WO2014083785A1 - Compound having phenanthroacridan ring structure and organic electroluminescence element - Google Patents

Compound having phenanthroacridan ring structure and organic electroluminescence element Download PDF

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WO2014083785A1
WO2014083785A1 PCT/JP2013/006644 JP2013006644W WO2014083785A1 WO 2014083785 A1 WO2014083785 A1 WO 2014083785A1 JP 2013006644 W JP2013006644 W JP 2013006644W WO 2014083785 A1 WO2014083785 A1 WO 2014083785A1
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substituent
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紀昌 横山
寛史 大熊
秀一 林
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保土谷化学工業株式会社
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    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/12—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 chain containing hetero atoms as chain links
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    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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Definitions

  • the present invention relates to a compound suitable for an organic electroluminescence element which is a self-luminous element suitable for various display devices, and to the element, and more specifically, a compound having a phenanthracridan ring structure, and the compound.
  • the present invention relates to an organic electroluminescence element used.
  • organic electroluminescence elements are self-luminous elements, they have been actively researched because they are brighter and more visible than liquid crystal elements, and can display clearly.
  • organic electroluminescence elements using organic materials practical by developing a laminated structure element that shares various roles with each material. They are composed of a phosphor capable of transporting electrons, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ) and an aromatic amine compound capable of transporting holes, Was injected into the phosphor layer to emit light, whereby high luminance of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
  • Non-Patent Document 2 An element utilizing light emission by thermally activated delayed fluorescence (TADF) has also been developed.
  • TADF thermally activated delayed fluorescence
  • the light emitting layer can be prepared by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound or a material emitting delayed fluorescence.
  • a charge transporting compound generally called a host material
  • a fluorescent compound generally called a fluorescent compound
  • a phosphorescent compound or a material emitting delayed fluorescence.
  • the light injected from both electrodes recombines in the light emitting layer to obtain light emission.
  • Improve the probability of recombination of holes and electrons by increasing the hole injection property and blocking the electron injected from the cathode, and further confine excitons generated in the light emitting layer
  • high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.
  • the heat resistance and amorphous nature of the material are important for the lifetime of the element.
  • thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated.
  • the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.
  • NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
  • Amine derivatives have been known (see, for example, Patent Document 1 and Patent Document 2).
  • NPD has a good hole transport capability, but its glass transition point (Tg), which is an index of heat resistance, is as low as 96 ° C., and device characteristics are degraded due to crystallization under high temperature conditions (for example, Non-patent document 4).
  • a phenanthroacridan derivative represented by the following formula (for example, Compound C) is known, but a phenanthroacridan ring structure having a hole transporting property is known.
  • the compound which has was not known (for example, refer patent document 5).
  • JP-A-8-48656 Japanese Patent No. 3194657 WO2006 / 033563 publication WO2007 / 110228 publication WO2012 / 093861
  • the object of the present invention is as a highly efficient and durable organic electroluminescent device material, excellent in hole injection / transport performance, electron blocking ability, high stability in a thin film state, and heat resistance It is another object of the present invention to provide an organic compound having excellent characteristics and to provide an organic electroluminescence device having high luminous efficiency and durability using this compound.
  • the physical characteristics that the organic compound to be provided by the present invention should have include (1) good hole injection characteristics, (2) high hole mobility, and (3) electron blocking ability. (4) The thin film state is stable, and (5) The heat resistance is excellent.
  • the physical characteristics of the organic electroluminescent device to be provided by the present invention include (1) high luminous efficiency and power efficiency, (2) low emission start voltage, and (3) practical use. The drive voltage is low.
  • the present inventors are expected to have high hole mobility due to the planarity of the phenanthroacridan ring structure and to have excellent electron blocking properties.
  • a compound having a phenanthroacridan ring structure is designed and chemically synthesized. As a result of prototyping a luminescence element and intensively evaluating the characteristics of the element, the present invention has been completed.
  • the present invention is a compound having a phenanthroacridan ring structure represented by the following general formula (1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond
  • B represents a substituted group
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups
  • R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon.
  • 1 to 1 atom 6 linear or branched alkyl groups optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms
  • a straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent
  • R 14 and R 15 may be the same or different from each other.
  • a substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • this invention is a compound which has the phenanthroacridan ring structure of said 1) description represented by the following general formula (1a).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond
  • B represents a substituted group
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups
  • R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon.
  • 1 to 1 atom 6 linear or branched alkyl groups optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms
  • a straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent
  • R 14 and R 15 may be the same or different from each other.
  • a substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • this invention is a compound which has the phenanthroacridan ring structure of said 1) represented by the following general formula (1b).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond
  • B represents a substituted group
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups
  • R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon.
  • 1 to 1 atom 6 linear or branched alkyl groups optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms
  • a straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent
  • R 14 and R 15 may be the same or different from each other.
  • a substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 1) represented by the following general formula (1-1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond
  • B represents a substituted group
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups
  • R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon.
  • 1 to 1 atom 6 linear or branched alkyl groups optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms
  • a straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent
  • R 14 and R 15 may be the same or different from each other.
  • a substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 4) represented by the following general formula (1a-1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond
  • B represents a substituted group
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups
  • R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon.
  • 1 to 1 atom 6 linear or branched alkyl groups optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms
  • a straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent
  • R 14 and R 15 may be the same or different from each other.
  • a substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 4) represented by the following general formula (1b-1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond
  • B represents a substituted group
  • Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups
  • R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon.
  • 1 to 1 atom 6 linear or branched alkyl groups optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms
  • a straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent
  • R 14 and R 15 may be the same or different from each other.
  • a substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 1) represented by the following general formula (1-2).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond.
  • Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
  • Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other.
  • a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group,
  • the present invention also relates to a compound having a phenanthroacridan ring structure described in 7) above, represented by the following general formula (1a-2).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond.
  • Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
  • Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other.
  • a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group,
  • the present invention is also a compound having a phenanthroacridan ring structure described in 7) above, represented by the following general formula (1b-2).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond.
  • Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
  • Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other.
  • a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group,
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 1) represented by the following general formula (1-3).
  • Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group.
  • R 1 ⁇ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group
  • An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 10) represented by the following general formula (1a-3).
  • Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group.
  • R 1 ⁇ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group
  • An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the present invention is a compound having a phenanthroacridan ring structure described in the above 10) represented by the following general formula (1b-3).
  • Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group.
  • R 1 ⁇ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group
  • An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the compound having a phenanthroacridan ring structure described in 1) above is at least one organic layer. It is an organic electroluminescent element characterized by being used as a constituent material of a layer.
  • this invention is an organic electroluminescent element of the said 13) description whose said organic layer is a positive hole transport layer.
  • this invention is an organic electroluminescent element of the said 13) description whose said organic layer is an electron blocking layer.
  • this invention is an organic electroluminescent element of the said 13) description whose said organic layer is a positive hole injection layer.
  • this invention is an organic electroluminescent element of the said 13) description whose said organic layer is a light emitting layer.
  • a divalent group of a substituted or unsubstituted aromatic hydrocarbon “a divalent group of a substituted or unsubstituted aromatic heterocycle” represented by A in the general formula (1), or “substituted or unsubstituted "Substituted fused polycyclic aromatic divalent group” represents a divalent group formed by removing two hydrogen atoms from the above “aromatic hydrocarbon", “aromatic heterocycle” or “fused polycyclic aromatic”.
  • aromatic heterocycle in the “divalent group of a substituted or unsubstituted aromatic heterocycle” is a sulfur-containing aromatic heterocycle such as thiophene, benzothiophene, benzothiazole, dibenzothiophene, furan, Oxygen-containing aromatic heterocycles such as benzofuran, benzoxazole and dibenzofuran are preferred.
  • a in the general formula (1) is “a divalent group of a substituted or unsubstituted aromatic hydrocarbon”, “a divalent group of a substituted or unsubstituted condensed polycyclic aromatic”, or a single bond.
  • a divalent group derived from benzene or a single bond is preferred.
  • substituted or unsubstituted aromatic hydrocarbon substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group
  • substituted or unsubstituted aromatic hydrocarbon substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group
  • substituted or unsubstituted aromatic hydrocarbon substituted or unsubstituted aromatic heterocycle” or substituted condensed polycyclic aromatic
  • substituted or unsubstituted aromatic hydrocarbon substituted or unsubstituted aromatic heterocycle
  • substituted condensed polycyclic aromatic include deuterium atom, cyano group, nitro group; fluorine atom, chlorine atom Halogen atoms such as bromine atom and iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl
  • substituents may be substituted. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • aromatic hydrocarbon group specifically, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthryl group, phenanthryl group , Fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyridyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzo Oxazolyl group, benzothiazolyl group, quinoxalyl group,
  • aromatic heterocyclic group in the “substituted or unsubstituted aromatic heterocyclic group”, a sulfur-containing aromatic heterocyclic group such as thienyl group, benzothienyl group, benzothiazolyl group, dibenzothienyl group, or the like, Oxygen-containing aromatic heterocycles such as a furyl group, a benzofuranyl group, a benzoxazolyl group, and a dibenzofuranyl group are preferred.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by B in the general formula (1), specifically, , Deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert A linear or branched alkyl group having 1 to 6 carbon atoms such as a butyl group, an n-pentyl group, an isopentyl group, a neopentyl group or an n-hexyl group; a methyloxy group, an ethyloxy group or a propyloxy group A linear or branched alkyloxy group having 1 to
  • the same groups as those shown for the “aromatic group” can be mentioned, and “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group” Or “aromatic hydrocarbon group” or "
  • substituent that these groups may have also relates to the “substituent” of the above-mentioned “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group”.
  • lifted The same thing as what was shown can be mention
  • substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted condensed polycyclic aromatic group”, or “aromatic hydrocarbon group, aromatic heterocyclic ring” It is preferably a “disubstituted amino group substituted by a group selected from a group or a condensed polycyclic aromatic group”, “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted condensed polycyclic aromatic group”.
  • B in the general formula (1) is “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group”,
  • the groups in the “group” are bonded to form a ring, it is preferable to form a ring via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and through a substituted or unsubstituted methylene group.
  • A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group
  • the substituted or unsubstituted aromatic of B Selected from aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted condensed polycyclic aromatic groups, or “aromatic hydrocarbon groups, aromatic heterocyclic groups or condensed polycyclic aromatic groups” "Aromatic hydrocarbon group", "aromatic heterocyclic group” or “condensed polycyclic aromatic group” in "disubstituted amino group substituted by a group” and A is a single bond or substituted or unsubstituted methylene May be bonded to each other via a group, oxygen atom or sulfur atom, and in this case, it is preferable to form a ring via a substituted or unsubstituted methylene May be
  • aromatic heterocyclic group in the “substituted or unsubstituted aromatic heterocyclic group”, a sulfur-containing aromatic heterocyclic group such as thienyl group, benzothienyl group, benzothiazolyl group, dibenzothienyl group, or the like, Oxygen-containing aromatic heterocycles such as a furyl group, a benzofuranyl group, a benzoxazolyl group, and a dibenzofuranyl group are preferred.
  • “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” represented by Ar 1 , Ar 2 , Ar 3 or “ Specific examples of the “substituent” in the “substituted condensed polycyclic aromatic group” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl Straight chain having 1 to 6 carbon atoms such as a group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, etc.
  • a branched alkyl group a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, or a propyloxy group; an alkenyl group such as an allyl group; a phenyloxy group; Aryloxy groups such as ryloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl Groups, fluoranthenyl groups, triphenylenyl groups and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl groups, thienyl groups, furyl groups, pyrrolyl groups, quinolyl groups, iso
  • Ar 2 and Ar 3 in the general formulas (1-2) and (1-3) are “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted condensed polycyclic aromatic group”.
  • Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and in this case, a substituted or unsubstituted methylene group
  • the ring is preferably formed through an oxygen atom or a sulfur atom, and the ring is particularly preferably formed through a substituted or unsubstituted methylene group.
  • Ar 2 when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted condensed polycyclic aromatic divalent group , Ar 2 may be bonded to A through a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the ring is preferably formed through an atom or a sulfur atom, and the ring is particularly preferably formed through a substituted or unsubstituted methylene group.
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 1 to R 13 in the general formula (1), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “the linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”.
  • Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclyl Hexyl group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group, and the like 2-butenyl group.
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R 1 to R 13 in formula (1), “5 to 10 carbon atoms having a substituent”
  • the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms” specifically, a deuterium atom, a cyano group, a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent represented by R 1 to R 13 in the general formula (1) or “5 to 5 carbon atoms having a substituent”
  • Specific examples of the “substituent” in “10 cycloalkyloxy groups” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyloxy group, ethyloxy
  • Arylalkyloxy groups such as groups; phenyl groups, biphenylyl groups, terphenylyl groups
  • a group such as a group heterocyclic group may be further substituted by the above-exemplified substituents.
  • These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 13 in the general formula (1), or “substituted or unsubstituted condensed hydrocarbon group”
  • phenanthryl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, Carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl , It may be mentioned a dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 1 to R 13 in the general formula (1), Specifically, deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl Straight or branched alkyloxy groups having 1 to 6 carbon atoms such as oxy groups;
  • aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R 1 to R 13 in the general formula (1) include a phenyloxy group, biphenylyloxy group, terphenyl Examples thereof include a tolyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aryloxy group represented by R 1 to R 13 in the general formula (1), specifically, a deuterium atom, a cyano group, a nitro group; a fluorine atom, a chlorine atom, Halogen atoms such as bromine atom and iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n- A linear or branched alkyl group having 1 to 6 carbon atoms such as a hexyl group; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group or a propyloxy group Alkenyl group such as allyl
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 14 or R 15 in the general formula (1), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “the linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”.
  • Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, Rohekishiru group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group include a 2-butenyl group, and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R 14 or R 15 in the general formula (1), “5 to 10 carbon atoms having a substituent”
  • the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms” specifically, a deuterium atom, a cyano group, a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group; Aromatic hydrocarbon groups or condensed
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent represented by R 14 or R 15 in the general formula (1) or “C5 to C having a substituent”
  • Specific examples of the “substituent” in “10 cycloalkyloxy groups” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyloxy group, ethyloxy
  • Arylalkyloxy groups such as a group; phenyl group, biphenylyl group, terphenylyl group,
  • substituents may be further substituted by the above-exemplified substituents.
  • substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 14 or R 15 in the general formula (1), or “substituted or unsubstituted condensed polycyclic group”
  • phenanthryl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, Indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group Pyrazolyl group include dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 14 and R 15 in the general formula (1), Specifically, deuterium atom, trifluoromethyl group, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, a linear or branched alkyl group having 1 to 6 carbon atoms such as n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group A linear or branched alkyloxy group having 1 to 6 carbon atoms such as ethyloxy group
  • substituents may be further substituted by the above-exemplified substituents. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R 14 and R 15 in the general formula (1) include a phenyloxy group, a biphenylyloxy group, a terfeny group. Examples thereof include a tolyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aryloxy group represented by R 14 and R 15 in the general formula (1)
  • substituents include deuterium atom, trifluoromethyl group, cyano group, nitro group; fluorine Halogen atoms such as atoms, chlorine atoms, bromine atoms, iodine atoms; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, Linear or branched alkyl group having 1 to 6 carbon atoms such as neopentyl group and n-hexyl group; linear or branched alkyl group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group Alkyloxy groups; alkenyl groups such as allyl groups; a
  • the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention is a novel compound, and has an excellent electron blocking ability than a conventional hole transport material, and an excellent amorphous And a thin film state is stable.
