WO2017221974A1 - Triazine compound, method for producing same, and organic electroluminescent element which comprises same as constituent - Google Patents

Triazine compound, method for producing same, and organic electroluminescent element which comprises same as constituent Download PDF

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WO2017221974A1
WO2017221974A1 PCT/JP2017/022826 JP2017022826W WO2017221974A1 WO 2017221974 A1 WO2017221974 A1 WO 2017221974A1 JP 2017022826 W JP2017022826 W JP 2017022826W WO 2017221974 A1 WO2017221974 A1 WO 2017221974A1
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group
pyridyl
phenyl
carbon atoms
phenyl group
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PCT/JP2017/022826
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French (fr)
Japanese (ja)
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服部一希
新井信道
田中剛
野村桂甫
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東ソー株式会社
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Priority to KR1020187037357A priority Critical patent/KR102424486B1/en
Priority to CN201780039272.4A priority patent/CN109311844B/en
Publication of WO2017221974A1 publication Critical patent/WO2017221974A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a triazine compound, a method for producing the same, and an organic electroluminescent device containing the triazine compound. More specifically, the present invention relates to a triazine compound useful as a material for an organic electroluminescence device, characterized by a structure in which a diarylpyridyl group is combined with a triazine skeleton via a meta bond or an ortho bond, and a method for producing the same. The present invention relates to an organic electroluminescence device having high efficiency, low voltage, and high durability, characterized by being used in at least one layer.
  • An organic electroluminescent device has a basic structure in which a light-emitting layer containing a light-emitting material is sandwiched between a hole transport layer and an electron transport layer, and an anode and a cathode are attached to the outside, and holes injected into the light-emitting layer And a light-emitting element that utilizes light emission (fluorescence or phosphorescence) when excitons generated by electron recombination are deactivated, and are already used for applications such as large televisions and lighting as well as small displays. .
  • the hole transport layer is a hole transport layer and a hole injection layer
  • the light emitting layer is an electron block layer
  • the electron transport layer is an electron transport layer and an electron injection layer. In some cases, it may be divided. In some cases, a co-deposited film doped with a metal, an organometallic compound, or another organic compound may be used as the carrier transport layer (electron transport layer or hole transport layer) of the organic electroluminescence device.
  • organic electroluminescent elements have a higher driving voltage than inorganic light emitting diodes, have low luminance and luminous efficiency, have extremely low element lifetime, and have not been put into practical use.
  • recent organic electroluminescence devices have been gradually improved, further excellent materials are demanded in terms of luminous efficiency characteristics, driving voltage characteristics, and long life characteristics.
  • high heat resistance may be required depending on applications such as in-vehicle applications, and the material is required to have a high glass transition temperature (Tg).
  • Examples of the electron transport material having excellent long life for organic electroluminescence devices include the triazine compound disclosed in Patent Document 1. However, further improvements have been demanded in terms of voltage, lifetime and luminous efficiency of organic electroluminescent devices using such materials.
  • Patent Document 2 discloses a triazine compound having a diarylpyridyl group. The compound is excellent in terms of increasing the luminous efficiency of the organic electroluminescent device, but further improvement in luminous efficiency has been demanded.
  • An object of the present invention is to provide an electron transport material which is excellent in heat resistance of film quality and excellent in low voltage drive performance, light emission efficiency or long life of an organic electroluminescence device.
  • triazine compound (1) a triazine compound in which a diarylpyridyl group and a triazine moiety are bonded via a meta bond or an ortho bond.
  • the organic electroluminescence device using the compound as an electron transporting material has a lower voltage, higher luminous efficiency, or longer life than when a conventionally known material is used. As a result, the present invention has been completed.
  • the present invention has the general formula (1)
  • Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same.
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring.
  • a monocyclic or condensed nitrogen-containing heteroaromatic group (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S
  • An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
  • Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
  • the total number of ring carbon atoms of Ar 2 , Ar 3 , and Ar 4 and the total number of ring carbon atoms of Ar 5 , Ar 6 , and Ar 7 are all 5 to 25.
  • A represents a single bond.
  • B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
  • Z 1 and Z 2 each independently represents a nitrogen atom or C—H. However, either Z 1 or Z 2 represents a nitrogen atom, and the other represents C—H.
  • a method for producing the triazine compound, and an organic electroluminescent device using the triazine compound is a method for producing the triazine compound, and an organic electroluminescent device using the triazine compound.
  • a triazine compound represented by the general formula (1) [2] Ar 1 is a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group, a triazine compound according to the two Ar 1 are the same [1]. [3] The triazine compound according to [1] or [2], wherein Ar 1 is a phenyl group. [4] Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b ′) only from a 6-membered ring.
  • a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms (c) a monocyclic ring having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S Or a condensed ring heteroaromatic group (the groups represented by (a), (b ′), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, and a carbon number of 1 to 4 Or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 are each independently (a) 6 to 24 carbon atoms.
  • a monocyclic or condensed aromatic hydrocarbon group (b ′) a monocyclic ring having 3 to 11 carbon atoms consisting of only a 6-membered ring, or A ring nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of H, C, O, and S (the ( The groups represented by a), (b ′) and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoran.
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoran.
  • the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenyl group, Nantrylphenyl group, fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzo Furylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzothi
  • the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenyl group, Nantrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl [1], [2], [3], which is a phenyl group, a bipyridyl group, a naphthyl group,
  • Either one of the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenyl group, Nantrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl A phenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group,
  • Either of the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenoxy group, Nantrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl A phenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a di
  • the present invention it is possible to provide a triazine compound excellent in heat resistance of film quality, and it is possible to provide an organic electroluminescence device excellent in low voltage, light emission efficiency, or long life.
  • the present invention relates to the triazine compound (1), a method for producing the same, and providing an organic electroluminescent element material using the material.
  • Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same. .
  • the phenyl group or naphthyl group substituted with a fluorine atom in Ar 1 is not particularly limited. A preferred example is given.
  • a phenyl group substituted with a methyl group or a naphthyl group in Ar 1 is not particularly limited, but a tolyl group, a methylnaphthyl group, a dimethylphenyl group, a dimethylnaphthyl group, and the like are preferable examples.
  • a phenyl group substituted with a phenyl group or a naphthyl group in Ar 1 is not particularly limited, and preferred examples include a biphenyl group, a phenylnaphthyl group, a terphenyl group, or a diphenylnaphthyl group.
  • Ar 1 is more preferably a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group from the viewpoint of excellent electron transporting material characteristics, and more preferably a phenyl group from the viewpoint of easy synthesis.
  • Ar 1 include, but are not limited to, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, Mesityl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, biphenyl-2-yl group, biphenyl-3-yl group Biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4- Yl group, 2 ', 4', 6'-trimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl
  • a phenyl group, a p-tolyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is preferable because of excellent electron transporting material characteristics.
  • a phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is more preferable.
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring.
  • a monocyclic or condensed nitrogen-containing heteroaromatic group (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S
  • An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 may be the same or different.
  • the (a) monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited, but includes a phenyl group, a naphthyl group, Preferable examples include phenanthryl group, anthryl group, pyrenyl group, triphenylenyl group, chrycenyl group, fluoranthenyl group, acenaphthyl group, fluorenyl group, or benzofluorenyl group.
  • these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
  • the (b) monocyclic or condensed ring-containing nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited.
  • Pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazyl group, quinolyl group, isoquinolyl group, phenanthridyl group, benzoquinolyl group, acridinyl group and the like are preferable examples.
  • the carbazolyl group is a heteroaromatic group containing a 5-membered ring, and is not included in the monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only the 6-membered ring of the present invention. Further, as described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
  • (C) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of H, C, O, and S in Ar 2 , Ar 3 , Ar 5 , and Ar 6
  • the group is not particularly limited, and preferred examples include a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, or a dibenzofuryl group.
  • these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
  • the alkyl group having 1 to 4 carbon atoms in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited, but a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, Alternatively, a t-butyl group and the like are preferable examples.
  • the alkoxy group having 1 to 4 carbon atoms in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited, but is not limited to methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n- Preferred examples include a butoxy group or a t-butoxy group.
  • Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
  • Ar 4 and Ar 7 (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a monocyclic or condensed ring-containing nitrogen having 3 to 25 carbon atoms consisting of only a 6-membered ring.
  • a heteroaromatic group (c) a monocyclic or condensed ring heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S, and having 1 to 4 carbon atoms
  • the constituent requirements for the alkyl group and the alkoxy group having 1 to 4 carbon atoms are all synonymous with Ar 2 , Ar 3 , Ar 5 , and Ar 6 .
  • the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are not particularly limited, but for example, Without limitation, for example, phenyl group, biphenyl group, terphenyl group, naphthylphenyl group, phenanthrylphenyl group, anthrylphenyl group, pyrenylphenyl group, triphenylphenyl group, chrysenylphenyl group, Fluoranthenylphenyl group, acenaphthylphenyl group, fluorenylphenyl group, naphthylbiphenyl group, naphthyl group, phenylnaphthyl group, biphenylnaphthyl group, phenanthrylnaphthyl group, anthrylnaphthyl group, phenanthryl group, phenylphenan
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms in terms of excellent electron transporting material characteristics.
  • B ′ a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only a 6-membered ring, and (c) an atom selected from an atomic group consisting of H, C, O, and S
  • a C3-C25 monocyclic or condensed heteroaromatic group (the groups represented by (a), (b ′), and (c) are phenyl, tolyl, pyridyl, methylpyridyl, A fluorine atom, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond
  • Ar 4 and Ar 7 Are each independently (a) a monocyclic or condensed aromatic carbon
  • a basic group (b ′) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only a 6-membered ring, or (c) an atomic group consisting of H, C, O, and S
  • the preferred range is composed of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (c) an atom selected from an atomic group consisting of H, C, O, and S.
  • the monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms, the alkyl group having 1 to 4 carbon atoms, and the alkoxy group having 1 to 4 carbon atoms have the same meaning as described above.
  • a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only a 6-membered ring is not particularly limited, but includes a pyridyl group and a pyrazyl group.
  • a pyrimidyl group, a pyridazyl group, a triazyl group, a quinolyl group, an isoquinolyl group, and the like are preferable examples.
  • the carbazolyl group is a heteroaromatic group having 12 carbon atoms, and is not included in the monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only the 6-membered ring of the present invention. Further, as described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, because they are excellent in electron transporting material properties.
  • the group may have a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond More preferably, and Ar 4 and Ar 7 are each independently a phenyl group , Naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylen
  • Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group because they are easily synthesized.
  • perylenyl group fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups More preferably a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7.
  • the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently phenyl in terms of excellent electron transporting material characteristics.
  • the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are easy to synthesize and have high heat resistance of film quality.
  • Either the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl.
  • any one of the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is a phenyl group, a biphenyl group, a naphthylphenyl group, Phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzo Furylphenyl, bipyridyl, naphthyl, phenanthryl, dibenzothienyl, or Benzofuryl group (these groups may be substituted with a methyl group), more preferably the
  • Specific examples of the group represented by the formula are not particularly limited, and examples thereof include a phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5 -Dimethylphenyl group, mesityl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3- Propylphenyl group, 4-propylphenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4- Diiso
  • A represents a single bond.
  • B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
  • One of Z 1 and Z 2 represents a nitrogen atom, and the other represents C—H.
  • the compound represented by the general formula (1) can also be expressed as a compound represented by the general formula (1a) or (1b) as follows.
  • the triazine compound (1) of the present invention When used as a part of the components of the organic electroluminescent device, effects such as high luminous efficiency, long life, and low voltage can be obtained. In particular, this effect is prominent when used as an electron transport layer.
  • the light emitting layer in an organic electroluminescent element refers to a layer that emits light when a current is passed through an electrode composed of a cathode and an anode. Specifically, it refers to a layer containing a fluorescent compound that emits light when an electric current is passed through an electrode composed of a cathode and an anode.
  • an organic electroluminescent element has a structure in which a light emitting layer is sandwiched between a pair of electrodes.
  • the organic electroluminescent device of the present invention has a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer, etc. in addition to the light emitting layer as required, and has a structure sandwiched between a cathode and an anode. Specific examples include the structures shown below.
  • anode / light emitting layer / cathode ii) Anode / hole transport layer / light emitting layer / cathode (iii) Anode / light emitting layer / electron transport layer / cathode (iv) anode / hole transport layer / light emitting layer / electron Transport layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode buffer layer / cathode
  • a method for forming the light emitting layer for example, there is a method of forming a thin film by a known method such as a vapor deposition method, a spin coating method, a casting method, or an LB method.
  • the light emitting layer can be obtained by dissolving a light emitting material in a solvent together with a binder such as a resin to form a solution and then applying the solution by a spin coating method to form a thin film.
  • the film thickness of the light emitting layer thus formed is not particularly limited and can be appropriately selected according to the situation, but is usually in the range of 5 nm to 5 ⁇ m.
  • the hole injection layer and the hole transport layer have a function of transmitting the holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer are interposed between the anode and the light emitting layer. Thus, many holes are injected into the light emitting layer with a lower electric field.
  • electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light-emitting layer are generated by the electron barrier existing at the interface between the light-emitting layer and the hole injection layer or the hole transport layer. It accumulates at the interface in the light emitting layer without leaking into the injection layer or the hole transport layer, resulting in an element with excellent light emitting performance such as improved luminous efficiency.
  • the hole injecting material and the hole transporting material have either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • Examples of the hole injection material and hole transport material include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazoles.
  • Derivatives styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the hole injecting material and the hole transporting material those described above can be used, and porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds can be used. preferable.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′.
  • inorganic compounds such as p-type-Si and p-type-SiC can be used as the hole injection material and the hole transport material.
  • the hole injection layer and the hole transport layer are formed by thinning the hole injection material and the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Can be formed.
  • the film thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m.
  • the hole injection layer and hole transport layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the electron transport layer contains a triazine compound represented by the general formula (1).
  • the electron transport layer may be formed by forming the triazine compound represented by the general formula (1) by a known thin film forming method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. it can.
  • the thickness of the electron transport layer is not particularly limited, but is usually selected in the range of 5 nm to 5 ⁇ m.
  • this electron transport layer contains a triazine compound represented by the general formula (1), may contain a conventionally known electron transport material, and may have a single-layer structure composed of one kind or two or more kinds. Alternatively, a laminated structure composed of a plurality of layers having the same composition or different compositions may be used.
  • the light emitting material is not limited to the light emitting layer, but may be contained in the hole transport layer or the electron transport layer adjacent to the light emitting layer.
  • the luminous efficiency can be increased.
  • the substrate that is preferably used in the organic electroluminescent device of the present invention is not particularly limited in the type of glass, plastic, etc., and is not particularly limited as long as it is transparent.
  • Examples of the substrate preferably used in the organic electroluminescence device of the present invention include glass, quartz, and a light transmissive plastic film.
  • the light transmissive plastic film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate (PC). And a film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP), or the like.
  • a preferred example of producing the organic electroluminescence device of the present invention will be described.
  • a method for producing an organic electroluminescent element composed of the anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode will be described.
  • a thin film made of a desired electrode material for example, an anode material
  • a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm.
  • An anode is produced.
  • a thin film comprising a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer / electron injection layer, which is a device material, is formed thereon.
  • a buffer layer (electrode interface layer) may exist between the anode and the light emitting layer or the hole injection layer and between the cathode and the light emitting layer or the electron injection layer.
  • a layer having other functions may be laminated as necessary.
  • a functional layer such as a hole blocking layer or an electron blocking layer may be provided.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • an electrode substance include a conductive transparent material such as a metal such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • the anode may be formed by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by photolithography, or the pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering. May be formed.
  • the cathode those using an electrode substance of a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof are preferably used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this from the viewpoint of durability against electron injecting and oxidation for example, a magnesium / silver mixture, magnesium
  • An aluminum / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, and the like are preferable.
  • the cathode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering.
  • a thin film made of a desired electrode material for example, an anode material
  • a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm.
  • a thin film made of a substance is formed by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm, and a cathode is provided to obtain a desired organic electroluminescence device.
  • the organic electroluminescence device of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • the triazine compound (1) of the present invention has the following reaction formula (1) in the presence or absence of a base and in the presence of a palladium catalyst.
  • Y represents a leaving group and is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, an iodine atom, and a triflate.
  • a bromine atom or a chlorine atom is preferable in terms of a good reaction yield.
  • Y 1 and Y 2 one of Y 1 or Y 2 is the same meaning as Y, the other represents a hydrogen atom.
  • Each M independently represents ZnR 1 , MgR 2 , Sn (R 3 ) 3 or B (OR 4 ) 2 .
  • R ⁇ 1 > and R ⁇ 2 > represents a chlorine atom, a bromine atom, or an iodine atom each independently
  • R ⁇ 3 > represents a C1-C4 alkyl group or a phenyl group
  • R ⁇ 4 > is a hydrogen atom, carbon number 1 It represents an alkyl group or a phenyl group 4
  • B (oR 4) 2 two R 4 2 may be the same or different. Further, two R 4 may form a ring containing an oxygen atom and a boron atom together.
  • ZnR 1 and MgR 2 examples include ZnCl, ZnBr, ZnI, MgCl, MgBr, and MgI.
  • Sn (R 3 ) 3 examples include Sn (Me) 3 and Sn (Bu) 3 .
  • B (OR 4 ) 2 examples include B (OH) 2 , B (OMe) 2 , B (O i Pr) 2 , and B (OBu) 2 .
  • B (OR 4 ) 2 in the case where two R 4 are combined to form a ring containing an oxygen atom and a boron atom include the following (C-1) to (C-6): The group shown can be exemplified, and the group shown by (C-2) is desirable from the viewpoint of good yield.
  • one of the M 1 or M 2 is the same as defined above M, the other represents a hydrogen atom.
  • the compound (3) used in the reaction formula (1) is, for example, disclosed in JP-A-2005-268199, [0105] to [0121], JP-A-2008-280330, [0061] to [0076], or JP-A-2001-2001. It can be produced by combining the methods disclosed in Japanese Patent No. 335516 [0047] to [0082].
  • Examples of the compound (3) include the following (B-1) to (B-56), but the present invention is not limited to these.
  • the compound (5) used in the reaction formula (2) represents a compound in which M 1 and M 2 of the compound (3) are replaced with Y 1 and Y 2 , respectively.
  • Specific examples of the compound (5) include those in which M is replaced with Y in the above (B-1) to (B-56), but the present invention is not limited thereto.
  • the definitions of M 1 , M 2 , Y 1 , Y 2 , M, and Y are as described above. Can be illustrated.
  • Step 1 is a method in which the compound (2) is reacted with the compound (3) in the presence or absence of a base in the presence of a palladium catalyst to obtain the triazine compound (1) of the present invention.
  • reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the target product can be obtained in high yield.
  • Examples of the palladium catalyst that can be used in “Step 1” include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, and the like. Furthermore, ⁇ -allyl palladium chloride dimer, palladium acetylacetonate, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro (1,1′-bis (diphenylphosphine). Examples include complex compounds such as fino) ferrocene) palladium.
  • a palladium complex having a tertiary phosphine as a ligand is more preferable in terms of a good reaction yield, is easily available, and a palladium complex having triphenylphosphine as a ligand is preferable in terms of a good reaction yield. Particularly preferred.
  • the palladium complex having tertiary phosphine as a ligand can also be prepared in a reaction system by adding tertiary phosphine to a palladium salt or complex compound.
  • the tertiary phosphine that can be used at this time is triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5.
  • 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferable because it is easily available and the reaction yield is good.
  • the molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 from the viewpoint of good reaction yield.
  • Bases that can be used in “Step 1” include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, fluorine. Examples thereof include cesium chloride, and potassium carbonate is preferable in terms of a good yield.
  • the molar ratio of base to compound (3) is preferably from 1: 2 to 10: 1, and more preferably from 1: 1 to 3: 1 in terms of good yield.
  • the molar ratio of the compound (2) and the compound (3) used in “Step 1” is preferably 1: 2 to 5: 1, and more preferably 1: 2 to 2: 1 in terms of a good yield.
  • Examples of the solvent that can be used in “Step 1” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene. You may use it combining suitably. It is desirable to use a mixed solvent of dioxane or tetrahydrofuran and water in terms of a good yield.
  • Step 1 can be carried out at a temperature appropriately selected from 0 ° C. to 150 ° C., and more preferably at 50 ° C. to 100 ° C. in terms of a good yield.
  • Step 2 is a method in which compound (4) is reacted with compound (5) in the presence or absence of a base in the presence of a palladium catalyst to obtain triazine compound (1) of the present invention.
  • reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc.
  • the target product can be obtained in high yield.
  • Step 2 can be applied by replacing Compound (2) with Compound (5) and Compound (3) with Compound (4).
  • the reaction conditions are not necessarily the same as those in “Step 1”.
  • the triazine compound (1) of the present invention is suitably used as a material for an organic electroluminescence device.
  • the triazine compound (1) of the present invention is suitably used as an electron transport material or an electron injection material for an organic electroluminescence device.
  • the triazine compound (1) of the present invention is effective when used as a part of the components of the organic electroluminescence device.
  • effects such as longer life, higher efficiency, and lower voltage can be obtained than conventional devices.
  • the triazine compound (1) of this invention when used as an organic electroluminescent element material, it is also possible to use it as a co-deposition film
  • the film-forming by a vacuum evaporation method is possible. Film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus.
  • the vacuum degree of the vacuum chamber when forming a film by the vacuum evaporation method is determined by taking into account the manufacturing tact time and manufacturing cost of manufacturing the organic electroluminescence device, and commonly used diffusion pumps, turbo molecular pumps, cryopumps, etc.
  • the deposition rate is preferably 0.005 to 1.0 nm / second, more preferably 0.01 to 1 nm / second, depending on the thickness of the film to be formed.
  • the triazine compound (1) of the present invention has high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran, or the like, a spin coating method using a general-purpose apparatus, Film formation by an inkjet method, a cast method, a dip method, or the like is also possible.
  • the typical structure of the organic electroluminescent element capable of obtaining the effects of the present invention includes a substrate, an anode, a hole injection layer, a hole transport layer light emitting layer, an electron transport layer, and a cathode.
  • the anode and cathode of the organic electroluminescent element are connected to a power source through an electrical conductor.
  • the organic electroluminescent device operates by applying a potential between the anode and the cathode. Holes are injected into the organic electroluminescent device from the anode, and electrons are injected into the organic electroluminescent device at the cathode.
  • the organic electroluminescent element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate.
  • the electrode in contact with the substrate is called the lower electrode for convenience.
  • the lower electrode is an anode, but the organic electroluminescence device of the present invention is not limited to such a form.
  • the substrate may be light transmissive or opaque, depending on the intended emission direction. Light transmission properties are desirable for viewing electroluminescent emission through a substrate. Transparent glass or plastic is generally employed as such a substrate.
  • the substrate may be a composite structure including multiple material layers.
  • anode should pass or substantially pass the emission.
  • Common transparent anode (anode) materials used in the present invention are indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide, but other metal oxides such as Aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide are also useful.
  • metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode.
  • the anode can be modified with plasma deposited fluorocarbon.
  • the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used.
  • conductors for this application include gold, iridium, molybdenum, palladium and platinum.
  • a hole injection layer can be provided between the anode and the hole transport layer.
  • the hole injection material can serve to improve the film forming properties of the subsequent organic layer and to facilitate injection of holes into the hole transport layer.
  • materials suitable for use in the hole injection layer include porphyrin compounds, plasma deposited fluorocarbon polymers, and amines having aromatic rings such as biphenyl groups and carbazole groups, such as m-MTDATA (4,4 ′ , 4 ′′ -tris [(3-methylphenyl) phenylamino] triphenylamine), 2T-NATA (4,4 ′, 4 ′′ -tris [(N-naphthalen-2-yl) -N-phenylamino ] Triphenylamine), triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N,
  • the hole transport layer of the organic electroluminescence device preferably contains one or more hole transport compounds such as aromatic tertiary amines.
  • Aromatic tertiary amine means that the compound contains one or more trivalent nitrogen atoms, the trivalent nitrogen atoms being bonded only to carbon atoms, one or more of these carbon atoms being An aromatic ring is formed.
  • the aromatic tertiary amine can be an arylamine, such as a monoarylamine, diarylamine, triarylamine, or a polymeric arylamine.
  • hole transport material an aromatic tertiary amine having one or more amine groups can be used.
  • a polymeric hole transport material can be used.
  • PVK poly (N-vinylcarbazole)
  • PVK polythiophene
  • polypyrrole polyaniline
  • NPD N, N′-bis (naphthalen-1-yl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine
  • ⁇ -NPD N, N′-di
  • TPBi 1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) ) Benzene
  • TPD N, N′-bis (3-methylphenyl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine
  • a layer containing (HAT-CN) may be provided.
  • the light emitting layer of the organic electroluminescent element contains a phosphorescent material or a fluorescent material. In this case, light emission occurs as a result of recombination of electron-hole pairs in this region.
  • the emissive layer may consist of a single material including both small molecules and polymers, but more commonly consists of a host material doped with a guest compound, in which case the emission is mainly from the dopant. Occurs and can have any color.
  • Examples of the host material for the light emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthryl group.
  • DPVBi 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl
  • BCzVBi 4,4′-bis (9-ethyl-3-carbazovinylene) 1,1′-biphenyl
  • TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene
  • ADN (9,10-di (2-naphthyl) anthracene
  • CBP 4,4′-bis (carbazole-9) -Yl) biphenyl
  • CDBP 4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl
  • the host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as defined above, or another material that supports hole-electron recombination, or a combination of these materials.
  • fluorescent dopants examples include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine and quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium or thiapyrylium compounds, fluorene derivatives, perifanthene derivatives, indeno Examples include perylene derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
  • An example of a useful phosphorescent dopant is an organometallic complex of a transition metal of iridium, platinum, palladium, or osmium.
  • dopants examples include Alq 3 (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) 3 ( And tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.
  • the thin film forming material used for forming the electron transport layer of the organic electroluminescence device of the present invention is the triazine compound (1) of the present invention.
  • the electron transporting layer may contain another electron transporting material, and examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Desirable alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include, for example, 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate).
  • a hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance.
  • Preferred compounds for the hole blocking layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).
  • an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, light emission efficiency, low voltage driving, or high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, or anthrone. Etc.
  • the cathode used in the present invention can be formed from almost any conductive material.
  • Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • the light emission characteristics of the organic electroluminescence device were evaluated by applying a direct current to the fabricated device at room temperature and using a luminance meter of LUMINANCE METER (BM-9) (TOPCON).
  • 4,6-Diphenyl-2- (3 ′- ⁇ 4- [3- (3) is the same as Example-9 except that 1.00 g of 3-pyridineboronic acid is changed to 1.00 g of 4-pyridineboronic acid.
  • Element Example 1 As the substrate, a glass substrate with an ITO transparent electrode on which a 2 mm wide indium-tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. The substrate was cleaned with isopropyl alcohol and then surface treated by ozone ultraviolet cleaning. Each layer was vacuum-deposited on the cleaned substrate by a vacuum deposition method, and an organic electroluminescence device having a light-emitting area of 4 mm 2 as shown in FIG. Each organic material was formed by a resistance heating method.
  • ITO indium-tin oxide
  • the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa.
  • a hole injection layer 2 a charge generation layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, and a cathode layer are formed as an organic compound layer on the glass substrate with an ITO transparent electrode shown by 1 in FIG. 7 were laminated in this order, and all were formed by vacuum deposition.
  • the hole injection layer 2 65 nm of HIL purified by sublimation was formed at a rate of 0.15 nm / second.
  • sublimated and purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second.
  • HTL was formed to a thickness of 10 nm at a rate of 0.15 nm / second.
  • EML-1 and EML-2 were deposited to a thickness of 25 nm at a ratio of 95: 5 (deposition rate of 0.18 nm / second).
  • the cathode layer 7 is formed of silver / magnesium (weight ratio 1/10) and silver in this order at 80 nm (film formation rate 0.5 nm / second) and 20 nm (film formation rate 0.2 nm / second), respectively. And it was set as the 2 layer structure.
  • Each film thickness was measured with a stylus type film thickness meter (DEKTAK).
  • this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less.
  • a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin manufactured by Nagase ChemteX Corporation were used.
  • a direct current was applied to the organic electroluminescent device produced as described above, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON.
  • V voltage
  • cd / A current efficiency
  • element lifetime (h) during continuous lighting was measured.
  • Table 2 of element lifetime (h) measures the luminance decay time at the time of continuous lighting when driving was prepared device at an initial luminance 800 cd / m 2, to the luminance (cd / m 2) is reduced by 10% The time required for was measured.
  • the element lifetime was shown as a relative value with the element lifetime (h) in element reference example 1 described later as the reference value (100). The results are shown in Table 2.
  • Element Example 2 In Device Example 1, 4,6-diphenyl-2- [2 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example 2 instead of Compound A-1 ] An organic electroluminescence device was prepared and evaluated in the same manner as in Device Example 1 except that 1,3,5-triazine (Compound A-421) was used. The results are shown in Table 2. In addition, about element lifetime, after measuring element lifetime (h), it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Reference Example 1 In Device Example 1, instead of compound A-2, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP2011-063584A An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that, 6-diphenyl-1,3,5-triazine (ETL-1) was used. The results are shown in Table 2. In addition, about element lifetime, after measuring element lifetime (h), the element lifetime of this element reference example 1 was made into the reference value (100).
  • Element Example 3 As the substrate, a glass substrate with an ITO transparent electrode on which a 2 mm wide indium-tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. The substrate was cleaned with isopropyl alcohol and then surface treated by ozone ultraviolet cleaning. Each layer was vacuum-deposited on the cleaned substrate by a vacuum evaporation method to produce an organic electroluminescence device having a light emission area of 4 mm 2 . Each organic material was formed by a resistance heating method.
  • ITO indium-tin oxide
  • the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa.
  • a sublimated HIL film having a thickness of 55 nm was formed at a rate of 0.15 nm / second.
  • sublimation-purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second.
  • HTL was formed to a thickness of 10 nm at a rate of 0.15 nm / second.
  • HTL-2 was deposited to a thickness of 10 nm at a speed of 0.15 nm / second.
  • EML-3 and EML-4 were deposited to a thickness of 25 nm at a ratio of 95: 5 (deposition rate of 0.18 nm / second).
  • ETL-2 As the first electron transport layer, ETL-2 was deposited to a thickness of 5 nm at a rate of 0.15 nm / second.
  • a metal mask was arranged so as to be orthogonal to the ITO stripe, and a cathode layer 19 was formed.
  • the cathode layer was formed by depositing silver / magnesium (weight ratio 1/10) and silver in this order at 80 nm (film formation rate 0.5 nm / second) and 20 nm (film formation rate 0.2 nm / second), respectively. A two-layer structure was adopted.
  • Each film thickness was measured with a stylus type film thickness meter (DEKTAK).
  • this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less.
  • a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin manufactured by Nagase ChemteX Corporation were used.
  • Element Example 4 In Device Example 3, 4,6-diphenyl-2- [2 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example 2 instead of Compound A-41 ] An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 3 except that 1,3,5-triazine (Compound A-421) was used. The results are shown in Table 3. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which set the element lifetime of the element reference example 2 to 100.
  • Element Reference Example 2 In Device Example 3, instead of compound A-41, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP2011-063584A An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 3 except that, 6-diphenyl-1,3,5-triazine (ETL-1) was used. The results are shown in Table 3. In addition, about element lifetime, after measuring element lifetime (h), the element lifetime of this element reference example 2 was made into the reference value (100).
  • the triazine compound (1) of the present invention is excellent in heat resistance of the film quality, and by using the compound, an organic electroluminescent device having excellent long life and luminous efficiency can be provided.
  • the triazine compound (1) of the present invention is used as an electron transport material for an organic electroluminescence device which is excellent in a low driving voltage. Furthermore, according to the present invention, it is possible to provide an organic electroluminescence device having excellent power consumption.
  • the triazine compound of the present invention since the triazine compound of the present invention has good thermal stability during sublimation purification, it can provide a material that is excellent in sublimation purification operability and has few impurities causing deterioration of the organic electroluminescence device. Further, since the triazine compound of the present invention is excellent in the stability of the deposited film, it is possible to provide a long-life organic electroluminescence device.
  • the thin film comprising the triazine compound (1) of the present invention is useful as a material for an organic electroluminescence device because it has excellent electron transport ability, hole blocking ability, oxidation-reduction resistance, water resistance, oxygen resistance, electron injection characteristics, and the like. It is useful as an electron transport material, a hole blocking material, a light emitting host material, and the like. It is particularly useful when used as an electron transport material. Further, since the triazine compound (1) of the present invention is a wide band gap compound, it can be suitably used not only for conventional fluorescent device applications but also for phosphorescent devices.

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Abstract

The present invention provides a triazine compound represented by general formula (1), which has excellent heat resistance and is useful as an electron transport material for organic electroluminescent elements having a long service life, excellent low-voltage drivability or excellent luminous efficiency. (In general formula (1), Ar1 represents a phenyl group or the like, and the two Ar1 moieties are the same; each of Ar2, Ar3, Ar5 and Ar6 independently represents a single bond or the like; each of Ar4 and Ar7 independently represents (a) a monocyclic or fused aromatic hydrocarbon group having 6-24 carbon atoms, or the like; the total number of ring member carbon atoms of the Ar2 to Ar4 moieties and the total number of ring member carbon atoms of the Ar5 to Ar7 moieties are both 5-25; A represents a single bond; each of B1 and B2 represents a single bond or a hydrogen atom, provided that one of the B1 and B2 moieties represents a single bond and forms a single bond with A, and the other represents a hydrogen atom; and each of Z1 and Z2 independently represents a nitrogen atom or C-H, provided that one of the Z1 and Z2 moieties represents a nitrogen atom and the other represents C-H.)

Description

トリアジン化合物、その製造方法、及びそれを構成成分とする有機電界発光素子Triazine compound, process for producing the same, and organic electroluminescent device comprising the same
　本発明は、トリアジン化合物とその製造方法、及びそれを含有する有機電界発光素子に関する。さらに詳しくは、トリアジン骨格にジアリールピリジル基をメタ結合又はオルト結合を介して組み合わせた構造を特徴とする、有機電界発光素子用材料として有用なトリアジン化合物とその製造方法に関し、当該トリアジン化合物を有機化合物層の少なくとも一層に用いることを特徴とする高効率、低電圧及び高耐久性の有機電界発光素子に関する。 The present invention relates to a triazine compound, a method for producing the same, and an organic electroluminescent device containing the triazine compound. More specifically, the present invention relates to a triazine compound useful as a material for an organic electroluminescence device, characterized by a structure in which a diarylpyridyl group is combined with a triazine skeleton via a meta bond or an ortho bond, and a method for producing the same. The present invention relates to an organic electroluminescence device having high efficiency, low voltage, and high durability, characterized by being used in at least one layer.
　有機電界発光素子は、発光材料を含有する発光層を、正孔輸送層と電子輸送層で挟み、さらにその外側に陽極と陰極を取付けたものを基本構成とし、発光層に注入された正孔及び電子の再結合により生ずる励起子が失活する際の光の放出（蛍光又は燐光）を利用する発光素子であり、既に小型のディスプレイだけでなく大型テレビや照明等の用途へ用いられている。なお、前記正孔輸送層は正孔輸送層と正孔注入層に、前記発光層は、電子ブロック層と発光層と正孔ブロック層に、前記電子輸送層は電子輸送層と電子注入層に分割して構成される場合もある。また、有機電界発光素子のキャリア輸送層（電子輸送層又は正孔輸送層）として、金属、有機金属化合物又はその他有機化合物をドープした共蒸着膜を用いる場合もある。 An organic electroluminescent device has a basic structure in which a light-emitting layer containing a light-emitting material is sandwiched between a hole transport layer and an electron transport layer, and an anode and a cathode are attached to the outside, and holes injected into the light-emitting layer And a light-emitting element that utilizes light emission (fluorescence or phosphorescence) when excitons generated by electron recombination are deactivated, and are already used for applications such as large televisions and lighting as well as small displays. . The hole transport layer is a hole transport layer and a hole injection layer, the light emitting layer is an electron block layer, a light emitting layer and a hole block layer, and the electron transport layer is an electron transport layer and an electron injection layer. In some cases, it may be divided. In some cases, a co-deposited film doped with a metal, an organometallic compound, or another organic compound may be used as the carrier transport layer (electron transport layer or hole transport layer) of the organic electroluminescence device.
　従来の有機電界発光素子は、無機発光ダイオードに比べて駆動電圧が高く、発光輝度や発光効率も低く、素子寿命も著しく低く、実用化には至っていなかった。最近の有機電界発光素子は徐々に改良されているものの、発光効率特性、駆動電圧特性、長寿命特性において、さらに優れた材料が求められている。更に、車載用途等、用途によっては高い耐熱性を要する場合もあり、材料は高いガラス転移温度（Ｔｇ）を求められている。 Conventional organic electroluminescent elements have a higher driving voltage than inorganic light emitting diodes, have low luminance and luminous efficiency, have extremely low element lifetime, and have not been put into practical use. Although recent organic electroluminescence devices have been gradually improved, further excellent materials are demanded in terms of luminous efficiency characteristics, driving voltage characteristics, and long life characteristics. Furthermore, high heat resistance may be required depending on applications such as in-vehicle applications, and the material is required to have a high glass transition temperature (Tg).
　有機電界発光素子用の長寿命性に優れる電子輸送材料として、特許文献１で開示されたトリアジン化合物が挙げられる。しかしながら、当該材料を用いた有機電界発光素子の電圧、寿命及び発光効率の点で更なる改良が求められていた。 Examples of the electron transport material having excellent long life for organic electroluminescence devices include the triazine compound disclosed in Patent Document 1. However, further improvements have been demanded in terms of voltage, lifetime and luminous efficiency of organic electroluminescent devices using such materials.
　特許文献２には、ジアリールピリジル基を有するトリアジン化合物等が開示されている。当該化合物は、有機電界発光素子の高発光効率化の点で優れるものであるが、更なる発光効率の改善が求められていた。 Patent Document 2 discloses a triazine compound having a diarylpyridyl group. The compound is excellent in terms of increasing the luminous efficiency of the organic electroluminescent device, but further improvement in luminous efficiency has been demanded.
日本国特開２０１１－０６３５８４号公報Japanese Unexamined Patent Publication No. 2011-063584 国際公開第２０１６／００２８６４号パンフレットInternational Publication No. 2016/002864 Pamphlet
　本発明の目的は、膜質の耐熱性に優れ、有機電界発光素子の低電圧駆動性、発光効率又は長寿命性に優れる電子輸送材料を提供することである。 An object of the present invention is to provide an electron transport material which is excellent in heat resistance of film quality and excellent in low voltage drive performance, light emission efficiency or long life of an organic electroluminescence device.
　本発明者らは、先の課題を解決すべく鋭意検討を重ねた結果、ジアリールピリジル基とトリアジン部位がメタ結合又はオルト結合を介して結合したトリアジン化合物（以下、「トリアジン化合物（１）」ともいう）の膜質の耐熱性が高く、当該化合物を電子輸送材料として用いた有機電界発光素子が、従来公知の材料を用いた場合に比べて低電圧化、高発光効率化、又は長寿命化することを見いだし、本願発明を完成させるに至った。 As a result of intensive studies to solve the above problems, the present inventors have found that a triazine compound (hereinafter referred to as “triazine compound (1)”) in which a diarylpyridyl group and a triazine moiety are bonded via a meta bond or an ortho bond. The organic electroluminescence device using the compound as an electron transporting material has a lower voltage, higher luminous efficiency, or longer life than when a conventionally known material is used. As a result, the present invention has been completed.
　すなわち本発明は、一般式（１） That is, the present invention has the general formula (1)
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
（一般式（１）中、
Ａｒ１は、フェニル基、又はナフチル基（これらの基は、フッ素原子、メチル基、又はフェニル基で置換されていてもよい）を表し、二つのＡｒ１は同一である。
Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表す。
Ａｒ４、及びＡｒ７は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）を表す。
Ａｒ２、Ａｒ３、及びＡｒ４の環構成炭素原子の総数、及びＡｒ５、Ａｒ６、及びＡｒ７の環構成炭素原子の総数は、いずれも５～２５である。
Ａは、単結合を表す。
Ｂ１及びＢ２は、単結合又は水素原子を表す。但し、Ｂ１又はＢ２の何れか一方が単結合を表してＡと単結合を形成し、もう一方は水素原子を表す。
Ｚ１及びＺ２は各々独立に、窒素原子又はＣ－Ｈを表す。但し、Ｚ１又はＺ２の何れか一方が窒素原子を表し、もう一方はＣ－Ｈを表す。）
で示されるトリアジン化合物、その製造方法、及びそれを用いた有機電界発光素子に関するものである。 (In general formula (1),
Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same.
Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring. 1 to 25 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
The total number of ring carbon atoms of Ar 2 , Ar 3 , and Ar 4 and the total number of ring carbon atoms of Ar 5 , Ar 6 , and Ar 7 are all 5 to 25.
A represents a single bond.
B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
Z 1 and Z 2 each independently represents a nitrogen atom or C—H. However, either Z 1 or Z 2 represents a nitrogen atom, and the other represents C—H. )
And a method for producing the triazine compound, and an organic electroluminescent device using the triazine compound.
