WO2019111844A1 - Arylamine compound and organic electroluminescence device - Google Patents

Arylamine compound and organic electroluminescence device Download PDF

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WO2019111844A1
WO2019111844A1 PCT/JP2018/044353 JP2018044353W WO2019111844A1 WO 2019111844 A1 WO2019111844 A1 WO 2019111844A1 JP 2018044353 W JP2018044353 W JP 2018044353W WO 2019111844 A1 WO2019111844 A1 WO 2019111844A1
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substituted
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substituent
carbon atoms
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望月　俊二
剛史 山本
幸喜 加瀬
駿河　和行
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保土谷化学工業株式会社
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Priority to JP2019558196A priority Critical patent/JP7163311B2/en
Priority to KR1020207014080A priority patent/KR20200096506A/en
Priority to CN201880078675.4A priority patent/CN111433930B/en
Publication of WO2019111844A1 publication Critical patent/WO2019111844A1/en

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Definitions

  • the present invention relates to a compound suitable for an organic electroluminescent device (hereinafter referred to as an organic EL device), which is a self-luminous device suitable for various display devices, and to the device, specifically an arylamine compound, The present invention relates to an organic EL device using the compound.
  • an organic EL device an organic electroluminescent device
  • the present invention relates to an organic EL device using the compound.
  • the organic EL element is a self-light emitting element, it is brighter than the liquid crystal element and has excellent visibility and clear display, so active research has been conducted.
  • Eastman Kodak Company C.I. W. Tang et al. Made the organic EL device using the organic material practical by developing a laminated structure device in which various functions are shared by the respective materials. They stack a phosphor capable of transporting electrons, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ) and an aromatic amine compound capable of transporting holes, and both charge Were injected into the phosphor layer to cause light emission, and a high luminance of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
  • Non-Patent Document 2 In addition, utilization of triplet excitons has been attempted for the purpose of further improvement of luminous efficiency, and utilization of phosphorescent emitters has been studied (see, for example, Non-Patent Document 2).
  • the light emitting layer can also be manufactured by doping a phosphor or a phosphorescence emitting material to a charge transporting compound generally called a host material.
  • a highly efficient organic EL device has been proposed which uses an iridium complex as a phosphorescent material and a compound having a carbazole structure as a host material (for example, Patent Document 3).
  • carbazole derivatives for example, HTM-1 described below
  • T1 triplet energy levels
  • Patent Document 7 proposes a monoamine compound (for example, HTM-2 below) represented by the following formula having excellent electric durability and high hole transportability. It is done.
  • Japanese Patent Application Laid-Open No. 8-048656 Japanese Patent Application Laid-Open No. 7-126615 Japanese Patent Application Laid-Open No. 2006-151979 International Publication No. 2015/034125 International Publication No. 2016/013732 Japanese Patent Application Laid-Open No. 8-003547 Japanese Patent Application Laid-Open No. 2006-352088 International Publication No. 2017/099155 Japanese Patent Application Laid-Open No. 2002-105055 International Publication No. 2014/007565 International Publication No. 2014/188947 International Publication No. 2015/190400 Japan JP 2010-83862 International Publication No. 2015/038503 Japanese Patent Application Laid-Open No. 2005-108804 International Publication No. 2008/62636 International Publication No. 2014/009310
  • the object of the present invention is as a material for organic EL devices having high efficiency and high durability, excellent in hole injection / transport performance, electron blocking ability, high stability in thin film state, luminous efficiency
  • An object of the present invention is to provide an organic compound having high excellent properties, and further to provide a highly efficient and highly durable organic EL device using this compound.
  • Physical properties to be provided by the organic compound to be provided by the present invention include (1) good hole injection characteristics, (2) high hole mobility, and (3) electron blocking ability. (4) stability of the thin film state, and (5) excellent durability to electrons. Further, as physical properties to be provided by the organic EL element to be provided by the present invention, (1) high luminous efficiency and (2) long element life can be mentioned.
  • the present inventors are expecting that the aromatic tertiary amine structure has high hole injecting / transporting ability, and the effect on the electric durability and the thin film stability. And design and chemically synthesize monoamine compounds having a novel triarylamine structure, and trial manufacture of various organic EL devices using the compounds to complete the present invention as a result of intensive characterization of the devices. It came to
  • the organic EL device of the present invention which can solve the above problems, 1) Between the anode and the cathode, at least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above At least one of the layers disposed between the electron transporting layer and the electron transporting layer contains an arylamine compound represented by the following general formula (1).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group
  • R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent
  • Another organic EL device of the present invention which can solve the above problems, is 2) Between the anode and the cathode, at least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above At least one of the layers disposed between the electron transporting layer and the electron transporting layer contains an arylamine compound represented by the following general formula (2).
  • Ar 1 and Ar 2 may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted fused polycyclic aromatic compounds
  • Ar 5 and Ar 6 may be identical to or different from each other, and may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group
  • R 4 is a hydrogen atom, a deuterium atom or a fluorine atom
  • arylamine compound of this invention which can solve the said subject is represented by following General formula (1).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group
  • R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent
  • the arylamine compound of the present invention is useful as a light emitting layer of the organic EL device or as a second hole transporting layer adjacent to the light emitting layer, has excellent electron blocking ability, has excellent electron durability, and is amorphous. Is excellent, the thin film state is stable, and the heat resistance is excellent.
  • the organic EL device of the present invention is high in luminous efficiency and power efficiency, and can extend the life of the device due to excellent electron durability.
  • FIG. 6 is a view showing EL element configurations of Examples 10 to 21 and Comparative Examples 1 to 6.
  • the term "to” is a term representing a range.
  • the description “5 to 10” means “5 or more and 10 or less”, and indicates a range including the numerical values themselves described before and after “to”.
  • At least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above An organic EL device, wherein at least one of the layers disposed between the electron transport layer and the layer contains an arylamine compound represented by the following general formula (1).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group
  • R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent
  • At least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above
  • An organic EL device comprising an arylamine compound represented by the following general formula (2), at least one of the layers disposed between the electron transport layer and the electron transport layer.
  • Ar 1 and Ar 2 may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted fused polycyclic aromatic compounds
  • Ar 5 and Ar 6 may be identical to or different from each other, and may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group
  • R 4 is a hydrogen atom, a deuterium atom or a fluorine atom
  • the green light emitting layer includes a host and a phosphorescent dopant, and the host is a table represented by the following chemical formula Host-B with at least one first host compound represented by the following chemical formula Host-A.
  • Z is each independently N or CRa, at least one of Z is N, and R 5 to R 14 and Ra are each independently a hydrogen atom Deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,
  • the total number of 6-membered rings substituted with a triphenylene group in Host-A is 6 or less
  • L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted ter
  • n1 to n3 each independently represent 0 or 1, and n1 + n2 + n3 ⁇ 1).
  • Y is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms
  • Ar 7 Is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms
  • R 15 to R 18 each independently represent hydrogen Atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring forming C 4 -C to a heteroaryl group 50, at least one of R 15 ⁇ R 18 and Ar 7 represents a substituted or unsubstituted trip
  • the organic EL device according to any one of 1) to 3), wherein the green light emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex containing iridium.
  • the green light emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is any of the metal complexes represented by the following general formula (3): Organic EL element as described.
  • R 19 to R 34 may be the same as or different from each other, and are each independently a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, or a C1-C6 linear group optionally having substituents) Or a branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched chain having 2 to 6 carbon atoms
  • An alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent Trimethylsilyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted fused polycyclic aromatic group, substituted or unsubstituted aryloxy group, or .n representing the family
  • Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted fused polycyclic aromatic group
  • Ar 9 and Ar 10 may be the same as or different from each other
  • B represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted fused polycyclic aromatic group
  • B represents a monovalent group represented by the following structural formula (5):
  • Ar 9 and Ar 10 can not simultaneously be hydrogen atoms.
  • Ar 11 represents a substituted or unsubstituted aromatic heterocyclic group
  • R 35 to R 38 may be the same or different and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, A cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group; Represents an unsubstituted fused polycyclic aromatic group).