  • the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention is a hole injection layer and / or a hole transport layer of an organic electroluminescence element (hereinafter abbreviated as an organic EL element). It can be used as a constituent material of the layer.
  • an organic EL element organic electroluminescence element
  • the probability of recombination of holes and electrons can be improved, high luminous efficiency can be obtained, the driving voltage is lowered, and the durability of the organic EL element is improved.
  • the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention can also be used as a constituent material of an electron blocking layer of an organic EL device.
  • the driving voltage is lowered and current resistance is maintained while having high luminous efficiency. Is improved and the maximum light emission luminance of the organic EL element is improved.
  • the compound represented by the general formula (1) of the present invention and having a phenanthroacridan ring structure can also be used as a constituent material of a light emitting layer of an organic EL element.
  • the material of the present invention which has excellent hole transportability compared to conventional materials and has a wide band gap, is used as a host material for the light-emitting layer, and supports a fluorescent or phosphorescent emitter called a dopant to emit light. By using it as a layer, it has the effect
  • the organic EL device of the present invention has higher hole mobility than conventional hole transport materials, excellent electron blocking ability, excellent amorphous property, and stable thin film state. Since a compound having a throacridan ring structure is used, high efficiency and high durability can be realized.
  • the compound having a phenanthroacridan ring structure of the present invention is useful as a constituent material of a hole injection layer, a hole transport layer, an electron blocking layer or a light emitting layer of an organic EL device, and has an excellent electron blocking ability. And has good amorphous properties, a stable thin film state, and excellent heat resistance.
  • the organic EL device of the present invention has high luminous efficiency and power efficiency, which can reduce the practical driving voltage of the device and improve the durability.
  • FIG. 1 is a 1 H-NMR chart of the compound of Example 1 of the present invention (Compound 4).
  • FIG. 2 is a 1 H-NMR chart of the compound of Example 2 of the present invention (Compound 8).
  • FIG. 6 is a diagram showing EL element configurations of Example 5, Example 6, and Comparative Example 1.
  • the compound having a phenanthroacridan ring structure of the present invention is a novel compound, and these compounds can be synthesized, for example, as follows. First, 13-bromo-10-arylphenanthroacridane was synthesized by bromination of the corresponding 10-position substituted phenanthroacridane with an aryl group with bromine or N-bromosuccinimide, A compound having a phenanthroacridan ring structure can be synthesized by performing a cross-coupling reaction such as Buchwald-Hartwig reaction between this bromo compound and various diarylamines.
  • the compound having a phenanthroacridan ring structure of the present invention can be synthesized as follows. First, the above-described 13-bromo-10-arylphenanthroacridan and various diarylamines are subjected to a cross-coupling reaction such as the Ullmann reaction (see, for example, Non-Patent Document 5) to thereby obtain a phenanthroacridan. A compound having a ring structure can be synthesized.
  • the compound having a phenanthroacridan ring structure of the present invention can be synthesized as follows.
  • Cross coupling reaction such as Suzuki coupling between the 13-bromo-10-arylphenanthroacridan and various boronic acids or boronic esters (for example, see Non-patent Document 6) (for example, Non-Patent Document 7)
  • the compound having the indenoacridan ring structure of the present invention can be synthesized.
  • Tg glass transition point
  • work function index of hole transportability
  • the glass transition point (Tg) was determined with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S) using powder.
  • the work function was measured using an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) after forming a 100 nm thin film on the ITO substrate.
  • PYS-202 manufactured by Sumitomo Heavy Industries, Ltd.
  • the structure of the organic EL device of the present invention includes an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on the substrate, and between the anode and the hole transport layer. And those having an electron injection layer between the electron transport layer and the cathode.
  • these multilayer structures several organic layers can be omitted.
  • a structure having an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on a substrate can be used. .
  • an electrode material having a large work function such as ITO or gold is used.
  • a hole injection layer of the organic EL device of the present invention in addition to a compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, a porphyrin compound represented by copper phthalocyanine, a starburst type Materials such as triphenylamine derivatives, various triphenylamine tetramers, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • N, N′-diphenyl-N, N′— Di (m-tolyl) benzidine hereinafter abbreviated as TPD
  • NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
  • NPD N, N, N ′ Benzidine derivatives such as N, -tetrabiphenylylbenzidine, 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane
  • TAPC various triphenylamine trimers and 4 A mer
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS poly (styrene sulfonate)
  • a material that is usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony or the like, or a TPD structure having a partial structure. Molecular compounds and the like can be used.
  • the electron blocking layer of the organic EL device of the present invention in addition to the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, 4,4 ′, 4 ′′ -tri (N— Carbazolyl) triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis [4- (carbazol-9-yl) phenyl] fluorene, 1,3-bis (carbazol-9-yl) benzene (hereinafter mCP) Carbazole derivatives such as 2,2-bis (4-carbazol-9-ylphenyl) adamantane (hereinafter abbreviated as Ad-Cz), 9- [4- (carbazol-9-yl) phenyl] It has an electron blocking action such as a compound having a triphenylamine group represented by -9- [4- (triphenylsilyl) phenyl] -9H-fluorene and a triarylamine structure
  • That compound can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • the light emitting layer of the organic EL device of the present invention various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, etc., in addition to metal complexes of quinolinol derivatives including Alq 3 Can be used.
  • the light emitting layer may be composed of a host material and a dopant material.
  • the host material in addition to the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, the light emitting material
  • thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, and the like can be used.
  • quinacridone coumarin, rubrene, perylene, and derivatives thereof
  • benzopyran derivatives rhodamine derivatives, aminostyryl derivatives, and the like
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • a phosphorescent material can be used as the light emitting material.
  • a phosphorescent material of a metal complex such as iridium or platinum can be used.
  • Green phosphorescent emitters such as Ir (ppy) 3
  • blue phosphorescent emitters such as FIrpic and FIr6, and red phosphorescent emitters
  • Btp 2 Ir (acac) are used as the host material.
  • carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, mCP, etc.
  • a compound having a phenanthroacridan ring structure represented can be used as a hole injection / transport host material.
  • a compound having a phenanthroacridan ring structure represented can be used.
  • an electron transporting host material p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) can be used, and a high-performance organic EL device can be produced.
  • the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
  • Non-Patent Document 3 a material that emits delayed fluorescence such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN as the light emitting material (see, for example, Non-Patent Document 3).
  • CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”).
  • BCP bathocuproine
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline, in addition to metal complexes of quinolinol derivatives including Alq 3 and BAlq.
  • Derivatives, phenanthroline derivatives, silole derivatives and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • an alkali metal salt such as lithium fluoride and cesium fluoride
  • an alkaline earth metal salt such as magnesium fluoride
  • a metal oxide such as aluminum oxide
  • an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
  • the compound of the present invention has a glass transition point of 100 ° C. or higher, which indicates that the thin film state is stable in the compound of the present invention.
  • the compound of the present invention exhibits a suitable energy level as compared with the work function of 5.5 eV which is possessed by general hole transport materials such as NPD and TPD, and has a good hole transport capability.
  • the organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2 as shown in FIG. 6, an electron injection layer 7 and a cathode (aluminum electrode) 8 were deposited in this order.
  • the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, a compound 59 having the following structural formula was formed to a thickness of 20 nm as the hole injection layer 3 so as to cover the transparent anode 2. On this hole injection layer 3, the compound (compound 4) of Example 1 of the present invention was formed as a hole transport layer 4 so as to have a film thickness of 40 nm.
  • a film thickness of 30 nm On this emitting layer 5 was formed to have the Alq 3 film thickness 30nm as an electron transport layer 6.
  • lithium fluoride was formed as the electron injection layer 7 so as to have a film thickness of 0.5 nm.
  • aluminum was deposited to a thickness of 150 nm to form the cathode 8.
  • the characteristic measurement was performed at normal temperature in air
  • Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the organic EL device produced using the compound of Example 1 (Compound 4) of the present invention.
  • Example 5 the compound (Compound 8) of Example 2 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 4) of Example 1 of the present invention as a material for the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 1 For comparison, in Example 5, except that the compound of the following structural formula was formed to a film thickness of 40 nm instead of the compound of Example 1 of the present invention (Compound 4) as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • the driving voltage when a current density of 10 mA / cm 2 was passed was 5.17 V of the device of Comparative Example 1 using Compound 62, and the compound 4 or 8 of the present invention was used.
  • the voltage was lowered to 4.78 to 4.98 V in all cases.
  • the device of Examples 5 to 6 using the compound 4 or 8 of the present invention is 6.15 to 5.49 lm / W of the device of Comparative Example 1 using the compound 62. Both were greatly improved to 6.48 lm / W.
  • the compound of the present invention was improved with respect to the compound 62 in both luminance and luminous efficiency.
  • the organic EL device using the compound having a phenanthroacridan ring structure of the present invention has brightness, luminous efficiency, and the like even when compared with the organic EL device using the compound 62. It was found that an improvement in power efficiency and a decrease in practical driving voltage can be achieved.
  • the compound having a phenanthroacridan ring structure of the present invention is excellent as a compound for an organic EL device because of its high hole transport ability, excellent amorphousness, and stable thin film state.
  • an organic EL element By producing an organic EL element using the compound, high luminance, light emission efficiency, and power efficiency can be obtained, practical driving voltage can be lowered, and durability can be improved. For example, it has become possible to develop home appliances and lighting.

Abstract

[Problem] To provide an organic compound having excellent hole injection and transport capability, electron blocking capability, high stability in a thin-film state, and excellent heat resistance, as a material for a high-efficiency, durable organic electroluminescence element; and to provide a high luminous-efficiency, durable organic electroluminescence element using this compound. [Solution] A compound having a phenanthroacridan ring structure represented by general formula (1). An organic electroluminescence element having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein said compound is used as a constituent material of at least one organic layer.

Description

フェナンスロアクリダン環構造を有する化合物および有機エレクトロルミネッセンス素子Compounds having a phenanthracridan ring structure and organic electroluminescence devices
　本発明は、各種の表示装置に好適な自発光素子である有機エレクトロルミネッセンス素子に適した化合物と該素子に関するものであリ、詳しくはフェナンスロアクリダン環構造を有する化合物と、該化合物を用いた有機エレクトロルミネッセンス素子に関するものである。 The present invention relates to a compound suitable for an organic electroluminescence element which is a self-luminous element suitable for various display devices, and to the element, and more specifically, a compound having a phenanthracridan ring structure, and the compound. The present invention relates to an organic electroluminescence element used.
　有機エレクトロルミネッセンス素子は自己発光性素子であるため、液晶素子にくらべて明るく視認性に優れ、鮮明な表示が可能であるため、活発な研究がなされてきた。 Since organic electroluminescence elements are self-luminous elements, they have been actively researched because they are brighter and more visible than liquid crystal elements, and can display clearly.
　１９８７年にイーストマン・コダック社のＣ．Ｗ．Ｔａｎｇらは各種の役割を各材料に分担した積層構造素子を開発することにより有機材料を用いた有機エレクトロルミネッセンス素子を実用的なものにした。彼らは電子を輸送することのできる蛍光体、トリス（８－ヒドロキシキノリン）アルミニウム（以後、Ａｌｑ３と略称する）と正孔を輸送することのできる芳香族アミン化合物とを積層し、両方の電荷を蛍光体の層の中に注入して発光させることにより、１０Ｖ以下の電圧で１０００ｃｄ／ｍ２以上の高輝度を得た（例えば、特許文献１および特許文献２参照）。 In 1987, Eastman Kodak's C.I. W. Tang et al. Have made organic electroluminescence elements using organic materials practical by developing a laminated structure element that shares various roles with each material. They are composed of a phosphor capable of transporting electrons, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ) and an aromatic amine compound capable of transporting holes, Was injected into the phosphor layer to emit light, whereby high luminance of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
　現在まで、有機エレクトロルミネッセンス素子の実用化のために多くの改良がなされ、各種の役割をさらに細分化して、基板上に順次に、陽極、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層、陰極を設けた電界発光素子によって高効率と耐久性が達成されている（例えば、非特許文献1参照）。 To date, many improvements have been made for the practical application of organic electroluminescence devices, and various roles have been further subdivided, and sequentially on the substrate, anode, hole injection layer, hole transport layer, light emitting layer, electron High efficiency and durability are achieved by an electroluminescent device provided with a transport layer, an electron injection layer, and a cathode (see, for example, Non-Patent Document 1).
　また、発光効率のさらなる向上を目的として三重項励起子の利用が試みられ、燐光発光性化合物の利用が検討されている（例えば、非特許文献２参照）。
　そして、熱活性化遅延蛍光（ＴＡＤＦ）による発光を利用する素子も開発されている。２０１１年に九州大学の安達らは、熱活性化遅延蛍光材料を用いた素子によって５．３％の外部量子効率を実現させた（例えば、非特許文献３参照）。 Further, the use of triplet excitons has been attempted for the purpose of further improving the light emission efficiency, and the use of phosphorescent compounds has been studied (see, for example, Non-Patent Document 2).
An element utilizing light emission by thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Adachi et al. Of Kyushu University realized an external quantum efficiency of 5.3% using a device using a thermally activated delayed fluorescent material (see, for example, Non-Patent Document 3).
　発光層は、一般的にホスト材料と称される電荷輸送性の化合物に、蛍光性化合物や燐光発光性化合物または遅延蛍光を放射する材料をドープして作製することもできる。上記の講習会予稿集に記載されているように、有機エレクトロルミネッセンス素子における有機材料の選択は、その素子の効率や耐久性など諸特性に大きな影響を与える。 The light emitting layer can be prepared by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound or a material emitting delayed fluorescence. As described in the above seminar proceedings collection, the selection of an organic material in an organic electroluminescence element greatly affects various characteristics such as efficiency and durability of the element.
　有機エレクトロルミネッセンス素子においては、両電極から注入された電荷が発光層で再結合して発光が得られるが、正孔、電子の両電荷を如何に効率よく発光層に受け渡すかが重要であり、正孔注入性を高め、陰極から注入された電子をブロックする電子阻止性を高めることによって、正孔と電子が再結合する確率を向上させ、さらには発光層内で生成した励起子を閉じ込めることによって、高発光効率を得ることができる。そのため、正孔輸送材料の果たす役割は重要であり、正孔注入性が高く、正孔の移動度が大きく、電子阻止性が高く、さらには電子に対する耐久性が高い正孔輸送材料が求められている。 In an organic electroluminescence device, the light injected from both electrodes recombines in the light emitting layer to obtain light emission. However, it is important how efficiently both holes and electrons are transferred to the light emitting layer. Improve the probability of recombination of holes and electrons by increasing the hole injection property and blocking the electron injected from the cathode, and further confine excitons generated in the light emitting layer Thus, high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.
　また、素子の寿命に関しては材料の耐熱性やアモルファス性も重要である。耐熱性が低い材料では、素子駆動時に生じる熱により、低い温度でも熱分解が起こり、材料が劣化する。アモルファス性が低い材料では、短い時間でも薄膜の結晶化が起こり、素子が劣化してしまう。そのため使用する材料には耐熱性が高く、アモルファス性が良好な性質が求められる。 Also, the heat resistance and amorphous nature of the material are important for the lifetime of the element. In a material having low heat resistance, thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated. In the case of a material having low amorphous property, the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.