　すなわち、本発明は以下の［１］乃至［１３］に存する。
［１］　上記の一般式（１）で示されるトリアジン化合物。
［２］　Ａｒ１が、フェニル基、トリル基、ナフチル基、又はビフェニル基を表し、二つのＡｒ１は同一である［１］に記載のトリアジン化合物。
［３］　Ａｒ１が、いずれも、フェニル基である［１］又は［２］に記載のトリアジン化合物。
［４］　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６が、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ’）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合であり、尚且つＡｒ４、及びＡｒ７が、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ’）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることを特徴とする［１］、［２］、又は［３］に記載のトリアジン化合物。
［５］　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６が、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、ジベンゾチエニル基（これらの基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表し、尚且つＡｒ４、及びＡｒ７は、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることを特徴とする［１］、［２］、［３］、［４］、又は［５］に記載のトリアジン化合物。
［６］　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６が、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、ジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表し、尚且つＡｒ４、及びＡｒ７は、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることを特徴とする［１］、［２］、［３］、［４］、又は［５］に記載のトリアジン化合物。
［７］　－Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基が、各々独立に、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、フルオランテニルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、キノリルフェニル基、チエニルフェニル基、フリルフェニル基、ベンゾチエニルフェニル基、ベンゾフリルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、ベンゾチエニル基、ベンゾフリル基、フェナントリル基、アントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、フッ素原子、又はメチル基で置換されていてもよい）であることを特徴とする［１］、［２］、［３］、［４］、［５］、又は［６］に記載のトリアジン化合物。
［８］　－Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基が、各々独立に、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、メチル基で置換されていてもよい）である［１］、［２］、［３］、［４］、［５］、［６］、又は［７］に記載のトリアジン化合物。
［９］　－Ａｒ２－Ａｒ３－Ａｒ４で表される基、又は－Ａｒ５－Ａｒ６－Ａｒ７で表される基の何れか一方が、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、フッ素原子、又はメチル基で置換されていてもよい）であり、もう一方が、フェニル基、ビフェニル基、ピリジル基、又はナフチル基（これらの基は、メチル基で置換されていてもよい）である［１］、［２］、［３］、［４］、［５］、［６］、［７］、又は［８］に記載のトリアジン化合物。
［１０］　－Ａｒ２－Ａｒ３－Ａｒ４で表される基、又は－Ａｒ５－Ａｒ６－Ａｒ７で表される基の何れか一方が、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、メチル基で置換されていてもよい）であり、もう一方がフェニル基、又はナフチル基である［１］、［２］、［３］、［４］、［５］、［６］、［７］、［８］、又は［９］に記載のトリアジン化合物。
［１１］　カップリング反応を利用することを特徴とする［１］に記載のトリアジン化合物の製造方法。
［１２］　［１］に記載のトリアジン化合物を含む有機電界発光素子用材料。
［１３］　［１］に記載のトリアジン化合物を含む有機電界発光素子用電子輸送材料。 That is, the present invention resides in the following [1] to [13].
[1] A triazine compound represented by the general formula (1).
[2] Ar 1 is a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group, a triazine compound according to the two Ar 1 are the same [1].
[3] The triazine compound according to [1] or [2], wherein Ar 1 is a phenyl group.
[4] Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b ′) only from a 6-membered ring. A monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms, (c) a monocyclic ring having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S Or a condensed ring heteroaromatic group (the groups represented by (a), (b ′), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, and a carbon number of 1 to 4 Or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 are each independently (a) 6 to 24 carbon atoms. A monocyclic or condensed aromatic hydrocarbon group, (b ′) a monocyclic ring having 3 to 11 carbon atoms consisting of only a 6-membered ring, or A ring nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of H, C, O, and S (the ( The groups represented by a), (b ′) and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. The triazine compound according to [1], [2], or [3], wherein
[5] Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoran. Tenenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (these groups are phenyl group, tolyl group) , A pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 , and Ar 7 are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group Benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, Or a dibenzothienyl group (these groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms) [1], The triazine compound according to [2], [3], [4], or [5].
[6] Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoran. Tenenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (these groups are fluorine atom, carbon number An alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 are each independently a phenyl group or a naphthyl group. Fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, Oranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are fluorine atom, carbon [1], [2], [3], [4], or [which may have an alkyl group of 1 to 4 or an alkoxy group of 1 to 4 carbon atoms] 5].
[7] The group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenyl group, Nantrylphenyl group, fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzo Furylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group Dibenzothienyl group Or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group) [1], [2], [3], [4], [5] Or the triazine compound according to [6].
[8] The group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenyl group, Nantrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl [1], [2], [3], which is a phenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a methyl group), The triazine compound according to [4], [5], [6], or [7].
[9] Either one of the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenyl group, Nantrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl A phenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and the other is a phenyl group, Biphenyl group, pyridyl group, or naphthyl group (these groups are methyl groups, Also it may) have been conversion [1], [2], [3], [4], [5], [6], [7], or triazine compounds described in [8].
[10] Either of the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is a phenyl group, a biphenyl group, a naphthylphenyl group, a phenoxy group, Nantrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofuryl A phenyl group, a bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a methyl group), and the other is a phenyl group or a naphthyl group [1], [2], [3], [4], [5], [6], [7], [8] Or triazine compounds described in [9].
[11] The method for producing a triazine compound according to [1], wherein a coupling reaction is used.
[12] A material for an organic electroluminescence device comprising the triazine compound according to [1].
[13] An electron transport material for an organic electroluminescence device comprising the triazine compound according to [1].
　本発明によれば、膜質の耐熱性に優れるトリアジン化合物を提供することができ、低電圧、発光効率、又は長寿命に優れる有機電界発光素子を提供することができる。 According to the present invention, it is possible to provide a triazine compound excellent in heat resistance of film quality, and it is possible to provide an organic electroluminescence device excellent in low voltage, light emission efficiency, or long life.
　以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
　本発明は、上記のトリアジン化合物（１）、その製造方法、及び当該材料を使用して有機電界発光素子用材料を提供することに関するものである。 The present invention relates to the triazine compound (1), a method for producing the same, and providing an organic electroluminescent element material using the material.
　本発明のトリアジン化合物（１）における置換基はそれぞれ以下のように定義される。 The substituents in the triazine compound (1) of the present invention are defined as follows.
　式（１）中、Ａｒ１は、フェニル基、又はナフチル基（これらの基は、フッ素原子、メチル基、又はフェニル基で置換されていてもよい）を表し、二つのＡｒ１は同一である。 In Formula (1), Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same. .
　Ａｒ１における、フッ素原子で置換されたフェニル基、又はナフチル基としては、特に限定するものではないが、フルオロフェニル基、ペンタフルオロフェニル基、ジフルオロフェニル基、フルオロナフチル基、又はジフルオロナフチル基等が好ましい例として挙げられる。 The phenyl group or naphthyl group substituted with a fluorine atom in Ar 1 is not particularly limited. A preferred example is given.
　Ａｒ１における、メチル基で置換されたフェニル基、又はナフチル基としては、特に限定するものではないが、トリル基、メチルナフチル基、ジメチルフェニル基、又はジメチルナフチル基等が好ましい例として挙げられる。 A phenyl group substituted with a methyl group or a naphthyl group in Ar 1 is not particularly limited, but a tolyl group, a methylnaphthyl group, a dimethylphenyl group, a dimethylnaphthyl group, and the like are preferable examples.
　Ａｒ１における、フェニル基で置換されたフェニル基、又はナフチル基としては、特に限定するものではないが、ビフェニル基、フェニルナフチル基、ターフェニル基、又はジフェニルナフチル基等が好ましい例として挙げられる。 A phenyl group substituted with a phenyl group or a naphthyl group in Ar 1 is not particularly limited, and preferred examples include a biphenyl group, a phenylnaphthyl group, a terphenyl group, or a diphenylnaphthyl group.
　Ａｒ１は、電子輸送性材料特性に優れる点で、フェニル基、トリル基、ナフチル基、又はビフェニル基であることがより好ましく、合成が容易な点でフェニル基であることがさらに好ましい。 Ar 1 is more preferably a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group from the viewpoint of excellent electron transporting material characteristics, and more preferably a phenyl group from the viewpoint of easy synthesis.
　Ａｒ１の具体例としては、特に限定するものではないが、フェニル基、ｐ－トリル基、ｍ－トリル基、ｏ－トリル基、２，４－ジメチルフェニル基、３，５－ジメチルフェニル基、メシチル基、２－フルオロフェニル基、３－フルオロフェニル基、４－フルオロフェニル基、２，４－ジフルオロフェニル基、３，５－ジフルオロフェニル基、ビフェニル－２－イル基、ビフェニル－３－イル基、ビフェニル－４－イル基、３－メチルビフェニル－４－イル基、２’－メチルビフェニル－４－イル基、４’－メチルビフェニル－４－イル基、２，２’－ジメチルビフェニル－４－イル基、２’，４’，６’－トリメチルビフェニル－４－イル基、６－メチルビフェニル－３－イル基、５－メチルビフェニル－３－イル基、２’－メチルビフェニル－３－イル基、４’－メチルビフェニル－３－イル基、６，２’－ジメチルビフェニル－３－イル基、２’，４’，６’－トリメチルビフェニル－３－イル基、５－メチルビフェニル－２－イル基、６－メチルビフェニル－２－イル基、２’－メチルビフェニル－２－イル基、４’－メチルビフェニル－２－イル基、６，２’－ジメチルビフェニル－２－イル基、２’，４’，６’－トリメチルビフェニル－２－イル基、１－ナフチル基、２－ナフチル基、１－フェニルナフタレン－２－イル基、１－フェニルナフタレン－３－イル基、１－フェニルナフタレン－４－イル基、１－フェニルナフタレン－５－イル基、１－フェニルナフタレン－６－イル基、１－フェニルナフタレン－７－イル基、１－フェニルナフタレン－８－イル基、２－フェニルナフタレン－１－イル基、２－フェニルナフタレン－３－イル基、２－フェニルナフタレン－４－イル基、２－フェニルナフタレン－５－イル基、２－フェニルナフタレン－６－イル基、２－フェニルナフタレン－７－イル基、２－フェニルナフタレン－８－イル基、１－メチルナフタレン－４－イル基、１－メチルナフタレン－５－イル基、１－メチルナフタレン－６－イル基、１－メチルナフタレン－７－イル基、１－メチルナフタレン－８－イル基、２－メチルナフタレン－１－イル基、２－メチルナフタレン－３－イル基、２－メチルナフタレン－４－イル基、２－メチルナフタレン－５－イル基、２－メチルナフタレン－６－イル基、２－メチルナフタレン－７－イル基、又は２－メチルナフタレン－８－イル基等が好ましい例として挙げられる。これらの置換基のうち、電子輸送性材料特性に優れる点で、フェニル基、ｐ－トリル基、ビフェニル－３－イル基、ビフェニル－４－イル基、１－ナフチル基、又は２－ナフチル基が好ましく、フェニル基、ビフェニル－３－イル基、ビフェニル－４－イル基、１－ナフチル基、又は２－ナフチル基がより好ましい。 Specific examples of Ar 1 include, but are not limited to, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, Mesityl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, biphenyl-2-yl group, biphenyl-3-yl group Biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4- Yl group, 2 ', 4', 6'-trimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3- 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group, 2 ', 4', 6'-trimethylbiphenyl-3-yl group, 5-methylbiphenyl-2 -Yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl-2-yl group, 4'-methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group, 2 ', 4', 6'-trimethylbiphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalene -4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalene-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalene -1 Yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2-phenylnaphthalene-7- Yl group, 2-phenylnaphthalen-8-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalene-7- Yl, 1-methylnaphthalen-8-yl, 2-methylnaphthalen-1-yl, 2-methylnaphthalen-3-yl, 2-methylnaphthalen-4-yl, 2-methylnaphthalene-5 Preferred examples include yl group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, and 2-methylnaphthalen-8-yl group. Among these substituents, a phenyl group, a p-tolyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is preferable because of excellent electron transporting material characteristics. A phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is more preferable.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表す。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring. 1 to 25 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、同一であっても相異なっていてもよい。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 may be the same or different.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６における、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基としては、特に限定するものではないが、フェニル基、ナフチル基、フェナントリル基、アントリル基、ピレニル基、トリフェニレニル基、クリセニル基、フルオランテニル基、アセナフチル基、フルオレニル基、又はベンゾフルオレニル基等が好ましい例として挙げられる。なお、上述の通り、これらの置換基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基で置換されていてもよい。 The (a) monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited, but includes a phenyl group, a naphthyl group, Preferable examples include phenanthryl group, anthryl group, pyrenyl group, triphenylenyl group, chrycenyl group, fluoranthenyl group, acenaphthyl group, fluorenyl group, or benzofluorenyl group. As described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６における、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基としては、特に限定するものではないが、ピリジル基、ピラジル基、ピリミジル基、ピリダジル基、トリアジル基、キノリル基、イソキノリル基、フェナントリジル基、ベンゾキノリル基、又はアクリジニル基等が好ましい例として挙げられる。なお、カルバゾリル基は、５員環を含むヘテロ芳香族基であり、本発明の６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基には含まれない。また、上述の通り、これらの置換基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基で置換されていてもよい。 The (b) monocyclic or condensed ring-containing nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only a 6-membered ring in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited. Pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazyl group, quinolyl group, isoquinolyl group, phenanthridyl group, benzoquinolyl group, acridinyl group and the like are preferable examples. The carbazolyl group is a heteroaromatic group containing a 5-membered ring, and is not included in the monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 25 carbon atoms consisting of only the 6-membered ring of the present invention. Further, as described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６における、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基としては、特に限定するものではないが、チエニル基、フリル基、ビチエニル基、ビフリル基、ベンゾチエニル基、ベンゾフリル基、ジベンゾチエニル基、又はジベンゾフリル基等が好ましい例として挙げられる。なお、上述の通り、これらの置換基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基で置換されていてもよい。 (C) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of H, C, O, and S in Ar 2 , Ar 3 , Ar 5 , and Ar 6 The group is not particularly limited, and preferred examples include a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, or a dibenzofuryl group. As described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６における、炭素数１～４のアルキル基としては、特に限定するものではないが、メチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、又はｔ－ブチル基等が好ましい例として挙げられる。 The alkyl group having 1 to 4 carbon atoms in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited, but a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, Alternatively, a t-butyl group and the like are preferable examples.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６における、炭素数１～４のアルコキシ基としては、特に限定するものではないが、メトキシ基、エトキシ基、ｎ－プロポキシ基、イソプロポキシ基、ｎ－ブトキシ基、又はｔ－ブトキシ基等が好ましい例として挙げられる。 The alkoxy group having 1 to 4 carbon atoms in Ar 2 , Ar 3 , Ar 5 , and Ar 6 is not particularly limited, but is not limited to methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n- Preferred examples include a butoxy group or a t-butoxy group.
　Ａｒ４、及びＡｒ７は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）を表す。 Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
　Ａｒ４、及びＡｒ７において、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基、炭素数１～４のアルキル基、及び炭素数１～４のアルコキシ基の構成要件については、何れも、Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６と同義である。 In Ar 4 and Ar 7 , (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a monocyclic or condensed ring-containing nitrogen having 3 to 25 carbon atoms consisting of only a 6-membered ring. A heteroaromatic group, (c) a monocyclic or condensed ring heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S, and having 1 to 4 carbon atoms The constituent requirements for the alkyl group and the alkoxy group having 1 to 4 carbon atoms are all synonymous with Ar 2 , Ar 3 , Ar 5 , and Ar 6 .
　以上より、－Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基としては、特に限定するものではないが、例えば、としては、特に限定するものではないが、例えば、フェニル基、ビフェニル基、ターフェニル基、ナフチルフェニル基、フェナントリルフェニル基、アントリルフェニル基、ピレニルフェニル基、トリフェニルフェニル基、クリセニルフェニル基、フルオランテニルフェニル基、アセナフチルフェニル基、フルオレニルフェニル基、ナフチルビフェニル基、ナフチル基、フェニルナフチル基、ビフェニルナフチル基、フェナントリルナフチル基、アントリルナフチル基、フェナントリル基、フェニルフェナントリル基、ナフチルフェナントリル基、アントリル基、フェニルアントリル基、ナフチルアントリル基、ピレニル基、フェニルピレニル基、トリフェニレニル基、フェニルトリフェニレニル基、クリセニル基、フェニルクリセニル基、フルオランテニル基、フェニルフルオランテニル基、アセナフチル基、フェニルアセナフチル基、フルオレニル基、フェニルフルオレニル基、ベンゾフルオレニル基、フルオロフェニル基、ペンタフルオロフェニル基、フルオロビフェニル基、フルオロターフェニル基、フルオロナフチルフェニル基、ナフチルフルオロフェニル基、フルオロフェナントリルフェニル基、フェナントリルフルオロフェニル基、フルオロアントリルフェニル基、アントリルフルオロフェニル基、フルオロピレニルフェニル基、ピレニルフルオロフェニル基、フルオロトリフェニルフェニル基、トリフェニルフルオロフェニル基、フルオロクリセニルフェニル基、クリセニルフルオロフェニル基、フルオロフルオランテニルフェニル基、フルオランテンフルオロフェニル基、フルオロアセナフチルフェニル基、アセナフチルフルオロフェニル基、フルオロフルオレニルフェニル基、フルオレニルフルオロフェニル基、フルオロナフチルビフェニル基、ナフチルフルオロビフェニル基、フルオロナフチル基、フルオロフェニルナフチル基、フェニルフルオロナフチル基、フルオロビフェニルナフチル基、ビフェニルフルオロナフチル基、フルオロフェナントリルナフチル基、フェナントリルフルオロナフチル基、フルオロアントリルナフチル基、アントリルフルオロナフチル基、フルオロフェナントリル基、フルオロフェニルフェナントリル基、フェニルフルオロフェナントリル基、フルオロナフチルフェナントリル基、ナフチルフルオロフェナントリル基、フルオロアントリル基、フルオロフェニルアントリル基、フェニルフルオロアントリル基、フルオロナフチルアントリル基、ナフチルフルオロアントリル基、フルオロピレニル基、フルオロフェニルピレニル基、フェニルフルオロピレニル基、フルオロトリフェニレニル基、フルオロフェニルトリフェニレニル基、フェニルフルオロトリフェニレニル基、フルオロクリセニル基、フルオロフェニルクリセニル基、フェニルフルオロクリセニル基、フルオロフルオランテニル基、フルオロフェニルフルオランテニル基、フェニルフルオロフルオランテニル基、フルオロアセナフチル基、フルオロフェニルアセナフチル基、フェニルフルオロアセナフチル基、フルオロフルオレニル基、フルオロフェニルフルオレニル基、フェニルフルオロフルオレニル基、フルオロベンゾフルオレニル基、ピリジル基、ピラジル基、ピリミジル基、ピリダジル基、トリアジル基、キノリル基、イソキノリル基、フェナントリジル基、ベンゾキノリル基、アクリジニル基、ピリジルフェニル基、ピラジルフェニル基、ピリミジルフェニル基、ピリダジルフェニル基、トリアジルフェニル基、キノリルフェニル基、イソキノリルフェニル基、フェナントリジルフェニル基、ベンゾキノリルフェニル基、アクリジニルフェニル基、（フェニルピリジル）フェニル基、（ナフチルピリジル）フェニル基、ピリジルビフェニル基、ピラジルビフェニル基、ピリミジルビフェニル基、ピリダジルビフェニル基、トリアジルビフェニル基、キノリルビフェニル基、イソキノリルビフェニル基、フェナントリジルビフェニル基、ベンゾキノリルビフェニル基、アクリジニルビフェニル基、ピリジルターフェニル基、ピラジルターフェニル基、ピリミジルターフェニル基、ピリダジルターフェニル基、トリアジルターフェニル基、ピリジルナフチル基、ピラジルナフチル基、ピリミジルナフチル基、ピリダジルナフチル基、トリアジルナフチル基、キノリルナフチル基、イソキノリルナフチル基、フェナントリジルナフチル基、ベンゾキノリルナフチル基、アクリジニルナフチル基、フェニルピリジル基、ビフェニルピリジル基、ナフチルピリジル基、フェナントリルピリジル基、アントリルピリジル基、ピレニルピリジル基、トリフェニレニルピリジル基、クリセニルピリジル基、フルオランテニルピリジル基、アセナフチルピリジル基、フルオレニルピリジル基、チエニル基、フリル基、ビチエニル基、ビフリル基、ベンゾチエニル基、ベンゾフリル基、ジベンゾチエニル基、ジベンゾフリル基、チエニルフェニル基、フリルフェニル基、ビチエニルフェニル基、ビフリルフェニル基、ベンゾチエニルフェニル基、ベンゾフリルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、チエニルビフェニル基、フリルビフェニル基、ベンゾチエニルビフェニル基、ベンゾフリルビフェニル基、ジベンゾチエニルビフェニル基、ジベンゾフリルビフェニル基、チエニルナフチル基、フリルナフチル基、ベンゾチエニルナフチル基、ベンゾフリルナフチル基、ジベンゾチエニルナフチル基、ジベンゾフリルナフチル基、フェニルチエニル基、フェニルフリル基、ビフェニルチエニル基、ビフェニルフリル基、ナフチルチエニル基、ナフチルフリル基、フェナントリルチエニル基、フェナントリルフリル基、アントリルチエニル基、アントリルフリル基、ピレニルチエニル基、ピレニルフリル基、トリフェニレニルチエニル基、トリフェニレニルフリル基、クリセニルチエニル基、クリセニルフリル基、フルオランテニルチエニル基、フルオランテニルフリル基、アセナフチルチエニル基、アセナフチルフリル基、フルオレニルチエニル基、又はフルオレニルフリル基等が好ましい例として挙げられる。 From the above, the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are not particularly limited, but for example, Without limitation, for example, phenyl group, biphenyl group, terphenyl group, naphthylphenyl group, phenanthrylphenyl group, anthrylphenyl group, pyrenylphenyl group, triphenylphenyl group, chrysenylphenyl group, Fluoranthenylphenyl group, acenaphthylphenyl group, fluorenylphenyl group, naphthylbiphenyl group, naphthyl group, phenylnaphthyl group, biphenylnaphthyl group, phenanthrylnaphthyl group, anthrylnaphthyl group, phenanthryl group, phenylphenanthryl Group, naphthylphenanthryl group, anthryl group, phenylanthryl group , Naphthylanthryl group, pyrenyl group, phenylpyrenyl group, triphenylenyl group, phenyltriphenylenyl group, chrycenyl group, phenylchrycenyl group, fluoranthenyl group, phenylfluoranthenyl group, acenaphthyl group, phenylacenaphthyl group , Fluorenyl group, phenylfluorenyl group, benzofluorenyl group, fluorophenyl group, pentafluorophenyl group, fluorobiphenyl group, fluoroterphenyl group, fluoronaphthylphenyl group, naphthylfluorophenyl group, fluorophenanthrylphenyl group , Phenanthrylfluorophenyl group, fluoroanthrylphenyl group, anthrylfluorophenyl group, fluoropyrenylphenyl group, pyrenylfluorophenyl group, fluorotriphenylphenyl group, triphenyl Fluorophenyl group, fluorochrenylphenyl group, chrycenylfluorophenyl group, fluorofluoranthenylphenyl group, fluoranthenefluorophenyl group, fluoroacenaphthylphenyl group, acenaphthylfluorophenyl group, fluorofluorenylphenyl group, Fluorenylfluorophenyl group, fluoronaphthylbiphenyl group, naphthylfluorobiphenyl group, fluoronaphthyl group, fluorophenylnaphthyl group, phenylfluoronaphthyl group, fluorobiphenylnaphthyl group, biphenylfluoronaphthyl group, fluorophenanthrylnaphthyl group, phenane Tolylfluoronaphthyl group, fluoroanthrylnaphthyl group, anthrylfluoronaphthyl group, fluorophenanthryl group, fluorophenylphenanthryl group, Rufluorophenanthryl group, fluoronaphthylphenanthryl group, naphthylfluorophenanthryl group, fluoroanthryl group, fluorophenylanthryl group, phenylfluoroanthryl group, fluoronaphthylanthryl group, naphthylfluoroanthryl group, Fluoropyrenyl group, fluorophenylpyrenyl group, phenylfluoropyrenyl group, fluorotriphenylenyl group, fluorophenyltriphenylenyl group, phenylfluorotriphenylenyl group, fluorochrysenyl group, fluorophenylchrysenyl group, phenylfluoro Chrycenyl group, fluorofluoranthenyl group, fluorophenylfluoranthenyl group, phenylfluorofluoranthenyl group, fluoroacenaphthyl group, fluorophenylacenaphthyl group, phenylfluorine Loacenaphthyl group, fluorofluorenyl group, fluorophenylfluorenyl group, phenylfluorofluorenyl group, fluorobenzofluorenyl group, pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazyl group, quinolyl group, isoquinolyl group Phenanthridyl group, benzoquinolyl group, acridinyl group, pyridylphenyl group, pyrazylphenyl group, pyrimidylphenyl group, pyridazylphenyl group, triazylphenyl group, quinolylphenyl group, isoquinolylphenyl group, Nantridylphenyl group, benzoquinolylphenyl group, acridinylphenyl group, (phenylpyridyl) phenyl group, (naphthylpyridyl) phenyl group, pyridylbiphenyl group, pyrazylbiphenyl group, pyrimidylbiphenyl group, pyridazylbiphenyl Base Triazylbiphenyl group, quinolylbiphenyl group, isoquinolylbiphenyl group, phenanthridylbiphenyl group, benzoquinolylbiphenyl group, acridinylbiphenyl group, pyridylterphenyl group, pyrazylterphenyl group, pyrimidylterphenyl group , Pyridazyl terphenyl group, triazyl terphenyl group, pyridyl naphthyl group, pyrazyl naphthyl group, pyrimidyl naphthyl group, pyridazyl naphthyl group, triazyl naphthyl group, quinolyl naphthyl group, isoquinolyl naphthyl group, fe Nantridylnaphthyl, benzoquinolylnaphthyl, acridinylnaphthyl, phenylpyridyl, biphenylpyridyl, naphthylpyridyl, phenanthrylpyridyl, anthrylpyridyl, pyrenylpyridyl, triphenylenylpyridyl , Chrysenylpyridyl group, fluoranthenylpyridyl group, acenaphthylpyridyl group, fluorenylpyridyl group, thienyl group, furyl group, bithienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzofuryl group , Thienylphenyl group, furylphenyl group, bithienylphenyl group, bifurylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, thienylbiphenyl group, furylbiphenyl group, benzothienylbiphenyl Group, benzofurylbiphenyl group, dibenzothienylbiphenyl group, dibenzofurylbiphenyl group, thienylnaphthyl group, furylnaphthyl group, benzothienylnaphthyl group, benzofurylnaphthyl group, dibenzothienylnaphth Til, dibenzofurylnaphthyl, phenylthienyl, phenylfuryl, biphenylthienyl, biphenylfuryl, naphthylthienyl, naphthylfuryl, phenanthrylthienyl, phenanthrylthyl, anthrylthienyl Tolylfuryl, pyrenylthienyl, pyrenylfuryl, triphenylenylthienyl, triphenylenylfuryl, chrysenylthienyl, chrysenylfuryl, fluoranthenylthienyl, fluoranthenylfuryl, acenaphthylthienyl, acenaphthyl Preferred examples include a furyl group, a fluorenylthienyl group, a fluorenylfuryl group, and the like.
　なお、Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６については、電子輸送性材料特性に優れる点で、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ’）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合であることが好ましく、尚且つＡｒ４、及びＡｒ７については、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ’）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることが好ましい。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms in terms of excellent electron transporting material characteristics. (B ′) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only a 6-membered ring, and (c) an atom selected from an atomic group consisting of H, C, O, and S A C3-C25 monocyclic or condensed heteroaromatic group (the groups represented by (a), (b ′), and (c) are phenyl, tolyl, pyridyl, methylpyridyl, A fluorine atom, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 Are each independently (a) a monocyclic or condensed aromatic carbon having 6 to 24 carbon atoms. A basic group, (b ′) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only a 6-membered ring, or (c) an atomic group consisting of H, C, O, and S A monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of atoms (the groups represented by (a), (b ′) and (c) are fluorine atoms, 1 to 4 carbon atoms) Or an alkyl group having 1 to 4 carbon atoms).
　当該好ましい範囲の記載における、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基、炭素数１～４のアルキル基、及び炭素数１～４のアルコキシ基については、上述したものと同義である。 In the description of the preferred range, it is composed of (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, (c) an atom selected from an atomic group consisting of H, C, O, and S. The monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms, the alkyl group having 1 to 4 carbon atoms, and the alkoxy group having 1 to 4 carbon atoms have the same meaning as described above.
　当該好ましい範囲の記載における（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、については、特に限定するものではないが、ピリジル基、ピラジル基、ピリミジル基、ピリダジル基、トリアジル基、キノリル基、又はイソキノリル基等が好ましい例として挙げられる。なお、カルバゾリル基は、炭素数１２のヘテロ芳香族基であり、本発明の６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基には含まれない。また、上述の通り、これらの置換基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基で置換されていてもよい。 In the description of the preferred range, (b ′) a monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only a 6-membered ring is not particularly limited, but includes a pyridyl group and a pyrazyl group. , A pyrimidyl group, a pyridazyl group, a triazyl group, a quinolyl group, an isoquinolyl group, and the like are preferable examples. The carbazolyl group is a heteroaromatic group having 12 carbon atoms, and is not included in the monocyclic or condensed nitrogen-containing heteroaromatic group having 3 to 11 carbon atoms consisting of only the 6-membered ring of the present invention. Further, as described above, these substituents are substituted with a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be.
　Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６については、電子輸送性材料特性に優れる点で、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合であることがより好ましく、尚且つＡｒ４、及びＡｒ７については、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることが好ましい。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, because they are excellent in electron transporting material properties. Pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, triazyl, pyrimidyl, piperazyl, pyridyl, quinolyl, isoquinolyl benzofuranyl, benzothienyl, dibenzofuranyl, or dibenzothienyl The group may have a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond More preferably, and Ar 4 and Ar 7 are each independently a phenyl group , Naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group , Benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (These groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. Preferably).
　また、Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６については、合成が容易な点で、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合であることがより好ましく、尚且つＡｒ４、及びＡｒ７については、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることが好ましい。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a benzofluorenyl group, a pyrenyl group because they are easily synthesized. Group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups More preferably a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7. Each independently, phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group , Benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group Or a dibenzothienyl group (these groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
　また、－Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基については、電子輸送性材料特性に優れる点で、各々独立に、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、フルオランテニルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、キノリルフェニル基、チエニルフェニル基、フリルフェニル基、ベンゾチエニルフェニル基、ベンゾフリルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、ベンゾチエニル基、ベンゾフリル基、フェナントリル基、アントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、フッ素原子、又はメチル基で置換されていてもよい）であることがより好ましく、各々独立に、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、メチル基で置換されていてもよい）であることがさらに好ましい。 In addition, the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently phenyl in terms of excellent electron transporting material characteristics. Group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzo Furylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl Group, benzofuryl group, phenanthri It is more preferable that the group is an aryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and each independently a phenyl group, a biphenyl group , Naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group , Pyrimidyl dibenzofurylphenyl group, bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group, or dibenzofuryl group (these groups may be substituted with a methyl group).
　また、－Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基については、合成が容易であり、膜質の耐熱性が高い点で、－Ａｒ２－Ａｒ３－Ａｒ４で表される基、又は－Ａｒ５－Ａｒ６－Ａｒ７で表される基の何れか一方が、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、フッ素原子、又はメチル基で置換されていてもよい）であり、もう一方が、フェニル基、ビフェニル基、ピリジル基、又はナフチル基（これらの基は、メチル基で置換されていてもよい）であることがより好ましく、－Ａｒ２－Ａｒ３－Ａｒ４で表される基、又は－Ａｒ５－Ａｒ６－Ａｒ７で表される基の何れか一方が、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、メチル基で置換されていてもよい）であり、もう一方がフェニル基、又はナフチル基であることがさらに好ましい。 In addition, the group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are easy to synthesize and have high heat resistance of film quality. Either the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl. Group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, Bipyridyl group, naphthyl group, phenanthryl group, dibenzothienyl group, or dibenzofuryl group (these groups are Or the other is a phenyl group, a biphenyl group, a pyridyl group, or a naphthyl group (these groups may be substituted with a methyl group). Is more preferable, and any one of the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is a phenyl group, a biphenyl group, a naphthylphenyl group, Phenanthrylphenyl group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzo Furylphenyl, bipyridyl, naphthyl, phenanthryl, dibenzothienyl, or Benzofuryl group (these groups may be substituted with a methyl group), more preferably the other is a phenyl group, or naphthyl group.
