shows an integrated driver, it is not necessary to have one, and the driver may be external rather than on the board. Circuits can also be formed.

[0162] The pixel section 302 also includes a switching FET (not shown) and a current control FET 312. The wiring (source electrode or drain electrode) of the current control FET 312 is connected to the light emitting element 3 17a and the first electrode (anode) (313a, 313b) of the light-emitting element 317b. In this embodiment, the pixel section 302 is connected to two FETs (switch An example of a configuration using a switching FET and a current control FET 312 has been shown. For example, a configuration in which three or more FETs and a capacitance element are combined can be used. good.

[0163] The FETs 309, 310, and 312 are, for example, staggered or inverted staggered transistors. Semiconductor materials that can be used for the FETs 309, 310, and 312 Examples of materials include group 13 semiconductors, group 14 (silicon, etc.) semiconductors, compound semiconductors, and oxides. Semiconductors and organic semiconductors can be used. The crystallinity of the semiconductor material is particularly The semiconductor film is not limited to the above, and for example, an amorphous semiconductor film or a crystalline semiconductor film can be used. In particular, it is preferable to use an oxide semiconductor for the FETs 309, 310, and 312. Examples of oxide semiconductors include In-Ga oxide and In-M-Zn oxide (M is A). I, Ga, Y, Zr, La, Ce, Hf or Nd). 10, 312, for example, an energy gap of 2 eV or more, preferably 2.5 eV By using an oxide semiconductor material with a voltage of 3 eV or more, more preferably 3 eV or more, The off-state current can be reduced.

[0164] In addition, the first electrodes (313a, 313b) are provided with conductive films (320a, 320b) for optical adjustment. For example, as shown in FIG. 3(B), a light-emitting element 317a and a light-emitting element 317b are stacked. When the wavelength of light extracted by the optical element 317b is different from that of the conductive film 320a, the conductive film 320b is The thickness of the insulating film 3 is different from that of the insulating film 3b. Here, a positive photosensitive acrylic resin is used as the insulator 314. In this embodiment, the first electrode (313a, 3 13b) is used as the anode.

[0165] It is also preferable to form a curved surface having a curvature at the upper or lower end of the insulator 314 . By forming the shape of the insulator 314 as described above, the film formed on the insulator 314 For example, the material of the insulator 314 may be a negative type. Either a photosensitive resin of the type I or a positive photosensitive resin can be used, and the organic compound Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride are also used. It is possible.

[0166] An EL layer 315 and a second electrode 316 are stacked on the first electrodes (313a, 313b). The EL layer 315 is provided with at least a light-emitting layer, and is connected to the first electrode (313a , 313b), an EL layer 315, and a light-emitting element (317a, 317b) consisting of a second electrode 316. b) has a structure in which the edge of the EL layer 315 is covered with a second electrode 316. The layer 315 may have a single layer structure or a stacked layer structure as shown in Embodiment 2 or 3. Furthermore, it may be different for each light-emitting element.

[0167] The first electrode 313, the EL layer 315, and the second electrode 316 are made of materials such as The materials shown in the second embodiment can be used. The first electrodes (313a, 313b) are electrically connected to the lead wiring 307 in the region 321. An external signal is input via the FPC 308. , 317b) are electrically connected to the wiring 323 in the region 322. Although not shown here, an external signal is input via the FPC 308.

[0168] In addition, although only two light-emitting elements 317 are shown in the cross-sectional view of FIG. 3B, the pixel portion 3 In 02, a plurality of light emitting elements are arranged in a matrix. The pixel section 302 includes not only a light emitting element that can emit two types of light (for example, (B, Y)), but also There are light-emitting elements that can emit three types of light (e.g., (R, G, B)), and four types (e.g., (R, G and forming light emitting elements, etc., which can emit light of (R, B, Y) or (R, G, B, W) etc. In this case, a light-emitting device capable of full color display can be formed. In order to achieve this, a light-emitting layer is formed using different materials depending on the light-emitting color of the light-emitting element (so-called "coating method"). Alternatively, a plurality of light-emitting elements may have a common light-emitting layer formed using the same material. In addition, full color may be realized by combining it with a color filter. By combining light-emitting elements that can emit several types of light, color purity and consumption can be improved. This can reduce power consumption and also emit light when combined with quantum dots. A light emitting device with improved efficiency and reduced power consumption may also be provided.

[0169] Furthermore, by bonding the sealing substrate 306 to the element substrate 301 with the sealing material 305, A space 318 surrounded by the element substrate 301, the sealing substrate 306, and the sealant 305 contains a light-emitting element. The structure is provided with elements 317a and 317b.

[0170] Furthermore, the sealing substrate 306 is provided with a color layer (color filter) 324. A black layer (black matrix) 325 is provided between the colored layers. A colored layer (color filter) adjacent to the layer (black matrix) 325 so as to overlap with the layer (black matrix) 325. Alternatively, one or both of the light emitting elements 317a and 317b may be provided. The resulting light is extracted to the outside through the colored layer (color filter) 324.

[0171] The space 318 may be filled with an inert gas (nitrogen, argon, etc.) or may be sealed. This also includes a configuration in which the substrate is filled with a sealant 305. In this case, it is preferable to perform either UV treatment or heat treatment, or a combination of these. .

[0172] It is also preferable to use epoxy resin or glass frit for the sealing material 305. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 306 include glass substrates, quartz substrates, and FRP (Fiber-Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyethylene or acrylic can be used as a sealing material. When glass frit is used, the element substrate 301 and the sealing substrate 306 are preferably bonded to each other from the viewpoint of adhesiveness. is preferably a glass substrate.

[0173] The structure of the FET electrically connected to the light emitting element differs from that shown in FIG. 3(B) in that the position of the gate electrode is FET326, FET327, and FET328 shown in FIG. 3(C) have different structures. The colored layer (color filter) 3 provided on the sealing substrate 306 may be formed as shown in FIG. 24 is positioned so as to overlap with the black layer (black matrix) 325 as shown in FIG. 3(C). Furthermore, it may be provided so as to overlap with the adjacent colored layer (color filter) 324 .

[0174] In this manner, an active matrix light emitting device can be obtained.

[0175] Further, the light-emitting device according to one embodiment of the present invention may be an active matrix light-emitting device. It is also possible to use a passive matrix light emitting device.

[0176] 4(A) and (B) show a passive matrix light-emitting device. FIG. 4B shows a top view of a matrix light-emitting device, and FIG. 4B shows a cross-sectional view thereof.

[0177] As shown in FIGS. 4A and 4B, a first electrode 402 and an EL layer (40 3a, 403b, and 403c) and a second electrode 404, a light-emitting element 405 is formed. The first electrode 402 is island-shaped and striped in one direction (horizontal direction in FIG. 4(A)). A plurality of stripes are formed on the first electrode 402. An insulating film 406 is formed on a part of the first electrode 402. A partition wall 407 made of an insulating material is provided on the insulating film 406. As shown in FIG. 4B, the side walls of the wall 407 are spaced apart from one another as they approach the substrate surface. The side wall has a slope that narrows the gap between it and the other side wall.

[0178] Since the insulating film 406 has an opening in a part above the first electrode 402, the EL layer (40 3a, 403b, 403c) and the second electrode 404 are arranged on the first electrode 402 in a desired shape. In Fig. 4(A) and Fig. 4(B), a mask such as a metal mask is used. The EL layers (403a, 403b, 403c) are formed by combining the insulating film 406 and the partition wall 407 on the insulating film 406. c) and the second electrode 404. b, EL layer 403c emits different light colors (for example, red, green, blue, yellow, orange, white, etc.). An example of this is shown below.

[0179] After the EL layers (403a, 403b, 403c) are formed, the second electrode 404 is formed. Therefore, the second electrode 404 is formed on the EL layer (403a, 403b, 403c). The first electrode 402 is not in contact with the second electrode 402 .

[0180] The sealing method is the same as that of the active matrix light emitting device. Therefore, the explanation will be omitted.

[0181] In this manner, a passive matrix light emitting device can be obtained.

[0182] For example, in this specification, a transistor or a light-emitting element is formed using various substrates. The type of substrate is not limited to a specific one. An example of the substrate is as follows: Examples include semiconductor substrates (such as single crystal substrates or silicon substrates), SOI substrates, and glass substrates. , quartz substrate, plastic substrate, metal substrate, stainless steel substrate, stainless steel Substrate with tungsten foil, tungsten substrate, substrate with tungsten foil, flexible Examples include: a flexible substrate, a laminated film, a paper containing fibrous material, or a base film. Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, or Soda lime glass, etc. Flexible substrates, laminated films, base films, etc. Examples include polyethylene terephthalate (PET) ), polyethylene naphthalate (PEN), polyethersulfone (PES), polythene There are plastics such as tetrafluoroethylene (PTFE). Examples of the material include synthetic resins such as acrylic. ester, polyvinyl fluoride, or polyvinyl chloride. Polyamide, polyimide, aramid, epoxy, inorganic vapor deposition film, paper, etc. In particular, transistors are manufactured using semiconductor substrates, single crystal substrates, SOI substrates, etc. This results in less variation in characteristics, size, or shape, and a high current supply capacity. Small size transistors can be manufactured. By configuring the circuit, it is possible to reduce the power consumption of the circuit or to increase the integration density of the circuit.

[0183] In addition, a flexible substrate is used as the substrate, and a transistor or a light-emitting element is directly formed on the flexible substrate. Alternatively, a peeling layer may be provided between the substrate and the transistor or light-emitting element. The release layer may be used to separate the semiconductor device from the substrate after the semiconductor device is partially or entirely completed thereon. The resulting structure can be used for transferring the structure to other substrates, such as transistors or light-emitting devices. The element can be transferred onto a substrate having poor heat resistance or a flexible substrate. For example, a laminated structure of inorganic films such as a tungsten film and a silicon oxide film, or a polyimide film on a substrate, A configuration in which an organic resin film such as a fluorine-based resin film is formed can be used.

[0184] That is, a transistor or a light-emitting element is formed using a substrate, and then the transistor or the light-emitting element is transferred to another substrate. Transistors or light-emitting elements are transposed and arranged on another substrate. An example of the substrate onto which the transistor or the light-emitting element is transferred is In addition to substrates on which a transistor or a light-emitting element can be formed, paper substrates, cellophane substrates, Aramid film substrate, polyimide film substrate, stone substrate, wood substrate, cloth substrate (natural fiber Fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or recycled fibers Fiber (including acetate, cupro, rayon, recycled polyester, etc.), leather substrate, or The use of these substrates allows for the formation of transistors with good characteristics. Formation of low-power transistors, manufacturing of durable devices, imparting heat resistance, lightweight It is possible to achieve a smaller or thinner size.

[0185] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0186] (Embodiment 5) In this embodiment, various electronic devices completed by applying a light-emitting device which is one embodiment of the present invention will be described. We will explain the example of a car.

[0187] As an electronic device to which a light emitting device is applied, for example, a television set (television or television (also called television receivers), computer monitors, digital cameras, digital video Cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), mobile phones These include portable game machines, mobile information terminals, sound reproduction devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are shown in Figure 5.

[0188] FIG. 5A shows an example of a television device. The television device 7100 is A display unit 7103 is built into the body 7101. The display unit 7103 displays images. It is possible to use a touch panel (input / output device) equipped with a touch sensor (input device). Note that the light-emitting device of one embodiment of the present invention can be used for the display portion 7103. In addition, the configuration in which the housing 7101 is supported by a stand 7105 is shown here. There are.

[0189] The television device 7100 can be operated using an operation switch provided on the housing 7101 or the This can be done using a separate remote control 7110 shown in Figure 711. The operation keys 7109 on the 0 allow you to control the channel and volume. The image displayed on the remote control unit 7103 can be controlled. A display unit 7107 is provided to display information output from the remote control unit 7110. You may do so.

[0190] The television device 7100 is configured to include a receiver, a modem, etc. It is possible to receive more general television broadcasts, and also to receive them by wire or wirelessly via a modem. By connecting to a communication network, it can be transmitted in one direction (sender to receiver) or two directions (transmit to receiver). It is also possible to communicate information between followers and recipients, or between recipients themselves.

[0191] FIG. 5B shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. It includes a board 7204, an external connection port 7205, a pointing device 7206, and the like. Note that the computer uses the light-emitting device of one embodiment of the present invention for the display portion 7203. The display portion 7203 can be manufactured by using a touch sensor (input device). It may also be a touch panel (input / output device) installed.