　これまで有機エレクトロルミネッセンス素子に用いられてきた正孔輸送材料としては、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（α－ナフチル）ベンジジン（以後、ＮＰＤと略称する）や種々の芳香族アミン誘導体が知られていた（例えば、特許文献１および特許文献２参照）。ＮＰＤは良好な正孔輸送能力を持っているが、耐熱性の指標となるガラス転移点（Ｔｇ）が９６℃と低く、高温条件下では結晶化による素子特性の低下が起こってしまう（例えば、非特許文献４参照）。また、前記特許文献１や特許文献２に記載の芳香族アミン誘導体の中には、正孔の移動度が１０－３ｃｍ２／Ｖｓ以上と優れた移動度を有する化合物が知られているが、電子阻止性が不十分であるため、電子の一部が発光層を通り抜けてしまい、発光効率の向上が期待できないなど、さらなる高効率化のため、より電子阻止性が高く、薄膜がより安定で耐熱性の高い材料が求められていた。 Examples of hole transport materials that have been used in organic electroluminescence devices so far include N, N′-diphenyl-N, N′-di (α-naphthyl) benzidine (hereinafter abbreviated as NPD) and various aromatics. Amine derivatives have been known (see, for example, Patent Document 1 and Patent Document 2). NPD has a good hole transport capability, but its glass transition point (Tg), which is an index of heat resistance, is as low as 96 ° C., and device characteristics are degraded due to crystallization under high temperature conditions (for example, Non-patent document 4). Further, among the aromatic amine derivatives described in Patent Document 1 and Patent Document 2, compounds having an excellent mobility of hole mobility of 10 −3 cm 2 / Vs or more are known. Because of insufficient electron blocking properties, some of the electrons pass through the light emitting layer and cannot be expected to improve luminous efficiency. For higher efficiency, the electron blocking properties are higher and the thin film is more stable. Therefore, a material having high heat resistance has been demanded.
　耐熱性や正孔注入性、電子阻止性などの特性を改良した化合物として、下記の式で表される置換アクリダン構造を有するアリールアミン化合物（例えば、化合物Ａ、Ｂ）が提案されている。（例えば、特許文献３～４参照）。 As compounds having improved properties such as heat resistance, hole injection properties, and electron blocking properties, arylamine compounds having a substituted acridan structure represented by the following formula (for example, compounds A and B) have been proposed. (For example, see Patent Documents 3 to 4).
Figure JPOXMLDOC01-appb-C000001
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物Ａ）
Figure JPOXMLDOC01-appb-C000001
 (Compound A)
Figure JPOXMLDOC01-appb-C000002
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物Ｂ）
Figure JPOXMLDOC01-appb-C000002
 (Compound B)
　しかしながら、これらの化合物を正孔注入層または正孔輸送層に用いた素子では、耐熱性や発光効率などの改良はされているものの、未だ十分とはいえず、また、低駆動電圧化や電流効率も十分とはいえず、アモルファス性にも問題があった。そのため、アモルファス性を高めつつ、さらなる低駆動電圧化や、さらなる高発光効率化が求められていた。 However, devices using these compounds in the hole injection layer or hole transport layer have been improved in heat resistance and light emission efficiency, but are still not sufficient. The efficiency was not sufficient, and there was a problem with amorphousness. For this reason, there has been a demand for further lower drive voltage and higher light emission efficiency while enhancing amorphousness.
　また、発光層のホスト化合物として、下記の式で表されるようなフェナンスロアクリダン誘導体（例えば、化合物Ｃ）は知られているが、正孔輸送性を有するフェナンスロアクリダン環構造を有する化合物は知られていなかった（例えば、特許文献５参照）。
Figure JPOXMLDOC01-appb-C000003
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物Ｃ） Further, as a host compound of the light emitting layer, a phenanthroacridan derivative represented by the following formula (for example, Compound C) is known, but a phenanthroacridan ring structure having a hole transporting property is known. The compound which has was not known (for example, refer patent document 5).
Figure JPOXMLDOC01-appb-C000003
 (Compound C)
特開平８－４８６５６号公報JP-A-8-48656 特許第３１９４６５７号公報Japanese Patent No. 3194657 ＷＯ２００６／０３３５６３号公報WO2006 / 033563 publication ＷＯ２００７／１１０２２８号公報WO2007 / 110228 publication ＷＯ２０１２／０９３８６１号公報WO2012 / 093861
　本発明の目的は、高効率、高耐久性の有機エレクトロルミネッセンス素子用の材料として、正孔の注入・輸送性能に優れ、電子阻止能力を有し、薄膜状態での安定性が高く、耐熱性に優れた特性を有する有機化合物を提供し、さらにこの化合物を用いて、高発光効率、高耐久性の有機エレクトロルミネッセンス素子を提供することにある。 The object of the present invention is as a highly efficient and durable organic electroluminescent device material, excellent in hole injection / transport performance, electron blocking ability, high stability in a thin film state, and heat resistance It is another object of the present invention to provide an organic compound having excellent characteristics and to provide an organic electroluminescence device having high luminous efficiency and durability using this compound.
　本発明が提供しようとする有機化合物が具備すべき物理的な特性としては、（１）正孔の注入特性がよいこと、（２）正孔の移動度が大きいこと、（３）電子阻止能力に優れること、（４）薄膜状態が安定であること、（５）耐熱性に優れていること、をあげることができる。また、本発明が提供しようとする有機エレクトロルミネッセンス素子が具備すべき物理的な特性としては、（１）発光効率および電力効率が高いこと、（２）発光開始電圧が低いこと、（３）実用駆動電圧が低いこと、をあげることができる。 The physical characteristics that the organic compound to be provided by the present invention should have include (1) good hole injection characteristics, (2) high hole mobility, and (3) electron blocking ability. (4) The thin film state is stable, and (5) The heat resistance is excellent. The physical characteristics of the organic electroluminescent device to be provided by the present invention include (1) high luminous efficiency and power efficiency, (2) low emission start voltage, and (3) practical use. The drive voltage is low.
　そこで本発明者らは上記の目的を達成するために、フェナンスロアクリダン環構造が平面性を有することによって高い正孔移動度が期待できること、また、優れた電子阻止性を有することが期待できること、さらにはこの部分構造が有する耐熱性と薄膜安定性への効果に期待して、フェナンスロアクリダン環構造を有する化合物を設計して化学合成し、該化合物を用いて種々の有機エレクトロルミネッセンス素子を試作し、素子の特性評価を鋭意行った結果、本発明を完成するに至った。 Therefore, in order to achieve the above object, the present inventors are expected to have high hole mobility due to the planarity of the phenanthroacridan ring structure and to have excellent electron blocking properties. In anticipation of the effects on the heat resistance and thin film stability of this partial structure, a compound having a phenanthroacridan ring structure is designed and chemically synthesized. As a result of prototyping a luminescence element and intensively evaluating the characteristics of the element, the present invention has been completed.
１）すなわち本発明は、下記一般式（１）で表される、フェナンスロアクリダン環構造を有する化合物である。 1) That is, the present invention is a compound having a phenanthroacridan ring structure represented by the following general formula (1).
Figure JPOXMLDOC01-appb-C000004
 　　　　　　　　　　　　　　　　　　　　　　　　　（１）
Figure JPOXMLDOC01-appb-C000004
 (1)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
２）また本発明は、下記一般式（１ａ）で表される、上記１）記載のフェナンスロアクリダン環構造を有する化合物である。 2) Moreover, this invention is a compound which has the phenanthroacridan ring structure of said 1) description represented by the following general formula (1a).
Figure JPOXMLDOC01-appb-C000005
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ）
Figure JPOXMLDOC01-appb-C000005
 (1a)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
３）また本発明は、下記一般式（１ｂ）で表される、上記１）記載のフェナンスロアクリダン環構造を有する化合物である。 3) Moreover, this invention is a compound which has the phenanthroacridan ring structure of said 1) represented by the following general formula (1b).
Figure JPOXMLDOC01-appb-C000006
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ）
Figure JPOXMLDOC01-appb-C000006
 (1b)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
４）また本発明は、下記一般式（１－１）で表される、上記１）記載のフェナンスロアクリダン環構造を有する化合物である。 4) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 1) represented by the following general formula (1-1).
Figure JPOXMLDOC01-appb-C000007
 　　　　　　　　　　　　　　　　　　　　　　　　　（１－１）
Figure JPOXMLDOC01-appb-C000007
 (1-1)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
５）また本発明は、下記一般式（１ａ－１）で表される、上記４）記載のフェナンスロアクリダン環構造を有する化合物である。 5) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 4) represented by the following general formula (1a-1).
Figure JPOXMLDOC01-appb-C000008
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ－１）
Figure JPOXMLDOC01-appb-C000008
 (1a-1)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
６）また本発明は、下記一般式（１ｂ－１）で表される、上記４）記載のフェナンスロアクリダン環構造を有する化合物である。 6) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 4) represented by the following general formula (1b-1).
Figure JPOXMLDOC01-appb-C000009
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ－１）
Figure JPOXMLDOC01-appb-C000009
 (1b-1)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
７）また本発明は、下記一般式（１－２）で表される、上記１）記載のフェナンスロアクリダン環構造を有する化合物である。 7) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 1) represented by the following general formula (1-2).
Figure JPOXMLDOC01-appb-C000010
 　　　　　　　　　　　　　　　　　　　　　　　　　（１－２）
Figure JPOXMLDOC01-appb-C000010
 (1-2)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表す。Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＡｒ２は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond. Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other. A hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom R 14 and R 15 may be the same as or different from each other, and may be a straight chain having 1 to 6 carbon atoms which may have a substituent or Min Alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain or branched alkenyl groups having 2 to 6 carbon atoms A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 14 and R 15 May be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, wherein A is a substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted In the case of an unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and Ar 2 are bonded via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be combined with each other to form a ring. )
８）また本発明は、下記一般式（１ａ－２）で表される、上記７）記載のフェナンスロアクリダン環構造を有する化合物である。 8) The present invention also relates to a compound having a phenanthroacridan ring structure described in 7) above, represented by the following general formula (1a-2).
Figure JPOXMLDOC01-appb-C000011
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ－２）
Figure JPOXMLDOC01-appb-C000011
 (1a-2)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表す。Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＡｒ２は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond. Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other. A hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom R 14 and R 15 may be the same as or different from each other, and may be a straight chain having 1 to 6 carbon atoms which may have a substituent or Min Alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain or branched alkenyl groups having 2 to 6 carbon atoms A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 14 and R 15 May be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, wherein A is a substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted In the case of an unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and Ar 2 are bonded via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be combined with each other to form a ring. )
９）また本発明は、下記一般式（１ｂ－２）で表される、上記７）記載のフェナンスロアクリダン環構造を有する化合物である。 9) The present invention is also a compound having a phenanthroacridan ring structure described in 7) above, represented by the following general formula (1b-2).
Figure JPOXMLDOC01-appb-C000012
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ－２）
Figure JPOXMLDOC01-appb-C000012
 (1b-2)
（式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表す。Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＡｒ２は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond. Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other. A hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom R 14 and R 15 may be the same as or different from each other, and may be a straight chain having 1 to 6 carbon atoms which may have a substituent or Min Alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain or branched alkenyl groups having 2 to 6 carbon atoms A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 14 and R 15 May be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, wherein A is a substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted In the case of an unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and Ar 2 are bonded via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be combined with each other to form a ring. )
１０）また本発明は、下記一般式（１－３）で表される、上記１）記載のフェナンスロアクリダン環構造を有する化合物である。 10) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 1) represented by the following general formula (1-3).
Figure JPOXMLDOC01-appb-C000013
 　　　　　　　　　　　　　　　　　　　　　　　　　（１－３）
Figure JPOXMLDOC01-appb-C000013
 (1-3)
（式中、Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group. represents polycyclic aromatic group, Ar 2 and Ar 3 represents a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom bonded to each other via a to good .R 1 ~ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, a single bond, a substituted or unsubstituted methylene group, R 14 and R 15 may be the same or different from each other and may have a substituent, and may have a substituent, from 1 to 6 carbon atoms. A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or A branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cyclocarbon having 5 to 10 carbon atoms which may have a substituent; An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
１１）また本発明は、下記一般式（１ａ－３）で表される、上記１０）記載のフェナンスロアクリダン環構造を有する化合物である。 11) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 10) represented by the following general formula (1a-3).
Figure JPOXMLDOC01-appb-C000014
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ－３）
Figure JPOXMLDOC01-appb-C000014
 (1a-3)
（式中、Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group. represents polycyclic aromatic group, Ar 2 and Ar 3 represents a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom bonded to each other via a to good .R 1 ~ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, a single bond, a substituted or unsubstituted methylene group, R 14 and R 15 may be the same or different from each other and may have a substituent, and may have a substituent, from 1 to 6 carbon atoms. A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or A branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cyclocarbon having 5 to 10 carbon atoms which may have a substituent; An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
１２）また本発明は、下記一般式（１ｂ－３）で表される、上記１０）記載のフェナンスロアクリダン環構造を有する化合物である。 12) Further, the present invention is a compound having a phenanthroacridan ring structure described in the above 10) represented by the following general formula (1b-3).
Figure JPOXMLDOC01-appb-C000015
 　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ－３）
Figure JPOXMLDOC01-appb-C000015
 (1b-3)
（式中、Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。） (In the formula, Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group. represents polycyclic aromatic group, Ar 2 and Ar 3 represents a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom bonded to each other via a to good .R 1 ~ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, a single bond, a substituted or unsubstituted methylene group, R 14 and R 15 may be the same or different from each other and may have a substituent, and may have a substituent, from 1 to 6 carbon atoms. A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or A branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cyclocarbon having 5 to 10 carbon atoms which may have a substituent; An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
１３）また本発明は、一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機エレクトロルミネッセンス素子において、上記１）記載のフェナンスロアクリダン環構造を有する化合物が、少なくとも１つの有機層の構成材料として用いられていることを特徴とする有機エレクトロルミネッセンス素子である。 13) In the organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched between the electrodes, the compound having a phenanthroacridan ring structure described in 1) above is at least one organic layer. It is an organic electroluminescent element characterized by being used as a constituent material of a layer.
１４）また、本発明は、前記有機層が正孔輸送層である、上記１３）記載の有機エレクトロルミネッセンス素子である。 14) Moreover, this invention is an organic electroluminescent element of the said 13) description whose said organic layer is a positive hole transport layer.
１５）また、本発明は、前記有機層が電子阻止層である、上記１３）記載の有機エレクトロルミネッセンス素子である。 15) Moreover, this invention is an organic electroluminescent element of the said 13) description whose said organic layer is an electron blocking layer.
１６）また、本発明は、前記有機層が正孔注入層である、上記１３）記載の有機エレクトロルミネッセンス素子である。 16) Moreover, this invention is an organic electroluminescent element of the said 13) description whose said organic layer is a positive hole injection layer.
１７）また、本発明は、前記有機層が発光層である、上記１３）記載の有機エレクトロルミネッセンス素子である。 17) Moreover, this invention is an organic electroluminescent element of the said 13) description whose said organic layer is a light emitting layer.
