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 a heterocyclic compound and a novel synthesis 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. It is to be noted that one embodiment of the present invention is not limited to the above technical field. [Background technology]

[0002] The organic compound used as the light emitter has characteristics such as being thin and lightweight, having high-speed response, and being driven by a low direct current voltage. The light-emitting element is expected to be applied to the next generation of 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 corners and excellent visibility.

[0003] The mechanism of light emission 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 luminescence 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 they emit light by releasing the light. There are two types of excited states: singlet excitation and triplet excitation. 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 the light-emitting 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] JP 2007-189001 A 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 that are easy to emit have a short life span. Therefore, when other skeletons are directly bonded to the dibenzo[f,h]quinoxaline ring, the conjugated system becomes more extensive. This may cause a decrease in triplet excitation energy. If the compound is used, the light-emitting efficiency decreases, and the characteristics of the light-emitting device using the compound also decrease. I end up doing this.

[0007] In view of the above, one embodiment of the present invention provides a novel heterocyclic compound. The present invention provides a novel heterocyclic compound capable of improving the optical properties. In addition, the present invention provides a novel heterocyclic compound having good luminous efficiency and heat resistance. The present invention provides a novel heterocyclic compound that can be used in a light-emitting element. In the present invention, a novel heterocyclic compound that can be used in the EL layer of a light-emitting device is provided. Light-emitting elements with high heat resistance, high luminous efficiency and low power consumption, and long life In addition, in one embodiment of the present invention, a novel light-emitting element is provided. The present invention provides a novel light-emitting device, a novel electronic device, or a novel lighting device. The above description 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 become apparent from the description of the specification, 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 substituted or unsubstituted dibenzo[f,h]quinoxalinyl group and a substituted 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 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. r1 and Ar 2 When the arylene group represented by the formula: has a substituent, the substituents are bonded to each other may form a ring.

[0012] In another embodiment of the present invention, in the above general formula (G1), DBq is a substituted or unsubstituted represents a dibenzo[f,h]quinoxalinyl group, Ar 1 is a substituted or unsubstituted carbon atom number 6 represents an arylene group having a molecular weight of 1 to 13, n represents 0 or 1, Ar 2 is substituted or unsubstituted A represents an arylene group having 6 to 13 carbon atoms, and A is a substituted or unsubstituted benzobisbenzo The furanyl group is represented by the benzobisbenzofuranyl group. Of these, one of the carbons adjacent to the carbon bonded to the oxygen of the furan ring is Ar 2 Combine with Also, Ar 1 and Ar 2 When the arylene group represented by the formula: has a substituent, the substituent is They may also be bonded to each other 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. S, R 1 ~R 9 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a 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, Ar 2 also substitute 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, Characterized in that 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 represented by the following general formula: Any one of general formulas (A1) to (A3), wherein in general formula (A1) to (A3), Among the carbons that do not constitute the furan ring, the carbon adjacent to the carbon bonded to the oxygen in the furan ring Any one of the following is 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 substituent is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a 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 embodiment 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 light-emitting substances (dopants) such as optical materials. This can be done.

[0024] In addition, 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, etc. The heterocyclic compound according to the embodiment is a light-emitting material. Therefore, in the light-emitting layer, a light-emitting material such as a phosphorescent material is used. It can be used not only as a host material in combination with a substance, but also as a light-emitting material. Therefore, a light-emitting element using a heterocyclic compound according to one embodiment of the present invention can be It is intended to be included in the embodiments.

[0025] That is, another aspect 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 relates to a light-emitting device using a heterocyclic compound having an arylene group bonded thereto. .

[0026] Another embodiment of the present invention is a substituted or unsubstituted dibenzo[f,h]quinoxalinyl A substituted or unsubstituted benzobisbenzofuranyl group is The benzobisbenzofuranyl group is bonded via a rylene group and does not constitute a furan ring. Among the carbons, any 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. Also, a light emitting device may have 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) ) method, all modules in which ICs (integrated circuits) are directly mounted are also included in the light-emitting device. do. Effect 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 characteristics. 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 provided. In one embodiment of the present invention, the organic EL element can be used for an EL layer of a light-emitting element. In particular, it is possible to provide a novel heterocyclic compound having a high heat resistance, It is possible to provide a light-emitting element that is highly efficient and consumes low power, and that has a long life. According to one embodiment of the present invention, a novel light-emitting element can be provided. It is possible to provide a novel electronic device or a novel lighting device. [Brief description of the drawings]

[0030] [Figure 1] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 2] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 3] 1A and 1B are diagrams illustrating a light-emitting device. [Figure 4] 1A and 1B are diagrams illustrating a light-emitting device. [Diagram 5] 1A to 1C are diagrams illustrating electronic devices. [Figure 6] 1A to 1C 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. 2 is a diagram showing an example of a touch panel. [Figure 11] FIG. 2 is a diagram showing an example of a touch panel. [Figure 12] FIG. 2 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 spectrum and emission spectrum of the heterocyclic compound represented by 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 represented by 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). [Diagram 23] 1A to 1C are diagrams illustrating light-emitting elements. [Figure 24] FIG. 13 shows current density-luminance characteristics of Light-emitting Elements 1 to 4. [Diagram 25] FIG. 13 shows voltage-luminance characteristics of Light-emitting Elements 1 to 4. [Figure 26] FIG. 13 shows luminance vs. current efficiency characteristics of Light-emitting Elements 1 to 4. [Figure 27] 13 shows voltage-current characteristics of Light-emitting Elements 1 to 4. [Figure 28] FIG. 13 shows emission spectra of Light-emitting Elements 1 to 4. [Figure 29] 13 shows the reliability of Light-emitting Elements 1 to 4. [Diagram 30] 13 is a graph showing changes over time in external quantum efficiency characteristics of the light-emitting elements 1 to 3 and the comparative light-emitting element 5. [Diagram 31] Mass spectrum of 2mBbfPDBq. [Diagram 32] Mass spectrum of 2mBbfPDBq. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0031] Hereinafter, the embodiment 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 are not limited thereto without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the above embodiment. It is not to be construed as being limited to the following:

[0032] The words "membrane" and "layer" may be interchangeable depending on the situation. For example, the term "conductive layer" can be used interchangeably with the term "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 and a substituted or unsubstituted benzobisbenzofuranyl group are The heterocyclic compound is characterized in that the ring is bonded via a substituted arylene group.

[0035] Generally, by increasing the number of condensed rings that form the molecular structure of an organic compound, The heat resistance of organic compounds with this structure increases as their molecular weight increases, and they are used in light-emitting devices. However, simply increasing the number of condensed rings is not enough. Since the molecular structure becomes more planar, thin films of organic compounds tend to crystallize more easily. 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 solubility of the compound. This leads to a 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 having a fused ring containing a heteroatom. By extending the molecular skeleton, compounds with high T1 levels can be provided. The highly planar dibenzo[f,h]quinoxalinyl group and benzobisbenzofuranyl group are By bonding via olefin groups, a bulky compound is formed, which suppresses crystallization and improves heat resistance. Therefore, the heterocyclic compound described in this embodiment can be represented 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 a substituent, the substituents are bonded to each other may form a ring.

[0038] In another embodiment, in the heterocyclic compound represented by the general formula (G1), DBq represents a substituted or unsubstituted dibenzo[f,h]quinoxalinyl group, 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; A represents a substituted or It represents an unsubstituted benzobisbenzofuranyl group. Among the carbons that do not constitute a furan ring, any of the carbons adjacent to the carbon bonded to the oxygen of the furan ring First, Ar 2 Also, Ar 1 and Ar 2 The arylene group represented by the formula 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 the formula: is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, a substituted or unsubstituted and substituted or unsubstituted biphenyldiyl groups, and substituted or unsubstituted fluorenediyl groups. More specifically, the arylene groups include those represented by the following structural formulas (α1) to (α15). can be.

[0040] [ka]

[0041] In addition, 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) or (A8).

[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 substituent is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group 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 the aryl group.

[0044] In addition, when the general formulae (A1) to (A7) each 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, isobutyl, tert-butyl, pentyl, isopentyl, s ec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl sec-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3- Examples thereof 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 a group include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. 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, and an isopropyl group. Examples thereof include an aryl group and an isopropyl 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 A phenyl group, a 4-biphenyl group, or another aryl group having 6 to 12 carbon atoms, These substituents may be bonded to each other to form a ring. For example, the arylene group fluorene-diyl has two phenyl groups at the 9-position as substituents. When the phenyl group is a 9,9-diphenyl-9H-fluorene-2,7-diyl group having the formula Even if the 2,3-nyl groups are bonded to each other to form a spiro-9,9'-bifluorene-2,7-diyl group, good.