[0192] FIG. 5C shows a smartwatch, which includes a housing 7302, a display unit 7304, and an operation button 7307. 311, 7312, a connection terminal 7313, a band 7321, a clasp 7322, etc.

[0193] A display unit 7304 mounted on a housing 7302 that also serves as a bezel has a non-rectangular display area. The display unit 7304 has an icon 7305 representing the time, other icons 730 6, etc. The display portion 7304 is equipped with a touch sensor (input device). The display may be a touch panel (input / output device) mounted thereon.

[0194] The smartwatch shown in FIG. 5C can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display, Functions such as calendar, date or time display, various software (programs) It has the functions of controlling processing by wireless communication, and It has the function of connecting to a data network, and the function of transmitting or receiving various data using wireless communication. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It can have functions such as:

[0195] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity) Degrees, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, electricity Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared. The smart watch may have a light emitting device, a microphone, etc. The display portion 7304 can be manufactured by using the same.

[0196] FIG. 5(D) shows an example of a mobile phone (including a smartphone). 400 includes a housing 7401, a display unit 7402, a microphone 7406, a speaker 7405, a camera, and the like. The device is equipped with a camera 7407, an external connection section 7404, and operation buttons 7403. When a light-emitting device is manufactured by forming a light-emitting element according to one embodiment on a flexible substrate, This can be applied to a display portion 7402 having a curved surface as shown in FIG.

[0197] In a mobile phone 7400 shown in FIG. 5D, information can be displayed by touching the display portion 7402 with a finger or the like. You can also make a call or write an email using the This can be done by touching the display portion 7402 with a finger or the like.

[0198] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0199] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. It's nice.

[0200] In addition, a detection device such as a gyro sensor or an acceleration sensor is provided inside the mobile phone 7400. By doing so, the orientation of the mobile phone 7400 (portrait or landscape) is determined, and the screen display of the display unit 7402 is can be set to switch automatically.

[0201] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. The type of image displayed on the display unit 7402 can be selected by operating the button 7403. For example, the image signal to be displayed on the display unit can be switched by If the data is text data, the mode switches to display mode, and if the data is text data, the mode switches to input mode.

[0202] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0203] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light source that emits near-infrared light By using this, it is possible to capture images of finger veins, palm veins, etc.

[0204] Furthermore, as another configuration of a mobile phone (including a smartphone), Fig. 5(D'-1) and Fig. It can also be applied to a mobile phone having a structure such as 5(D'-2).

[0205] In addition, when the structure is as shown in Figure 5(D'-1) or Figure 5(D'-2), character information and Image information and the like are stored on the first surfaces 7501(1) and 7501(2) of the housings 7500(1) and 7500(2). (2), but can also be displayed on the second screen 7502(1) and 7502(2). With this structure, you can keep the mobile phone in your breast pocket. Uses text information and image information displayed on the second page 7502(1), 7502(2), etc. The person can easily verify this.

[0206] Furthermore, as an electronic device to which a light-emitting device is applied, a folding type as shown in FIGS. 6A shows a portable information terminal 931 in an unfolded state. 6(B) shows the state of the unfolded or folded state. The mobile information terminal 9310 is shown in a state in the process of changing. The portable information terminal 9310 is shown in a folded state. It is highly portable, and when unfolded, it has a seamless, wide display area that allows for excellent visibility of the display. can be.

[0207] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the space between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device of one embodiment of the present invention can be reversibly transformed into a display portion 931. A display area 9312 in the display portion 9311 is in a folded state. The display area 9312 is a display area located on the side of the portable information terminal 9310. You can display icons and shortcuts for frequently used apps and programs. This allows you to check information and launch apps smoothly.

[0208] Also, a car to which the light emitting device is applied is shown in Fig. 7(A)(B). Specifically, the outer lane of the automobile shown in FIG. Door 5101 (including the rear of the car body), tire wheel 5102, part of door 5103 The display unit 51 shown in FIG. 7B can be applied to the entire vehicle. 04, steering wheel 5105, shift lever 5106, seat 5107, inner rear bi It can be applied to a glass window such as a mirror 5108. stomach.

[0209] As described above, electronic devices and automobiles can be obtained by applying the light-emitting device which is one embodiment of the present invention. It should be noted that the electronic devices and automobiles to which the present invention can be applied are not limited to those shown in the present embodiment. , and can be applied in any field.

[0210] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0211] (Sixth embodiment) In this embodiment, a structure of a lighting device manufactured using a light-emitting element which is one embodiment of the present invention will be described. This will be explained with reference to FIG.

[0212] 8(A), (B), (C), and (D) show examples of cross-sectional views of the lighting device. (A) and (B) are bottom-emission type lighting devices that extract light from the substrate side, as shown in Figure 8( C) and (D) are top-emission lighting devices that extract light from the encapsulation substrate side.

[0213] A lighting device 4000 shown in FIG. 8A has a light-emitting element 4002 on a substrate 4001. The light emitting element 4002 has a substrate 4003 having an uneven surface on the outer side of the substrate 4001. It has a first electrode 4004 , an EL layer 4005 , and a second electrode 4006 .

[0214] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. 008. An auxiliary wiring electrically connected to the first electrode 4004. An insulating layer 4010 may be formed on the auxiliary wiring 4009. There are.

[0215] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light emitting element 4002. It is preferable that the substrate 4003 has the unevenness as shown in FIG. The efficiency of extracting light generated in 02 can be improved.

[0216] In addition, instead of the substrate 4003, as in the illumination device 4100 of FIG. 8(B), A diffusion plate 4015 may be provided on the outside.

[0217] A lighting device 4200 in FIG. 8C has a light-emitting element 4202 over a substrate 4201. The element 4202 has 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. 208. The auxiliary wiring 4206 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0219] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 4211 are provided between the sealing substrate 4211 and the light emitting element 4202. 4 may be provided. Note that since the sealing substrate 4211 has unevenness as shown in FIG. The extraction efficiency of light generated by the light emitting element 4202 can be improved.

[0220] In addition, instead of the sealing substrate 4211, a light-emitting element 4 is A diffuser plate 4215 may be provided on top of 202.

[0221] Note that the lighting device described in this embodiment includes a light-emitting element which is one embodiment of the present invention, a housing, a cover, and a light-emitting element. Alternatively, the light-emitting element may have a structure having a support base. An organometallic complex according to one embodiment of the present invention can be applied to 4205. It is possible to provide a lighting device with low power consumption.

[0222] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0223] (Embodiment 7) In this embodiment, one example of a lighting device, which is an application of the light-emitting device according to one embodiment of the present invention, will be described. An example will be described with reference to FIG.

[0224] FIG. 9 shows an example in which the light emitting device is used as an indoor lighting device 8001. It is also possible to make a large-area lighting device. By using a housing having a curved surface, it is possible to form a lighting device 8002 having a light-emitting area with a curved surface. The light-emitting element included in the light-emitting device shown in this embodiment mode is a thin film, and the design of the housing Therefore, lighting devices with a variety of elaborate designs can be formed. Furthermore, lighting devices 8003 may be provided on the walls of the room.

[0225] In addition to the above, by applying a light emitting device to some of the furniture installed in the room, The lighting device can have the following functions.

[0226] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0227] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible.

[0228] (Embodiment 8) In this embodiment, a light-emitting element according to one embodiment of the present invention or a light-emitting device according to one embodiment of the present invention is The touch panel will be described with reference to FIGS.

[0229] 10(A) and 10(B) are perspective views of the touch panel 2000. ) representative components of touch panel 2000 are shown for clarity.

[0230] The touch panel 2000 includes a display panel 2501 and a touch sensor 2595 (see FIG. 1 0(B)). The touch panel 2000 includes a substrate 2510, a substrate 2570, and a substrate It has a plate 2590.

[0231] The display panel 2501 has a plurality of pixels on a substrate 2510 and a display panel for supplying signals to the pixels. The plurality of wirings 2511 are arranged around the periphery of the substrate 2510. The wire is routed through a cable, part of which forms the terminal 2519. The terminal 2519 is an FPC2509 (1) and electrically connect.

[0232] The substrate 2590 has a touch sensor 2595 and a The plurality of wirings 2598 are routed around the periphery of the substrate 2590. The terminal 2599 is connected to the FPC 2509 (2 ) is electrically connected to the back side of the substrate 2590 for clarity. Electrodes and wiring of the touch sensor 2595 provided on the surface facing the substrate 2510 are implemented. It is shown by a line.

[0233] As the touch sensor 2595, for example, a capacitance type touch sensor can be applied. The capacitance type includes a surface capacitance type, a projected capacitance type, and the like.

[0234] Projected capacitive touch panels are classified into self-capacitance and mutual-capacitance types, which differ mainly in their drive methods. The mutual capacitance method is preferable because it allows simultaneous multi-point detection.

[0235] First, when applying a projected capacitive touch sensor, we will use Figure 10(B) to In the case of the projected capacitive type, the proximity or contact of a detection target such as a finger is detected. Various sensors can be applied that can detect.

[0236] The projected capacitive touch sensor 2595 has an electrode 2591 and an electrode 2592. The electrodes 2591 and 2592 are connected to different wirings among the plurality of wirings 2598. 10(A)(B), the electrode 2592 is repeatedly connected in one direction. A shape in which multiple quadrilaterals are repeatedly arranged and connected in one direction by wiring 2594 at the corners. The electrode 2591 also has a shape in which multiple quadrilaterals are connected at the corners, but the connected The direction in which the electrodes 2591 are connected intersects with the direction in which the electrodes 2591 are connected. The direction in which the electrode 2592 is connected is not necessarily perpendicular to the direction in which the electrode 2592 is connected. This is not necessary, and they may be arranged to form an angle greater than 0 degrees but less than 90 degrees.

[0237] It is preferable that the area of ​​the intersection of the wiring 2594 with the electrode 2592 be as small as possible. This makes it possible to reduce the area of ​​the region where no electrodes are provided, and to reduce variations in transmittance. As a result, the variation in brightness of light passing through the touch sensor 2595 can be reduced. It is possible.

[0238] The shapes of the electrodes 2591 and 2592 are not limited to this and may take various shapes. For example, multiple electrodes 2591 are arranged with as few gaps as possible, and are connected via an insulating layer. In this case, two adjacent electrodes 2592 may be provided. If a dummy electrode electrically isolated from these is provided between the two, the surface of the area with different transmittance can be This is preferable because it can reduce the product.

[0239] Next, the touch panel 2000 will be described in detail with reference to FIG. 11. 10(A) along the dashed line X1-X2.

[0240] The touch panel 2000 includes a touch sensor 2595 and a display panel 2501 .

[0241] The touch sensor 2595 is made up of electrodes 2591 and 2592 arranged in a staggered pattern in contact with the substrate 2590. and an insulating layer 2593 covering the electrodes 2591 and 2592; The electrodes 2591 are electrically connected to each other through wiring 2594. An electrode 2592 is provided between them.

[0242] The electrode 2591 and the electrode 2592 can be formed using a light-transmitting conductive material. Examples of the conductive material having light-transmitting properties include indium oxide, indium tin oxide, and indium Conductive oxides such as gallium zinc oxide, zinc oxide, and gallium-doped zinc oxide can be used. A graphene compound can also be used. When used, it can be formed by reducing, for example, graphene oxide formed in a film form. The reduction method can be by applying heat or by irradiating a laser. Cut.

[0243] The electrodes 2591 and 2592 can be formed using, for example, a conductive material having light-transmitting properties. After forming a film on the substrate 2590 by sputtering, various methods such as photolithography are used. The patterning technique can be used to remove unnecessary portions.

[0244] The material used for the insulating layer 2593 is, for example, a resin such as acrylic or epoxy, or a silicon dioxide. In addition to resins with SAN bonds, silicon oxide, silicon oxynitride, aluminum oxide, etc. An inorganic insulating material can be used.

[0245] In addition, the wiring 2594 formed in part of the insulating layer 2593 allows the adjacent electrodes 2591 to The wiring 2594 is made of the same material as the electrode 2591 and the electrode 259 By using a material with higher conductivity than the material used in 2, electrical resistance can be reduced. This is preferable because it can be done easily.

[0246] The wiring 2598 is electrically connected to the electrode 2591 or the electrode 2592. A part of the wiring 2598 functions as a terminal. , gold, platinum, silver, nickel, titanium, tungsten, chromium, molybdenum, iron, cobalt Metallic materials such as copper or palladium, or alloy materials containing such metallic materials can be used. do.