　一般式（１）中のＡで表される「置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基」における「置換もしくは無置換の芳香族炭化水素」、「置換もしくは無置換の芳香族複素環」または「置換もしくは無置換の縮合多環芳香族」の「芳香族炭化水素」、「芳香族複素環」または「縮合多環芳香族」としては、具体的に、ベンゼン、ビフェニル、ターフェニル、テトラキスフェニル、スチレン、ナフタレン、アントラセン、アセナフチレン、フルオレン、フェナントレン、インダン、ピレン、ピリジン、ピリミジン、トリアジン、フラン、ピロール、チオフェン、キノリン、イソキノリン、ベンゾフラン、ベンゾチオフェン、インドリン、カルバゾール、カルボリン、ベンゾオキサゾール、ベンゾチアゾール、キノキサリン、ベンゾイミダゾール、ピラゾール、ジベンゾフラン、ジベンゾチオフェン、ナフチリジン、フェナントロリン、アクリジンなどをあげることができる。
　そして、一般式（１）中のＡで表される「置換もしくは無置換の芳香族炭化水素の２価基」、「置換もしくは無置換の芳香族複素環の２価基」または「置換もしくは無置換の縮合多環芳香族の２価基」は、上記「芳香族炭化水素」、「芳香族複素環」または「縮合多環芳香族」から水素原子を２個取り除いてできる２価基を表す。
　ここで、「置換もしくは無置換の芳香族複素環の２価基」における「芳香族複素環」としては、チオフェン、ベンゾチオフェン、ベンゾチアゾール、ジベンゾチオフェンなどの含硫黄芳香族複素環または、フラン、ベンゾフラン、ベンゾオキサゾール、ジベンゾフランなどの含酸素芳香族複素環が好ましい。 “In the substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group” represented by A in the general formula (1) "Aromatic hydrocarbon", "Aromatic heterocycle" or "Substituted or unsubstituted aromatic hydrocarbon", "Substituted or unsubstituted aromatic heterocycle" or "Substituted or unsubstituted condensed polycyclic aromatic" or Specific examples of the “fused polycyclic aromatic” include benzene, biphenyl, terphenyl, tetrakisphenyl, styrene, naphthalene, anthracene, acenaphthylene, fluorene, phenanthrene, indane, pyrene, pyridine, pyrimidine, triazine, furan, pyrrole, Thiophene, quinoline, isoquinoline, benzofuran, benzothiophene, indoline, carbazole, carboli , Can be exemplified benzoxazole, benzothiazole, quinoxaline, benzimidazole, pyrazole, dibenzofuran, dibenzothiophene, naphthyridine, phenanthroline, acridine, and the like.
In addition, “a divalent group of a substituted or unsubstituted aromatic hydrocarbon”, “a divalent group of a substituted or unsubstituted aromatic heterocycle” represented by A in the general formula (1), or “substituted or unsubstituted "Substituted fused polycyclic aromatic divalent group" represents a divalent group formed by removing two hydrogen atoms from the above "aromatic hydrocarbon", "aromatic heterocycle" or "fused polycyclic aromatic". .
Here, the “aromatic heterocycle” in the “divalent group of a substituted or unsubstituted aromatic heterocycle” is a sulfur-containing aromatic heterocycle such as thiophene, benzothiophene, benzothiazole, dibenzothiophene, furan, Oxygen-containing aromatic heterocycles such as benzofuran, benzoxazole and dibenzofuran are preferred.
　一般式（１）中のＡとしては、「置換もしくは無置換の芳香族炭化水素の２価基」、「置換もしくは無置換の縮合多環芳香族の２価基」、または単結合であることが好ましく、特にベンゼンから誘導される２価基、または単結合であることが好ましい。 A in the general formula (1) is “a divalent group of a substituted or unsubstituted aromatic hydrocarbon”, “a divalent group of a substituted or unsubstituted condensed polycyclic aromatic”, or a single bond. In particular, a divalent group derived from benzene or a single bond is preferred.
　一般式（１）中のＡで表される「置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基」における「置換芳香族炭化水素」、「置換芳香族複素環」または「置換縮合多環芳香族」の「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “In the substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group” represented by A in the general formula (1) Specific examples of the “substituent” of “substituted aromatic hydrocarbon”, “substituted aromatic heterocycle” or “substituted condensed polycyclic aromatic” include deuterium atom, cyano group, nitro group; fluorine atom, chlorine atom Halogen atoms such as bromine atom and iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n A linear or branched alkyl group having 1 to 6 carbon atoms such as a hexyl group; a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group or a propyloxy group; Branched alkyloxy groups; alkenyl groups such as allyl groups; aryloxy groups such as phenyloxy groups and tolyloxy groups; arylalkyloxy groups such as benzyloxy groups and phenethyloxy groups; phenyl groups, biphenylyl groups, terphenylyl groups, and naphthyl groups Group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl group, thienyl group, furyl group , Pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl And aromatic heterocyclic groups such as dibenzothienyl group and carbolinyl group; aryl vinyl groups such as styryl group and naphthyl vinyl group; and groups such as acyl groups such as acetyl group and benzoyl group. Further, the above-exemplified substituents may be substituted.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＢで表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、およびカルボリニル基などをあげることができる。
　ここで、「置換もしくは無置換の芳香族複素環基」における「芳香族複素環基」としては、チエニル基、ベンゾチエニル基、ベンゾチアゾリル基、ジベンゾチエニル基などの含硫黄芳香族複素環基または、フリル基、ベンゾフラニル基、ベンゾオキサゾリル基、ジベンゾフラニル基などの含酸素芳香族複素環が好ましい。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by B in formula (1) As the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group", specifically, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthryl group, phenanthryl group , Fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyridyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzo Oxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzo Ranil group, dibenzothienyl group, and the like carbolinyl group may be mentioned.
Here, as the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group”, a sulfur-containing aromatic heterocyclic group such as thienyl group, benzothienyl group, benzothiazolyl group, dibenzothienyl group, or the like, Oxygen-containing aromatic heterocycles such as a furyl group, a benzofuranyl group, a benzoxazolyl group, and a dibenzofuranyl group are preferred.
　一般式（１）中のＢで表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 As the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by B in the general formula (1), specifically, , Deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert A linear or branched alkyl group having 1 to 6 carbon atoms such as a butyl group, an n-pentyl group, an isopentyl group, a neopentyl group or an n-hexyl group; a methyloxy group, an ethyloxy group or a propyloxy group A linear or branched alkyloxy group having 1 to 6 carbon atoms; an alkenyl group such as an allyl group; an aryloxy group such as a phenyloxy group or a tolyloxy group; Arylalkyloxy groups such as ruoxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as: pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl Group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group and other aromatic heterocyclic groups; styryl group, naphthylvinyl group and other aryl vinyl groups; Group, can be mentioned groups such as acyl groups such as benzoyl group, these substituents may further the exemplified substituents may be substituted.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＢで表される「芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、上記の一般式（１）中のＢで表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」に関して示したものと同様の基をあげることができ、「芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」は、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。
　また、これらの基が有していてよい置換基も、上記の「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」の「置換基」に関して示したものと同様のものをあげることができ、好ましい態様も、同様のものをあげることができる。 “Aromatic hydrocarbon” in “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group” represented by B in the general formula (1) As the “group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group”, specifically, “substituted or unsubstituted aromatic hydrocarbons” represented by B in the above general formula (1) "Aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycycle" in "group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" The same groups as those shown for the “aromatic group” can be mentioned, and “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group” Or "aromatic hydrocarbon group" or "aromatic heterocyclic group" in The "condensed polycyclic aromatic group", those groups to each other is a single bond, a substituted or unsubstituted methylene group, via an oxygen atom or a sulfur atom may bond to each other to form a ring.
Further, the substituent that these groups may have also relates to the “substituent” of the above-mentioned “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group”. The same thing as what was shown can be mention | raise | lifted and a preferable aspect can also mention the same thing.
　一般式（１）中のＢとしては、「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の縮合多環芳香族基」、または「芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」であることが好ましく、「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の縮合多環芳香族基」、または「芳香族炭化水素基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」であることがより好ましく、「芳香族炭化水素基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」であることが特に好ましい。
　一般式（１）中のＢが「芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」であって、「芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」の基同士が結合して環を形成している場合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して環を形成するのが好ましく、置換もしくは無置換のメチレン基を介して環を形成するのが特に好ましい。
　また、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、Ｂの置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または「芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」とＡは、単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよく、この場合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して環を形成するのが好ましく、置換もしくは無置換のメチレン基を介して環を形成するのが特に好ましい。 As B in the general formula (1), “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted condensed polycyclic aromatic group”, or “aromatic hydrocarbon group, aromatic heterocyclic ring” It is preferably a “disubstituted amino group substituted by a group selected from a group or a condensed polycyclic aromatic group”, “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted condensed polycyclic aromatic group”. It is more preferably an “aromatic group” or “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group or a condensed polycyclic aromatic group”, and an “aromatic hydrocarbon group or a condensed polycyclic aromatic group”. Particularly preferred is a “disubstituted amino group substituted by a group selected from the group”.
B in the general formula (1) is “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group”, An "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic" in a "disubstituted amino group substituted by a group selected from a group, an aromatic heterocyclic group or a condensed polycyclic aromatic group" When the groups in the “group” are bonded to form a ring, it is preferable to form a ring via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and through a substituted or unsubstituted methylene group. It is particularly preferable to form a ring.
Further, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, the substituted or unsubstituted aromatic of B Selected from aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted condensed polycyclic aromatic groups, or “aromatic hydrocarbon groups, aromatic heterocyclic groups or condensed polycyclic aromatic groups” "Aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in "disubstituted amino group substituted by a group" and A is a single bond or substituted or unsubstituted methylene May be bonded to each other via a group, oxygen atom or sulfur atom, and in this case, it is preferable to form a ring via a substituted or unsubstituted methylene group, oxygen atom or sulfur atom. if Is to form a ring through a non-substituted methylene group is particularly preferred.
　一般式（１）、（１－２）、（１－３）中のＡｒ１、Ａｒ２、Ａｒ３で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的にフェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、およびカルボリニル基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。
　ここで、「置換もしくは無置換の芳香族複素環基」における「芳香族複素環基」としては、チエニル基、ベンゾチエニル基、ベンゾチアゾリル基、ジベンゾチエニル基などの含硫黄芳香族複素環基または、フリル基、ベンゾフラニル基、ベンゾオキサゾリル基、ジベンゾフラニル基などの含酸素芳香族複素環が好ましい。 “Substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 , Ar 2 , Ar 3 in the general formulas (1), (1-2), and (1-3), “substituted or unsubstituted Specific examples of the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” include Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthryl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group Quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quino Salil group, benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, and the like dibenzothienyl group and carbolinyl group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
Here, as the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group”, a sulfur-containing aromatic heterocyclic group such as thienyl group, benzothienyl group, benzothiazolyl group, dibenzothienyl group, or the like, Oxygen-containing aromatic heterocycles such as a furyl group, a benzofuranyl group, a benzoxazolyl group, and a dibenzofuranyl group are preferred.
　一般式（１）、（１－２）、（１－３）中のＡｒ１、Ａｒ２、Ａｒ３で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」の「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 In the general formulas (1), (1-2), and (1-3), “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” represented by Ar 1 , Ar 2 , Ar 3 or “ Specific examples of the “substituent” in the “substituted condensed polycyclic aromatic group” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl Straight chain having 1 to 6 carbon atoms such as a group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, etc. Or a branched alkyl group; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, or a propyloxy group; an alkenyl group such as an allyl group; a phenyloxy group; Aryloxy groups such as ryloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl Groups, fluoranthenyl groups, triphenylenyl groups and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl groups, thienyl groups, furyl groups, pyrrolyl groups, quinolyl groups, isoquinolyl groups, benzofuranyl groups, benzothienyl groups, indolyl groups Group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group and the like; styryl group, naphthyl group Examples thereof include aryl vinyl groups such as tilvinyl group; groups such as acyl groups such as acetyl group and benzoyl group, and these substituents may be further substituted by the above-described substituents.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１－２）、（１－３）中のＡｒ２、Ａｒ３としては、「置換もしくは無置換の芳香族炭化水素基」または「置換もしくは無置換の縮合多環芳香族基」であることが好ましい。そして、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよく、この場合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して環を形成するのが好ましく、置換もしくは無置換のメチレン基を介して環を形成するのが特に好ましい。
　また、一般式（１－２）において、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、Ａｒ２はＡと単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよく、この場合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して環を形成するのが好ましく、置換もしくは無置換のメチレン基を介して環を形成するのが特に好ましい。 Ar 2 and Ar 3 in the general formulas (1-2) and (1-3) are “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted condensed polycyclic aromatic group”. Preferably there is. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and in this case, a substituted or unsubstituted methylene group The ring is preferably formed through an oxygen atom or a sulfur atom, and the ring is particularly preferably formed through a substituted or unsubstituted methylene group.
In the general formula (1-2), when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted condensed polycyclic aromatic divalent group , Ar 2 may be bonded to A through a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. In this case, a substituted or unsubstituted methylene group, oxygen The ring is preferably formed through an atom or a sulfur atom, and the ring is particularly preferably formed through a substituted or unsubstituted methylene group.