[0048] Another embodiment of the heterocyclic compound of the present invention is 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. S, R 1 ~R 9 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a 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, Ar 2 also substitute 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 shown below. 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) or (A8).

[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 substituent is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group 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 the aryl group.

[0056] In addition, when the general formulae (A1) to (A7) each 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, isobutyl, tert-butyl, pentyl, isopentyl, s ec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl sec-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3- Examples thereof 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 a group include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. 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, and an isopropyl group. Examples thereof include an aryl group and an isopropyl group.

[0059] In addition, R in general formula (G2) 1 ~R 9 Specific examples of the alkyl group 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 hexyl, tert-hexyl, neohexyl, 3-methylpentyl, 2-methylpentyl 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 The following groups are available: phenyl group, biphenyl group, tolyl group, naphthyl group, xylyl group, and 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 a 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 A phenyl group, a 4-biphenyl group, or another aryl group having 6 to 12 carbon atoms, These substituents may be bonded to each other to form a ring. For example, the arylene group fluorene-diyl has two phenyl groups at the 9-position as substituents. When the phenyl group is a 9,9-diphenyl-9H-fluorene-2,7-diyl group having the formula Even if the 2,3-nyl 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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[0069]

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[0070]

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[0075]

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[0076]

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[0078]

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[0079]

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[0080]

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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 included in the heterocyclic compounds represented by the above general formulas (G1) and (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 the 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 a substituent, the substituents are bonded to each other A ring may be formed by a carbon atom not constituting a furan ring of the benzobisbenzofuranyl group. Among them, one of the carbons adjacent to the carbon bonded to the oxygen of the furan ring is Ar 2 Combined with This is also 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, Ar 1 is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. n represents 0 or 1; Ar 2 is a substituted or unsubstituted alkyl group having 6 to 13 carbon atoms. A represents a substituted or unsubstituted benzobisbenzofuranyl group. Also, Ar 1 and Ar 2When the arylene group represented by the formula: has a substituent, the substituent is They may also be bonded to each other to form a ring.

[0098] In addition, in the synthetic scheme (A), the Suzuki-Miyaura coupling reaction using a palladium catalyst was carried out. When responding, X 1 and X 2 is a halogen group, a boronic acid group, an organic boron group, or a trifuranic acid group. 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 tetrakis(triphenylphosphine)palladium(0) 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 the reaction shown in the synthesis scheme (A), an organic salt such as sodium tert-butoxide is used. bases, and inorganic bases such as potassium carbonate, cesium carbonate, and sodium carbonate can be used. In addition, toluene, xylene, benzene, tetrahydrofuran, dioxane, Examples of solvents that can be used include ethanol, methanol, and water. The reagents are not limited to those mentioned above.

[0100] In addition, the reaction in the synthetic scheme (A) is not limited to the Suzuki-Miyaura coupling reaction. Instead, organotin compounds were used in the Migita-Kosugi-Stille coupling reaction and the Grignard reaction. Kumada-Tamao-Corleau coupling reaction using a reagent, and Negishi coupling reaction using an organozinc compound A pulling reaction, a reaction using copper or a copper compound, etc. 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 organic tin group, and the other represents a halogen group. That is, 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 one of Compound 1 and 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 compounds 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] As described above, an example of a method for synthesizing a heterocyclic compound has been described 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. It is also possible to use these heterocyclic compounds as light-emitting materials in light-emitting devices. A light-emitting element including the object is also included in one embodiment of the present invention.

[0107] In addition, by using the heterocyclic compound which is one embodiment of the present invention, a light-emitting element and an emitter having 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. In the following, one embodiment of the present invention will be described. However, the present invention is not limited to the above. That is, 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 has been described, 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 configuration described in this embodiment may be used in appropriate combination with the configurations described 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 FIG.

[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 a cathode 103 and a 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-induced ... will emit light.

[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 material having a high hole transporting property and an access In this case, the hole is absorbed by the acceptor material. When electrons are removed from a material with high transport properties, holes are generated. Holes are injected from the hole injection layer 111 through the hole transport layer 112 into the light emitting layer 113. The hole injection layer 111 may be made of a material having a high hole injection property. Butan oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide Other examples include phthalocyanine (abbreviation: H2Pc) and copper phthalocyanine. Phthalocyanine compounds such as CuPC, 4,4'-bis[N-(4-diphenylphosphine 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(styrenesulfonyl) The hole injection layer 111 may be formed from a polymer such as 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 Indium oxide-tin oxide, Indium oxide-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, elements in the first or second group of the periodic table, such as lithium (Li) and cesium (Ce), Alkali metals such as Cs, calcium (Ca), strontium (Sr), etc. Alkaline earth metals, magnesium (Mg), and alloys containing these (MgAg, Al Li), europium (Eu), ytterbium (Yb), and other rare earth metals, 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 can be, for example, The insulating 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 an aromatic compound 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 .DELTA..times ... The layer 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 a hole transporting material 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 N-(1-naphthyl)-N-phenylamino]benzene (abbreviation: DPA3B), N,N'-bis(3-phenylamino)biphenyl (abbreviation: NPB or α-NPD) N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamino TPD, 4,4',4''-tris(carbazol-9-yl)triphenylphosphine 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) PCzPC A1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenyla Amino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl -N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazol In addition, 4,4'-di(N- Carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl) 9-[4-(10-phenyl-9-aryl)phenyl]benzene (abbreviation: TCPB), 1,4-bis[4- (N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. It is possible.

[0119] As the aromatic hydrocarbon, for example, 2-tert-butyl-9,10-di(2-naphthalene) 2-tert-butyl-9,10-dianthracene (abbreviation: t-BuDNA), (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-diphenylanthracene (abbreviation: DNA), 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 anthracene, 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 a carbon number of 14 to 42. The aromatic hydrocarbon may have a vinyl skeleton. Examples of the compound include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: D PVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), etc.

[0120] In addition, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylphosphine) 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 Poly(phenyl)benzidine (abbreviation: Poly-TPD) can also be used. can.

[0121] The acceptor substances 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 having a phenyl group or a cyano group such as HAT-CN can be mentioned. Compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms are thermally stable. Further, oxides of metals belonging to Groups 4 to 8 of 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 them, 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.

[0122] The light-emitting layer 113 is a layer containing a light-emitting substance. The phosphorescent light-emitting material may be, for example, an organic In the light-emitting layer 113, an organometallic 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 During the recombination of carriers (electrons and holes) in the excited state, an excited complex (also called an exciplex) is formed. Two types of organic compounds (the above-mentioned host materials) that can be combined to form a compound In order to efficiently form an exciplex, To achieve this, we need compounds that easily accept electrons (materials with electron transport properties) and compounds that easily 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. In the case of using a host material having electron transport properties and a material having hole transport properties as a mixture, 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, It is possible to prevent the recombination of electrons and holes from occurring in a biased area 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 for forming the above exciplex ( As materials having electron transport properties, π-electron-deficient heteroaromatic compounds such as nitrogen-containing heteroaromatic compounds are Aromatic compounds and metal complexes can be used. 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-benzoyl) 2- (4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxazolidinyl Azole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tetraphenyl) rt-Butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[ 5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]be OXD-7, 9-[4-(5-phenyl-1,3,4-oxadiazo 2,2',2''-phenyl)-9H-carbazole (abbreviation: CO11) -(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) ) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1- Polyazides such as phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds with a phenyl skeleton and 2-[3-(dibenzothiophene-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-(dibenzo[f,h]quinoxaline 7mD BTPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl] Dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-bis[ 3-(Phenanthren-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] 4,6-diphenyl-1,3,5-triazine (abbreviation 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 diazine skeleton Heterocyclic compounds having a triazine skeleton and heterocyclic compounds having a pyridine skeleton are reliable. In particular, diazine (pyrimidine or pyrazine) skeletons and triazine skeletons are preferred. The heterocyclic compound having a skeleton has a high electron transporting property and contributes to a reduction in the 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 having hole transport properties, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives) In particular, an aromatic amine or an indole derivative can be preferably 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-phenylcarba (3-yl)-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-dimethyl Luorene-2,7-diamine (abbreviation: YGA2F), NPB, N,N'-bis(3-methyl 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] 9H-fluoren-7-yl)amino]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) (III)triphenylamine (abbreviation: PCBA1BP), 4,4'-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 9,9'-bifluorene-2-yl-9H-carbazol-3-ylphenyl 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 (abbreviation: PCBBiF) and other compounds with aromatic amine skeletons, mCP, CBP, 3,6-bis(3,5-diphenyl ether) 9-phenyl-9-phenylcarbazole (abbreviation: CzTP) H-3-(9-phenyl-9H-carbazol-3-yl)carbazole (abbreviation: PCC P), and 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 Zothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoro [oren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP -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 having a furan skeleton include compounds having 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 addition, the light-emitting layer 113 contains the above-mentioned organometallic complex (guest material) and the host material. By forming the light-emitting layer 113 in this manner, phosphorescence with high luminous efficiency can be obtained from the light-emitting layer 113. 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 be a laminated structure of two or more layers as shown in (B). In this case, however, For example, the first light-emitting layer 113 (a1 Fluorescent light is emitted from the second light-emitting layer 113 (a 2) can be configured to emit phosphorescence. The stacking order can be reversed. In the layer from which phosphorescence can be obtained, the energy from the exciplex to the dopant may be It is preferable that the light emitted is due to the transfer of energy. The color of the light emitted from one layer may be different from the color of the light emitted from the other layer even if they are the same. However, when 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 emit orange or yellow light. Furthermore, each layer may contain a plurality of types of dopants.