[0247] In addition, the terminal 2599 electrically connects the wiring 2598 and the FPC 2509(2). Terminal 2599 is made of various anisotropic conductive films (ACF). Conductive Film) and Anisotropic Conductive Paste (ACP) tropic conductive paste) can be used.

[0248] In addition, an adhesive layer 2597 is provided in contact with the wiring 2594. 95 is attached to the display panel 2501 via an adhesive layer 2597 so as to overlap it. The surface of the display panel 2501 that is in contact with the adhesive layer 2597 is as shown in FIG. A substrate 2570 may be included, but is not required.

[0249] The adhesive layer 2597 is translucent. For example, a thermosetting resin or an ultraviolet curing resin may be used. Specifically, acrylic resin, urethane resin, epoxy resin, or white resin can be used. Xanthane-based resins can be used.

[0250] The display panel 2501 shown in FIG. 11A has a matrix between a substrate 2510 and a substrate 2570. The pixel has a plurality of pixels arranged in a square shape and a driving circuit. and a pixel circuit that drives the element.

[0251] FIG. 11A shows a pixel 2502R as an example of a pixel of the display panel 2501. A scanning line driver circuit 2503g is shown as an example of a driving circuit.

[0252] The pixel 2502R has a light emitting element 2550R and a power supply for the light emitting element 2550R. The transistor 2502t can be used.

[0253] The transistor 2502t is covered with an insulating layer 2521. Note that the insulating layer 2521 is It has the function of flattening unevenness caused by previously formed transistors, etc. The insulating layer 2521 may be given a function of suppressing the diffusion of impurities. This is preferable because it can prevent the reliability of transistors and the like from being reduced due to diffusion.

[0254] The light-emitting element 2550R is electrically connected to the transistor 2502t via a wiring. The light emitting element 2550R is directly connected to the wiring. The end of one electrode of terminal 2550R is covered with insulator 2528.

[0255] The light emitting element 2550R has an EL layer between a pair of electrodes. A colored layer 2567R is provided at a position overlapping with the light emitting element 2550R. The light passes through the colored layer 2567R and is emitted in the direction of the arrow shown in the figure. A light-shielding layer 2567BM is provided at the end of the light-emitting element 2550R and the colored layer 2567R. A sealing layer 2560 is provided between them.

[0256] In addition, when the sealing layer 2560 is provided in the direction in which light from the light emitting element 2550R is extracted, In this case, the sealing layer 2560 preferably has light-transmitting properties. It is preferable that the refractive index be higher than that of the glass.

[0257] The scanning line driver circuit 2503g includes a transistor 2503t and a capacitor 2503c. The driver circuit and the pixel circuit can be formed on the same substrate in the same process. Similarly to the transistor 2502t of the pixel circuit, the driver circuit (scanning line driver circuit 2503g The transistor 2503t in the second embodiment is also covered with an insulating layer 2521.

[0258] In addition, a wiring 2511 capable of supplying a signal to the transistor 2503t is provided. A terminal 2519 is provided in contact with the wiring 2511. It is electrically connected to FPC2509(1), which transmits image signals and It has the function of supplying signals such as a print signal and a synchronization signal. A printed wiring board (PWB) may be attached.

[0259] A bottom-gate transistor is applied to the display panel 2501 shown in FIG. However, the structure of the transistor is not limited to this and various structures are possible. In addition, a transistor having a structure similar to that of transistor 2 shown in FIG. The transistor 502t and the transistor 2503t have a semiconductor layer containing an oxide semiconductor as a channel region. In addition, it can be used as a semiconductor layer containing amorphous silicon, a laser, A semiconductor layer containing polycrystalline silicon crystallized by annealing or other processes is used as a channel region. It can be used as follows.

[0260] In addition, a top gate transistor, which is different from the bottom gate transistor shown in FIG. A structure in which a transistor of this type is applied to the display panel 2501 is shown in FIG. Even if the structure of the transistor is changed, it can be used for the channel region. The same applies to variations.

[0261] The touch panel 2000 shown in FIG. 11(A) is configured such that light from pixels is An anti-reflection layer 2567p is formed on the surface from which light is emitted to the outside so as to overlap at least the pixels. It is preferable that the anti-reflection layer 2567p has a circular polarizing plate or the like. Cut.

[0262] The substrate 2510, the substrate 2570, and the substrate 2590 shown in FIG. 11(A) are, for example, water. Vapor permeability is 1×10 -5 g / (m 2 ·day) or less, preferably 1 × 10 -6 g / ( m2 A material having a flexibility of not more than 100 sq. m can be preferably used. It is preferable to use materials whose thermal expansion coefficients are approximately the same for these substrates. is 1×10 -3 / K or less, preferably 5×10 -5 / K or less, more preferably 1×10 - 5 Examples of materials include those with a temperature of 1000 K or less.

[0263] Next, a touch panel 2000' having a different configuration from the touch panel 2000 shown in FIG. 12. However, as a touch panel similar to the touch panel 2000, can be applied.

[0264] FIG. 12 shows a cross-sectional view of the touch panel 2000′. The touch panel 200 shown in FIG. 0' is a touch sensor for the touch panel 2000 shown in FIG. 11 and the display panel 2501. The position of the 2595 is different. Here, we will only explain the different configurations, and The description of the touch panel 2000 will be used for the relevant parts.

[0265] The colored layer 2567R is located at a position overlapping the light emitting element 2550R. Light from the light emitting element 2550R is emitted in the direction in which the transistor 2502t is provided. That is, (a part of) the light from the light emitting element 2550R is transmitted through the colored layer 2567R. The light is then emitted in the direction of the arrow shown in the figure. 67BM is provided.

[0266] The touch sensor 2595 is a touch sensor that is connected to the light emitting element 2550R of the display panel 2501. It is provided on the side where the transistor 2502t is provided (see FIG. 12(A)).

[0267] The adhesive layer 2597 is in contact with the substrate 2510 of the display panel 2501. In the case of the structure shown in FIG. 2(A), the display panel 2501 and the touch sensor 2595 are bonded together. However, the display panel 2501 and the touch panel 2502 are bonded together by the adhesive layer 2597. The substrate 2510 may not be provided between the sensor 2595 and the substrate 2510 .

[0268] In addition, in the same manner as in the case of the touch panel 2000, the touch panel 2000' also has a display panel Transistors with various structures can be applied to 2501. In the above, a case where a bottom gate transistor is applied is shown. As shown in B), a top gate type transistor may be applied.

[0269] Next, an example of a method for driving a touch panel will be described with reference to FIG.

[0270] FIG. 13(A) is a block diagram showing the configuration of a mutual capacitance type touch sensor. In A), a pulse voltage output circuit 2601 and a current detection circuit 2602 are shown. In 13(A), the electrodes 2621 to which the pulse voltage is applied are designated as X1-X6, and the change in current is The electrodes 2622 for detecting the voltage are designated Y1-Y6, and are illustrated with six wires each. 13A shows a capacitance 2 formed by overlapping an electrode 2621 and an electrode 2622. 603. The electrodes 2621 and 2622 have functions interchangeable with each other. That's fine.

[0271] The pulse voltage output circuit 2601 is a circuit for applying pulse voltages to the X1-X6 wirings in order. When a pulse voltage is applied to the wiring of X1-X6, a capacitance 2603 is formed. An electric field is generated between the electrode 2621 and the electrode 2622. The electric field generated between the electrodes may cause shielding or the like. This generates a change in the mutual capacitance of the capacitor 2603, and the proximity of the object to be detected or can detect contact.

[0272] The current detection circuit 2602 detects the current flowing through the wiring Y1 to Y6 due to the change in mutual capacitance at the capacitor 2603. The Y1-Y6 wiring detects the proximity of the object to be detected, or the change in the current. The detected current value does not change if there is no contact or proximity of the object to be detected. When the mutual capacitance decreases due to contact, a decrease in the current value is detected. This can be done using an integrating circuit or the like.

[0273] Next, FIG. 13(B) shows the input / output of the mutual capacitance type touch sensor shown in FIG. 13(A). FIG. 13(B) shows the timing chart of the output waveform of each row and column in one frame period. In addition, in FIG. 13(B), when the object to be detected is not detected (non-detection), The two cases shown are when a touch is detected and when an object is detected. For the wires Y1-Y6, the waveforms are shown as voltage values ​​corresponding to the detected current values. do.

[0274] A pulse voltage is applied to the wires X1-X6 in order, and the wires Y1-Y The waveform on wire 6 changes. When there is no proximity or contact of the object to be detected, the waveform on wire X1-X6 The waveforms of Y1-Y6 change uniformly according to the change in the voltage of the wiring. At the point where the current decreases, the waveform of the voltage also changes. In this way, by detecting the change in mutual capacitance, the proximity or contact of the object to be detected can be detected. It is possible.

[0275] In addition, in FIG. 13(A), a panel in which only a capacitor 2603 is provided at the intersection of the wiring as a touch sensor is used. The configuration of a passive type touch sensor has been shown, but an active type with a transistor and a capacitor may also be used. The touch sensor shown in FIG. 14 is one of the sensors included in the active type touch sensor. 1 shows an example of a capacitor circuit.

[0276] The sensor circuit shown in FIG. 14 includes a capacitor 2603, a transistor 2611, and a transistor 2621. 612 and a transistor 2613.

[0277] A signal G2 is applied to the gate of the transistor 2613, and a voltage is applied to either the source or the drain. A voltage VRES is applied, and the other is connected to one electrode of the capacitor 2603 and the The transistor 2611 has a source and a drain electrically connected to the gate. It is electrically connected to either the source or the drain of the transistor 2612, and the other is connected to the voltage VSS. The transistor 2612 receives a signal G1 at its gate and a signal G2 at its source or drain. The other electrode of the capacitor 2603 is electrically connected to the wiring ML. is given.

[0278] Next, the operation of the sensor circuit shown in Figure 14 will be described. First, the signal G2 is When a potential that turns on the transistor 2613 is applied, the gate of the transistor 2611 A potential corresponding to the voltage VRES is applied to the connected node n. Next, as the signal G2 By applying a potential that turns off the transistor 2613, the potential of the node n is maintained. Next, the mutual capacitance of the capacitor 2603 changes when a finger or other object to be detected approaches or touches the capacitor. As the voltage at node n changes, the potential at node n changes from VRES.

[0279] In the read operation, a potential that turns on the transistor 2612 is applied as the signal G1. The current flowing through the transistor 2611 in response to the potential of the node n, that is, the current flowing through the wiring ML The current changes, and by detecting this current, the proximity or contact of the object to be detected can be detected. It is possible.

[0280] The transistors 2611, 2612, and 2613 are made of oxides. It is preferable to use a nitride semiconductor layer as the semiconductor layer in which the channel region is formed. By applying such a transistor to the transistor 2613, the potential of the node n can be kept low for a long time. This allows the voltage to be held for a certain period of time, and the operation of resupplying VRES to node n (lift This can reduce the frequency of reshuffling.

[0281] This embodiment may be appropriately combined with at least a part of another embodiment described in this specification. It can be implemented in combination. [Example]

[0282] <Synthesis Example 1> In this example, a heterocyclic compound, 2-[3-(benzo[1,2-b: 4,5-b']bisbenzofuran-6-yl)phenyl]dibenzo[f,h]quinoxalate The synthesis method of 2mBbfPDBq (structural formula (101)) will be explained. The structure of 2mBbfPDBq is shown below.

[0283] [ka]

[0284] <Synthesis of 2mBbfPDBq> <Step 1> In a 200 mL three-neck flask, add 8.9 g (30 mmol) of 1,4-dibromo-2,5- Dimethoxybenzene, 10 g (72 mmol) of 2-fluorophenylboronic acid, and 1 5 mL of toluene and 15 mL of diethylene glycol dimethyl ether (diglym e) and 60 mL of aqueous sodium carbonate solution (2.0 mol / L) were added, and the flask was decompressed. The mixture was degassed by stirring under pressure.

[0285] After degassing, the system was purged with a nitrogen stream, and the mixture was heated to 80°C. 0.69g (0.60mmol) tetrakis(triphenylphosphine)palladium(0 ) was added and stirred at the same temperature for 2 hours. The mixture was allowed to cool to room temperature and then degassed again under reduced pressure. After placing under a stream of air, the mixture was heated to 80°C. After heating, 0.69 g (0.60 mm ol) tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred at the same temperature for 5 hours. It was heated for a while.

