WO2017068457A1 - Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device - Google Patents

Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device Download PDF

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Publication number
WO2017068457A1
WO2017068457A1 PCT/IB2016/056067 IB2016056067W WO2017068457A1 WO 2017068457 A1 WO2017068457 A1 WO 2017068457A1 IB 2016056067 W IB2016056067 W IB 2016056067W WO 2017068457 A1 WO2017068457 A1 WO 2017068457A1
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Prior art keywords
light
heterocyclic compound
formula
carbon atoms
substituted
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English (en)
French (fr)
Inventor
Sachiko Kawakami
Yoshimi ISHIGURO
Tatsuyoshi TAKAHASHI
Takao Hamada
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Semiconductor Energy Laboratory Co Ltd
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Semiconductor Energy Laboratory Co Ltd
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Priority to KR1020187013529A priority Critical patent/KR20180067641A/ko
Priority to CN201680061311.6A priority patent/CN108137565B/zh
Priority to CN202210143447.9A priority patent/CN114436940B/zh
Priority to KR1020247018576A priority patent/KR20240094035A/ko
Publication of WO2017068457A1 publication Critical patent/WO2017068457A1/en
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/129—Chiplets
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays

Definitions

  • One embodiment of the present invention relates to an object, a method, and a manufacturing method.
  • the present invention relates to a process, a machine, manufacture, or a composition of matter.
  • one embodiment of the present invention relates to a semiconductor device, a light-emitting device, a display device, a lighting device, a light-emitting element, or a manufacturing method thereof.
  • one embodiment of the present invention relates to a heterocyclic compound and a novel method for synthesizing the heterocyclic compound.
  • one embodiment of the present invention relates to a light-emitting element, a light-emitting device, an electronic device, and a lighting device that include the heterocyclic compound. Note that one embodiment of the present invention is not limited to the above technical field.
  • a light-emitting element using an organic compound as a luminous body which has features such as thinness, lightness, high-speed response, and DC drive at low voltage, is expected to be applied to a next-generation flat panel display.
  • a display device in which light-emitting elements are arranged in matrix is, in particular, considered to have advantages in a wide viewing angle and excellent visibility over a conventional liquid crystal display device.
  • the light emission mechanism of a light-emitting element is as follows: when a voltage is applied between a pair of electrodes with an EL layer including a luminous body provided therebetween, electrons injected from the cathode and holes injected from the anode recombine in the light emission center of the EL layer to form molecular excitons, and energy is released and light is emitted when the molecular excitons relax to the ground state.
  • a singlet excited state and a triplet excited state are known as excited states, and it is thought that light emission can be achieved through either of the excited states.
  • An organic compound is mainly used in an EL layer in such a light-emitting element and greatly affects an improvement in the characteristics of the light-emitting element. For this reason, a variety of novel organic compounds have been developed (e.g., see Patent Document 1).
  • Patent Document 1 Japanese Published Patent Application No. 2007-189001
  • an object of one embodiment of the present invention is to provide a novel heterocyclic compound.
  • an object of one embodiment of the present invention is to provide a novel heterocyclic compound which can improve the element characteristics of a light-emitting element.
  • An object of one embodiment of the present invention is to provide a novel light-emitting element with high emission efficiency and high heat resistance.
  • An object of one embodiment of the present invention is to provide a novel heterocyclic compound that can be used in a light-emitting element.
  • An object of one embodiment of the present invention is to provide a novel heterocyclic compound that can be used in an EL layer of a light-emitting element.
  • An object of one embodiment of the present invention is to provide a novel light-emitting element.
  • An object of one embodiment of the present invention is to provide a novel light-emitting device, a novel electronic device, or a novel lighting device. Note that the descriptions of these objects do not disturb the existence of other objects. In one embodiment of the present invention, there is no need to achieve all of these objects. Other objects will be apparent from and can be derived from the description of the specification, the drawings, the claims, and the like.
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • DBq represents a substituted or unsubstituted dibenzo
  • n is 0 or 1.
  • Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G2-1).
  • any one of R 18 to R 20 represents a substituent represented by General
  • Each of the other two of R to R and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G3-1).
  • any one of R 27 and R 28 represents a substituent represented by General
  • Each of the other of R and R and R and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Z represents oxygen, sulfur, or nitrogen. When Z represents nitrogen, a substituent or no substituent may be bonded at the Z-position.
  • DBq represents a substituted or unsubstituted dibenzo
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • the skeleton represented by General Formula (G3-1) is referred to as a dibenzofuran skeleton or a dibenzofuranyl group when Z represents oxygen, is referred to as a dibenzothiophenyl skeleton or a dibenzothiophenyl group when Z represents sulfur, and is referred to as a carbazole skeleton or a carbazolyl group when Z represents nitrogen.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G4-1).
