WO2017221974A1 - 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 - Google Patents

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 Download PDF

Info

Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
group
pyridyl
phenyl
carbon atoms
phenyl group
Prior art date
Application number
PCT/JP2017/022826
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
服部一希
新井信道
田中剛
野村桂甫
Original Assignee
東ソー株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 東ソー株式会社 filed Critical 東ソー株式会社
Priority to KR1020187037357A priority Critical patent/KR102424486B1/ko
Priority to CN201780039272.4A priority patent/CN109311844B/zh
Publication of WO2017221974A1 publication Critical patent/WO2017221974A1/ja

Links

Images

Classifications

    • 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/JP2017/022826 2016-06-24 2017-06-21 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 WO2017221974A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020187037357A KR102424486B1 (ko) 2016-06-24 2017-06-21 트라이아진 화합물, 이의 제조 방법, 및 이것을 구성 성분으로 하는 유기 전계발광소자
CN201780039272.4A CN109311844B (zh) 2016-06-24 2017-06-21 三嗪化合物、其制造方法、和将其作为构成成分的有机电致发光元件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016126040 2016-06-24
JP2016-126040 2016-06-24

Publications (1)

Publication Number Publication Date
WO2017221974A1 true WO2017221974A1 (ja) 2017-12-28

Family

ID=60784653

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/022826 WO2017221974A1 (ja) 2016-06-24 2017-06-21 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

Country Status (4)

Country Link
JP (1) JP6977325B2 (zh)
KR (1) KR102424486B1 (zh)
CN (1) CN109311844B (zh)
WO (1) WO2017221974A1 (zh)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128416A (zh) * 2018-02-02 2019-08-16 北京鼎材科技有限公司 一种通式化合物及其应用
WO2020050372A1 (ja) * 2018-09-07 2020-03-12 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
JP2020070262A (ja) * 2018-11-01 2020-05-07 東ソー株式会社 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
JP2020117472A (ja) * 2019-01-25 2020-08-06 東ソー株式会社 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
KR20210080383A (ko) 2018-10-22 2021-06-30 토소가부시키가이샤 환상 아진 화합물, 유기 전계발광소자용 재료, 유기 전계발광소자용 전자수송 재료 및 유기 전계발광소자
TWI754906B (zh) * 2019-03-29 2022-02-11 大陸商吉林省元合電子材料有限公司 取代的1,3,5-三嗪化合物、組合物及其應用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111808082B (zh) * 2019-04-11 2023-10-17 北京鼎材科技有限公司 一种发光材料及其应用
EP4006023A4 (en) * 2019-07-30 2023-10-11 Tosoh Corporation CYCLIC AZINE COMPOUND, ORGANIC ELECTROLUMINescent ELEMENT MATERIAL, ELECTRON TRANSPORT MATERIAL FOR ORGANIC ELECTROLUMINescent ELEMENT, AND ORGANIC ELECTROLUMINescent ELEMENT
WO2022177374A1 (ko) * 2021-02-18 2022-08-25 주식회사 엘지화학 유기 발광 소자