[0286] After heating, 2.0 g (14 mmol) of 2-fluorophenylboronic acid was added, and the mixture was further heated at the same temperature. After heating, the mixture was allowed to cool to room temperature and then degassed under reduced pressure. The mixture was heated to 80°C and 0.64 g (0.55 mmol) of tetrakis(trimethylsilyl)propanol was added. (triphenylphosphine)palladium(0) and 3.0 g (21 mmol) of 2-fluoro Phenylboronic acid was added, and the mixture was stirred at the same temperature for 2 hours. After stirring, the mixture was allowed to cool to room temperature. The organic and aqueous layers were separated.

[0287] The resulting aqueous layer was extracted three times with toluene, and the extract and the organic layer were combined and washed with saturated brine. The mixture was washed with HCl and dried over anhydrous magnesium sulfate. The obtained filtrate was concentrated to obtain a compound. The obtained compound was recrystallized from toluene. The filtrate was concentrated and the compound obtained was purified by column chromatography. When purified using a developing solvent of hexane:ethyl acetate=30:1, 0.3% of the target compound was isolated. g, and a total of 2.8 g of the target product was obtained in a yield of 29%. is shown in the following formula (A-1).

[0288] [ka]

[0289] <Step 2> In a 300 mL three-neck flask, add 2.8 g (8.7 mmol) of 1,4-bis(2-fluoromethyl)propanol. (2,5-dimethoxyphenyl)benzene was added to the flask, and the flask was then purged with nitrogen. 20 mL of dehydrated dichloromethane was added to obtain a solution. This solution was placed in an ice bath and stirred. To the solution, add 21 mL (21 mmol) of boron tribromide solution (1 mol / L dichloromethane solution). ) diluted with 22 mL of dehydrated dichloromethane was added dropwise, and the resulting solution was heated at room temperature. The mixture was stirred for about 15 hours.

[0290] After stirring, the resulting solution was cooled in an ice bath, and 10 mL of water and 5 mL of methanol were added dropwise. After the dropwise addition, the precipitated solid was collected by suction filtration to obtain the target white solid. The filtrate was separated into an organic layer and an aqueous layer, and the resulting aqueous layer was extracted three times with dichloromethane. The extract and the organic layer were combined and washed with aqueous sodium bicarbonate and saturated saline. The mixture was subjected to gravity filtration, and the filtrate was concentrated. The synthesis scheme showing the above synthesis method is shown in the following formula (A- 2) is shown.

[0291] [ka]

[0292] <Step 3> In a 100 mL three-neck flask, add 2.3 g (7.8 mmol) of 1,4- Bis(2-fluorophenyl)-2,5-dihydroxybenzene and 4.2 g (30 mm ol) of potassium carbonate and 44 mL of N-methyl-2-pyrrolidinone were added to the flask. The mixture was degassed by stirring under reduced pressure. After degassing, the system was purged with nitrogen and then The mixture was stirred at 200°C for 4.5 hours. After stirring, it was allowed to cool to room temperature and then dissolved in toluene. Water and hydrochloric acid were added and the mixture was stirred, and the organic layer and the aqueous layer were separated.

[0293] The obtained aqueous layer was extracted three times with toluene. The obtained extract and the organic layer were combined to give The solid precipitated during the reaction, so it was collected by suction filtration. The filtrate was diluted with carbonated water. The mixture was washed with an aqueous sodium chloride solution and saturated brine, and then dried over anhydrous magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated to obtain a solid, which was then recrystallized with toluene. The solid precipitated earlier was recrystallized with toluene, yielding 0.53 g of the target solid. The total amount of the target solids was 1.5 g (5.7 mmol). The synthesis method described above was carried out in a yield of 73%. .

[0294] [ka]

[0295] <Step 4> In a 100 mL three-neck flask, add 1.4 g (5.5 mmol) of benzo[1,2-b:4, 5-b']bisbenzofuran was added, and the flask was purged with nitrogen. Water and tetrahydrofuran were added, and the resulting solution was stirred at −78° C. To this solution, 4.0 ml L of n-butyllithium hexane solution (1.6 mol / L, 6.3 mmol) was added dropwise. After the dropwise addition, the mixture was stirred at the same temperature for 20 minutes, then heated to room temperature and stirred for 1 hour. The resulting solution was then cooled to -78°C, and after cooling, 1.5 mL (13 mmol) of boric acid was added. Methyl methyl was added dropwise at the same temperature.

[0296] The resulting solution was warmed to room temperature and stirred at room temperature for 15 hours. After stirring, 50 mL of hydrochloric acid (1 mol / L) was added and the mixture was stirred for 1 hour. After stirring, the organic layer and the aqueous layer were separated. The aqueous layer was extracted twice with ethyl acetate. The resulting extract and the organic layer were combined and Wash with aqueous sodium bicarbonate solution and saturated saline, and then add anhydrous magnesium sulfate. The resulting mixture was gravity filtered, and the filtrate was concentrated to give a solid.

[0297] The obtained solid was washed with chloroform and filtered by suction to obtain 0.53 g of the target solid. The filtrate was concentrated to give a compound, which was recrystallized from toluene / hexane. 0.60 g of the target solid was obtained. The total amount of the target solid was 1.1 g (3.7 mmol). The synthesis method was carried out in a yield of 67%. The synthesis scheme showing the above synthesis method is shown in the following formula (A-4).

[0298] [ka]

[0299] <Step 5> In a 100 mL three-neck flask, add 1.2 g (3.1 mmol) of 2-(3-bromophenyl) ) dibenzo[f,h]quinoxaline and 1.1 g (3.6 mmol) of benzo[1,2- b: 4,5-b']bisbenzofuran-6-boronic acid and 50 mg (0.16 mmol) of tris(2-methylphenyl)phosphine, 15 mL of toluene, and 2 mL of ethanol. Add 5 mL of potassium carbonate solution (2.0 mol / L) and reduce the pressure inside the flask. The mixture was degassed while stirring.

[0300] After degassing, the flask was purged with a nitrogen stream and the mixture was heated to 80°C. Then, 10 mg (45 μmol) of palladium (II) acetate was added and stirred for 7 hours. After cooling to room temperature, the precipitated solid was collected by suction filtration. The solid was washed with ethanol to obtain the target solid. The resulting solution was filtered through Celite and alumina. The filtrate was concentrated to give The solid was recrystallized with toluene to obtain 1.0 g (1.8 mmol) of the target solid. ), was obtained in 58% yield.

[0301] The resulting 1.0 g of solid was purified by train sublimation. The purification was carried out by heating the solid at 335°C under a pressure of 2.6 Pa and a flow rate of 5 mL / min of argon. After sublimation purification, 0.61 g of the target pale yellow solid was obtained, with a recovery rate of 5. The synthesis scheme showing the above synthesis method is shown in the following formula (A-5).

[0302] [ka]

[0303] The pale yellow solid obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 15. In Example 1, the heterocyclic compound represented by the structural formula (101) is an embodiment of the present invention. It was found that 2mBbfPDBq was obtained.

[0304] 1 H NMR (tetrachloroethane-d2, 500 MHz): δ = 7.25 (t, J = 7 .5Hz, 1H), 7.48(t, J=7.5Hz, 1H), 7.52-7.59(m, 2H), 7.67(d, J=8.0Hz, 1H), 7.72(d, J=8.0Hz, 1H ), 7.77(t, J=7.0Hz, 2H), 7.82-7.89(m, 3H), 7.9 8(t, J=7.5Hz, 1H), 8.09(d, J=7.5Hz, 1H), 8.16( d, J=7.5Hz, 1H), 8.22(d, J=1.0Hz, 1H), 8.63(d, J=7.5Hz, 1H), 8.71(d, J=7.5Hz, 2H), 8.88(s, 1H) ), 9.34(d, J=8.0Hz, 1H), 9.43(d, J=8.0Hz, 1H), 9.57(s, 1H).

[0305] Next, the UV-visible absorption spectra of the toluene solution and solid thin film of 2mBbfPDBq (hereafter referred to as The solid thin film was made of quartz. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer ( A fluorometer (V550 manufactured by JASCO) was used to measure the emission spectrum. The absorption spectrum of the obtained toluene solution was The measurement results of the absorption spectrum and the emission spectrum are shown in Figure 16(A). The horizontal axis is the wavelength and the vertical axis is the absorption intensity. The absorption spectrum and emission spectrum of the solid thin film are shown in Fig. 16(B). ) where the horizontal axis represents wavelength and the vertical axis represents absorption intensity.

[0306] From the results of Figure 16(A), in the toluene solution of 2mBbfPDBq, An absorption peak is observed around 33 nm, and emission wavelength peaks are observed around 392 nm and 404 nm. In addition, from the results of Figure 16(B), in the solid thin film of 2mBbfPDBq, 2 Absorption peaks are observed around 63 nm and 337 nm, and an emission wavelength peak is observed around 429 nm. was seen. [Example]

[0307] <Synthesis Example 2> In this example, a heterocyclic compound, 2-[3-(benzo[1,2-b: 5,4-b']bisbenzofuran-6-yl)phenyl]dibenzo[f,h]quinoxalate This article explains the synthesis method of 2mBbf(II)PDBq (structural formula (107)). The structure of 2mBbf(II) PDBq is shown below.

[0308] [ka]

[0309] <Synthesis of 2mBbf(II)PDBq> <Step 1> In a 200 mL three-neck flask, add 5.0 g (36 mmol) of 1,3-dimethoxybenzene. After degassing, the system was placed under a nitrogen stream. Then, 80 mL of dehydrated dichloromethane was added and stirred. The resulting solution was cooled in an ice bath. Then, dissolve 12 g (75 mmol) of bromine in 14 mL of dehydrated dichloromethane in the same flask. The resulting solution was added dropwise.

[0310] After the dropwise addition, the resulting solution was stirred at room temperature for 15 hours. After stirring, the resulting solution was cooled in an ice bath. While doing so, add aqueous sodium bicarbonate solution and saturated aqueous sodium thiosulfate solution until the pH reaches 8. The resulting mixture was separated into an organic layer and an aqueous layer, and the aqueous layer was diluted with dichloromethane for 3 minutes. The resulting extract and the organic layer were combined and washed with saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the mixture was gravity filtered to obtain a filtrate. .

[0311] The filtrate was concentrated to obtain a solid, to which hexane was added and the mixture was subjected to ultrasonic irradiation. The solid was obtained by suction filtration. The obtained solid was recrystallized from hexane / ethyl acetate. The target solid was obtained in an amount of 7.2 g (24 mmol) with a yield of 67%. The synthesis scheme is shown in the following formula (B-1).

[0312] [ka]

[0313] <Step 2> In a 200 mL three-neck flask, 7.1 g (24 mmol) of 1,5-dibromo-2,4- Dimethoxybenzene, 2.8 g (20 mmol) of 2-fluorophenylboronic acid, 12 mL of toluene, 12 mL of diethylene glycol dimethyl ether, and 50 mL The flask was then depressurized while stirring. After degassing, the system was purged with nitrogen and the mixture was heated to 80°C. .

[0314] To this mixture, 0.55 g (0.48 mmol) of tetrakis(triphenylphosphine ) Palladium (0) was added and stirred at the same temperature for 3 hours. After the mixture was allowed to cool to room temperature, 4.5 g (32 mmol) of 2-fluorophenylboronic acid and 0.12 g (0.29 mmol) of Add 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl and then reduce the pressure The system was degassed, and the inside of the system was again placed under a nitrogen stream and heated to 80°C. 3 mmol) of palladium(II) acetate was added, and the mixture was stirred at the same temperature for 4 hours.

[0315] After stirring, the mixture was allowed to cool to room temperature and separated into an organic layer and an aqueous layer. The extract and the organic layer were combined, washed with saturated saline, and then washed with HCl. The mixture was dried over magnesium, and the filtrate was concentrated to give a brown oil. This oil was purified by silica gel column chromatography (eluent: hexane, The target pale yellow oil was purified by elution with a gradient of 1000kJ / 2000kcal from chloroform to 1000kcal. The synthesis method described above was shown in the following synthesis scheme. This is shown in formula (B-2).