　－Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基の具体例としては、特に限定するものではないが、例えば、フェニル基、ｐ－トリル基、ｍ－トリル基、ｏ－トリル基、２，４－ジメチルフェニル基、３，５－ジメチルフェニル基、メシチル基、２－エチルフェニル基、３－エチルフェニル基、４－エチルフェニル基、２，４－ジエチルフェニル基、３，５－ジエチルフェニル基、２－プロピルフェニル基、３－プロピルフェニル基、４－プロピルフェニル基、２，４－ジプロピルフェニル基、３，５－ジプロピルフェニル基、２－イソプロピルフェニル基、３－イソプロピルフェニル基、４－イソプロピルフェニル基、２，４－ジイソプロピルフェニル基、３，５－ジイソプロピルフェニル基、２－ブチルフェニル基、３－ブチルフェニル基、４－ブチルフェニル基、２，４－ジブチルフェニル基、３，５－ジブチルフェニル基、２－ｔｅｒｔ－ブチルフェニル基、３－ｔｅｒｔ－ブチルフェニル基、４－ｔｅｒｔ－ブチルフェニル基、２，４－ジ－ｔｅｒｔ－ブチルフェニル基、３，５－ジ－ｔｅｒｔ－ブチルフェニル基、ビフェニル－２－イル基、ビフェニル－３－イル基、ビフェニル－４－イル基、３－メチルビフェニル－４－イル基、２’－メチルビフェニル－４－イル基、４’－メチルビフェニル－４－イル基、２，２’－ジメチルビフェニル－４－イル基、２’，４’，６’－トリメチルビフェニル－４－イル基、６－メチルビフェニル－３－イル基、５－メチルビフェニル－３－イル基、２’－メチルビフェニル－３－イル基、４’－メチルビフェニル－３－イル基、６，２’－ジメチルビフェニル－３－イル基、２’，４’，６’－トリメチルビフェニル－３－イル基、５－メチルビフェニル－２－イル基、６－メチルビフェニル－２－イル基、２’－メチルビフェニル－２－イル基、４’－メチルビフェニル－２－イル基、６，２’－ジメチルビフェニル－２－イル基、２’，４’，６’－トリメチルビフェニル－２－イル基、３－エチルビフェニル－４－イル基、４’－エチルビフェニル－４－イル基、２’，４’，６’－トリエチルビフェニル－４－イル基、６－エチルビフェニル－３－イル基、４’－エチルビフェニル－３－イル基、５－エチルビフェニル－２－イル基、４’－エチルビフェニル－２－イル基、２’，４’，６’－トリエチルビフェニル－２－イル基、３－プロピルビフェニル－４－イル基、４’－プロピルビフェニル－４－イル基、２’，４’，６’－トリプロピルビフェニル－４－イル基、６－プロピルビフェニル－３－イル基、４’－プロピルビフェニル－３－イル基、５－プロピルビフェニル－２－イル基、４’－プロピルビフェニル－２－イル基、２’，４’，６’－トリプロピルビフェニル－２－イル基、３－イソプロピルビフェニル－４－イル基、４’－イソプロピルビフェニル－４－イル基、２’，４’，６’－トリイソプロピルビフェニル－４－イル基、６－イソプロピルビフェニル－３－イル基、４’－イソプロピルビフェニル－３－イル基、５－イソプロピルビフェニル－２－イル基、４’－イソプロピルビフェニル－２－イル基、２’，４’，６’－トリイソプロピルビフェニル－２－イル基、３－ブチルビフェニル－４－イル基、４’－ブチルビフェニル－４－イル基、２’，４’，６’－トリブチルビフェニル－４－イル基、６－ブチルビフェニル－３－イル基、４’－ブチルビフェニル－３－イル基、５－ブチルビフェニル－２－イル基、４’－ブチルビフェニル－２－イル基、２’，４’，６’－トリブチルビフェニル－２－イル基、３－ｔｅｒｔ－ブチルビフェニル－４－イル基、４’－ｔｅｒｔ－ブチルビフェニル－４－イル基、２’，４’，６’－トリｔｅｒｔ－ブチルビフェニル－４－イル基、６－ｔｅｒｔ－ブチルビフェニル－３－イル基、４’－ｔｅｒｔ－ブチルビフェニル－３－イル基、５－ｔｅｒｔ－ブチルビフェニル－２－イル基、４’－ｔｅｒｔ－ブチルビフェニル－２－イル基、２’，４’，６’－トリｔｅｒｔ－ブチルビフェニル－２－イル基、２－ピリジル基、３－ピリジル基、４－ピリジル基、２－メチルピリジン－３－イル基、２－メチルピリジン－４－イル基、２－メチルピリジン－５－イル基、２－メチルピリジン－６－イル基、３－メチルピリジン－２－イル基、３－メチルピリジン－４－イル基、３－メチルピリジン－５－イル基、３－メチルピリジン－６－イル基、４－メチルピリジン－２－イル基、４－メチルピリジン－３－イル基、２，６－ジメチルピリジン－３－イル基、２，６－ジメチルピリジン－４－イル基、３，６－ジメチルピリジン－２－イル基、３，６－ジメチルピリジン－４－イル基、３，６－ジメチルピリジン－５－イル基、２－フェニルピリジン－６－イル基、３－フェニルピリジン－６－イル基、４－フェニルピリジン－６－イル基、５－フェニルピリジン－６－イル基、２－フェニルピリジン－３－イル基、２－フェニルピリジン－５－イル基、３－フェニルピリジン－５－イル基、４－フェニルピリジン－３－イル基、３－フェニルピリジン－４－イル基、２－フェニルピリジン－４－イル基、
２－（２－ピリジル）フェニル基、３－（２－ピリジル）フェニル基、４－（２－ピリジル）フェニル基、２－（３－ピリジル）フェニル基、３－（３－ピリジル）フェニル基、４－（３－ピリジル）フェニル基、２－（４－ピリジル）フェニル基、３－（４－ピリジル）フェニル基、４－（４－ピリジル）フェニル基、２－（３－メチル－２－ピリジル）フェニル基、３－（３－メチル－２－ピリジル）フェニル基、４－（３－メチル－２－ピリジル）フェニル基、２－（４－メチル－２－ピリジル）フェニル基、３－（４－メチル－２－ピリジル）フェニル基、４－（４－メチル－２－ピリジル）フェニル基、２－（５－メチル－２－ピリジル）フェニル基、３－（５－メチル－２－ピリジル）フェニル基、４－（５－メチル－２－ピリジル）フェニル基、２－（６－メチル－２－ピリジル）フェニル基、３－（６－メチル－２－ピリジル）フェニル基、４－（６－メチル－２－ピリジル）フェニル基、２－（２－メチル－３－ピリジル）フェニル基、３－（２－メチル－３－ピリジル）フェニル基、４－（２－メチル－３－ピリジル）フェニル基、２－（４－メチル－３－ピリジル）フェニル基、３－（４－メチル－３－ピリジル）フェニル基、４－（４－メチル－３－ピリジル）フェニル基、２－（５－メチル－３－ピリジル）フェニル基、３－（５－メチル－３－ピリジル）フェニル基、４－（５－メチル－３－ピリジル）フェニル基、２－（６－メチル－３－ピリジル）フェニル基、３－（６－メチル－３－ピリジル）フェニル基、４－（６－メチル－３－ピリジル）フェニル基、２－（２－メチル－４－ピリジル）フェニル基、３－（２－メチル－４－ピリジル）フェニル基、４－（２－メチル－４－ピリジル）フェニル基、２－（３－メチル－４－ピリジル）フェニル基、３－（３－メチル－４－ピリジル）フェニル基、４－（３－メチル－４－ピリジル）フェニル基、２－（２，４－ジメチル－３－ピリジル）フェニル基、３－（２，４－ジメチル－３－ピリジル）フェニル基、４－（２，４－ジメチル－３－ピリジル）フェニル基、２－（３，５－ジメチル－４－ピリジル）フェニル基、３－（３，５－ジメチル－４－ピリジル）フェニル基、４－（３，５－ジメチル－４－ピリジル）フェニル基、２－（３－フェニル－２－ピリジル）フェニル基、３－（３－フェニル－２－ピリジル）フェニル基、４－（３－フェニル－２－ピリジル）フェニル基、２－（４－フェニル－２－ピリジル）フェニル基、３－（４－フェニル－２－ピリジル）フェニル基、４－（４－フェニル－２－ピリジル）フェニル基、２－（５－フェニル－２－ピリジル）フェニル基、３－（５－フェニル－２－ピリジル）フェニル基、４－（５－フェニル－２－ピリジル）フェニル基、２－（６－フェニル－２－ピリジル）フェニル基、３－（６－フェニル－２－ピリジル）フェニル基、４－（６－フェニル－２－ピリジル）フェニル基、２－（２－フェニル－３－ピリジル）フェニル基、３－（２－フェニル－３－ピリジル）フェニル基、４－（２－フェニル－３－ピリジル）フェニル基、２－（４－フェニル－３－ピリジル）フェニル基、３－（４－フェニル－３－ピリジル）フェニル基、４－（４－フェニル－３－ピリジル）フェニル基、２－（５－フェニル－３－ピリジル）フェニル基、３－（５－フェニル－３－ピリジル）フェニル基、４－（５－フェニル－３－ピリジル）フェニル基、２－（６－フェニル－３－ピリジル）フェニル基、３－（６－フェニル－３－ピリジル）フェニル基、４－（６－フェニル－３－ピリジル）フェニル基、２－（２－フェニル－４－ピリジル）フェニル基、３－（２－フェニル－４－ピリジル）フェニル基、４－（２－フェニル－４－ピリジル）フェニル基、２－（３－フェニル－４－ピリジル）フェニル基、３－（３－フェニル－４－ピリジル）フェニル基、４－（３－フェニル－４－ピリジル）フェニル基、２－（２，４－ジフェニル－３－ピリジル）フェニル基、３－（２，４－ジフェニル－３－ピリジル）フェニル基、４－（２，４－ジフェニル－３－ピリジル）フェニル基、２－（３，５－ジフェニル－４－ピリジル）フェニル基、３－（３，５－ジフェニル－４－ピリジル）フェニル基、４－（３，５－ジフェニル－４－ピリジル）フェニル基、
２－（１－ナフチル）フェニル基、３－（１－ナフチル）フェニル基、４－（１－ナフチル）フェニル基、２－（２－ナフチル）フェニル基、３－（２－ナフチル）フェニル基、４－（２－ナフチル）フェニル基、２－（１－フェナントリル）フェニル基、３－（１－フェナントリル）フェニル基、４－（１－フェナントリル）フェニル基、２－（２－フェナントリル）フェニル基、３－（２－フェナントリル）フェニル基、４－（２－フェナントリル）フェニル基、２－（３－フェナントリル）フェニル基、３－（３－フェナントリル）フェニル基、４－（３－フェナントリル）フェニル基、２－（４－フェナントリル）フェニル基、３－（４－フェナントリル）フェニル基、４－（４－フェナントリル）フェニル基、２－（９－フェナントリル）フェニル基、３－（９－フェナントリル）フェニル基、４－（９－フェナントリル）フェニル基、２－（１－アントリル）フェニル基、３－（１－アントリル）フェニル基、４－（１－アントリル）フェニル基、２－（２－アントリル）フェニル基、３－（２－アントリル）フェニル基、４－（２－アントリル）フェニル基、２－（９－アントリル）フェニル基、３－（９－アントリル）フェニル基、４－（９－アントリル）フェニル基、２－（１－ピレニル）フェニル基、３－（１－ピレニル）フェニル基、４－（１－ピレニル）フェニル基、２－（２－ピレニル）フェニル基、３－（２－ピレニル）フェニル基、４－（２－ピレニル）フェニル基、２－（４－ピレニル）フェニル基、３－（４－ピレニル）フェニル基、４－（４－ピレニル）フェニル基、２－（フルオランテン－１－イル）フェニル基、３－（フルオランテン－１－イル）フェニル基、４－（フルオランテン－１－イル）フェニル基、２－（フルオランテン－２－イル）フェニル基、３－（フルオランテン－２－イル）フェニル基、４－（フルオランテン－２－イル）フェニル基、２－（フルオランテン－３－イル）フェニル基、３－（フルオランテン－３－イル）フェニル基、４－（フルオランテン－３－イル）フェニル基、２－（フルオランテン－４－イル）フェニル基、３－（フルオランテン－４－イル）フェニル基、４－（フルオランテン－４－イル）フェニル基、２－（フルオランテン－５－イル）フェニル基、３－（フルオランテン－５－イル）フェニル基、４－（フルオランテン－５－イル）フェニル基、２－（トリフェニレン－１－イル）フェニル基、３－（トリフェニレン－１－イル）フェニル基、４－（トリフェニレン－１－イル）フェニル基、２－（トリフェニレン－２－イル）フェニル基、３－（トリフェニレン－２－イル）フェニル基、４－（トリフェニレン－２－イル）フェニル基、２－（クリセン－１－イル）フェニル基、３－（クリセン－１－イル）フェニル基、４－（クリセン－１－イル）フェニル基、２－（クリセン－２－イル）フェニル基、３－（クリセン－２－イル）フェニル基、４－（クリセン－２－イル）フェニル基、２－（クリセン－３－イル）フェニル基、３－（クリセン－３－イル）フェニル基、４－（クリセン－３－イル）フェニル基、２－（クリセン－４－イル）フェニル基、３－（クリセン－４－イル）フェニル基、４－（クリセン－４－イル）フェニル基、２－（クリセン－５－イル）フェニル基、３－（クリセン－５－イル）フェニル基、４－（クリセン－５－イル）フェニル基、２－（クリセン－６－イル）フェニル基、３－（クリセン－６－イル）フェニル基、４－（クリセン－６－イル）フェニル基、２－（アセナフチレン－１－イル）フェニル基、３－（アセナフチレン－１－イル）フェニル基、４－（アセナフチレン－１－イル）フェニル基、２－（アセナフチレン－３－イル）フェニル基、３－（アセナフチレン－３－イル）フェニル基、４－（アセナフチレン－３－イル）フェニル基、２－（アセナフチレン－４－イル）フェニル基、３－（アセナフチレン－４－イル）フェニル基、４－（アセナフチレン－４－イル）フェニル基、２－（アセナフチレン－５－イル）フェニル基、３－（アセナフチレン－５－イル）フェニル基、４－（アセナフチレン－５－イル）フェニル基、
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３－（２－ピリジル）ビフェニル－４－イル基、２’－（２－ピリジル）ビフェニル－４－イル基、４’－（２－ピリジル）ビフェニル－４－イル基、２，２’－ジ（２－ピリジル）ビフェニル－４－イル基、２’，４’，６’－トリ（２－ピリジル）ビフェニル－４－イル基、６－（２－ピリジル）ビフェニル－３－イル基、５－（２－ピリジル）ビフェニル－３－イル基、２’－（２－ピリジル）ビフェニル－３－イル基、４’－（２－ピリジル）ビフェニル－３－イル基、６，２’－ジ（２－ピリジル）ビフェニル－３－イル基、５－（２－ピリジル）ビフェニル－２－イル基、６－（２－ピリジル）ビフェニル－２－イル基、２’－（２－ピリジル）ビフェニル－２－イル基、４’－（２－ピリジル）ビフェニル－２－イル基、６，２’－ジ（２－ピリジル）ビフェニル－２－イル基、３－（３－ピリジル）ビフェニル－４－イル基、２’－（３－ピリジル）ビフェニル－４－イル基、４’－（３－ピリジル）ビフェニル－４－イル基、２，２’－ジ（３－ピリジル）ビフェニル－４－イル基、２’，４’，６’－トリ（３－ピリジル）ビフェニル－４－イル基、６－（３－ピリジル）ビフェニル－３－イル基、５－（３－ピリジル）ビフェニル－３－イル基、２’－（３－ピリジル）ビフェニル－３－イル基、４’－（３－ピリジル）ビフェニル－３－イル基、６，２’－ジ（３－ピリジル）ビフェニル－３－イル基、５－（３－ピリジル）ビフェニル－２－イル基、６－（３－ピリジル）ビフェニル－２－イル基、２’－（３－ピリジル）ビフェニル－２－イル基、４’－（３－ピリジル）ビフェニル－２－イル基、６，２’－ジ（３－ピリジル）ビフェニル－２－イル基、３－（４－ピリジル）ビフェニル－４－イル基、２’－（４－ピリジル）ビフェニル－４－イル基、４’－（４－ピリジル）ビフェニル－４－イル基、２，２’－ジ（４－ピリジル）ビフェニル－４－イル基、２’，４’，６’－トリ（４－ピリジル）ビフェニル－４－イル基、６－（４－ピリジル）ビフェニル－３－イル基、５－（４－ピリジル）ビフェニル－３－イル基、２’－（４－ピリジル）ビフェニル－３－イル基、４’－（４－ピリジル）ビフェニル－３－イル基、６，２’－ジ（４－ピリジル）ビフェニル－３－イル基、５－（４－ピリジル）ビフェニル－２－イル基、６－（４－ピリジル）ビフェニル－２－イル基、２’－（４－ピリジル）ビフェニル－２－イル基、４’－（４－ピリジル）ビフェニル－２－イル基、６，２’－ジ（４－ピリジル）ビフェニル－２－イル基、３－（１－ナフチル）ビフェニル－４－イル基、２’－（１－ナフチル）ビフェニル－４－イル基、４’－（１－ナフチル）ビフェニル－４－イル基、２，２’－ジ（１－ナフチル）ビフェニル－４－イル基、２’，４’，６’－トリ（１－ナフチル）ビフェニル－４－イル基、６－（１－ナフチル）ビフェニル－３－イル基、５－（１－ナフチル）ビフェニル－３－イル基、２’－（１－ナフチル）ビフェニル－３－イル基、４’－（１－ナフチル）ビフェニル－３－イル基、６，２’－ジ（１－ナフチル）ビフェニル－３－イル基、５－（１－ナフチル）ビフェニル－２－イル基、６－（１－ナフチル）ビフェニル－２－イル基、２’－（１－ナフチル）ビフェニル－２－イル基、４’－（１－ナフチル）ビフェニル－２－イル基、６，２’－ジ（１－ナフチル）ビフェニル－２－イル基、３－（２－ナフチル）ビフェニル－４－イル基、２’－（２－ナフチル）ビフェニル－４－イル基、４’－（２－ナフチル）ビフェニル－４－イル基、２，２’－ジ（２－ナフチル）ビフェニル－４－イル基、２’，４’，６’－トリ（２－ナフチル）ビフェニル－４－イル基、６－（２－ナフチル）ビフェニル－３－イル基、５－（２－ナフチル）ビフェニル－３－イル基、２’－（２－ナフチル）ビフェニル－３－イル基、４’－（２－ナフチル）ビフェニル－３－イル基、６，２’－ジ（２－ナフチル）ビフェニル－３－イル基、５－（２－ナフチル）ビフェニル－２－イル基、６－（２－ナフチル）ビフェニル－２－イル基、２’－（２－ナフチル）ビフェニル－２－イル基、４’－（２－ナフチル）ビフェニル－２－イル基、６，２’－ジ（２－ナフチル）ビフェニル－２－イル基、
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フェナントリジン－１－イル基、フェナントリジン－１－イル基、フェナントリジン－２－イル基、フェナントリジン－３－イル基、フェナントリジン－４－イル基、フェナントリジン－６－イル基、フェナントリジン－７－イル基、フェナントリジン－８－イル基、フェナントリジン－９－イル基、フェナントリジン－１０－イル基、フェナジン－１－イル基、フェナジン－２－イル基、ベンゾ［ｈ］キノリン－２－イル基、ベンゾ［ｈ］キノリン－３－イル基、ベンゾ［ｈ］キノリン－４－イル基、ベンゾ［ｈ］キノリン－５－イル基、ベンゾ［ｈ］キノリン－６－イル基、ベンゾ［ｈ］キノリン－７－イル基、ベンゾ［ｈ］キノリン－８－イル基、ベンゾ［ｈ］キノリン－９－イル基、ベンゾ［ｈ］キノリン－１０－イル基、２－チエニル基、３－チエニル基、２－フリル基、３－フリル基、ベンゾチオフェン－２－イル基、ベンゾチオフェン－３－イル基、ベンゾチオフェン－４－イル基、ベンゾチオフェン－５－イル基、ベンゾチオフェン－６－イル基、ベンゾチオフェン－７－イル基、ベンゾフラン－２－イル基、ベンゾフラン－３－イル基、ベンゾフラン－４－イル基、ベンゾフラン－５－イル基、ベンゾフラン－６－イル基、ベンゾフラン－７－イル基、ジベンゾチオフェン－１－イル基、ジベンゾチオフェン－２－イル基、ジベンゾチオフェン－３－イル基、ジベンゾフラン－１－イル基、ジベンゾフラン－２－イル基、ジベンゾフラン－３－イル基、３－メチルチオフェン－２－イル基、４－メチルチオフェン－２－イル基、５－メチルチオフェン－２－イル基、２－メチルチオフェン－３－イル基、４－メチルチオフェン－３－イル基、５－メチルチオフェン－３－イル基、３－メチルフラン－２－イル基、４－メチルフラン－２－イル基、５－メチルフラン－２－イル基、２－メチルフラン－３－イル基、４－メチルフラン－３－イル基、５－メチルフラン－３－イル基、３－メチルベンゾチオフェン－２－イル基、４－メチルベンゾチオフェン－２－イル基、５－メチルベンゾチオフェン－２－イル基、６－メチルベンゾチオフェン－２－イル基、７－メチルベンゾチオフェン－２－イル基、２－メチルベンゾチオフェン－３－イル基、４－メチルベンゾチオフェン－３－イル基、５－メチルベンゾチオフェン－３－イル基、６－メチルベンゾチオフェン－３－イル基、７－メチルベンゾチオフェン－３－イル基、２－メチルベンゾチオフェン－４－イル基、３－メチルベンゾチオフェン－４－イル基、５－メチルベンゾチオフェン－４－イル基、６－メチルベンゾチオフェン－４－イル基、７－メチルベンゾチオフェン－４－イル基、２－メチルベンゾチオフェン－５－イル基、３－メチルベンゾチオフェン－５－イル基、４－メチルベンゾチオフェン－５－イル基、６－メチルベンゾチオフェン－５－イル基、７－メチルベンゾチオフェン－５－イル基、２－メチルベンゾチオフェン－６－イル基、３－メチルベンゾチオフェン－６－イル基、４－メチルベンゾチオフェン－６－イル基、５－メチルベンゾチオフェン－６－イル基、７－メチルベンゾチオフェン－６－イル基、２－メチルベンゾチオフェン－７－イル基、３－メチルベンゾチオフェン－７－イル基、４－メチルベンゾチオフェン－７－イル基、５－メチルベンゾチオフェン－７－イル基、６－メチルベンゾチオフェン－７－イル基、３－メチルベンゾフラン－２－イル基、４－メチルベンゾフラン－２－イル基、５－メチルベンゾフラン－２－イル基、６－メチルベンゾフラン－２－イル基、７－メチルベンゾフラン－２－イル基、２－メチルベンゾフラン－３－イル基、４－メチルベンゾフラン－３－イル基、５－メチルベンゾフラン－３－イル基、６－メチルベンゾフラン－３－イル基、７－メチルベンゾフラン－３－イル基、２－メチルベンゾフラン－４－イル基、３－メチルベンゾフラン－４－イル基、５－メチルベンゾフラン－４－イル基、６－メチルベンゾフラン－４－イル基、７－メチルベンゾフラン－４－イル基、２－メチルベンゾフラン－５－イル基、３－メチルベンゾフラン－５－イル基、４－メチルベンゾフラン－５－イル基、６－メチルベンゾフラン－５－イル基、７－メチルベンゾフラン－５－イル基、２－メチルベンゾフラン－６－イル基、３－メチルベンゾフラン－６－イル基、４－メチルベンゾフラン－６－イル基、５－メチルベンゾフラン－６－イル基、７－メチルベンゾフラン－６－イル基、２－メチルベンゾフラン－７－イル基、３－メチルベンゾフラン－７－イル基、４－メチルベンゾフラン－７－イル基、５－メチルベンゾフラン－７－イル基、６－メチルベンゾフラン－７－イル基、２－メチルジベンゾチオフェン－１－イル基、３－メチルジベンゾチオフェン－１－イル基、４－メチルジベンゾチオフェン－１－イル基、６－メチルジベンゾチオフェン－１－イル基、７－メチルジベンゾチオフェン－１－イル基、８－メチルジベンゾチオフェン－１－イル基、９－メチルジベンゾチオフェン－１－イル基、１－メチルジベンゾチオフェン－２－イル基、３－メチルジベンゾチオフェン－２－イル基、４－メチルジベンゾチオフェン－２－イル基、６－メチルジベンゾチオフェン－２－イル基、７－メチルジベンゾチオフェン－２－イル基、８－メチルジベンゾチオフェン－２－イル基、９－メチルジベンゾチオフェン－２－イル基、１－メチルジベンゾチオフェン－３－イル基、２－メチルジベンゾチオフェン－３－イル基、４－メチルジベンゾチオフェン－３－イル基、６－メチルジベンゾチオフェン－３－イル基、７－メチルジベンゾチオフェン－３－イル基、８－メチルジベンゾチオフェン－３－イル基、９－メチルジベンゾチオフェン－３－イル基、２－メチルジベンゾフラン－１－イル基、３－メチルジベンゾフラン－１－イル基、４－メチルジベンゾフラン－１－イル基、６－メチルジベンゾフラン－１－イル基、７－メチルジベンゾフラン－１－イル基、８－メチルジベンゾフラン－１－イル基、９－メチルジベンゾフラン－１－イル基、１－メチルジベンゾフラン－２－イル基、３－メチルジベンゾフラン－２－イル基、４－メチルジベンゾフラン－２－イル基、６－メチルジベンゾフラン－２－イル基、７－メチルジベンゾフラン－２－イル基、８－メチルジベンゾフラン－２－イル基、９－メチルジベンゾフラン－２－イル基、１－メチルジベンゾフラン－３－イル基、２－メチルジベンゾフラン－３－イル基、４－メチルジベンゾフラン－３－イル基、６－メチルジベンゾフラン－３－イル基、７－メチルジベンゾフラン－３－イル基、８－メチルジベンゾフラン－３－イル基、９－メチルジベンゾフラン－３－イル基、３－フェニルチオフェン－２－イル基、４－フェニルチオフェン－２－イル基、５－フェニルチオフェン－２－イル基、２－フェニルチオフェン－３－イル基、４－フェニルチオフェン－３－イル基、５－フェニルチオフェン－３－イル基、３－フェニルフラン－２－イル基、４－フェニルフラン－２－イル基、５－フェニルフラン－２－イル基、２－フェニルフラン－３－イル基、４－フェニルフラン－３－イル基、５－フェニルフラン－３－イル基、３－フェニルベンゾチオフェン－２－イル基、４－フェニルベンゾチオフェン－２－イル基、５－フェニルベンゾチオフェン－２－イル基、６－フェニルベンゾチオフェン－２－イル基、７－フェニルベンゾチオフェン－２－イル基、２－フェニルベンゾチオフェン－３－イル基、４－フェニルベンゾチオフェン－３－イル基、５－フェニルベンゾチオフェン－３－イル基、６－フェニルベンゾチオフェン－３－イル基、７－フェニルベンゾチオフェン－３－イル基、２－フェニルベンゾチオフェン－４－イル基、３－フェニルベンゾチオフェン－４－イル基、５－フェニルベンゾチオフェン－４－イル基、６－フェニルベンゾチオフェン－４－イル基、７－フェニルベンゾチオフェン－４－イル基、２－フェニルベンゾチオフェン－５－イル基、３－フェニルベンゾチオフェン－５－イル基、４－フェニルベンゾチオフェン－５－イル基、６－フェニルベンゾチオフェン－５－イル基、７－フェニルベンゾチオフェン－５－イル基、２－フェニルベンゾチオフェン－６－イル基、３－フェニルベンゾチオフェン－６－イル基、４－フェニルベンゾチオフェン－６－イル基、５－フェニルベンゾチオフェン－６－イル基、７－フェニルベンゾチオフェン－６－イル基、２－フェニルベンゾチオフェン－７－イル基、３－フェニルベンゾチオフェン－７－イル基、４－フェニルベンゾチオフェン－７－イル基、５－フェニルベンゾチオフェン－７－イル基、６－フェニルベンゾチオフェン－７－イル基、３－フェニルベンゾフラン－２－イル基、４－フェニルベンゾフラン－２－イル基、５－フェニルベンゾフラン－２－イル基、６－フェニルベンゾフラン－２－イル基、７－フェニルベンゾフラン－２－イル基、２－フェニルベンゾフラン－３－イル基、４－フェニルベンゾフラン－３－イル基、５－フェニルベンゾフラン－３－イル基、６－フェニルベンゾフラン－３－イル基、７－フェニルベンゾフラン－３－イル基、２－フェニルベンゾフラン－４－イル基、３－フェニルベンゾフラン－４－イル基、５－フェニルベンゾフラン－４－イル基、６－フェニルベンゾフラン－４－イル基、７－フェニルベンゾフラン－４－イル基、２－フェニルベンゾフラン－５－イル基、３－フェニルベンゾフラン－５－イル基、４－フェニルベンゾフラン－５－イル基、６－フェニルベンゾフラン－５－イル基、７－フェニルベンゾフラン－５－イル基、２－フェニルベンゾフラン－６－イル基、３－フェニルベンゾフラン－６－イル基、４－フェニルベンゾフラン－６－イル基、５－フェニルベンゾフラン－６－イル基、７－フェニルベンゾフラン－６－イル基、２－フェニルベンゾフラン－７－イル基、３－フェニルベンゾフラン－７－イル基、４－フェニルベンゾフラン－７－イル基、５－フェニルベンゾフラン－７－イル基、６－フェニルベンゾフラン－７－イル基、２－フェニルジベンゾチオフェン－１－イル基、３－フェニルジベンゾチオフェン－１－イル基、４－フェニルジベンゾチオフェン－１－イル基、６－フェニルジベンゾチオフェン－１－イル基、７－フェニルジベンゾチオフェン－１－イル基、８－フェニルジベンゾチオフェン－１－イル基、９－フェニルジベンゾチオフェン－１－イル基、１－フェニルジベンゾチオフェン－２－イル基、３－フェニルジベンゾチオフェン－２－イル基、４－フェニルジベンゾチオフェン－２－イル基、６－フェニルジベンゾチオフェン－２－イル基、７－フェニルジベンゾチオフェン－２－イル基、８－フェニルジベンゾチオフェン－２－イル基、９－フェニルジベンゾチオフェン－２－イル基、１－フェニルジベンゾチオフェン－３－イル基、２－フェニルジベンゾチオフェン－３－イル基、４－フェニルジベンゾチオフェン－３－イル基、６－フェニルジベンゾチオフェン－３－イル基、７－フェニルジベンゾチオフェン－３－イル基、８－フェニルジベンゾチオフェン－３－イル基、９－フェニルジベンゾチオフェン－３－イル基、
２－フェニルジベンゾフラン－１－イル基、３－フェニルジベンゾフラン－１－イル基、４－フェニルジベンゾフラン－１－イル基、６－フェニルジベンゾフラン－１－イル基、７－フェニルジベンゾフラン－１－イル基、８－フェニルジベンゾフラン－１－イル基、９－フェニルジベンゾフラン－１－イル基、１－フェニルジベンゾフラン－２－イル基、３－フェニルジベンゾフラン－２－イル基、４－フェニルジベンゾフラン－２－イル基、６－フェニルジベンゾフラン－２－イル基、７－フェニルジベンゾフラン－２－イル基、８－フェニルジベンゾフラン－２－イル基、９－フェニルジベンゾフラン－２－イル基、１－フェニルジベンゾフラン－３－イル基、２－フェニルジベンゾフラン－３－イル基、４－フェニルジベンゾフラン－３－イル基、６－フェニルジベンゾフラン－３－イル基、７－フェニルジベンゾフラン－３－イル基、８－フェニルジベンゾフラン－３－イル基、９－フェニルジベンゾフラン－３－イル基、３－（２－ピリジル）チオフェン－２－イル基、４－（２－ピリジル）チオフェン－２－イル基、５－（２－ピリジル）チオフェン－２－イル基、２－（２－ピリジル）チオフェン－３－イル基、４－（２－ピリジル）チオフェン－３－イル基、５－（２－ピリジル）チオフェン－３－イル基、３－（２－ピリジル）フラン－２－イル基、４－（２－ピリジル）フラン－２－イル基、５－（２－ピリジル）フラン－２－イル基、２－（２－ピリジル）フラン－３－イル基、４－（２－ピリジル）フラン－３－イル基、５－（２－ピリジル）フラン－３－イル基、３－（２－ピリジル）ベンゾチオフェン－２－イル基、４－（２－ピリジル）ベンゾチオフェン－２－イル基、５－（２－ピリジル）ベンゾチオフェン－２－イル基、６－（２－ピリジル）ベンゾチオフェン－２－イル基、７－（２－ピリジル）ベンゾチオフェン－２－イル基、２－（２－ピリジル）ベンゾチオフェン－３－イル基、４－（２－ピリジル）ベンゾチオフェン－３－イル基、５－（２－ピリジル）ベンゾチオフェン－３－イル基、６－（２－ピリジル）ベンゾチオフェン－３－イル基、７－（２－ピリジル）ベンゾチオフェン－３－イル基、２－（２－ピリジル）ベンゾチオフェン－４－イル基、３－（２－ピリジル）ベンゾチオフェン－４－イル基、５－（２－ピリジル）ベンゾチオフェン－４－イル基、６－（２－ピリジル）ベンゾチオフェン－４－イル基、７－（２－ピリジル）ベンゾチオフェン－４－イル基、２－（２－ピリジル）ベンゾチオフェン－５－イル基、３－（２－ピリジル）ベンゾチオフェン－５－イル基、４－（２－ピリジル）ベンゾチオフェン－５－イル基、６－（２－ピリジル）ベンゾチオフェン－５－イル基、７－（２－ピリジル）ベンゾチオフェン－５－イル基、２－（２－ピリジル）ベンゾチオフェン－６－イル基、３－（２－ピリジル）ベンゾチオフェン－６－イル基、４－（２－ピリジル）ベンゾチオフェン－６－イル基、５－（２－ピリジル）ベンゾチオフェン－６－イル基、７－（２－ピリジル）ベンゾチオフェン－６－イル基、２－（２－ピリジル）ベンゾチオフェン－７－イル基、３－（２－ピリジル）ベンゾチオフェン－７－イル基、４－（２－ピリジル）ベンゾチオフェン－７－イル基、５－（２－ピリジル）ベンゾチオフェン－７－イル基、６－（２－ピリジル）ベンゾチオフェン－７－イル基、３－（２－ピリジル）ベンゾフラン－２－イル基、４－（２－ピリジル）ベンゾフラン－２－イル基、５－（２－ピリジル）ベンゾフラン－２－イル基、６－（２－ピリジル）ベンゾフラン－２－イル基、７－（２－ピリジル）ベンゾフラン－２－イル基、２－（２－ピリジル）ベンゾフラン－３－イル基、４－（２－ピリジル）ベンゾフラン－３－イル基、５－（２－ピリジル）ベンゾフラン－３－イル基、６－（２－ピリジル）ベンゾフラン－３－イル基、７－（２－ピリジル）ベンゾフラン－３－イル基、２－（２－ピリジル）ベンゾフラン－４－イル基、３－（２－ピリジル）ベンゾフラン－４－イル基、５－（２－ピリジル）ベンゾフラン－４－イル基、６－（２－ピリジル）ベンゾフラン－４－イル基、７－（２－ピリジル）ベンゾフラン－４－イル基、２－（２－ピリジル）ベンゾフラン－５－イル基、３－（２－ピリジル）ベンゾフラン－５－イル基、４－（２－ピリジル）ベンゾフラン－５－イル基、６－（２－ピリジル）ベンゾフラン－５－イル基、７－（２－ピリジル）ベンゾフラン－５－イル基、２－（２－ピリジル）ベンゾフラン－６－イル基、３－（２－ピリジル）ベンゾフラン－６－イル基、４－（２－ピリジル）ベンゾフラン－６－イル基、５－（２－ピリジル）ベンゾフラン－６－イル基、７－（２－ピリジル）ベンゾフラン－６－イル基、２－（２－ピリジル）ベンゾフラン－７－イル基、３－（２－ピリジル）ベンゾフラン－７－イル基、４－（２－ピリジル）ベンゾフラン－７－イル基、５－（２－ピリジル）ベンゾフラン－７－イル基、６－（２－ピリジル）ベンゾフラン－７－イル基、２－（２－ピリジル）ジベンゾチオフェン－１－イル基、３－（２－ピリジル）ジベンゾチオフェン－１－イル基、４－（２－ピリジル）ジベンゾチオフェン－１－イル基、６－（２－ピリジル）ジベンゾチオフェン－１－イル基、７－（２－ピリジル）ジベンゾチオフェン－１－イル基、８－（２－ピリジル）ジベンゾチオフェン－１－イル基、９－（２－ピリジル）ジベンゾチオフェン－１－イル基、１－（２－ピリジル）ジベンゾチオフェン－２－イル基、３－（２－ピリジル）ジベンゾチオフェン－２－イル基、４－（２－ピリジル）ジベンゾチオフェン－２－イル基、６－（２－ピリジル）ジベンゾチオフェン－２－イル基、７－（２－ピリジル）ジベンゾチオフェン－２－イル基、８－（２－ピリジル）ジベンゾチオフェン－２－イル基、９－（２－ピリジル）ジベンゾチオフェン－２－イル基、１－（２－ピリジル）ジベンゾチオフェン－３－イル基、２－（２－ピリジル）ジベンゾチオフェン－３－イル基、４－（２－ピリジル）ジベンゾチオフェン－３－イル基、６－（２－ピリジル）ジベンゾチオフェン－３－イル基、７－（２－ピリジル）ジベンゾチオフェン－３－イル基、８－（２－ピリジル）ジベンゾチオフェン－３－イル基、９－（２－ピリジル）ジベンゾチオフェン－３－イル基、
２－（２－ピリジル）ジベンゾフラン－１－イル基、３－（２－ピリジル）ジベンゾフラン－１－イル基、４－（２－ピリジル）ジベンゾフラン－１－イル基、６－（２－ピリジル）ジベンゾフラン－１－イル基、７－（２－ピリジル）ジベンゾフラン－１－イル基、８－（２－ピリジル）ジベンゾフラン－１－イル基、９－（２－ピリジル）ジベンゾフラン－１－イル基、１－（２－ピリジル）ジベンゾフラン－２－イル基、３－（２－ピリジル）ジベンゾフラン－２－イル基、４－（２－ピリジル）ジベンゾフラン－２－イル基、６－（２－ピリジル）ジベンゾフラン－２－イル基、７－（２－ピリジル）ジベンゾフラン－２－イル基、８－（２－ピリジル）ジベンゾフラン－２－イル基、９－（２－ピリジル）ジベンゾフラン－２－イル基、１－（２－ピリジル）ジベンゾフラン－３－イル基、２－（２－ピリジル）ジベンゾフラン－３－イル基、４－（２－ピリジル）ジベンゾフラン－３－イル基、６－（２－ピリジル）ジベンゾフラン－３－イル基、７－（２－ピリジル）ジベンゾフラン－３－イル基、８－（２－ピリジル）ジベンゾフラン－３－イル基、９－（２－ピリジル）ジベンゾフラン－３－イル基、３－（３－ピリジル）チオフェン－２－イル基、４－（３－ピリジル）チオフェン－２－イル基、５－（３－ピリジル）チオフェン－２－イル基、２－（３－ピリジル）チオフェン－３－イル基、４－（３－ピリジル）チオフェン－３－イル基、５－（３－ピリジル）チオフェン－３－イル基、３－（３－ピリジル）フラン－２－イル基、４－（３－ピリジル）フラン－２－イル基、５－（３－ピリジル）フラン－２－イル基、２－（３－ピリジル）フラン－３－イル基、４－（３－ピリジル）フラン－３－イル基、５－（３－ピリジル）フラン－３－イル基、３－（３－ピリジル）ベンゾチオフェン－２－イル基、４－（３－ピリジル）ベンゾチオフェン－２－イル基、５－（３－ピリジル）ベンゾチオフェン－２－イル基、６－（３－ピリジル）ベンゾチオフェン－２－イル基、７－（３－ピリジル）ベンゾチオフェン－２－イル基、２－（３－ピリジル）ベンゾチオフェン－３－イル基、４－（３－ピリジル）ベンゾチオフェン－３－イル基、５－（３－ピリジル）ベンゾチオフェン－３－イル基、６－（３－ピリジル）ベンゾチオフェン－３－イル基、７－（３－ピリジル）ベンゾチオフェン－３－イル基、２－（３－ピリジル）ベンゾチオフェン－４－イル基、３－（３－ピリジル）ベンゾチオフェン－４－イル基、５－（３－ピリジル）ベンゾチオフェン－４－イル基、６－（３－ピリジル）ベンゾチオフェン－４－イル基、７－（３－ピリジル）ベンゾチオフェン－４－イル基、２－（３－ピリジル）ベンゾチオフェン－５－イル基、３－（３－ピリジル）ベンゾチオフェン－５－イル基、４－（３－ピリジル）ベンゾチオフェン－５－イル基、６－（３－ピリジル）ベンゾチオフェン－５－イル基、７－（３－ピリジル）ベンゾチオフェン－５－イル基、２－（３－ピリジル）ベンゾチオフェン－６－イル基、３－（３－ピリジル）ベンゾチオフェン－６－イル基、４－（３－ピリジル）ベンゾチオフェン－６－イル基、５－（３－ピリジル）ベンゾチオフェン－６－イル基、７－（３－ピリジル）ベンゾチオフェン－６－イル基、２－（３－ピリジル）ベンゾチオフェン－７－イル基、３－（３－ピリジル）ベンゾチオフェン－７－イル基、４－（３－ピリジル）ベンゾチオフェン－７－イル基、５－（３－ピリジル）ベンゾチオフェン－７－イル基、６－（３－ピリジル）ベンゾチオフェン－７－イル基、３－（３－ピリジル）ベンゾフラン－２－イル基、４－（３－ピリジル）ベンゾフラン－２－イル基、５－（３－ピリジル）ベンゾフラン－２－イル基、６－（３－ピリジル）ベンゾフラン－２－イル基、７－（３－ピリジル）ベンゾフラン－２－イル基、２－（３－ピリジル）ベンゾフラン－３－イル基、４－（３－ピリジル）ベンゾフラン－３－イル基、５－（３－ピリジル）ベンゾフラン－３－イル基、６－（３－ピリジル）ベンゾフラン－３－イル基、７－（３－ピリジル）ベンゾフラン－３－イル基、２－（３－ピリジル）ベンゾフラン－４－イル基、３－（３－ピリジル）ベンゾフラン－４－イル基、５－（３－ピリジル）ベンゾフラン－４－イル基、６－（３－ピリジル）ベンゾフラン－４－イル基、７－（３－ピリジル）ベンゾフラン－４－イル基、２－（３－ピリジル）ベンゾフラン－５－イル基、３－（３－ピリジル）ベンゾフラン－５－イル基、４－（３－ピリジル）ベンゾフラン－５－イル基、６－（３－ピリジル）ベンゾフラン－５－イル基、７－（３－ピリジル）ベンゾフラン－５－イル基、２－（３－ピリジル）ベンゾフラン－６－イル基、３－（３－ピリジル）ベンゾフラン－６－イル基、４－（３－ピリジル）ベンゾフラン－６－イル基、５－（３－ピリジル）ベンゾフラン－６－イル基、７－（３－ピリジル）ベンゾフラン－６－イル基、２－（３－ピリジル）ベンゾフラン－７－イル基、３－（３－ピリジル）ベンゾフラン－７－イル基、４－（３－ピリジル）ベンゾフラン－７－イル基、５－（３－ピリジル）ベンゾフラン－７－イル基、６－（３－ピリジル）ベンゾフラン－７－イル基、２－（３－ピリジル）ジベンゾチオフェン－１－イル基、３－（３－ピリジル）ジベンゾチオフェン－１－イル基、４－（３－ピリジル）ジベンゾチオフェン－１－イル基、６－（３－ピリジル）ジベンゾチオフェン－１－イル基、７－（３－ピリジル）ジベンゾチオフェン－１－イル基、８－（３－ピリジル）ジベンゾチオフェン－１－イル基、９－（３－ピリジル）ジベンゾチオフェン－１－イル基、１－（３－ピリジル）ジベンゾチオフェン－２－イル基、３－（３－ピリジル）ジベンゾチオフェン－２－イル基、４－（３－ピリジル）ジベンゾチオフェン－２－イル基、６－（３－ピリジル）ジベンゾチオフェン－２－イル基、７－（３－ピリジル）ジベンゾチオフェン－２－イル基、８－（３－ピリジル）ジベンゾチオフェン－２－イル基、９－（３－ピリジル）ジベンゾチオフェン－２－イル基、１－（３－ピリジル）ジベンゾチオフェン－３－イル基、２－（３－ピリジル）ジベンゾチオフェン－３－イル基、４－（３－ピリジル）ジベンゾチオフェン－３－イル基、６－（３－ピリジル）ジベンゾチオフェン－３－イル基、７－（３－ピリジル）ジベンゾチオフェン－３－イル基、８－（３－ピリジル）ジベンゾチオフェン－３－イル基、９－（３－ピリジル）ジベンゾチオフェン－３－イル基、２－（３－ピリジル）ジベンゾフラン－１－イル基、３－（３－ピリジル）ジベンゾフラン－１－イル基、４－（３－ピリジル）ジベンゾフラン－１－イル基、６－（３－ピリジル）ジベンゾフラン－１－イル基、７－（３－ピリジル）ジベンゾフラン－１－イル基、８－（３－ピリジル）ジベンゾフラン－１－イル基、９－（３－ピリジル）ジベンゾフラン－１－イル基、１－（３－ピリジル）ジベンゾフラン－２－イル基、３－（３－ピリジル）ジベンゾフラン－２－イル基、４－（３－ピリジル）ジベンゾフラン－２－イル基、６－（３－ピリジル）ジベンゾフラン－２－イル基、７－（３－ピリジル）ジベンゾフラン－２－イル基、８－（３－ピリジル）ジベンゾフラン－２－イル基、９－（３－ピリジル）ジベンゾフラン－２－イル基、１－（３－ピリジル）ジベンゾフラン－３－イル基、２－（３－ピリジル）ジベンゾフラン－３－イル基、４－（３－ピリジル）ジベンゾフラン－３－イル基、６－（３－ピリジル）ジベンゾフラン－３－イル基、７－（３－ピリジル）ジベンゾフラン－３－イル基、８－（３－ピリジル）ジベンゾフラン－３－イル基、９－（３－ピリジル）ジベンゾフラン－３－イル基、３－（４－ピリジル）チオフェン－２－イル基、４－（４－ピリジル）チオフェン－２－イル基、５－（４－ピリジル）チオフェン－２－イル基、２－（４－ピリジル）チオフェン－３－イル基、４－（４－ピリジル）チオフェン－３－イル基、５－（４－ピリジル）チオフェン－３－イル基、
３－（４－ピリジル）フラン－２－イル基、４－（４－ピリジル）フラン－２－イル基、５－（４－ピリジル）フラン－２－イル基、２－（４－ピリジル）フラン－３－イル基、４－（４－ピリジル）フラン－３－イル基、５－（４－ピリジル）フラン－３－イル基、３－（４－ピリジル）ベンゾチオフェン－２－イル基、４－（４－ピリジル）ベンゾチオフェン－２－イル基、５－（４－ピリジル）ベンゾチオフェン－２－イル基、６－（４－ピリジル）ベンゾチオフェン－２－イル基、７－（４－ピリジル）ベンゾチオフェン－２－イル基、２－（４－ピリジル）ベンゾチオフェン－３－イル基、４－（４－ピリジル）ベンゾチオフェン－３－イル基、５－（４－ピリジル）ベンゾチオフェン－３－イル基、６－（４－ピリジル）ベンゾチオフェン－３－イル基、７－（４－ピリジル）ベンゾチオフェン－３－イル基、２－（４－ピリジル）ベンゾチオフェン－４－イル基、３－（４－ピリジル）ベンゾチオフェン－４－イル基、５－（４－ピリジル）ベンゾチオフェン－４－イル基、６－（４－ピリジル）ベンゾチオフェン－４－イル基、７－（４－ピリジル）ベンゾチオフェン－４－イル基、２－（４－ピリジル）ベンゾチオフェン－５－イル基、３－（４－ピリジル）ベンゾチオフェン－５－イル基、４－（４－ピリジル）ベンゾチオフェン－５－イル基、６－（４－ピリジル）ベンゾチオフェン－５－イル基、７－（４－ピリジル）ベンゾチオフェン－５－イル基、２－（４－ピリジル）ベンゾチオフェン－６－イル基、３－（４－ピリジル）ベンゾチオフェン－６－イル基、４－（４－ピリジル）ベンゾチオフェン－６－イル基、５－（４－ピリジル）ベンゾチオフェン－６－イル基、７－（４－ピリジル）ベンゾチオフェン－６－イル基、２－（４－ピリジル）ベンゾチオフェン－７－イル基、３－（４－ピリジル）ベンゾチオフェン－７－イル基、４－（４－ピリジル）ベンゾチオフェン－７－イル基、５－（４－ピリジル）ベンゾチオフェン－７－イル基、６－（４－ピリジル）ベンゾチオフェン－７－イル基、３－（４－ピリジル）ベンゾフラン－２－イル基、４－（４－ピリジル）ベンゾフラン－２－イル基、５－（４－ピリジル）ベンゾフラン－２－イル基、６－（４－ピリジル）ベンゾフラン－２－イル基、７－（４－ピリジル）ベンゾフラン－２－イル基、２－（４－ピリジル）ベンゾフラン－３－イル基、４－（４－ピリジル）ベンゾフラン－３－イル基、５－（４－ピリジル）ベンゾフラン－３－イル基、６－（４－ピリジル）ベンゾフラン－３－イル基、７－（４－ピリジル）ベンゾフラン－３－イル基、２－（４－ピリジル）ベンゾフラン－４－イル基、３－（４－ピリジル）ベンゾフラン－４－イル基、５－（４－ピリジル）ベンゾフラン－４－イル基、６－（４－ピリジル）ベンゾフラン－４－イル基、７－（４－ピリジル）ベンゾフラン－４－イル基、２－（４－ピリジル）ベンゾフラン－５－イル基、３－（４－ピリジル）ベンゾフラン－５－イル基、４－（４－ピリジル）ベンゾフラン－５－イル基、６－（４－ピリジル）ベンゾフラン－５－イル基、７－（４－ピリジル）ベンゾフラン－５－イル基、２－（４－ピリジル）ベンゾフラン－６－イル基、３－（４－ピリジル）ベンゾフラン－６－イル基、４－（４－ピリジル）ベンゾフラン－６－イル基、５－（４－ピリジル）ベンゾフラン－６－イル基、７－（４－ピリジル）ベンゾフラン－６－イル基、２－（４－ピリジル）ベンゾフラン－７－イル基、３－（４－ピリジル）ベンゾフラン－７－イル基、４－（４－ピリジル）ベンゾフラン－７－イル基、５－（４－ピリジル）ベンゾフラン－７－イル基、６－（４－ピリジル）ベンゾフラン－７－イル基、２－（４－ピリジル）ジベンゾチオフェン－１－イル基、３－（４－ピリジル）ジベンゾチオフェン－１－イル基、４－（４－ピリジル）ジベンゾチオフェン－１－イル基、６－（４－ピリジル）ジベンゾチオフェン－１－イル基、７－（４－ピリジル）ジベンゾチオフェン－１－イル基、８－（４－ピリジル）ジベンゾチオフェン－１－イル基、９－（４－ピリジル）ジベンゾチオフェン－１－イル基、１－（４－ピリジル）ジベンゾチオフェン－２－イル基、３－（４－ピリジル）ジベンゾチオフェン－２－イル基、４－（４－ピリジル）ジベンゾチオフェン－２－イル基、６－（４－ピリジル）ジベンゾチオフェン－２－イル基、７－（４－ピリジル）ジベンゾチオフェン－２－イル基、８－（４－ピリジル）ジベンゾチオフェン－２－イル基、９－（４－ピリジル）ジベンゾチオフェン－２－イル基、１－（４－ピリジル）ジベンゾチオフェン－３－イル基、２－（４－ピリジル）ジベンゾチオフェン－３－イル基、４－（４－ピリジル）ジベンゾチオフェン－３－イル基、６－（４－ピリジル）ジベンゾチオフェン－３－イル基、７－（４－ピリジル）ジベンゾチオフェン－３－イル基、８－（４－ピリジル）ジベンゾチオフェン－３－イル基、９－（４－ピリジル）ジベンゾチオフェン－３－イル基、
２－（４－ピリジル）ジベンゾフラン－１－イル基、３－（４－ピリジル）ジベンゾフラン－１－イル基、４－（４－ピリジル）ジベンゾフラン－１－イル基、６－（４－ピリジル）ジベンゾフラン－１－イル基、７－（４－ピリジル）ジベンゾフラン－１－イル基、８－（４－ピリジル）ジベンゾフラン－１－イル基、９－（４－ピリジル）ジベンゾフラン－１－イル基、１－（４－ピリジル）ジベンゾフラン－２－イル基、３－（４－ピリジル）ジベンゾフラン－２－イル基、４－（４－ピリジル）ジベンゾフラン－２－イル基、６－（４－ピリジル）ジベンゾフラン－２－イル基、７－（４－ピリジル）ジベンゾフラン－２－イル基、８－（４－ピリジル）ジベンゾフラン－２－イル基、９－（４－ピリジル）ジベンゾフラン－２－イル基、１－（４－ピリジル）ジベンゾフラン－３－イル基、２－（４－ピリジル）ジベンゾフラン－３－イル基、４－（４－ピリジル）ジベンゾフラン－３－イル基、６－（４－ピリジル）ジベンゾフラン－３－イル基、７－（４－ピリジル）ジベンゾフラン－３－イル基、８－（４－ピリジル）ジベンゾフラン－３－イル基、９－（４－ピリジル）ジベンゾフラン－３－イル基、２－｛８－（２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（４－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（４－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（４－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（３－メチル－２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（３－メチル－２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（３－メチル－２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（２－メチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（２－メチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（２－メチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（３－メチル－４－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（３－メチル－４－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（３－メチル－４－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（２，６－ジメチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（２，６－ジメチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（２，６－ジメチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（２－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（２－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（２－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（５－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（５－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、４－｛８－（５－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、等が好ましい例として挙げられる。これらの置換基のうち、電子輸送性材料特性に優れる点で、フェニル基、ｐ－トリル基、ビフェニル－３－イル基、ビフェニル－４－イル基、３－（１－ナフチル）フェニル基、３－（２－ナフチル）フェニル基、４－（１－ナフチル）フェニル基、４－（２－ナフチル）フェニル基、３－（９－フェナントリル）フェニル基、４－（９－フェナントリル）フェニル基、３－（フルオランテン－３－イル）フェニル基、４－（フルオランテン－３－イル）フェニル基、３－（２－ピリジル）フェニル基、４－（２－ピリジル）フェニル基、３－（３－ピリジル）フェニル基、４－（３－ピリジル）フェニル基、３－（２－キノリル）フェニル基、４－（２－キノリル）フェニル基、３－（３－キノリル）フェニル基、４－（３－キノリル）フェニル基、３－（５－メチルチオフェン－２－イル）フェニル基、４－（５－メチルチオフェン－２－イル）フェニル基、３－（５－メチルフラン－２－イル）フェニル基、４－（５－メチルフラン－２－イル）フェニル基、３－（２－ベンゾチエニル）フェニル基、４－（２－ベンゾチエニル）フェニル基、３－（２－ベンゾフリル）フェニル基、４－（２－ベンゾフリル）フェニル基、３－（２－ジベンゾチエニル）フェニル基、４－（２－ジベンゾチエニル）フェニル基、３－（４－ジベンゾチエニル）フェニル基、４－（４－ジベンゾチエニル）フェニル基、３－（２－ジベンゾフリル）フェニル基、４－（２－ジベンゾフリル）フェニル基、３－（４－ジベンゾフリル）フェニル基、４－（４－ジベンゾフリル）フェニル基、２－フェニルピリジン－６－イル基、２－フェニルピリジン－５－イル基、２－フェニルピリジン－４－イル基、３－フェニルピリジン－５－イル基、３－フェニルピリジン－６－イル基、５－フェニルチオフェン－２－イル基、５－フェニルフラン－２－イル基、１－ナフチル基、２－ナフチル基、２－ベンゾチエニル基、２－ベンゾフリル基、１－フェナントリル基、２－フェナントリル基、３－フェナントリル基、９－フェナントリル基、２－ジベンゾチエニル基、２－ジベンゾフリル基、４－ジベンゾチエニル基、４－ジベンゾフリル基、２－｛８－（３－メチル－２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（３－メチル－２－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（２，６－ジメチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、３－｛８－（２，６－ジメチル－３－ピリジル）ジベンゾフラン－２－イル｝フェニル基、２－｛８－（２－ピリミジル）ジベンゾフラン－２－イル｝フェニル基、又は３－｛８－（２－ピリミジル）ジベンゾフラン－２－イル｝フェニル基が好ましく、フェニル基、ビフェニル－３－イル基、ビフェニル－４－イル基、３－（１－ナフチル）フェニル基、３－（２－ナフチル）フェニル基、４－（１－ナフチル）フェニル基、４－（２－ナフチル）フェニル基、３－（９－フェナントリル）フェニル基、４－（９－フェナントリル）フェニル基、３－（フルオランテン－３－イル）フェニル基、４－（フルオランテン－３－イル）フェニル基、３－（２－ピリジル）フェニル基、４－（２－ピリジル）フェニル基、３－（３－ピリジル）フェニル基、４－（３－ピリジル）フェニル基、３－（２－キノリル）フェニル基、４－（２－キノリル）フェニル基、３－（３－キノリル）フェニル基、４－（３－キノリル）フェニル基、３－（２－ベンゾチエニル）フェニル基、４－（２－ベンゾチエニル）フェニル基、３－（２－ベンゾフリル）フェニル基、４－（２－ベンゾフリル）フェニル基、３－（２－ジベンゾチエニル）フェニル基、４－（２－ジベンゾチエニル）フェニル基、３－（４－ジベンゾチエニル）フェニル基、４－（４－ジベンゾチエニル）フェニル基、３－（２－ジベンゾフリル）フェニル基、４－（２－ジベンゾフリル）フェニル基、３－（４－ジベンゾフリル）フェニル基、４－（４－ジベンゾフリル）フェニル基、１－ナフチル基、２－ナフチル基、９－フェナントリル基、２－ジベンゾチエニル基、２－ジベンゾフリル基、４－ジベンゾチエニル基、又は４－ジベンゾフリル基等がより好ましい。 -Ar 2 -Ar 3 -Ar 4 A group represented by the formula: 5 -Ar 6 -Ar 7 Specific examples of the group represented by the formula are not particularly limited, and examples thereof include a phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5 -Dimethylphenyl group, mesityl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3- Propylphenyl group, 4-propylphenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4- Diisopropylphenyl group, 3,5-diisopropylphenyl group, 2-butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2,4 Dibutylphenyl group, 3,5-dibutylphenyl group, 2-tert-butylphenyl group, 3-tert-butylphenyl group, 4-tert-butylphenyl group, 2,4-di-tert-butylphenyl group, 3, 5-di-tert-butylphenyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2'-methylbiphenyl-4-yl Group, 4'-methylbiphenyl-4-yl group, 2,2'-dimethylbiphenyl-4-yl group, 2 ', 4', 6'-trimethylbiphenyl-4-yl group, 6-methylbiphenyl-3- Yl group, 5-methylbiphenyl-3-yl group, 2'-methylbiphenyl-3-yl group, 4'-methylbiphenyl-3-yl group, 6,2'-dimethylbiphenyl-3-yl group 2 ′, 4 ′, 6′-trimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2′-methylbiphenyl-2-yl group, 4 ′ -Methylbiphenyl-2-yl group, 6,2'-dimethylbiphenyl-2-yl group, 2 ', 4', 6'-trimethylbiphenyl-2-yl group, 3-ethylbiphenyl-4-yl group, 4 '-Ethylbiphenyl-4-yl group, 2', 4 ', 6'-triethylbiphenyl-4-yl group, 6-ethylbiphenyl-3-yl group, 4'-ethylbiphenyl-3-yl group, 5- Ethylbiphenyl-2-yl group, 4′-ethylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-triethylbiphenyl-2-yl group, 3-propylbiphenyl-4-yl group, 4′-propyl Biphenyl-4-yl group, 2 ', 4', 6'-to Propylbiphenyl-4-yl group, 6-propylbiphenyl-3-yl group, 4′-propylbiphenyl-3-yl group, 5-propylbiphenyl-2-yl group, 4′-propylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-tripropylbiphenyl-2-yl group, 3-isopropylbiphenyl-4-yl group, 4′-isopropylbiphenyl-4-yl group, 2 ′, 4 ′, 6′-triisopropyl Biphenyl-4-yl group, 6-isopropylbiphenyl-3-yl group, 4′-isopropylbiphenyl-3-yl group, 5-isopropylbiphenyl-2-yl group, 4′-isopropylbiphenyl-2-yl group, 2 ', 4', 6'-triisopropylbiphenyl-2-yl group, 3-butylbiphenyl-4-yl group, 4'-butylbiphenyl-4-yl group, 2 ', 4', 6'-trib Tylbiphenyl-4-yl group, 6-butylbiphenyl-3-yl group, 4′-butylbiphenyl-3-yl group, 5-butylbiphenyl-2-yl group, 4′-butylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-tributylbiphenyl-2-yl group, 3-tert-butylbiphenyl-4-yl group, 4′-tert-butylbiphenyl-4-yl group, 2 ′, 4 ′, 6 ′ -Tri-tert-butylbiphenyl-4-yl group, 6-tert-butylbiphenyl-3-yl group, 4'-tert-butylbiphenyl-3-yl group, 5-tert-butylbiphenyl-2-yl group, 4 '-Tert-butylbiphenyl-2-yl group, 2', 4 ', 6'-tri-tert-butylbiphenyl-2-yl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methyl Pyridine-3 Yl group, 2-methylpyridin-4-yl group, 2-methylpyridin-5-yl group, 2-methylpyridin-6-yl group, 3-methylpyridin-2-yl group, 3-methylpyridin-4- Yl group, 3-methylpyridin-5-yl group, 3-methylpyridin-6-yl group, 4-methylpyridin-2-yl group, 4-methylpyridin-3-yl group, 2,6-dimethylpyridine- 3-yl group, 2,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridin-2-yl group, 3,6-dimethylpyridin-4-yl group, 3,6-dimethylpyridine-5- Yl group, 2-phenylpyridin-6-yl group, 3-phenylpyridin-6-yl group, 4-phenylpyridin-6-yl group, 5-phenylpyridin-6-yl group, 2-phenylpyridin-3- Iru group, 2-pheny Rupyridin-5-yl group, 3-phenylpyridin-5-yl group, 4-phenylpyridin-3-yl group, 3-phenylpyridin-4-yl group, 2-phenylpyridin-4-yl group,