[0127] In addition, 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 used in combination:

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

[0129] The fluorescent substance is 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 ]-9H-Carbazole-3-amine (abbreviation: PCAPA), Perylene, 2,5,8,1 1-Tetra(tert-butyl)perylene (abbreviation: 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'''-Octaphenyldiphenyl Benzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Marine 30, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9 H-Carbazole-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-triphenylanthracene-9-amine (abbreviation: DPhA PhA), Coumarin 545T, N,N'-Diphenylquinacridone, (abbreviation: DPQd) , Rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyl BPT, 2-(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 Dopanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylfuran) p-mPhTD, 7,14-diphenyltetracene-5,11-diamine 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-(2-phenylenedinitrile) [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) (phenyl)ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethylphenyl] Chil-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-yl Bis(ethyl)ethenyl)-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDC JTM) etc.

[0130] Examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials ( Fluorescent compounds and thermally activated delayed fluorescence (TADF) materials The delayed fluorescence in TADF materials is similar to that of normal fluorescence. It is a type of light emission that has a spectrum and has an extremely long lifespan. Its lifespan is approximately 1×10-6 seconds or more Above, preferably 1×10 -3 More than seconds.

[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’ ) Iridi Ir(III) acetylacetonate (abbreviation: [Ir(bt)2(acac)]), bis [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-phenylpropanediol) [Ir(mppr-Me)2(aca c)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenyl Pyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac) ]), (acetylacetonato)bis(2,3,5-triphenylpyrazinate)iridium (III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylphosphine) (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-propanedione)(monofena (Eu(DBM)3(Phen)]), Tris[1-(2-phenanthroyl)-3,3,3-trifluoroacetonato](monophenanthroyl) Europium(III) (abbreviation: [Eu(TTA)3(Phen)]) Can be obtained.

[0132] In addition, TADF materials include, for example, fullerene and its derivatives, and activators such as proflavine. Lysine derivatives, eosin, etc. Magnesium (Mg), zinc (Zn), Cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or para Examples of the metal-containing porphyrin include porphyrins containing palladium (Pd) and the like. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2 (Protoporphyrin-tin fluoride complex) IX), mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (abbreviation: 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)), Octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP) and the like. In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2, 3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ The present invention uses heterocyclic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, such as In addition, the π-electron rich heteroaromatic ring and the π-electron deficient heteroaromatic ring can be directly bonded to each other. The materials obtained by this study have the donor properties of π-electron-rich heteroaromatic rings and the acceptor properties of π-electron-deficient heteroaromatic rings. This is particularly preferred because the valence 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 high electron transporting properties (also referred to as an electron transporting 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)benzothiazolato] Metal complexes such as zinc (abbreviation: Zn(BTZ)2) can be used. OXD-7, TAZ, 3-(4-tert-butylphenyl)-4-(4-ethylphenyl) p-EtTAZ , Bathophenanthroline (abbreviation: Bphen), Bathocuproine (abbreviation: 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 can also be used. is mainly 1×10 -6 cm 2 / Vs or higher. As long as the substance has a higher electron transporting property than the above, the electron transporting layer 114 may be formed using any substance other than the above. Good too.

[0134] The electron transport layer 114 may be a single layer or 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 of the formula: In addition, an electride may be used for the electron injection layer 115. The electride is, for example, a mixed oxide of calcium and aluminum with electrons. The above-mentioned material constituting the electron transport layer 114 may be a material containing a high concentration of can also be used.

[0136] In addition, the electron injection layer 115 is made of a composite material obtained by mixing an organic compound and an electron donor. Such composite materials are made by adding electrons to organic compounds by electron donors. 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 metal is preferably an alkali metal, an alkaline earth metal, or a rare earth metal, and more preferably lithium, cesium, maium, 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, Barium oxide and the like can be used. 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 , and the electron injection layer 115 are formed by deposition (including vacuum deposition), printing (for example, letterpress printing), respectively. printing method, intaglio printing method, gravure printing method, lithographic printing method, stencil printing method, etc.), inkjet method The above-mentioned methods, such as coating method, can be used alone or in combination. 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 be made of 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 is 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-type 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 a 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 the 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 only one of them 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 In the case where the configuration is the same, the second embodiment can be applied.

[0143] In addition, a first EL layer 202(1), a second EL layer 202(2) and a second EL layer 202(3) are provided between the plurality of EL layers. The charge generating layer 205 is connected to the first electrode 201 and the second electrode 204. When the organic electroluminescent device is turned on, it has a function of injecting electrons into one EL layer and injecting holes into the other EL layer. In the present 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] In addition, the charge generating layer 205 has a translucency 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 made of an organic compound with high hole transport properties to which an electron acceptor is added. Even if the structure is such that an electron donor is added to an organic compound with high electron transport properties, In addition, both of these configurations may be laminated.

[0146] In the case where an electron acceptor is added to an organic compound having a high hole transporting property, As the organic compound having high transmittance, the hole injection layer 111 and the hole transport layer 1 in the second embodiment are The materials shown in 12 as having high hole transport properties can be used. For example, N Using aromatic amine compounds such as PB, TPD, TDATA, MTDATA, and BSPB, The substances 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] In addition, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene is used as an electron acceptor. Examples of the fluorinated compounds 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 they have 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 transport layer 114 used in the second embodiment may be The substances shown as having high transmittance 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 thazole 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, other organic compounds that have a higher electron transporting property than holes can be used. Quality may also be used.

[0149] The electron donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or The metals belonging to the second and thirteenth groups 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] In addition, the charge generating layer 205 is formed using the above-mentioned material, and the EL layer is laminated. In addition, the formation of the charge generating layer 205 can suppress an increase in the driving voltage. 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 (n is 3 or more) EL layers (202(1) to 202(n)) are laminated. The present invention can be similarly applied to the light emitting device according to the present embodiment. In the case of a device having multiple EL layers between a pair of electrodes, By disposing the charge generating layers (205(1) to 205(n-1)), the current density is kept low. Since the current density can be kept low, it is possible to produce long-life elements. It can be achieved.

[0152] In addition, by making the emission color of each EL layer different, the light-emitting device as a whole can have a desired color. For example, in a light-emitting element having two EL layers, the first By making the emission color of the first EL layer and the emission 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. A combination in which yellow or orange light is emitted from the EL layer of 2 is possible. In this case, The blue and yellow (or orange) emissions are both the same fluorescent or phosphorescent emission. It is not necessary that the blue emission is fluorescent and the yellow emission (or orange emission) is phosphorescent. A combination of these and vice versa may also be used.

[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] (Embodiment 4) 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 either a passive matrix type or an active matrix type. The light-emitting device shown in this embodiment may be a light-emitting device having the same structure as the light-emitting device described in the other embodiment. Photonic 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. The active matrix type light emitting device is provided 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 driving 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] In addition, 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 to which the signal is transmitted. An example of providing an FPC (flexible printed circuit) 308 as an external input terminal is shown below. 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. A driver circuit portion 303 which is a source line driver circuit and a pixel portion are formed. 3, a pixel portion 302 is shown.

[0161] The driving circuit section 303 is exemplified by a configuration in which a FET 309 and a FET 310 are combined. The driving circuit section 303 is a transistor of a single polarity (either N-type or P-type). The circuit may be formed of 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 the figure shows a driver integrated into the board, this is not necessarily required and the driver may be externally mounted. A circuit 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 provided with 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 may 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 For example, an amorphous semiconductor film or a crystalline semiconductor film can be used without being limited thereto. 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). l, Ga, Y, Zr, La, Ce, Hf or Nd). FET309, 3 10, 312, for example, an energy gap of 2 eV or more, preferably 2.5 eV By using an oxide semiconductor material having a capacitance of 3 eV or more, more preferably 3 eV or more, The off-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. 3B, 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, the conductive film 320a and the conductive film 320b are The thickness of the first electrodes (313a, 313b) is different from that of the second electrodes (313a, 313b). Here, a positive photosensitive acrylic resin is used as the insulator 314. In this embodiment, the first electrode (313a, 13b) is used as the anode.