  • Ar 12 and Ar 13 may be the same as or different from each other, and are a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, Or a substituted or unsubstituted aromatic heterocyclic group, wherein V 1 is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aromatic heterocyclic group A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent And X 2 represents a linear or branched alkenyl group having 2 to 6 carbon atoms which may have X, an oxygen atom or a sulfur atom, and W 1 and W 2 may be the same or different
  • R 39 to R 44 each independently represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear C 1-6 linear chain that may have a substituent
  • R 1 represents a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.
  • r 1 ⁇ r 4 represents an integer of 0 to 5
  • r 5 is .
  • r 1 ⁇ r 6 represents an integer of 0 to 4 represent an integer of 2 or more
  • the same benzene ring Each of R 39 to R 44 bonded to plural groups may be the same or different from each other, and the benzene ring and the substituent substituted to the benzene ring may be substituted each other by plural substituents on the same benzene ring.
  • HTM-A HTM-A
  • HTM-F HTM-F
  • R 45 to R 56 each independently represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear chain having 1 to 6 carbon atoms which may have a substituent
  • R 7 represents a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.
  • each ⁇ r 18 the same May have, if r 7 ⁇ r 12 represents an integer of 0 ⁇ 5, r 13 ⁇ r 18 is .r 7 ⁇ r 18 represents an integer of 0 to 4 represent an integer of 2 or more, the same benzene ring And R 45 to R 56 bonded to each other may be the same as or different from each other, and the benzene ring and the substituents substituted on the benzene ring may be substituents each substituted on the same benzene ring, and via the nitrogen atom is a benzene ring which are adjacent to each other, each a single bond, a substituted or unsubstituted methylene group, an oxygen atom or .K 2 ⁇ K 4 be bonded to the sulfur atom to form a ring respectively It may be the same or different, and represents a divalent group represented by (HTM-A) to (HTM-F) described in General Formula (7), or a single bond.)
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group
  • R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent
  • aromatic hydrocarbon group “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the ring aromatic group
  • phenanthrenyl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl
  • the “substituent” in the “substituted aromatic hydrocarbon group”, the “substituted aromatic heterocyclic group” or the “substituted fused polycyclic aromatic group” represented by Ar 1 to Ar 4 in the general formula (1) Specifically, deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom, etc .; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl Linear or branched alkyloxy group having 1 to 6 carbon atoms such
  • C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted represented by R 1 to R 3 in the general formula (1), “having a substituent” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)”
  • the linear or branched alkyl group of 6 are specifically mentioned , Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cycl
  • C1-C6 linear or branched alkyl group having a substituent which is represented by R 1 to R 3 in the general formula (1),“ c-5 having a substituent ”
  • Specific examples of the "substituent" in the cycloalkyl group of "" or “C2-C6 linear or branched alkenyl group having a substituent” include deuterium atom, cyano group, nitro group; A halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group An alkenyl group such as a phenyl group, an aryloxy group such as a tolyloxy group, an arylalkyloxy group such as a benzyloxy group or a phenethyloxy group; Aromatic hydrocarbon
  • methyloxy group, ethyloxy group, n-propyloxy group isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group , Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Etc.
  • these groups to each other is a single bond, a substitute
  • C1-C6 linear or branched alkyloxy group having a substituent which is represented by R 1 to R 3 in the general formula (1), or“ c5-C having a substituent ”
  • R 1 to R 3 the “substituent” in the cycloalkyloxy group of 10
  • R 1 to R 3 the “substituent” in the cycloalkyloxy group of 10
  • the “substituent” in the alkyl group of “C 5 to C 10 cycloalkyl group having a substituent” or “C 2 to C 6 linear or branched alkenyl group having a substituent” The thing similar to what was shown can be mentioned, and the aspect which can take can mention the same thing.
  • the “aromatic hydrocarbon group”, the “aromatic heterocyclic group” or the “fused polycyclic aromatic group” in the ring aromatic group is represented by Ar 1 to Ar 4 in the above general formula (1)
  • “aromatic” Group may be the same as those described with regard to “heterocyclic group” or “fused polycyclic aromatic group”, and these groups may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom
  • these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex
  • substituted aromatic hydrocarbon group represented by Ar 1 to Ar 4 in the above general formula (1)
  • substituted aromatic complex The same groups as those described for "substituent” in the "ring group” or “substituted fused polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible embodiments.
  • aryloxy group in the "substituted or unsubstituted aryloxy group” represented by R 1 to R 3 in the general formula (1) include a phenyloxy group, a biphenylyloxy group and a terphenyl group.
  • Ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc. can be mentioned, and these groups are single They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex
  • substituted aromatic hydrocarbon group represented by Ar 1 to Ar 4 in the above general formula (1)
  • substituted aromatic complex The same groups as those described for "substituent” in the "ring group” or “substituted fused polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible embodiments.
  • substituted or unsubstituted aromatic hydrocarbon group or “substituted or unsubstituted fused polycyclic aromatic group” is preferable, and a phenyl group and a naphthyl group are preferable.
  • a phenanthrenyl group and a fluorenyl group are more preferable, and a substituted phenyl group and a substituted fluorenyl group are particularly preferable.
  • a substituent of a phenyl group a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group, and a fluorenyl group are preferable, and as a substituent of a fluorenyl group, a methyl group and a phenyl group are preferable.
  • substituted or unsubstituted aromatic hydrocarbon group or “substituted or unsubstituted fused polycyclic aromatic group” is preferable, and a phenyl group, a biphenylyl group, A naphthyl group, a phenanthrenyl group, and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, and a fluorenyl group having a substituent are more preferable.
  • a substituent of a fluorenyl group a methyl group and a phenyl group are preferable.
  • R 1 and R 3 in the general formula (1) a hydrogen atom and a deuterium atom are preferable, and from the viewpoint of synthesis, a hydrogen atom is more preferable.
  • R 2 in the general formula (1) “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted fused polycyclic aromatic group” is preferable, and a phenyl group, a biphenylyl group, a naphthyl group, The phenanthrenyl group and the fluorenyl group are more preferable, and the unsubstituted phenyl group, the unsubstituted biphenylyl group, the unsubstituted naphthyl group, and the fluorenyl group having a substituent are more preferable.
  • a substituent of a fluorenyl group a methyl group and a phenyl group are preferable.
  • C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted represented by R 4 in the general formula (2), “even if it has a substituent” “C 1 to C 6 straight” in “C 5 to C 10 cycloalkyl group” or “C 2 to C 6 linear or branched alkenyl group which may have a substituent (s)”
  • the chain or branched alkyl group the “C 5 to C 10 cycloalkyl group” or the “C 2 to C 6 linear or branched alkenyl group”, a methyl group is specifically exemplified.
  • C1-C6 linear or branched alkyl group having a substituent which is represented by R 4 in the general formula (2)”, “cycloalkyl having a substituent having 5 to 10 carbon atoms”
  • Examples of the “substituent” in the group ”or“ a C 2 to C 6 linear or branched alkenyl group having a substituent ” specifically include a deuterium atom, a cyano group, a nitro group; Halogen atoms such as chlorine atom, bromine atom and iodine atom; C1-C6 linear or branched alkyloxy groups such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group and the like Alkenyl groups; aryloxy groups such as phenyloxy group and tolyloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group; An aromatic hydrocarbon group or a
  • C1-C6 linear or branched alkyloxy group having a substituent which is represented by R 4 in the general formula (2), or“ cyclo having 5 to 10 carbon atoms having a substituent ”
  • R 4 in the general formula (2)
  • cyclo having 5 to 10 carbon atoms having a substituent As the “substituent” in the alkyloxy group ”, a“ C 1 to C 6 linear or branched alkyl group having a substituent ”represented by R 1 to R 3 in the above general formula (1)
  • “Substituents” in “C 5 -C 10 cycloalkyl group having substituent (s)” or “C 2 -C 6 linear or branched alkenyl group having substituent (s)” The same thing can be mentioned as the same thing as the thing which can be mentioned.
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 4 in the general formula (2), or “substituted or unsubstituted fused polycyclic aromatic group
  • these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex
  • substituted aromatic hydrocarbon group represented by Ar 1 to Ar 4 in the above general formula (1)
  • substituted aromatic complex The same groups as those described for "substituent” in the "ring group” or “substituted fused polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible embodiments.
  • aryloxy group in the "substituted or unsubstituted aryloxy group” represented by R 4 in General Formula (2), a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group And naphthyloxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, indenyloxy, pyrenyloxy and perylenyloxy groups.