2- (2-pyridyl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 2- (3-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 2- (4-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 2- (3-methyl-2-pyridyl) ) Phenyl group, 3- (3-methyl-2-pyridyl) phenyl group, 4- (3-methyl-2-pyridyl) phenyl group, 2- (4-methyl-2-pyridyl) phenyl group, 3- (4 -Methyl-2-pyridyl) phenyl group, 4- (4-methyl-2-pyridyl) phenyl group, 2- (5-methyl-2-pyridyl) phenyl group, 3- (5-methyl-2-pyridyl) phenyl The group 4- (5-methyl-2-pyri L) phenyl group, 2- (6-methyl-2-pyridyl) phenyl group, 3- (6-methyl-2-pyridyl) phenyl group, 4- (6-methyl-2-pyridyl) phenyl group, 2- ( 2-methyl-3-pyridyl) phenyl group, 3- (2-methyl-3-pyridyl) phenyl group, 4- (2-methyl-3-pyridyl) phenyl group, 2- (4-methyl-3-pyridyl) Phenyl group, 3- (4-methyl-3-pyridyl) phenyl group, 4- (4-methyl-3-pyridyl) phenyl group, 2- (5-methyl-3-pyridyl) phenyl group, 3- (5- Methyl-3-pyridyl) phenyl group, 4- (5-methyl-3-pyridyl) phenyl group, 2- (6-methyl-3-pyridyl) phenyl group, 3- (6-methyl-3-pyridyl) phenyl group , 4- (6-Methyl-3-pyridyl) Enyl group, 2- (2-methyl-4-pyridyl) phenyl group, 3- (2-methyl-4-pyridyl) phenyl group, 4- (2-methyl-4-pyridyl) phenyl group, 2- (3- Methyl-4-pyridyl) phenyl group, 3- (3-methyl-4-pyridyl) phenyl group, 4- (3-methyl-4-pyridyl) phenyl group, 2- (2,4-dimethyl-3-pyridyl) Phenyl group, 3- (2,4-dimethyl-3-pyridyl) phenyl group, 4- (2,4-dimethyl-3-pyridyl) phenyl group, 2- (3,5-dimethyl-4-pyridyl) phenyl group 3- (3,5-dimethyl-4-pyridyl) phenyl group, 4- (3,5-dimethyl-4-pyridyl) phenyl group, 2- (3-phenyl-2-pyridyl) phenyl group, 3- ( 3-phenyl-2-pyridyl) phenyl group, 4- (3-phenyl-2-pyridyl) phenyl group, 2- (4-phenyl-2-pyridyl) phenyl group, 3- (4-phenyl-2-pyridyl) phenyl group, 4- (4-phenyl-2) -Pyridyl) phenyl group, 2- (5-phenyl-2-pyridyl) phenyl group, 3- (5-phenyl-2-pyridyl) phenyl group, 4- (5-phenyl-2-pyridyl) phenyl group, 2- (6-phenyl-2-pyridyl) phenyl group, 3- (6-phenyl-2-pyridyl) phenyl group, 4- (6-phenyl-2-pyridyl) phenyl group, 2- (2-phenyl-3-pyridyl) ) Phenyl group, 3- (2-phenyl-3-pyridyl) phenyl group, 4- (2-phenyl-3-pyridyl) phenyl group, 2- (4-phenyl-3-pyridyl) phenyl group, 3- (4 -Phenyl-3 Pyridyl) phenyl group, 4- (4-phenyl-3-pyridyl) phenyl group, 2- (5-phenyl-3-pyridyl) phenyl group, 3- (5-phenyl-3-pyridyl) phenyl group, 4- ( 5-phenyl-3-pyridyl) phenyl group, 2- (6-phenyl-3-pyridyl) phenyl group, 3- (6-phenyl-3-pyridyl) phenyl group, 4- (6-phenyl-3-pyridyl) Phenyl group, 2- (2-phenyl-4-pyridyl) phenyl group, 3- (2-phenyl-4-pyridyl) phenyl group, 4- (2-phenyl-4-pyridyl) phenyl group, 2- (3- Phenyl-4-pyridyl) phenyl group, 3- (3-phenyl-4-pyridyl) phenyl group, 4- (3-phenyl-4-pyridyl) phenyl group, 2- (2,4-diphenyl-3-pyridyl) Fe Group, 3- (2,4-diphenyl-3-pyridyl) phenyl group, 4- (2,4-diphenyl-3-pyridyl) phenyl group, 2- (3,5-diphenyl-4-pyridyl) phenyl group 3- (3,5-diphenyl-4-pyridyl) phenyl group, 4- (3,5-diphenyl-4-pyridyl) phenyl group,
2- (1-naphthyl) phenyl group, 3- (1-naphthyl) phenyl group, 4- (1-naphthyl) phenyl group, 2- (2-naphthyl) phenyl group, 3- (2-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 2- (1-phenanthryl) phenyl group, 3- (1-phenanthryl) phenyl group, 4- (1-phenanthryl) phenyl group, 2- (2-phenanthryl) phenyl group, 3- (2-phenanthryl) phenyl group, 4- (2-phenanthryl) phenyl group, 2- (3-phenanthryl) phenyl group, 3- (3-phenanthryl) phenyl group, 4- (3-phenanthryl) phenyl group, 2- (4-phenanthryl) phenyl group, 3- (4-phenanthryl) phenyl group, 4- (4-phenanthryl) phenyl group, 2- (9-phenane) Ryl) phenyl group, 3- (9-phenanthryl) phenyl group, 4- (9-phenanthryl) phenyl group, 2- (1-anthryl) phenyl group, 3- (1-anthryl) phenyl group, 4- (1- Anthryl) phenyl group, 2- (2-anthryl) phenyl group, 3- (2-anthryl) phenyl group, 4- (2-anthryl) phenyl group, 2- (9-anthryl) phenyl group, 3- (9- Anthryl) phenyl group, 4- (9-anthryl) phenyl group, 2- (1-pyrenyl) phenyl group, 3- (1-pyrenyl) phenyl group, 4- (1-pyrenyl) phenyl group, 2- (2- Pyrenyl) phenyl group, 3- (2-pyrenyl) phenyl group, 4- (2-pyrenyl) phenyl group, 2- (4-pyrenyl) phenyl group, 3- (4-pyrenyl) phenyl group, 4- (4 Pyrenyl) phenyl group, 2- (fluoranthen-1-yl) phenyl group, 3- (fluoranthen-1-yl) phenyl group, 4- (fluoranthen-1-yl) phenyl group, 2- (fluoranthen-2-yl) Phenyl group, 3- (fluoranthen-2-yl) phenyl group, 4- (fluoranthen-2-yl) phenyl group, 2- (fluoranthen-3-yl) phenyl group, 3- (fluoranthen-3-yl) phenyl group 4- (fluoranthen-3-yl) phenyl group, 2- (fluoranthen-4-yl) phenyl group, 3- (fluoranthen-4-yl) phenyl group, 4- (fluoranthen-4-yl) phenyl group, 2 -(Fluoranthen-5-yl) phenyl group, 3- (fluoranthen-5-yl) phenyl group, 4- (fluoranthen-5-yl) L) phenyl group, 2- (triphenylene-1-yl) phenyl group, 3- (triphenylene-1-yl) phenyl group, 4- (triphenylene-1-yl) phenyl group, 2- (triphenylene-2-yl) Phenyl group, 3- (triphenylene-2-yl) phenyl group, 4- (triphenylene-2-yl) phenyl group, 2- (chrysen-1-yl) phenyl group, 3- (chrysen-1-yl) phenyl group 4- (chrysen-1-yl) phenyl group, 2- (chrysen-2-yl) phenyl group, 3- (chrysen-2-yl) phenyl group, 4- (chrysen-2-yl) phenyl group, 2 -(Chrysen-3-yl) phenyl group, 3- (Chrysen-3-yl) phenyl group, 4- (Chrysen-3-yl) phenyl group, 2- (Chrysen-4-yl) phenyl group, 3- ( Lysene-4-yl) phenyl group, 4- (chrysen-4-yl) phenyl group, 2- (chrysen-5-yl) phenyl group, 3- (chrysen-5-yl) phenyl group, 4- (chrysene- 5-yl) phenyl group, 2- (chrysen-6-yl) phenyl group, 3- (chrysen-6-yl) phenyl group, 4- (chrysen-6-yl) phenyl group, 2- (acenaphthylene-1- Yl) phenyl group, 3- (acenaphthylene-1-yl) phenyl group, 4- (acenaphthylene-1-yl) phenyl group, 2- (acenaphthylene-3-yl) phenyl group, 3- (acenaphthylene-3-yl) Phenyl group, 4- (acenaphthylene-3-yl) phenyl group, 2- (acenaphthylene-4-yl) phenyl group, 3- (acenaphthylene-4-yl) phenyl group, 4- (acenaphthyl) Down-4-yl) phenyl group, 2- (acenaphthylene-5-yl) phenyl group, 3- (acenaphthylene-5-yl) phenyl group, 4- (acenaphthylene-5-yl) phenyl group,
2- (fluoren-1-yl) phenyl group, 3- (fluoren-1-yl) phenyl group, 4- (fluoren-1-yl) phenyl group, 2- (fluoren-2-yl) phenyl group, 3- (Fluoren-2-yl) phenyl group, 4- (fluoren-2-yl) phenyl group, 2- (fluoren-3-yl) phenyl group, 3- (fluoren-3-yl) phenyl group, 4- (fluorene -3-yl) phenyl group, 2- (fluoren-4-yl) phenyl group, 3- (fluoren-4-yl) phenyl group, 4- (fluoren-4-yl) phenyl group, 2- (pyrimidine-2 -Yl) phenyl group, 3- (pyrimidin-2-yl) phenyl group, 4- (pyrimidin-2-yl) phenyl group, 2- (pyrimidin-4-yl) phenyl group, 3- (pyrimidin-4-yl) Phenyl group, 4- (pyrimidin-4-yl) phenyl group, 2- (pyrimidin-5-yl) phenyl group, 3- (pyrimidin-5-yl) phenyl group, 4- (pyrimidin-5-yl) phenyl group 2- (2-quinolyl) phenyl group, 3- (2-quinolyl) phenyl group, 4- (2-quinolyl) phenyl group, 2- (3-quinolyl) phenyl group, 3- (3-quinolyl) phenyl group 4- (3-quinolyl) phenyl group, 2- (4-quinolyl) phenyl group, 3- (4-quinolyl) phenyl group, 4- (4-quinolyl) phenyl group, 2- (5-quinolyl) phenyl group 3- (5-quinolyl) phenyl group, 4- (5-quinolyl) phenyl group, 2- (6-quinolyl) phenyl group, 3- (6-quinolyl) phenyl group, 4- (6-quinolyl) phenyl group , 2- (7-key Ryl) phenyl group, 3- (7-quinolyl) phenyl group, 4- (7-quinolyl) phenyl group, 2- (8-quinolyl) phenyl group, 3- (8-quinolyl) phenyl group, 4- (8- Quinolyl) phenyl group, 2- (2-isoquinolyl) phenyl group, 3- (2-isoquinolyl) phenyl group, 4- (2-isoquinolyl) phenyl group, 2- (3-isoquinolyl) phenyl group, 3- (3- Isoquinolyl) phenyl group, 4- (3-isoquinolyl) phenyl group, 2- (4-isoquinolyl) phenyl group, 3- (4-isoquinolyl) phenyl group, 4- (4-isoquinolyl) phenyl group, 2- (5- Isoquinolyl) phenyl group, 3- (5-isoquinolyl) phenyl group, 4- (5-isoquinolyl) phenyl group, 2- (6-isoquinolyl) phenyl group, 3- (6-isoquinolyl) L) phenyl group, 4- (6-isoquinolyl) phenyl group, 2- (7-isoquinolyl) phenyl group, 3- (7-isoquinolyl) phenyl group, 4- (7-isoquinolyl) phenyl group, 2- (8- Isoquinolyl) phenyl group, 3- (8-isoquinolyl) phenyl group, 4- (8-isoquinolyl) phenyl group, 2- (phenanthridin-2-yl) phenyl group, 3- (phenanthridin-2-yl) Phenyl group, 4- (phenanthridin-2-yl) phenyl group, 2- (phenanthridin-3-yl) phenyl group, 3- (phenanthridin-3-yl) phenyl group, 4- (phenanthate) Lysine-3-yl) phenyl group, 2- (phenanthridin-4-yl) phenyl group, 3- (phenanthridin-4-yl) phenyl group, 4- (phenanthridin-4-yl) ) Phenyl group, 2- (phenanthridin-5-yl) phenyl group, 3- (phenanthridin-5-yl) phenyl group, 4- (phenanthridin-5-yl) phenyl group, 2- (phenanthridin-5-yl) phenyl group, Nanthridin-6-yl) phenyl group, 3- (phenanthridin-6-yl) phenyl group, 4- (phenanthridin-6-yl) phenyl group, 2- (phenanthridin-7-yl) phenyl Group, 3- (phenanthridin-7-yl) phenyl group, 4- (phenanthridin-7-yl) phenyl group, 2- (phenanthridin-8-yl) phenyl group, 3- (phenanthridine -8-yl) phenyl group, 4- (phenanthridin-8-yl) phenyl group, 2- (phenanthridin-9-yl) phenyl group, 3- (phenanthridin-9-yl) phenyl group, 4- ( Enanthridin-9-yl) phenyl group, 2- (phenanthridin-10-yl) phenyl group, 3- (phenanthridin-10-yl) phenyl group, 4- (phenanthridin-10-yl) phenyl group ,
2- (benzo [h] quinolin-2-yl) phenyl group, 3- (benzo [h] quinolin-2-yl) phenyl group, 4- (benzo [h] quinolin-2-yl) phenyl group, 2- (Benzo [h] quinolin-3-yl) phenyl group, 3- (benzo [h] quinolin-3-yl) phenyl group, 4- (benzo [h] quinolin-3-yl) phenyl group, 2- (benzo [H] quinolin-4-yl) phenyl group, 3- (benzo [h] quinolin-4-yl) phenyl group, 4- (benzo [h] quinolin-4-yl) phenyl group, 2- (benzo [h ] Quinolin-5-yl) phenyl group, 3- (benzo [h] quinolin-5-yl) phenyl group, 4- (benzo [h] quinolin-5-yl) phenyl group, 2- (benzo [h] quinoline) -6-yl) phenyl group, 3- (benzo [h Quinolin-6-yl) phenyl group, 4- (benzo [h] quinolin-6-yl) phenyl group, 2- (benzo [h] quinolin-7-yl) phenyl group, 3- (benzo [h] quinoline- 7-yl) phenyl group, 4- (benzo [h] quinolin-7-yl) phenyl group, 2- (benzo [h] quinolin-8-yl) phenyl group, 3- (benzo [h] quinoline-8- Yl) phenyl group, 4- (benzo [h] quinolin-8-yl) phenyl group, 2- (benzo [h] quinolin-9-yl) phenyl group, 3- (benzo [h] quinolin-9-yl) Phenyl group, 4- (benzo [h] quinolin-9-yl) phenyl group, 2- (benzo [h] quinolin-10-yl) phenyl group, 3- (benzo [h] quinolin-10-yl) phenyl group , 4- (Benzo [h] quinoline- 0-yl) phenyl group, 2- (acridin-1-yl) phenyl group, 3- (acridin-1-yl) phenyl group, 4- (acridin-1-yl) phenyl group, 2- (acridin-2- Yl) phenyl group, 3- (acridin-2-yl) phenyl group, 4- (acridin-2-yl) phenyl group, 2- (acridin-3-yl) phenyl group, 3- (acridin-3-yl) Phenyl group, 4- (acridin-3-yl) phenyl group, 2- (acridin-4-yl) phenyl group, 3- (acridin-4-yl) phenyl group, 4- (acridin-4-yl) phenyl group 2- (acridin-9-yl) phenyl group, 3- (acridin-9-yl) phenyl group, 4- (acridin-9-yl) phenyl group, 2- (2-thienyl) phenyl group, 3- ( 2-chi Enyl) phenyl group, 4- (2-thienyl) phenyl group, 2- (3-thienyl) phenyl group, 3- (3-thienyl) phenyl group, 4- (3-thienyl) phenyl group, 2- (3- Methylthiophen-2-yl) phenyl group, 3- (3-methylthiophen-2-yl) phenyl group, 4- (3-methylthiophen-2-yl) phenyl group, 2- (4-methylthiophen-2- Yl) phenyl group, 3- (4-methylthiophen-2-yl) phenyl group, 4- (4-methylthiophen-2-yl) phenyl group, 2- (5-methylthiophen-2-yl) phenyl group, 3- (5-methylthiophen-2-yl) phenyl group, 4- (5-methylthiophen-2-yl) phenyl group, 2- (2-methylthiophen-3-yl) phenyl group, 3- (2- Methylthi Phen-3-yl) phenyl group, 4- (2-methylthiophen-3-yl) phenyl group, 2- (4-methylthiophen-3-yl) phenyl group, 3- (4-methylthiophen-3-yl) ) Phenyl group, 4- (4-methylthiophen-3-yl) phenyl group, 2- (5-methylthiophen-3-yl) phenyl group, 3- (5-methylthiophen-3-yl) phenyl group, 4 -(5-methylthiophen-3-yl) phenyl group, 2- (3-phenylthiophen-2-yl) phenyl group, 3- (3-phenylthiophen-2-yl) phenyl group, 4- (3-phenyl) Thiophen-2-yl) phenyl group, 2- (4-phenylthiophen-2-yl) phenyl group, 3- (4-phenylthiophen-2-yl) phenyl group, 4- (4-phenylthiooff) N-2-yl) phenyl group, 2- (5-phenylthiophen-2-yl) phenyl group, 3- (5-phenylthiophen-2-yl) phenyl group, 4- (5-phenylthiophen-2-yl) ) Phenyl group, 2- (2-phenylthiophen-3-yl) phenyl group, 3- (2-phenylthiophen-3-yl) phenyl group, 4- (2-phenylthiophen-3-yl) phenyl group, 2 -(4-phenylthiophen-3-yl) phenyl group, 3- (4-phenylthiophen-3-yl) phenyl group, 4- (4-phenylthiophen-3-yl) phenyl group, 2- (5-phenyl) Thiophen-3-yl) phenyl group, 3- (5-phenylthiophen-3-yl) phenyl group, 4- (5-phenylthiophen-3-yl) phenyl group,
3- (2-furyl) phenyl group, 4- (2-furyl) phenyl group, 2- (3-furyl) phenyl group, 3- (3-furyl) phenyl group, 4- (3-furyl) phenyl group, 2- (3-methylfuran-2-yl) phenyl group, 3- (3-methylfuran-2-yl) phenyl group, 4- (3-methylfuran-2-yl) phenyl group, 2- (4- Methylfuran-2-yl) phenyl group, 3- (4-methylfuran-2-yl) phenyl group, 4- (4-methylfuran-2-yl) phenyl group, 2- (5-methylfuran-2- Yl) phenyl group, 3- (5-methylfuran-2-yl) phenyl group, 4- (5-methylfuran-2-yl) phenyl group, 2- (2-methylfuran-3-yl) phenyl group, 3- (2-methylfuran-3-yl) phenyl group, 4- (2- Tilfuran-3-yl) phenyl group, 2- (4-methylfuran-3-yl) phenyl group, 3- (4-methylfuran-3-yl) phenyl group, 4- (4-methylfuran-3-yl) ) Phenyl group, 2- (5-methylfuran-3-yl) phenyl group, 3- (5-methylfuran-3-yl) phenyl group, 4- (5-methylfuran-3-yl) phenyl group, 2 -(3-phenylfuran-2-yl) phenyl group, 3- (3-phenylfuran-2-yl) phenyl group, 4- (3-phenylfuran-2-yl) phenyl group, 2- (4-phenyl) Furan-2-yl) phenyl group, 3- (4-phenylfuran-2-yl) phenyl group, 4- (4-phenylfuran-2-yl) phenyl group, 2- (5-phenylfuran-2-yl) ) Phenyl group, 3- (5-phenyl) Lan-2-yl) phenyl group, 4- (5-phenylfuran-2-yl) phenyl group, 2- (2-phenylfuran-3-yl) phenyl group, 3- (2-phenylfuran-3-yl) ) Phenyl group, 4- (2-phenylfuran-3-yl) phenyl group, 2- (4-phenylfuran-3-yl) phenyl group, 3- (4-phenylfuran-3-yl) phenyl group, 4 -(4-phenylfuran-3-yl) phenyl group, 2- (5-phenylfuran-3-yl) phenyl group, 3- (5-phenylfuran-3-yl) phenyl group, 4- (5-phenyl) Furan-3-yl) phenyl group, 2- (2-benzo [b] thienyl) phenyl group, 3- (2-benzo [b] thienyl) phenyl group, 4- (2-benzo [b] thienyl) phenyl group , 2- (3-Benzo [b] thie Nyl) phenyl group, 3- (3-benzo [b] thienyl) phenyl group, 4- (3-benzo [b] thienyl) phenyl group, 2- (4-benzo [b] thienyl) phenyl group, 3- ( 4-benzo [b] thienyl) phenyl group, 4- (4-benzo [b] thienyl) phenyl group, 2- (5-benzo [b] thienyl) phenyl group, 3- (5-benzo [b] thienyl) Phenyl group, 4- (5-benzo [b] thienyl) phenyl group, 2- (6-benzo [b] thienyl) phenyl group, 3- (6-benzo [b] thienyl) phenyl group, 4- (6- Benzo [b] thienyl) phenyl group, 2- (7-benzo [b] thienyl) phenyl group, 3- (7-benzo [b] thienyl) phenyl group, 4- (7-benzo [b] thienyl) phenyl group , 2- (2-Benzo [b] furyl) fur Nyl group, 3- (2-benzo [b] furyl) phenyl group, 4- (2-benzo [b] furyl) phenyl group, 2- (3-benzo [b] furyl) phenyl group, 3- (3- Benzo [b] furyl) phenyl group, 4- (3-benzo [b] furyl) phenyl group, 2- (4-benzo [b] furyl) phenyl group, 3- (4-benzo [b] furyl) phenyl group 4- (4-benzo [b] furyl) phenyl group, 2- (5-benzo [b] furyl) phenyl group, 3- (5-benzo [b] furyl) phenyl group, 4- (5-benzo [ b] furyl) phenyl group, 2- (6-benzo [b] furyl) phenyl group, 3- (6-benzo [b] furyl) phenyl group, 4- (6-benzo [b] furyl) phenyl group, 2 -(7-benzo [b] furyl) phenyl group, 3- (7-benzo [b] furyl ) Phenyl group, 4- (7-benzo [b] furyl) phenyl group, 2- (1-dibenzothienyl) phenyl group, 3- (1-dibenzothienyl) phenyl group, 4- (1-dibenzothienyl) phenyl group 2- (2-dibenzothienyl) phenyl group, 3- (2-dibenzothienyl) phenyl group, 4- (2-dibenzothienyl) phenyl group, 2- (3-dibenzothienyl) phenyl group, 3- (3- Dibenzothienyl) phenyl group, 4- (3-dibenzothienyl) phenyl group, 2- (4-dibenzothienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4- (4-dibenzothienyl) phenyl group, 2- (1-dibenzofuryl) phenyl group, 3- (1-dibenzofuryl) phenyl group, 4- (1-dibenzofuryl) phenyl group, 2- (2-diben) Zofuryl) phenyl group, 3- (2-dibenzofuryl) phenyl group, 4- (2-dibenzofuryl) phenyl group, 2- (3-dibenzofuryl) phenyl group, 3- (3-dibenzofuryl) phenyl group, 4 -(3-dibenzofuryl) phenyl group, 2- (4-dibenzofuryl) phenyl group, 3- (4-dibenzofuryl) phenyl group, 4- (4-dibenzofuryl) phenyl group,
3- (2-pyridyl) biphenyl-4-yl group, 2 ′-(2-pyridyl) biphenyl-4-yl group, 4 ′-(2-pyridyl) biphenyl-4-yl group, 2,2′-di group (2-pyridyl) biphenyl-4-yl group, 2 ′, 4 ′, 6′-tri (2-pyridyl) biphenyl-4-yl group, 6- (2-pyridyl) biphenyl-3-yl group, 5- (2-pyridyl) biphenyl-3-yl group, 2 ′-(2-pyridyl) biphenyl-3-yl group, 4 ′-(2-pyridyl) biphenyl-3-yl group, 6,2′-di (2 -Pyridyl) biphenyl-3-yl group, 5- (2-pyridyl) biphenyl-2-yl group, 6- (2-pyridyl) biphenyl-2-yl group, 2 '-(2-pyridyl) biphenyl-2- Yl group, 4 ′-(2-pyridyl) biphenyl-2-yl group, 6,2′-di (2-pi Di) biphenyl-2-yl group, 3- (3-pyridyl) biphenyl-4-yl group, 2 '-(3-pyridyl) biphenyl-4-yl group, 4'-(3-pyridyl) biphenyl-4- Yl group, 2,2′-di (3-pyridyl) biphenyl-4-yl group, 2 ′, 4 ′, 6′-tri (3-pyridyl) biphenyl-4-yl group, 6- (3-pyridyl) Biphenyl-3-yl group, 5- (3-pyridyl) biphenyl-3-yl group, 2 '-(3-pyridyl) biphenyl-3-yl group, 4'-(3-pyridyl) biphenyl-3-yl group 6,2'-di (3-pyridyl) biphenyl-3-yl group, 5- (3-pyridyl) biphenyl-2-yl group, 6- (3-pyridyl) biphenyl-2-yl group, 2'- (3-pyridyl) biphenyl-2-yl group, 4 ′-(3-pyridyl) biphenyl- 2-yl group, 6,2′-di (3-pyridyl) biphenyl-2-yl group, 3- (4-pyridyl) biphenyl-4-yl group, 2 ′-(4-pyridyl) biphenyl-4-yl Group, 4 ′-(4-pyridyl) biphenyl-4-yl group, 2,2′-di (4-pyridyl) biphenyl-4-yl group, 2 ′, 4 ′, 6′-tri (4-pyridyl) Biphenyl-4-yl group, 6- (4-pyridyl) biphenyl-3-yl group, 5- (4-pyridyl) biphenyl-3-yl group, 2 ′-(4-pyridyl) biphenyl-3-yl group, 4 ′-(4-pyridyl) biphenyl-3-yl group, 6,2′-di (4-pyridyl) biphenyl-3-yl group, 5- (4-pyridyl) biphenyl-2-yl group, 6- ( 4-pyridyl) biphenyl-2-yl group, 2 ′-(4-pyridyl) biphenyl-2-yl group, '-(4-pyridyl) biphenyl-2-yl group, 6,2'-di (4-pyridyl) biphenyl-2-yl group, 3- (1-naphthyl) biphenyl-4-yl group, 2'-( 1-naphthyl) biphenyl-4-yl group, 4 ′-(1-naphthyl) biphenyl-4-yl group, 2,2′-di (1-naphthyl) biphenyl-4-yl group, 2 ′, 4 ′, 6′-tri (1-naphthyl) biphenyl-4-yl group, 6- (1-naphthyl) biphenyl-3-yl group, 5- (1-naphthyl) biphenyl-3-yl group, 2 ′-(1- Naphthyl) biphenyl-3-yl group, 4 ′-(1-naphthyl) biphenyl-3-yl group, 6,2′-di (1-naphthyl) biphenyl-3-yl group, 5- (1-naphthyl) biphenyl -2-yl, 6- (1-naphthyl) biphenyl-2-yl, 2 ′-(1-naphth Til) biphenyl-2-yl group, 4 ′-(1-naphthyl) biphenyl-2-yl group, 6,2′-di (1-naphthyl) biphenyl-2-yl group, 3- (2-naphthyl) biphenyl -4-yl group, 2 ′-(2-naphthyl) biphenyl-4-yl group, 4 ′-(2-naphthyl) biphenyl-4-yl group, 2,2′-di (2-naphthyl) biphenyl-4 -Yl group, 2 ', 4', 6'-tri (2-naphthyl) biphenyl-4-yl group, 6- (2-naphthyl) biphenyl-3-yl group, 5- (2-naphthyl) biphenyl-3 -Yl group, 2 '-(2-naphthyl) biphenyl-3-yl group, 4'-(2-naphthyl) biphenyl-3-yl group, 6,2'-di (2-naphthyl) biphenyl-3-yl Group, 5- (2-naphthyl) biphenyl-2-yl group, 6- (2-naphthyl) biphe Ru-2-yl group, 2 '-(2-naphthyl) biphenyl-2-yl group, 4'-(2-naphthyl) biphenyl-2-yl group, 6,2'-di (2-naphthyl) biphenyl- 2-yl group,
1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalen-4-yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl group, 1-phenylnaphthalen-7-yl group, 1-phenylnaphthalen-8-yl group, 2-phenylnaphthalen-1-yl group, 2-phenylnaphthalen-3-yl group, 2-phenylnaphthalen-4-yl group, 2-phenylnaphthalen-5-yl group, 2-phenylnaphthalen-6-yl group, 2-phenylnaphthalen-7-yl group, 2-phenylnaphthalen-8-yl group, 1-methylnaphthalen-4-yl group, 1-methylnaphthalen-5-yl group, 1-methylnaphthalen-6-yl group, 1-methylnaphthalene-7-y Group, 1-methylnaphthalen-8-yl group, 2-methylnaphthalen-1-yl group, 2-methylnaphthalen-3-yl group, 2-methylnaphthalen-4-yl group, 2-methylnaphthalen-5-yl group Group, 2-methylnaphthalen-6-yl group, 2-methylnaphthalen-7-yl group, 2-methylnaphthalen-8-yl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group Group, 9-phenanthryl group, 1-phenylphenanthren-2-yl group, 1-phenylphenanthren-3-yl group, 1-phenylphenanthren-4-yl group, 1-phenylphenanthren-5-yl group, 1-phenyl Phenanthren-6-yl group, 1-phenylphenanthren-7-yl group, 1-phenylphenanthren-8-yl group 1-phenylphenanthren-9-yl group, 1-phenylphenanthren-10-yl group, 2-phenylphenanthren-1-yl group, 2-phenylphenanthren-3-yl group, 2-phenylphenanthren-4-yl group, 2-phenylphenanthren-5-yl group, 2-phenylphenanthren-6-yl group, 2-phenylphenanthren-7-yl group, 2-phenylphenanthren-8-yl group, 2-phenylphenanthren-9-yl group, 2-phenylphenanthren-10-yl group, 3-phenylphenanthren-1-yl group, 3-phenylphenanthren-2-yl group, 3-phenylphenanthren-4-yl group, 3-phenylphenanthren-5-yl group, 3-phenylphenanthren-6-yl group, 3-phenylphenanthate Len-7-yl group, 3-phenylphenanthren-8-yl group, 3-phenylphenanthren-9-yl group, 3-phenylphenanthren-10-yl group, 4-phenylphenanthren-1-yl group, 4-phenyl Phenanthren-2-yl group, 4-phenylphenanthren-3-yl group, 4-phenylphenanthren-5-yl group, 4-phenylphenanthren-6-yl group, 4-phenylphenanthren-7-yl group, 4-phenyl Phenanthren-8-yl group, 4-phenylphenanthren-9-yl group, 4-phenylphenanthren-10-yl group, 1-methylphenanthren-2-yl group, 1-methylphenanthren-3-yl group, 1-methyl Phenanthren-4-yl group, 1-methylphenanthren-5-yl group, 1-methyl group Nanthren-6-yl group, 1-methylphenanthren-7-yl group, 1-methylphenanthren-8-yl group, 1-methylphenanthren-9-yl group, 1-methylphenanthren-10-yl group, 2-methyl Phenanthren-1-yl group, 2-methylphenanthren-3-yl group, 2-methylphenanthren-4-yl group, 2-methylphenanthren-5-yl group, 2-methylphenanthren-6-yl group, 2-methyl Phenanthren-7-yl group, 2-methylphenanthren-8-yl group, 2-methylphenanthren-9-yl group, 2-methylphenanthren-10-yl group, 3-methylphenanthren-1-yl group, 3-methyl Phenanthren-2-yl group, 3-methylphenanthren-4-yl group, 3-methylphenanthrene-5 Yl group, 3-methylphenanthrene-6-yl group, 3-methylphenanthrene-7-yl group, 3-methylphenanthrene-8-yl group, 3-methylphenanthren-9-yl group, 3-methylphenanthrene-10- Yl group, 4-methylphenanthren-1-yl group, 4-methylphenanthren-2-yl group, 4-methylphenanthren-3-yl group, 4-methylphenanthren-5-yl group, 4-methylphenanthrene-6- Yl group, 4-methylphenanthren-7-yl group, 4-methylphenanthrene-8-yl group, 4-methylphenanthrene-9-yl group, 4-methylphenanthren-10-yl group,
1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenylanthracen-2-yl group, 1-phenylanthracen-3-yl group, 1-phenylanthracen-4-yl group, 1-phenylanthracene- 5-yl group, 1-phenylanthracen-6-yl group, 1-phenylanthracen-7-yl group, 1-phenylanthracen-8-yl group, 1-phenylanthracen-9-yl group, 1-phenylanthracene- 10-yl group, 2-phenylanthracen-1-yl group, 2-phenylanthracen-3-yl group, 2-phenylanthracen-4-yl group, 2-phenylanthracen-5-yl group, 2-phenylanthracene- 6-yl group, 2-phenylanthracen-7-yl group, 2-phenylanthracen-8-yl group, 2 Phenylanthracen-9-yl group, 2-phenylanthracen-10-yl group, 9-phenylanthracen-1-yl group, 9-phenylanthracen-2-yl group, 9-phenylanthracen-3-yl group, 9- Phenylanthracen-4-yl group, 9-phenylanthracen-5-yl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-phenylpyren-2-yl group, 1-phenylpyrene-3- Yl group, 1-phenylpyren-4-yl group, 1-phenylpyren-5-yl group, 1-phenylpyren-6-yl group, 1-phenylpyren-7-yl group, 1-phenylpyrene-8- Yl group, 1-phenylpyren-9-yl group, 1-phenylpyren-10-yl group, 2-phenylpyren-1-yl group, 2-phenylpyren-3-yl group 2-phenylpyren-4-yl group, 2-phenylpyren-5-yl group, 2-phenylpyren-6-yl group, 2-phenylpyren-7-yl group, 2-phenylpyren-8-yl group, 2-phenylpyren-9-yl group, 2-phenylpyren-10-yl group, 9-phenylpyren-1-yl group, 9-phenylpyren-2-yl group, 9-phenylpyren-3-yl group, 9-phenylpyren-4-yl group, 9-phenylpyren-5-yl group, 9-phenylpyren-6-yl group, 9-phenylpyren-7-yl group, 9-phenylpyren-8-yl group, 9-phenylpyren-10-yl group, 1-methylpyren-2-yl group, 1-methylpyren-3-yl group, 1-methylpyren-4-yl group, 1-methylpyren-5-yl group, 1-methylpyrene- 6-yl group, 1-methylpyren-7-yl group, 1-methylpyren-8-yl group, 1-methylpyren-9-yl group, 1-methylpyren-10-yl group, 2-methylpyren-1-yl group, 2-methylpyrene-3 -Yl group, 2-methylpyren-4-yl group, 2-methylpyren-5-yl group, 2-methylpyren-6-yl group, 2-methylpyren-7-yl group, 2-methylpyren-8-yl group, 2 -Methylpyren-9-yl group, 2-methylpyren-10-yl group, 9-methylpyren-1-yl group, 9-methylpyren-2-yl group, 9-methylpyren-3-yl group, 9-methylpyrene-4- Yl group, 9-methylpyren-5-yl group, 9-methylpyren-6-yl group, 9-methylpyren-7-yl group, 9-methylpyren-8-yl group, 9-methylpyren-10-yl group, Fluoranthen-1-yl group, fluoranthen-1-yl group, fluoranthen-2-yl group, fluoranthen-3-yl group, fluoranthen-4-yl group, fluoranthen-5-yl group, fluoranthen-6-yl group, fluoranthene -7-yl group, fluoranthen-8-yl group, fluoranthen-9-yl group, fluoranthen-10-yl group, triphenylene-1-yl group, triphenylene-2-yl group, acenaphthylene-1-yl group, acenaphthylene- 3-yl group, acenaphthylene-4-yl group, acenaphthylene-5-yl group, chrysen-1-yl group, chrysen-2-yl group, chrysen-5-yl group, chrysen-6-yl group, 2-quinolyl Group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8- Noryl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, quinoxalin-2-yl group, quinoxalin-5-yl Group, quinoxalin-6-yl group, quinazolin-2-yl group, quinazolin-4-yl group, quinazolin-5-yl group, quinazolin-6-yl group, quinazolin-7-yl group, quinazolin-8-yl group , Pyrazin-2-yl group, pyrimidin-2-yl group, pyrimidin-4-yl group, pyrimidin-5-yl group, acridine-1-yl group, acridine-1-yl group, acridine-2-yl group, An acridine-3-yl group, an acridine-4-yl group, an acridine-9-yl group,