  • any one of R , R , and R represents a substituent represented by
  • G4-2 represented by General Formula (G4-2) is not bonded, R , and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • DBq represents a substituted or unsubstituted dibenzo
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G5-1).
  • any one of R 27 and R 28 represents a substituent represented by General
  • Each of the other of R and R and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Z represents oxygen, sulfur, or nitrogen. When Z represents nitrogen, a substituent or no substituent may be bonded at the Z-position.
  • each of R 11 to R 19 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • n is 0 or 1.
  • Ar 1 , Ar 2 , Ar 3 , and Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-1).
  • DBq represents a substituted or unsubstituted dibenzo
  • Z represents oxygen or sulfur.
  • R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-1) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-1) in which the site of substitution of DBq is a meta-position and the site of substitution of a dibenzothiophenyl group or a dibenzofuranyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-2).
  • DBq represents a substituted or unsubstituted dibenzo
  • Z represents oxygen or sulfur.
  • R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-3).
  • DBq represents a substituted or unsubstituted dibenzo
  • R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-3) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-3) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-4).
  • DBq represents a substituted or unsubstituted dibenzo
  • R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-5).
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-5) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-5) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-6).
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-7).
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-7) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-7) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-8).
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G7-1).
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • R 11 to R 19 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G7-1) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G7-1) in which the site of substitution of DBq is a meta-position and the site of substitution of A is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G7-2).
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • R 11 to R 19 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-1).
  • Z represents oxygen or sulfur.
  • R 11 to R 19 , R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-1) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-1) in which the site of substitution of DBq is a meta-position and the site of substitution of a dibenzothiophenyl group or a dibenzofuranyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-2).
  • Z represents oxygen or sulfur.
  • R 11 to R 19 , R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-3).
  • each of R 11 to R 19 , R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-3) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-3) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-4).
  • each of R 11 to R 19 , R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-5).
  • each of R 11 to R 19 , R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-5) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-5) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-6).
  • each of R 11 to R 19 , R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-7).
  • each of R 11 to R 19 , R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-7) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-7) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-8).
  • each of R 11 to R 19 , R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-1).
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-2).
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-3).
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-4).
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-5).
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (GlO-1).
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-2).
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-3).
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-4).
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-5).
  • Another embodiment of the present invention is a light-emitting element including a compound in which a dibenzo
  • Another embodiment of the present invention is a light-emitting element including, in a light-emitting layer, a light-emitting material and a compound in which a dibenzo[/ ⁇ ]quinoxaline ring and a hole-transport skeleton are bonded through a terphenylene group.
  • the hole-transport skeleton may include a ⁇ -electron rich heteroaromatic ring.
  • the ⁇ -electron rich heteroaromatic ring may be a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.
  • Another embodiment of the present invention is a light-emitting element that includes a heterocyclic compound of one embodiment of the present invention and an electrode.
  • Another embodiment of the present invention is a light-emitting element that includes, in a light-emitting layer, a light-emitting substance and a heterocyclic compound of one embodiment of the present invention.
  • Another embodiment of the present invention is a light-emitting device that includes a light-emitting portion including a light-emitting element of one embodiment of the present invention, and a substrate.
  • Another embodiment of the present invention is an electronic device that includes a display portion including the light-emitting device of one embodiment of the present invention, and an antenna, a battery, a housing, a speaker, a microphone, or an operation key.
  • Another embodiment of the present invention is a lighting device that includes a light-emitting device of one embodiment of the present invention, and a housing, a connection terminal, or a protective cover.
  • a novel heterocyclic compound can be provided.
  • a novel heterocyclic compound which can improve the element characteristics of a light-emitting element can be provided.
  • a novel light-emitting element with high emission efficiency and high heat resistance can be provided.
  • a novel heterocyclic compound that can be used in a light-emitting element can be provided.
  • a novel heterocyclic compound that can be used in an EL layer of a light-emitting element can be provided.
  • a novel light-emitting element can be provided.
  • a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided.
  • FIGS. lA and IB are schematic views of light-emitting elements.
  • FIGS. 2 A and 2B are schematic views of an active matrix light-emitting device.
  • FIGS. 3 A and 3B are schematic views of active matrix light-emitting devices.
  • FIG. 4 is a schematic view of an active matrix light-emitting device.
  • FIGS. 5 A and 5B are schematic views of a passive matrix light-emitting device.
  • FIGS. 6Ato 6D illustrate electronic devices.
  • FIG. 7 illustrates a light source device
  • FIG. 8 illustrates a lighting device
  • FIG. 9 illustrates a lighting device and an electronic device.
  • FIG. 10 illustrates in-vehicle display devices and lighting devices.
  • FIGS. 11 A and 11B show NMR charts of 2mDBtTPDBq-II.
  • FIG. 12 shows an absorption spectrum of a solution of 2mDBtTPDBq-II.