[0316] [ka]

[0317] <Step 3> In a 500 mL three-neck flask, add 7.2 g (22 mmol) of 1,5-bis(2-fluoromethylpropional) (phenyl)-2,4-dimethoxybenzene was added, and the flask was purged with nitrogen. 60 mL of dehydrated dichloromethane was added to obtain a solution, which was then placed in an ice bath and stirred. To this solution, add 53 mL (53 mm) of boron tribromide solution (1 mol / L dichloromethane solution). ol) diluted with 50 mL of dehydrated dichloromethane was added dropwise, and the resulting solution was After stirring, the mixture was cooled in an ice bath again and 40 mL of methanol and 4 0 mL of water was added dropwise, and the organic and aqueous layers of the resulting mixture were separated. Extraction was performed three times with chloromethane, and the resulting extract and organic layer were combined and diluted with sodium bicarbonate. After washing with aqueous solution and saturated saline, it was dried over anhydrous magnesium sulfate. The resulting mixture was gravity filtered, and the filtrate was concentrated to obtain about 7 g of the target pale yellow oil. The synthesis scheme showing the above synthesis method is shown in the following formula (B-3).

[0318] [ka]

[0319] <Step 4> In a 300 mL three-neck flask, add approximately 7 g (approximately 22 mmol) of 1,5-dichloro-2,5-diol obtained in Step 3. -bis(2-fluorophenyl)-2,4-dihydroxybenzene, 13 g (96 mm 100 ml of potassium carbonate and 140 mL of N-methyl-2-pyrrolidinone in a flask. The mixture was degassed by stirring while the pressure inside was reduced. After degassing, the system was purged with nitrogen and then The mixture was stirred at 200° C. for 7 hours.

[0320] After stirring, the mixture was allowed to cool to room temperature, and then toluene, water, and hydrochloric acid were added and stirred. The aqueous layer was separated and the aqueous layer was extracted three times with toluene. The mixture was washed with aqueous sodium bicarbonate and saturated saline, and then with anhydrous magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to give a yellow oil. The oily substance obtained was recrystallized from toluene / hexane to give the target white powder. A crystalline solid was obtained.

[0321] The resulting solid was recrystallized from toluene / hexane to obtain the target solid. The filtrate was concentrated to obtain an oily substance, which was then purified by silica gel column chromatography (eluent: hexane). The product was purified using a solvent (solvent) and recrystallized from hexane to obtain the desired white powdery solid. The resulting white powdery solid was 2.2 g (8.5 mmol) in total, and the two The synthesis method was obtained in a yield of 39% in this step. vinegar.

[0322] [ka]

[0323] <Step 5> In a 200 mL three-neck flask, add 2.2 g (8.5 mmol) of benzo[1,2-b:5, 4-b']bisbenzofuran was added to the flask, and the inside of the flask was vacuumed while stirring. After degassing, the system was placed under a nitrogen stream, and 40 mL of dehydrated tetrahydrofuran was added. The resulting solution was stirred at -78°C.

[0324] After stirring, 5.6 mL of n-butyllithium hexane solution (1.60 mol / L, 9.0 m After the addition, the mixture was warmed to room temperature and stirred for 30 minutes. The resulting solution was cooled to -78°C, and 2.20 g (8.7 mmol) of iodine was added to 10 mL of dehydrated A solution of the mixture in tetrahydrofuran was added dropwise at the same temperature. The temperature was then raised and the mixture was stirred at the same temperature for about 15 hours.

[0325] After stirring, water was added to the resulting solution and stirred, and the resulting mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was extracted three times with toluene, and the obtained extract and the organic layer were combined and diluted with carbonated water. The mixture was washed with an aqueous sodium chloride solution, an aqueous sodium thiosulfate solution, and then with saturated saline. The mixture was dried by adding magnesium sulfate, and the filtrate was concentrated. The solid obtained was recrystallized from toluene / hexane to give the target pale brown solid. The synthesis method described above was shown in the following synthesis scheme. This is shown in formula (B-5).

[0326] [ka]

[0327] <Step 6> In a 200 mL three-neck flask, add 1.5 g (3.8 mmol) of 6-iodo-benzo[1, 2-b:5,4-b']bisbenzofuran and 1.8 g (4.2 mmol) of 2-[3- (2-dibenzo[f,h]quinoxalinyl)phenyl]-4,4,5,5-tetramethyl -1,3,2-dioxaborolane and 70 mg (0.23 mmol) of tris(2-methyl (phenyl)phosphine, 20 mL of toluene, 2 mL of ethanol, and 6 mL of charcoal. Add an aqueous solution of potassium carbonate (2.0 mol / L) and stir while reducing the pressure inside the flask. The mixture was degassed.

[0328] After degassing, the system was purged with a nitrogen stream and the mixture was heated to 80°C. 45 μmol) of palladium(II) acetate was added, and the mixture was stirred at the same temperature for 2.5 hours. After stirring, the mixture was allowed to cool to room temperature, and then 10 mg (45 μmol) of palladium acetate ( II) was added and stirred for 8 hours. After cooling to room temperature, the mixture was concentrated and 20 mL of Ethylene glycol dimethyl ether and 6 mL of aqueous sodium carbonate (2.0 mol 1 / L) was added, and the mixture was stirred while reducing the pressure inside the flask to degas the mixture.

[0329] After degassing, the system was purged with a nitrogen stream and heated to 80°C. mol) tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred for 1.5 hours. After stirring, the resulting mixture was allowed to cool to room temperature, and the precipitated solid was collected by suction filtration. The solid obtained was washed with water and ethanol. The solid obtained was dissolved in toluene. The resulting filtrate was concentrated and the resulting solid was collected by filtration through Celite and alumina. The target product was recrystallized from toluene to give 1.2 g (2.1 mmol) of a pale yellow solid. The rate was 55%.

[0330] The obtained solid was purified by sublimation using a train sublimation method. The solid was heated at 310°C for 15.5 hours under 2.5 Pa and argon at a flow rate of 5 mL / min. The target pale yellow solid was obtained in an amount of 0.90 g with a recovery rate of 75%. The synthesis scheme showing the above synthesis method is shown in the following formula (B-6).

[0331] [ka]

[0332] The pale yellow solid obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 17. In Example 2, the heterocyclic compound represented by the structural formula (107) is an embodiment of the present invention. It was found that 2mBbf(II) PDBq was obtained.

[0333] 1 H NMR (tetrachloroethane-d2, 500 MHz): δ = 7.49 (t, J = 8 .0Hz, 2H), 7.56(t, J=8.0Hz, 2H), 7.74(d, J=8.0 Hz, 2H), 7.81-7.89(m, 4H), 7.93(t, J=8.0Hz, 1H ), 8.18(d, J=7.5Hz, 2H) 8.43(d, J=6.5Hz, 1H), 8 .53(d, J=8.0Hz, 1H), 8.56(s, 1H), 8.71(d, J=8. 0Hz, 2H), 9.27(s, 1H), 9.34(d, J=7.5Hz, 1H), 9. 56(d, J=8.0Hz, 1H), 9.60(s, 1H).

[0334] Next, the UV-visible absorption spectra of 2mBbf(II)PDBq in toluene and in solid thin films were analyzed. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. The absorbance spectrum was measured using ultraviolet-visible spectrophotometer. A fluorescence spectrometer (V550 model, manufactured by JASCO Corporation) was used to measure the emission spectrum. A spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used. The measurement results of the spectrum and the emission spectrum are shown in Figure 18(A). The horizontal axis is the wavelength, and the vertical axis is The absorption intensity is shown. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are also shown. 18(B). The horizontal axis represents wavelength and the vertical axis represents absorption intensity.

[0335] From the results of Figure 18(A), in the toluene solution of 2mBbf(II)PDBq, Absorption peaks are observed around 288 nm and 393 nm, and emission peaks are observed around 404 nm. In addition, the results of Figure 18(B) show that the peak of 2mBbf(II)PDBq In the solid thin film, absorption peaks are observed around 265 nm and 384 nm, and around 430 nm. A peak in the emission wavelength was observed. [Example]

[0336] <Synthesis Example 3> In this example, a heterocyclic compound, 2-[3-(benzo[1,2-b: 5,6-b']bisbenzofuran-4-yl)phenyl]dibenzo[f,h]quinoxalate This paper describes the synthesis of 2mBbf(III)PDBq (Structural formula (149)). The structure of 2mBbf(III) PDBq is shown below.

[0337] [ka]

[0338] <Synthesis of 2mBbf(III)PDBq> <Step 1> In a 500 mL three-neck flask, add 10 g (46 mmol) of 2-bromo-1,3-dimethoxamine. benzene, 7.2 g (51 mmol) of 2-fluorophenylboronic acid, and 66 mL of toluene and 66 mL of diethylene glycol dimethyl ether (diglyme) Add 76 mL of aqueous sodium carbonate solution (2.0 mol / L) and reduce the pressure inside the flask. After degassing, the system was purged with nitrogen and the mixture was then stirred for 8 hours. The mixture was heated to 0°C. At the same temperature, 1.1 g (0.95 mmol) of tetrakis( Tris(methylphenylphosphine)palladium(0) was added, and the mixture was stirred for 5 hours.

[0339] After stirring, the resulting mixture was allowed to cool to room temperature, and then 3.2 g (23 mmol) of 2-fluoropropanediol was added. phenylboronic acid and 1.0 g (0.87 mmol) of tetrakis(trismethylphenyl) Phosphine)palladium(0) was added, and the mixture was stirred while reducing the pressure inside the flask. After degassing and placing the system under a nitrogen stream, the mixture was stirred at 80°C for 8 hours. After cooling to room temperature, 5.2 g (37 mmol) of 2-fluorophenylboronic acid and 0.1 9g (0.46mmol) 2-dicyclohexylphosphino-2',6'-dimethoxy Add biphenyl and 50 mg (0.22 mmol) of palladium (II) acetate to the flask. The mixture was degassed by stirring while reducing the pressure inside the container. The mixture was stirred at 80° C. for 4 hours.

[0340] After stirring, the mixture was allowed to cool to room temperature and separated into an organic layer and an aqueous layer. The extract and the organic layer were combined and washed with saturated brine. The mixture was dried over magnesium sulfate, and the filtrate was concentrated. A dark brown oily substance was obtained. The oily substance was subjected to silica gel column chromatography (development The solvent was purified using a gradient from hexane to chloroform, and then toluene When recrystallized from hexane, 8.4 g (36 mmol) of the target solid was obtained. The synthesis method was obtained at a yield of 78%. The synthesis scheme showing the above synthesis method is shown in formula (C-1) below.

[0341] [ka]

[0342] <Step 2> In a 300 mL Erlenmeyer flask, add 8.4 g (36 mmol) of 2'-fluoro- 1,3-Dimethoxy-2,1'-biphenyl and 130 mL of acetonitrile were added. To the resulting solution, 6.4 g (36 mmol) of N-bromosuccinimide was added, and the resulting The solution was stirred at room temperature for 23.5 hours. After stirring, water and dichloromethane were added to the resulting solution. The organic and aqueous layers of this mixture were separated.

[0343] The aqueous layer was extracted three times with dichloromethane, and the resulting extracts were combined with the organic layer and saturated thiol. Wash with aqueous sodium sulfate and saturated brine, then dry with anhydrous magnesium sulfate. The resulting mixture was gravity filtered, and the filtrate was concentrated to obtain a yellow oil, which was the target product. The compound was obtained in an amount of 11 g (35 mmol) with a yield of 97%. The synthesis scheme showing the above synthesis method is shown below. This is shown in formula (C-2).

[0344] [ka]

[0345] <Step 3> In a 300 mL three-neck flask, add 11 g (35 mmol) of 4-bromo-2'-fluoro- Add 1,3-dimethoxy-2,1'-biphenyl, place the system under a nitrogen stream, and then proceed as follows: 51 g (37 mmol) of 3-chloro-2-fluoro-benzeneboronic acid and 55 mL of Aqueous sodium carbonate solution (2.0 mol / L), 50 mL of toluene, and 50 mL of ethyl acetate were added. Dimethyl ether and 0.16 g (0.39 mmol) of 2-dicyclohexane The xylphosphino-2',6'-dimethoxybiphenyl was added. After degassing, the system was purged with nitrogen and heated to 80°C. Then, 40 mg (0.18 mmol) of palladium (II) acetate was added and the mixture was heated at the same temperature. The mixture was stirred at 40°C for 2 hours.

[0346] After stirring, the resulting mixture was allowed to cool to room temperature, and then 3.4 g (19 mmol) of 3-chloro -2-fluoro-benzeneboronic acid was added and heated to 80° C. To this mixture, 40 ml g (0.18 mmol) of palladium(II) acetate was added, and the mixture was stirred at the same temperature for 3 hours. After stirring, 0.90 g (5.2 mmol) of 3-chloro-2-fluoro-benzeneboronic acid Add 40 mg (0.18 mmol) of palladium (II) acetate and heat to 80°C. The mixture was stirred for 7 hours, and then allowed to cool to room temperature, after which the organic layer and the aqueous layer were separated. The aqueous layer was extracted three times with toluene, and the resulting extract and the organic layer were combined and washed with saturated brine. The filtrate obtained by gravity filtration was concentrated. An oily substance was obtained.