Phenanthridin-1-yl group, phenanthridin-1-yl group, phenanthridin-2-yl group, phenanthridin-3-yl group, phenanthridin-4-yl group, phenanthridin-6 -Yl group, phenanthridin-7-yl group, phenanthridin-8-yl group, phenanthridin-9-yl group, phenanthridin-10-yl group, phenazin-1-yl group, phenazine-2 -Yl group, benzo [h] quinolin-2-yl group, benzo [h] quinolin-3-yl group, benzo [h] quinolin-4-yl group, benzo [h] quinolin-5-yl group, benzo [h h] quinolin-6-yl group, benzo [h] quinolin-7-yl group, benzo [h] quinolin-8-yl group, benzo [h] quinolin-9-yl group, benzo [h] quinolin-10- Iru group, 2-thie Group, 3-thienyl group, 2-furyl group, 3-furyl group, benzothiophen-2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, Benzothiophen-6-yl group, benzothiophen-7-yl group, benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group Benzofuran-7-yl group, dibenzothiophen-1-yl group, dibenzothiophen-2-yl group, dibenzothiophen-3-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3- Yl group, 3-methylthiophen-2-yl group, 4-methylthiophen-2-yl group, 5-methylthiophen-2-yl group 2-methylthiophen-3-yl group, 4-methylthiophen-3-yl group, 5-methylthiophen-3-yl group, 3-methylfuran-2-yl group, 4-methylfuran-2-yl group 5-methylfuran-2-yl group, 2-methylfuran-3-yl group, 4-methylfuran-3-yl group, 5-methylfuran-3-yl group, 3-methylbenzothiophen-2-yl Group, 4-methylbenzothiophen-2-yl group, 5-methylbenzothiophen-2-yl group, 6-methylbenzothiophen-2-yl group, 7-methylbenzothiophen-2-yl group, 2-methylbenzo Thiophen-3-yl group, 4-methylbenzothiophen-3-yl group, 5-methylbenzothiophen-3-yl group, 6-methylbenzothiophen-3-yl group, 7-methylbenzothiol Nen-3-yl group, 2-methylbenzothiophen-4-yl group, 3-methylbenzothiophen-4-yl group, 5-methylbenzothiophen-4-yl group, 6-methylbenzothiophen-4-yl Group, 7-methylbenzothiophen-4-yl group, 2-methylbenzothiophen-5-yl group, 3-methylbenzothiophen-5-yl group, 4-methylbenzothiophen-5-yl group, 6-methylbenzo Thiophen-5-yl group, 7-methylbenzothiophen-5-yl group, 2-methylbenzothiophen-6-yl group, 3-methylbenzothiophen-6-yl group, 4-methylbenzothiophen-6-yl group 5-methylbenzothiophen-6-yl group, 7-methylbenzothiophen-6-yl group, 2-methylbenzothiophen-7-yl group, 3-methyl Benzothiophen-7-yl group, 4-methylbenzothiophen-7-yl group, 5-methylbenzothiophen-7-yl group, 6-methylbenzothiophen-7-yl group, 3-methylbenzofuran-2-yl group 4-methylbenzofuran-2-yl group, 5-methylbenzofuran-2-yl group, 6-methylbenzofuran-2-yl group, 7-methylbenzofuran-2-yl group, 2-methylbenzofuran-3-yl group 4-methylbenzofuran-3-yl group, 5-methylbenzofuran-3-yl group, 6-methylbenzofuran-3-yl group, 7-methylbenzofuran-3-yl group, 2-methylbenzofuran-4-yl group 3-methylbenzofuran-4-yl group, 5-methylbenzofuran-4-yl group, 6-methylbenzofuran-4-yl group, 7-methyl Nzofuran-4-yl group, 2-methylbenzofuran-5-yl group, 3-methylbenzofuran-5-yl group, 4-methylbenzofuran-5-yl group, 6-methylbenzofuran-5-yl group, 7-methyl Benzofuran-5-yl group, 2-methylbenzofuran-6-yl group, 3-methylbenzofuran-6-yl group, 4-methylbenzofuran-6-yl group, 5-methylbenzofuran-6-yl group, 7-methyl Benzofuran-6-yl group, 2-methylbenzofuran-7-yl group, 3-methylbenzofuran-7-yl group, 4-methylbenzofuran-7-yl group, 5-methylbenzofuran-7-yl group, 6-methyl Benzofuran-7-yl group, 2-methyldibenzothiophen-1-yl group, 3-methyldibenzothiophen-1-yl group, 4-methyldibenzo Thiophen-1-yl group, 6-methyldibenzothiophen-1-yl group, 7-methyldibenzothiophen-1-yl group, 8-methyldibenzothiophen-1-yl group, 9-methyldibenzothiophen-1-yl group 1-methyldibenzothiophen-2-yl group, 3-methyldibenzothiophen-2-yl group, 4-methyldibenzothiophen-2-yl group, 6-methyldibenzothiophen-2-yl group, 7-methyldibenzothiophene -2-yl group, 8-methyldibenzothiophen-2-yl group, 9-methyldibenzothiophen-2-yl group, 1-methyldibenzothiophen-3-yl group, 2-methyldibenzothiophen-3-yl group, 4-methyldibenzothiophen-3-yl group, 6-methyldibenzothiophen-3-yl group, 7-methyldi Nzothiophen-3-yl group, 8-methyldibenzothiophen-3-yl group, 9-methyldibenzothiophen-3-yl group, 2-methyldibenzofuran-1-yl group, 3-methyldibenzofuran-1-yl group, 4 -Methyldibenzofuran-1-yl group, 6-methyldibenzofuran-1-yl group, 7-methyldibenzofuran-1-yl group, 8-methyldibenzofuran-1-yl group, 9-methyldibenzofuran-1-yl group, -Methyldibenzofuran-2-yl group, 3-methyldibenzofuran-2-yl group, 4-methyldibenzofuran-2-yl group, 6-methyldibenzofuran-2-yl group, 7-methyldibenzofuran-2-yl group, 8 -Methyldibenzofuran-2-yl group, 9-methyldibenzofuran-2-yl group, 1-methyldibenzof N-yl group, 2-methyldibenzofuran-3-yl group, 4-methyldibenzofuran-3-yl group, 6-methyldibenzofuran-3-yl group, 7-methyldibenzofuran-3-yl group, 8-methyl Dibenzofuran-3-yl group, 9-methyldibenzofuran-3-yl group, 3-phenylthiophen-2-yl group, 4-phenylthiophen-2-yl group, 5-phenylthiophen-2-yl group, 2-phenyl Thiophen-3-yl group, 4-phenylthiophen-3-yl group, 5-phenylthiophen-3-yl group, 3-phenylfuran-2-yl group, 4-phenylfuran-2-yl group, 5-phenyl Furan-2-yl, 2-phenylfuran-3-yl, 4-phenylfuran-3-yl, 5-phenylfuran-3-yl, 3-phenylfuran Nzothiophen-2-yl group, 4-phenylbenzothiophen-2-yl group, 5-phenylbenzothiophen-2-yl group, 6-phenylbenzothiophen-2-yl group, 7-phenylbenzothiophen-2-yl group 2-phenylbenzothiophen-3-yl group, 4-phenylbenzothiophen-3-yl group, 5-phenylbenzothiophen-3-yl group, 6-phenylbenzothiophen-3-yl group, 7-phenylbenzothiophene -3-yl group, 2-phenylbenzothiophen-4-yl group, 3-phenylbenzothiophen-4-yl group, 5-phenylbenzothiophen-4-yl group, 6-phenylbenzothiophen-4-yl group, 7-phenylbenzothiophen-4-yl group, 2-phenylbenzothiophen-5-yl group, 3-phenyl Rubenzothiophen-5-yl group, 4-phenylbenzothiophen-5-yl group, 6-phenylbenzothiophen-5-yl group, 7-phenylbenzothiophen-5-yl group, 2-phenylbenzothiophene-6- Yl group, 3-phenylbenzothiophen-6-yl group, 4-phenylbenzothiophen-6-yl group, 5-phenylbenzothiophen-6-yl group, 7-phenylbenzothiophen-6-yl group, 2-phenyl Benzothiophen-7-yl group, 3-phenylbenzothiophen-7-yl group, 4-phenylbenzothiophen-7-yl group, 5-phenylbenzothiophen-7-yl group, 6-phenylbenzothiophen-7-yl Group, 3-phenylbenzofuran-2-yl group, 4-phenylbenzofuran-2-yl group, 5-phenyl Benzofuran-2-yl group, 6-phenylbenzofuran-2-yl group, 7-phenylbenzofuran-2-yl group, 2-phenylbenzofuran-3-yl group, 4-phenylbenzofuran-3-yl group, 5-phenyl Benzofuran-3-yl group, 6-phenylbenzofuran-3-yl group, 7-phenylbenzofuran-3-yl group, 2-phenylbenzofuran-4-yl group, 3-phenylbenzofuran-4-yl group, 5-phenyl Benzofuran-4-yl group, 6-phenylbenzofuran-4-yl group, 7-phenylbenzofuran-4-yl group, 2-phenylbenzofuran-5-yl group, 3-phenylbenzofuran-5-yl group, 4-phenyl Benzofuran-5-yl group, 6-phenylbenzofuran-5-yl group, 7-phenylbenzofuran-5-i Group, 2-phenylbenzofuran-6-yl group, 3-phenylbenzofuran-6-yl group, 4-phenylbenzofuran-6-yl group, 5-phenylbenzofuran-6-yl group, 7-phenylbenzofuran-6- Yl group, 2-phenylbenzofuran-7-yl group, 3-phenylbenzofuran-7-yl group, 4-phenylbenzofuran-7-yl group, 5-phenylbenzofuran-7-yl group, 6-phenylbenzofuran-7- Yl group, 2-phenyldibenzothiophen-1-yl group, 3-phenyldibenzothiophen-1-yl group, 4-phenyldibenzothiophen-1-yl group, 6-phenyldibenzothiophen-1-yl group, 7-phenyl Dibenzothiophen-1-yl group, 8-phenyldibenzothiophen-1-yl group, 9-phenyldibe Zothiophen-1-yl group, 1-phenyldibenzothiophen-2-yl group, 3-phenyldibenzothiophen-2-yl group, 4-phenyldibenzothiophen-2-yl group, 6-phenyldibenzothiophen-2-yl group 7-phenyldibenzothiophen-2-yl group, 8-phenyldibenzothiophen-2-yl group, 9-phenyldibenzothiophen-2-yl group, 1-phenyldibenzothiophen-3-yl group, 2-phenyldibenzothiophene -3-yl group, 4-phenyldibenzothiophen-3-yl group, 6-phenyldibenzothiophen-3-yl group, 7-phenyldibenzothiophen-3-yl group, 8-phenyldibenzothiophen-3-yl group, 9-phenyldibenzothiophen-3-yl group,
2-phenyldibenzofuran-1-yl group, 3-phenyldibenzofuran-1-yl group, 4-phenyldibenzofuran-1-yl group, 6-phenyldibenzofuran-1-yl group, 7-phenyldibenzofuran-1-yl group, 8-phenyldibenzofuran-1-yl group, 9-phenyldibenzofuran-1-yl group, 1-phenyldibenzofuran-2-yl group, 3-phenyldibenzofuran-2-yl group, 4-phenyldibenzofuran-2-yl group, 6-phenyldibenzofuran-2-yl group, 7-phenyldibenzofuran-2-yl group, 8-phenyldibenzofuran-2-yl group, 9-phenyldibenzofuran-2-yl group, 1-phenyldibenzofuran-3-yl group, 2-phenyldibenzofuran-3-yl group, 4-phenyldibenzofuran 3-yl group, 6-phenyldibenzofuran-3-yl group, 7-phenyldibenzofuran-3-yl group, 8-phenyldibenzofuran-3-yl group, 9-phenyldibenzofuran-3-yl group, 3- (2- Pyridyl) thiophen-2-yl group, 4- (2-pyridyl) thiophen-2-yl group, 5- (2-pyridyl) thiophen-2-yl group, 2- (2-pyridyl) thiophen-3-yl group 4- (2-pyridyl) thiophen-3-yl group, 5- (2-pyridyl) thiophen-3-yl group, 3- (2-pyridyl) furan-2-yl group, 4- (2-pyridyl) Furan-2-yl group, 5- (2-pyridyl) furan-2-yl group, 2- (2-pyridyl) furan-3-yl group, 4- (2-pyridyl) furan-3-yl group, 5 -(2-Pyridyl) furan- -Yl group, 3- (2-pyridyl) benzothiophen-2-yl group, 4- (2-pyridyl) benzothiophen-2-yl group, 5- (2-pyridyl) benzothiophen-2-yl group, 6 -(2-pyridyl) benzothiophen-2-yl group, 7- (2-pyridyl) benzothiophen-2-yl group, 2- (2-pyridyl) benzothiophen-3-yl group, 4- (2-pyridyl) ) Benzothiophen-3-yl group, 5- (2-pyridyl) benzothiophen-3-yl group, 6- (2-pyridyl) benzothiophen-3-yl group, 7- (2-pyridyl) benzothiophene-3 -Yl group, 2- (2-pyridyl) benzothiophen-4-yl group, 3- (2-pyridyl) benzothiophen-4-yl group, 5- (2-pyridyl) benzothiophen-4-yl group, 6 -( 2-pyridyl) benzothiophen-4-yl group, 7- (2-pyridyl) benzothiophen-4-yl group, 2- (2-pyridyl) benzothiophen-5-yl group, 3- (2-pyridyl) benzo Thiophen-5-yl group, 4- (2-pyridyl) benzothiophen-5-yl group, 6- (2-pyridyl) benzothiophen-5-yl group, 7- (2-pyridyl) benzothiophen-5-yl 2- (2-pyridyl) benzothiophen-6-yl group, 3- (2-pyridyl) benzothiophen-6-yl group, 4- (2-pyridyl) benzothiophen-6-yl group, 5- ( 2-pyridyl) benzothiophen-6-yl group, 7- (2-pyridyl) benzothiophen-6-yl group, 2- (2-pyridyl) benzothiophen-7-yl group, 3- (2-pyridyl) base Zothiophen-7-yl group, 4- (2-pyridyl) benzothiophen-7-yl group, 5- (2-pyridyl) benzothiophen-7-yl group, 6- (2-pyridyl) benzothiophen-7-yl Group, 3- (2-pyridyl) benzofuran-2-yl group, 4- (2-pyridyl) benzofuran-2-yl group, 5- (2-pyridyl) benzofuran-2-yl group, 6- (2-pyridyl) ) Benzofuran-2-yl group, 7- (2-pyridyl) benzofuran-2-yl group, 2- (2-pyridyl) benzofuran-3-yl group, 4- (2-pyridyl) benzofuran-3-yl group, 5- (2-pyridyl) benzofuran-3-yl group, 6- (2-pyridyl) benzofuran-3-yl group, 7- (2-pyridyl) benzofuran-3-yl group, 2- (2-pyridyl) benzof N-4-yl group, 3- (2-pyridyl) benzofuran-4-yl group, 5- (2-pyridyl) benzofuran-4-yl group, 6- (2-pyridyl) benzofuran-4-yl group, 7 -(2-pyridyl) benzofuran-4-yl group, 2- (2-pyridyl) benzofuran-5-yl group, 3- (2-pyridyl) benzofuran-5-yl group, 4- (2-pyridyl) benzofuran- 5-yl group, 6- (2-pyridyl) benzofuran-5-yl group, 7- (2-pyridyl) benzofuran-5-yl group, 2- (2-pyridyl) benzofuran-6-yl group, 3- ( 2-pyridyl) benzofuran-6-yl group, 4- (2-pyridyl) benzofuran-6-yl group, 5- (2-pyridyl) benzofuran-6-yl group, 7- (2-pyridyl) benzofuran-6- Il group, 2- ( 2-pyridyl) benzofuran-7-yl group, 3- (2-pyridyl) benzofuran-7-yl group, 4- (2-pyridyl) benzofuran-7-yl group, 5- (2-pyridyl) benzofuran-7- Yl group, 6- (2-pyridyl) benzofuran-7-yl group, 2- (2-pyridyl) dibenzothiophen-1-yl group, 3- (2-pyridyl) dibenzothiophen-1-yl group, 4- ( 2-pyridyl) dibenzothiophen-1-yl group, 6- (2-pyridyl) dibenzothiophen-1-yl group, 7- (2-pyridyl) dibenzothiophen-1-yl group, 8- (2-pyridyl) dibenzo Thiophen-1-yl group, 9- (2-pyridyl) dibenzothiophen-1-yl group, 1- (2-pyridyl) dibenzothiophen-2-yl group, 3- (2-pyridyl) diben Thiophen-2-yl group, 4- (2-pyridyl) dibenzothiophen-2-yl group, 6- (2-pyridyl) dibenzothiophen-2-yl group, 7- (2-pyridyl) dibenzothiophen-2-yl Group, 8- (2-pyridyl) dibenzothiophen-2-yl group, 9- (2-pyridyl) dibenzothiophen-2-yl group, 1- (2-pyridyl) dibenzothiophen-3-yl group, 2- ( 2-pyridyl) dibenzothiophen-3-yl group, 4- (2-pyridyl) dibenzothiophen-3-yl group, 6- (2-pyridyl) dibenzothiophen-3-yl group, 7- (2-pyridyl) dibenzo Thiophen-3-yl group, 8- (2-pyridyl) dibenzothiophen-3-yl group, 9- (2-pyridyl) dibenzothiophen-3-yl group,
2- (2-pyridyl) dibenzofuran-1-yl group, 3- (2-pyridyl) dibenzofuran-1-yl group, 4- (2-pyridyl) dibenzofuran-1-yl group, 6- (2-pyridyl) dibenzofuran -1-yl group, 7- (2-pyridyl) dibenzofuran-1-yl group, 8- (2-pyridyl) dibenzofuran-1-yl group, 9- (2-pyridyl) dibenzofuran-1-yl group, 1- (2-pyridyl) dibenzofuran-2-yl group, 3- (2-pyridyl) dibenzofuran-2-yl group, 4- (2-pyridyl) dibenzofuran-2-yl group, 6- (2-pyridyl) dibenzofuran-2 -Yl group, 7- (2-pyridyl) dibenzofuran-2-yl group, 8- (2-pyridyl) dibenzofuran-2-yl group, 9- (2-pyridyl) dibenzofuran-2-y Group, 1- (2-pyridyl) dibenzofuran-3-yl group, 2- (2-pyridyl) dibenzofuran-3-yl group, 4- (2-pyridyl) dibenzofuran-3-yl group, 6- (2-pyridyl) ) Dibenzofuran-3-yl group, 7- (2-pyridyl) dibenzofuran-3-yl group, 8- (2-pyridyl) dibenzofuran-3-yl group, 9- (2-pyridyl) dibenzofuran-3-yl group, 3- (3-pyridyl) thiophen-2-yl group, 4- (3-pyridyl) thiophen-2-yl group, 5- (3-pyridyl) thiophen-2-yl group, 2- (3-pyridyl) thiophene -3-yl group, 4- (3-pyridyl) thiophen-3-yl group, 5- (3-pyridyl) thiophen-3-yl group, 3- (3-pyridyl) furan-2-yl group, 4- (3-pyridyl) Lan-2-yl group, 5- (3-pyridyl) furan-2-yl group, 2- (3-pyridyl) furan-3-yl group, 4- (3-pyridyl) furan-3-yl group, 5 -(3-pyridyl) furan-3-yl group, 3- (3-pyridyl) benzothiophen-2-yl group, 4- (3-pyridyl) benzothiophen-2-yl group, 5- (3-pyridyl) Benzothiophen-2-yl group, 6- (3-pyridyl) benzothiophen-2-yl group, 7- (3-pyridyl) benzothiophen-2-yl group, 2- (3-pyridyl) benzothiophene-3- Yl group, 4- (3-pyridyl) benzothiophen-3-yl group, 5- (3-pyridyl) benzothiophen-3-yl group, 6- (3-pyridyl) benzothiophen-3-yl group, 7- (3-pyridyl) benzothiophene- 3-yl group, 2- (3-pyridyl) benzothiophen-4-yl group, 3- (3-pyridyl) benzothiophen-4-yl group, 5- (3-pyridyl) benzothiophen-4-yl group, 6- (3-pyridyl) benzothiophen-4-yl group, 7- (3-pyridyl) benzothiophen-4-yl group, 2- (3-pyridyl) benzothiophen-5-yl group, 3- (3- Pyridyl) benzothiophen-5-yl group, 4- (3-pyridyl) benzothiophen-5-yl group, 6- (3-pyridyl) benzothiophen-5-yl group, 7- (3-pyridyl) benzothiophene- 5-yl group, 2- (3-pyridyl) benzothiophen-6-yl group, 3- (3-pyridyl) benzothiophen-6-yl group, 4- (3-pyridyl) benzothiophen-6-yl group, 5- 3-pyridyl) benzothiophen-6-yl group, 7- (3-pyridyl) benzothiophen-6-yl group, 2- (3-pyridyl) benzothiophen-7-yl group, 3- (3-pyridyl) benzo Thiophen-7-yl group, 4- (3-pyridyl) benzothiophen-7-yl group, 5- (3-pyridyl) benzothiophen-7-yl group, 6- (3-pyridyl) benzothiophen-7-yl Group, 3- (3-pyridyl) benzofuran-2-yl group, 4- (3-pyridyl) benzofuran-2-yl group, 5- (3-pyridyl) benzofuran-2-yl group, 6- (3-pyridyl) ) Benzofuran-2-yl group, 7- (3-pyridyl) benzofuran-2-yl group, 2- (3-pyridyl) benzofuran-3-yl group, 4- (3-pyridyl) benzofuran-3-yl group 5- (3-pyridyl) benzofuran-3-yl group, 6- (3-pyridyl) benzofuran-3-yl group, 7- (3-pyridyl) benzofuran-3-yl group, 2- (3-pyridyl) benzofuran -4-yl group, 3- (3-pyridyl) benzofuran-4-yl group, 5- (3-pyridyl) benzofuran-4-yl group, 6- (3-pyridyl) benzofuran-4-yl group, 7- (3-pyridyl) benzofuran-4-yl group, 2- (3-pyridyl) benzofuran-5-yl group, 3- (3-pyridyl) benzofuran-5-yl group, 4- (3-pyridyl) benzofuran-5 -Yl group, 6- (3-pyridyl) benzofuran-5-yl group, 7- (3-pyridyl) benzofuran-5-yl group, 2- (3-pyridyl) benzofuran-6-yl group, 3- (3 -Pyridyl) Nzofuran-6-yl group, 4- (3-pyridyl) benzofuran-6-yl group, 5- (3-pyridyl) benzofuran-6-yl group, 7- (3-pyridyl) benzofuran-6-yl group, 2 -(3-pyridyl) benzofuran-7-yl group, 3- (3-pyridyl) benzofuran-7-yl group, 4- (3-pyridyl) benzofuran-7-yl group, 5- (3-pyridyl) benzofuran- 7-yl group, 6- (3-pyridyl) benzofuran-7-yl group, 2- (3-pyridyl) dibenzothiophen-1-yl group, 3- (3-pyridyl) dibenzothiophen-1-yl group, 4 -(3-pyridyl) dibenzothiophen-1-yl group, 6- (3-pyridyl) dibenzothiophen-1-yl group, 7- (3-pyridyl) dibenzothiophen-1-yl group, 8- (3-pyridyl) L) Dibenzothiophen-1-yl group, 9- (3-pyridyl) dibenzothiophen-1-yl group, 1- (3-pyridyl) dibenzothiophen-2-yl group, 3- (3-pyridyl) dibenzothiophene- 2-yl group, 4- (3-pyridyl) dibenzothiophen-2-yl group, 6- (3-pyridyl) dibenzothiophen-2-yl group, 7- (3-pyridyl) dibenzothiophen-2-yl group, 8- (3-pyridyl) dibenzothiophen-2-yl group, 9- (3-pyridyl) dibenzothiophen-2-yl group, 1- (3-pyridyl) dibenzothiophen-3-yl group, 2- (3- Pyridyl) dibenzothiophen-3-yl group, 4- (3-pyridyl) dibenzothiophen-3-yl group, 6- (3-pyridyl) dibenzothiophen-3-yl group, 7- 3-pyridyl) dibenzothiophen-3-yl group, 8- (3-pyridyl) dibenzothiophen-3-yl group, 9- (3-pyridyl) dibenzothiophen-3-yl group, 2- (3-pyridyl) dibenzofuran -1-yl group, 3- (3-pyridyl) dibenzofuran-1-yl group, 4- (3-pyridyl) dibenzofuran-1-yl group, 6- (3-pyridyl) dibenzofuran-1-yl group, 7- (3-pyridyl) dibenzofuran-1-yl group, 8- (3-pyridyl) dibenzofuran-1-yl group, 9- (3-pyridyl) dibenzofuran-1-yl group, 1- (3-pyridyl) dibenzofuran-2 -Yl group, 3- (3-pyridyl) dibenzofuran-2-yl group, 4- (3-pyridyl) dibenzofuran-2-yl group, 6- (3-pyridyl) dibenzofuran- 2-yl group, 7- (3-pyridyl) dibenzofuran-2-yl group, 8- (3-pyridyl) dibenzofuran-2-yl group, 9- (3-pyridyl) dibenzofuran-2-yl group, 1- ( 3-pyridyl) dibenzofuran-3-yl group, 2- (3-pyridyl) dibenzofuran-3-yl group, 4- (3-pyridyl) dibenzofuran-3-yl group, 6- (3-pyridyl) dibenzofuran-3- Yl group, 7- (3-pyridyl) dibenzofuran-3-yl group, 8- (3-pyridyl) dibenzofuran-3-yl group, 9- (3-pyridyl) dibenzofuran-3-yl group, 3- (4- Pyridyl) thiophen-2-yl group, 4- (4-pyridyl) thiophen-2-yl group, 5- (4-pyridyl) thiophen-2-yl group, 2- (4-pyridyl) thiophen-3-yl group 4- (4-pyridyl) thiophene-3-yl group, 5- (4-pyridyl) thiophene-3-yl group,
3- (4-pyridyl) furan-2-yl group, 4- (4-pyridyl) furan-2-yl group, 5- (4-pyridyl) furan-2-yl group, 2- (4-pyridyl) furan -3-yl group, 4- (4-pyridyl) furan-3-yl group, 5- (4-pyridyl) furan-3-yl group, 3- (4-pyridyl) benzothiophen-2-yl group, 4 -(4-pyridyl) benzothiophen-2-yl group, 5- (4-pyridyl) benzothiophen-2-yl group, 6- (4-pyridyl) benzothiophen-2-yl group, 7- (4-pyridyl) ) Benzothiophen-2-yl group, 2- (4-pyridyl) benzothiophen-3-yl group, 4- (4-pyridyl) benzothiophen-3-yl group, 5- (4-pyridyl) benzothiophene-3 -Yl group, 6- (4-pyridyl) benzo Offen-3-yl group, 7- (4-pyridyl) benzothiophen-3-yl group, 2- (4-pyridyl) benzothiophen-4-yl group, 3- (4-pyridyl) benzothiophen-4-yl Group, 5- (4-pyridyl) benzothiophen-4-yl group, 6- (4-pyridyl) benzothiophen-4-yl group, 7- (4-pyridyl) benzothiophen-4-yl group, 2- ( 4-pyridyl) benzothiophen-5-yl group, 3- (4-pyridyl) benzothiophen-5-yl group, 4- (4-pyridyl) benzothiophen-5-yl group, 6- (4-pyridyl) benzo Thiophen-5-yl group, 7- (4-pyridyl) benzothiophen-5-yl group, 2- (4-pyridyl) benzothiophen-6-yl group, 3- (4-pyridyl) benzothiophene-6- 4- (4-pyridyl) benzothiophen-6-yl group, 5- (4-pyridyl) benzothiophen-6-yl group, 7- (4-pyridyl) benzothiophen-6-yl group, 2- (4-pyridyl) benzothiophen-7-yl group, 3- (4-pyridyl) benzothiophen-7-yl group, 4- (4-pyridyl) benzothiophen-7-yl group, 5- (4-pyridyl) Benzothiophen-7-yl group, 6- (4-pyridyl) benzothiophen-7-yl group, 3- (4-pyridyl) benzofuran-2-yl group, 4- (4-pyridyl) benzofuran-2-yl group 5- (4-pyridyl) benzofuran-2-yl group, 6- (4-pyridyl) benzofuran-2-yl group, 7- (4-pyridyl) benzofuran-2-yl group, 2- (4-pyridyl) Benzofura 3-yl group, 4- (4-pyridyl) benzofuran-3-yl group, 5- (4-pyridyl) benzofuran-3-yl group, 6- (4-pyridyl) benzofuran-3-yl group, 7 -(4-pyridyl) benzofuran-3-yl group, 2- (4-pyridyl) benzofuran-4-yl group, 3- (4-pyridyl) benzofuran-4-yl group, 5- (4-pyridyl) benzofuran- 4-yl group, 6- (4-pyridyl) benzofuran-4-yl group, 7- (4-pyridyl) benzofuran-4-yl group, 2- (4-pyridyl) benzofuran-5-yl group, 3- ( 4-pyridyl) benzofuran-5-yl group, 4- (4-pyridyl) benzofuran-5-yl group, 6- (4-pyridyl) benzofuran-5-yl group, 7- (4-pyridyl) benzofuran-5 Il group, 2- ( -Pyridyl) benzofuran-6-yl group, 3- (4-pyridyl) benzofuran-6-yl group, 4- (4-pyridyl) benzofuran-6-yl group, 5- (4-pyridyl) benzofuran-6-yl Groups, 7- (4-pyridyl) benzofuran-6-yl group, 2- (4-pyridyl) benzofuran-7-yl group, 3- (4-pyridyl) benzofuran-7-yl group, 4- (4-pyridyl) ) Benzofuran-7-yl group, 5- (4-pyridyl) benzofuran-7-yl group, 6- (4-pyridyl) benzofuran-7-yl group, 2- (4-pyridyl) dibenzothiophen-1-yl group 3- (4-pyridyl) dibenzothiophen-1-yl group, 4- (4-pyridyl) dibenzothiophen-1-yl group, 6- (4-pyridyl) dibenzothiophen-1-yl group, 7- 4-pyridyl) dibenzothiophen-1-yl group, 8- (4-pyridyl) dibenzothiophen-1-yl group, 9- (4-pyridyl) dibenzothiophen-1-yl group, 1- (4-pyridyl) dibenzo Thiophen-2-yl group, 3- (4-pyridyl) dibenzothiophen-2-yl group, 4- (4-pyridyl) dibenzothiophen-2-yl group, 6- (4-pyridyl) dibenzothiophen-2-yl 7- (4-pyridyl) dibenzothiophen-2-yl group, 8- (4-pyridyl) dibenzothiophen-2-yl group, 9- (4-pyridyl) dibenzothiophen-2-yl group, 1- ( 4-pyridyl) dibenzothiophen-3-yl group, 2- (4-pyridyl) dibenzothiophen-3-yl group, 4- (4-pyridyl) dibenzothiophen-3-yl group 6- (4-pyridyl) dibenzothiophen-3-yl group, 7- (4-pyridyl) dibenzothiophen-3-yl group, 8- (4-pyridyl) dibenzothiophen-3-yl group, 9- ( 4-pyridyl) dibenzothiophen-3-yl group,
2- (4-pyridyl) dibenzofuran-1-yl group, 3- (4-pyridyl) dibenzofuran-1-yl group, 4- (4-pyridyl) dibenzofuran-1-yl group, 6- (4-pyridyl) dibenzofuran -1-yl group, 7- (4-pyridyl) dibenzofuran-1-yl group, 8- (4-pyridyl) dibenzofuran-1-yl group, 9- (4-pyridyl) dibenzofuran-1-yl group, 1- (4-pyridyl) dibenzofuran-2-yl group, 3- (4-pyridyl) dibenzofuran-2-yl group, 4- (4-pyridyl) dibenzofuran-2-yl group, 6- (4-pyridyl) dibenzofuran-2 -Yl group, 7- (4-pyridyl) dibenzofuran-2-yl group, 8- (4-pyridyl) dibenzofuran-2-yl group, 9- (4-pyridyl) dibenzofuran-2-y Group, 1- (4-pyridyl) dibenzofuran-3-yl group, 2- (4-pyridyl) dibenzofuran-3-yl group, 4- (4-pyridyl) dibenzofuran-3-yl group, 6- (4-pyridyl) ) Dibenzofuran-3-yl group, 7- (4-pyridyl) dibenzofuran-3-yl group, 8- (4-pyridyl) dibenzofuran-3-yl group, 9- (4-pyridyl) dibenzofuran-3-yl group, 2- {8- (2-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (2-pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (2-pyridyl) dibenzofuran- 2-yl} phenyl group, 2- {8- (3-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (3-pyridyl) dibenzofuran-2-yl} phenyl group, 4- 8- (3-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (4-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (4-pyridyl) dibenzofuran-2-yl } Phenyl group, 4- {8- (4-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8 -(3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2- Methyl-3-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (2-methyl-3-pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (2-methyl-3- Pyridyl ) Dibenzofuran-2-yl} phenyl group, 2- {8- (3-methyl-4-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (3-methyl-4-pyridyl) dibenzofuran-2 -Yl} phenyl group, 4- {8- (3-methyl-4-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl } Phenyl group, 3- {8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl} phenyl group, 4- {8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl } Phenyl group, 2- {8- (2-pyrimidyl) dibenzofuran-2-yl} phenyl group, 3- {8- (2-pyrimidyl) dibenzofuran-2-yl} phenyl group, 4- {8- (2- Pil Diyl) dibenzofuran-2-yl} phenyl group, 2- {8- (5-pyrimidyl) dibenzofuran-2-yl} phenyl group, 3- {8- (5-pyrimidyl) dibenzofuran-2-yl} phenyl group, 4 Preferred examples include — {8- (5-pyrimidyl) dibenzofuran-2-yl} phenyl group and the like. Of these substituents, a phenyl group, a p-tolyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 3- (1-naphthyl) phenyl group, 3 -(2-naphthyl) phenyl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3- (9-phenanthryl) phenyl group, 4- (9-phenanthryl) phenyl group, 3 -(Fluoranthen-3-yl) phenyl group, 4- (fluoranthen-3-yl) phenyl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3-pyridyl) Phenyl group, 4- (3-pyridyl) phenyl group, 3- (2-quinolyl) phenyl group, 4- (2-quinolyl) phenyl group, 3- (3-quinolyl) phenyl group, 4- (3-quinolyl) F Nyl group, 3- (5-methylthiophen-2-yl) phenyl group, 4- (5-methylthiophen-2-yl) phenyl group, 3- (5-methylfuran-2-yl) phenyl group, 4- (5-methylfuran-2-yl) phenyl group, 3- (2-benzothienyl) phenyl group, 4- (2-benzothienyl) phenyl group, 3- (2-benzofuryl) phenyl group, 4- (2- Benzofuryl) phenyl group, 3- (2-dibenzothienyl) phenyl group, 4- (2-dibenzothienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4- (4-dibenzothienyl) phenyl group, 3 -(2-dibenzofuryl) phenyl group, 4- (2-dibenzofuryl) phenyl group, 3- (4-dibenzofuryl) phenyl group, 4- (4-dibenzofuryl) phenyl group, 2- Enylpyridin-6-yl group, 2-phenylpyridin-5-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-5-yl group, 3-phenylpyridin-6-yl group, 5-phenyl Thiophen-2-yl group, 5-phenylfuran-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-benzothienyl group, 2-benzofuryl group, 1-phenanthryl group, 2-phenanthryl group, 3- Phenanthryl group, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, 4-dibenzofuryl group, 2- {8- (3-methyl-2-pyridyl) dibenzofuran-2- Yl} phenyl group, 3- {8- (3-methyl-2-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2,6-dimethyl) -3-pyridyl) dibenzofuran-2-yl} phenyl group, 3- {8- (2,6-dimethyl-3-pyridyl) dibenzofuran-2-yl} phenyl group, 2- {8- (2-pyrimidyl) dibenzofuran -2-yl} phenyl group or 3- {8- (2-pyrimidyl) dibenzofuran-2-yl} phenyl group is preferable, and phenyl group, biphenyl-3-yl group, biphenyl-4-yl group, 3- ( 1-naphthyl) phenyl group, 3- (2-naphthyl) phenyl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3- (9-phenanthryl) phenyl group, 4- ( 9-phenanthryl) phenyl group, 3- (fluoranthen-3-yl) phenyl group, 4- (fluoranthen-3-yl) phenyl group, 3- (2-pyridyl) phenyl group, -(2-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 3- (2-quinolyl) phenyl group, 4- (2-quinolyl) phenyl group, 3 -(3-quinolyl) phenyl group, 4- (3-quinolyl) phenyl group, 3- (2-benzothienyl) phenyl group, 4- (2-benzothienyl) phenyl group, 3- (2-benzofuryl) phenyl group 4- (2-benzofuryl) phenyl group, 3- (2-dibenzothienyl) phenyl group, 4- (2-dibenzothienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4- (4-dibenzo Thienyl) phenyl group, 3- (2-dibenzofuryl) phenyl group, 4- (2-dibenzofuryl) phenyl group, 3- (4-dibenzofuryl) phenyl group, 4- (4-dibenzoph) ) Phenyl group, 1-naphthyl, 2-naphthyl, 9-phenanthryl group, 2-dibenzothienyl group, 2-dibenzofuryl group, 4-dibenzothienyl group, or a 4-dibenzofuryl group are more preferable.