　一般式（１）中のＲ１～Ｒ１３で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、２－ブテニル基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 “A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R 1 to R 13 in the general formula (1), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “the linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”. Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclyl Hexyl group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group, and the like 2-butenyl group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent” represented by R 1 to R 13 in formula (1), “5 to 10 carbon atoms having a substituent” As the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms”, specifically, a deuterium atom, a cyano group, a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as enylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl Group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuran Examples thereof include an aromatic heterocyclic group such as a nyl group, a dibenzothienyl group, and a carbolinyl group, and these substituents may be further substituted by the above-exemplified substituents.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、ｎ－プロピルオキシ基、イソプロピルオキシ基、ｎ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、１－アダマンチルオキシ基、２－アダマンチルオキシ基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent” represented by R 1 to R 13 in the general formula (1) or “having a substituent. Or a “C1-C6 linear or branched alkyloxy group” or “C5-C10 cycloalkyloxy group”. Specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy And the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent” represented by R 1 to R 13 in the general formula (1) or “5 to 5 carbon atoms having a substituent” Specific examples of the “substituent” in “10 cycloalkyloxy groups” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyloxy group, ethyloxy A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a propyloxy group; an alkenyl group such as an allyl group; an aryloxy group such as a phenyloxy group or a tolyloxy group; a benzyloxy group or a phenethyloxy group Arylalkyloxy groups such as groups; phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, anthracenyl groups, Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as nantril group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl Group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group, etc. A group such as a group heterocyclic group, and these substituents may be further substituted by the above-exemplified substituents.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、およびカルボリニル基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 13 in the general formula (1), or “substituted or unsubstituted condensed hydrocarbon group” Specific examples of the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthryl group. Group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, Carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl , It may be mentioned a dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 As the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 1 to R 13 in the general formula (1), Specifically, deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl Straight or branched alkyloxy groups having 1 to 6 carbon atoms such as oxy groups; alkenyl groups such as allyl groups; aryloxy groups such as phenyloxy groups and tolyloxy groups; Si group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl Group, aromatic hydrocarbon group such as triphenylenyl group or condensed polycyclic aromatic group; pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, Aromatic heterocyclic groups such as benzoxazolyl, benzothiazolyl, quinoxalyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl and carbolinyl; arylbiyl such as styryl and naphthylvinyl Le group; an acetyl group, can be mentioned groups such as acyl groups such as benzoyl group, these substituents may further the exemplified substituents may be substituted.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、具体的に、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、ナフチルオキシ基、アントリルオキシ基、フェナントリルオキシ基、フルオレニルオキシ基、インデニルオキシ基、ピレニルオキシ基、ペリレニルオキシ基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 Specific examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R 1 to R 13 in the general formula (1) include a phenyloxy group, biphenylyloxy group, terphenyl Examples thereof include a tolyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ１３で表される「置換アリールオキシ基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 As the “substituent” in the “substituted aryloxy group” represented by R 1 to R 13 in the general formula (1), specifically, a deuterium atom, a cyano group, a nitro group; a fluorine atom, a chlorine atom, Halogen atoms such as bromine atom and iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n- A linear or branched alkyl group having 1 to 6 carbon atoms such as a hexyl group; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group or a propyloxy group Alkenyl group such as allyl group; aryloxy group such as phenyloxy group and tolyloxy group; ant such as benzyloxy group and phenethyloxy group A rualkyloxy group; an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, or a triphenylenyl group; Condensed polycyclic aromatic group; pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, Aromatic heterocyclic groups such as benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group and carbolinyl group; aryl vinyl groups such as styryl group and naphthyl vinyl group; acyl groups such as acetyl group and benzoyl group It can be mentioned, these substituents Furthermore, the exemplified substituents may be substituted.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、２－ブテニル基、などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R 14 or R 15 in the general formula (1), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “the linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”. Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, Rohekishiru group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group include a 2-butenyl group, and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent” represented by R 14 or R 15 in the general formula (1), “5 to 10 carbon atoms having a substituent” As the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms”, specifically, a deuterium atom, a cyano group, a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group; Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as phenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl Group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuran Examples thereof include an aromatic heterocyclic group such as a nyl group, a dibenzothienyl group, and a carbolinyl group, and these substituents may be further substituted by the above-exemplified substituents.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、ｎ－プロピルオキシ基、イソプロピルオキシ基、ｎ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、１－アダマンチルオキシ基、２－アダマンチルオキシ基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent” represented by R 14 or R 15 in the general formula (1) or “having a substituent. Or a "C1-C6 linear or branched alkyloxy group" or "C5-C10 cycloalkyloxy group" in the "optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms". Specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Such as it is possible to increase the group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent” represented by R 14 or R 15 in the general formula (1) or “C5 to C having a substituent” Specific examples of the “substituent” in “10 cycloalkyloxy groups” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyloxy group, ethyloxy A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a propyloxy group; an alkenyl group such as an allyl group; an aryloxy group such as a phenyloxy group or a tolyloxy group; a benzyloxy group or a phenethyloxy group Arylalkyloxy groups such as a group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as entanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group Group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group, etc. And a group such as a group heterocyclic group, and these substituents may be further substituted by the above-exemplified substituents.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、およびカルボリニル基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 14 or R 15 in the general formula (1), or “substituted or unsubstituted condensed polycyclic group” Specific examples of the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthryl group. Group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, Indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group Pyrazolyl group include dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、トリフルオロメチル基、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；ベンジル基、ナフチルメチル基、フェネチル基などのアラルキル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基；ジメチルアミノ基、ジエチルアミノ基などのジアルキルアミノ基；ジフェニルアミノ基、ジナフチルアミノ基などの芳香族炭化水素基もしくは縮合多環芳香族基で置換されたジ置換アミノ基；ジベンジルアミノ基、ジフェネチルアミノ基などのジアラルキルアミノ基；ジピリジルアミノ基、ジチエニルアミノ基などの芳香族複素環基で置換されたジ置換アミノ基；ジアリルアミノ基などのジアルケニルアミノ基；アルキル基、芳香族炭化水素基、縮合多環芳香族基、アラルキル基、芳香族複素環基またはアルケニル基から選択される置換基で置換されたジ置換アミノ基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 As the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 14 and R 15 in the general formula (1), Specifically, deuterium atom, trifluoromethyl group, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, a linear or branched alkyl group having 1 to 6 carbon atoms such as n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group A linear or branched alkyloxy group having 1 to 6 carbon atoms such as ethyloxy group and propyloxy group; alkenyl group such as allyl group; benzyl group and naphthylmethyl Group, aralkyl group such as phenethyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl group, thienyl group, furyl group, pyrrolyl group, quinolyl Group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl Group, aromatic heterocyclic group such as carbolinyl group; aryl vinyl group such as styryl group and naphthyl vinyl group; acyl group such as acetyl group and benzoyl group; dialkylamino group such as dimethylamino group and diethylamino group; Disubstituted amino groups substituted with aromatic hydrocarbon groups such as dinaphthylamino groups or condensed polycyclic aromatic groups; Diaralkylamino groups such as dibenzylamino groups and diphenethylamino groups; Dipyridylamino groups and dithienylamino groups Disubstituted amino groups substituted with aromatic heterocyclic groups such as groups; dialkenylamino groups such as diallylamino groups; alkyl groups, aromatic hydrocarbon groups, condensed polycyclic aromatic groups, aralkyl groups, aromatic heterocyclic rings A group such as a disubstituted amino group substituted with a substituent selected from a group or an alkenyl group. These substituents may be further substituted by the above-exemplified substituents.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、具体的に、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、ナフチルオキシ基、アントリルオキシ基、フェナントリルオキシ基、フルオレニルオキシ基、インデニルオキシ基、ピレニルオキシ基、ペリレニルオキシ基などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 Specific examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R 14 and R 15 in the general formula (1) include a phenyloxy group, a biphenylyloxy group, a terfeny group. Examples thereof include a tolyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１４、Ｒ１５で表される「置換アリールオキシ基」における「置換基」としては、具体的に、重水素原子、トリフルオロメチル基、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；アリル基などのアルケニル基；ベンジル基、ナフチルメチル基、フェネチル基などのアラルキル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基；ジメチルアミノ基、ジエチルアミノ基などのジアルキルアミノ基；ジフェニルアミノ基、ジナフチルアミノ基などの芳香族炭化水素基もしくは縮合多環芳香族基で置換されたジ置換アミノ基；ジベンジルアミノ基、ジフェネチルアミノ基などのジアラルキルアミノ基；ジピリジルアミノ基、ジチエニルアミノ基などの芳香族複素環基で置換されたジ置換アミノ基；ジアリルアミノ基などのジアルケニルアミノ基；アルキル基、芳香族炭化水素基、縮合多環芳香族基、アラルキル基、芳香族複素環基またはアルケニル基から選択される置換基で置換されたジ置換アミノ基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していてもよい。
　また、これらの置換基が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 Specific examples of the “substituent” in the “substituted aryloxy group” represented by R 14 and R 15 in the general formula (1) include deuterium atom, trifluoromethyl group, cyano group, nitro group; fluorine Halogen atoms such as atoms, chlorine atoms, bromine atoms, iodine atoms; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, Linear or branched alkyl group having 1 to 6 carbon atoms such as neopentyl group and n-hexyl group; linear or branched alkyl group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group Alkyloxy groups; alkenyl groups such as allyl groups; aralkyl groups such as benzyl groups, naphthylmethyl groups, and phenethyl groups; phenyloxy groups Aryloxy groups such as tolyloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl Groups, fluoranthenyl groups, triphenylenyl groups and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl groups, thienyl groups, furyl groups, pyrrolyl groups, quinolyl groups, isoquinolyl groups, benzofuranyl groups, benzothienyl groups, indolyl groups Group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group and the like, styryl group, Aryl vinyl groups such as phthalyl vinyl; acyl groups such as acetyl and benzoyl groups; dialkylamino groups such as dimethylamino and diethylamino groups; aromatic hydrocarbon groups such as diphenylamino and dinaphthylamino groups; or condensed polycyclic aromatics Disubstituted amino groups substituted with aromatic groups; Diaralkylamino groups such as dibenzylamino groups and diphenethylamino groups; Disubstituted amino groups substituted with aromatic heterocyclic groups such as dipyridylamino groups and dithienylamino groups A dialkenylamino group such as a diallylamino group; a disubstituted group substituted with a substituent selected from an alkyl group, an aromatic hydrocarbon group, a condensed polycyclic aromatic group, an aralkyl group, an aromatic heterocyclic group or an alkenyl group; A group such as an amino group can be mentioned, and these substituents are further substituted by the substituents exemplified above. You may do it.
These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物は新規な化合物であり、従来の正孔輸送材料より、優れた電子の阻止能力を有し、優れたアモルファス性を有し、かつ薄膜状態が安定である。 The compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention is a novel compound, and has an excellent electron blocking ability than a conventional hole transport material, and an excellent amorphous And a thin film state is stable.
　本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物は、有機エレクトロルミネッセンス素子（以後、有機ＥＬ素子と略称する。）の正孔注入層および／または正孔輸送層の構成材料として使用することができる。従来の材料に比べて正孔の注入性が高く、移動度が大きく、電子阻止性が高く、しかも電子に対する安定性が高い材料を用いることによって、発光層内で生成した励起子を閉じ込めることができ、さらに正孔と電子が再結合する確率を向上させ、高発光効率を得ることができると共に、駆動電圧が低下して、有機ＥＬ素子の耐久性が向上するという作用を有する。 The compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention is a hole injection layer and / or a hole transport layer of an organic electroluminescence element (hereinafter abbreviated as an organic EL element). It can be used as a constituent material of the layer. By using a material with higher hole injection properties, higher mobility, higher electron blocking properties, and higher electron stability than conventional materials, it is possible to confine excitons generated in the light emitting layer. In addition, the probability of recombination of holes and electrons can be improved, high luminous efficiency can be obtained, the driving voltage is lowered, and the durability of the organic EL element is improved.
　本発明の一般式（１）で表される、フェナンスロアクリダン環構造を有する化合物は、有機ＥＬ素子の電子阻止層の構成材料としても使用することができる。優れた電子の阻止能力と共に従来の材料に比べて正孔輸送性に優れ、かつ薄膜状態の安定性の高い材料を用いることにより、高い発光効率を有しながら、駆動電圧が低下し、電流耐性が改善されて、有機ＥＬ素子の最大発光輝度が向上するという作用を有する。 The compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention can also be used as a constituent material of an electron blocking layer of an organic EL device. By using a material with excellent electron blocking ability and hole transportability compared to conventional materials and high stability in the thin film state, the driving voltage is lowered and current resistance is maintained while having high luminous efficiency. Is improved and the maximum light emission luminance of the organic EL element is improved.
　本発明の一般式（１）で表される、フェナンスロアクリダン環構造を有する化合物は、有機ＥＬ素子の発光層の構成材料としても使用することができる。従来の材料に比べて正孔輸送性に優れ、かつバンドギャップの広い本発明の材料を発光層のホスト材料として用い、ドーパントと呼ばれている蛍光発光体や燐光発光体を担持させて、発光層として用いることにより、駆動電圧が低下し、発光効率が改善された有機ＥＬ素子を実現できるという作用を有する。 The compound represented by the general formula (1) of the present invention and having a phenanthroacridan ring structure can also be used as a constituent material of a light emitting layer of an organic EL element. The material of the present invention, which has excellent hole transportability compared to conventional materials and has a wide band gap, is used as a host material for the light-emitting layer, and supports a fluorescent or phosphorescent emitter called a dopant to emit light. By using it as a layer, it has the effect | action that a drive voltage falls and can implement | achieve the organic EL element by which luminous efficiency was improved.
　本発明の有機ＥＬ素子は、従来の正孔輸送材料より正孔の移動度が大きく、優れた電子の阻止能力を有し、優れたアモルファス性を有し、かつ薄膜状態が安定な、フェナンスロアクリダン環構造を有する化合物を用いているため、高効率、高耐久性を実現することが可能となった。 The organic EL device of the present invention has higher hole mobility than conventional hole transport materials, excellent electron blocking ability, excellent amorphous property, and stable thin film state. Since a compound having a throacridan ring structure is used, high efficiency and high durability can be realized.
　本発明のフェナンスロアクリダン環構造を有する化合物は、有機ＥＬ素子の正孔注入層、正孔輸送層、電子阻止層あるいは発光層の構成材料として有用であり、優れた電子の阻止能力を有し、かつアモルファス性が良好であり、薄膜状態が安定で、耐熱性に優れている。本発明の有機ＥＬ素子は発光効率および電力効率が高く、このことにより素子の実用駆動電圧を低くさせることができ、耐久性を改良することができる。 The compound having a phenanthroacridan ring structure of the present invention is useful as a constituent material of a hole injection layer, a hole transport layer, an electron blocking layer or a light emitting layer of an organic EL device, and has an excellent electron blocking ability. And has good amorphous properties, a stable thin film state, and excellent heat resistance. The organic EL device of the present invention has high luminous efficiency and power efficiency, which can reduce the practical driving voltage of the device and improve the durability.
本発明実施例１の化合物（化合物４）の１Ｈ－ＮＭＲチャート図である。1 is a 1 H-NMR chart of the compound of Example 1 of the present invention (Compound 4). 本発明実施例２の化合物（化合物８）の１Ｈ－ＮＭＲチャート図である。FIG. 2 is a 1 H-NMR chart of the compound of Example 2 of the present invention (Compound 8). 実施例５、実施例６、比較例１のＥＬ素子構成を示した図である。FIG. 6 is a diagram showing EL element configurations of Example 5, Example 6, and Comparative Example 1.
　本発明のフェナンスロアクリダン環構造を有する化合物は新規な化合物であり、これらの化合物は例えば、以下のように合成できる。まず、相当する１０位をアリール基で置換されたフェナンスロアクリダンを臭素やＮ－ブロモスクシンイミドなどによるブロモ化を行うことによって、１３－ブロモ－１０－アリールフェナンスロアクリダンを合成し、このブロモ体と種々のジアリールアミンとをＢｕｃｈｗａｌｄ－Ｈａｒｔｗｉｇ反応などのクロスカップリング反応を行うことによって、フェナンスロアクリダン環構造を有する化合物を合成することができる。 The compound having a phenanthroacridan ring structure of the present invention is a novel compound, and these compounds can be synthesized, for example, as follows. First, 13-bromo-10-arylphenanthroacridane was synthesized by bromination of the corresponding 10-position substituted phenanthroacridane with an aryl group with bromine or N-bromosuccinimide, A compound having a phenanthroacridan ring structure can be synthesized by performing a cross-coupling reaction such as Buchwald-Hartwig reaction between this bromo compound and various diarylamines.
　また、本発明のフェナンスロアクリダン環構造を有する化合物は以下のようにも合成できる。まず、前記した１３－ブロモ－１０－アリールフェナンスロアクリダンと種々のジアリールアミンとをＵｌｌｍａｎｎ反応などのクロスカップリング反応（例えば、非特許文献５参照）を行うことによって、フェナンスロアクリダン環構造を有する化合物を合成することができる。 Further, the compound having a phenanthroacridan ring structure of the present invention can be synthesized as follows. First, the above-described 13-bromo-10-arylphenanthroacridan and various diarylamines are subjected to a cross-coupling reaction such as the Ullmann reaction (see, for example, Non-Patent Document 5) to thereby obtain a phenanthroacridan. A compound having a ring structure can be synthesized.