[0165] It is also preferable to form a curved surface having a curvature at the upper end or lower end of the insulator 314 . By forming the shape of the insulator 314 as described above, the film formed on the upper layer of the insulator 314 For example, the material of the insulator 314 may be a negative type Either a photosensitive resin of the type 1 or a positive photosensitive resin can be used. Not limited to inorganic compounds, such as silicon oxide, silicon oxynitride, silicon nitride, etc. It is possible.

[0166] An EL layer 315 and a second electrode 316 are laminated on the first electrodes (313a, 313b). The EL layer 315 is provided with at least a light-emitting layer, and the first electrode (313a , 313b), an EL layer 315 and a second electrode 316 constitute a light-emitting element (317a, 317b). In the example shown in FIG. 1B, the end of the EL layer 315 is covered with a second electrode 316. The layer 315 may have a single layer structure or a stacked structure as shown in the second embodiment or the third embodiment. 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 the following materials: 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) of the second electrode 316 is electrically connected to the lead wiring 323 in the region 322. Although not shown here, an external signal is input via the FPC 308.

[0168] In addition, in the cross-sectional view shown in FIG. 3B, only two light-emitting elements 317 are shown. In the example shown in FIG. 02, a plurality of light-emitting elements are arranged in a matrix. That is, The pixel unit 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 emit three types of light (e.g., (R, G, B)) and four types (e.g., (R, G and forming a light emitting element or the like 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 according to the light-emitting color of the light-emitting element (so-called "color-splitting" 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 emit several different kinds of light, it is possible to improve color purity and reduce power consumption. This can reduce power consumption. Furthermore, by combining it with quantum dots, A light emitting device with improved efficiency and reduced power consumption may also be provided.

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

[0170] In addition, 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 partially Alternatively, one or both of the light emitting elements 317a and 317b may be provided. The resulting light emission is extracted to the outside via the colored layer (color filter) 324 .

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

[0172] In addition, it is preferable to use an epoxy resin or glass frit for the sealing material 305. It is desirable that these materials are 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, for example, polyester or acrylic can be used as a sealing material. When using glass frit, 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 is different from that shown in FIG. 3B in that the position of the gate electrode is The FETs 326, 327, and 328 shown in FIG. 3(C) have different structures. The color layer (color filter) 3 provided on the sealing substrate 306 may be formed as shown in FIG. 24 is located at a position where it overlaps with the black layer (black matrix) 325 as shown in FIG. Furthermore, it may be provided so as to overlap with the adjacent color layer (color filter) 324 .

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

[0175] In addition, 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 type light emitting device.

[0176] 4(A) and (B) show a passive matrix light-emitting device. FIG. 4(B) shows a top view of a matrix type light emitting device, and FIG. 4(B) 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. 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 in contact with one side wall and the other side wall as they approach the substrate surface. The side wall has a slope such that the distance between the side wall becomes narrower.

[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 placed 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. c) and the second electrode 404. b, EL layer 403c each emit a different light color (e.g., red, green, blue, yellow, orange, white, etc.). An example of when this occurs 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 type 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 the substrate is not limited to a specific one. An example of the substrate is as follows: Examples of the substrate include semiconductor substrates (e.g., 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 materials, 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), Examples of plastics include 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, a transistor is manufactured using a semiconductor substrate, a single crystal substrate, or an SOI substrate. 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 degree of integration 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 separated from the substrate after a semiconductor device is partially or entirely completed thereon. The device can be used to transfer the device to another substrate. The element can be transferred to 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 For example, 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 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 to which the transistor or the light-emitting element is transferred is In addition to substrates on which a transistor or 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 regenerated fibers Fibers (including acetate, cupra, rayon, recycled polyester, etc.), leather substrates, The use of these substrates allows for the formation of transistors with good characteristics. Formation of transistors with low power consumption, 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 are completed using a light-emitting device which is one embodiment of the present invention. An example of a car will be explained below.

[0187] As an example of an electronic device to which a light-emitting device is applied, 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, audio playback 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. A television device 7100 includes a housing. 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 which is one embodiment of the present invention can be used for the display portion 7103. In addition, a 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 by a separate remote control device 7110 shown in FIG. The operation keys 7109 on the 0 allow you to control the channel and volume, and the display The image displayed on the remote control unit 7103 can be operated. 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 includes a receiver and a modem. It is possible to receive more general television broadcasts, and furthermore, to receive them by wire or wirelessly via a modem. By connecting to a communication network, 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 according to 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) mounted thereon.

[0192] FIG. 5C shows a smart watch. The smart watch includes a housing 7302, a display unit 7304, and an operation button 7306. 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. 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 unit, Functions such as displaying calendars, dates, or times, and various software (programs) The function of controlling processing by the wireless communication function, It has a function to connect to a data network, and a wireless communication function to transmit or receive various data. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It may have the function of

[0195] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity) degree, rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays. 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. 5D shows an example of a mobile phone (including a smartphone). Mobile phone 7 400 is a housing 7401, a display unit 7402, a microphone 7406, a speaker 7405, a camera The device is equipped with a camera 7407, an external connection unit 7404, and an operation button 7403. When a light-emitting device is manufactured by forming a light-emitting element according to one embodiment of the present invention 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 is displayed by touching a display portion 7402 with a finger or the like. You can also make a call or write an email by 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 is mainly used for displaying images. The first mode is a display mode, the second is an input mode for inputting information such as characters, and the third mode is a display mode. This is a display + input mode that combines the display mode and the input mode.

[0199] For example, when making a call or composing an e-mail, the display unit 7402 is used to input characters. The main character input mode is to 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 is nice.

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

[0201] The screen mode can be changed by touching the display portion 7402 or by operating the housing 7401. The type of image displayed on the display unit 7402 can be changed by operating the button 7403. For example, the image signal to be displayed on the display unit may be changed by 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 If there is no input by touch operation of 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 palm or fingers of the user on the sensor 02 and capturing an image of the palm print or fingerprint, the user can be authenticated. 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 image finger veins, palm veins, etc.

[0204] Furthermore, as another configuration of a mobile phone (including a smartphone), FIG. 5(D'-1) and FIG. The present invention can also be applied to a mobile phone having a structure such as that shown in FIG. 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, etc., is 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 surfaces 7502(1) and 7502(2). With this structure, the mobile phone can be stored in a breast pocket without Uses text and image information displayed on pages 7502(1) and 7502(2) on the second page This can be easily verified by the person in charge.

[0206] In addition, as an electronic device to which a light-emitting device is applied, a folding type as shown in FIGS. FIG. 6A shows a portable information terminal 931 in an unfolded state. 0. Also, FIG. 6(B) shows the state of the unfolded or folded state. The mobile information terminal 9310 is shown in a state in the middle of changing. The portable information terminal 9310 is in a folded state. The FOMA terminal is highly portable, and when unfolded, it has a seamless, wide display area that provides 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 gap between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device according to 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 frequently used apps and program shortcuts. 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 vehicle can be equipped with the outside lane of the vehicle shown in FIG. The door 5101 (including the rear of the vehicle), the tire wheel 5102, and part of the door 5103 The display unit 51 shown in FIG. 7B can be applied to the entire vehicle. 04, Handle 5105, Shift lever 5106, Seat 5107, Inner rear bi It can be applied to the mirror 5108, etc. It can also be applied to a part of the glass window. stomach.

[0209] As described above, an electronic device or an automobile can be obtained by using 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] (Embodiment 6) In this embodiment, a configuration 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 a lighting device. (A) and (B) are bottom emission type lighting devices that extract light from the substrate side. C) and (D) are top-emission type 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 over a substrate 4001. The light emitting element 4002 has a substrate 4003 having projections and recesses 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. This can improve the efficiency of extracting the light generated in 02.

[0216] In addition, instead of the substrate 4003, as in the illumination device 4100 of FIG. 8(B), A diffuser 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 4 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 421 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 projections and recesses as shown in FIG. The extraction efficiency of the 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 provided as in a lighting device 4300 of FIG. 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, Alternatively, the light-emitting element may have a structure having a support. 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, 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 because it is possible to make a large-area lighting device. By using a housing having such a shape, it is possible to form a lighting device 8002 having a curved light-emitting area. 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 various elaborate designs can be formed. Furthermore, lighting devices 8003 may be provided on the walls inside the room.

[0225] In addition to the above, by applying light-emitting devices to some of the furniture in the room, It is possible to provide a lighting device having the functions as above.