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015125814A1 (ja) * 2014-02-21 2015-08-27 東ソー株式会社 トリアジン化合物及びその製造方法
WO2015156449A1 (ko) * 2014-04-09 2015-10-15 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
WO2016002864A1 (ja) * 2014-07-01 2016-01-07 東ソー株式会社 トリアジン化合物、その製造方法、及びその用途
WO2016204375A1 (ko) * 2015-06-17 2016-12-22 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5812583B2 (ja) 2009-08-21 2015-11-17 東ソー株式会社 トリアジン誘導体、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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015125814A1 (ja) * 2014-02-21 2015-08-27 東ソー株式会社 トリアジン化合物及びその製造方法
WO2015156449A1 (ko) * 2014-04-09 2015-10-15 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
WO2016002864A1 (ja) * 2014-07-01 2016-01-07 東ソー株式会社 トリアジン化合物、その製造方法、及びその用途
WO2016204375A1 (ko) * 2015-06-17 2016-12-22 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128416A (zh) * 2018-02-02 2019-08-16 北京鼎材科技有限公司 一种通式化合物及其应用
CN110128416B (zh) * 2018-02-02 2023-08-15 北京鼎材科技有限公司 一种通式化合物及其应用
WO2020050372A1 (ja) * 2018-09-07 2020-03-12 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
KR20210080383A (ko) 2018-10-22 2021-06-30 토소가부시키가이샤 환상 아진 화합물, 유기 전계발광소자용 재료, 유기 전계발광소자용 전자수송 재료 및 유기 전계발광소자
JP2020070262A (ja) * 2018-11-01 2020-05-07 東ソー株式会社 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
JP7206816B2 (ja) 2018-11-01 2023-01-18 東ソー株式会社 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
JP2020117472A (ja) * 2019-01-25 2020-08-06 東ソー株式会社 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
JP7215192B2 (ja) 2019-01-25 2023-01-31 東ソー株式会社 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
TWI754906B (zh) * 2019-03-29 2022-02-11 大陸商吉林省元合電子材料有限公司 取代的1,3,5-三嗪化合物、組合物及其應用

Also Published As

Publication number Publication date
KR102424486B1 (ko) 2022-07-22
JP6977325B2 (ja) 2021-12-08
CN109311844B (zh) 2021-07-20
KR20190019089A (ko) 2019-02-26
CN109311844A (zh) 2019-02-05
JP2018002711A (ja) 2018-01-11

Similar Documents

Publication Publication Date Title
JP6421474B2 (ja) 環状アジン化合物、その製造方法、及びそれを用いた有機電界発光素子
KR102424486B1 (ko) 트라이아진 화합물, 이의 제조 방법, 및 이것을 구성 성분으로 하는 유기 전계발광소자
WO2016002864A1 (ja) トリアジン化合物、その製造方法、及びその用途
JP2017141216A (ja) 環状アジン化合物、及びその用途
JP2021070682A (ja) ピリジル基を有するトリアジン化合物
JP2020164503A (ja) オルト構造を有するトリアジン化合物
JP7469753B2 (ja) トリアジン化合物、有機電界発光素子用材料、及び有機電界発光素子
WO2018173882A1 (ja) 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料
JP6500644B2 (ja) トリアジン化合物、その製造方法、及びその用途
JP7159550B2 (ja) 環状アジン化合物、有機電界発光素子用材料および有機電界発光素子用電子輸送材料
WO2019163959A1 (ja) 環状アジン化合物、有機電界発光素子用材料および有機電界発光素子用電子輸送材料
JP6421502B2 (ja) 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
JP7285663B2 (ja) ２’－アリールビフェニリル基を有するトリアジン化合物
WO2020085319A1 (ja) 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
JP2022132782A (ja) 新規なアダマンタン化合物およびその化合物を含む有機電界発光素子
WO2020111225A1 (ja) トリアジン化合物、有機電界発光素子用材料、及び有機電界発光素子
JP7318178B2 (ja) 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料
CN112912372A (zh) 环状吖嗪化合物、有机电致发光元件用材料、有机电致发光元件用电子输送材料、以及有机电致发光元件
JP7379830B2 (ja) 環状アジン化合物、有機電界発光素子用材料および有機電界発光素子用電子輸送材料
JP7215192B2 (ja) 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
JP7206816B2 (ja) 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、及び有機電界発光素子
WO2022211123A1 (ja) 横電流抑制材料、カルバゾール化合物、正孔注入層、および有機エレクトロルミネッセンス素子
JP2021161116A (ja) 環状アジン化合物、その製造法、およびその用途
JP2021109853A (ja) トリアジン化合物、及び有機電界発光素子用材料
JP2023057461A (ja) ジピリジルフェニル基を有するトリアジン化合物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17815442

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20187037357

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 17815442

Country of ref document: EP

Kind code of ref document: A1