　さらに、本発明のフェナンスロアクリダン環構造を有する化合物は以下のようにも合成できる。前記した１３－ブロモ－１０－アリールフェナンスロアクリダンと種々のボロン酸またはボロン酸エステル（例えば、非特許文献６参照）とのＳｕｚｕｋｉカップリングなどのクロスカップリング反応（例えば、非特許文献７参照）を行うことによって、本発明のインデノアクリダン環構造を有する化合物を合成することができる。 Furthermore, the compound having a phenanthroacridan ring structure of the present invention can be synthesized as follows. Cross coupling reaction such as Suzuki coupling between the 13-bromo-10-arylphenanthroacridan and various boronic acids or boronic esters (for example, see Non-patent Document 6) (for example, Non-Patent Document 7) The compound having the indenoacridan ring structure of the present invention can be synthesized.
　一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Specific examples of preferable compounds among the compounds having a phenanthracridan ring structure represented by the general formula (1) are shown below, but the present invention is not limited to these compounds.
Figure JPOXMLDOC01-appb-C000016
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１）
Figure JPOXMLDOC01-appb-C000016
 (Compound 1)
Figure JPOXMLDOC01-appb-C000017
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物２)
Figure JPOXMLDOC01-appb-C000017
 (Compound 2)
Figure JPOXMLDOC01-appb-C000018
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物３)
Figure JPOXMLDOC01-appb-C000018
 (Compound 3)
Figure JPOXMLDOC01-appb-C000019
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４）
Figure JPOXMLDOC01-appb-C000019
 (Compound 4)
Figure JPOXMLDOC01-appb-C000020
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５）
Figure JPOXMLDOC01-appb-C000020
 (Compound 5)
Figure JPOXMLDOC01-appb-C000021
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物６）
Figure JPOXMLDOC01-appb-C000021
 (Compound 6)
Figure JPOXMLDOC01-appb-C000022
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物７）
Figure JPOXMLDOC01-appb-C000022
 (Compound 7)
Figure JPOXMLDOC01-appb-C000023
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物８)
Figure JPOXMLDOC01-appb-C000023
 (Compound 8)
Figure JPOXMLDOC01-appb-C000024
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物９)
Figure JPOXMLDOC01-appb-C000024
 (Compound 9)
Figure JPOXMLDOC01-appb-C000025
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１０）
Figure JPOXMLDOC01-appb-C000025
 (Compound 10)
Figure JPOXMLDOC01-appb-C000026
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１１）
Figure JPOXMLDOC01-appb-C000026
 (Compound 11)
Figure JPOXMLDOC01-appb-C000027
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１２）
Figure JPOXMLDOC01-appb-C000027
 (Compound 12)
Figure JPOXMLDOC01-appb-C000028
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１３）
Figure JPOXMLDOC01-appb-C000028
 (Compound 13)
Figure JPOXMLDOC01-appb-C000029
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物１４)
Figure JPOXMLDOC01-appb-C000029
 (Compound 14)
Figure JPOXMLDOC01-appb-C000030
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物１５)
Figure JPOXMLDOC01-appb-C000030
 (Compound 15)
Figure JPOXMLDOC01-appb-C000031
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物１６)
Figure JPOXMLDOC01-appb-C000031
 (Compound 16)
Figure JPOXMLDOC01-appb-C000032
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１７）
Figure JPOXMLDOC01-appb-C000032
 (Compound 17)
Figure JPOXMLDOC01-appb-C000033
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１８）
Figure JPOXMLDOC01-appb-C000033
 (Compound 18)
Figure JPOXMLDOC01-appb-C000034
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物１９）
Figure JPOXMLDOC01-appb-C000034
 (Compound 19)
Figure JPOXMLDOC01-appb-C000035
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物２０)
Figure JPOXMLDOC01-appb-C000035
 (Compound 20)
Figure JPOXMLDOC01-appb-C000036
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２１）
Figure JPOXMLDOC01-appb-C000036
 (Compound 21)
Figure JPOXMLDOC01-appb-C000037
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物２２)
Figure JPOXMLDOC01-appb-C000037
 (Compound 22)
Figure JPOXMLDOC01-appb-C000038
 　　　　　　　　　　　　　　　　　　　　　　　　　(化合物２３)
Figure JPOXMLDOC01-appb-C000038
 (Compound 23)
Figure JPOXMLDOC01-appb-C000039
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２４）
Figure JPOXMLDOC01-appb-C000039
 (Compound 24)
Figure JPOXMLDOC01-appb-C000040
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２５）
Figure JPOXMLDOC01-appb-C000040
 (Compound 25)
Figure JPOXMLDOC01-appb-C000041
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２６）
Figure JPOXMLDOC01-appb-C000041
 (Compound 26)
Figure JPOXMLDOC01-appb-C000042
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２７）
Figure JPOXMLDOC01-appb-C000042
 (Compound 27)
Figure JPOXMLDOC01-appb-C000043
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２８）
Figure JPOXMLDOC01-appb-C000043
 (Compound 28)
Figure JPOXMLDOC01-appb-C000044
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物２９）
Figure JPOXMLDOC01-appb-C000044
 (Compound 29)
Figure JPOXMLDOC01-appb-C000045
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３０）
Figure JPOXMLDOC01-appb-C000045
 (Compound 30)
Figure JPOXMLDOC01-appb-C000046
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３１）
Figure JPOXMLDOC01-appb-C000046
 (Compound 31)
Figure JPOXMLDOC01-appb-C000047
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３２）
Figure JPOXMLDOC01-appb-C000047
 (Compound 32)
Figure JPOXMLDOC01-appb-C000048
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３３）
Figure JPOXMLDOC01-appb-C000048
 (Compound 33)
Figure JPOXMLDOC01-appb-C000049
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３４）
Figure JPOXMLDOC01-appb-C000049
 (Compound 34)
Figure JPOXMLDOC01-appb-C000050
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３５）
Figure JPOXMLDOC01-appb-C000050
 (Compound 35)
Figure JPOXMLDOC01-appb-C000051
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３６）
Figure JPOXMLDOC01-appb-C000051
 (Compound 36)
Figure JPOXMLDOC01-appb-C000052
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３７）
Figure JPOXMLDOC01-appb-C000052
 (Compound 37)
Figure JPOXMLDOC01-appb-C000053
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３８）
Figure JPOXMLDOC01-appb-C000053
 (Compound 38)
Figure JPOXMLDOC01-appb-C000054
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物３９）
Figure JPOXMLDOC01-appb-C000054
 (Compound 39)
Figure JPOXMLDOC01-appb-C000055
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４０）
Figure JPOXMLDOC01-appb-C000055
 (Compound 40)
Figure JPOXMLDOC01-appb-C000056
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４１）
Figure JPOXMLDOC01-appb-C000056
 (Compound 41)
Figure JPOXMLDOC01-appb-C000057
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４２）
Figure JPOXMLDOC01-appb-C000057
 (Compound 42)
Figure JPOXMLDOC01-appb-C000058
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４３）
Figure JPOXMLDOC01-appb-C000058
 (Compound 43)
Figure JPOXMLDOC01-appb-C000059
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４４）
Figure JPOXMLDOC01-appb-C000059
 (Compound 44)
Figure JPOXMLDOC01-appb-C000060
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４５）
Figure JPOXMLDOC01-appb-C000060
 (Compound 45)
Figure JPOXMLDOC01-appb-C000061
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４６）
Figure JPOXMLDOC01-appb-C000061
 (Compound 46)
Figure JPOXMLDOC01-appb-C000062
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４７）
Figure JPOXMLDOC01-appb-C000062
 (Compound 47)
Figure JPOXMLDOC01-appb-C000063
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４８）
Figure JPOXMLDOC01-appb-C000063
 (Compound 48)
Figure JPOXMLDOC01-appb-C000064
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物４９）
Figure JPOXMLDOC01-appb-C000064
 (Compound 49)
Figure JPOXMLDOC01-appb-C000065
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５０）
Figure JPOXMLDOC01-appb-C000065
 (Compound 50)
Figure JPOXMLDOC01-appb-C000066
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５１）
Figure JPOXMLDOC01-appb-C000066
 (Compound 51)
Figure JPOXMLDOC01-appb-C000067
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５２）
Figure JPOXMLDOC01-appb-C000067
 (Compound 52)
Figure JPOXMLDOC01-appb-C000068
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５３）
Figure JPOXMLDOC01-appb-C000068
 (Compound 53)
Figure JPOXMLDOC01-appb-C000069
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５４）
Figure JPOXMLDOC01-appb-C000069
 (Compound 54)
Figure JPOXMLDOC01-appb-C000070
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５５）
Figure JPOXMLDOC01-appb-C000070
 (Compound 55)
Figure JPOXMLDOC01-appb-C000071
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５６）
Figure JPOXMLDOC01-appb-C000071
 (Compound 56)
Figure JPOXMLDOC01-appb-C000072
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５７）
Figure JPOXMLDOC01-appb-C000072
 (Compound 57)
Figure JPOXMLDOC01-appb-C000073
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５８）
Figure JPOXMLDOC01-appb-C000073
 (Compound 58)
　これらの化合物の精製はカラムクロマトグラフによる精製、シリカゲル、活性炭、活性白土などによる吸着精製、溶媒による再結晶や晶析法などによって行った。化合物の同定は、ＮＭＲ分析によって行った。物性値として、ガラス転移点（Ｔｇ）および仕事関数の測定を行った。ガラス転移点（Ｔｇ）は薄膜状態の安定性の指標となるものであり、仕事関数は正孔輸送性の指標となるものである。 These compounds were purified by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization using a solvent, crystallization method, and the like. The compound was identified by NMR analysis. As a physical property value, a glass transition point (Tg) and a work function were measured. The glass transition point (Tg) is an index of stability in a thin film state, and the work function is an index of hole transportability.
　ガラス転移点（Ｔｇ）は、粉体を用いて高感度示差走査熱量計（ブルカー・エイエックスエス製、ＤＳＣ３１００Ｓ）によって求めた。 The glass transition point (Tg) was determined with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S) using powder.
　仕事関数は、ＩＴＯ基板の上に１００ｎｍの薄膜を作製して、イオン化ポテンシャル測定装置（住友重機械工業株式会社製、ＰＹＳ－２０２）を用いて測定した。 The work function was measured using an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) after forming a 100 nm thin film on the ITO substrate.
　本発明の有機ＥＬ素子の構造としては、基板上に順次に、陽極、正孔輸送層、電子阻止層、発光層、電子輸送層、陰極からなるもの、また、陽極と正孔輸送層の間に正孔注入層を有するもの、電子輸送層と陰極の間に電子注入層を有するものがあげられる。これらの多層構造においては有機層を何層か省略することが可能であり、例えば基板上に順次に、陽極、正孔輸送層、発光層、電子輸送層、陰極を有する構成とすることもできる。 The structure of the organic EL device of the present invention includes an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on the substrate, and between the anode and the hole transport layer. And those having an electron injection layer between the electron transport layer and the cathode. In these multilayer structures, several organic layers can be omitted. For example, a structure having an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on a substrate can be used. .
　本発明の有機ＥＬ素子の陽極としては、ＩＴＯや金のような仕事関数の大きな電極材料が用いられる。本発明の有機ＥＬ素子の正孔注入層として、本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物のほか、銅フタロシアニンに代表されるポルフィリン化合物、スターバースト型のトリフェニルアミン誘導体、種々のトリフェニルアミン４量体などの材料、ヘキサシアノアザトリフェニレンのようなアクセプター性の複素環化合物や塗布型の高分子材料を用いることができる。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the anode of the organic EL element of the present invention, an electrode material having a large work function such as ITO or gold is used. As a hole injection layer of the organic EL device of the present invention, in addition to a compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, a porphyrin compound represented by copper phthalocyanine, a starburst type Materials such as triphenylamine derivatives, various triphenylamine tetramers, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
　本発明の有機ＥＬ素子の正孔輸送層として、本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物のほか、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（ｍ－トリル）ベンジジン（以後、ＴＰＤと略称する）やＮ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（α－ナフチル）ベンジジン（以後、ＮＰＤと略称する）、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラビフェニリルベンジジンなどのベンジジン誘導体、１，１－ビス［４－(ジ－４－トリルアミノ)フェニル］シクロヘキサン（以後、ＴＡＰＣと略称する）、種々のトリフェニルアミン３量体および４量体などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。また、正孔の注入・輸送層として、ポリ（３，４－エチレンジオキシチオフェン）（以後、ＰＥＤＯＴと略称する）／ポリ（スチレンスルフォネート）（以後、ＰＳＳと略称する）などの塗布型の高分子材料を用いることができる。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the hole transport layer of the organic EL device of the present invention, in addition to the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, N, N′-diphenyl-N, N′— Di (m-tolyl) benzidine (hereinafter abbreviated as TPD), N, N′-diphenyl-N, N′-di (α-naphthyl) benzidine (hereinafter abbreviated as NPD), N, N, N ′ Benzidine derivatives such as N, -tetrabiphenylylbenzidine, 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine trimers and 4 A mer may be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. In addition, as a hole injection / transport layer, a coating type such as poly (3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly (styrene sulfonate) (hereinafter abbreviated as PSS) is used. These polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
　また、正孔注入層あるいは正孔輸送層において、該層に通常使用される材料に対し、さらにトリスブロモフェニルアミンヘキサクロルアンチモンなどをＰドーピングしたものや、ＴＰＤの構造をその部分構造に有する高分子化合物などを用いることができる。 In addition, in the hole injection layer or the hole transport layer, a material that is usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony or the like, or a TPD structure having a partial structure. Molecular compounds and the like can be used.