  • these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex
  • substituted aromatic hydrocarbon group represented by Ar 1 to Ar 4 in the above general formula (1)
  • substituted aromatic complex The same groups as those described for "substituent” in the "ring group” or “substituted fused polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible embodiments.
  • R 4 in the general formula (2) a hydrogen atom or a “substituted or unsubstituted aromatic hydrocarbon group” is preferable, a phenyl group and a naphthyl group are more preferable, and a non-substituted phenyl group is more preferable.
  • Ar 1, Ar 2 in the general formula (2) is the same as Ar 1, Ar 2 in the general formula (1).
  • a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group is more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl A group and a fluorenyl group having a substituent are more preferable.
  • a substituent of a fluorenyl group a methyl group and a phenyl group are preferable.
  • substituted or unsubstituted alkyl group having 1 to 15 carbon atoms represented by R 5 to R 14 and Ra in the general formula (HOST-A) include a methyl group, an ethyl group and a propyl group.
  • Examples of the “substituent” in the “substituted or unsubstituted C 1 to C 15 alkyl group” represented by R 5 to R 14 and Ra in the general formula (HOST-A) include Or a "C1-C6 linear or branched alkyl group having a substituent," a "C5-C10 cycloalkyl group having a substituent,” represented by R 1 to R 3 of Mention may be made of the same ones as described for the “substituent” in the “C2-C6 linear or branched alkenyl group having a substituent”, and the same possible embodiments are also exemplified. You can raise it.
  • substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R 5 to R 14 and Ra in the general formula (HOST-A)
  • a phenyl group a biphenylyl group, 1-naphthyl group, 2-naphthyl group, fluorophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group, pentafluorophenyl group, toluyl group, nitrophenyl group, cyanophenyl group, fluorobiphenylyl group, nitro And biphenylyl, cyanobiphenyl, cyanonaphthyl, nitronaphthyl, fluoronaphthyl and the like.
  • a phenyl group or a biphenylyl group is particularly preferred.
  • “Substituent” in “substituted or unsubstituted phenylene group”, “substituted or unsubstituted biphenylene group” or “substituted or unsubstituted terphenylene group” represented by L 1 in general formula (HOST-A) Is a “C1-C6 linear or branched alkyl group having a substituent,” a carbon atom having a substituent, represented by R 1 to R 3 in the general formula (1);
  • the same ones as described for the “substituent” in the “C 5 to C 10 cycloalkyl group” or “C 2 to C 6 linear or branched alkenyl group having a substituent” can be mentioned. The same can be mentioned as possible modes.
  • R 15 ⁇ R 18 The general formula (HOST-B) "alkyl group having 1 to 15 carbon atoms" represented by R 15 ⁇ R 18 being, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl Group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group , 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1 -Chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl
  • Examples of the “substituent” in the “C1-C15 alkyl group” represented by R 15 to R 18 in the general formula (HOST-B) are represented by R 1 to R 3 in the general formula (1).
  • “C1-C6 linear or branched alkyl group having a substituent,” “C5-C10 cycloalkyl group having a substituent,” or “number of carbon atoms having a substituent” The same groups as those described with respect to the “substituent” in the “2 to 6 linear or branched alkenyl group” can be mentioned, and the modes which can be taken also can be the same.
  • Specific examples of the “aryl group having 6 to 50 ring carbon atoms” or the “heteroaryl group having 4 to 50 ring carbon atoms” in the above “heteroaryl group” include a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.
  • anthryl group anthryl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, acetonaphthenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyranyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, Carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl , It can be exemplified benzoimidazolyl group, a dibenzofuranyl group, and dibenzothienyl group and the like.
  • Substituted or unsubstituted aryl ring group having 6 to 50 ring carbon atoms represented by R 15 to R 18 in the general formula (HOST-B), or “substituted ring or unsubstituted ring carbon atoms 4 to 50
  • the same groups as those described for "substituent” in "polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible modes.
  • examples of “an arylene group having 6 to 30 ring carbon atoms” or “a heteroarylene group having 5 to 30 ring carbon atoms” in ⁇ ” include a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group and an anthrylene group , Phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, acetonaphthenylene group, fluorantenylene group, triphenylenylene group, pyridinene group, pyranylene group, quinolylene group, isoquinolylene group, benzofuranylene group, benzothienylene
  • substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by Y in the general formula (HOST-B), or the “substituted or unsubstituted ring having 5 to 30 ring carbon atoms”
  • substituted aromatic hydrocarbon group represented by Ar 1 to Ar 4 in the general formula (1)
  • substituted aromatic heterocyclic group or “substituted fused polycyclic aromatic group”
  • Specific examples of the "aryl group having 6 to 30 ring carbon atoms” or the “heteroaryl group having 5 to 30 ring carbon atoms” in the group include phenyl group, naphthyl group, anthracenyl group, phenanthryl group and biphenyl group P-terphenyl group, m-terphenyl group, quaternary phenyl group, fluorenyl group, triphenylene group, biphenylene group, pyrenyl group, benzofluoranthenyl group, chrysenyl group, phenylnaphthyl group, naphthylphenyl group, pyridyl group
  • Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar 7 in the general formula (HOST-B), or “heteroaryl having substituted or unsubstituted ring atoms having 5 to 30 ring carbon atoms”
  • the“ substituted aromatic hydrocarbon group ”represented by Ar 1 to Ar 4 in the general formula (1) the“ substituted aromatic heterocyclic group ”or the“ substituted fused polycyclic aromatic ring
  • the same thing as what was shown about "substituent” in "group group” can be mentioned, and the aspect which can take can mention the same thing.
  • C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted represented by R 19 to R 34 in the general formula (3), “having a substituent” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)”
  • the linear or branched alkyl group of 6 are specifically mentioned Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopent
  • C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted represented by R 19 to R 34 in the general formula (3), “having a substituent”
  • substituents in the "optionally substituted C5-C10 cycloalkyl group” or “optionally substituted C2-C6 linear or branched alkenyl group” Is a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent, which is represented by R 1 to R 3 in the general formula (1), or a group having 5 carbon atoms having a substituent
  • the same ones as described for "substituent” in "C.sub.10 cycloalkyl group” or “C.sub.2-C 6 linear or branched alkenyl group having substituent (s)” may be mentioned. The same is true for the It is possible.
  • methyloxy group, ethyloxy group, n-propyloxy group isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group , Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Or the like can be raised to the group.
  • C1-C6 linear or branched alkyloxy group having a substituent or a substituted alkyl oxy group represented by R 19 to R 34 in the general formula (3)
  • R 19 to R 34 in the general formula (3)
  • a “C1-C6 linear or branched C1-C6 carbon atom having a substituent” represented by R 1 to R 3 in the general formula (1) is preferable.
  • the “substituent” in the alkyl group of “C 5 to C 10 cycloalkyl group having a substituent” or “C 2 to C 6 linear or branched alkenyl group having a substituent” The thing similar to what was shown can be mentioned, and the aspect which can take can mention the same thing.
  • aryloxy group in the "substituted or unsubstituted aryloxy group” represented by R 19 to R 34 in the general formula (3) include a phenyloxy group, a biphenylyloxy group and a terphenyl group.
  • Ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc. can be mentioned, and these groups are single They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the “substituent” in the “substituted or unsubstituted aryloxy group” represented by R 19 to R 34 in the general formula (3) is represented by R 1 to R 3 in the general formula (1)
  • the same groups as those described for the "substituent” in the “substituted or unsubstituted aryloxy group” can be mentioned, and the same can be mentioned as possible modes.
  • the "aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the polycyclic aromatic group include phenyl group, naphthyl group, anthracenyl group, phenanthryl group, Naphthalsenyl group, pyrenyl group, biphenylyl group, p-terphenyl group, m-terphenyl group, chrysenyl group, triphenylenyl group, perylenyl group, indenyl group, furanyl group, thiophenyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group , Oxazolyl group, thiazolyl
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 19 to R 34 in the general formula (3), or “substituted or unsubstituted condensation
  • the “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the general formula (1), the “substituted aromatic heterocyclic group” or the “substituted group” as the “substituent” in the polycyclic aromatic group ” The same groups as those described for "substituent” in the "fused polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible modes.