[0347] The oily substance obtained was purified by silica gel column chromatography (eluent: hexane / ethyl acetate). The product was purified by toluene / hexane (10:1) and recrystallized from toluene / hexane. The mother liquor from the recrystallization was concentrated to give a solid, which was then purified by high performance liquid chromatography (developing solvent). The solvent was chloroform, and the product was recrystallized from toluene / hexane. The target solid was obtained. The total amount of the target solid was 9.9 g (28 mmol), with a yield of 80%. The synthesis scheme showing the above synthesis method is shown in the following formula (C-3).

[0348] [ka]

[0349] <Step 4> In a 500 mL three-neck flask, add 9.8 g (27 mmol) of 4-(3-chloro-2-fluoro- (2-fluorophenyl)-2-(2-fluorophenyl)-1,3-dimethoxybenzene was added, The flask was purged with nitrogen and 150 mL of dehydrated dichloromethane was added. The solution was stirred in an ice bath and 70 ml of boron tribromide (1 mol / L dichloromethane solution) was added. A solution of L (70 mmol) diluted with 90 mL of dehydrated dichloromethane was added dropwise. The resulting solution was then stirred at room temperature for 15 hours. After stirring, the resulting solution was cooled in an ice bath. Then, 20 mL of methanol was added dropwise, and then 40 mL of water was added dropwise. The organic layer and the aqueous layer were separated. The resulting aqueous layer was extracted three times with dichloromethane. The organic layers were combined, washed with aqueous sodium bicarbonate and saturated brine, and then extracted with anhydrous magnesium sulfate. The mixture was dried over sodium hydroxide, and the filtrate was concentrated. The resulting oil was purified by silica gel column chromatography (development). The solvent was hexane:ethyl acetate (8:1), and then recrystallized with hexane / chloroform. Upon crystallization, 8.7 g (26 mmol) of a white solid was obtained as the target substance in a yield of 96%. The synthesis scheme showing the synthesis method is shown in the following formula (C-4).

[0350] [ka]

[0351] <Step 5> In a 500 mL recovery flask, add 8.7 g (26 mmol) of 4-(3-chloro-2-fluoro- (2-fluorophenyl)-2-(2-fluorophenyl)-1,3-dihydroxybenzene and 14 g (0.10 mmol) of potassium carbonate and 150 mL of N-methyl-2-pyrrolidinone The mixture was stirred while the pressure in the flask was reduced, and the mixture was degassed. After degassing, the system was filled with nitrogen. After being placed under an air stream, the mixture was stirred at 200°C for 9 hours. After stirring, the mixture was allowed to cool to room temperature. Thereafter, toluene, water and hydrochloric acid were added and stirred, and the resulting mixture was separated into an organic layer and an aqueous layer.

[0352] The resulting aqueous layer was extracted three times with toluene, and the resulting extract and organic layer were combined and diluted with carbonate. Wash with aqueous sodium hydrogen carbonate and saturated saline, then dry with anhydrous magnesium sulfate. This mixture was gravity filtered and the filtrate was concentrated to give a brown solid. The solid was recrystallized from toluene / hexane, and the first crystal was 3.4 g (12 mmol) ), and the second crystal 1.6g (5.4mmol), the yield of the first and second crystals combined was 67%. The synthesis scheme showing the above synthesis method is shown in the following formula (C-5).

[0353] [ka]

[0354] <Step 6> In a 100 mL three-neck flask, add 1.5 g (5.2 mmol) of 4-chlorobenzo[1,2 -b;5,6-b']bisbenzofuran and 2.5 g (5.7 mmol) of 2-[3-( 2-Dibenzo[f,h]quinoxalinyl)phenyl]-4,4,5,5-tetramethyl- 1,3,2-Dioxaborolane and 80 mg (0.22 mmol) of di(1-adamantine) (n-butyl)phosphine, 1.5 mL (16 mmol) of t-butanol, and 3 0.6g (17mmol) of potassium phosphate(III) and 26mL of diethylene glycol Add dimethyl ether (diglyme) and stir while reducing the pressure inside the flask. The mixture was degassed. After degassing, the system was purged with a nitrogen stream and the mixture was heated to 80°C.

[0355] To this mixture, 10 mg (45 μmol) of palladium(II) acetate was added and the mixture was heated at the same temperature for 4 After stirring, the mixture was allowed to cool to room temperature, and then 10 mg (45 μmol) of palladium acetate was added. The mixture was stirred at 100°C for 7 hours and then allowed to cool to room temperature. Then, 20 mg (89 μmol) of palladium (II) acetate was added, and the mixture was heated at 120°C for 4.5 hours. After stirring, the mixture was allowed to cool to room temperature, and the precipitate was collected by suction filtration.

[0356] The obtained solid was washed with water and ethanol. The obtained solid was dissolved in toluene by heating. The resulting solution was filtered through Celite and alumina. The filtrate was concentrated to give a solid. The solid was recrystallized from toluene to obtain 1.4 g (2.4 mmol) of the target solid. The yield was 46%.

[0357] The obtained solid was purified by sublimation using a train sublimation method. The solid was heated at 305°C for 20 hours under a pressure of 2.8 Pa and an argon flow rate of 10 mL / min. After purification by sublimation, 1.1 g of the target pale yellow solid was obtained with a recovery rate of 77%. The synthesis scheme showing the above synthesis method is shown in the following formula (C-6).

[0358] [ka]

[0359] The pale yellow solid obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 19. In Example 3, the heterocyclic compound represented by the structural formula (149) is an embodiment of the present invention. It was found that 2mBbf(III) PDBq was obtained.

[0360] 1 H NMR (tetrachloroethane-d2, 500 MHz): δ = 7.29 (t, J = 7 .5Hz, 1H), 7.50(t, J=7.5Hz, 1H), 7.62-7.73(m, 4H), 7.80-7.89(m, 4H), 7.92(t, J=7.5Hz, 1H), 8 .12(d, J=7.5Hz, 1H), 8.15(d, J=8.5Hz, 1H), 8.2 9(d, J=7.5Hz, 2H), 8.54(d, J=8.0Hz, 1H), 8.70( t, J=8.0Hz, 2H), 9.15(s, 1H), 9.36(d, J=7.5Hz, 1H), 9.48(d, J=7.5Hz, 1H), 9.65(s, 1H).

[0361] Next, the UV-visible absorption spectra of 2mBbf(III)PDBq in toluene solution and in solid thin film were analyzed. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. The film was prepared on a quartz substrate by vacuum deposition. A fluorescent spectrometer (V550 model, manufactured by JASCO Corporation) was used to measure the emission spectrum. A spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used. The measurement results of absorption spectrum and emission spectrum are shown in Figure 20(A). The horizontal axis is wavelength, and the vertical axis is represents the absorption intensity. The measurement results of the absorption spectrum and emission spectrum of the solid thin film are shown below. This is shown in Figure 20(B). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity.

[0362] From the results of Figure 20(A), in the toluene solution of 2mBbf(III)PDBq, 281n Absorption peaks are observed around 376 nm and 394 nm, and emission peaks are observed around 407 nm and 394 nm. The wavelength peak was observed. Also, from the results of Figure 20(B), 2mBbf(III) PDB In the solid thin film of q, absorption peaks are observed around 266 nm and 384 nm, and A peak in the emission wavelength was observed near the [Example]

[0363] <Synthesis Example 4> In this example, a heterocyclic compound, 2-[3′-(benzo[1,2-b :5,6-b']bisbenzofuran-4-yl)-1,1'-biphenyl-3-yl]di Benzo[f,h]quinoxaline (abbreviation: 2mBbf(III)BPDBq) (structural formula (1 50)) will be explained. The structure of 2mBbf(III)BPDBq is As shown below.

[0364] [ka]

[0365] <Synthesis of 2mBbf(III)BPDBq> <Step 1> In a 200 mL three-neck flask, add 1.5 g (2.8 mmol) of 4-chlorobenzo[1,2 -b;5,6-b']bisbenzofuran and 1.4 g (3.2 mmol) of 2-[3'- (2-dibenzo[f,h]quinoxalinyl)-1,1'-biphenyl-3-yl]-4, 4,5,5-tetramethyl-1,3,2-dioxaborolane and 60 mg (0.17 mm ol) di(1-adamantyl)(n-butyl)phosphine and 1 mL of t-butanol 1.7 g (8.2 mmol) of potassium phosphate(III) and 15 mL of diethylene Add glycol dimethyl ether (diglyme) and stir while reducing the pressure inside the flask. The mixture was then degassed.

[0366] After degassing, the system was purged with a nitrogen stream and the mixture was heated to 80°C. 10 mg (45 μmol) of palladium (II) acetate was added to the solution, and the mixture was stirred at the same temperature for 6 hours. After stirring, the resulting mixture was allowed to cool to room temperature, and then 10 mg (45 μmol) of paraacetic acid was added. After adding sodium(II), the mixture was stirred at 120°C for 4.5 hours, and then at 140°C for 3 hours. After stirring, the mixture was allowed to cool to room temperature, and the precipitated solid was collected by suction filtration. After washing with water and ethanol, 1.6 g (2.4 mmO l) was obtained in 86% yield.

[0367] The obtained solid (1.49 g) was purified by train sublimation. The solid was heated at 350°C under a pressure of 5.1 Pa and argon at a flow rate of 15 mL / min. After sublimation purification, 1.1 g of the target pale yellow solid was obtained, with a recovery rate of 76%. The synthesis scheme showing the above synthesis method is shown in the following formula (D-1).

[0368] [ka]

[0369] The pale yellow solid obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 21. In Example 4, the heterocyclic compound represented by the structural formula (150) is an embodiment of the present invention. It was found that 2mBbf(III)BPDBq was obtained.

[0370] 1 H NMR (tetrachloroethane-d2, 500 MHz): δ = 7.20 (t, J = 7 .5Hz, 1H), 7.31(t, J=7.5Hz, 1H), 7.50(d, J=7.5 Hz, 1H), 7.58(t, J=7.5Hz, 2H), 7.65(d, J=7.5Hz , 1H), 7.75-7.84(m, 6H), 7.93(d, J=7.5Hz, 1H), 8.03(d, J=7.5Hz, 1H), 8.07(d, J=7.5Hz, 1H), 8. 12(t, J=7.5Hz, 2H), 8.20(d, J=7.5Hz, 1H), 8.38 (d, J=7.5Hz, 1H), 8.62-8.66(m, 3H), 8.82(s, 1H) ), 9.27(d, J=7.5Hz, 1H), 9.32(d, J=7.5Hz, 1H), 9.49(s, 1H).

[0371] Next, the UV-visible absorption spectra of 2mBbf(III)BPDBq in toluene solution and in solid thin films were analyzed. The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. The thin film was prepared on a quartz substrate by vacuum deposition. A spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used. The measurement results of the absorption spectrum and the emission spectrum are shown in Figure 22(A). The horizontal axis is the wavelength, and the vertical axis is the The axis represents the absorption intensity. Also, the measurement results of the absorption spectrum and emission spectrum of the solid thin film. This is shown in Figure 22(B). The horizontal axis represents wavelength and the vertical axis represents absorption intensity.

[0372] From the results of Figure 22(A), in the toluene solution of 2mBbf(III)BPDBq, 264 Absorption peaks are observed around 385 nm and 391 nm, and around 407 nm. The peak of the light wavelength was observed. Also, from the results of Figure 22(B), 2mBbf(III)BP In the solid thin film of DBq, absorption peaks are observed around 264 nm and 385 nm, and A peak in the emission wavelength was observed around m. [Example]

[0373] In this example, a heterocyclic compound, 2mBbfPDBq (structural formula (10)), which is one embodiment of the present invention, was synthesized. 1)) using light-emitting device 1, 2mBbf(II)PDBq (structural formula (107)) Light-emitting element 2, light-emitting element 3 using 2mBbf(III)PDBq (structural formula (149)), Light-emitting device 4 was fabricated using 2mBbf(III)BPDBq (structural formula (150)). Furthermore, for comparison, 2mDBTBPDBq- A comparative light-emitting element 5 was fabricated using II. The fabrication of the optical element 5 will be described with reference to FIG. The academic formula is shown below.