　本発明の有機ＥＬ素子の電子阻止層として、本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物のほか、４，４’,４’’－トリ（Ｎ－カルバゾリル）トリフェニルアミン（以後、ＴＣＴＡと略称する）、９，９－ビス［４－（カルバゾール－９－イル）フェニル］フルオレン、１，３－ビス（カルバゾール－９－イル）ベンゼン（以後、ｍＣＰと略称する）、２，２－ビス（４－カルバゾール－９－イルフェニル）アダマンタン(以後、Ａｄ－Ｃｚと略称する)などのカルバゾール誘導体、９－［４－（カルバゾール－９－イル）フェニル］－９－［４－（トリフェニルシリル）フェニル］－９Ｈ－フルオレンに代表されるトリフェニルシリル基とトリアリールアミン構造を有する化合物などの電子阻止作用を有する化合物を用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the electron blocking layer of the organic EL device of the present invention, in addition to the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, 4,4 ′, 4 ″ -tri (N— Carbazolyl) triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis [4- (carbazol-9-yl) phenyl] fluorene, 1,3-bis (carbazol-9-yl) benzene (hereinafter mCP) Carbazole derivatives such as 2,2-bis (4-carbazol-9-ylphenyl) adamantane (hereinafter abbreviated as Ad-Cz), 9- [4- (carbazol-9-yl) phenyl] It has an electron blocking action such as a compound having a triphenylamine group represented by -9- [4- (triphenylsilyl) phenyl] -9H-fluorene and a triarylamine structure. That compound can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
　本発明の有機ＥＬ素子の発光層として、Ａｌｑ３をはじめとするキノリノール誘導体の金属錯体の他、各種の金属錯体、アントラセン誘導体、ビススチリルベンゼン誘導体、ピレン誘導体、オキサゾール誘導体、ポリパラフェニレンビニレン誘導体などを用いることができる。また、発光層をホスト材料とドーパント材料とで構成してもよく、ホスト材料として、本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物のほか、前記発光材料に加え、チアゾール誘導体、ベンズイミダゾール誘導体、ポリジアルキルフルオレン誘導体などを用いることができる。またドーパント材料としては、キナクリドン、クマリン、ルブレン、ペリレンおよびそれらの誘導体、ベンゾピラン誘導体、ローダミン誘導体、アミノスチリル誘導体などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。 As the light emitting layer of the organic EL device of the present invention, various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, etc., in addition to metal complexes of quinolinol derivatives including Alq 3 Can be used. The light emitting layer may be composed of a host material and a dopant material. As the host material, in addition to the compound having a phenanthroacridan ring structure represented by the general formula (1) of the present invention, the light emitting material In addition, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, and the like can be used. As the dopant material, quinacridone, coumarin, rubrene, perylene, and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
　また、発光材料として燐光発光材料を使用することも可能である。燐光発光材料としては、イリジウムや白金などの金属錯体の燐光発光体を使用することができる。Ｉｒ（ｐｐｙ）３などの緑色の燐光発光体、ＦＩｒｐｉｃ、ＦＩｒ６などの青色の燐光発光体、Ｂｔｐ２Ｉｒ（ａｃａｃ）などの赤色の燐光発光体などが用いられ、このときのホスト材料としては正孔注入・輸送性のホスト材料として４，４’－ジ（Ｎ－カルバゾリル）ビフェニル（以後、ＣＢＰと略称する）やＴＣＴＡ、ｍＣＰなどのカルバゾール誘導体などに加え、本発明の一般式（１）で表されるフェナンスロアクリダン環構造を有する化合物を用いることができる。電子輸送性のホスト材料として、ｐ－ビス（トリフェニルシリル）ベンゼン(以後、ＵＧＨ２と略称する)や２，２’,２’’－(１，３，５－フェニレン)－トリス（１－フェニル－１Ｈ－ベンズイミダゾール）（以後、ＴＰＢIと略称する）などを用いることができ、高性能の有機ＥＬ素子を作製することができる。 In addition, a phosphorescent material can be used as the light emitting material. As the phosphorescent material, a phosphorescent material of a metal complex such as iridium or platinum can be used. Green phosphorescent emitters such as Ir (ppy) 3 , blue phosphorescent emitters such as FIrpic and FIr6, and red phosphorescent emitters such as Btp 2 Ir (acac) are used as the host material. In addition to carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, mCP, etc. as a hole injection / transport host material, A compound having a phenanthroacridan ring structure represented can be used. As an electron transporting host material, p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ″-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) can be used, and a high-performance organic EL device can be produced.
　燐光性の発光材料のホスト材料へのドープは濃度消光を避けるため、発光層全体に対して1～３０重量パーセントの範囲で、共蒸着によってドープすることが好ましい。 In order to avoid concentration quenching, it is preferable to dope the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
　また、発光材料としてＰＩＣ－ＴＲＺ、ＣＣ２ＴＡ、ＰＸＺ－ＴＲＺ、４ＣｚＩＰＮなどのＣＤＣＢ誘導体などの遅延蛍光を放射する材料を使用することも可能である（例えば、非特許文献３参照）。 Moreover, it is also possible to use a material that emits delayed fluorescence such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN as the light emitting material (see, for example, Non-Patent Document 3).
　これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
　本発明の有機ＥＬ素子の正孔阻止層として、バソクプロイン（以後、ＢＣＰと略称する）などのフェナントロリン誘導体や、アルミニウム（III）ビス（２－メチル－８－キノリナート）－４－フェニルフェノレート（以後、ＢＡｌｑと略称する）などのキノリノール誘導体の金属錯体の他、各種の希土類錯体、トリアゾール誘導体、トリアジン誘導体、オキサジアゾール誘導体など、正孔阻止作用を有する化合物を用いることができる。これらの材料は電子輸送層の材料を兼ねてもよい。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the hole blocking layer of the organic EL device of the present invention, phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”). In addition to metal complexes of quinolinol derivatives such as BAlq), various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
　本発明の有機ＥＬ素子の電子輸送層として、Ａｌｑ３、ＢＡｌｑをはじめとするキノリノール誘導体の金属錯体のほか、各種金属錯体、トリアゾール誘導体、トリアジン誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、カルボジイミド誘導体、キノキサリン誘導体、フェナントロリン誘導体、シロール誘導体などを用いることができる。これらは、単独で成膜してもよいが、他の材料とともに混合して成膜した単層として使用してもよく、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層の積層構造としてもよい。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As an electron transport layer of the organic EL device of the present invention, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline, in addition to metal complexes of quinolinol derivatives including Alq 3 and BAlq. Derivatives, phenanthroline derivatives, silole derivatives and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
　本発明の有機ＥＬ素子の電子注入層として、フッ化リチウム、フッ化セシウムなどのアルカリ金属塩、フッ化マグネシウムなどのアルカリ土類金属塩、酸化アルミニウムなどの金属酸化物などを用いることができるが、電子輸送層と陰極の好ましい選択においては、これを省略することができる。 As the electron injection layer of the organic EL device of the present invention, an alkali metal salt such as lithium fluoride and cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, and a metal oxide such as aluminum oxide can be used. In the preferred selection of the electron transport layer and the cathode, this can be omitted.
　本発明の有機ＥＬ素子の陰極として、アルミニウムのような仕事関数の低い電極材料や、マグネシウム銀合金、マグネシウムインジウム合金、アルミニウムマグネシウム合金のような、より仕事関数の低い合金が電極材料として用いられる。 As the cathode of the organic EL device of the present invention, an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
　以下、本発明の実施の形態について、実施例により具体的に説明するが、本発明は、以下の実施例に限定されるものではない。 Hereinafter, embodiments of the present invention will be specifically described with reference to examples. However, the present invention is not limited to the following examples.
　＜１３－{（ビフェニル－４－イル）－フェニルアミノ}－１５，１５－ジメチル－１０－フェニル－１０，１５－ジヒドロフェナントロ[９，１０－ｂ]アクリジン（化合物４）の合成＞
　窒素置換した反応容器に、１３－ブロモ－１５，１５－ジメチル－１０－フェニル１０，１５－ジヒドロフェナントロ[９，１０－ｂ]アクリジン１２ｇ、（ビフェニル－４－イル）－フェニルアミン５．７ｇ、ｔｅｒｔ－ブトキシナトリウム２．７ｇ、酢酸パラジウム０．２４ｇ、トリ－ｔｅｒｔ－ブチルホスフィンの５０％（Ｗ／Ｖ）トルエン溶液０．４４ｍｌ、トルエン１２０ｍｌを加えて加熱し、９０℃で２時間撹拌した。反応液を減圧下濃縮した後、メタノールを用いた結晶化を行って粗製物を得た。粗製物をカラムクロマトグラフ（担体：シリカゲル、溶離液：ヘキサン／トルエン）を用いて精製した後、トルエンを用いた再結晶を行うことによって１３－{（ビフェニル－４－イル）－フェニルアミノ}－１５，１５－ジメチル－１０－フェニル１０，１５－ジヒドロフェナントロ[９，１０－ｂ]アクリジンの淡黄色粉体７．３ｇ（収率４６％）を得た。 <Synthesis of 13-{(biphenyl-4-yl) -phenylamino} -15,15-dimethyl-10-phenyl-10,15-dihydrophenanthro [9,10-b] acridine (Compound 4)>
Into a reaction vessel purged with nitrogen, 13 g of 13-bromo-15,15-dimethyl-10-phenyl 10,15-dihydrophenanthro [9,10-b] acridine, (biphenyl-4-yl) -phenylamine 7 g, tert-butoxy sodium 2.7 g, palladium acetate 0.24 g, tri-tert-butylphosphine 50% (W / V) toluene solution 0.44 ml and toluene 120 ml were added and heated, and stirred at 90 ° C. for 2 hours. did. The reaction solution was concentrated under reduced pressure and then crystallized using methanol to obtain a crude product. The crude product was purified using a column chromatograph (carrier: silica gel, eluent: hexane / toluene) and then recrystallized using toluene to obtain 13-{(biphenyl-4-yl) -phenylamino}- 7.3 g (yield 46%) of a pale yellow powder of 15,15-dimethyl-10-phenyl 10,15-dihydrophenanthro [9,10-b] acridine was obtained.
　得られた淡黄色粉体についてＮＭＲを使用して構造を同定した。１Ｈ－ＮＭＲ測定結果を図１に示した。 The structure of the obtained pale yellow powder was identified using NMR. The results of 1 H-NMR measurement are shown in FIG.
　１Ｈ－ＮＭＲ（ＴＨＦ－ｄ８）で以下の３８個の水素のシグナルを検出した。δ（ｐｐｍ）＝８．９２（１Ｈ）、８．９０－８．６５（３Ｈ）、８．０８（１Ｈ）、７．９６（２Ｈ）、７．８７－７．４５（１５Ｈ）、７．４３－７．２２（７Ｈ）、７．１４（１Ｈ）、６．９６（１Ｈ）、６．５２（１Ｈ）、１．９９（６Ｈ）。 The following 38 hydrogen signals were detected by 1 H-NMR (THF-d 8 ). δ (ppm) = 8.92 (1H), 8.90-8.65 (3H), 8.08 (1H), 7.96 (2H), 7.87-7.45 (15H), 7. 43-7.22 (7H), 7.14 (1H), 6.96 (1H), 6.52 (1H), 1.99 (6H).
　＜１３－{（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－フェニルアミノ}－１５，１５－ジメチル－１０－フェニル－１０，１５－ジヒドロフェナントロ[９，１０－ｂ]アクリジン（化合物８）の合成＞
　窒素置換した反応容器に、１３－ブロモ－１５，１５－ジメチル－１０－フェニル－１０，１５－ジヒドロフェナントロ[９，１０－ｂ]アクリジン１１ｇ、（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－フェニルアミン６．１ｇ、ｔｅｒｔ－ブトキシナトリウム２．５ｇ、酢酸パラジウム０．１ｇ、トリ－ｔｅｒｔ－ブチルホスフィンの５０％（Ｗ／Ｖ）トルエン溶液０．４１ｍｌ、トルエン１１０ｍｌを加えて加熱し、９０℃で３時間撹拌した。トルエンを加え、不溶物をろ過によって除いた後、減圧下で濃縮した。メタノールを用いた結晶化を行い、得られた粗製物をカラムクロマトグラフ（担体：シリカゲル、溶離液：ヘキサン／トルエン）を用いて精製した後、トルエンを用いた再結晶、ｎ－ヘキサンを用いた再結晶を行うことによって１３－{（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－フェニルアミノ}－１５，１５－ジメチル－１０－フェニル－１０，１５－ジヒドロフェナントロ[９，１０－ｂ]アクリジンの淡黄色粉体８．３ｇ（収率５４％）を得た。 <13-{(9,9-dimethyl-9H-fluoren-2-yl) -phenylamino} -15,15-dimethyl-10-phenyl-10,15-dihydrophenanthro [9,10-b] acridine Synthesis of (Compound 8)>
Into a reaction vessel purged with nitrogen, 11 g of 13-bromo-15,15-dimethyl-10-phenyl-10,15-dihydrophenanthro [9,10-b] acridine, (9,9-dimethyl-9H-fluorene- 2-yl) -phenylamine 6.1 g, tert-butoxy sodium 2.5 g, palladium acetate 0.1 g, tri-tert-butylphosphine 50% (W / V) toluene solution 0.41 ml and toluene 110 ml were added. Heated and stirred at 90 ° C. for 3 hours. Toluene was added and insolubles were removed by filtration, followed by concentration under reduced pressure. Crystallization using methanol was performed, and the resulting crude product was purified using column chromatography (carrier: silica gel, eluent: hexane / toluene), then recrystallized using toluene, and n-hexane was used. By recrystallization, 13-{(9,9-dimethyl-9H-fluoren-2-yl) -phenylamino} -15,15-dimethyl-10-phenyl-10,15-dihydrophenanthro [9, 8.3 g (yield 54%) of 10-b] acridine pale yellow powder was obtained.
　得られた淡黄色粉体についてＮＭＲを使用して構造を同定した。１Ｈ－ＮＭＲ測定結果を図２に示した。 The structure of the obtained pale yellow powder was identified using NMR. The results of 1 H-NMR measurement are shown in FIG.
　１Ｈ－ＮＭＲ（ＴＨＦ－ｄ８）で以下の４２個の水素のシグナルを検出した。δ（ｐｐｍ）＝８．９２（１Ｈ）、８．９０－８．６５（３Ｈ）、８．０８（１Ｈ）、７．９６（２Ｈ）、７．９２－７．５２（１２Ｈ）、７．４８－７．２３（７Ｈ）、７．２０－７．０３（２Ｈ）、６．９６（１Ｈ）、６．４９（１Ｈ）、１．９７（６Ｈ）、１．５７（６Ｈ）。 The following 42 hydrogen signals were detected by 1 H-NMR (THF-d 8 ). δ (ppm) = 8.92 (1H), 8.90-8.65 (3H), 8.08 (1H), 7.96 (2H), 7.92-7.52 (12H), 7. 48-7.23 (7H), 7.20-7.03 (2H), 6.96 (1H), 6.49 (1H), 1.97 (6H), 1.57 (6H).
　本発明の化合物について、高感度示差走査熱量計（ブルカー・エイエックスエス製、ＤＳＣ３１００Ｓ）によって融点とガラス転移点を求めた。
　　　　　　　　　　　　　　　　　　ガラス転移点
　本発明実施例１の化合物　　　　　　１３３℃
　本発明実施例２の化合物　　　　　　１４６℃ About the compound of this invention, melting | fusing point and the glass transition point were calculated | required with the highly sensitive differential scanning calorimeter (The product made from Bruker AXS, DSC3100S).
Glass transition point Compound of Example 1 of the present invention 133 ° C
Inventive Example 2 Compound 146 ° C.
　本発明の化合物は１００℃以上のガラス転移点を有しており、本発明の化合物において薄膜状態が安定であることを示すものである。 The compound of the present invention has a glass transition point of 100 ° C. or higher, which indicates that the thin film state is stable in the compound of the present invention.
　本発明の化合物を用いて、ＩＴＯ基板の上に膜厚１００ｎｍの蒸着膜を作製して、イオン化ポテンシャル測定装置（住友重機械工業株式会社製、ＰＹＳ－２０２）で仕事関数を測定した。
　　　　　　　　　　　　　　　　　　仕事関数
　本発明実施例１の化合物　　　　　５．４５ｅＶ
　本発明実施例２の化合物　　　　　５．３６ｅＶ
　ＮＰＤ　　　　　　　　　　　　　５．５４ｅＶ Using the compound of the present invention, a deposited film having a thickness of 100 nm was formed on an ITO substrate, and the work function was measured with an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).
Work function Compound of Example 1 of the present invention 5.45 eV
Compound of Example 2 of the present invention 5.36 eV
NPD 5.54eV
　このように本発明の化合物はＮＰＤ、ＴＰＤなどの一般的な正孔輸送材料がもつ仕事関数５．５ｅＶと比較して、好適なエネルギー準位を示しており、良好な正孔輸送能力を有していることが分かる。 As described above, the compound of the present invention exhibits a suitable energy level as compared with the work function of 5.5 eV which is possessed by general hole transport materials such as NPD and TPD, and has a good hole transport capability. You can see that
　有機ＥＬ素子は、図３に示すような、ガラス基板１上に透明陽極２としてＩＴＯ電極をあらかじめ形成したものの上に、正孔注入層３、正孔輸送層４、発光層５、電子輸送層６、電子注入層７、陰極（アルミニウム電極）８の順に蒸着して作製した。 The organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2 as shown in FIG. 6, an electron injection layer 7 and a cathode (aluminum electrode) 8 were deposited in this order.