[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 shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. 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 provided will be described with reference to FIGS.

[0229] 10(A) and (B) are perspective views of the touch panel 2000. 2, 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 includes a plurality of pixels on a substrate 2510 and a display device 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 wire loop, part of which constitutes the terminal 2519. The terminal 2519 is an FPC 2509 (1) and electrically connect it.

[0232] The substrate 2590 includes 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 in FIG. 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 capacitive touch sensor can be used. The capacitance type includes a surface type capacitance type and a projected type capacitance type.

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

[0235] First, in the case of applying a projected capacitive touch sensor, FIG. 10(B) is used to explain the case. In the case of the projected capacitive type, the proximity or contact of a detection target such as a finger is detected. Various sensors capable of detecting the above-mentioned phenomenon can be applied.

[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 a plurality of wirings 2598. In addition, the electrodes 2592 are repeatedly connected in one direction as shown in FIG. A shape in which multiple quadrilaterals are arranged in a repeated manner and connected in one direction at the corners by wiring 2594. 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 thus to reduce variations in transmittance. As a result, the variation in the brightness of the 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 to each other via an insulating layer. In this case, two adjacent electrodes 2592 may be provided. If a dummy electrode that is electrically insulated from these is provided between the two, the surface of the region with different transmittance can be This is preferable because it can reduce the volume.

[0239] Next, the touch panel 2000 will be described in detail with reference to FIG. 1 corresponds to a cross-sectional view taken along dashed line X1-X2 in FIG.

[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 a substrate 2590. The insulating layer 2593 covers the electrodes 2591 and 2592, and the adjacent electrodes The electrodes 2591 are electrically connected to each other through wiring 2594. An electrode 2592 is provided therebetween.

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

[0243] The electrodes 2591 and 2592 can be formed, for example, using a conductive material having light-transmitting properties. After forming a film on the substrate 2590 by sputtering, 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 silicone resin. 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 adjacent electrodes 2591 are connected to each other by wiring 2594 formed in a part of the insulating layer 2593. The wiring 2594 is electrically connected to the electrode 2591 and the electrode 259 By using a material with higher conductivity than the material used in 2, the electrical resistance can be reduced. This is preferable because

[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. The wiring 2598 is made of, for example, aluminum. , gold, platinum, silver, nickel, titanium, tungsten, chromium, molybdenum, iron, cobalt Metal materials such as copper and palladium, and alloy materials containing these metal materials can be used. do.

[0247] In addition, the wiring 2598 and the FPC 2509(2) are electrically connected by the terminal 2599. In addition, terminal 2599 is made of various anisotropic conductive films (ACF: Anisotropic Conductive Films). Conductive Film) and Anisotropic Conductive Paste (ACP) For example, a 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 so as to overlap with it via an adhesive layer 2597 . 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 transparent. 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. Xanthene-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 display has a plurality of pixels arranged in a square shape and a driving circuit. Each pixel has a light emitting element and a light emitting and a pixel circuit for driving 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 includes a light emitting element 2550R and a light emitting element 2550R that can supply power to the light emitting element 2550R. The transistor 2502t can be used as a gate driver.

[0253] The transistor 2502t is covered with an insulating layer 2521. Note that the insulating layer 2521 is It has a function of flattening unevenness caused by previously formed transistors, etc. The insulating layer 2521 may be provided with a function of suppressing diffusion of impurities. This is preferable because it can suppress deterioration in the reliability of transistors and the like 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 is emitted in the direction of the arrow shown in the figure through the colored layer 2567R. A light-shielding layer 2567BM is provided at the end of the light-emitting element 2550R and the coloring layer 2567R. There is a sealing layer 2560 between them.

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

[0257] The scanning line driver circuit 2503g includes a transistor 2503t and a capacitor 2503c. In addition, 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 (the scanning line driver circuit 2503g ) 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 The FPC2509(1) has a function to supply 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. A transistor having a structure as shown in FIG. The transistors 502t and 2503t each have a semiconductor layer including 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 such.

[0260] In addition, a top gate transistor different from the bottom gate transistor shown in FIG. A structure in which a transistor of this type is applied to a 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 that occur.

[0261] The touch panel 2000 shown in FIG. 11A is a touch panel that receives light from pixels as shown in FIG. 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. Steam 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 having approximately the same thermal expansion coefficient for these substrates. For example, is 1×10 -3 / K or less, preferably 5×10 -5 / K or less, more preferably 1×10 - 5 / K or less.

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

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

[0265] The colored layer 2567R is located so as to overlap the light emitting element 2550R. The light from the light emitting element 2550R is emitted in the direction in which the transistor 2502t is provided. That is, the light from the light emitting element 2550R (part of it) is transmitted through the colored layer 2567R. The light is emitted in the direction of the arrow shown in the figure. 67BM is provided.

[0266] The touch sensor 2595 is a translator as viewed from the light emitting element 2550R of the display panel 2501. The second resistor 2502t is provided on the side where the first resistor 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 sensor 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 of various structures can be applied to the transistor 2501. In the above, a case where a bottom-gate transistor is applied is shown. As shown in B), a top-gate 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. 13A 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 FIG. 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. FIG. 13A shows a capacitance 2 formed by overlapping an electrode 2621 and an electrode 2622. 603. The electrodes 2621 and 2622 have functions interchangeably. This is also fine.

[0271] The pulse voltage output circuit 2601 is a circuit for applying a pulse voltage to the wirings X1-X6 in sequence. When a pulse voltage is applied to the wiring of X1-X6, a capacitance 2603 is formed. An electric field is generated between the electrodes 2621 and 2622. The electric field generated between these electrodes may cause shielding or the like. This generates a change in the mutual capacitance of the capacitor 2603, and is used to detect 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 of the capacitor 2603. The Y1-Y6 wiring detects the proximity of the object to be detected, or If there is no contact or proximity of the object to be detected, the detected current value does not change. When the mutual capacitance decreases due to contact, a change in the current value is detected. This can be achieved by using an integrating circuit or the like.

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

[0274] A pulse voltage is applied to the wires X1-X6 in sequence, and the wires Y1-Y The waveform in wire 6 changes. When there is no proximity or contact of the object to be sensed, the waveform in wire X1-X6 The waveforms of Y1-Y6 change uniformly according to the change in the voltage of the wiring. At the points where the current flows or comes into contact, the current value decreases, and the corresponding voltage waveform 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 FIG. 13A, only a capacitor 2603 is provided at the intersection of the wiring as a touch sensor. The configuration of a passive type touch sensor has been shown, but an active type with transistors and capacitance can also be used. FIG. 14 shows one sensor included in an active 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 2612. 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 drain of the transistor 2612, and the other is connected to the voltage VSS A signal G1 is applied to the gate of the transistor 2612, and a signal G2 is applied to the source or drain of the transistor 2612. 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 FIG. 14 will be described. First, a transistor is used as a signal G2. 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 due to the proximity or contact of a detection object such as a finger. As the potential of the node n changes from VRES,

[0279] In the read operation, a potential that turns on the transistor 2612 is applied as the signal G1. A current flows through the transistor 2611 in response to the potential of the node n, that is, a current flows through the wiring ML. The current changes. 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 each formed of an oxide semiconductor. 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 increased for a long time. This allows the node n to be supplied with VRES again (lifting This can reduce the frequency of reshuffling.

[0281] This embodiment may be appropriately combined with at least a part of other embodiments described in this specification. It can be implemented together. EXAMPLES

[0282] <Synthesis Example 1> In this example, a heterocyclic compound according to one embodiment of the present invention, 2-[3-(benzo[1,2-b: 4,5-b']bisbenzofuran-6-yl)phenyl]dibenzo[f,h]quinoxal The synthesis method of 2mBbfPDBq (structural formula (101)) will be described. 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 sodium carbonate solution (2.0 mol / L) were added to the flask, and the inside of the flask was reduced in volume. The mixture was degassed by stirring under pressure.

[0285] After degassing, the system was purged with a nitrogen gas stream, and the mixture was heated to 80° C. .69g (0.60mmol) of tetrakis(triphenylphosphine)palladium(0 ) was added and stirred at the same temperature for 2 hours. The mixture was cooled to room temperature and then degassed again under reduced pressure. After placing it under a stream of fresh air, the mixture was heated to 80°C. After heating, 0.69 g (0.60 mm ol) of tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred at the same temperature for 5 hours. Heat for a short period.