[0374] [ka]

[0375] [ka]

[0376] <Fabrication of Light-Emitting Elements 1 to 4 and Comparative Light-Emitting Element 5> First, indium tin oxide (ITO) containing silicon oxide is sputtered onto a glass substrate 900. The first electrode 901, which functions as an anode, was formed by deposition using a deposition method. The film thickness was 110 nm, and the electrode area was 2 mm x 2 mm.

[0377] Next, as a pretreatment for forming the light emitting element 1 on the substrate 900, the surface of the substrate was washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0378] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 900 was It was left to cool for about minutes.

[0379] Next, the substrate 900 is placed in a vacuum deposition apparatus so that the surface on which the first electrode 901 is formed faces downward. In this example, the EL layer 902 was formed by vacuum deposition. The hole injection layer 911, the hole transport layer 912, the light emitting layer 913, the electron transport layer 914, and the electron The case where the injection layer 915 is formed sequentially will be described.

[0380] 10 in the vacuum chamber -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4- DBT3P-II: Molybdenum oxide was co-evaporated to a ratio of 4:2 (by mass), and hole injection was performed on the first electrode 901. The co-evaporation method is a method of depositing a layer 911 by co-evaporation using a plurality of different materials. This is a deposition method in which different evaporation sources are used simultaneously.

[0381] Next, 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) was evaporated to a thickness of 20 nm to form a hole transport layer 912 .

[0382] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0383] In the case of light-emitting element 1, 2-[3-(benzo[1,2-b:4,5-b']bisbenzofura (6-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 2mBbfPDBq ), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl) (phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine ( Abbreviation: PCBBiF), [Ir(tBuppm)2(acac)], 2mBbfPDB q:PCBBiF:[Ir(tBuppm)2(acac)]=0.7:0.3:0.0 The mixture was co-deposited so that the mass ratio was 5.5. The film thickness was 20 nm. 2mBbfPDBq:PCBBiF:[Ir(tBuppm)2(acac)]=0.8 : 0.2: 0.05 (mass ratio) and a film thickness of 20 nm was formed. A light emitting layer 913 having a laminated structure was formed to a thickness of 40 nm.

[0384] In the case of light-emitting element 2, 2-[3-(benzo[1,2-b:5,4-b']bisbenzofura (6-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 2mBbf(II) PDBq), PCBBiF, [Ir(tBuppm)2(acac)], 2mBbf( II)PDBq:PCBBiF:[Ir(tBuppm)2(acac)]=0.7:0 The film was co-evaporated to a thickness of 20 nm, and then 2 mB bf(II)PDBq:PCBBiF:[Ir(tBuppm)2(acac)]=0. The material was co-evaporated in a ratio of 8:0.2:0.05 (mass ratio) to form a film with a thickness of 20 nm. A light emitting layer 913 having a laminated structure was formed to a thickness of 40 nm.

[0385] In the case of light-emitting element 3, 2-[3-(benzo[1,2-b:5,6-b']bisbenzofura 2mBbf(III) )PDBq), PCBBiF, [Ir(tBuppm)2(acac)], 2mBbf (III)PDBq:PCBBiF:[Ir(tBuppm)2(acac)]=0.7 : 0.3: 0.05 (mass ratio) to form a 20 nm thick film. mBbf(III)PDBq:PCBBiF:[Ir(tBuppm)2(acac)] = 0.8:0.2:0.05 (mass ratio) and form a film with a thickness of 20 nm. As a result, a light emitting layer 913 having a laminated structure was formed with a film thickness of 40 nm.

[0386] In the case of light-emitting element 4, 2-[3'-(benzo[1,2-b:5,6-b']bisbenzofuran (1,1'-biphenyl-3-yl)dibenzo[f,h]quinoxaline (Abbreviation: 2mBbf(III)BPDBq), PCBBiF, [Ir(tBuppm)2 (acac)], 2mBbf(III)BPDBq:PCBBiF:[Ir(tBup pm)2(acac)] = 0.7:0.3:0.05 (mass ratio), After forming a 20 nm thick film, 2mBbf(III)BPDBq:PCBBiF:[Ir (tBuppm)2(acac)] = 0.8:0.2:0.05 (mass ratio) The light emitting layer 913 having a laminated structure is formed by vapor deposition to a thickness of 20 nm. The film was formed to a thickness of .

[0387] In the case of the comparative light-emitting element 5, 2-[3′-(dibenzothiophen-4-yl)biphenyl- 3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), P CBBiF, [Ir(tBuppm)2(acac)], 2mDBTBPDBq-II :PCBBiF:[Ir(tBuppm)2(acac)]=0.7:0.3:0.05 (mass ratio) to form a 20 nm thick film. -II:PCBBiF:[Ir(tBuppm)2(acac)]=0.8:0.2:0 The layer structure was formed by co-evaporating the material to a thickness of 20 nm so that the mass ratio was 0.05. The light-emitting layer 913 was formed to a thickness of 40 nm.

[0388] Next, in the case of the light-emitting element 1, 2mBbfPDBq was deposited to a thickness of 20 nm on the light-emitting layer 913. In the case of light-emitting element 2, 2mBbf(II)PDBq was deposited on the substrate. After evaporating 10 nm of Bphen, 2 mBbf (III ) After depositing 20 nm of PDBq, 10 nm of Bphen was deposited. After 20 nm of mBbf(III)BPDBq was deposited, 10 nm of Bphen was deposited. An electron transport layer 914 was formed on each of the layers.

[0389] Furthermore, lithium fluoride was vapor-deposited to a thickness of 1 nm on the electron transport layer 914 of each of the light-emitting elements 1 to 4. Thus, an electron injection layer 915 was formed.

[0390] Finally, aluminum was evaporated onto the electron injection layer 915 to a thickness of 200 nm, and a shaded A second electrode 903 serving as a polarity electrode was formed, and Light-emitting Elements 1 to 4 were obtained. In the deposition process, the deposition was all carried out using a resistance heating method.

[0391] The element structures of the thus obtained light-emitting elements 1 to 4 and the comparative light-emitting element 5 are shown in Table 1. show.

[0392] [Table 1]

[0393] The fabricated light-emitting elements 1 to 4 and the comparative light-emitting element 5 were also exposed to the air. The device was sealed in a glove box with a nitrogen atmosphere (a sealant was applied around the device). , UV treatment during sealing, and heat treatment at 80°C for 1 hour).

[0394] <Operation Characteristics of Light-Emitting Elements 1 to 4 and Comparative Light-Emitting Element 5> The operation characteristics of the fabricated light-emitting elements 1 to 4 were measured. The experiment was carried out in an atmosphere maintained at 5°C.

[0395] FIG. 24 shows the current density-luminance characteristics of the light-emitting elements 1 to 4, and FIG. 25 shows the voltage-luminance characteristics of the light-emitting elements 1 to 4. The power-current efficiency characteristics are shown in FIG. 26, and the voltage-current characteristics are shown in FIG.

[0396] Also, 1000cd / m 2 Light-emitting element 1, light-emitting element 2, light-emitting element 3, and light-emitting element The main initial characteristics of the light-emitting element 4 and the comparative light-emitting element 5 are shown in Table 2 below. , and good initial characteristics comparable to those of the light-emitting elements 1 to 4 were confirmed.

[0397] [Table 2]

[0398] Furthermore, 25 mA / cm 2 Light emission when current is passed at a current density of The emission spectra of the light-emitting elements 1 to 4 are shown in FIG. 28. The spectrum has a peak at around 546 nm, and the organometallic complexes used in the EL layer of each light-emitting device It is suggested that this is due to the green emission of the complex [Ir(tBuppm)2(acac)]. As with the light-emitting elements 1 to 4, the comparative light-emitting element 5 also exhibited [Ir(tBu The emission spectrum originating from the green emission of [(ppm)2(acac)] was confirmed.

[0399] Next, reliability tests were performed on the light-emitting elements 1 to 4. The results of the reliability tests are shown in FIG. In FIG. 29, the vertical axis indicates normalized luminance (%) when the initial luminance is 100%. The horizontal axis indicates the device operating time (h). / m 2 The light-emitting elements 1 to 4 were driven under the condition of a constant current density.

[0400] Note that each of the light-emitting elements 1 to 4 uses a heterocyclic compound which is one embodiment of the present invention. From the results shown in FIG. 29, it can be seen that all the light-emitting elements exhibit high reliability. Therefore, by using the heterocyclic compound of one embodiment of the present invention, it is possible to achieve a longer lifetime of the light-emitting element. It can be seen that...

[0401] Furthermore, a storage test was carried out on the light-emitting elements 1 to 3 and the comparative light-emitting element 5. , Each light-emitting element was stored in a thermostatic chamber maintained at 100°C without being driven, and then left for a specified period of time. After the test, the operating characteristics were measured. The experiment was carried out in an atmosphere maintained at 0.5°C.

[0402] FIG. 30 shows the change in the external appearance over time for the light-emitting elements 1 to 3 and the comparative light-emitting element 5. As a result, the light-emitting elements 1 to 3 each of which is an embodiment of the present invention were 3 maintains its initial external quantum efficiency even after long-term storage at 100°C, demonstrating good heat resistance. In contrast, the comparative light-emitting element 5 maintained the external quantum efficiency in about 10 hours. A significant decrease in efficiency was observed.

[0403] The 2mBbfPDBq used in the light-emitting element 1 and the 2mBbf(II) used in the light-emitting element 2 Both PDBq and 2mBbf(III)PDBq used in light-emitting device 3 have molecular weights of 562. The molecular weight of 2mDBTBPDBq-II used in the comparative light-emitting element 5 is 564. That is, although the light-emitting elements used in the storage test all have similar molecular weights, The durability of the light-emitting elements 1 to 3 and the comparative light-emitting element 5 in a storage test at 100° C. There was a significant difference in thermal stability.

[0404] Between the light-emitting elements 1 to 3 and the comparative light-emitting element 5, 3 has a molecular structure characterized by the presence of a fused aromatic ring, benzobisbenzofuran. The difference in heat resistance observed in the storage test is due to this molecular structure, and It is possible to obtain a compound and a light-emitting device having extremely high heat resistance without increasing the temperature. It was shown that the use of fused rings is very effective. [Example]

[0405] In this example, a heterocyclic compound represented by the following structural formula (101), 2-[ 3-(benzo[1,2-b:4,5-b']bisbenzofuran-6-yl)phenyl]di HOMO levels and LU of benzo[f,h]quinoxaline (abbreviation: 2mBbfPDBq) The MO level was calculated based on cyclic voltammetry (CV) measurements. The calculation method is as follows: show.

[0406] [ka]

[0407] The measurement device used was an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model). The solution used in the CV measurements was dehydrated dimethyl ether. Dimethylformamide (DMF) (Aldrich Corporation, 99.8%, Catalog No. 227 056) was used as the supporting electrolyte, and tetra-n-butylammonium perchlorate (n-Bu 4NClO4) (Tokyo Chemical Industry Co., Ltd., catalog number: T0836) at 100 mmol / L The measurement target is dissolved to a concentration of 2 mmol / L. The working electrode was a platinum electrode (PTE, manufactured by BAS Co., Ltd.). The auxiliary electrode was a platinum electrode (B.A.S. Co., Ltd., VC-3 Pt Counter electrode (5 cm)) and Ag / Ag as reference electrode + Electrode (B.A.S. The measurements were carried out at room temperature (20 to 2 The scan rate during CV measurement was standardized to 0.1 V / sec. The oxidation potential Ea [V] and reduction potential Ec [V] of the electrode were measured. The potential of the original wave is the midpoint potential of the reduction-oxidation wave, and Ec is the midpoint potential of the reduction-oxidation wave. The potential energy of the reference electrode relative to the vacuum level is -4.94 eV. Since we know the HOMO level [eV] = -4.94-Ea, the LUMO level [eV] From the equation =-4.94-Ec, the HOMO and LUMO levels can be calculated. In addition, CV measurement was repeated 100 times, and the oxidation rate at the 100th cycle was The electrical stability of the compound was investigated by comparing the first-cycle oxidation-reduction wave with the first-cycle oxidation-reduction wave.

[0408] As a result, in the measurement of the oxidation potential Ea [V] of 2mBbfPDBq, No clear oxidation peak was observed in the range of 0.5 eV to 1.5 eV. On the other hand, the LUMO level was In addition, the redox wave was measured repeatedly at 10 The oxidation-reduction wave after the 0th cycle peaked at 73% of the oxidation-reduction wave after the 1st cycle. The strength of 2mBbfPDBq was maintained, indicating that it was highly resistant to reduction. It was confirmed that...