　Ａは、単結合を表す。 A represents a single bond.
　Ｂ１及びＢ２は、単結合又は水素原子を表す。但し、Ｂ１又はＢ２の何れか一方が単結合を表してＡと単結合を形成し、もう一方は水素原子を表す。 B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
　Ｚ１及びＺ２の何れか一方が窒素原子を表し、もう一方はＣ－Ｈを表す。 One of Z 1 and Z 2 represents a nitrogen atom, and the other represents C—H.
　一般式（１）で表される化合物は、下記の通り一般式（１ａ）又は（１ｂ）で表される化合物と表記することもできる。 The compound represented by the general formula (1) can also be expressed as a compound represented by the general formula (1a) or (1b) as follows.
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
（一般式（１ａ）及び（１ｂ）中、Ａｒ１Ａｒ２、Ａｒ３、Ａｒ４、Ａｒ５、Ａｒ６、Ａｒ７、Ｚ１、及びＺ２は、前記一般式（１）と同義である。）
　一般式（１ａ）及び（１ｂ）において、各定義の好ましい範囲については、一般式（１）と同じである。 (In the general formulas (1a) and (1b), Ar 1 Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Z 1 , and Z 2 have the same meanings as the general formula (1). .)
In general formulas (1a) and (1b), the preferred range of each definition is the same as in general formula (1).
　本発明のトリアジン化合物（１）は有機電界発光素子の構成成分の一部として用いると、高発光効率化、長寿命化、低電圧化等の効果が得られる。特に、電子輸送層として用いた場合にこの効果が顕著に現れる。 When the triazine compound (1) of the present invention is used as a part of the components of the organic electroluminescent device, effects such as high luminous efficiency, long life, and low voltage can be obtained. In particular, this effect is prominent when used as an electron transport layer.
　一般式（１）で示される化合物のうち、特に好ましい化合物の具体例としては、次の（Ａ－１）から（Ａ－９６０）を例示できるが、本発明はこれらに限定されるものではない。 Specific examples of particularly preferable compounds among the compounds represented by the general formula (1) include the following (A-1) to (A-960), but the present invention is not limited thereto. .
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
　以下、トリアジン化合物（１）の使用方法について説明する。 Hereinafter, a method of using the triazine compound (1) will be described.
　有機電界発光素子における発光層は、広義の意味では、陰極と陽極からなる電極に電流を流した際に発光する層のことを指す。具体的には、陰極と陽極からなる電極に電流を流した際に発光する蛍光性化合物を含有する層のことを指す。通常、有機電界発光素子は一対の電極の間に発光層を挟持した構造をとる。 In the broad sense, the light emitting layer in an organic electroluminescent element refers to a layer that emits light when a current is passed through an electrode composed of a cathode and an anode. Specifically, it refers to a layer containing a fluorescent compound that emits light when an electric current is passed through an electrode composed of a cathode and an anode. Usually, an organic electroluminescent element has a structure in which a light emitting layer is sandwiched between a pair of electrodes.
　本発明の有機電界発光素子は、必要に応じ発光層の他に、正孔輸送層、電子輸送層、陽極バッファー層及び陰極バッファー層等を有し、陰極と陽極で挟持された構造をとる。具体的には以下に示される構造が挙げられる。
（ｉ）陽極／発光層／陰極
（ｉｉ）陽極／正孔輸送層／発光層／陰極
（ｉｉｉ）陽極／発光層／電子輸送層／陰極
（ｉｖ）陽極／正孔輸送層／発光層／電子輸送層／陰極
（ｖ）陽極／陽極バッファー層／正孔輸送層／発光層／電子輸送層／陰極バッファー層／陰極
　本発明の有機電界発光素子における発光層には、従来公知の発光材料を用いることができる。発光層を形成する方法としては、例えば蒸着法、スピンコート法、キャスト法、ＬＢ法などの公知の方法により薄膜を形成する方法がある。 The organic electroluminescent device of the present invention has a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer, etc. in addition to the light emitting layer as required, and has a structure sandwiched between a cathode and an anode. Specific examples include the structures shown below.
(I) Anode / light emitting layer / cathode (ii) Anode / hole transport layer / light emitting layer / cathode (iii) Anode / light emitting layer / electron transport layer / cathode (iv) anode / hole transport layer / light emitting layer / electron Transport layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode buffer layer / cathode For the light emitting layer in the organic electroluminescent device of the present invention, a conventionally known light emitting material is used. be able to. As a method for forming the light emitting layer, for example, there is a method of forming a thin film by a known method such as a vapor deposition method, a spin coating method, a casting method, or an LB method.
　又、この発光層は、樹脂などの結着材と共に発光材料を溶剤に溶かして溶液とした後、これをスピンコート法などにより塗布して薄膜形成することにより得ることができる。 Further, the light emitting layer can be obtained by dissolving a light emitting material in a solvent together with a binder such as a resin to form a solution and then applying the solution by a spin coating method to form a thin film.
　このようにして形成された発光層の膜厚については特に制限はなく、状況に応じて適宜選択することができるが、通常は５ｎｍ～５μｍの範囲である。 The film thickness of the light emitting layer thus formed is not particularly limited and can be appropriately selected according to the situation, but is usually in the range of 5 nm to 5 μm.
　次に正孔注入層、正孔輸送層、電子注入層、電子輸送層等、発光層と組み合わせて有機電界発光素子を構成するその他の層について説明する。 Next, other layers constituting the organic electroluminescence device in combination with the light emitting layer, such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, will be described.
　正孔注入層、正孔輸送層は、陽極より注入された正孔を発光層に伝達する機能を有し、この正孔注入層、正孔輸送層を陽極と発光層の間に介在させることにより、より低い電界で多くの正孔が発光層に注入される。 The hole injection layer and the hole transport layer have a function of transmitting the holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer are interposed between the anode and the light emitting layer. Thus, many holes are injected into the light emitting layer with a lower electric field.
　また、陰極から注入され、電子注入層及び／又は電子輸送層より発光層に輸送された電子は、発光層と正孔注入層もしくは正孔輸送層の界面に存在する電子の障壁により、正孔注入層もしくは正孔輸送層に漏れることなく発光層内の界面に累積され、発光効率が向上するなど発光性能の優れた素子となる。 In addition, electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light-emitting layer are generated by the electron barrier existing at the interface between the light-emitting layer and the hole injection layer or the hole transport layer. It accumulates at the interface in the light emitting layer without leaking into the injection layer or the hole transport layer, resulting in an element with excellent light emitting performance such as improved luminous efficiency.
　上記正孔注入材料、正孔輸送材料は、正孔の注入もしくは輸送、電子の障壁性の何れかを有するものであり、有機物、無機物の何れであってもよい。この正孔注入材料、正孔輸送材料としては、例えばトリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、アニリン系共重合体、又、導電性高分子オリゴマー、特にチオフェンオリゴマーなどが挙げられる。正孔注入材料、正孔輸送材料としては、上記のものを使用することができるが、ポルフィリン化合物、芳香族第三級アミン化合物及びスチリルアミン化合物、特に芳香族第三級アミン化合物を用いることが好ましい。 The hole injecting material and the hole transporting material have either hole injection or transport or electron barrier properties, and may be either organic or inorganic. Examples of the hole injection material and hole transport material include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazoles. Derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers. As the hole injecting material and the hole transporting material, those described above can be used, and porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds can be used. preferable.
　上記芳香族第三級アミン化合物及びスチリルアミン化合物の代表例としては、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラフェニル－４，４’－ジアミノフェニル、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ビス（３－メチルフェニル）－〔１，１’－ビフェニル〕－４，４’－ジアミン（ＴＰＤ）、２，２－ビス（４－ジ－ｐ－トリルアミノフェニル）プロパン、１，１－ビス（４－ジ－ｐ－トリルアミノフェニル）シクロヘキサン、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラ－ｐ－トリル－４，４’－ジアミノビフェニル、１，１－ビス（４－ジ－ｐ－トリルアミノフェニル）－４－フェニルシクロヘキサン、ビス（４－ジメチルアミノ－２－メチルフェニル）フェニルメタン、ビス（４－ジ－ｐ－トリルアミノフェニル）フェニルメタン、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（４－メトキシフェニル）－４，４’－ジアミノビフェニル、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラフェニル－４，４’－ジアミノジフェニルエーテル、４，４’－ビス（ジフェニルアミノ）クオードリフェニル、Ｎ，Ｎ，Ｎ－トリ（ｐ－トリル）アミン、４－（ジ－ｐ－トリルアミノ）－４’－〔４－（ジ－ｐ－トリルアミノ）スチリル〕スチルベン、４－Ｎ，Ｎ－ジフェニルアミノ－（２－ジフェニルビニル）ベンゼン、３－メトキシ－４’－Ｎ，Ｎ－ジフェニルアミノスチルベンゼン、Ｎ－フェニルカルバゾール、４，４’－ビス〔Ｎ－（１－ナフチル）－Ｎ－フェニルアミノ〕ビフェニル（ＮＰＤ）、４，４’，４’’－トリス〔Ｎ－（３－メチルフェニル）－Ｎ－フェニルアミノ〕トリフェニルアミン（ＭＴＤＡＴＡ）などがあげられる。 Representative examples of the aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′. -Bis (3-methylphenyl)-[1,1'-biphenyl] -4,4'-diamine (TPD), 2,2-bis (4-di-p-tolylaminophenyl) propane, 1,1- Bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl, 1,1-bis (4-di-p- Tolylaminophenyl) -4-phenylcyclohexane, bis (4-dimethylamino-2-methylphenyl) phenylmethane, bis (4-di-p-tolylaminophenyl) phenylmethane, N, N′-diphenyl-N, '-Di (4-methoxyphenyl) -4,4'-diaminobiphenyl, N, N, N', N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis (diphenylamino) c Audriphenyl, N, N, N-tri (p-tolyl) amine, 4- (di-p-tolylamino) -4 ′-[4- (di-p-tolylamino) styryl] stilbene, 4-N, N— Diphenylamino- (2-diphenylvinyl) benzene, 3-methoxy-4'-N, N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis [N- (1-naphthyl) -N-phenyl Amino] biphenyl (NPD), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA) It is.
　又、ｐ型－Ｓｉ、ｐ型－ＳｉＣなどの無機化合物も正孔注入材料、正孔輸送材料として使用することができる。この正孔注入層、正孔輸送層は、上記正孔注入材料、正孔輸送材料を、例えば真空蒸着法、スピンコート法、キャスト法、ＬＢ法などの公知の方法により、薄膜化することにより形成することができる。正孔注入層、正孔輸送層の膜厚については特に制限はないが、通常は５ｎｍ～５μｍ程度である。この正孔注入層、正孔輸送層は、上記材料の一種又は二種以上からなる一層構造であってもよく、同一組成又は異種組成の複数層からなる積層構造であってもよい。 Also, inorganic compounds such as p-type-Si and p-type-SiC can be used as the hole injection material and the hole transport material. The hole injection layer and the hole transport layer are formed by thinning the hole injection material and the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Can be formed. The film thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually about 5 nm to 5 μm. The hole injection layer and hole transport layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
　本発明の有機電界発光素子において、電子輸送層は上記一般式（１）で表されるトリアジン化合物を含むものである。 In the organic electroluminescent element of the present invention, the electron transport layer contains a triazine compound represented by the general formula (1).
　当該電子輸送層は、上記一般式（１）で表されるトリアジン化合物を、例えば真空蒸着法、スピンコート法、キャスト法、ＬＢ法などの公知の薄膜形成法により成膜して形成することができる。電子輸送層の膜厚は特に制限はないが、通常は５ｎｍ～５μｍの範囲で選ばれる。また、この電子輸送層は、一般式（１）で表されるトリアジン化合物を含み、かつ従来公知の電子輸送材料を含んでいてもよく、一種又は二種以上からなる一層構造であってもよいし、或いは、同一組成又は異種組成の複数層からなる積層構造であってもよい。 The electron transport layer may be formed by forming the triazine compound represented by the general formula (1) by a known thin film forming method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. it can. The thickness of the electron transport layer is not particularly limited, but is usually selected in the range of 5 nm to 5 μm. Further, this electron transport layer contains a triazine compound represented by the general formula (1), may contain a conventionally known electron transport material, and may have a single-layer structure composed of one kind or two or more kinds. Alternatively, a laminated structure composed of a plurality of layers having the same composition or different compositions may be used.
　又、本発明においては、発光材料は発光層のみに限定することはなく、発光層に隣接した正孔輸送層、又は電子輸送層に１種含有させてもよく、それにより更に有機電界発光素子の発光効率を高めることができる。 In the present invention, the light emitting material is not limited to the light emitting layer, but may be contained in the hole transport layer or the electron transport layer adjacent to the light emitting layer. The luminous efficiency can be increased.
　本発明の有機電界発光素子に好ましく用いられる基板は、ガラス、プラスチックなどの種類には特に限定はなく、又、透明のものであれば特に制限はない。本発明の有機電界発光素子に好ましく用いられる基板としては例えばガラス、石英、光透過性プラスチックフィルムを挙げることができる。 The substrate that is preferably used in the organic electroluminescent device of the present invention is not particularly limited in the type of glass, plastic, etc., and is not particularly limited as long as it is transparent. Examples of the substrate preferably used in the organic electroluminescence device of the present invention include glass, quartz, and a light transmissive plastic film.
　光透過性プラスチックフィルムとしては、例えばポリエチレンテレフタレート（ＰＥＴ）、ポリエチレンナフタレート（ＰＥＮ）、ポリエーテルスルホン（ＰＥＳ）、ポリエーテルイミド、ポリエーテルエーテルケトン、ポリフェニレンスルフィド、ポリアリレート、ポリイミド、ポリカーボネート（ＰＣ）、セルローストリアセテート（ＴＡＣ）、セルロースアセテートプロピオネート（ＣＡＰ）等からなるフィルム等が挙げられる。 Examples of the light transmissive plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate (PC). And a film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP), or the like.
　本発明の有機電界発光素子を作製する好適な例を説明する。例として、前記の陽極／正孔注入層／正孔輸送層／発光層／電子輸送層／電子注入層／陰極からなる有機電界発光素子の作製法について説明する。 A preferred example of producing the organic electroluminescence device of the present invention will be described. As an example, a method for producing an organic electroluminescent element composed of the anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode will be described.
　まず適当な基板上に、所望の電極用物質、例えば陽極用物質からなる薄膜を、１μｍ以下、好ましくは１０～２００ｎｍの範囲の膜厚になるように、蒸着やスパッタリングなどの方法により形成させて陽極を作製する。次に、この上に素子材料である正孔注入層、正孔輸送層、発光層、電子輸送層／電子注入層からなる薄膜を形成させる。 First, a thin film made of a desired electrode material, for example, an anode material, is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably in the range of 10 to 200 nm. An anode is produced. Next, a thin film comprising a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer / electron injection layer, which is a device material, is formed thereon.
　なお、陽極と発光層又は正孔注入層の間、及び、陰極と発光層又は電子注入層との間にはバッファー層（電極界面層）を存在させてもよい。 A buffer layer (electrode interface layer) may exist between the anode and the light emitting layer or the hole injection layer and between the cathode and the light emitting layer or the electron injection layer.
　更に上記基本構成層の他に必要に応じてその他の機能を有する層を積層してもよく、例えば正孔ブロック層、電子ブロック層などのような機能層を有していてもよい。 Furthermore, in addition to the basic constituent layer, a layer having other functions may be laminated as necessary. For example, a functional layer such as a hole blocking layer or an electron blocking layer may be provided.
　次に、本発明の有機電界発光素子の電極について説明する。有機電界発光素子における陽極としては、仕事関数の大きい（４ｅＶ以上）金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはＡｕなどの金属、ＣｕＩ、酸化インジウム－スズ（ＩＴＯ）、ＳｎＯ２、ＺｎＯなどの導電性透明材料が挙げられる。 Next, the electrode of the organic electroluminescent element of the present invention will be described. As the anode in the organic electroluminescence device, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such an electrode substance include a conductive transparent material such as a metal such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
　上記陽極は蒸着やスパッタリングなどの方法によりこれらの電極物質の薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、或いは蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。 The anode may be formed by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by photolithography, or the pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering. May be formed.
　一方、陰極としては、仕事関数の小さい（４ｅＶ以下）金属（電子注入性金属と称する）、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム－カリウム合金、マグネシウム、リチウム、マグネシウム／銅混合物、マグネシウム／銀混合物、マグネシウム／アルミニウム混合物、マグネシウム／インジウム混合物、アルミニウム／酸化アルミニウム（Ａｌ２Ｏ３）混合物、インジウム、リチウム／アルミニウム混合物、希土類金属などが挙げられる。これらの中で、電子注入性及び酸化などに対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えばマグネシウム／銀混合物、マグネシウム／アルミニウム混合物、マグネシウム／インジウム混合物、アルミニウム／酸化アルミニウム（Ａｌ２Ｏ３）混合物、リチウム／アルミニウム混合物などが好適である。上記陰極は、これらの電極物質を蒸着やスパッタリングなどの方法で薄膜を形成させることにより作製することができる。 On the other hand, as the cathode, those using an electrode substance of a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof are preferably used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this from the viewpoint of durability against electron injecting and oxidation, for example, a magnesium / silver mixture, magnesium An aluminum / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, and the like are preferable. The cathode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering.
　前記の様に、適当な基板上に所望の電極用物質、例えば陽極用物質からなる薄膜を１μｍ以下、好ましくは１０～２００ｎｍの範囲の膜厚になるように、蒸着やスパッタリングなどの方法により形成させて陽極を作製した後、該陽極上に前記の通り正孔注入層、正孔輸送層、発光層、電子輸送層／電子注入層からなる各層薄膜を形成させた後、その上に陰極用物質からなる薄膜を１μｍ以下、好ましくは５０～２００ｎｍの範囲の膜厚になるように、例えば蒸着やスパッタリングなどの方法により形成させて陰極を設け、所望の有機電界発光素子が得られる。 As described above, a thin film made of a desired electrode material, for example, an anode material, is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably in the range of 10 to 200 nm. After preparing the anode, after forming each layer thin film consisting of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer / electron injection layer on the anode as described above, for the cathode A thin film made of a substance is formed by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably in the range of 50 to 200 nm, and a cathode is provided to obtain a desired organic electroluminescence device.
　本発明の有機電界発光素子は、照明用や露光光源のような一種のランプとして使用してもよいし、画像を投影するタイプのプロジェクション装置や、静止画像や動画像を直接視認するタイプの表示装置（ディスプレイ）として使用してもよい。動画再生用の表示装置として使用する場合の駆動方式は単純マトリクス（パッシブマトリクス）方式でもアクティブマトリクス方式でもどちらでもよい。又、異なる発光色を有する本発明の有機電界発光素子を２種以上使用することにより、フルカラー表示装置を作製することが可能である。 The organic electroluminescence device of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display). When used as a display device for reproducing moving images, the driving method may be either a simple matrix (passive matrix) method or an active matrix method. Moreover, it is possible to produce a full-color display device by using two or more organic electroluminescent elements of the present invention having different emission colors.
実施例で作製する単層素子の断面図である。It is sectional drawing of the single layer element produced in the Example.
　１．ＩＴＯ透明電極付きガラス基板
　２．正孔注入層
　３．電荷発生層
　４．正孔輸送層
　５．発光層
　６．電子輸送層
　７．陰極層
　次に、本発明の製造方法について説明する。 1. 1. Glass substrate with ITO transparent electrode 2. hole injection layer Charge generation layer 4. 4. Hole transport layer Light emitting layer 6. 6. Electron transport layer Next, the production method of the present invention will be described.
　本発明のトリアジン化合物（１）は、塩基の存在下又は非存在下に、パラジウム触媒の存在下で、次の反応式（１） The triazine compound (1) of the present invention has the following reaction formula (1) in the presence or absence of a base and in the presence of a palladium catalyst.
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000042
（反応式（１）中、Ａｒ１、Ａｒ２、Ａｒ３、Ｚ１、及びＺ２は、前記と同じ置換基を表す。Ｙは後述する脱離基を表す。Ｍ１及びＭ２は後述する置換基を表す。）、
反応式（２） (In the reaction formula (1), Ar 1 , Ar 2 , Ar 3 , Z 1 , and Z 2 represent the same substituents as described above. Y represents a leaving group to be described later. M 1 and M 2 are described later. Represents a substituent to be
Reaction formula (2)
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000043
（反応式（２）中、Ａｒ１、Ａｒ２、Ａｒ３、Ｚ１、及びＺ２は、前記と同じ置換基を表す。Ｙ１及びＹ２は後述する脱離基を表す。Ｍは後述する置換基を表す。）
で示される方法により製造することができる。 (In the reaction formula (2), Ar 1 , Ar 2 , Ar 3 , Z 1 , and Z 2 represent the same substituents as described above. Y 1 and Y 2 represent a leaving group described later. Represents a substituent.
It can manufacture by the method shown by these.
　また、以降、一般式（２）で表される化合物については化合物（２）と称する。なお、化合物（３）～化合物（５）についても同義とする。以下、これらの化合物の定義について説明する。 Hereinafter, the compound represented by the general formula (2) is referred to as a compound (2). The same applies to compounds (3) to (5). Hereinafter, the definition of these compounds will be described.
　Ｙは脱離基を表し、特に限定するものではないが、例えば塩素原子、臭素原子、ヨウ素原子又はトリフラート等が挙げられる。このうち、反応収率がよい点で臭素原子又は塩素原子が好ましい。但し、原料の入手性からトリフラートを用いた方が好ましい場合もある。 Y represents a leaving group and is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, an iodine atom, and a triflate. Among these, a bromine atom or a chlorine atom is preferable in terms of a good reaction yield. However, it may be preferable to use triflate because of the availability of raw materials.
　また、Ｙ１及びＹ２については、Ｙ１又はＹ２の何れか一方がＹと同義であり、もう一方は水素原子を表す。 As for Y 1 and Y 2, one of Y 1 or Y 2 is the same meaning as Y, the other represents a hydrogen atom.
　Ｍは、各々独立して、ＺｎＲ１、ＭｇＲ２、Ｓｎ（Ｒ３）３又はＢ（ＯＲ４）２を表す。但し、Ｒ１及びＲ２は、各々独立に塩素原子、臭素原子又はヨウ素原子を表し、Ｒ３は、炭素数１から４のアルキル基又はフェニル基を表し、Ｒ４は水素原子、炭素数１から４のアルキル基又はフェニル基を表し、Ｂ（ＯＲ４）２の２つのＲ４は同一又は異なっていてもよい。また、２つのＲ４は一体となって酸素原子及びホウ素原子を含んで環を形成することもできる。 Each M independently represents ZnR 1 , MgR 2 , Sn (R 3 ) 3 or B (OR 4 ) 2 . However, R < 1 > and R < 2 > represents a chlorine atom, a bromine atom, or an iodine atom each independently, R < 3 > represents a C1-C4 alkyl group or a phenyl group, R < 4 > is a hydrogen atom, carbon number 1 It represents an alkyl group or a phenyl group 4, B (oR 4) 2 two R 4 2 may be the same or different. Further, two R 4 may form a ring containing an oxygen atom and a boron atom together.
　ＺｎＲ１、ＭｇＲ２としては、ＺｎＣｌ、ＺｎＢｒ、ＺｎＩ、ＭｇＣｌ、ＭｇＢｒ、ＭｇＩ等が例示できる。 Examples of ZnR 1 and MgR 2 include ZnCl, ZnBr, ZnI, MgCl, MgBr, and MgI.
　Ｓｎ（Ｒ３）３としては、Ｓｎ（Ｍｅ）３、Ｓｎ（Ｂｕ）３等が例示できる。 Examples of Sn (R 3 ) 3 include Sn (Me) 3 and Sn (Bu) 3 .
　Ｂ（ＯＲ４）２としては、Ｂ（ＯＨ）２、Ｂ（ＯＭｅ）２、Ｂ（ＯｉＰｒ）２、Ｂ（ＯＢｕ）２等が例示できる。また、２つのＲ４が一体となって酸素原子及びホウ素原子を含んで環を形成した場合のＢ（ＯＲ４）２の例としては、次の（Ｃ－１）から（Ｃ－６）で示される基が例示でき、収率がよい点で（Ｃ－２）で示される基が望ましい。 Examples of B (OR 4 ) 2 include B (OH) 2 , B (OMe) 2 , B (O i Pr) 2 , and B (OBu) 2 . Examples of B (OR 4 ) 2 in the case where two R 4 are combined to form a ring containing an oxygen atom and a boron atom include the following (C-1) to (C-6): The group shown can be exemplified, and the group shown by (C-2) is desirable from the viewpoint of good yield.
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000044
　また、Ｍ１及びＭ２については、Ｍ１又はＭ２の何れか一方が前記Ｍと同義であり、もう一方は水素原子を表す。 As for the M 1 and M 2, one of the M 1 or M 2 is the same as defined above M, the other represents a hydrogen atom.
　反応式（１）で用いられる化合物（３）は、例えば、特開２００５－２６８１９９号報［０１０５］～［０１２１］、特開２００８－２８０３３０号公報［００６１］～［００７６］又は特開２００１－３３５５１６号公報［００４７］～［００８２］に開示されている方法を組み合わせて製造することができる。化合物（３）としては、次の（Ｂ－１）から（Ｂ－５６）を例示できるが、本発明はこれらに限定されるものではない。 The compound (3) used in the reaction formula (1) is, for example, disclosed in JP-A-2005-268199, [0105] to [0121], JP-A-2008-280330, [0061] to [0076], or JP-A-2001-2001. It can be produced by combining the methods disclosed in Japanese Patent No. 335516 [0047] to [0082]. Examples of the compound (3) include the following (B-1) to (B-56), but the present invention is not limited to these.
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000050
　反応式（２）で用いられる、化合物（５）は、前記化合物（３）のＭ１及びＭ２を、それぞれ、Ｙ１及びＹ２に置き換えた化合物を表す。化合物（５）の具体例としては、上記の（Ｂ－１）から（Ｂ－５６）において、ＭをＹに置き換えたものを例示できるが、本発明はこれらに限定されるものではない。なお、当該Ｍ１、Ｍ２、Ｙ１、Ｙ２、Ｍ、及びＹの定義については、前述の通りである。
を例示することができる。 The compound (5) used in the reaction formula (2) represents a compound in which M 1 and M 2 of the compound (3) are replaced with Y 1 and Y 2 , respectively. Specific examples of the compound (5) include those in which M is replaced with Y in the above (B-1) to (B-56), but the present invention is not limited thereto. The definitions of M 1 , M 2 , Y 1 , Y 2 , M, and Y are as described above.
Can be illustrated.
　続いて、反応式（１）について説明する。「工程１」は化合物（２）を、塩基の存在下又は非存在下に、パラジウム触媒の存在下に、化合物（３）と反応させ、本発明のトリアジン化合物（１）を得る方法であり、鈴木－宮浦反応、根岸反応、玉尾－熊田反応、スティレ反応等の、一般的なカップリング反応の反応条件を適用することにより、収率よく目的物を得ることができる。 Subsequently, the reaction formula (1) will be described. “Step 1” is a method in which the compound (2) is reacted with the compound (3) in the presence or absence of a base in the presence of a palladium catalyst to obtain the triazine compound (1) of the present invention. By applying reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the target product can be obtained in high yield.
　「工程１」で用いることのできるパラジウム触媒としては、塩化パラジウム、酢酸パラジウム、トリフルオロ酢酸パラジウム、硝酸パラジウム等の塩を例示することができる。さらに、π－アリルパラジウムクロリドダイマー、パラジウムアセチルアセトナト、トリス（ジベンジリデンアセトン）ジパラジウム、ジクロロビス（トリフェニルホスフィン）パラジウム、テトラキス（トリフェニルホスフィン）パラジウム及びジクロロ（１，１’－ビス（ジフェニルホスフィノ）フェロセン）パラジウム等の錯化合物を例示することができる。中でも、第三級ホスフィンを配位子として有するパラジウム錯体は反応収率がよい点でさらに好ましく、入手容易であり、反応収率がよい点で、トリフェニルホスフィンを配位子として有するパラジウム錯体が特に好ましい。 Examples of the palladium catalyst that can be used in “Step 1” include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, and the like. Furthermore, π-allyl palladium chloride dimer, palladium acetylacetonate, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro (1,1′-bis (diphenylphosphine). Examples include complex compounds such as fino) ferrocene) palladium. Among these, a palladium complex having a tertiary phosphine as a ligand is more preferable in terms of a good reaction yield, is easily available, and a palladium complex having triphenylphosphine as a ligand is preferable in terms of a good reaction yield. Particularly preferred.
　第三級ホスフィンを配位子として有するパラジウム錯体は、パラジウム塩又は錯化合物に第三級ホスフィンを添加し、反応系中で調製することもできる。この際用いることのできる第三級ホスフィンとしては、トリフェニルホスフィン、トリメチルホスフィン、トリブチルホスフィン、トリ（ｔｅｒｔ－ブチル）ホスフィン、トリシクロヘキシルホスフィン、ｔｅｒｔ－ブチルジフェニルホスフィン、９，９－ジメチル－４，５－ビス（ジフェニルホスフィノ）キサンテン、２－（ジフェニルホスフィノ）－２’－（Ｎ，Ｎ－ジメチルアミノ）ビフェニル、２－（ジ－ｔｅｒｔ－ブチルホスフィノ）ビフェニル、２－（ジシクロヘキシルホスフィノ）ビフェニル、ビス（ジフェニルホスフィノ）メタン、１，２－ビス（ジフェニルホスフィノ）エタン、１，３－ビス（ジフェニルホスフィノ）プロパン、１，４－ビス（ジフェニルホスフィノ）ブタン、１，１’－ビス（ジフェニルホスフィノ）フェロセン、トリ（２－フリル）ホスフィン、トリ（ｏ－トリル）ホスフィン、トリス（２，５－キシリル）ホスフィン、（±）－２，２’－ビス（ジフェニルホスフィノ）－１，１’－ビナフチル、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル等が例示できる。入手容易であり、反応収率がよい点で、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル又はトリフェニルホスフィンが好ましい。第三級ホスフィンとパラジウム塩又は錯化合物とのモル比は、１：１０～１０：１が好ましく、反応収率がよい点で１：２～５：１がさらに好ましい。 The palladium complex having tertiary phosphine as a ligand can also be prepared in a reaction system by adding tertiary phosphine to a palladium salt or complex compound. The tertiary phosphine that can be used at this time is triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5. -Bis (diphenylphosphino) xanthene, 2- (diphenylphosphino) -2 '-(N, N-dimethylamino) biphenyl, 2- (di-tert-butylphosphino) biphenyl, 2- (dicyclohexylphosphino) Biphenyl, bis (diphenylphosphino) methane, 1,2-bis (diphenylphosphino) ethane, 1,3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1 ′ -Bis (diphenylphosphino) Erocene, tri (2-furyl) phosphine, tri (o-tolyl) phosphine, tris (2,5-xylyl) phosphine, (±) -2,2′-bis (diphenylphosphino) -1,1′-binaphthyl And 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl. 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferable because it is easily available and the reaction yield is good. The molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 from the viewpoint of good reaction yield.
　「工程１」で用いることのできる塩基としては、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸リチウム、炭酸セシウム、リン酸カリウム、リン酸ナトリウム、フッ化ナトリウム、フッ化カリウム、フッ化セシウム等を例示することができ、収率がよい点で炭酸カリウムが望ましい。塩基と化合物（３）とのモル比は、１：２から１０：１が望ましく、収率がよい点で１：１から３：１がさらに望ましい。 Bases that can be used in “Step 1” include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, fluorine. Examples thereof include cesium chloride, and potassium carbonate is preferable in terms of a good yield. The molar ratio of base to compound (3) is preferably from 1: 2 to 10: 1, and more preferably from 1: 1 to 3: 1 in terms of good yield.
　「工程１」で用いる化合物（２）と化合物（３）とのモル比は、１：２から５：１が望ましく、収率がよい点で１：２から２：１がさらに望ましい。 The molar ratio of the compound (2) and the compound (3) used in “Step 1” is preferably 1: 2 to 5: 1, and more preferably 1: 2 to 2: 1 in terms of a good yield.
　「工程１」で用いることのできる溶媒として、水、ジメチルスルホキシド、ジメチルホルムアミド、テトラヒドロフラン、１，４－ジオキサン、ジメトキシエタン、トルエン、ベンゼン、ジエチルエーテル、エタノール、メタノール又はキシレン等が例示でき、これらを適宜組み合わせて用いてもよい。収率がよい点でジオキサン又はテトラヒドロフランと水の混合溶媒を用いることが望ましい。 Examples of the solvent that can be used in “Step 1” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene. You may use it combining suitably. It is desirable to use a mixed solvent of dioxane or tetrahydrofuran and water in terms of a good yield.
　「工程１」は、０℃から１５０℃から適宜選ばれた温度で実施することができ、収率がよい点で５０℃から１００℃で行うことがさらに望ましい。 “Step 1” can be carried out at a temperature appropriately selected from 0 ° C. to 150 ° C., and more preferably at 50 ° C. to 100 ° C. in terms of a good yield.
　化合物（１）は、「工程１」の終了後に通常の処理をすることで得られる。必要に応じて、再結晶、カラムクロマトグラフィー又は昇華等で精製してもよい。
「工程２」は化合物（４）を、塩基の存在下又は非存在下に、パラジウム触媒の存在下に、化合物（５）と反応させ、本発明のトリアジン化合物（１）を得る方法であり、鈴木－宮浦反応、根岸反応、玉尾－熊田反応、スティレ反応等の、一般的なカップリング反応の反応条件を適用することにより、収率よく目的物を得ることができる。「工程２」は「工程１」で挙げた条件のうち、化合物（２）を化合物（５）及び化合物（３）を化合物（４）に置き換えた条件を適用することができる。但し、「工程１」と同じ反応条件である必要はない。「工程２」の終了後、必要に応じて、再結晶、カラムクロマトグラフィー又は昇華等で精製してもよい。 Compound (1) can be obtained by carrying out a normal treatment after completion of “Step 1”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.
"Step 2" is a method in which compound (4) is reacted with compound (5) in the presence or absence of a base in the presence of a palladium catalyst to obtain triazine compound (1) of the present invention. By applying reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the target product can be obtained in high yield. Of the conditions listed in “Step 1,” “Step 2” can be applied by replacing Compound (2) with Compound (5) and Compound (3) with Compound (4). However, the reaction conditions are not necessarily the same as those in “Step 1”. After completion of “Step 2”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
　本発明のトリアジン化合物（１）は、有機電界発光素子用材料として好適に用いられるものである。 The triazine compound (1) of the present invention is suitably used as a material for an organic electroluminescence device.
　さらに、本発明のトリアジン化合物（１）は、有機電界発光素子用の電子輸送材料又は電子注入材料として好適に用いられるものである。 Furthermore, the triazine compound (1) of the present invention is suitably used as an electron transport material or an electron injection material for an organic electroluminescence device.
　本発明のトリアジン化合物（１）は有機電界発光素子の構成成分の一部として用いた時に有効である。特に、電子輸送層として用いた時に、従来の素子よりも長寿命化、高効率化及び低電圧化等の効果が得られる。また、本発明のトリアジン化合物（１）を有機電界発光素子用材料として用いる際、任意の有機金属種、有機化合物又は無機化合物との共蒸着膜として用いることも可能である。 The triazine compound (1) of the present invention is effective when used as a part of the components of the organic electroluminescence device. In particular, when used as an electron transport layer, effects such as longer life, higher efficiency, and lower voltage can be obtained than conventional devices. Moreover, when using the triazine compound (1) of this invention as an organic electroluminescent element material, it is also possible to use it as a co-deposition film | membrane with arbitrary organometallic seeds, an organic compound, or an inorganic compound.
　本発明のトリアジン化合物（１）から成る有機電界発光素子用薄膜の製造方法に特に制限はないが、真空蒸着法による成膜が可能である。真空蒸着法による成膜は、汎用の真空蒸着装置を用いることにより行うことができる。真空蒸着法で膜を形成する際の真空槽の真空度は、有機電界発光素子作製の製造タクトタイムや製造コストを考慮すると、一般的に用いられる拡散ポンプ、タ－ボ分子ポンプ、クライオポンプ等により到達し得る１×１０－２～１×１０－５～１×１０－６Ｐａ程度が好ましく、より好ましくは１×１０－３～１０－６Ｐａである。蒸着速度は、形成する膜の厚さによるが０．００５～１．０ｎｍ／秒が好ましく、より好ましくは０．０１～１ｎｍ／秒である。また、本発明のトリアジン化合物（１）は、クロロホルム、ジクロロメタン、１，２－ジクロロエタン、クロロベンゼン、トルエン、酢酸エチル又は、テトラヒドロフラン－等に対する溶解度が高いため、汎用の装置を用いたスピンコ－ト法、インクジェット法、キャスト法又は、ディップ法等による成膜も可能である。 Although there is no restriction | limiting in particular in the manufacturing method of the thin film for organic electroluminescent elements which consists of a triazine compound (1) of this invention, The film-forming by a vacuum evaporation method is possible. Film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus. The vacuum degree of the vacuum chamber when forming a film by the vacuum evaporation method is determined by taking into account the manufacturing tact time and manufacturing cost of manufacturing the organic electroluminescence device, and commonly used diffusion pumps, turbo molecular pumps, cryopumps, etc. Is preferably about 1 × 10 −2 to 1 × 10 −5 to 1 × 10 −6 Pa, more preferably 1 × 10 −3 to 10 −6 Pa. The deposition rate is preferably 0.005 to 1.0 nm / second, more preferably 0.01 to 1 nm / second, depending on the thickness of the film to be formed. Further, since the triazine compound (1) of the present invention has high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran, or the like, a spin coating method using a general-purpose apparatus, Film formation by an inkjet method, a cast method, a dip method, or the like is also possible.