  • aromatic hydrocarbon group aromatic hydrocarbon group
  • aromatic hydrocarbon group aromatic heterocyclic group
  • fused polycyclic aromatic group examples include the compounds represented by the general formula (1) The same as the “substituents” in “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” represented by Ar 1 to Ar 4 in The thing which can be mentioned and the aspect which can take can mention the same thing.
  • “condensed polycyclic aromatic group” specifically includes phenyl group, biphenylyl group, terphenylyl group, tetrakisphenyl group, styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group And groups such as pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group.
  • aromatic heterocyclic group in the “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 11 in the structural formula (5) include a triazinyl group, a pyridyl group and a pyrimidinyl group, Furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group And dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, carborinyl group and the like.
  • a C1-C6 linear or branched alkyl group represented by R 35 to R 38 in the structural formula (5) include a methyl group, an ethyl group and an n- group.
  • Propyl, i-propyl, n-butyl, 2-methylpropyl, t-butyl, n-pentyl, 3-methylbutyl, tert-pentyl, n-hexyl, iso-hexyl and tert -A hexyl group can be mentioned.
  • Specific examples of the "aromatic hydrocarbon group", “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the polycyclic aromatic group include phenyl group, biphenylyl group, terphenylyl group, tetrakisphenyl group , Styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrol
  • a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group and a triphenylenyl group are more preferable.
  • the phenyl group preferably has a substituted or non-substituted fused polycyclic aromatic group as a substituent, and is selected from a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group and a triphenylenyl group. It is more preferable to have a substituted substituent.
  • a phenyl group having a substituent is preferable, and as the substituent in this case, an aromatic hydrocarbon group such as phenyl group, biphenylyl group, terphenyl group, naphthyl group, anthracenyl group And fused polycyclic aromatic groups such as acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group are preferable, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, Pyrenyl group, fluoranthenyl group and triphenylenyl group are more preferable.
  • an aromatic hydrocarbon group such as phenyl group, biphenylyl group, terphenyl group, naphthyl group, anthracenyl group
  • fused polycyclic aromatic groups such as
  • a phenyl group having a substituent is preferable, and as the substituent in this case, an aromatic hydrocarbon group such as phenyl group, biphenylyl group, terphenyl group, naphthyl group, anthracenyl group And fused polycyclic aromatic groups such as acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group are preferable, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, Pyrenyl group, fluoranthenyl group and triphenylenyl group are more preferable.
  • an aromatic hydrocarbon group such as phenyl group, biphenylyl group, terphenyl group, naphthyl group, anthracenyl group
  • fused polycyclic aromatic groups such as
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 12 , Ar 13 and V 1 in the general formula (6)
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 12 , Ar 13 and V 1 in the structural formula (6)
  • the linear or branched alkyl group specifically, Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexene group Groups such
  • C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted represented by V 1 in the general formula (6), or “having a substituent”
  • substituents in the good cycloalkyl group having 5 to 10 carbon atoms or “a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent (s)”
  • R 1 to R 3 in the formula (1) “ a 5- to 10-carbon atom having a substituent
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 39 to R 44 in the general formula (7), “having a substituent” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)”
  • the linear or branched alkyl group of 6 are specifically mentioned Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopenty
  • C1-C6 linear or branched alkyl group having a substituent which is represented by R 39 to R 44 in the general formula (7),“ c-5 having a substituent ”
  • Specific examples of the "substituent" in the cycloalkyl group of "" or “C2-C6 linear or branched alkenyl group having a substituent” include deuterium atom, cyano group, nitro group; A halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group An alkenyl group such as a phenyl group, an aryloxy group such as a tolyloxy group, an arylalkyloxy group such as a benzyloxy group or a phenethyloxy group; Aromatic hydro
  • methyloxy group, ethyloxy group, n-propyloxy group isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group , Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Etc.
  • groups can be mentioned groups, these groups to each other is a single bond, a substituted or unsubstituted methylene group, via an oxygen atom or a sulfur atom may bond to each other to form a ring.
  • these groups may have a substituent, and as the substituent, “a linear group having 1 to 6 carbon atoms having a substituent, represented by R 39 to R 44 in the general formula (7), Or branched or branched alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, or a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms Examples similar to those described for the "substituent" can be mentioned, and the possible embodiments can also be mentioned the same.
  • aromatic hydrocarbon group “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the ring aromatic group
  • phenanthrenyl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofur
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 39 to R 44 in the general formula (7), or “substituted or unsubstituted fused multiple ring”
  • substituents in the "ring aromatic group” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl group, n -C1-C6 linear or branched, such as -propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl and the like Alkyl groups having 1 to 6 carbon atoms, such as methyloxy, ethyloxy, prop
  • aryloxy group in the "substituted or unsubstituted aryloxy group” represented by R 39 to R 44 in the general formula (7) include a phenyloxy group, a biphenylyloxy group and a terphenyl group.
  • Ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc. can be mentioned, and these groups are single They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • the “substituent” in the “substituted or unsubstituted aryloxy group” represented by R 39 to R 44 in the general formula (7) is represented by R 1 to R 3 in the general formula (1)
  • the same groups as those described for the "substituent” in the “substituted or unsubstituted aryloxy group” can be mentioned, and the same can be mentioned as possible modes.
  • r 1 to r 6 may be the same or different, r 1 to r 4 represent an integer of 0 to 5, and r 5 and r 6 represent an integer of 0 to 4.
  • R 39 to R 44 bound to a plurality of identical benzene rings may be identical to each other They may be different from each other, and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • C5-C10 cycloalkylene group ;
  • vinylene group, allylene group, isopropenylene group, butenylene group” and the like C2-C6 linear or branched alkenylene group”;
  • benzene Of two hydrogen atoms from aromatic hydrocarbons such as biphenyl, terphenyl and tetrakisphenyl
  • Divalent group of aromatic hydrocarbon “condensed polycyclic aromatics” obtained by removing two hydrogen atoms from fused polycyclic aromatics such as naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene, indane, pyrene and triphenylene It is possible to cite bivalent groups such as “group bivalent group”.
  • these bivalent groups may have a substituent.
  • C1-C6 linear or branched alkylene group "C5-C10 cycloalkylene group” or “C2-C6 linear or branched alkenylene group”
  • substituent of “a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent” represented by R 39 to R 44 in the general formula (7) “having a substituent” Examples similar to those described for "substituent” in "C5-C10 cycloalkyl group” or "C2-C6 linear or branched alkenyl group having substituent group” Can.
  • the “6 linear or branched alkyl group” “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group”
  • C1-C6 linear or branched alkyl group having a substituent which is represented by R 45 to R 56 in the general formula (8),“ c-5 having a substituent ”
  • R 45 to R 56 in the general formula (8)
  • C2-C6 linear or branched alkenyl group having a substituent examples of the “substituent” in the “cycloalkyl group” or the “C2-C6 linear or branched alkenyl group having a substituent” are R 39 to R 44 in the general formula (7).
  • C1-C6 linear or branched alkyloxy group having a substituent represented by R 45 to R 56 in the general formula (8), or“ c5-C having a substituent ”
  • the same as those described for "substituent” in "alkyloxy group” or "C5-C10 cycloalkyloxy group having a substituent” can be exemplified, and the possible embodiments are also the same You can raise
  • the “aromatic hydrocarbon group”, the “aromatic heterocyclic group” or the “fused polycyclic aromatic group” in the ring aromatic group is represented by R 39 to R 44 in the general formula (7)
  • “aromatic” Group may be the same as those described with regard to “heterocyclic group” or “fused polycyclic aromatic group”, and these groups may be a single bond, a substituted or unsubstituted methylene group, an
  • Examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R 45 to R 56 in the general formula (8) are represented by R 39 to R 44 in the general formula (7).
  • the same as those described for the "aryloxy group” in the “substituted or unsubstituted aryloxy group” can be mentioned, and the same can be mentioned as possible embodiments.
  • r 7 to r 18 may be the same or different, r 7 to r 12 represent an integer of 0 to 5, and r 13 to r 18 represent an integer of 0 to 4.
  • R 45 to R 56 bonded to the same benzene ring may be identical to each other They may be different from each other, and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Examples of the “divalent linking group” represented by K 2 , K 3 and K 4 in the general formula (8) include “bivalent linking group” represented by K 1 in the general formula (7). The same thing can be mentioned as what was shown about, and the aspect which can take can mention the same thing.