  • FIG. 13 shows an emission spectrum of a solution of 2mDBtTPDBq-II.
  • FIG. 14 shows an absorption spectrum of a thin film of 2mDBtTPDBq-II.
  • FIG. 15 shows an emission spectrum of a thin film of 2mDBtTPDBq-II.
  • FIG. 16 shows a phosphorescence spectrum of 2mDBtTPDBq-II.
  • FIGS. 17A and 17B show NMR charts of 2DBtTPDBq.
  • FIG. 18 shows an absorption spectrum of a solution of 2DBtTPDBq.
  • FIG. 19 shows an emission spectrum of a solution of 2DBtTPDBq.
  • FIG. 20 shows an absorption spectrum of a thin film of 2DBtTPDBq.
  • FIG. 21 shows an emission spectrum of a thin film of 2DBtTPDBq.
  • FIG. 22 shows a phosphorescence spectrum of 2DBtTPDBq.
  • FIGS. 23 A and 23B show NMR charts of 2DBtTPDBq-03.
  • FIG. 24 shows an absorption spectrum of a solution of 2DBtTPDBq-03.
  • FIG. 25 shows an emission spectrum of a solution of 2DBtTPDBq-03.
  • FIG. 26 shows an absorption spectrum of a thin film of 2DBtTPDBq-03.
  • FIG. 27 shows an emission spectrum of a thin film of 2DBtTPDBq-03.
  • FIG. 28 shows a phosphorescence spectrum of 2DBtTPDBq-03.
  • FIGS. 29 A and 29B show NMR charts of 2DBtTPDBq-02.
  • FIG. 30 shows an absorption spectrum of a solution of 2DBtTPDBq-02.
  • FIG. 31 shows an emission spectrum of a solution of 2DBtTPDBq-02.
  • FIG. 32 shows an absorption spectrum of a thin film of 2DBtTPDBq-02.
  • FIG. 33 shows an emission spectrum of a thin film of 2DBtTPDBq-02.
  • FIG. 34 shows a phosphorescence spectrum of 2DBtTPDBq-02.
  • FIGS. 35A and 35B show NMR charts of 2DBtTPDBq-04.
  • FIG. 36 shows an absorption spectrum of a solution of 2DBtTPDBq-04.
  • FIG. 37 shows an emission spectrum of a solution of 2DBtTPDBq-04.
  • FIG. 38 shows an absorption spectrum of a thin film of 2DBtTPDBq-04.
  • FIG. 39 shows an emission spectrum of a thin film of 2DBtTPDBq-04.
  • FIG. 40 shows a phosphorescence spectrum of 2DBtTPDBq-04.
  • FIGS. 41 A and 41B show NMR charts of 2mDBtQPDBq-II.
  • FIG. 42 shows an absorption spectrum of a thin film of 2mDBtQPDBq-II.
  • FIG. 43 shows an emission spectrum of a thin film of 2mDBtQPDBq-II.
  • FIG. 44 shows a phosphorescence spectrum of 2mDBtQPDBq-II.
  • FIGS. 45 A and 45B show NMR charts-(3'-chloro-l,l'-biphenyl-4-yl)-9-phenyl-9H-carbazole.
  • FIGS. 46A and 46B show NMR charts of 2mmpPCTPDBq.
  • FIG. 47 shows an absorption spectrum of a solution of 2mmpPCTPDBq.
  • FIG. 48 shows an emission spectrum of a solution of 2mmpPCTPDBq.
  • FIG. 49 shows an absorption spectrum of a thin film of 2mmpPCTPDBq.
  • FIG. 50 shows an emission spectrum of a thin film of 2mmpPCTPDBq.
  • FIG. 51 shows a phosphorescence spectrum of 2mmpPCTPDBq.
  • FIGS. 52A and 52B show MR charts of 2mPCBPDBq.
  • FIG. 53 shows results of reliability tests performed on light-emitting elements 1 to 6 and a comparative light-emitting element 8.
  • FIG. 54 shows results of reliability tests performed on a light-emitting element 9 and a comparative light-emitting element 10.
  • FIG. 55 shows evaluation results of therm ophysical properties of light-emitting elements.
  • ordinal numbers such as “first”, “second”, and “third” are used for convenience and do not denote the order of steps or the stacking order of layers. Therefore, for example, description can be made even when “first” is replaced with “second” or “third”, as appropriate.
  • the ordinal numbers in this specification and the like are not necessarily the same as those which specify one embodiment of the present invention.
  • color is defined by three aspects of hue (corresponding to the wavelength of light of a single color), chroma (saturation, i.e., the degree to which it differs from white), and value (brightness, i.e., the intensity of light).