　具体的には、膜厚１５０ｎｍのＩＴＯを成膜したガラス基板１を有機溶媒で洗浄した後に、酸素プラズマ処理にて表面を洗浄した。その後、このＩＴＯ電極付きガラス基板を真空蒸着機内に取り付け０．００１Ｐａ以下まで減圧した。続いて、透明陽極２を覆うように正孔注入層３として、下記構造式の化合物５９を膜厚２０ｎｍとなるように形成した。この正孔注入層３の上に、正孔輸送層４として本発明実施例１の化合物（化合物４）を膜厚４０ｎｍとなるように形成した。この正孔輸送層４の上に、発光層５として下記構造式の化合物６０と下記構造式の化合物６１を、蒸着速度比が化合物６０：化合物６１＝５：９５となる蒸着速度で二元蒸着を行い、膜厚３０ｎｍとなるように形成した。この発光層５の上に、電子輸送層６としてＡｌｑ３を膜厚３０ｎｍとなるように形成した。この電子輸送層６の上に、電子注入層７としてフッ化リチウムを膜厚０．５ｎｍとなるように形成した。最後に、アルミニウムを膜厚１５０ｎｍとなるように蒸着して陰極８を形成した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。 Specifically, the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, a compound 59 having the following structural formula was formed to a thickness of 20 nm as the hole injection layer 3 so as to cover the transparent anode 2. On this hole injection layer 3, the compound (compound 4) of Example 1 of the present invention was formed as a hole transport layer 4 so as to have a film thickness of 40 nm. On this hole transport layer 4, a compound 60 having the following structural formula and a compound 61 having the following structural formula are deposited as the light emitting layer 5 in a binary manner at a deposition rate such that the deposition rate ratio is compound 60: compound 61 = 5: 95. To form a film thickness of 30 nm. On this emitting layer 5 was formed to have the Alq 3 film thickness 30nm as an electron transport layer 6. On the electron transport layer 6, lithium fluoride was formed as the electron injection layer 7 so as to have a film thickness of 0.5 nm. Finally, aluminum was deposited to a thickness of 150 nm to form the cathode 8. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere.
　本発明の実施例１の化合物（化合物４）を使用して作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the organic EL device produced using the compound of Example 1 (Compound 4) of the present invention.
Figure JPOXMLDOC01-appb-C000074
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物５９）
Figure JPOXMLDOC01-appb-C000074
 (Compound 59)
Figure JPOXMLDOC01-appb-C000075
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物６０）
Figure JPOXMLDOC01-appb-C000075
 (Compound 60)
Figure JPOXMLDOC01-appb-C000076
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物６１）
Figure JPOXMLDOC01-appb-C000076
 (Compound 61)
　実施例５において、正孔輸送層４の材料として本発明実施例１の化合物（化合物４）に代えて本発明実施例２の化合物（化合物８）を膜厚４０ｎｍとなるように形成した以外は、同様の条件で有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 In Example 5, the compound (Compound 8) of Example 2 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 4) of Example 1 of the present invention as a material for the hole transport layer 4. An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.
［比較例１］
　比較のために、実施例５において、正孔輸送層４の材料として本発明実施例１の化合物（化合物４）に代えて下記構造式の化合物６２を膜厚４０ｎｍとなるように形成した以外は、同様の条件で有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 [Comparative Example 1]
For comparison, in Example 5, except that the compound of the following structural formula was formed to a film thickness of 40 nm instead of the compound of Example 1 of the present invention (Compound 4) as the material of the hole transport layer 4. An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.
Figure JPOXMLDOC01-appb-C000077
 　　　　　　　　　　　　　　　　　　　　　　　　　（化合物６２）
Figure JPOXMLDOC01-appb-C000077
 (Compound 62)
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
　表１に示す様に、電流密度１０ｍＡ／ｃｍ２の電流を流したときの駆動電圧は、化合物６２を用いた比較例１の素子の５．１７Ｖに対して、本発明の化合物４または８を用いた実施例５～６の素子では、４．７８～４．９８Ｖといずれも低電圧化した。また、電力効率においても、化合物６２を用いた比較例１の素子の５．４９ｌｍ／Ｗに対して、本発明の化合物４または８を用いた実施例５～６の素子では、６．１５～６．４８ｌｍ／Ｗといずれも大きく向上した。さらに、輝度、発光効率のいずれにおいても、化合物６２に対して本発明の化合物は向上した。 As shown in Table 1, the driving voltage when a current density of 10 mA / cm 2 was passed was 5.17 V of the device of Comparative Example 1 using Compound 62, and the compound 4 or 8 of the present invention was used. In the devices of Examples 5 to 6 used, the voltage was lowered to 4.78 to 4.98 V in all cases. In terms of power efficiency, the device of Examples 5 to 6 using the compound 4 or 8 of the present invention is 6.15 to 5.49 lm / W of the device of Comparative Example 1 using the compound 62. Both were greatly improved to 6.48 lm / W. Furthermore, the compound of the present invention was improved with respect to the compound 62 in both luminance and luminous efficiency.
　以上の結果から明らかなように、本発明のフェナンスロアクリダン環構造を有する化合物を用いた有機ＥＬ素子は、前記化合物６２を用いた有機ＥＬ素子と比較しても、輝度、発光効率や電力効率の向上や、実用駆動電圧の低下を達成できることがわかった。 As is clear from the above results, the organic EL device using the compound having a phenanthroacridan ring structure of the present invention has brightness, luminous efficiency, and the like even when compared with the organic EL device using the compound 62. It was found that an improvement in power efficiency and a decrease in practical driving voltage can be achieved.
　本発明のフェナンスロアクリダン環構造を有する化合物は、正孔輸送能力が高く、アモルファス性に優れており、薄膜状態が安定であるため、有機ＥＬ素子用の化合物として優れている。該化合物を用いて有機ＥＬ素子を作製することにより、高い輝度、発光効率および電力効率を得ることができると共に、実用駆動電圧を低下させることができ、耐久性を改善させることができる。例えば、家庭電化製品や照明の用途への展開が可能となった。 The compound having a phenanthroacridan ring structure of the present invention is excellent as a compound for an organic EL device because of its high hole transport ability, excellent amorphousness, and stable thin film state. By producing an organic EL element using the compound, high luminance, light emission efficiency, and power efficiency can be obtained, practical driving voltage can be lowered, and durability can be improved. For example, it has become possible to develop home appliances and lighting.
　１　ガラス基板
　２　透明陽極
　３　正孔注入層
　４　正孔輸送層
　５　発光層
　６　電子輸送層
　７　電子注入層
　８　陰極 DESCRIPTION OF SYMBOLS 1 Glass substrate 2 Transparent anode 3 Hole injection layer 4 Hole transport layer 5 Light emitting layer 6 Electron transport layer 7 Electron injection layer 8 Cathode

Claims (17)

  1. 　下記一般式（１）で表される、フェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000078
     　　　　　　　　　　　　　　　　　　　　　　　　　（１）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     A compound having a phenanthroacridan ring structure represented by the following general formula (1).
    Figure JPOXMLDOC01-appb-C000078
     (1)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
  2. 　下記一般式（１ａ）で表される、請求項１記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000079
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 1 represented by the following general formula (1a).
    Figure JPOXMLDOC01-appb-C000079
     (1a)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
  3. 　下記一般式（１ｂ）で表される、請求項１記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000080
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 1 represented by the following general formula (1b).
    Figure JPOXMLDOC01-appb-C000080
     (1b)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
  4. 　下記一般式（１－１）で表される、請求項１記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000081
     　　　　　　　　　　　　　　　　　　　　　　　　　（１－１）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 1, which is represented by the following general formula (1-1).
    Figure JPOXMLDOC01-appb-C000081
     (1-1)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
  5. 　下記一般式（１ａ－１）で表される、請求項４記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000082
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ－１）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 4, which is represented by the following general formula (1a-1).
    Figure JPOXMLDOC01-appb-C000082
     (1a-1)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
  6. 　下記一般式（１ｂ－１）で表される、請求項４記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000083
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ－１）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表し、Ｂは置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または芳香族炭化水素基、芳香族複素環基もしくは縮合多環芳香族基から選ばれる基によって置換されたジ置換アミノ基を表す。Ａｒ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＢは単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 4, which is represented by the following general formula (1b-1).
    Figure JPOXMLDOC01-appb-C000083
     (1b-1)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and B represents a substituted group. Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aroma Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic group, which is substituted with a group selected from the group of groups Represents an aromatic group, and R 1 to R 13 may be the same or different from each other, and may be a hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, or optionally substituted carbon. 1 to 1 atom 6 linear or branched alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain having 2 to 6 carbon atoms A straight or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent or a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. And may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and R 14 and R 15 may be the same or different from each other. The A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent. A linear or branched alkenyl group having 2 to 6 carbon atoms, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a substituent An optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or A substituted or unsubstituted aryloxy group, R 14 and R 15 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Here, when A is a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and B are a single bond or May be bonded to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. )
  7. 　下記一般式（１－２）で表される、請求項１記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000084
     　　　　　　　　　　　　　　　　　　　　　　　　　（１－２）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表す。Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＡｒ２は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 1, which is represented by the following general formula (1-2).
    Figure JPOXMLDOC01-appb-C000084
     (1-2)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond. Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other. A hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom R 14 and R 15 may be the same as or different from each other, and may be a straight chain having 1 to 6 carbon atoms which may have a substituent or Min Alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain or branched alkenyl groups having 2 to 6 carbon atoms A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 14 and R 15 May be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, wherein A is a substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted In the case of an unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and Ar 2 are bonded via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be combined with each other to form a ring. )
  8. 　下記一般式（１ａ－２）で表される、請求項７記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000085
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ－２）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表す。Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＡｒ２は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 7, which is represented by the following general formula (1a-2).
    Figure JPOXMLDOC01-appb-C000085
     (1a-2)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond. Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other. A hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom R 14 and R 15 may be the same as or different from each other, and may be a straight chain having 1 to 6 carbon atoms which may have a substituent or Min Alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain or branched alkenyl groups having 2 to 6 carbon atoms A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 14 and R 15 May be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, wherein A is a substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted In the case of an unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and Ar 2 are bonded via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be combined with each other to form a ring. )
  9. 　下記一般式（１ｂ－２）で表される、請求項７記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000086
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ－２）
    （式中、Ａは置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基、もしくは単結合を表す。Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。ここで、Ａが置換もしくは無置換の芳香族炭化水素、置換もしくは無置換の芳香族複素環または置換もしくは無置換の縮合多環芳香族の２価基である場合、ＡとＡｒ２は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 7, represented by the following general formula (1b-2).
    Figure JPOXMLDOC01-appb-C000086
     (1b-2)
    (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond. Ar 1 , Ar 2 and Ar 3 may be the same or different from each other and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. Ar 2 and Ar 3 may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom or sulfur atom, and R 1 to R 13 may be the same or different from each other. A hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, a substituent Have a group An optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted straight chain or branched alkenyl group having 2 to 6 carbon atoms, and an optionally substituted carbon Straight or branched alkyloxy group having 1 to 6 atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom R 14 and R 15 may be the same as or different from each other, and may be a straight chain having 1 to 6 carbon atoms which may have a substituent or Min Alkyl groups, optionally substituted cycloalkyl groups having 5 to 10 carbon atoms, and optionally substituted straight chain or branched alkenyl groups having 2 to 6 carbon atoms A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted Or an unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, wherein R 14 and R 15 May be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, wherein A is a substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted In the case of an unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group, A and Ar 2 are bonded via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be combined with each other to form a ring. )
  10. 　下記一般式（１－３）で表される、請求項１記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000087
     　　　　　　　　　　　　　　　　　　　　　　　　　（１－３）
    （式中、Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 1, which is represented by the following general formula (1-3).
    Figure JPOXMLDOC01-appb-C000087
     (1-3)
    (In the formula, Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group. represents polycyclic aromatic group, Ar 2 and Ar 3 represents a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom bonded to each other via a to good .R 1 ~ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, a single bond, a substituted or unsubstituted methylene group, R 14 and R 15 may be the same or different from each other and may have a substituent, and may have a substituent, from 1 to 6 carbon atoms. A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or A branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cyclocarbon having 5 to 10 carbon atoms which may have a substituent; An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  11. 　下記一般式（１ａ－３）で表される、請求項１０記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000088
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ａ－３）
    （式中、Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 10, represented by the following general formula (1a-3).
    Figure JPOXMLDOC01-appb-C000088
     (1a-3)
    (In the formula, Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group. represents polycyclic aromatic group, Ar 2 and Ar 3 represents a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom bonded to each other via a to good .R 1 ~ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, a single bond, a substituted or unsubstituted methylene group, R 14 and R 15 may be the same or different from each other and may have a substituent, and may have a substituent, from 1 to 6 carbon atoms. A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or A branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cyclocarbon having 5 to 10 carbon atoms which may have a substituent; An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  12. 　下記一般式（１ｂ－３）で表される、請求項１０記載のフェナンスロアクリダン環構造を有する化合物。
    Figure JPOXMLDOC01-appb-C000089
     　　　　　　　　　　　　　　　　　　　　　　　　　（１ｂ－３）
    （式中、Ａｒ１、Ａｒ２、Ａｒ３は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ２とＡｒ３は単結合もしくは、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１～Ｒ１３は相互に同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。Ｒ１４、Ｒ１５は相互に同一でも異なってもよく、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基であって、Ｒ１４とＲ１５は単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。）     The compound having a phenanthroacridan ring structure according to claim 10, represented by the following general formula (1b-3).
    Figure JPOXMLDOC01-appb-C000089
     (1b-3)
    (In the formula, Ar 1 , Ar 2 and Ar 3 may be the same or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed group. represents polycyclic aromatic group, Ar 2 and Ar 3 represents a single bond or a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom bonded to each other via a to good .R 1 ~ to form a ring R 13 may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight chain having 1 to 6 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms Group, with substituent A linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic group A hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, a single bond, a substituted or unsubstituted methylene group, R 14 and R 15 may be the same or different from each other and may have a substituent, and may have a substituent, from 1 to 6 carbon atoms. A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or A branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cyclocarbon having 5 to 10 carbon atoms which may have a substituent; An alkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, R 14 and R 15 may combine with each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  13. 　一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機エレクトロルミネッセンス素子において、前記請求項１に記載のフェナンスロアクリダン環構造を有する化合物が、少なくとも１つの有機層の構成材料として用いられていることを特徴とする有機エレクトロルミネッセンス素子。 In the organic electroluminescence device having at least one organic layer sandwiched between a pair of electrodes, the compound having a phenanthroacridan ring structure according to claim 1 is used as a constituent material of at least one organic layer. An organic electroluminescence device characterized by being used.
  14. 　前記した有機層が正孔輸送層である請求項１３記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to claim 13, wherein the organic layer is a hole transport layer.
  15. 　前記した有機層が電子阻止層である請求項１３記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to claim 13, wherein the organic layer is an electron blocking layer.
  16. 　前記した有機層が正孔注入層である請求項１３記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to claim 13, wherein the organic layer is a hole injection layer.
  17. 　前記した有機層が発光層である請求項１３記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 13, wherein the organic layer is a light emitting layer.
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