  • the arylamine compound represented by the general formula (1) of the present embodiment is a novel compound, and has an excellent ability to trap triplet excitons and excellent hole transport than conventional hole transport materials. Active, has excellent amorphous property, and is stable in thin film state.
  • the arylamine compound represented by General formula (1) of this embodiment can be used as a host material of the 2nd positive hole transport layer adjacent to the light emitting layer of an organic EL element, and / or a light emitting layer. It is possible to confine excitons generated in the light emitting layer by using a material that has high hole injection property, high mobility, high electron blocking property, and high electron stability compared to conventional materials. it can. As a result, the probability that holes and electrons recombine can be further improved, and high luminous efficiency can be obtained. At the same time, the driving voltage is lowered, and the durability of the organic EL element is improved.
  • the arylamine compound represented by General formula (1) of this embodiment can also be used as a constituent material of the light emitting layer of an organic EL element.
  • the said compound is excellent in hole transportability compared with the conventional material, and when it contains a green phosphorescence light emitting material especially, it has the effect
  • the organic EL device of the present embodiment has hole mobility larger than that of the conventional hole transport material, has excellent electron blocking ability, has excellent amorphous property, and has electric reduction durability. An excellent arylamine compound is used. Therefore, high efficiency and high durability can be realized.
  • the above-described arylamine compound can be synthesized according to a method known per se (see, for example, Patent Document 8). For example, as shown in Examples described later, a disubstituted amine and a halogenated substituted aromatic hydrocarbon are reacted by a coupling reaction, and the resulting compound is further halogenated to obtain a boronic acid of an aromatic hydrocarbon.
  • the arylamine compounds described above can be synthesized by reacting them with a coupling reaction.
  • the above-mentioned compound having a nitrogen-containing heteroaromatic ring structure can be synthesized according to a method known per se (see, for example, Patent Documents 4 and 5).
  • the compounds having a carbazole-containing structure described above can be synthesized according to a method known per se (see, for example, Patent Documents 4 and 5).
  • the above-mentioned iridium complex can be synthesized according to a method known per se (see, for example, Patent Documents 9 and 10).
  • the compounds having a pyrimidine ring structure described above can be synthesized by a method known per se (see, for example, Patent Documents 10 and 11).
  • triphenylamine derivatives represented by the above general formula (7) which are suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is not limited to these compounds. It is not limited.
  • triphenylamine derivatives represented by the general formula (8) which are suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is not limited to these compounds. It is not limited.
  • the compound having a triarylamine structure described above can be synthesized according to a method known per se (see, for example, Patent Documents 1, 2 and 15).
  • Purification of the general formulas (1) to (8), (HOST-A) and (HOST-B) is purification by column chromatography, adsorption purification with silica gel, activated carbon, activated clay or the like, recrystallization or crystallization method with a solvent, It can be performed by a sublimation purification method or the like. Identification of compounds can be done by NMR analysis. As physical property values, measurement of melting point, glass transition point (Tg) and work function is performed. The melting point is an index of vapor deposition property, the glass transition point (Tg) is an index of stability of the thin film state, and the work function is an index of hole transporting property or hole blocking property.
  • the melting point and the glass transition point (Tg) can be measured using a powder by a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS).
  • the work function can be obtained by preparing a thin film of 100 nm on an ITO substrate and using an ionization potential measurement device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).
  • T1 of these compounds can be calculated from the measured phosphorescence spectrum.
  • the phosphorescence spectrum can be measured using a commercially available spectrophotometer.
  • a general method of measuring the phosphorescence spectrum is a method of dissolving in a solvent and irradiating it with excitation light at low temperature (for example, see Non-Patent Document 3), or depositing it on a silicon substrate to form a thin film
  • There is a method of measuring excitation light and measuring a phosphorescence spectrum see, for example, Patent Document 16).
  • T1 can be calculated by reading the wavelength of the first peak on the short wavelength side of the phosphorescence spectrum or the wavelength of the rising position on the short wavelength side and converting it into the energy value of light according to the following equation.
  • T1 is an indicator of the trapping ability of the triplet exciton of the phosphorescence material.
  • E is the light energy value
  • h Planck's constant (6.63 ⁇ 10 -34 Js)
  • c is the speed of light (3.00 ⁇ 10 8 m / s)
  • ⁇ is the short wavelength of the phosphorescence spectrum Represents the wavelength (nm) at which the side rises. Then, 1 eV is 1.60 ⁇ 10 ⁇ 19 J.
  • the structure of the organic EL device of the present embodiment includes, in order on the substrate, an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and What has a cathode laminated
  • two or more organic layers having the same function can be stacked, or two light emitting layers can be stacked, or two electron transporting layers can be stacked.
  • an electrode material having a large work function such as ITO or gold is used.
  • an electrode material having a large work function such as ITO or gold
  • the hole injection layer of the organic EL device of the present embodiment in addition to the arylamine compounds represented by the general formulas (7) and (8), porphyrin compounds represented by copper phthalocyanine, triburst of starburst type Amine derivatives, acceptor heterocyclic compounds such as hexacyanoazatriphenylene and coated polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
  • the arylamine compounds represented by the general formulas (7) and (8) are more preferable, and in addition, N, N′-diphenyl-N, N'-di (m-tolyl) -benzidine (hereinafter abbreviated as TPD), N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) -benzidine (hereinafter abbreviated as NPD), N Benzidine derivatives such as N, N ', N'-tetrabiphenylyl benzidine, 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), and the like can also be used.
  • TPD N, N′-diphenyl-N, N'-di (m-tolyl) -benzidine
  • NPD N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl)
  • these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed by independently forming the above-mentioned plurality of materials, and the above-mentioned plurality of materials.
  • a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a plurality of the above materials alone may be employed.
  • a coating type such as poly (3,4-ethylenedioxythiophene) (hereinafter referred to as PEDOT) / poly (styrene sulfonate) (hereinafter referred to as PSS), etc.
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS poly (styrene sulfonate)
  • PSS polymer materials
  • trisbromophenylamine hexachloroantimony, a radialene derivative for example, a compound (Acceptor-1) described later
  • a patent document in addition to materials generally used in the layer. 17 may be P-doped, and a polymer compound having a structure of a benzidine derivative such as TPD in its partial structure may be used.
  • TCTA N-carbazolyl Triphenylamine
  • mCP 9,9-bis [4- (carbazol-9-yl) phenyl] fluorene
  • mCP 1,3-bis (carbazol-9-yl) benzene
  • Ad-Cz Carbazole derivatives such as 2, 2-bis (4-carbazol-9-ylphenyl) adamantane
  • Ad-Cz 9- [4- (carbazol-9-yl) phenyl] -9
  • Compound having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure represented by-[4- (triphenylsilyl) phenyl] -9H-fluoren
  • These layers may be formed separately, but may be used as a single layer formed by mixing with other materials, layers formed separately, layers formed by mixing, or layers A stacked structure of a layer formed separately and a layer formed by mixing may be employed.
  • These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
  • a hole transporting host material or an electron transporting host material can be used as a host of the light emitting layer of the organic EL device of the present embodiment.
  • a hole transporting host material or an electron transporting host material can be used.
  • carbazole derivatives such as 4,4'-di (N-carbazolyl) biphenyl (CBP), TCTA, mCP and the like.
  • p-bis (triphenylsilyl) benzene (UGH2) or 2 in addition to the compound having a nitrogen-containing heteroaromatic ring structure represented by the above general formula (HOST-A) 2 ′, 2 ′ ′-(1,3,5-phenylene) -tris (1-phenyl-1H-benzimidazole) (TPBi) can be used.
  • HOST-A triphenylsilyl
  • TPBi (1-phenyl-1H-benzimidazole)
  • first host compound having an electron transporting ability it is preferable to use two or more compounds of a first host compound having an electron transporting ability and a second host compound having a hole transporting ability.
  • One or two or more species of the second host compound may be used.
  • the first host compound and the second host compound may be contained, for example, in a weight ratio of 1:10 to 10: 1.