　本発明の効果がえられる有機電界発光素子の典型的な構造としては、基板、陽極、正孔注入層、正孔輸送層発光層、電子輸送層、及び陰極を含む。 The typical structure of the organic electroluminescent element capable of obtaining the effects of the present invention includes a substrate, an anode, a hole injection layer, a hole transport layer light emitting layer, an electron transport layer, and a cathode.
　有機電界発光素子の陽極及び陰極は、電気的な導体を介して電源に接続されている。陽極と陰極との間に電位を加えることにより、有機電界発光素子は作動する。正孔は陽極から有機電界発光素子内に注入され、そして電子は陰極で有機電界発光素子内に注入される。 The anode and cathode of the organic electroluminescent element are connected to a power source through an electrical conductor. The organic electroluminescent device operates by applying a potential between the anode and the cathode. Holes are injected into the organic electroluminescent device from the anode, and electrons are injected into the organic electroluminescent device at the cathode.
　有機電界発光素子は典型的には基板に被せられ、陽極又は陰極は基板と接触することができる。基板と接触する電極は便宜上、下側電極と呼ばれる。一般的には、下側電極は陽極であるが、本発明の有機電界発光素子においてはそのような形態に限定されるものではない。基板は、意図される発光方向に応じて、光透過性又は不透明であってよい。光透過特性は、基板を通してエレクトロルミネッセンス発光を見るのに望ましい。透明ガラス又はプラスチックがこのような基板として一般に採用される。基板は、多重の材料層を含む複合構造であってよい。 The organic electroluminescent element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate. The electrode in contact with the substrate is called the lower electrode for convenience. Generally, the lower electrode is an anode, but the organic electroluminescence device of the present invention is not limited to such a form. The substrate may be light transmissive or opaque, depending on the intended emission direction. Light transmission properties are desirable for viewing electroluminescent emission through a substrate. Transparent glass or plastic is generally employed as such a substrate. The substrate may be a composite structure including multiple material layers.
　エレクトロルミネッセンス発光が陽極を通して見られる場合、陽極が当該発光を通すか又は実質的に通すべきである。本発明において使用される一般的な透明アノード（陽極）材料は、インジウム－錫酸化物（ＩＴＯ）、インジウム－亜鉛酸化物（ＩＺＯ）、又は酸化錫であるが、しかしその他の金属酸化物、例えばアルミニウム又はインジウム・ドープ型酸化錫、マグネシウム－インジウム酸化物、又はニッケル－タングステン酸化物も役立つ。これらの酸化物に加えて、金属窒化物、例えば窒化ガリウム、金属セレン化物、例えばセレン化亜鉛、又は金属硫化物、例えば硫化亜鉛を陽極として使用することができる。陽極は、プラズマ蒸着されたフルオロカーボンで改質することができる。陰極を通してだけエレクトロルミネッセンス発光が見られる用途の場合、陽極の透過特性は重要ではなく、透明、不透明又は反射性の任意の導電性材料を使用することができる。この用途のための導体の一例としては、金、イリジウム、モリブデン、パラジウム及び白金が挙げられる。 If an electroluminescent emission is seen through the anode, the anode should pass or substantially pass the emission. Common transparent anode (anode) materials used in the present invention are indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide, but other metal oxides such as Aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide are also useful. In addition to these oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode. The anode can be modified with plasma deposited fluorocarbon. For applications where electroluminescent emission is only seen through the cathode, the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium and platinum.
　陽極と正孔輸送層との間に正孔注入層が設けることができる。正孔注入材料は、後続の有機層の膜形成特性を改善し、そして正孔輸送層内に正孔を注入するのを容易にするのに役立つことができる。正孔注入層内で使用するのに適した材料の一例としては、ポルフィリン化合物、プラズマ蒸着型フルオロカーボン・ポリマー、及びビフェニル基、カルバゾール基等芳香環を有するアミン、例えばｍ－ＭＴＤＡＴＡ（４，４’，４’’－トリス［（３－メチルフェニル）フェニルアミノ］トリフェニルアミン）、２Ｔ－ＮＡＴＡ（４，４’，４’’－トリス［（Ｎ－ナフタレン－２－イル）－Ｎ－フェニルアミノ］トリフェニルアミン）、トリフェニルアミン、トリトリルアミン、トリルジフェニルアミン、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ビス（３－メチルフェニル）－１，１’－ビフェニル－４，４’－ジアミン、Ｎ，Ｎ，Ｎ’Ｎ’－テトラキス（４－メチルフェニル）－１，１’－ビフェニル－４，４’－ジアミン、ＭｅＯ－ＴＰＤ（Ｎ，Ｎ，Ｎ’Ｎ’－テトラキス（４－メトキシフェニル）－１，１’－ビフェニル－４，４’－ジアミン）、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジナフチル－１，１’－ビフェニル－４，４’－ジアミン、Ｎ，Ｎ’－ビス（メチルフェニル）－Ｎ，Ｎ’－ビス（４－ノルマルブチルフェニル）フェナントレン－９，１０－ジアミン、又はＮ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ビス（９－フェニルカルバゾール－３－イル）－１，１’－ビフェニル－４，４’－ジアミン等が挙げられる。 A hole injection layer can be provided between the anode and the hole transport layer. The hole injection material can serve to improve the film forming properties of the subsequent organic layer and to facilitate injection of holes into the hole transport layer. Examples of materials suitable for use in the hole injection layer include porphyrin compounds, plasma deposited fluorocarbon polymers, and amines having aromatic rings such as biphenyl groups and carbazole groups, such as m-MTDATA (4,4 ′ , 4 ″ -tris [(3-methylphenyl) phenylamino] triphenylamine), 2T-NATA (4,4 ′, 4 ″ -tris [(N-naphthalen-2-yl) -N-phenylamino ] Triphenylamine), triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N, N′N′-tetrakis (4-methylphenyl) -1,1′-biphenyl-4,4′-diamine, MeO-TPD N, N, N′N′-tetrakis (4-methoxyphenyl) -1,1′-biphenyl-4,4′-diamine), N, N′-diphenyl-N, N′-dinaphthyl-1,1 ′ -Biphenyl-4,4'-diamine, N, N'-bis (methylphenyl) -N, N'-bis (4-normalbutylphenyl) phenanthrene-9,10-diamine, or N, N'-diphenyl- N, N′-bis (9-phenylcarbazol-3-yl) -1,1′-biphenyl-4,4′-diamine and the like can be mentioned.
　有機電界発光素子の正孔輸送層は、１種以上の正孔輸送化合物、例えば芳香族第三アミンを含有することが好ましい。芳香族第三アミンは、１つ以上の三価窒素原子を含有する化合物であることを意味し、この三価窒素原子は炭素原子だけに結合されており、これらの炭素原子の１つ以上が芳香族環を形成している。具体的には、芳香族第三アミンは、アリールアミン、例えばモノアリールアミン、ジアリールアミン、トリアリールアミン、又は高分子アリールアミンであってよい。 The hole transport layer of the organic electroluminescence device preferably contains one or more hole transport compounds such as aromatic tertiary amines. Aromatic tertiary amine means that the compound contains one or more trivalent nitrogen atoms, the trivalent nitrogen atoms being bonded only to carbon atoms, one or more of these carbon atoms being An aromatic ring is formed. Specifically, the aromatic tertiary amine can be an arylamine, such as a monoarylamine, diarylamine, triarylamine, or a polymeric arylamine.
　正孔輸送材料としては、１つ以上のアミン基を有する芳香族第三アミンを使用することができる。さらに、高分子正孔輸送材料を使用することができる。例えばポリ（Ｎ－ビニルカルバゾール）（ＰＶＫ）、ポリチオフェン、ポリピロール、又はポリアニリン等を使用することができる。例えば、ＮＰＤ（Ｎ，Ｎ’－ビス（ナフタレン－１－イル）－Ｎ，Ｎ’－ジフェニル－１，１’－ビフェニル－４，４’－ジアミン）、α－ＮＰＤ（Ｎ，Ｎ’－ジ（１－ナフチル）－Ｎ，Ｎ’－ジフェニル－１，１’－ビフェニル－４，４’　－ジアミン）、ＴＰＢｉ（１，３，５－トリス（１－フェニル－１Ｈ－ベンズイミダゾール－２－イル）ベンゼン）、又はＴＰＤ（Ｎ，Ｎ’－ビス（３－メチルフェニル）　－Ｎ，Ｎ’－ジフェニル－１，１’－ビフェニル－４，４’－ジアミン）等が挙げられる。 As the hole transport material, an aromatic tertiary amine having one or more amine groups can be used. Furthermore, a polymeric hole transport material can be used. For example, poly (N-vinylcarbazole) (PVK), polythiophene, polypyrrole, or polyaniline can be used. For example, NPD (N, N′-bis (naphthalen-1-yl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine), α-NPD (N, N′-di) (1-naphthyl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine), TPBi (1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) ) Benzene), or TPD (N, N′-bis (3-methylphenyl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine).
　正孔注入層と正孔輸送層の間に、電荷発生層としてジピラジノ［２，３－ｆ：２’，３’－ｈ］キノキサリン－２，３，６，７，１０，１１－ヘキサカルボニトリル（ＨＡＴ－ＣＮ）を含む層を設けてもよい。 Dipyrazino [2,3-f: 2 ′, 3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile as a charge generation layer between the hole injection layer and the hole transport layer A layer containing (HAT-CN) may be provided.
　有機電界発光素子の発光層は、燐光材料又は蛍光材料を含み、この場合、この領域で電子・正孔対が再結合された結果として発光を生じる。発光層は、低分子及びポリマー双方を含む単一材料から成っていてよいが、しかし、より一般的には、ゲスト化合物でドーピングされたホスト材料から成っており、この場合、発光は主としてドーパントから生じ、そして任意の色を有することができる。 The light emitting layer of the organic electroluminescent element contains a phosphorescent material or a fluorescent material. In this case, light emission occurs as a result of recombination of electron-hole pairs in this region. The emissive layer may consist of a single material including both small molecules and polymers, but more commonly consists of a host material doped with a guest compound, in which case the emission is mainly from the dopant. Occurs and can have any color.
　発光層のホスト材料としては、例えば、ビフェニル基、フルオレニル基、トリフェニルシリル基、カルバゾール基、ピレニル基、又はアントリル基を有する化合物が挙げられる。例えば、ＤＰＶＢｉ（４，４’－ビス（２，２－ジフェニルビニル）－１，１’－ビフェニル）、ＢＣｚＶＢｉ（４，４’－ビス（９－エチル－３－カルバゾビニレン）１，１’－ビフェニル）、ＴＢＡＤＮ（２－ターシャルブチル－９，１０－ジ（２－ナフチル）アントラセン）、ＡＤＮ（９，１０－ジ（２－ナフチル）アントラセン）、ＣＢＰ（４，４’－ビス（カルバゾール－９－イル）ビフェニル）、ＣＤＢＰ（４，４’－ビス（カルバゾール－９－イル）－２，２’－ジメチルビフェニル）、又は９，１０－ビス（ビフェニル）アントラセン等が挙げられる。 Examples of the host material for the light emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthryl group. For example, DPVBi (4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl), BCzVBi (4,4′-bis (9-ethyl-3-carbazovinylene) 1,1′-biphenyl ), TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene), ADN (9,10-di (2-naphthyl) anthracene), CBP (4,4′-bis (carbazole-9) -Yl) biphenyl), CDBP (4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl), 9,10-bis (biphenyl) anthracene and the like.
　発光層内のホスト材料は、下記に定義する電子輸送材料、上記に定義する正孔輸送材料、又は正孔・電子再結合をサポートする別の材料又はこれら材料の組み合わせであってよい。 The host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as defined above, or another material that supports hole-electron recombination, or a combination of these materials.
　有用な蛍光ドーパントの一例としては、アントラセン、テトラセン、キサンテン、ペリレン、ルブレン、クマリン、ローダミン及びキナクリドン、ジシアノメチレンピラン化合物、チオピラン化合物、ポリメチン化合物、ピリリウム、又はチアピリリウム化合物、フルオレン誘導体、ペリフランテン誘導体、インデノペリレン誘導体、ビス（アジニル）アミンホウ素化合物、ビス（アジニル）メタン化合物、及びカルボスチリル化合物等が挙げられる。 Examples of useful fluorescent dopants include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine and quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium or thiapyrylium compounds, fluorene derivatives, perifanthene derivatives, indeno Examples include perylene derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
　有用な燐光ドーパントの一例としては、イリジウム、白金、パラジウム又はオスミウムの遷移金属の有機金属錯体が挙げられる。 An example of a useful phosphorescent dopant is an organometallic complex of a transition metal of iridium, platinum, palladium, or osmium.
　ドーパントの一例として、Ａｌｑ３（トリス（８－ヒドロキシキノリン）アルミニウム））、ＤＰＡＶＢｉ（４，４’－ビス［４－（ジ－パラ－トリルアミノ）スチリル］　ビフェニル）、ペリレン、Ｉｒ（ＰＰｙ）３（トリス（２－フェニルピリジン）イリジウム（ＩＩＩ）、又はＦｌｒＰｉｃ（ビス（３，５－ジフルオロ－２－（２－ピリジル）フェニル－（２－カルボキシピリジル）イリジウム（ＩＩＩ）等が挙げられる。 Examples of dopants include Alq 3 (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) 3 ( And tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.
　本発明の有機電界発光素子の電子輸送層を形成するのに使用する薄膜形成材料は、本発明のトリアジン化合物（１）である。なお、当該電子輸送層には、他の電子輸送性材料を含んでいても良く、当該電子輸送性材料としては、アルカリ金属錯体、アルカリ土類金属錯体、土類金属錯体等が挙げられる。望ましいアルカリ金属錯体、アルカリ土類金属錯体、土類金属錯体としては、例えば、８－ヒドロキシキノリナートリチウム（Ｌｉｑ）、ビス（８－ヒドロキシキノリナート）亜鉛、ビス（８－ヒドロキシキノリナート）銅、ビス（８－ヒドロキシキノリナート）マンガン、トリス（８－ヒドロキシキノリナート）アルミニウム、トリス（２－メチル－８－ヒドロキシキノリナート）アルミニウム、トリス（８－ヒドロキシキノリナート）ガリウム、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナート）亜鉛、ビス（２－メチル－８－キノリナート）クロロガリウム、ビス（２－メチル－８－キノリナート）（ｏ－クレゾラート）ガリウム、ビス（２－メチル－８－キノリナート）－１－ナフトラートアルミニウム、又はビス（２－メチル－８－キノリナート）－２－ナフトラートガリウム等が挙げられる。 The thin film forming material used for forming the electron transport layer of the organic electroluminescence device of the present invention is the triazine compound (1) of the present invention. Note that the electron transporting layer may contain another electron transporting material, and examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Desirable alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include, for example, 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate). Copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, Bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-Crezolate) gallium, bis (2-methyl-8-quinolina) G) -1-naphthoquinone Trad aluminum or bis (2-methyl-8-quinolinato) -2-naphthoquinone Trad gallium, and the like.
　発光層と電子輸送層との間に、キャリアバランスを改善させる目的で、正孔阻止層を設けてもよい。正孔阻止層として望ましい化合物は、ＢＣＰ（２，９－ジメチル－４，７－ジフェニル－１，１０－フェナントロリン）、Ｂｐｈｅｎ（４，７－ジフェニル－１，１０－フェナントロリン）、ＢＡｌｑ（ビス（２－メチル－８－キノリノラート）－４－（フェニルフェノラート）アルミニウム）、又はビス（１０－ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム）等が挙げられる。 A hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance. Preferred compounds for the hole blocking layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).
　本発明の有機電界発光素子においては、電子注入性を向上させ、素子特性（例えば、発光効率、低電圧駆動、又は高耐久性）を向上させる目的で、電子注入層を設けてもよい。 In the organic electroluminescent device of the present invention, an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, light emission efficiency, low voltage driving, or high durability).
　電子注入層として望ましい化合物としては、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、又はアントロン等が挙げられる。また、上記に記した金属錯体やアルカリ金属酸化物、アルカリ土類酸化物、希土類酸化物、アルカリ金属ハロゲン化物、アルカリ土類ハロゲン化物、希土類ハロゲン化物、ＳｉＯＸ、ＡｌＯＸ、ＳｉＮＸ、ＳｉＯＮ、ＡｌＯＮ、ＧｅＯＸ、ＬｉＯＸ、ＬｉＯＮ、ＴｉＯＸ、ＴｉＯＮ、ＴａＯＸ、ＴａＯＮ、ＴａＮＸ、Ｃなど各種酸化物、窒化物、及び酸化窒化物のような無機化合物も使用できる。 Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, or anthrone. Etc. In addition, the metal complexes, alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO x , AlO x , SiN x , SiON, Inorganic compounds such as various oxides such as AlON, GeO X , LiO X , LiON, TiO X , TiON, TaO X , TaON, TaN X , and C, nitrides, and oxynitrides can also be used.
　発光が陽極を通してのみ見られる場合、本発明において使用される陰極は、ほぼ任意の導電性材料から形成することができる。望ましい陰極材料としては、ナトリウム、ナトリウム－カリウム合金、マグネシウム、リチウム、マグネシウム／銅混合物、マグネシウム／銀混合物、マグネシウム／アルミニウム混合物、マグネシウム／インジウム混合物、アルミニウム／酸化アルミニウム（Ａｌ２Ｏ３）混合物、インジウム、リチウム／アルミニウム混合物、希土類金属等が挙げられる。 If light emission is seen only through the anode, the cathode used in the present invention can be formed from almost any conductive material. Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
　以下、本発明を実施例に基づきさらに詳細に説明するが、本発明はこれら実施例により何ら限定して解釈されるものではない。 Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not construed as being limited to these examples.
　１Ｈ－ＮＭＲ測定は、Ｇｅｍｉｎｉ２００（バリアン社製）を用いて行った。 1 H-NMR measurement was performed using Gemini 200 (manufactured by Varian).
　有機電界発光素子の発光特性は、室温下、作製した素子に直流電流を印加し、ＬＵＭＩＮＡＮＣＥＭＥＴＥＲ（ＢＭ－９）（ＴＯＰＣＯＮ社製）の輝度計を用いて評価した。 The light emission characteristics of the organic electroluminescence device were evaluated by applying a direct current to the fabricated device at room temperature and using a luminance meter of LUMINANCE METER (BM-9) (TOPCON).
　実施例－１ Example-1
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
　アルゴン気流下、３－（４，６－ジフェニルピリジン－２－イル）フェニルボロン酸（１．０９ｇ，３．０９ｍｍｏｌ）、２－（３－ブロモフェニル）－４，６－ジフェニル－１，３，５－トリアジン（１．００ｇ，２．５８ｍｍｏｌ）、及びテトラキス（トリフェニルホスフィン）パラジウム（９６ｍｇ，０．０７７ｍｍｏｌ）をテトラヒドロフラン（５０ｍＬ）に懸濁した。これに、２Ｍの炭酸カリウム水溶液（４．０ｍＬ，８．００ｍｍｏｌ）を加え、７５℃で３１時間撹拌した。室温まで放冷後、反応溶液を減圧濃縮した。得られたスラリーに水（５０ｍＬ）、メタノール（５０ｍＬ）、テトラヒドロフラン（１０ｍＬ）、ヘキサン（５０ｍＬ）を加え、７５℃で撹拌し、析出した固体を濾別した。得られた固体を水（５０ｍＬ）、メタノール（５０ｍＬ）、ヘキサン（５０ｍＬ）で洗浄した。この固体を酢酸エチル（２００ｍＬ）に溶解し、セライトろ過し、ろ液を減圧濃縮した。この濃縮液が乾固して得られた固体を再結晶（酢酸エチル）で精製することで、目的の４，６－ジフェニル－２－［３’－（４，６－ジフェニルピリジン－２－イル）－ビフェニル－３－イル］－１，３，５－トリアジン（化合物Ａ－１）の白色固体（収量０．９５ｇ，収率６０％）を得た。 Under an argon stream, 3- (4,6-diphenylpyridin-2-yl) phenylboronic acid (1.09 g, 3.09 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3, 5-Triazine (1.00 g, 2.58 mmol) and tetrakis (triphenylphosphine) palladium (96 mg, 0.077 mmol) were suspended in tetrahydrofuran (50 mL). To this was added 2M aqueous potassium carbonate solution (4.0 mL, 8.00 mmol), and the mixture was stirred at 75 ° C. for 31 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 mL), methanol (50 mL), tetrahydrofuran (10 mL) and hexane (50 mL) were added to the resulting slurry, and the mixture was stirred at 75 ° C., and the precipitated solid was separated by filtration. The obtained solid was washed with water (50 mL), methanol (50 mL), and hexane (50 mL). This solid was dissolved in ethyl acetate (200 mL), filtered through celite, and the filtrate was concentrated under reduced pressure. The solid obtained by drying this concentrated solution was purified by recrystallization (ethyl acetate) to obtain the desired 4,6-diphenyl-2- [3 ′-(4,6-diphenylpyridin-2-yl). ) -Biphenyl-3-yl] -1,3,5-triazine (Compound A-1) was obtained as a white solid (yield 0.95 g, yield 60%).
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３５－７．５７（ｍ，１２Ｈ），７．６３（ｄｄ，Ｊ＝１６，８．０Ｈｚ，２Ｈ），７．７２（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ），７．７７（ｄ，Ｊ＝７．７Ｈｚ，１Ｈ），７．８８－７．９０（ｍ，２Ｈ），７．９４（ｓ，１Ｈ），８．１６－８．２１（ｍ，３Ｈ），８．４８（ｓ，１Ｈ），８．７３－８．７６（ｍ，５Ｈ），９．０４（ｓ，１Ｈ）．
　実施例－２ 1 H-NMR (CDCl 3 ) δ (ppm): 7.35-7.57 (m, 12H), 7.63 (dd, J = 16, 8.0 Hz, 2H), 7.72 (d, J = 7.6 Hz, 2H), 7.77 (d, J = 7.7 Hz, 1H), 7.88-7.90 (m, 2H), 7.94 (s, 1H), 8.16-8 .21 (m, 3H), 8.48 (s, 1H), 8.73-8.76 (m, 5H), 9.04 (s, 1H).
Example-2
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000052
　アルゴン気流下、２－（２－ブロモフェニル）－４，６－ジフェニルピリジン（１．００ｇ，２．５９ｍｍｏｌ）、２－［３－｛（４，４，５，５－テトラメチル－１，３，２－ジオキサボロラン－２－イル）フェニル｝］－４，６－ジフェニル－１，３，５－トリアジン（１．４７ｇ，３．３８ｍｍｏｌ）、及びテトラキス（トリフェニルホスフィン）パラジウム（０．１２１ｇ，０．１０５ｍｍｏｌ）をテトラヒドロフラン（２６ｍＬ）に懸濁した。これに、２Ｍの炭酸カリウム水溶液（３．９ｍＬ，７．８０ｍｍｏｌ）を加え、７５℃で４９時間撹拌した。室温まで放冷後、反応溶液を減圧濃縮した。得られた濃縮液にメタノール（３０ｍＬ）、酢酸エチル（５ｍＬ）を加え、７８℃で撹拌し、析出した固体を濾別した。得られた固体を水（３０ｍＬ）、メタノール（３０ｍＬ）、ヘキサン（３０ｍＬ）で洗浄した。この固体を酢酸エチル（２００ｍＬ）に溶解し、活性炭１０ｍｇを加えたのち、セライトろ過し、ろ液を減圧濃縮した。得られた濃縮液にヘキサン（３０ｍＬ）、酢酸エチル（５ｍＬ）を加え、７０℃で撹拌し、析出した固体を濾別した。得られた固体をシリカゲルカラムクロマトグラフィー（クロロホルム：ヘキサン）で精製することで、目的の４，６－ジフェニル－２－［２’－（４，６－ジフェニルピリジン－２－イル）－ビフェニル－３－イル］－１，３，５－トリアジン（化合物Ａ－４２１）の白色固体（収量１．５２ｇ，収率７６％）を得た。 Under an argon stream, 2- (2-bromophenyl) -4,6-diphenylpyridine (1.00 g, 2.59 mmol), 2- [3-{(4,4,5,5-tetramethyl-1,3 , 2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (1.47 g, 3.38 mmol), and tetrakis (triphenylphosphine) palladium (0.121 g, 0 .105 mmol) was suspended in tetrahydrofuran (26 mL). To this was added 2M aqueous potassium carbonate (3.9 mL, 7.80 mmol), and the mixture was stirred at 75 ° C. for 49 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Methanol (30 mL) and ethyl acetate (5 mL) were added to the obtained concentrated liquid, and the mixture was stirred at 78 ° C., and the precipitated solid was separated by filtration. The obtained solid was washed with water (30 mL), methanol (30 mL), and hexane (30 mL). This solid was dissolved in ethyl acetate (200 mL), 10 mg of activated carbon was added, the mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. Hexane (30 mL) and ethyl acetate (5 mL) were added to the obtained concentrated liquid, and the mixture was stirred at 70 ° C., and the precipitated solid was separated by filtration. The obtained solid was purified by silica gel column chromatography (chloroform: hexane) to obtain the desired 4,6-diphenyl-2- [2 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3. A white solid (yield 1.52 g, yield 76%) of -yl] -1,3,5-triazine (Compound A-421) was obtained.
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．２４－７．３４（ｍ，９Ｈ），７．３８（ｔ，Ｊ＝７．３Ｈｚ，４Ｈ），７．４４－７．５４（ｍ，６Ｈ），７．５８（ｍ，１Ｈ），７．６４（ｓ，１Ｈ），７．８１（ｍ，２Ｈ），７．９１（ｍ，１Ｈ），８．６１（ｄ，Ｊ＝８．１Ｈｚ，４Ｈ），８．６３－８．６６（ｍ，１Ｈ），８．６８（ｍ，１Ｈ）．
　実施例－３ 1 H-NMR (CDCl 3 ) δ (ppm): 7.24-7.34 (m, 9H), 7.38 (t, J = 7.3 Hz, 4H), 7.44-7.54 (m 6H), 7.58 (m, 1H), 7.64 (s, 1H), 7.81 (m, 2H), 7.91 (m, 1H), 8.61 (d, J = 8. 1 Hz, 4H), 8.63-8.66 (m, 1H), 8.68 (m, 1H).
Example-3
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
　３－（４，６－ジフェニルピリジン－２－イル）フェニルボロン酸　１．００ｇを３－［４－（４－ジベンゾフリル）－６－フェニルピリジン－２－イル］フェニルボロン酸　１．２６ｇに変更した以外は実施例－１と同様にして、４，６－ジフェニル－２－｛３’－［４－（４－ジベンゾフリル）－６－フェニルピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジン（化合物Ａ－４１）の白色固体（収率６８％）を得た。
得られた化合物のＴｇは１１６℃であった。 Changed 1.00 g of 3- (4,6-diphenylpyridin-2-yl) phenylboronic acid to 1.26 g of 3- [4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] phenylboronic acid 4,6-diphenyl-2- {3 ′-[4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} in the same manner as in Example 1 except that A white solid (68% yield) of -1,3,5-triazine (Compound A-41) was obtained.
The Tg of the obtained compound was 116 ° C.
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３２（ｔ，Ｊ＝７．５Ｈｚ，１Ｈ），７．３７－７．５８（ｍ，１２Ｈ），７．６４（ｔ，Ｊ＝７．９Ｈｚ，２Ｈ），７．７４（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ），７．７９（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ），７．９０（ｄ，Ｊ＝７．７Ｈｚ，１Ｈ），７．９５（ｄ，Ｊ＝７．５Ｈｚ，１Ｈ），７．９９（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ），８．２２－８．２７（ｍ，５Ｈ），８．５４（ｓ，１Ｈ），８．７２－８．７６（ｍ，５Ｈ），９．０５（ｓ，１Ｈ）．
　実施例－４ 1 H-NMR (CDCl 3 ) δ (ppm): 7.32 (t, J = 7.5 Hz, 1H), 7.37-7.58 (m, 12H), 7.64 (t, J = 7 .9 Hz, 2H), 7.74 (d, J = 7.6 Hz, 1H), 7.79 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.7 Hz, 1H) , 7.95 (d, J = 7.5 Hz, 1H), 7.99 (d, J = 7.6 Hz, 1H), 8.22-8.27 (m, 5H), 8.54 (s, 1H), 8.72-8.76 (m, 5H), 9.05 (s, 1H).
Example-4
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000054
　２－（２－ブロモフェニル）－４，６－ジフェニルピリジン　１．００ｇを２－（２－ブロモフェニル）－４－（４－ジベンゾフリル）－６－フェニルピリジン　１．２３ｇに変更した以外は実施例－２と同様にして、４，６－ジフェニル－２－｛２’－［４－（４－ジベンゾフリル）－６－フェニルピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジン（化合物Ａ－４６１）の白色固体（収率７２％）を得た。
１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．２１－７．３６（ｍ，１１Ｈ），７．４２－７．４７（ｍ，４Ｈ），７．５０－７．５６（ｍ，３Ｈ），７．５９－７．６３（ｍ，２Ｈ），７．８１－７．８５（ｍ，４Ｈ），７．９１－７．９６（ｍ，１Ｈ），８．０６（ｓ，１Ｈ），８．５９（ｄ，Ｊ＝６．８Ｈｚ，４Ｈ），８．６３（ｄ，Ｊ＝７．８Ｈｚ，１Ｈ），８．７４（ｓ，１Ｈ）．
　実施例－５ Except that 1.00 g of 2- (2-bromophenyl) -4,6-diphenylpyridine was changed to 1.23 g of 2- (2-bromophenyl) -4- (4-dibenzofuryl) -6-phenylpyridine Similar to Example-2, 4,6-diphenyl-2- {2 '-[4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1,3 , 5-triazine (Compound A-461) was obtained as a white solid (yield 72%).
1 H-NMR (CDCl 3 ) δ (ppm): 7.21-7.36 (m, 11H), 7.42-7.47 (m, 4H), 7.50-7.56 (m, 3H) ), 7.59-7.63 (m, 2H), 7.81-7.85 (m, 4H), 7.91-7.96 (m, 1H), 8.06 (s, 1H), 8.59 (d, J = 6.8 Hz, 4H), 8.63 (d, J = 7.8 Hz, 1H), 8.74 (s, 1H).
Example-5
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000055
　２－（２－ブロモフェニル）－４，６－ジフェニルピリジン１．００ｇを２－（２－ブロモフェニル）－４－（２－ジベンゾフリル）－６－フェニルピリジン１．２３ｇに変更した以外は実施例－２と同様にして、４，６－ジフェニル－２－｛２’－［４－（２－ジベンゾフリル）－６－フェニルピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジン（化合物Ａ－４６７）の白色固体（収率５３％）を得た。
１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．０４（ｔ，Ｊ＝７．６Ｈｚ，１Ｈ），７．２８－７．６３（ｍ，２０Ｈ），７．７２（ｓ，１Ｈ），７．７６（ｄ，Ｊ＝７．８Ｈｚ，１Ｈ），７．９３（ｄ，Ｊ＝６．２Ｈｚ，２Ｈ），７．９９－８．０３（ｍ，１Ｈ），８．６３（ｄ，Ｊ＝６．９Ｈｚ，４Ｈ），８．７７－８．８０（ｍ，２Ｈ）．
　実施例－６ Except that 1.00 g of 2- (2-bromophenyl) -4,6-diphenylpyridine was changed to 1.23 g of 2- (2-bromophenyl) -4- (2-dibenzofuryl) -6-phenylpyridine Similar to Example-2, 4,6-diphenyl-2- {2 '-[4- (2-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1,3 , 5-triazine (Compound A-467) was obtained as a white solid (yield 53%).
1 H-NMR (CDCl 3 ) δ (ppm): 7.04 (t, J = 7.6 Hz, 1H), 7.28-7.63 (m, 20H), 7.72 (s, 1H), 7.76 (d, J = 7.8 Hz, 1H), 7.93 (d, J = 6.2 Hz, 2H), 7.99-8.03 (m, 1H), 8.63 (d, J = 6.9 Hz, 4H), 8.77-8.80 (m, 2H).
Example-6
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000056
　窒素気流下、４－（２－ブロモフェニル）－２－（４－ビフェニル）－６－フェニルピリジン（３．０ｇ，６．４９ｍｍｏｌ）、２－［３－｛（４，４，５，５－テトラメチル－１，３，２－ジオキサボロラン－２－イル）フェニル｝］－４，６－ジフェニル－１，３，５－トリアジン（３．００ｇ，６．４９ｍｍｏｌ）、酢酸パラジウム（２９．１ｍｇ，０．１３０ｍｍｏｌ）及び２－ジシクロヘキシルフォスフィノ－２’，４’，６’－トリイソプロピルビフェニル（１２４ｍｇ、０．２６０ｍｍｏｌ）をトルエン（５０ｍＬ）に懸濁した。これに４．０Ｍの水酸化ナトリウム水溶液（４．８７ｍＬ，１９．５ｍｍｏｌ）を加え、１００℃で４時間撹拌した。室温まで放冷後、反応溶液を減圧濃縮した。得られた濃縮液に水（３０ｍＬ）、メタノール（６０ｍＬ）を加え、析出した固体を濾別した。得られた固体をシリカゲルカラムクロマトグラフィー（クロロホルム／ヘキサン）で精製することで、目的の２－｛２’－［２－（４－ビフェニル）－６－フェニルピリジン－４－イル］－ビフェニル－３－イル｝－４，６－ジフェニル－１，３，５－トリアジン（化合物Ａ－７５４）の白色固体（収量４．１４ｇ，収率９２％）を得た。
１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３３－７．６８（ｍ，２４Ｈ），７．９６（ｄ，Ｊ＝７．８Ｈｚ，２Ｈ），８．０１（ｄ，Ｊ＝８．４Ｈｚ，２Ｈ），８．６９（ｄ，Ｊ＝７．２Ｈｚ，５Ｈ），８．７８（ｓ，１Ｈ）．
　実施例－７ Under nitrogen flow, 4- (2-bromophenyl) -2- (4-biphenyl) -6-phenylpyridine (3.0 g, 6.49 mmol), 2- [3-{(4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (3.00 g, 6.49 mmol), palladium acetate (29.1 mg, 0 .130 mmol) and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (124 mg, 0.260 mmol) were suspended in toluene (50 mL). To this, 4.0 M aqueous sodium hydroxide solution (4.87 mL, 19.5 mmol) was added and stirred at 100 ° C. for 4 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (30 mL) and methanol (60 mL) were added to the obtained concentrated liquid, and the precipitated solid was separated by filtration. The obtained solid was purified by silica gel column chromatography (chloroform / hexane) to give the desired 2- {2 '-[2- (4-biphenyl) -6-phenylpyridin-4-yl] -biphenyl-3. A white solid (yield 4.14 g, yield 92%) of -yl} -4,6-diphenyl-1,3,5-triazine (Compound A-754) was obtained.
1 H-NMR (CDCl 3 ) δ (ppm): 7.33-7.68 (m, 24H), 7.96 (d, J = 7.8 Hz, 2H), 8.01 (d, J = 8 .4 Hz, 2H), 8.69 (d, J = 7.2 Hz, 5H), 8.78 (s, 1H).
Example-7
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000057
　窒素気流下、４－（３－ブロモフェニル）－２－（４－ビフェニル）－６－フェニルピリジン（３．０ｇ，６．４９ｍｍｏｌ）、２－［３－｛（４，４，５，５－テトラメチル－１，３，２－ジオキサボロラン－２－イル）フェニル｝］－４，６－ジフェニル－１，３，５－トリアジン（３．００ｇ，６．４９ｍｍｏｌ）、酢酸パラジウム（２９．１ｍｇ，０．１３０ｍｍｏｌ）及び２－ジシクロヘキシルフォスフィノ－２’，４’，６’－トリイソプロピルビフェニル（１２４ｍｇ、０．２６０ｍｍｏｌ）をトルエン（５０ｍＬ）に懸濁した。これに４．０Ｍの水酸化ナトリウム水溶液（４．８７ｍＬ，１９．５ｍｍｏｌ）を加え、１００℃で２時間撹拌した。室温まで放冷後、反応溶液を減圧濃縮した。得られた濃縮液に水（３０ｍＬ）、メタノール（６０ｍＬ）を加え、析出した固体を濾別した。得られた固体をシリカゲルカラムクロマトグラフィー（クロロホルム／ヘキサン）で精製することで、目的の２－｛３’－［２－（４－ビフェニル）－６－フェニルピリジン－４－イル］－ビフェニル－３－イル｝－４，６－ジフェニル－１，３，５－トリアジン（化合物Ａ－３３４）の白色固体（収量３．８７ｇ，収率８６％）を得た。
得られた化合物のＴｇは１０７℃であった。
１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３９（ｄ，Ｊ＝７．２Ｈｚ，１Ｈ），７．４６－７．６２（ｍ，１１Ｈ），７．６７－７．７７（ｍ，６Ｈ），７．８３（ｄ，Ｊ＝，８．１Ｈｚ，１Ｈ），７．８７（ｄ，Ｊ＝７．８Ｈｚ，１Ｈ），７．９３（ｄ，Ｊ＝７．５Ｈｚ，１Ｈ），８．０１（ｓ，１Ｈ），８．０５（ｓ，１Ｈ），８．１１（ｓ，１Ｈ），８．２６（ｄ，Ｊ＝８．１Ｈｚ，２Ｈ），８．３３（ｄ，Ｊ＝７．８Ｈｚ，２Ｈ），８．７９－８．８５（ｍ，５Ｈ），９．０９（ｓ，１Ｈ）．
　実施例－８ Under nitrogen stream, 4- (3-bromophenyl) -2- (4-biphenyl) -6-phenylpyridine (3.0 g, 6.49 mmol), 2- [3-{(4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl}]-4,6-diphenyl-1,3,5-triazine (3.00 g, 6.49 mmol), palladium acetate (29.1 mg, 0 .130 mmol) and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (124 mg, 0.260 mmol) were suspended in toluene (50 mL). To this, 4.0 M aqueous sodium hydroxide solution (4.87 mL, 19.5 mmol) was added, and the mixture was stirred at 100 ° C. for 2 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (30 mL) and methanol (60 mL) were added to the obtained concentrated liquid, and the precipitated solid was separated by filtration. The obtained solid was purified by silica gel column chromatography (chloroform / hexane) to obtain the desired 2- {3 ′-[2- (4-biphenyl) -6-phenylpyridin-4-yl] -biphenyl-3. A white solid (yield 3.87 g, yield 86%) of -yl} -4,6-diphenyl-1,3,5-triazine (Compound A-334) was obtained.
The Tg of the obtained compound was 107 ° C.
1 H-NMR (CDCl 3 ) δ (ppm): 7.39 (d, J = 7.2 Hz, 1H), 7.46-7.62 (m, 11H), 7.67-7.77 (m 6H), 7.83 (d, J =, 8.1 Hz, 1H), 7.87 (d, J = 7.8 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 8.01 (s, 1H), 8.05 (s, 1H), 8.11 (s, 1H), 8.26 (d, J = 8.1 Hz, 2H), 8.33 (d, J = 7.8 Hz, 2H), 8.79-8.85 (m, 5H), 9.09 (s, 1H).
Example-8
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000058
　２－（２－ブロモフェニル）－４，６－ジフェニルピリジン　１．００ｇを２－（３－ブロモフェニル）－４－（１－ナフチル）－６－（２－ナフチル）ピリジン　１．２６ｇに変更した以外は実施例－２と同様にして、４，６－ジフェニル－２－｛３’－［４－（１－ナフチル）－６－（２－ナフチル）ピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジン（化合物Ａ－７）の白色固体（収率４７％）を得た。
１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３９－７．５５（ｍ，１２Ｈ），７．６４（ｄｄ，Ｊ＝７．４Ｈｚ，２Ｈ），７．８０（ｄ，Ｊ＝７．３Ｈｚ，２Ｈ），７．８７－７．９６（ｍ，７Ｈ），７．９９（ｓ，１Ｈ），８．２４（ｄ，Ｊ＝８．０Ｈｚ，１Ｈ），８．３７（ｄ，Ｊ＝８．４Ｈｚ，１Ｈ），８．５１（ｓ，１Ｈ），８．６１（ｓ，１Ｈ），８．７１－８．７４（ｍ，５Ｈ），９．０４（ｓ，１Ｈ）．
　合成例－１ 1.00 g of 2- (2-bromophenyl) -4,6-diphenylpyridine was changed to 1.26 g of 2- (3-bromophenyl) -4- (1-naphthyl) -6- (2-naphthyl) pyridine Except as described in Example 2, 4,6-diphenyl-2- {3 ′-[4- (1-naphthyl) -6- (2-naphthyl) pyridin-2-yl] -biphenyl-3- Yle} -1,3,5-triazine (Compound A-7) was obtained as a white solid (yield 47%).
1 H-NMR (CDCl 3 ) δ (ppm): 7.39-7.55 (m, 12H), 7.64 (dd, J = 7.4 Hz, 2H), 7.80 (d, J = 7 .3 Hz, 2H), 7.87-7.96 (m, 7H), 7.99 (s, 1H), 8.24 (d, J = 8.0 Hz, 1H), 8.37 (d, J = 8.4 Hz, 1H), 8.51 (s, 1H), 8.61 (s, 1H), 8.71-8.74 (m, 5H), 9.04 (s, 1H).
Synthesis example-1
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000059
　３－（４，６－ジフェニルピリジン－２－イル）フェニルボロン酸１．００ｇを３－［４－（３－クロロフェニル）－６－フェニルピリジン－２－イル］フェニルボロン酸１．０９ｇに変更した以外は実施例－１と同様にして、４，６－ジフェニル－２－｛３’－［４－（３－クロロフェニル）－６－フェニルピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジンの白色固体（収率７７％）を得た。 1.00 g of 3- (4,6-diphenylpyridin-2-yl) phenylboronic acid was changed to 1.09 g of 3- [4- (3-chlorophenyl) -6-phenylpyridin-2-yl] phenylboronic acid 4,6-diphenyl-2- {3 ′-[4- (3-chlorophenyl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1 in the same manner as in Example-1. , 3,5-triazine was obtained as a white solid (yield 77%).