[0286] After heating, 2.0 g (14 mmol) of 2-fluorophenylboronic acid was added and the mixture was further stirred at the same temperature. After heating, the mixture was allowed to cool to room temperature, degassed under reduced pressure, and the system was purged with a nitrogen stream. The mixture was heated to 80° C. and 0.64 g (0.55 mmol) of tetrakis(trimethylsilyl) (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 saline. The mixture was washed with ethyl acetate and dried over anhydrous magnesium sulfate. The filtrate was concentrated to obtain a compound. The compound was recrystallized from toluene. The filtrate was concentrated and the compound was purified by column chromatography. When the mixture was purified using a developing solvent of hexane:ethyl acetate=30:1, 0.3% of the target compound was obtained. g, and the total amount of the target compound was 2.8 g, with 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-fluorophenyl) Put (triphenyl)-2,5-dimethoxybenzene into the flask, put the flask under a nitrogen stream, and then 20 mL of dehydrated dichloromethane was added to obtain a solution. This solution was placed in an ice bath and stirred. Add 21 mL (21 mmol) of boron tribromide solution (1 mol / L dichloromethane solution) to the solution. ) diluted with 22 mL of dehydrated dichloromethane was added dropwise, and the resulting solution was then cooled to 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, washed with an aqueous solution of sodium bicarbonate and saturated saline, and The mixture was filtered and the filtrate was concentrated. The synthesis scheme showing the above synthesis method is shown in the following formula (A- 2).

[0291] [ka]

[0292] <Step 3> In a 100 mL three-neck flask, add 2.3 g (7.8 mmol) of the 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 in the flask. The mixture was degassed by stirring while reducing the pressure. After degassing, the system was purged with a nitrogen gas stream, and The mixture was stirred at 200°C for 4.5 hours. After stirring, it was cooled 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 aqueous layer was extracted three times with toluene. The extract and the organic layer were combined to give A solid precipitated, which was then collected by suction filtration. The filtrate was diluted with carbonated water. The mixture was washed with an aqueous sodium chloride solution and saturated saline, and then dried over anhydrous magnesium sulfate. The mixture was naturally filtered, the filtrate was concentrated, and the solid was recrystallized from toluene. The solid product was obtained in an amount of 0.53 g. The solid product was recrystallized from toluene. The total amount of the target solid was 1.5 g (5.7 mmol). The synthesis method was shown in the following formula (A-3). .

[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 to the flask, and the flask was purged with nitrogen. Water and tetrahydrofuran were added, and the resulting solution was stirred at -78°C. 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 the temperature was raised to room temperature and the mixture was 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. Then, diethyl ether 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 with anhydrous magnesium sulfate. The 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 obtain a compound, which was recrystallized from toluene / hexane. The target solid was obtained in an amount of 0.60 g. 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, 50 mg (0.16 mmol) of tris(2-methylphenyl)phosphine, 15 mL of toluene, and 2 mL of ethanol. The flask was then depressurized. The mixture was degassed while stirring.

[0300] After degassing, the flask was purged with a nitrogen gas 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 solid was dissolved in toluene and heated. The resulting solution was filtered through Celite and alumina. The filtrate was concentrated to give The solid was recrystallized from toluene to obtain 1.0 g (1.8 mmol) of the target solid. ), was obtained in 58% yield.

[0301] The resulting solid (1.0 g) 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 argon of 5 mL / min. After sublimation purification, 0.61 g of the target pale yellow solid was obtained, with a recovery rate of 5. The synthesis method was obtained at a yield of 9%. 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 FIG. In Example 1, the heterocyclic compound according to one embodiment of the present invention is represented by the above structural formula (101). It was found that 2mBbfPDBq was obtained.

[0304] 1 H NMR (tetrachloroethane-d2, 500MHz): 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 (K.K. A fluorometer (V550 manufactured by JASCO) was used to measure the emission spectrum. The absorption spectrum of the obtained toluene solution was The results of the measurement 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 and emission spectra of the solid thin film are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity.

[0306] As shown in FIG. 16(A), the toluene solution of 2mBbfPDBq had peaks at 282 nm and 3 An absorption peak is seen around 33 nm, and emission wavelength peaks are seen around 392 nm and 404 nm. In addition, the results of Figure 16(B) show that in the solid thin film of 2mBbfPDBq, Absorption peaks are seen around 63 nm and 337 nm, and an emission wavelength peak is seen around 429 nm. was seen. EXAMPLES

[0307] <Synthesis Example 2> In this example, a heterocyclic compound according to one embodiment of the present invention, 2-[3-(benzo[1,2-b: 5,4-b']bisbenzofuran-6-yl)phenyl]dibenzo[f,h]quinoxal 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. The flask was then degassed by stirring while reducing the pressure inside the flask. 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 h. 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 irradiated with ultrasonic waves. 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, add 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 Add sodium carbonate solution (2 mol / L) and stir while reducing the pressure inside the flask. The mixture was degassed. After degassing, the system was purged with a nitrogen gas stream, 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 cooling the mixture 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 pressure The system was degassed, and the inside of the system was again purged with a nitrogen gas 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 resulting aqueous layer was diluted with toluene. The extract and the organic layer were combined, washed with saturated saline, and then extracted with toluene. 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 product was purified by elution with a gradient of 100% to 100% chloroform, and the desired pale yellow oil was obtained. The compound was obtained in an amount of 0.2g (22mmol) with a yield of 92%. The synthesis scheme showing the above synthesis method is shown below. As 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-fluoro phenyl)-2,4-dimethoxybenzene was added, and the flask was purged with nitrogen. 60 mL of dehydrated dichloromethane was added to obtain a solution. The obtained solution was 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 The mixture was stirred at room temperature for 15 hours. 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 layer and the aqueous layer of the resulting mixture were separated. Extract three times with dichloromethane, combine the resulting extract and the organic layer, and add sodium bicarbonate. After washing with aqueous solution and saturated saline, it was dried over anhydrous magnesium sulfate. The 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 about 7 g (about 22 mmol) of 1,5-dichlorophenyl ether obtained in step 3. -Bis(2-fluorophenyl)-2,4-dihydroxybenzene, 13 g (96 mm ol) of potassium carbonate and 140 mL of N-methyl-2-pyrrolidinone in a flask. The mixture was degassed by stirring while reducing the pressure inside. After degassing, the system was purged with a nitrogen gas stream. The mixture was then 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 oily product. The oily matter obtained was recrystallized from toluene / hexane to give the desired 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 subjected to silica gel column chromatography (eluent: hexane). The product was purified using a solvent-based solvent exchanger (SOx) and recrystallized from hexane to obtain the desired white powdery solid. The white powdery solid was 2.2 g (8.5 mmol) in total, and the two The above synthesis method was obtained in a yield of 39% in each 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, Add 4-b']bisbenzofuran and stir while reducing the pressure inside the flask. After degassing, the system was purged with a nitrogen gas 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. After the addition, the resulting solution was cooled to room 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 aqueous layer was extracted three times with toluene, and the extract and the organic layer were combined and washed 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. The mixture was gravity filtered and the filtrate was concentrated. The solid obtained was recrystallized from toluene / hexane to give the desired light brown solid, 2. The compound was obtained in an amount of 5 g (6.5 mmol) with a yield of 76%. The synthesis scheme showing the above synthesis method is shown below. As 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 hydroxide (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 gas 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 cooled 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 degassed by stirring while reducing the pressure inside the flask.

[0329] After degassing, the system was purged with a nitrogen gas stream and heated to 80°C. After heating, 0.10 g (87 μ mol) of tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred for 1.5 hours. After stirring, the mixture was allowed to cool to room temperature, and the precipitated solid was collected by suction filtration. The solid was collected. The solid was washed with water and ethanol. The solid was dissolved in toluene. The filtrate was concentrated and the solid was separated by filtration through Celite and alumina. The 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 train sublimation. The solid was heated at 310°C for 15.5 h under argon at 2.5 Pa and 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 FIG. In Example 2, the heterocyclic compound according to one embodiment of the present invention is represented by the above structural formula (107). It was found that 2mBbf(II) PDBq was obtained.

[0333] 1 H NMR (tetrachloroethane-d2, 500MHz): 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 The absorption spectrum and emission spectrum of the solid thin film were measured. The was prepared by vacuum deposition on a quartz substrate. A fluorescence spectrometer (V550, manufactured by JASCO Corporation) was used to measure the emission spectrum. A spectrophotometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used. The measurement results of the spectrum and the emission spectrum are shown in FIG. 18(A). The horizontal axis is the wavelength, and the vertical axis is The absorption intensity is shown. The absorption spectrum and emission spectrum of the solid thin film are also shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity.