  • the first host compound of the light emitting layer of the organic EL device of the present embodiment a compound having a nitrogen-containing heteroaromatic ring structure represented by the general formula (HOST-A) is preferable, and as the second host compound
  • the compound is preferably a compound having a carbazole ring structure represented by the general formula (HOST-B) or an arylamine compound represented by the general formula (1) of the present embodiment.
  • one or more host compounds can be further included.
  • the iridium complex represented by the general formula (3) of this embodiment is more preferable as the phosphorescent light emitting material of the organic EL element of this embodiment, but in addition, Pt, Os, Ti, Zr, Hf, Eu, Tb Organometallic compounds comprising Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof can be used.
  • the dopant may be a red, green or blue dopant, and a high performance organic EL device can be produced.
  • These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
  • the benzoazole compounds and pyrimidine compounds represented by the general formulas (4) and (6) are more preferable, but in addition, vasocuproin (hereinafter abbreviated as BCP)
  • BCP vasocuproin
  • phenanthroline derivatives such as
  • metal complexes of quinolinol derivatives such as BAlq
  • various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and other compounds having a hole blocking function can be used. It may double as a material.
  • these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed by independently forming the above-mentioned plurality of materials, and the above-mentioned plurality of materials.
  • a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a plurality of the above materials alone may be employed.
  • These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
  • benzoazole compounds and pyrimidine compounds represented by the above general formulas (4) and (6) are more preferable, but in addition, Alq 3 , BAlq, compounds to be described later
  • Other metal complexes of quinolinol derivatives including ETM-1), various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, Pyridoindole derivatives, phenanthroline derivatives, silole derivatives and the like can also be used.
  • these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed by independently forming the above-mentioned plurality of materials, and the above-mentioned plurality of materials.
  • a stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a plurality of the above materials alone may be employed.
  • These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
  • alkali metal salts such as lithium fluoride and cesium fluoride
  • alkaline earth metal salts such as magnesium fluoride
  • metal complexes of quinolinol derivatives such as lithium quinolinol, aluminum oxide and the like
  • Metal oxides of the above can be used, but this can be omitted in the preferred selection of the electron transport layer and the cathode.
  • organic compounds commonly used in the layer may be further N-doped with a metal such as cesium, lithium fluoride and ytterbium.
  • an electrode material having a low work function such as aluminum or ytterbium, or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy as an electrode material Used.
  • 2-yl) -amine To 10.0 g, toluene: 80 mL, ethanol: 40 mL, phenylboronic acid: 2.1 g, followed by an aqueous solution previously dissolving 5.9 g of potassium carbonate in 30 mL of H 2 O Nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. 0.3 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 5 hours while heating under reflux. After cooling, EtOAc and H 2 O were added, and the organic layer was extracted by liquid separation operation and concentrated under reduced pressure to obtain a crude product.
  • Naphthyl-2-yl) -phenyl) ⁇ -amine 10.0 g
  • toluene 70 mL
  • ethanol 30 mL
  • phenylboronic acid 2.7 g
  • potassium carbonate 6.1 g H 2 O: 20 mL
  • the aqueous solution dissolved in was added, and nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes.
  • 0.3 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 24 hours while heating under reflux. After allowing to cool, methanol was added and the precipitated solid was collected to obtain a crude product.
  • Phenyl) ⁇ -amine To 15.0 g of toluene: 160 mL, ethanol: 40 mL, phenylboronic acid: 3.0 g, followed by an aqueous solution previously dissolving 5.7 g of potassium carbonate in 40 mL of H 2 O Nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. 0.5 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 21 hours while heating under reflux. After allowing to cool, the organic layer was collected by liquid separation operation. The residue was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product.
  • the glass transition point of the arylamine compound represented by the general formula (1) was determined by a high sensitivity differential scanning calorimeter (DSC3100S, manufactured by Bruker AXS). Glass transition point Compound of Example 1 110 ° C. Compound of Example 2 121 ° C. Compound of Example 3 135 ° C. Compound of Example 4 140 ° C. Compound of Example 5: 115 ° C. Compound of Example 6 121 ° C.
  • the arylamine compound represented by the general formula (1) has a glass transition point of 100 ° C. or more, which indicates that the thin film state is stable.
  • the compounds of Examples 1 to 6 show favorable energy levels as compared with the work function 5.4 eV of common hole transport materials such as NPD, TPD, etc. It can be seen that it has a hole transport capacity.
  • the compound used in the present disclosure has a value larger than T1 of tri (m-terphenyl-4-yl) amine (HTM-2) which is a commonly used hole transport material.
  • HTM-2 tri (m-terphenyl-4-yl) amine
  • the two phenyl groups substituted in the meta position to the nitrogen atom of the triarylamine cause a large twist in the backbone around the amine, and the phenyl group substituted in the para position to the nitrogen atom as a large sterically hindered group
  • the compounds used in the present disclosure achieve higher T1 than HTM-2.
  • the compound used in the present disclosure has a value larger than T1 possessed by tris (4-methyl-2,5-diphenylpyridine) iridium (III) (compound 3-3) which is a green phosphorescent light-emitting material, It has the ability to sufficiently confine triplet excitons excited in the light emitting layer.
  • the organic EL device has a hole injection layer 3, a first hole transport layer 4, and a second hole transport on a glass substrate 1 on which an ITO electrode is formed in advance as a transparent anode 2.
  • the layer 5, the light emitting layer 6, the electron transport layer 7, the electron injection layer 8, and the cathode (aluminum electrode) 9 were produced by vapor deposition in this order.
  • the glass substrate 1 on which ITO having a film thickness of 150 nm was formed was subjected to ultrasonic cleaning for 20 minutes in isopropyl alcohol and then dried for 10 minutes on a hot plate heated to 200.degree. Thereafter, UV ozone treatment was carried out for 15 minutes, and then the ITO-attached glass substrate was mounted in a vacuum deposition machine, and the pressure was reduced to 0.001 Pa or less.
  • a compound Acceptor-1 of the following structural formula and a compound (7-3) are formed as a hole injection layer 3 so as to cover the transparent anode 2, and the deposition rate ratio is Acceptor-1:
  • Compound (7-3) Binary vapor deposition was performed on the transparent anode 2 at a vapor deposition rate of 3:97, and the hole injection layer 3 was formed to have a film thickness of 10 nm.
  • the compound (7-3) was vapor-deposited as the first hole transport layer 4 on the hole injection layer 3 to a film thickness of 70 nm.
  • the compound (1-2) of Example 2 was vapor deposited as the second hole transport layer 5 on the first hole transport layer 4 so as to have a film thickness of 10 nm.
  • the first host compound (A-19) and the second host compound (B-22) are simultaneously used as a light emitting layer 6 as a host, and the iridium compound (d The compound was vacuum deposited to a film thickness of 40 nm by doping 3-3 wt% to 5 wt%.
  • the first host compound (A-19) and the second host compound (B-22) were used at a ratio of 1: 1.
  • the compound (4-78) having a deposition rate ratio of the compound (4-78): ETM is used as the electron transport layer 7 and the compound (4-78) of the following structural formula and the compound ETM-1 of the following structural formula.
  • Lithium fluoride was vapor-deposited as the electron injection layer 8 to a film thickness of 1 nm on the electron transport layer 7.
  • aluminum was vapor deposited on the electron injection layer 8 to a thickness of 100 nm to form a cathode 9.
  • Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 10 except that the compound (6-1) was used instead of the compound (4-78) as the material of the electron transport layer 7.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Example 10 is the same as Example 10 except that the compound (1-3) of Example 3 is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 12, except that the compound (6-1) was used instead of the compound (4-78) as the material of the electron transport layer 7.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Example 10 is repeated except that the compound (1-4) of Example 4 is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5 Made.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 14, except that the compound (6-1) was used instead of the compound (4-78) as the material of the electron transport layer 7.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 10 except that the compound (1-2) of Example 2 was used instead of the compound (B-22) as the second host material.
  • the first host compound (A-19) and the second host compound (1-2) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 11 except that the compound (1-2) of Example 2 was used instead of the compound (B-22) as the second host material.
  • the first host compound (A-19) and the second host compound (1-2) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 12 except that the compound (1-3) of Example 3 was used instead of the compound (B-22) as the second host material.
  • the first host compound (A-19) and the second host compound (1-3) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 13, except that the compound (1-3) of Example 3 was used instead of the compound (B-22) as the second host material.