[0409] In addition, thermogravimetry-differential thermal analysis (TG-DTA) of 2mBbfPDBq avimetry-Differential Thermal Analysis) The measurements were carried out using a high-vacuum differential thermobalance (manufactured by Bruker AXS Co., Ltd., T The temperature was raised at normal pressure at a rate of 10°C / min under a nitrogen gas flow (flow rate When measurements were taken under the conditions of (200 mL / min), the relationship between weight and temperature (thermogravimetry) was The 5% weight loss temperature of 2mBbfPDBq was approximately 442°C. It was shown that fPDBq has good heat resistance.

[0410] Differential scanning calorimetry (DSC) was performed using a PerkinElmer Pyris1DSC. The differential scanning calorimetry was performed at a temperature rise rate of 50°C / min from -10°C to 3°C. After heating to 70°C, it is kept at the same temperature for 1 minute, and then cooled to -10°C at a rate of 50°C / min. The cooling operation was carried out twice in succession to 2°C, and the second measurement result was used. The glass transition temperature of mBbfPDBq was found to be 147°C, and it has high heat resistance. It was revealed that this compound

[0411] Next, the 2mBbfPDBq obtained in this example was analyzed by liquid chromatography mass spectrometry (LCMS). id Chromatography Mass Spectrometry, abbreviation: L The samples were analyzed by C / MS analysis.

[0412] LC / MS analysis was performed using a Waters Acqui (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo UPLC (registered trademark). The LC separation was performed using an Acquity UPL G2 Tof MS. C BEH C8 (2.1 × 100 mm 1.7 μm), column temperature was 40°C. The mobile phase A was acetonitrile and the mobile phase B was 0.1% formic acid aqueous solution. The pull was performed by dissolving 2mBbfPDBq at an arbitrary concentration in N-methyl-2-pyrrolidone and acetone. The solution was diluted with nitrile and the injection volume was 5.0 μL.

[0413] A gradient method was used for LC separation, which changes the composition of the mobile phase. The mobile phase A:mobile phase B = 65:35, then the composition was changed, and 10 minutes after the start of measurement, The ratio of mobile phase A to mobile phase B in the analysis was set to mobile phase A:mobile phase B=95:5. The total time was 10 minutes, and the composition was changed linearly.

[0414] For MS analysis, electrospray ionization was used. The capillary voltage was 3.0 kV and the sample was ionized by electrospray ionization (ESI). The sample cone voltage was 30 V, and detection was performed in positive mode. The m / z range was 100 to 1200.

[0415] When LC-MS measurements were performed under the above conditions, the ions derived from 2mBbfPDBq were Mass-to-charge ratio (m / z)=563.175([M+H + ], theoretical value of 2mBbfPDBq = Next, the ion with a mass-to-charge ratio (m / z) of 563.175 was detected. (Precursor ions) are dissociated by colliding with argon gas in a collision cell. The energy when the precursor ions collide with argon (collision energy The energy (energy) was set to 50 eV and 70 eV. The collision of precursor ions with argon gas The collision energy of the generated product ions detected by a time-of-flight (TOF) detector The mass spectrum with a collision energy of 50 eV is shown in Figure 31, and the mass spectrum with a collision energy of 70 eV is shown in Figure 32. The vector is shown in Figure 32.

[0416] From the results of FIG. 31, 2mBbfPDBq represented by structural formula (101) is mainly = around 536.165, around m / z=345.091, around m / z=334.098, m Around m / z=305.096, around m / z=229.076, around m / z=202.066 It was found that a product ion was detected around m / z=177.070. From the results of Figure 32, in the measurement with a collision energy of 70 eV, the The 2mBbfPDBq fragments are mainly located around m / z=305.096 and m / z=229. Product images were observed around m / z=077, m / z=202.066, and m / z=176.063. It was found that ON was detected. The results shown in Figures 31 and 32 are for 2mBbfP Since this shows the characteristic results derived from DBq, the 2mBb contained in the mixture This data is important for identifying fPDBq.

[0417] The product ion around m / z=536.165 has the structure shown in the following formula (a): In the compound of formula (101), the nitrogen-containing ring of dibenzo[f,h]quinoxaline is cleaved. It is estimated that this is the structure generated by the product around m / z=345.091. The ion is a dibenzo[f, The bond at the 2-position of [f,h]quinoxaline is cleaved to form dibenzo[f,h]quinoxaline. The product ion at m / z=334.098 is estimated to be derived from the following formula (c): As shown in the structural formula (101), the compound is substituted at the 2-position of dibenzo[f,h]quinoxaline. The bond cleavage yielded 6-phenylbenzo[1,2-b:4,5-b']bisbenzophenone. The product ion at m / z=305.096 is assumed to be derived from orchid. In the compound of structural formula (101), benzo[1,2-b:4,5-b 2-phenyldibenzo[f,h] ']bisbenzofuran is cleaved at the 6-position to form The product ion at m / z=229.076 is presumed to be derived from quinoxaline. In the compound of structural formula (101), dibenzo[f,h]quino is It is believed to be derived from dibenzo[f,h]quinoxaline, which is formed by cleavage of the bond at the 2-position of quinoxaline. It is estimated that the product ion at m / z=202.066 is expressed as shown in the following formula (f). The product ion at m / z=536.165 is further fragmented into ions. The product ion at m / z=177.070 is estimated to be As shown, the product ion at m / z=536.165 was further fragmented to produce the ion. In particular, in the compound of structural formula (101), dibenzo[f,h]quinoxa Formula (a) is an ion formed by the cleavage of the ring containing two nitrogen atoms of phosphorus, and the bond between the rings is The ions produced by cleavage, which are represented by formulas (b) to (d), are 2mBbfP This is one of the characteristics of DBq and is important for identifying 2mBbfPDBq contained in a mixture. This can be said to be important data.

[0418] [ka] [Example]

[0419] In this example, a heterocyclic compound represented by the following structural formula (107), 2-[ 3-(benzo[1,2-b:5,4-b']bisbenzofuran-6-yl)phenyl]di HOMO levels and The LUMO levels were calculated based on cyclic voltammetry (CV) measurements. is shown below.

[0420] [ka]

[0421] The HOMO and LUMO levels of 2mBbf(II)PDBq were investigated by cyclic voltammetry. The CV measurement method and the HOMO and LUMO levels were calculated. The method for calculating the level is the same as in Example 6.

[0422] As a result, in the measurement of the oxidation potential Ea [V] of 2mBbf(II)PDBq, No clear oxidation peak was observed in the range of -0.2 eV to 1.5 eV for LU. The MO level was found to be -2.94 eV. In this study, the oxidation-reduction wave after 100 cycles was 87 times larger than that of the first cycle. % peak intensity, indicating the resistance of 2mBbf(II) PDBq to reduction. was confirmed to be very good.

[0423] In addition, thermogravimetry and differential thermal analysis of 2mBbf(II)PDBq were performed. The same as in Example 6. From the measurement results, the 5% weight loss temperature of 2mBbf(II)PDBq is about The temperature was 459°C. This indicates that 2mBbf(II)PDBq has good heat resistance. It was shown that: [Example]

[0424] In this example, a heterocyclic compound represented by the following structural formula (149), 2-[ 3-(benzo[1,2-b:5,6-b']bisbenzofuran-4-yl)phenyl]di HOMO levels of benzo[f,h]quinoxaline (abbreviation: 2mBbf(III)PDBq) The LUMO level was calculated based on cyclic voltammetry (CV) measurements. The method is shown below.

[0425] [ka]

[0426] The HOMO and LUMO levels of 2mBbf(III)PDBq were investigated by cyclic voltammograms. The calculation was based on the CV measurement. The method for calculating the O level is the same as in Example 6.

[0427] As a result, in the measurement of the oxidation potential Ea [V] of 2mBbf(III)PDBq, No clear oxidation peak was observed in the range of 0 eV to 1.5 eV. The O level was found to be -2.95 eV. The oxidation-reduction wave after 100 cycles was 79% of that in the first cycle. The peak intensity of 2mBbf(III)PDBq was maintained, indicating its resistance to reduction. was confirmed to be very good.

[0428] In addition, thermogravimetry and differential thermal analysis of 2mBbf(III)PDBq were performed. The same as in Example 6. From the measurement results, the 5% weight loss temperature of 2mBbf(III)PDBq The temperature was approximately 454°C. This indicates that 2mBbf(III)PDBq has good heat resistance. Something has been shown. [Example]

[0429] In this example, a heterocyclic compound represented by the following structural formula (150), 2-[ 3'-(benzo[1,2-b:5,6-b']bisbenzofuran-4-yl)-1,1' -biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mBbf(III The HOMO and LUMO levels of BPDBq were determined by cyclic voltammetry (CV The calculation method is shown below.

[0430] [ka]

[0431] The HOMO and LUMO levels of 2mBbf(III)BPDBq were investigated by cyclic boron spectroscopy. The values ​​were calculated based on the CV measurement. The MO level was calculated in the same manner as in Example 6.

[0432] As a result, in the measurement of the oxidation potential Ea [V] of 2mBbf(III)BPDBq, No clear oxidation peak was observed in the fixed range of 0.1 eV to 1.5 eV. The LUMO level was found to be -2.98 eV. In the measurement, the oxidation-reduction wave after 100 cycles was The peak intensity remained at 71%, indicating that the reduction of 2mBbf(III)BPDBq It was confirmed that the resistance to [Explanation of symbols]

[0433] 101 first electrode 102 EL layer 103 Second electrode 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 201 First electrode 202(1) First EL layer 202(2) Second EL layer 202(n-1)th EL layer 202(n) EL layer (n) 204 Second electrode 205 Charge generation layer 205(1) First charge generating layer 205(2) Second charge generating layer 205(n-2) (n-2)th charge generating layer 205(n-1) (n-1)th charge generating layer 301 Element 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 Sealing substrate 307 Wiring 308 FPC (Flexible Printed Circuit) 309 FET 310 FET 312 Current control FET 313a, 313b First electrode (anode) 314 Insulators 315 EL layer 316 Second electrode (cathode) 317a, 317b Light-emitting element 318 Space 320a, 320b conductive film 321, 322 area 323 Wiring 324 Colored layer (color filter) 325 Black layer (black matrix) 326, 327, 328 FETs 401 Substrate 402 First electrode 404 Second electrode 403a, 403b, 403c EL layer 405 Light-emitting element 406 Insulating film 407 Bulkhead 900 boards 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Light-emitting layer 914 Electron transport layer 915 Electron injection layer 2000 touch panel 2501 Display Panel 2502R pixels 2502t transistor 2503c Capacitive element 2503g Scanning line driver circuit 2503t transistor 2509 FPC 2510 board 2511 Wiring 2519 terminal 2521 Insulation layer 2528 Insulator 2550R light emitting element 2560 Sealing Layer 2567BM light shielding layer 2567p anti-reflection layer 2567R colored layer 2570 board 2590 board 2591 Electrode 2592 Electrode 2593 Insulation Layer 2594 Wiring 2595 Touch Sensor 2597 Adhesive layer 2598 Wiring 2599 terminals 2601 Pulse voltage output circuit 2602 Current detection circuit 2603 Capacity 2611 Transistor 2612 transistor 2613 Transistor 2621 Electrode 2622 Electrode 4000 lighting equipment 4001 board 4002 Light-emitting element 4003 board 4004 Electrode 4005 EL layer 4006 Electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4100 Lighting equipment 4200 Lighting Equipment 4201 Circuit Board 4202 Light-emitting element 4204 Electrode 4205 EL layer 4206 Electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulation layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 4300 Lighting Equipment 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rearview mirror 7100 Television equipment 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7302 Housing 7304 Display section 7305 Time Icon 7306 Other Icons 7311 Operation button 7312 Operation button 7313 Connection terminal 7321 Band 7322 Clasp 7400 mobile phone 7401 Housing 7402 Display section 7403 Operation buttons 7404 External connection part 7405 Speaker 7406 Microphone 7407 Camera 7500(1), 7500(2) enclosure 7501(1), 7501(2) 1st page 7502(1), 7502(2) 2nd page 8001 Lighting equipment 8002 Lighting equipment 8003 Lighting equipment 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 chassis

Claims

[Claim 1] A compound represented by the following formula: 【Chemistry 1】

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