[0335] From the results of Figure 18(A), in the toluene solution of 2mBbf(II)PDBq, Absorption peaks are seen at around 288 nm and 393 nm, and emission peaks are seen at 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 seen around 265 nm and 384 nm, and around 430 nm. A peak in the emission wavelength was observed. EXAMPLES

[0336] <Synthesis Example 3> In this example, a heterocyclic compound according to one embodiment of the present invention, 2-[3-(benzo[1,2-b: 5,6-b']bisbenzofuran-4-yl)phenyl]dibenzo[f,h]quinoxal We will explain the synthesis method 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-dimethoxy benzene, 7.2 g (51 mmol) of 2-fluorophenylboronic acid, and 66 mL of toluene, 66 mL of diethylene glycol dimethyl ether (diglyme), Add 76 mL of 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 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-fluorobenzenesulfonyl chloride 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 inside of the system under a nitrogen stream, the mixture was stirred at 80° C. for 8 hours. After stirring, the mixture was cooled to room temperature. After cooling to room temperature, 5.2 g (37 mmol) of 2-fluorophenylboronic acid and 0.1 9g (0.46mmol) of 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 system was then purged with nitrogen and the mixture was then degassed. The mixture was stirred at 80° C. for 4 h.

[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, washed with saturated saline, and then extracted with anhydrous sulfuric acid. 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 by gradient from hexane to chloroform, and then toluene was added. The product was recrystallized from hexane to give 8.4 g (36 mmol) of the desired solid. The synthesis method was obtained at a yield of 78%. The synthesis scheme showing the above synthesis method is shown in the following formula (C-1).

[0341] [ka]

[0342] <Step 2> In a 300 mL Erlenmeyer flask, add 8.4 g (36 mmol) of 2'-fluoro- Add 1,3-dimethoxy-2,1'-biphenyl and 130 mL of acetonitrile. 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 then 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 saline, and dry with anhydrous magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to obtain a yellow oil. 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 to step 6. 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-dicyclohexyl Add xylphosphino-2',6'-dimethoxybiphenyl. Do not apply pressure to the flask. 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, cooled to room temperature, and then separated into an organic layer and an aqueous layer. The aqueous layer was extracted three times with toluene, and the resulting extract and the organic layer were combined and washed with saturated saline. The mixture was washed and dried over anhydrous magnesium sulfate. The filtrate obtained by gravity filtration was concentrated. Finally, an oily substance was obtained.

[0347] The oily substance obtained was subjected to silica gel column chromatography (eluent: hexane:ethyl acetate). The product was purified by hexane / toluene (10:1) and recrystallized from toluene / hexane. The mother liquor was concentrated to obtain 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 weight 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-fluorophenyl) (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 70 mmol of L 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 further 40 mL of water was added dropwise. The organic layer and the aqueous layer were separated. The aqueous layer was extracted three times with dichloromethane. The organic layers were combined, washed with aqueous sodium bicarbonate and saturated saline, and then extracted with magnesium sulfate. The mixture was dried over ZnSe. The filtrate obtained by gravity filtration was concentrated to obtain The resulting oily substance was purified by silica gel column chromatography (development). The solvent was hexane:ethyl acetate (8:1), and then recrystallized with hexane / chloroform. The product was crystallized to give 8.7 g (26 mmol) of a white solid 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 eggplant flask, add 8.7 g (26 mmol) of 4-(3-chloro-2-fluorophenyl) 1,3-dihydroxybenzene and g (0.10 mmol) of potassium carbonate and 150 mL of N-methyl-2-pyrrolidinone The mixture was stirred while the inside of the flask was reduced in pressure, and the mixture was degassed. After degassing, the inside of 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, it was allowed to cool to room temperature. Thereafter, toluene, water and hydrochloric acid were added and stirred, and the organic layer and the aqueous layer of the resulting mixture were separated.

[0352] The obtained aqueous layer was extracted three times with toluene, and the obtained extract and the organic layer were combined and diluted with carbonate. Wash with aqueous sodium hydrogen water and saturated saline, and dry with anhydrous magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated to obtain a brown solid. The solid was recrystallized from toluene / hexane, and the first crystal was 3.4 g (12 mmol). ), and 1.6 g (5.4 mmol) of the second crystal, the combined yield of the first and second crystals 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 inside of 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 incubated 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 train sublimation. 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 FIG. In Example 3, the heterocyclic compound according to one embodiment of the present invention is represented by the above structural formula (149). It was found that 2mBbf(III)PDBq was obtained.

[0360] 1 H NMR (tetrachloroethane-d2, 500MHz): 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 and in solid thin films were The absorption spectrum and emission spectrum were measured. The film was prepared by vacuum deposition on a quartz substrate. A fluorescent spectrometer (V550 model, manufactured by JASCO Corporation) was used to measure the emission spectrum. A spectrophotometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used. The measurement results of the absorption spectrum and the emission spectrum are shown in FIG. The absorption and emission spectra of the solid thin film are shown in the table 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 seen at around 376 nm and 394 nm, and emission peaks are seen at around 407 nm. A peak in wavelength was observed. Also, from the results in Figure 20(B), 2mBbf(III) PDB In the solid thin film of q, absorption peaks are seen around 266 nm and 384 nm, and A peak in the emission wavelength was observed near the EXAMPLES

[0363] <Synthesis Example 4> In this example, a heterocyclic compound according to one embodiment of the present invention, 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 described. 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 gas stream and the mixture was heated to 80° C. 10 mg (45 μmol) of palladium(II) acetate was added to the mixture and 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 paraacetate was added. Then, sodium(II) was added and 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 mmol) of the target light brown solid was obtained. l) was obtained in a yield of 86%.

[0367] The resulting solid (1.49 g) was purified by train sublimation. The solid was heated at 350°C under a pressure of 5.1 Pa and a flow rate of argon 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 FIG. In Example 4, the heterocyclic compound according to one embodiment of the present invention represented by the above structural formula (150) is It was found that 2mBbf(III)BPDBq was obtained.

[0370] 1 H NMR (tetrachloroethane-d2, 500MHz): 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 and in solid thin films were The absorption spectrum (hereinafter simply referred to as the "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. The emission spectrum was measured using A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used. The measurement results of the absorption spectrum and the emission spectrum are shown in FIG. The axis represents the absorption intensity. The absorption and emission spectra of solid thin films are also shown. is shown in Figure 22(B). The horizontal axis represents wavelength and the vertical axis represents absorption intensity.

[0372] From the results of FIG. 22(A), in the toluene solution of 2mBbf(III)BPDBq, 264 Absorption peaks were observed at 391 nm and 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. EXAMPLES

[0373] In this example, a heterocyclic compound according to one embodiment of the present invention, 2mBbfPDBq (structural formula (10 1)) was used as the light-emitting device 1, 2mBbf(II)PDBq (structural formula (107)) was used as the light-emitting device 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)). For comparison, 2mDBTBPDBq- A comparative light-emitting element 5 was fabricated using the light-emitting element 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 Elements 5> First, indium tin oxide (ITO) containing silicon oxide is sputtered on a glass substrate 900. A first electrode 901 that 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 substrate surface 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 has been reduced in pressure to about Pa. After performing vacuum baking at 170° C. for 30 minutes in a heating chamber in the apparatus, the substrate 900 is 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 embodiment, 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 implantation layer 915 is formed sequentially will be described.

[0380] 10 minutes inside the vacuum chamber -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4- DBT3P-II: Molybdenum oxide was co-evaporated at a ratio of 4:2 (mass ratio) onto the first electrode 901. The deposition layer 911 was formed. The thickness of the layer was set to 20 nm. This is a deposition method in which different evaporation sources are evaporated 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 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 The material was co-evaporated in a ratio of 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.

[0384] In the case of light-emitting element 2, 2-[3-(benzo[1,2-b:5,4-b']bisbenzofura 2mBbf(II) PDBq), PCBBiF, [Ir(tBuppm)2(acac)], 2mBbf( II)PDBq:PCBBiF:[Ir(tBuppm)2(acac)]=0.7:0 The mixture was co-evaporated in a ratio of 0.3:0.05 (mass ratio) to form a film with a thickness of 20 nm. 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 thickness of 40 nm.

[0386] In the case of the 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 to a thickness of 40 nm by vapor deposition. 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) was co-evaporated to form a film with a thickness of 20 nm, and then 2mDBTBPDBq -II:PCBBiF:[Ir(tBuppm)2(acac)]=0.8:0.2:0 The laminated structure was formed by co-evaporating the material so that the ratio of the layers was 0.05 (mass ratio) and forming a film with a thickness of 20 nm. The light emitting layer 913 having the above structure was formed to a thickness of 40 nm.