  • the first host compound (A-19) and the second host compound (1-3) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 14, except that the compound (1-4) of Example 4 was used instead of the compound (B-22) as the second host material.
  • the first host compound (A-19) and the second host compound (1-4) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • An organic EL device was produced in the same manner as in Example 15 except that the compound (1-4) of Example 4 was used instead of the compound (B-22) as the second host material.
  • the first host compound (A-19) and the second host compound (1-4) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Comparative Example 1 For comparison, in the same manner as in Example 10, except that the compound (HTM-2) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, an organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Comparative Example 2 For comparison, in the same manner as in Example 11, except that the compound (HTM-2) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, an organic EL device was obtained. Was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Example 10 For comparison, in Example 10, a compound (B-22) of the following structural formula was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5. The organic EL device was manufactured. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Comparative Example 4 For comparison, in the same manner as in Example 11, except that the compound (B-22) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, an organic EL device was obtained. Was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Example 14 the compound (HTM-2) is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, and Example 2 as the second host material.
  • An organic EL device was produced in the same manner except that the compound (HTM-2) was used instead of the compound (1-2).
  • the first host compound (A-19) and the second host compound (HTM-2) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • Example 15 the compound (HTM-2) is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, and Example 2 as the second host material.
  • An organic EL device was produced in the same manner except that the compound (HTM-2) was used instead of the compound (1-2).
  • the first host compound (A-19) and the second host compound (HTM-2) were used at a ratio of 1: 1.
  • the characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
  • the device life was measured using the organic EL devices produced in Examples 10 to 21 and Comparative Examples 1 to 6, and the results are shown in Table 1. Element life, when the emission start time of the emission luminance (initial luminance) was driven with a constant current as 10000 cd / m 2, equivalent to 95% when the emission luminance is taken as 100% of 9500cd / m 2 (initial luminance: The time to decay to 95%) was measured.
  • the luminous efficiency when passing a current density of 10 mA / cm 2 is 72.06 to 73. of the organic EL elements of Comparative Examples 1 to 4.
  • the efficiency was as high as 76.05 to 78.00 cd / A in the organic EL elements of Examples 10 to 15 with respect to 03 cd / A.
  • the organic EL elements of Examples 10 to 15 are as high as 57.31 to 58.99 lm / W, compared with 52.00 to 53.27 lm / W of the organic EL elements of Comparative Examples 1 to 4. It was efficient.
  • the element life (95% attenuation) was 341 to 400 hours for the organic EL elements of Comparative Examples 1 to 4, but 461 to 585 hours for the organic EL elements of Examples 10 to 15, It can be seen that the service life is greatly extended.
  • the current density is 10 mA /
  • the luminous efficiency when a current of 2 cm 2 was passed was 73.98 to 76 for the organic EL devices of Examples 16 to 21, compared to 63.74 to 73.03 cd / A for the organic EL devices of Comparative Examples 3 to 6.
  • the efficiency was as high as .04 cd / A.
  • the organic EL elements of Examples 16 to 21 are as high as 55.53 to 56.32 Im / W, compared with 45.93 to 53.27 Im / W of the organic EL elements of Comparative Examples 3 to 6 It was efficient.
  • the element life (95% attenuation) was 309 to 384 hours for the organic EL elements of Comparative Examples 3 to 6, while it was 408 to 480 hours for the organic EL elements of Examples 16 to 21, It can be seen that the service life is greatly extended.
  • an organic EL device comprising the light emitting layer using both the first host material having high electron transporting ability and the second host material having hole transporting ability, which is an aryl of the present disclosure
  • the organic EL device using the amine compound as the material of the second hole transport layer is improved in power efficiency as compared with the organic EL device using the compound (HTM-2) which is also the arylamine compound, It turned out that long life can be achieved. This is due to the fact that the arylamine compound of the present disclosure has a value greater than T1 of HTM-2.
  • the organic EL device using the arylamine compound of the present disclosure is capable of sufficiently confining triplet excitons excited in the light emitting layer, as compared to the organic EL device using HTM-2.
  • an organic EL element is realized in which the lifetime characteristics are significantly improved simultaneously with the improvement of the efficiency characteristics. It was also found that the power efficiency can be improved and the life can be extended even when compared with the organic EL device using the compound (B-22) which is a carbazole derivative as a material of the second hole transport layer.
  • the compound (B-22) which is a carbazole derivative as a material of the second hole transport layer.
  • the power efficiency can be improved as compared with the organic EL device using the compound (HTM-2), which is also the arylamine compound. It turned out that long life can be achieved.
  • the arylamine compound of the present disclosure has a value larger than T 1 possessed by the above-mentioned compound (compound 3-3) which is a green phosphorescent light-emitting material, and an excited triplet exciton is obtained even when used as a second host material It can be confined enough.
  • HTM-2 has low T1 and insufficient confinement of triplet excitons, and the deactivation of the excited triplet excitons significantly reduces the luminous efficiency and the device lifetime. It was also found that the improvement of the power efficiency and the prolongation of the life can be achieved as compared with the above-mentioned compound (B-22) which is a carbazole derivative.
  • B-22 which is a carbazole derivative.
  • the organic EL device of the present invention is improved in luminous efficiency and greatly improved in durability. For example, it has become possible to develop home appliances and lighting applications.

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Abstract

An organic EL device which at least comprises, between an anode and a cathode, a first hole transport layer, a second hole transport layer, a green light emission layer and an electron transport layer in this order from the anode side, wherein at least one layer disposed between the first hole transport layer and the electron transport layer contains an arylamine compound represented by general formula (1).

Description

アリールアミン化合物および有機エレクトロルミネッセンス素子Arylamine compounds and organic electroluminescent devices
　本発明は、各種の表示装置に好適な自発光素子である有機エレクトロルミネッセンス素子（以後、有機ＥＬ素子と略称する）に適した化合物と該素子に関するものであリ、詳しくはアリールアミン化合物と、該化合物を用いた有機ＥＬ素子に関するものである。 The present invention relates to a compound suitable for an organic electroluminescent device (hereinafter referred to as an organic EL device), which is a self-luminous device suitable for various display devices, and to the device, specifically an arylamine compound, The present invention relates to an organic EL device using the compound.
　有機ＥＬ素子は自己発光性素子であるため、液晶素子にくらべて明るく視認性に優れ、鮮明な表示が可能であるため、活発な研究がなされてきた。 Since the organic EL element is a self-light emitting element, it is brighter than the liquid crystal element and has excellent visibility and clear display, so active research has been conducted.
　１９８７年にイーストマン・コダック社のＣ．Ｗ．Ｔａｎｇらは各種の役割を各材料に分担した積層構造素子を開発することにより有機材料を用いた有機ＥＬ素子を実用的なものにした。彼らは電子を輸送することのできる蛍光体、トリス（８－ヒドロキシキノリン）アルミニウム（以後、Ａｌｑ３と略称する）と正孔を輸送することのできる芳香族アミン化合物とを積層し、両方の電荷を蛍光体の層の中に注入して発光させることにより、１０Ｖ以下の電圧で１０００ｃｄ／ｍ２以上の高輝度を得た（例えば、特許文献１および特許文献２参照）。 In 1987, Eastman Kodak Company C.I. W. Tang et al. Made the organic EL device using the organic material practical by developing a laminated structure device in which various functions are shared by the respective materials. They stack a phosphor capable of transporting electrons, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ) and an aromatic amine compound capable of transporting holes, and both charge Were injected into the phosphor layer to cause light emission, and a high luminance of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
　現在まで、有機ＥＬ素子の実用化のために多くの改良がなされ、各種の役割をさらに細分化して、基板上に順次に、陽極、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層、陰極を設けた電界発光素子によって高効率と耐久性が達成されている（例えば、非特許文献１参照）。 Up to the present, many improvements have been made for practical use of organic EL elements, and various roles are further subdivided, and on the substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport in sequence. High efficiency and durability are achieved by an electroluminescent device provided with a layer, an electron injection layer, and a cathode (see, for example, Non-Patent Document 1).
　また発光効率の更なる向上を目的として三重項励起子の利用が試みられ、燐光発光体の利用が検討されている（例えば、非特許文献２参照）。 In addition, utilization of triplet excitons has been attempted for the purpose of further improvement of luminous efficiency, and utilization of phosphorescent emitters has been studied (see, for example, Non-Patent Document 2).