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３５－７．６６（ｍ，１４Ｈ），７．６９（ｍ，１Ｈ），７．７７（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ），７．８３（ｓ，１Ｈ），７．８７－７．９０（ｍ，２Ｈ），８．１５－８．２０（ｍ，３Ｈ），８．４７（ｓ，１Ｈ），８．７２－８．７６（ｍ，５Ｈ），９．０２（ｓ，１Ｈ）．
　実施例－９ 1 H-NMR (CDCl 3 ) δ (ppm): 7.35-7.66 (m, 14H), 7.69 (m, 1H), 7.77 (d, J = 7.6 Hz, 1H), 7.83 (s, 1H), 7.87-7.90 (m, 2H), 8.15-8.20 (m, 3H), 8.47 (s, 1H), 8.72-8. 76 (m, 5H), 9.02 (s, 1H).
Example-9
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000060
　アルゴン気流下、４，６－ジフェニル－２－｛３’－［４－（３－クロロフェニル）－６－フェニルピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジン（１．００ｇ，１．５４ｍｍｏｌ）、３－ピリジンボロン酸（０．５２ｇ，４．２３ｍｍｏｌ）、酢酸パラジウム（１４．８ｍｇ，０．０６６ｍｍｏｌ）、及び２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル（６１．８ｍｇ，０．１３０ｍｍｏｌ）をテトラヒドロフラン（７０ｍＬ）に懸濁し、７５℃で４８時間撹拌した。室温まで放冷後、反応溶液を減圧濃縮した。得られたスラリーに水（５０ｍＬ）、及びメタノール（１０ｍＬ）を加え、析出した固体を濾別したのち、水（３０ｍＬ）、メタノール（３０ｍＬ）、及びヘキサン（３０ｍＬ）で洗浄した。得られた固体をシリカゲルカラムクロマトグラフィー（クロロホルム）で精製することで、目的の４，６－ジフェニル－２－（３’－｛４－［３－（３－ピリジル）フェニル］－６－フェニルピリジン－２－イル｝－ビフェニル－３－イル）－１，３，５－トリアジン（化合物Ａ－９６）の白色固体（収量０．９０ｇ，収率８４％）を得た。 Under a stream of argon, 4,6-diphenyl-2- {3 ′-[4- (3-chlorophenyl) -6-phenylpyridin-2-yl] -biphenyl-3-yl} -1,3,5-triazine ( 1.00 g, 1.54 mmol), 3-pyridineboronic acid (0.52 g, 4.23 mmol), palladium acetate (14.8 mg, 0.066 mmol), and 2-dicyclohexylphosphino-2 ′, 4 ′, 6 '-Triisopropylbiphenyl (61.8 mg, 0.130 mmol) was suspended in tetrahydrofuran (70 mL) and stirred at 75 ° C. for 48 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Water (50 mL) and methanol (10 mL) were added to the resulting slurry, and the precipitated solid was filtered off and washed with water (30 mL), methanol (30 mL), and hexane (30 mL). The obtained solid was purified by silica gel column chromatography (chloroform) to obtain the desired 4,6-diphenyl-2- (3 ′-{4- [3- (3-pyridyl) phenyl] -6-phenylpyridine. A white solid (yield 0.90 g, yield 84%) of -2-yl} -biphenyl-3-yl) -1,3,5-triazine (Compound A-96) was obtained.
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３３－７．６２（ｍ，１４Ｈ），７．７４（ｔ，Ｊ＝６．２Ｈｚ，２Ｈ），７．８５－７．９２（ｍ，５Ｈ），８．１７（ｄ，Ｊ＝７．７Ｈｚ，３Ｈ），８．４７（ｓ，１Ｈ），８．５６（ｄ，Ｊ＝４．２Ｈｚ，１Ｈ），８．７０（ｄ，Ｊ＝７．５Ｈｚ，５Ｈ），８．８６（ｓ，１Ｈ），９．００（ｓ，１Ｈ）．
実施例－１０ 1 H-NMR (CDCl 3 ) δ (ppm): 7.33-7.62 (m, 14H), 7.74 (t, J = 6.2 Hz, 2H), 7.85-7.92 (m , 5H), 8.17 (d, J = 7.7 Hz, 3H), 8.47 (s, 1H), 8.56 (d, J = 4.2 Hz, 1H), 8.70 (d, J = 7.5 Hz, 5H), 8.86 (s, 1H), 9.00 (s, 1H).
Example-10
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000061
　３－ピリジンボロン酸１．００ｇを４－ピリジンボロン酸１．００ｇに変更した以外は実施例－９と同様にして、４，６－ジフェニル－２－（３’－｛４－［３－（４－ピリジル）フェニル］－６－フェニルピリジン－２－イル｝－ビフェニル－３－イル）－１，３，５－トリアジン（化合物Ａ－９３２）の白色固体（収率２３％）を得た。 4,6-Diphenyl-2- (3 ′-{4- [3- (3) is the same as Example-9 except that 1.00 g of 3-pyridineboronic acid is changed to 1.00 g of 4-pyridineboronic acid. A white solid (yield 23%) of 4-pyridyl) phenyl] -6-phenylpyridin-2-yl} -biphenyl-3-yl) -1,3,5-triazine (Compound A-932) was obtained.
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ（ｐｐｍ）：７．３６－７．５４（ｍ，９Ｈ），７．６２（ｔ，Ｊ＝７．９Ｈｚ，２Ｈ），７．７０（ｔ，Ｊ＝７．５Ｈｚ，１Ｈ），７．７６（ｄ，Ｊ＝７．８Ｈｚ，２Ｈ），７．８５（ｍ，２Ｈ），７．９０－７．９４（ｍ，２Ｈ），７．９９－８．０８（ｍ，３Ｈ），８．１７（ｔ，Ｊ＝８．４Ｈｚ，３Ｈ），８．４４（ｓ，１Ｈ），８．６８－８．７４（ｍ，７Ｈ），８．９９（ｓ，１Ｈ）． 1 H-NMR (CDCl 3 ) δ (ppm): 7.36-7.54 (m, 9H), 7.62 (t, J = 7.9 Hz, 2H), 7.70 (t, J = 7 .5 Hz, 1H), 7.76 (d, J = 7.8 Hz, 2H), 7.85 (m, 2H), 7.90-7.94 (m, 2H), 7.99-8.08 (M, 3H), 8.17 (t, J = 8.4 Hz, 3H), 8.44 (s, 1H), 8.68-8.74 (m, 7H), 8.99 (s, 1H) ).
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000062
　ＷＯ２０１６／００２８６４に記載されている４，６－ジフェニル－２－［４’－（４，６－ジフェニルピリジン－２－イル）－ビフェニル－３－イル］－１，３，５－トリアジン（ＥＴＬ－３、特許文献２の化合物Ａ－７２１）と比較すると、本発明の環状アジン化合物は、高い三重項励起準位を有していることが分かる。 4,6-Diphenyl-2- [4 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl] -1,3,5-triazine (ETL-) described in WO2016 / 002864 3. Compared with compound A-721) of Patent Document 2, it can be seen that the cyclic azine compound of the present invention has a high triplet excited level.
　次に素子評価について記載する。 Next, element evaluation is described.
　素子評価に用いた化合物の構造式及びその略称を以下に示す。 The structural formulas and abbreviations of the compounds used for device evaluation are shown below.
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000063
　素子実施例１
　基板には、２ｍｍ幅の酸化インジウム－スズ（ＩＴＯ）膜（膜厚１１０ｎｍ）がストライプ状にパターンされたＩＴＯ透明電極付きガラス基板を用いた。この基板をイソプロピルアルコールで洗浄した後、オゾン紫外線洗浄にて表面処理を行った。洗浄後の基板に、真空蒸着法で各層の真空蒸着を行い、断面図を図１に示すような発光面積４ｍｍ２有機電界発光素子を作製した。なお、各有機材料は抵抗加熱方式により成膜した。 Element Example 1
As the substrate, a glass substrate with an ITO transparent electrode on which a 2 mm wide indium-tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. The substrate was cleaned with isopropyl alcohol and then surface treated by ozone ultraviolet cleaning. Each layer was vacuum-deposited on the cleaned substrate by a vacuum deposition method, and an organic electroluminescence device having a light-emitting area of 4 mm 2 as shown in FIG. Each organic material was formed by a resistance heating method.
　まず、真空蒸着槽内に前記ガラス基板を導入し、１．０×１０－４Ｐａまで減圧した。 First, the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 × 10 −4 Pa.
　その後、図１の１で示すＩＴＯ透明電極付きガラス基板上に有機化合物層として、正孔注入層２、電荷発生層３、正孔輸送層４、発光層５、電子輸送層６、及び陰極層７を、この順番に積層させながら、いずれも真空蒸着で成膜した。 Thereafter, a hole injection layer 2, a charge generation layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, and a cathode layer are formed as an organic compound layer on the glass substrate with an ITO transparent electrode shown by 1 in FIG. 7 were laminated in this order, and all were formed by vacuum deposition.
　正孔注入層２としては、昇華精製したＨＩＬを０．１５ｎｍ／秒の速度で６５ｎｍ成膜した。 As the hole injection layer 2, 65 nm of HIL purified by sublimation was formed at a rate of 0.15 nm / second.
　電荷発生層３としては、昇華精製したＨＡＴを０．０５ｎｍ／秒の速度で５ｎｍ成膜した。 As the charge generation layer 3, sublimated and purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second.
　正孔輸送層４としては、ＨＴＬを０．１５ｎｍ／秒の速度で１０ｎｍ成膜した。 As the hole transport layer 4, HTL was formed to a thickness of 10 nm at a rate of 0.15 nm / second.
　発光層５としては、ＥＭＬ－１とＥＭＬ－２を９５：５の割合で２５ｎｍ成膜した（成膜速度０．１８ｎｍ／秒）。 As the light-emitting layer 5, EML-1 and EML-2 were deposited to a thickness of 25 nm at a ratio of 95: 5 (deposition rate of 0.18 nm / second).
　電子輸送層６としては、実施例－１で合成した４，６－ジフェニル－２－［３’－（４，６－ジフェニルピリジン－２－イル）－ビフェニル－３－イル］－１，３，５－トリアジン（化合物Ａ－１）及びＬｉｑを５０：５０（重量比）の割合で３０ｎｍ成膜した（成膜速度０．１５ｎｍ／秒）。 As the electron transport layer 6, 4,6-diphenyl-2- [3 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl] -1,3 synthesized in Example-1 was used. A film of 5-triazine (Compound A-1) and Liq was formed at a ratio of 50:50 (weight ratio) to a thickness of 30 nm (deposition rate of 0.15 nm / second).
　最後に、ＩＴＯストライプと直行するようにメタルマスクを配し、陰極層７を成膜した。陰極層７は、銀／マグネシウム（重量比１／１０）と銀を、この順番に、それぞれ８０ｎｍ（成膜速度０．５ｎｍ／秒）と２０ｎｍ（成膜速度０．２ｎｍ／秒）で成膜し、２層構造とした。 Finally, a metal mask was arranged so as to be orthogonal to the ITO stripe, and the cathode layer 7 was formed. The cathode layer 7 is formed of silver / magnesium (weight ratio 1/10) and silver in this order at 80 nm (film formation rate 0.5 nm / second) and 20 nm (film formation rate 0.2 nm / second), respectively. And it was set as the 2 layer structure.
　それぞれの膜厚は、触針式膜厚測定計（ＤＥＫＴＡＫ）で測定した。 Each film thickness was measured with a stylus type film thickness meter (DEKTAK).
　さらに、この素子を酸素及び水分濃度１ｐｐｍ以下の窒素雰囲気グローブボックス内で封止した。封止は、ガラス製の封止キャップと前記成膜基板エポキシ型紫外線硬化樹脂（ナガセケムテックス社製）を用いた。 Furthermore, this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less. For the sealing, a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used.
　上記のようにして作製した有機電界発光素子に直流電流を印加し、ＴＯＰＣＯＮ社製のＬＵＭＩＮＡＮＣＥ　ＭＥＴＥＲ（ＢＭ－９）の輝度計を用いて発光特性を評価した。発光特性として、電流密度１０ｍＡ／ｃｍ２を流した時の電圧（Ｖ）、電流効率（ｃｄ／Ａ）を測定し、連続点灯時の素子寿命（ｈ）を測定した。なお、表２の素子寿命（ｈ）は、作製した素子を初期輝度８００ｃｄ／ｍ２で駆動したときの連続点灯時の輝度減衰時間を測定し、輝度（ｃｄ／ｍ２）が１０％減じるまでに要した時間を測定した。素子寿命は、後述の素子参考例１における素子寿命（ｈ）を基準値（１００）とした相対値で示した。結果を表２に示す。 A direct current was applied to the organic electroluminescent device produced as described above, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON. As light emission characteristics, voltage (V) and current efficiency (cd / A) when a current density of 10 mA / cm 2 was passed were measured, and element lifetime (h) during continuous lighting was measured. Incidentally, Table 2 of element lifetime (h) measures the luminance decay time at the time of continuous lighting when driving was prepared device at an initial luminance 800 cd / m 2, to the luminance (cd / m 2) is reduced by 10% The time required for was measured. The element lifetime was shown as a relative value with the element lifetime (h) in element reference example 1 described later as the reference value (100). The results are shown in Table 2.
　素子実施例２
　素子実施例１において、化合物Ａ－１の代わりに実施例－２で合成した４，６－ジフェニル－２－［２’－（４，６－ジフェニルピリジン－２－イル）－ビフェニル－３－イル］－１，３，５－トリアジン（化合物Ａ－４２１）を用いた以外は、素子実施例１と同じ方法で有機電界発光素子を作製し、評価した。結果を表２に示す。なお、素子寿命については、素子寿命（ｈ）を測定したうえで、素子参考例１の素子寿命を１００とした相対値で表した。 Element Example 2
In Device Example 1, 4,6-diphenyl-2- [2 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example 2 instead of Compound A-1 ] An organic electroluminescence device was prepared and evaluated in the same manner as in Device Example 1 except that 1,3,5-triazine (Compound A-421) was used. The results are shown in Table 2. In addition, about element lifetime, after measuring element lifetime (h), it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
　素子参考例１
　素子実施例１において、化合物Ａ－２の代わりに特開２０１１－０６３５８４に記載されている２－［５－（９－フェナントリル）－４’－（２－ピリミジル）ビフェニル－３－イル］－４，６－ジフェニル－１，３，５－トリアジン（ＥＴＬ－１）を用いた以外は、素子実施例１と同じ方法で有機電界発光素子を作製し、評価した。結果を表２に示した。なお、素子寿命については、素子寿命（ｈ）を測定したうえで、本素子参考例１の素子寿命を基準値（１００）とした。 Element Reference Example 1
In Device Example 1, instead of compound A-2, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP2011-063584A An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that, 6-diphenyl-1,3,5-triazine (ETL-1) was used. The results are shown in Table 2. In addition, about element lifetime, after measuring element lifetime (h), the element lifetime of this element reference example 1 was made into the reference value (100).
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000064
　素子実施例３
　基板には、２ｍｍ幅の酸化インジウム－スズ（ＩＴＯ）膜（膜厚１１０ｎｍ）がストライプ状にパターンされたＩＴＯ透明電極付きガラス基板を用いた。この基板をイソプロピルアルコールで洗浄した後、オゾン紫外線洗浄にて表面処理を行った。洗浄後の基板に、真空蒸着法で各層の真空蒸着を行い、発光面積４ｍｍ２有機電界発光素子を作製した。なお、各有機材料は抵抗加熱方式により成膜した。 Element Example 3
As the substrate, a glass substrate with an ITO transparent electrode on which a 2 mm wide indium-tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. The substrate was cleaned with isopropyl alcohol and then surface treated by ozone ultraviolet cleaning. Each layer was vacuum-deposited on the cleaned substrate by a vacuum evaporation method to produce an organic electroluminescence device having a light emission area of 4 mm 2 . Each organic material was formed by a resistance heating method.
　まず、真空蒸着槽内に前記ガラス基板を導入し、１．０×１０－４Ｐａまで減圧した。 First, the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 × 10 −4 Pa.
　その後、ＩＴＯ透明電極付きガラス基板上に有機化合物層として、正孔注入層、電荷発生層、第一正孔輸送層、第二正孔輸送層、発光層、第一電子輸送層、第二電子輸送層、及び陰極層を、この順番に積層させながら、いずれも真空蒸着で成膜した。 Then, as an organic compound layer on a glass substrate with an ITO transparent electrode, a hole injection layer, a charge generation layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a first electron transport layer, a second electron Both the transport layer and the cathode layer were formed by vacuum deposition while being laminated in this order.
　正孔注入層としては、昇華精製したＨＩＬを０．１５ｎｍ／秒の速度で５５ｎｍ成膜
した。 As the hole injection layer, a sublimated HIL film having a thickness of 55 nm was formed at a rate of 0.15 nm / second.
　電荷発生層としては、昇華精製したＨＡＴを０．０５ｎｍ／秒の速度で５ｎｍ成膜した。 As the charge generation layer, sublimation-purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second.
　第一正孔輸送層としては、ＨＴＬを０．１５ｎｍ／秒の速度で１０ｎｍ成膜した。 As the first hole transport layer, HTL was formed to a thickness of 10 nm at a rate of 0.15 nm / second.
　第二正孔輸送層としては、ＨＴＬ－２を０．１５ｎｍ／秒の速度で１０ｎｍ成膜した。 As the second hole transport layer, HTL-2 was deposited to a thickness of 10 nm at a speed of 0.15 nm / second.
　発光層としては、ＥＭＬ－３とＥＭＬ－４を９５：５の割合で２５ｎｍ成膜した（成膜速度０．１８ｎｍ／秒）。 As the light emitting layer, EML-3 and EML-4 were deposited to a thickness of 25 nm at a ratio of 95: 5 (deposition rate of 0.18 nm / second).
　第一電子輸送層としては、ＥＴＬ－２を０．１５ｎｍ／秒の速度で５ｎｍ成膜した。 As the first electron transport layer, ETL-2 was deposited to a thickness of 5 nm at a rate of 0.15 nm / second.
　第二電子輸送層としては、実施例－３で合成した４，６－ジフェニル－２－｛３’－［４－（４－ジベンゾフリル）－６－フェニルピリジン－２－イル］－ビフェニル－３－イル｝－１，３，５－トリアジン（化合物Ａ－４１）及びＬｉｑを５０：５０（重量比）の割合で２５ｎｍ成膜した（成膜速度０．１５ｎｍ／秒）。 As the second electron transporting layer, 4,6-diphenyl-2- {3 ′-[4- (4-dibenzofuryl) -6-phenylpyridin-2-yl] -biphenyl-3 synthesized in Example-3 was used. -Il} -1,3,5-triazine (compound A-41) and Liq were deposited in a ratio of 50:50 (weight ratio) to a thickness of 25 nm (deposition rate of 0.15 nm / second).
　最後に、ＩＴＯストライプと直行するようにメタルマスクを配し、陰極層　１９を成膜した。 Finally, a metal mask was arranged so as to be orthogonal to the ITO stripe, and a cathode layer 19 was formed.
　陰極層は、銀／マグネシウム（重量比１／１０）と銀を、この順番に、それぞれ８０ｎｍ（成膜速度０．５ｎｍ／秒）と２０ｎｍ（成膜速度０．２ｎｍ／秒）で成膜し、２層構造とした。 The cathode layer was formed by depositing silver / magnesium (weight ratio 1/10) and silver in this order at 80 nm (film formation rate 0.5 nm / second) and 20 nm (film formation rate 0.2 nm / second), respectively. A two-layer structure was adopted.
　それぞれの膜厚は、触針式膜厚測定計（ＤＥＫＴＡＫ）で測定した。 Each film thickness was measured with a stylus type film thickness meter (DEKTAK).
　さらに、この素子を酸素及び水分濃度１ｐｐｍ以下の窒素雰囲気グローブボックス内で封止した。封止は、ガラス製の封止キャップと前記成膜基板エポキシ型紫外線硬化樹脂（ナガセケムテックス社製）を用いた。 Furthermore, this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less. For the sealing, a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used.
　上記のようにして作製した有機電界発光素子に直流電流を印加し、ＴＯＰＣＯＮ社製のＬＵＭＩＮＡＮＣＥ　ＭＥＴＥＲ（ＢＭ－９）の輝度計を用いて発光特性を評価した。発光特性として、電流密度１０ｍＡ／ｃｍ２を流した時の電圧（Ｖ）、電流効率（ｃｄ／Ａ）を測定し、連続点灯時の素子寿命（ｈ）を測定した。なお、表１の素子寿命（ｈ）は、作製した素子を初期輝度１０００ｃｄ／ｍ２で駆動したときの連続点灯時の輝度減衰時間を測定し、輝度（ｃｄ／ｍ２）が１０％減じるまでに要した時間を測定した。電圧、電流効率、及び素子寿命は、後述の素子参考例２における結果を基準値（１００）とした相対値で示した。結果を表３に示す。 A direct current was applied to the organic electroluminescent device produced as described above, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON. As light emission characteristics, voltage (V) and current efficiency (cd / A) when a current density of 10 mA / cm 2 was passed were measured, and element lifetime (h) during continuous lighting was measured. Incidentally, Table 1 of element lifetime (h) measures the luminance decay time at the time of continuous lighting when driving was prepared device at an initial luminance 1000 cd / m 2, to the luminance (cd / m 2) is reduced by 10% The time required for was measured. The voltage, current efficiency, and element lifetime are shown as relative values based on the result in element reference example 2 described later as a reference value (100). The results are shown in Table 3.
　素子実施例４
　素子実施例３において、化合物Ａ－４１の代わりに実施例－２で合成した４，６－ジフェニル－２－［２’－（４，６－ジフェニルピリジン－２－イル）－ビフェニル－３－イル］－１，３，５－トリアジン（化合物Ａ－４２１）を用いた以外は、素子実施例３と同じ方法で有機電界発光素子を作製し、評価した。結果を表３に示す。なお、素子寿命については、素子寿命（ｈ）を測定したうえで、素子参考例２の素子寿命を１００とした相対値で表した。 Element Example 4
In Device Example 3, 4,6-diphenyl-2- [2 ′-(4,6-diphenylpyridin-2-yl) -biphenyl-3-yl synthesized in Example 2 instead of Compound A-41 ] An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 3 except that 1,3,5-triazine (Compound A-421) was used. The results are shown in Table 3. In addition, about element lifetime, after measuring element lifetime (h), it represented by the relative value which set the element lifetime of the element reference example 2 to 100.
　素子参考例２
　素子実施例３において、化合物Ａ－４１の代わりに特開２０１１－０６３５８４に記載されている２－［５－（９－フェナントリル）－４’－（２－ピリミジル）ビフェニル－３－イル］－４，６－ジフェニル－１，３，５－トリアジン（ＥＴＬ－１）を用いた以外は、素子実施例３と同じ方法で有機電界発光素子を作製し、評価した。結果を表３に示した。なお、素子寿命については、素子寿命（ｈ）を測定したうえで、本素子参考例２の素子寿命を基準値（１００）とした。 Element Reference Example 2
In Device Example 3, instead of compound A-41, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP2011-063584A An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 3 except that, 6-diphenyl-1,3,5-triazine (ETL-1) was used. The results are shown in Table 3. In addition, about element lifetime, after measuring element lifetime (h), the element lifetime of this element reference example 2 was made into the reference value (100).
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000065
　本発明を詳細に、また特定の実施態様を参照して説明したが、本発明の本質と範囲を逸脱することなく様々な変更や修正を加えることができることは当業者にとって明らかである。 Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.
　なお、２０１６年６月２４日に出願された日本特許出願２０１６－１２６０４０号の明細書、特許請求の範囲、図面及び要約書の全内容をここに引用し、本発明の明細書の開示として取り入れるものである。 The entire contents of the specification, claims, drawings, and abstract of Japanese Patent Application No. 2016-1226040 filed on June 24, 2016 are incorporated herein as the disclosure of the specification of the present invention. Is.
　本発明のトリアジン化合物（１）は膜質の耐熱性に優れ、当該化合物を用いることによって長寿命性及び発光効率に優れる有機電界発光素子を提供することができる。 The triazine compound (1) of the present invention is excellent in heat resistance of the film quality, and by using the compound, an organic electroluminescent device having excellent long life and luminous efficiency can be provided.
　また、本発明のトリアジン化合物（１）は、低駆動電圧に優れる有機電界発光素子用電子輸送材料として利用される。さらに、本発明によれば、消費電力に優れる有機電界発光素子を提供することができる。 Further, the triazine compound (1) of the present invention is used as an electron transport material for an organic electroluminescence device which is excellent in a low driving voltage. Furthermore, according to the present invention, it is possible to provide an organic electroluminescence device having excellent power consumption.
　また、本発明のトリアジン化合物は、昇華精製時の熱安定性が良いために昇華精製の操作性に優れ、有機電界発光素子の素子劣化の原因となる不純物の少ない材料を提供することができる。また、本発明のトリアジン化合物は蒸着膜の安定性に優れるために長寿命な有機電界発光素子を提供することができる。 In addition, since the triazine compound of the present invention has good thermal stability during sublimation purification, it can provide a material that is excellent in sublimation purification operability and has few impurities causing deterioration of the organic electroluminescence device. Further, since the triazine compound of the present invention is excellent in the stability of the deposited film, it is possible to provide a long-life organic electroluminescence device.
　また、本発明のトリアジン化合物（１）から成る薄膜は、電子輸送能、正孔ブロック能、酸化還元耐性、耐水性、耐酸素性、電子注入特性等に優れるため、有機電界発光素子の材料として有用であり、電子輸送材、正孔ブロック材、発光ホスト材等として有用である。とりわけ電子輸送材と用いた際に有用である。また本発明のトリアジン化合物（１）はワイドバンドギャップ化合物なため、従来の蛍光素子用途のみならず、燐光素子へ好適に用いることができる。 In addition, the thin film comprising the triazine compound (1) of the present invention is useful as a material for an organic electroluminescence device because it has excellent electron transport ability, hole blocking ability, oxidation-reduction resistance, water resistance, oxygen resistance, electron injection characteristics, and the like. It is useful as an electron transport material, a hole blocking material, a light emitting host material, and the like. It is particularly useful when used as an electron transport material. Further, since the triazine compound (1) of the present invention is a wide band gap compound, it can be suitably used not only for conventional fluorescent device applications but also for phosphorescent devices.

Claims (13)

  1. 一般式（１）で示されるトリアジン化合物。
    Figure JPOXMLDOC01-appb-C000001
     （一般式（１）中、
    Ａｒ１は、フェニル基、又はナフチル基（これらの基は、フッ素原子、メチル基、又はフェニル基で置換されていてもよい）を表し、二つのＡｒ１は同一である。
    Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表す。
    Ａｒ４、及びＡｒ７は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）を表す。
    Ａｒ２、Ａｒ３、及びＡｒ４の環構成炭素原子の総数、及びＡｒ５、Ａｒ６、及びＡｒ７の環構成炭素原子の総数は、いずれも５～２５である。
    Ａは、単結合を表す。
    Ｂ１及びＢ２は、単結合又は水素原子を表す。但し、Ｂ１又はＢ２の何れか一方が単結合を表してＡと単結合を形成し、もう一方は水素原子を表す。
    Ｚ１及びＺ２は各々独立に、窒素原子又はＣ－Ｈを表す。但し、Ｚ１又はＺ２の何れか一方が窒素原子を表し、もう一方はＣ－Ｈを表す。）     A triazine compound represented by the general formula (1).
    Figure JPOXMLDOC01-appb-C000001
     (In general formula (1),
    Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same.
    Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring. 1 to 25 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
    Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
    The total number of ring carbon atoms of Ar 2 , Ar 3 , and Ar 4 and the total number of ring carbon atoms of Ar 5 , Ar 6 , and Ar 7 are all 5 to 25.
    A represents a single bond.
    B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
    Z 1 and Z 2 each independently represents a nitrogen atom or C—H. However, either Z 1 or Z 2 represents a nitrogen atom, and the other represents C—H. )
  2. Ａｒ１が、フェニル基、トリル基、ナフチル基、又はビフェニル基を表し、二つのＡｒ１は同一である請求項１に記載のトリアジン化合物。 Ar 1 is a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group, a triazine compound according to claim 1 Two Ar 1 are identical.
  3. Ａｒ１が、いずれも、フェニル基である請求項１、又は２に記載のトリアジン化合物。 The triazine compound according to claim 1, wherein each Ar 1 is a phenyl group.
  4. Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６が、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ’）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合であり、尚且つＡｒ４、及びＡｒ７が、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ’）６員環のみからなる炭素数３～１１の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ’）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることを特徴とする請求項１、２、又は３に記載のトリアジン化合物。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b ′) a carbon number consisting of only a 6-membered ring. 3 to 11 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed ring having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S Heteroaromatic groups (the groups represented by (a), (b ′) and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, and an alkyl group having 1 to 4 carbon atoms) Or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 are each independently (a) a monocyclic ring having 6 to 24 carbon atoms. Or a condensed ring aromatic hydrocarbon group, (b ′) a monocyclic or condensed ring containing 3 to 11 carbon atoms consisting of only a 6-membered ring An aromatic heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (the (a) , (B ′) and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). The triazine compound according to claim 1, 2, or 3.
  5. Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６が、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、ジベンゾチエニル基（これらの基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表し、尚且つＡｒ４、及びＡｒ７は、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることを特徴とする請求項１、２、３、又は４に記載のトリアジン化合物。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, Triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (these groups are phenyl group, tolyl group, pyridyl group) , A methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 are Each independently phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, benzo Fluorenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, triazyl, pyrimidyl, piperazyl, pyridyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, dibenzofuranyl, or dibenzothienyl A group (these groups may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), Or the triazine compound according to 4.
  6. Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６が、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、ジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表し、尚且つＡｒ４、及びＡｒ７は、各々独立に、フェニル基、ナフチル基、フルオレニル基、アントリル基、フェナントリル基、ベンゾフルオレニル基、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、トリアジル基、ピリミジル基、ピペラジル基、ピリジル基、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、ジベンゾフラニル基、又はジベンゾチエニル基（これらの基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）であることを特徴とする請求項１、２、３、４、又は５に記載のトリアジン化合物。 Ar 2 , Ar 3 , Ar 5 , and Ar 6 are each independently a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, Triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group (these groups are fluorine atom, carbon number 1 to 4 Or an alkoxy group having 1 to 4 carbon atoms), or a single bond, and Ar 4 and Ar 7 are each independently a phenyl group, a naphthyl group, or a fluorenyl group. , Anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluorane Tenenyl group, triphenylenyl group, triazyl group, pyrimidyl group, piperazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are fluorine atom, carbon 6. The triazine compound according to claim 1, 2, 3, 4, or 5, which may have an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
  7. －Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基が、各々独立に、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、フルオランテニルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、キノリルフェニル基、チエニルフェニル基、フリルフェニル基、ベンゾチエニルフェニル基、ベンゾフリルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、ベンゾチエニル基、ベンゾフリル基、フェナントリル基、アントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、フッ素原子、又はメチル基で置換されていてもよい）であることを特徴とする請求項１、２、３、４、５、又は６に記載のトリアジン化合物。 The group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group; Group, fluoranthenylphenyl group, pyridylphenyl group, pyrimidylphenyl group, quinolylphenyl group, thienylphenyl group, furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group , Pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, bipyridyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl Group or di The triazine compound according to claim 1, 2, 3, 4, 5, or 6, which is a benzofuryl group (these groups may be substituted with a fluorine atom or a methyl group).
  8. －Ａｒ２－Ａｒ３－Ａｒ４で表される基、及び－Ａｒ５－Ａｒ６－Ａｒ７で表される基が、各々独立に、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、メチル基で置換されていてもよい）である請求項１、２、３、４、５、６、又は７に記載のトリアジン化合物。 The group represented by —Ar 2 —Ar 3 —Ar 4 and the group represented by —Ar 5 —Ar 6 —Ar 7 are each independently a phenyl group, a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group; Group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, A bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a methyl group), 1, 2, 3, 4, 5, 6, or The triazine compound according to 7.
  9. －Ａｒ２－Ａｒ３－Ａｒ４で表される基、又は－Ａｒ５－Ａｒ６－Ａｒ７で表される基の何れか一方が、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、フッ素原子、又はメチル基で置換されていてもよい）であり、もう一方が、フェニル基、ビフェニル基、ピリジル基、又はナフチル基（これらの基は、メチル基で置換されていてもよい）である請求項１、２、３、４、５、６、７、又は８に記載のトリアジン化合物。 Either the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl. Group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, A bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a fluorine atom or a methyl group), and the other is a phenyl group, a biphenyl group, Pyridyl group or naphthyl group (these groups are substituted with methyl group) The triazine compound according to claim 1, 2, 3, 4, 5, 6, 7, or 8.
  10. －Ａｒ２－Ａｒ３－Ａｒ４で表される基、又は－Ａｒ５－Ａｒ６－Ａｒ７で表される基の何れか一方が、フェニル基、ビフェニル基、ナフチルフェニル基、フェナントリルフェニル基、ピリジルフェニル基、ピリミジルフェニル基、ジベンゾチエニルフェニル基、ジベンゾフリルフェニル基、ピリジルジベンゾチエニルフェニル基、ピリジルジベンゾフリルフェニル基、ピリミジルジベンゾチエニルフェニル基、ピリミジルジベンゾフリルフェニル基、ビピリジル基、ナフチル基、フェナントリル基、ジベンゾチエニル基、又はジベンゾフリル基（これらの基は、メチル基で置換されていてもよい）であり、もう一方がフェニル基、又はナフチル基である請求項１、２、３、４、５、６、７、８、又は９に記載のトリアジン化合物。 Either the group represented by —Ar 2 —Ar 3 —Ar 4 or the group represented by —Ar 5 —Ar 6 —Ar 7 is phenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl. Group, pyridylphenyl group, pyrimidylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, pyridyldibenzothienylphenyl group, pyridyldibenzofurylphenyl group, pyrimidyldibenzothienylphenyl group, pyrimidyldibenzofurylphenyl group, 2. A bipyridyl group, a naphthyl group, a phenanthryl group, a dibenzothienyl group, or a dibenzofuryl group (these groups may be substituted with a methyl group), and the other is a phenyl group or a naphthyl group. The triazine compound according to 2, 3, 4, 5, 6, 7, 8, or 9.
  11. カップリング反応を利用することを特徴とする請求項１に記載の一般式（１）で示されるトリアジン化合物の製造方法。
    Figure JPOXMLDOC01-appb-C000002
     （一般式（１）中、
    Ａｒ１は、フェニル基、又はナフチル基（これらの基は、フッ素原子、メチル基、又はフェニル基で置換されていてもよい）を表し、二つのＡｒ１は同一である。
    Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表す。
    Ａｒ４、及びＡｒ７は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）を表す。
    Ａｒ２、Ａｒ３、及びＡｒ４の環構成炭素原子の総数、及びＡｒ５、Ａｒ６、及びＡｒ７の環構成炭素原子の総数は、いずれも５～２５である。
    Ａは、単結合を表す。
    Ｂ１及びＢ２は、単結合又は水素原子を表す。但し、Ｂ１又はＢ２の何れか一方が単結合を表してＡと単結合を形成し、もう一方は水素原子を表す。
    Ｚ１及びＺ２は各々独立に、窒素原子又はＣ－Ｈを表す。但し、Ｚ１又はＺ２の何れか一方が窒素原子を表し、もう一方はＣ－Ｈを表す。）     The method for producing a triazine compound represented by the general formula (1) according to claim 1, wherein a coupling reaction is used.
    Figure JPOXMLDOC01-appb-C000002
     (In general formula (1),
    Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same.
    Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring. 1 to 25 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
    Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
    The total number of ring carbon atoms of Ar 2 , Ar 3 , and Ar 4 and the total number of ring carbon atoms of Ar 5 , Ar 6 , and Ar 7 are all 5 to 25.
    A represents a single bond.
    B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
    Z 1 and Z 2 each independently represents a nitrogen atom or C—H. However, either Z 1 or Z 2 represents a nitrogen atom, and the other represents C—H. )
  12. 請求項１に記載の一般式（１）で示されるトリアジン化合物を含む有機電界発光素子用材料。
    Figure JPOXMLDOC01-appb-C000003
     （一般式（１）中、
    Ａｒ１は、フェニル基、又はナフチル基（これらの基は、フッ素原子、メチル基、又はフェニル基で置換されていてもよい）を表し、二つのＡｒ１は同一である。
    Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表す。
    Ａｒ４、及びＡｒ７は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）を表す。
    Ａｒ２、Ａｒ３、及びＡｒ４の環構成炭素原子の総数、及びＡｒ５、Ａｒ６、及びＡｒ７の環構成炭素原子の総数は、いずれも５～２５である。
    Ａは、単結合を表す。
    Ｂ１及びＢ２は、単結合又は水素原子を表す。但し、Ｂ１又はＢ２の何れか一方が単結合を表してＡと単結合を形成し、もう一方は水素原子を表す。
    Ｚ１及びＺ２は各々独立に、窒素原子又はＣ－Ｈを表す。但し、Ｚ１又はＺ２の何れか一方が窒素原子を表し、もう一方はＣ－Ｈを表す。）     The material for organic electroluminescent elements containing the triazine compound shown by General formula (1) of Claim 1.
    Figure JPOXMLDOC01-appb-C000003
     (In general formula (1),
    Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same.
    Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring. 1 to 25 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
    Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
    The total number of ring carbon atoms of Ar 2 , Ar 3 , and Ar 4 and the total number of ring carbon atoms of Ar 5 , Ar 6 , and Ar 7 are all 5 to 25.
    A represents a single bond.
    B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
    Z 1 and Z 2 each independently represents a nitrogen atom or C—H. However, either Z 1 or Z 2 represents a nitrogen atom, and the other represents C—H. )
  13. 請求項１に記載の一般式（１）で示されるトリアジン化合物を含む有機電界発光素子用電子輸送材料。
    Figure JPOXMLDOC01-appb-C000004
     （一般式（１）中、
    Ａｒ１は、フェニル基、又はナフチル基（これらの基は、フッ素原子、メチル基、又はフェニル基で置換されていてもよい）を表し、二つのＡｒ１は同一である。
    Ａｒ２、Ａｒ３、Ａｒ５、及びＡｒ６は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フェニル基、トリル基、ピリジル基、メチルピリジル基、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）、又は単結合を表す。
    Ａｒ４、及びＡｒ７は、各々独立に、（ａ）炭素数６～２４の単環若しくは縮環芳香族炭化水素基、（ｂ）６員環のみからなる炭素数３～２５の単環若しくは縮環含窒素ヘテロ芳香族基、又は（ｃ）Ｈ、Ｃ、Ｏ、及びＳからなる原子群から選ばれる原子で構成される炭素数３～２５の単環若しくは縮環ヘテロ芳香族基（該（ａ）、（ｂ）、及び（ｃ）で表される基は、フッ素原子、炭素数１～４のアルキル基、又は炭素数１～４のアルコキシ基を有していてもよい）を表す。
    Ａｒ２、Ａｒ３、及びＡｒ４の環構成炭素原子の総数、及びＡｒ５、Ａｒ６、及びＡｒ７の環構成炭素原子の総数は、いずれも５～２５である。
    Ａは、単結合を表す。
    Ｂ１及びＢ２は、単結合又は水素原子を表す。但し、Ｂ１又はＢ２の何れか一方が単結合を表してＡと単結合を形成し、もう一方は水素原子を表す。
    Ｚ１及びＺ２は各々独立に、窒素原子又はＣ－Ｈを表す。但し、Ｚ１又はＺ２の何れか一方が窒素原子を表し、もう一方はＣ－Ｈを表す。）     The electron transport material for organic electroluminescent elements containing the triazine compound shown by General formula (1) of Claim 1.
    Figure JPOXMLDOC01-appb-C000004
     (In general formula (1),
    Ar 1 represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), and the two Ar 1 are the same.
    Ar 2 , Ar 3 , Ar 5 , and Ar 6 each independently represent (a) a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or (b) a carbon number of 3 consisting of only a 6-membered ring. 1 to 25 monocyclic or condensed nitrogen-containing heteroaromatic group, (c) a monocyclic or condensed heterocycle having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S An aromatic group (the groups represented by (a), (b), and (c) are a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or Or an alkoxy group having 1 to 4 carbon atoms), or a single bond.
    Ar 4 and Ar 7 are each independently (a) a monocyclic or condensed ring aromatic hydrocarbon group having 6 to 24 carbon atoms, (b) a monocyclic group having 3 to 25 carbon atoms consisting of only a 6-membered ring, or A condensed nitrogen-containing heteroaromatic group, or (c) a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O, and S (The groups represented by (a), (b), and (c) may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms). .
    The total number of ring carbon atoms of Ar 2 , Ar 3 , and Ar 4 and the total number of ring carbon atoms of Ar 5 , Ar 6 , and Ar 7 are all 5 to 25.
    A represents a single bond.
    B 1 and B 2 represent a single bond or a hydrogen atom. However, either B 1 or B 2 represents a single bond to form a single bond with A, and the other represents a hydrogen atom.
    Z 1 and Z 2 each independently represents a nitrogen atom or C—H. However, either Z 1 or Z 2 represents a nitrogen atom, and the other represents C—H. )
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