[0388] Next, in the case of the light-emitting element 1, 2mBbfPDBq is deposited to a thickness of 20 nm on the light-emitting layer 913. In the case of light-emitting element 2, 2000 μmBbf(II)PDBq was deposited on the substrate. After evaporating 10 nm of Bphen, the light-emitting element 3 was evaporated to 2 mBbf (III ) After depositing 20 nm of PDBq, deposit 10 nm of Bphen. After evaporating 20 nm of mBbf(III)BPDBq, 10 nm of Bphen was evaporated. An electron transport layer 914 was formed on each of them.

[0389] Further, lithium fluoride was evaporated 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 is evaporated onto the electron injection layer 915 to a thickness of 200 nm, and then a cathode is formed. 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 performed 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 not exposed to the air. The device was sealed in a glove box with a nitrogen atmosphere (sealing material was applied around the device). , UV treatment during sealing, and heat treatment at 80℃ for 1 hour.

[0394] <Operation Characteristics of Light-Emitting Element 1 to Light-Emitting Element 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 current density vs. luminance characteristics of the light-emitting elements 1 to 4, and FIG. 25 shows voltage vs. 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 in the vicinity The main initial characteristics of the light-emitting element 4 and the comparative light-emitting element 5 are shown in Table 2 below. The initial characteristics were confirmed to be as good as those of the light-emitting elements 1 to 4.

[0397] [Table 2]

[0398] Furthermore, the light-emitting elements 1 to 4 were supplied with 25 mA / cm 2 Light emission when a current is applied at a current density of The emission spectra of the light-emitting elements 1 to 4 are shown in FIG. 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)]. In addition, for the comparative light-emitting element 5, similarly to the light-emitting elements 1 to 4, [Ir(tBu The emission spectrum was confirmed to be due to the green emission of 2(acac)].

[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 operation time (h) of the element. The reliability test was performed with an initial luminance of 5000cd / 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. As can be seen from the results shown in FIG. 29, all the light-emitting elements exhibit high reliability. Therefore, by using the heterocyclic compound of one embodiment of the present invention, a light-emitting element can have a long lifetime. It can be seen that.

[0401] In addition, a storage test was performed 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 for a specified period of time. After the test, the operating characteristics were measured. The experiment was carried out in an atmosphere maintained at 0.4 °C.

[0402] FIG. 30 shows the change over time in the appearance of the light-emitting elements 1 to 3 and the comparative light-emitting element 5. As a result, the light-emitting elements 1 to 10 which are embodiments of the present invention were 3 has good heat resistance, maintaining the initial external quantum efficiency even after long-term storage at 100°C. 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 The molecular weight of both PDBq and 2mBbf(III)PDBq used in light-emitting element 3 is 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 had 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 large difference in thermal stability.

[0404] Between the light-emitting element 1 to the light-emitting element 3 and the comparative light-emitting element 5, 3 has a molecular structure characterized by the presence of a condensed aromatic ring, benzobisbenzofuran. The difference in heat resistance observed in the storage test is due to this molecular structure, and the molecular weight 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 condensed rings is very effective. EXAMPLES

[0405] In this example, a heterocyclic compound according to one embodiment of the present invention, 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 Co., Ltd., 99.8%, Catalog No. 227 056) was used as the supporting electrolyte, 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 The counter electrode (5 cm) was used as the reference electrode, and Ag / Ag + Electrode (B.A.S. The measurements were performed at room temperature (20 to 2 The scan speed 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, 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 formula =-4.94-Ec, the HOMO and LUMO levels can be calculated. In addition, the CV measurement was repeated 100 times, and the oxidation rate at the 100th cycle was The electrical stability of the compound was examined by comparing the first cycle oxidation-reduction wave with the first cycle reduction-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 from 1.5 eV to 1.5 eV. On the other hand, the LUMO level was -2.97 eV. In addition, the redox wave was repeatedly measured at 10 The redox wave after the 0th cycle peaked at 73% of the redox wave after the 1st cycle. The strength of the 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 (Bruker AXS, T G-DTA2410SA) was used. At normal pressure, temperature rise rate of 10℃ / min, under nitrogen gas flow (flow rate When the measurement was performed under the condition of 200 mL / min, the relationship between weight and temperature (thermogravimetry) was The 5% weight loss temperature of 2mBbfPDBq was about 442°C. The heat resistance of fPDBq was shown to be good.

[0410] Differential scanning calorimetry (DSC) was performed using a PerkinElmer Pyris1 DSC. The differential scanning calorimetry was performed at a heating rate of 50°C / min from -10°C to 3°C. After heating to 70℃, hold at that temperature for 1 minute, then cool to -10℃ at a rate of 50℃ / min. The cooling operation was performed 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 has the following properties.

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

[0412] For LC / MS analysis, LC (liquid chromatography) separation was performed using Waters Acqui 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 any 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 the measurement, The ratio of mobile phase A to mobile phase B in the analysis was 95:5. The total time was 10 minutes. 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 + ], 2mBbfPDBq theoretical value = Next, the ion with a mass-to-charge ratio (m / z) of 563.175 was detected. (Precursor ions) are collided with argon gas in a collision cell to dissociate them. The energy when the precursor ion collides with argon (collision energy The energy (energy) was set to 50 eV and 70 eV. The collision of the precursor ion with argon gas The collision energy of the product ions generated was 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 in 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 at around m / z=177.070. From the results of Figure 32, in the measurement with a collision energy of 70 eV, the compound represented by the structural formula (101) The 2mBbfPDBq is mainly located around m / z=305.096 and m / z=229. The product images were obtained around m / z=077, m / z=202.066, and m / z=176.063. It was found that the on-state was detected. Note that 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 is important data for identifying fPDBq.

[0417] The product ion at m / z=536.165 has the structure shown in formula (a) below. 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 above. 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 As shown in the structural formula (101), the compound is substituted at the 2-position of dibenzo[f,h]quinoxaline. The bond cleavage produced 6-phenylbenzo[1,2-b:4,5-b']bisbenzofuran. The product ion at m / z=305.096 is assumed to be derived from the orchid. As shown in (d), 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 give 2-phenyldibenzo[f,h] The product ion at m / z=229.076 is assumed 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 produced 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 in the following formula (g). As shown in the figure, 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 a 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 in identifying 2mBbfPDBq contained in a mixture. This can be said to be essential data.

[0418] [ka] EXAMPLES

[0419] In this example, a heterocyclic compound according to one embodiment of the present invention, 2-[ 3-(benzo[1,2-b:5,4-b']bisbenzofuran-6-yl)phenyl]di HOMO levels of benzo[f,h]quinoxaline (abbreviation: 2mBbf(II)PDBq) 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 measured by cyclic voltammetry. The calculation was based on the CV measurement. The CV measurement method and the HOMO and LUMO The method of 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 after the first cycle. % peak intensity, indicating resistance to reduction of 2mBbf(II)PDBq 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: EXAMPLES

[0424] In this example, a heterocyclic compound according to one embodiment of the present invention, 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 measured by cyclic voltammograms. The calculation was based on the CV measurement. The CV measurement method, HOMO level and LUM The method of 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, the measurement No clear oxidation peak was obtained in the range of 0 eV to 1.5 eV. The O level was found to be -2.95 eV. In addition, the repeated measurement of the oxidation-reduction wave The oxidation-reduction wave after 100 cycles was 79% smaller than that of 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 thermal stability of 2mBbf(III)PDBq was about 454°C. It has been shown that there is. EXAMPLES

[0429] In this example, a heterocyclic compound according to one embodiment of the present invention, 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 measured 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 voltammetry. The calculation was based on the CV measurement. The CV measurement method, HOMO level and LU The calculation method of the MO level is the same 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 range of 0.1 eV to 1.5 eV. The LUMO level was found to be -2.98 eV. In the experiment, the oxidation-reduction wave after 100 cycles was The peak intensity was maintained at 71%, indicating that the reduction of 2mBbf(III)BPDBq It was confirmed that the resistance to the [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) EL layer (n-1) 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 Insulation 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 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Emitting layer 914 Electron transport layer 915 Electron injection layer 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 Insulating layer 2528 Insulator 2550R Light emitting element 2560 Sealing layer 2567BM light shielding layer 2567p anti-reflection layer 2567R colored layer 2570 PCB 2590 Board 2591 Electrode 2592 Electrode 2593 Insulation layer 2594 Wiring 2595 Touch Sensor 2597 Adhesive layer 2598 Wiring 2599 Terminal 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 Substrate 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 Substrate 4202 Light emitting element 4204 Electrode 4205 EL layer 4206 Electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 4300 Lighting Equipment 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rear view mirror 7100 Television equipment 7101 Case 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 Case 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 Case 7402 Display section 7403 Operation button 7404 External connection part 7405 Speaker 7406 Mike 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 Case

Claims

1. A compound represented by the following formula: 【Chemistry 1】

2. A compound represented by the following formula: 【Chemistry 2】

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