  • hue corresponding to the wavelength of light of a single color
  • chroma saturated, i.e., the degree to which it differs from white
  • value blueness, i.e., the intensity of light
  • color may be defined by only one of the above three aspects or two of the aspects which are selected arbitrarily.
  • a difference between two colors of light means a difference in at least one of the above three aspects and includes a difference in the shapes of two spectra of light or in the distributions of the relative intensity of the peaks in the spectra.
  • film and “layer” can be interchanged with each other depending on the case or circumstances.
  • conductive layer can be changed into the term “conductive film” in some cases
  • insulating film can be changed into the term “insulating layer” in some cases.
  • One embodiment of the present invention is a heterocyclic compound represented by General Formula (Gl).
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • DBq represents a substituted or unsubstituted dibenzo
  • n is 0 or 1.
  • Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G2-1).
  • the heterocyclic compound is useful in terms of simplicity of the synthesis and synthesis cost.
  • any one of R 18 to R 20 represents a substituent represented by General
  • Each of the other two of R to R and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G3-1).
  • any one of R 27 and R 28 represents a substituent represented by General
  • Each of the other of R and R and R and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Z represents oxygen, sulfur, or nitrogen. When Z represents nitrogen, a substituent or no substituent may be bonded at the Z-position.
  • DBq represents a substituted or unsubstituted dibenzo
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G4-1).
  • any one of R , R , and R represents a substituent represented by
  • G4-2 represented by General Formula (G4-2) is not bonded, R , and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • DBq represents a substituted or unsubstituted dibenzo
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G5-1).
  • the heterocyclic compound is useful in terms of simplicity of the synthesis and synthesis cost.
  • any one of R 27 and R 28 represents a substituent represented by General
  • Each of the other of R and R and R to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Z represents oxygen, sulfur, or nitrogen. When Z represents nitrogen, a substituent or no substituent may be bonded at the Z-position.
  • each of R 11 to R 19 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • n is 0 or 1.
  • Each of Ar 1 to Ar 4 independently represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
  • the adjacent arylene groups may be bonded to each other to form a ring.
  • the fluorene skeleton may have a substituent.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-1).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • Z represents oxygen or sulfur.
  • R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-1) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-1) in which the site of substitution of DBq is a meta-position and the site of substitution of a dibenzothiophenyl group or a dibenzofuranyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-2).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • Z represents oxygen or sulfur.
  • R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-3).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-3) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-3) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-4).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-5).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-5) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-5) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-6).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-7).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • R , 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-7) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G6-7) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G6-8).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • DBq represents a substituted or unsubstituted dibenzo
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Each of R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G7-1).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • R 11 to R 19 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G7-1) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G7-1) in which the site of substitution of DBq is a meta-position and the site of substitution of A is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G7-2).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • A represents any of a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
  • R 11 to R 19 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-1).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • Z represents oxygen or sulfur.
  • R 11 to R 19 , R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-1) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-1) in which the site of substitution of DBq is a meta-position and the site of substitution of a dibenzothiophenyl group or a dibenzofuranyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-2).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • Z represents oxygen or sulfur.
  • R 11 to R 19 , R 21 to R 27 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-3).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • each of R 11 to R 19 , R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-3) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-3) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-4).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • each of R 11 to R 19 , R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-5).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • each of R 11 to R 19 , R 32 to R 36 , R 38 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-5) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-5) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-6).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-7).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • each of R 11 to R 19 , R 32 to R 37 , R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64 independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-7) in which the site of substitution of DBq is a meta-position.
  • Another embodiment of the present invention is the heterocyclic compound represented by General Formula (G8-7) in which the site of substitution of DBq is a meta-position and the site of substitution of a carbazolyl group is a para-position.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G8-8).
  • the heterocyclic compound is useful in terms of a high carrier-transport property and high reliability.
  • each of R 11 to R 19 , R 32 to R 37 R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • R 31 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-1).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-2).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-3).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-4).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G9-5).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Z represents oxygen or sulfur
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (GlO-1).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-2).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-3).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-4).
  • the heterocyclic compound is useful in terms of a high carrier-transport property, high heat resistance, and high reliability.
  • Another embodiment of the present invention is a heterocyclic compound represented by General Formula (G10-5).
  • the heterocyclic compound is useful in terms of a high Tl level, a high carrier-transport property, high heat resistance, and high reliability.
  • Formulae (S01) to (S25) represent specific examples of R 11 to R 19 , R 21 to R 27 , R 32 to R 39 , R 41 to R 44 , R 51 to R 54 , and R 61 to R 64
  • Formulae (S02) to (S25) represent specific examples of R 31
  • Formulae (S31) to (S46) represent examples of Ar 1 to Ar 4 . Note that one embodiment of the present invention is not limited to the examples below.
  • heterocyclic compounds of embodiments of the present invention are shown below. Note that heterocyclic compounds of embodiments of the present invention are not limited to the examples below.

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