　発光層は、一般的にホスト材料と称される電荷輸送性の化合物に、蛍光体や燐光発光体をドープして作製することもできる。近年では、燐光発光材料としてイリジウム錯体を用い、ホスト材料としてカルバゾール構造を有する化合物を用いた高効率の有機ＥＬ素子が提案されている（例えば、特許文献３）。 The light emitting layer can also be manufactured by doping a phosphor or a phosphorescence emitting material to a charge transporting compound generally called a host material. In recent years, a highly efficient organic EL device has been proposed which uses an iridium complex as a phosphorescent material and a compound having a carbazole structure as a host material (for example, Patent Document 3).
　さらにホストに電子輸送能が高い含窒素ヘテロ芳香族環構造を有する化合物と、正孔輸送能を有するカルバゾール構造を有する化合物を共に使用することによって、単独で使用された場合と比較して電子および正孔の輸送性が高まり発光効率が顕著に改善されている（例えば、特許文献４および特許文献５参照）。 Furthermore, by using together a compound having a nitrogen-containing heteroaromatic ring structure having a high electron transporting ability as a host and a compound having a carbazole structure having a hole transporting ability, electrons and electrons are compared with those used alone. The hole transportability is enhanced and the light emission efficiency is significantly improved (see, for example, Patent Document 4 and Patent Document 5).
　これまで燐光発光性有機ＥＬ素子に用いられてきた正孔輸送材料及び正孔輸送能を有したホスト材料としては、特許文献６に示されるカルバゾール誘導体（例えば、下記のＨＴＭ－１）が知られていた。カルバゾール誘導体は三重項エネルギーレベル(以後、Ｔ１と略称する)が高く三重項励起子を閉じ込める能力に優れているが、正孔移動度が低く、且つ電気的な還元耐久性に課題がある。そのため、電子輸送能が向上した発光層と組み合わせた場合、発光層への正孔の供給が律速になって発光層内で電子過多に偏り、これらを用いた有機ＥＬ素子では発光効率の低下及び短寿命化の懸念がある。 As a hole transporting material and a host material having a hole transporting ability, which have been used for phosphorescent organic EL devices up to now, carbazole derivatives (for example, HTM-1 described below) shown in Patent Document 6 are known. It was Although carbazole derivatives have high triplet energy levels (hereinafter abbreviated as T1) and are excellent in ability to confine triplet excitons, they have low hole mobility and have problems in electrical reduction durability. Therefore, when combined with a light emitting layer having an improved electron transporting ability, the supply of holes to the light emitting layer is rate-limited and is biased to an excessive amount of electrons in the light emitting layer. There is a concern for shortening the life.
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
　以上のような問題を解決する試みとして、特許文献７では電気的耐久性に優れ、且つ高い正孔輸送能を持つ下記の式で表されるモノアミン化合物（例えば、下記のＨＴＭ－２）が提案されている。 As an attempt to solve the problems as described above, Patent Document 7 proposes a monoamine compound (for example, HTM-2 below) represented by the following formula having excellent electric durability and high hole transportability. It is done.
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
　しかしながら、これらのモノアミン化合物は、カルバゾール誘導体に比べて、高い正孔移動度を有しているが、Ｔ１が低い課題がある。そのため三重項励起子の閉じ込めが不充分となり、励起子失活による発光効率の低下、及び素子の短寿命化の懸念がある。そのため、正孔移動度が高く、且つ三重項励起子の閉じ込めに優れた正孔輸送材料及びホスト材料が求められていた。 However, these monoamine compounds have higher hole mobility than carbazole derivatives but have a problem of low T1. Therefore, the confinement of triplet excitons becomes insufficient, and there is a concern that the luminous efficiency is lowered due to the exciton deactivation and the lifetime of the device is shortened. Therefore, a hole transport material and a host material having high hole mobility and excellent in confinement of triplet excitons have been required.
日本国特開平８－０４８６５６号公報Japanese Patent Application Laid-Open No. 8-048656 日本国特開平７－１２６６１５号公報Japanese Patent Application Laid-Open No. 7-126615 日本国特開２００６－１５１９７９号公報Japanese Patent Application Laid-Open No. 2006-151979 国際公開第２０１５／０３４１２５号International Publication No. 2015/034125 国際公開第２０１６／０１３７３２号International Publication No. 2016/013732 日本国特開平８－００３５４７号公報Japanese Patent Application Laid-Open No. 8-003547 日本国特開２００６－３５２０８８号公報Japanese Patent Application Laid-Open No. 2006-352088 国際公開第２０１７／０９９１５５号公報International Publication No. 2017/099155 日本国特開２００２－１０５０５５号公報Japanese Patent Application Laid-Open No. 2002-105055 国際公開第２０１４／００７５６５号International Publication No. 2014/007565 国際公開第２０１４／１８８９４７号International Publication No. 2014/188947 国際公開第２０１５／１９０４００号International Publication No. 2015/190400 日本国特開２０１０－８３８６２公報Japan JP 2010-83862 国際公開第２０１５／０３８５０３号International Publication No. 2015/038503 日本国特開２００５－１０８８０４号公報Japanese Patent Application Laid-Open No. 2005-108804 国際公開第２００８／６２６３６号公報International Publication No. 2008/62636 国際公開第２０１４／００９３１０号International Publication No. 2014/009310
　本発明の目的は、高効率、高耐久性の有機ＥＬ素子用の材料として、正孔の注入・輸送性能に優れ、電子阻止能力を有し、薄膜状態での安定性が高く、発光効率が高い優れた特性を有する有機化合物を提供し、さらにこの化合物を用いて、高効率、高耐久性の有機ＥＬ素子を提供することにある。 The object of the present invention is as a material for organic EL devices having high efficiency and high durability, excellent in hole injection / transport performance, electron blocking ability, high stability in thin film state, luminous efficiency An object of the present invention is to provide an organic compound having high excellent properties, and further to provide a highly efficient and highly durable organic EL device using this compound.
　本発明が提供しようとする有機化合物が具備すべき物理的な特性としては、（１）正孔の注入特性が良いこと、（２）正孔の移動度が大きいこと、（３）電子阻止能力に優れること、（４）薄膜状態が安定であること、（５）電子に対する耐久性に優れていること、をあげることができる。また、本発明が提供しようとする有機ＥＬ素子が具備すべき物理的な特性としては、（１）発光効率が高いこと、（２）素子寿命が長いこと、をあげることができる。 Physical properties to be provided by the organic compound to be provided by the present invention include (1) good hole injection characteristics, (2) high hole mobility, and (3) electron blocking ability. (4) stability of the thin film state, and (5) excellent durability to electrons. Further, as physical properties to be provided by the organic EL element to be provided by the present invention, (1) high luminous efficiency and (2) long element life can be mentioned.
　そこで本発明者らは上記の目的を達成するために、芳香族三級アミン構造が高い正孔注入・輸送能力を有していることと、電気的耐久性と薄膜安定性への効果に期待して、新規なトリアリールアミン構造を有するモノアミン化合物を設計して化学合成し、該化合物を用いて種々の有機ＥＬ素子を試作し、素子の特性評価を鋭意行った結果、本発明を完成するに至った。 Therefore, in order to achieve the above object, the present inventors are expecting that the aromatic tertiary amine structure has high hole injecting / transporting ability, and the effect on the electric durability and the thin film stability. And design and chemically synthesize monoamine compounds having a novel triarylamine structure, and trial manufacture of various organic EL devices using the compounds to complete the present invention as a result of intensive characterization of the devices. It came to
　上記課題を解決することのできる、本発明の有機ＥＬ素子は、
１）陽極と陰極との間に、陽極側から少なくとも第一正孔輸送層と第二正孔輸送層と緑色発光層と電子輸送層とをこの順に備え、前記第一正孔輸送層と前記電子輸送層との間に配置された層のうちの少なくとも一層は、下記一般式（１）で表される、アリールアミン化合物を含有する。 The organic EL device of the present invention, which can solve the above problems,
1) Between the anode and the cathode, at least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above At least one of the layers disposed between the electron transporting layer and the electron transporting layer contains an arylamine compound represented by the following general formula (1).
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
（式中、Ａｒ１、Ａｒ2、Ａｒ３、Ａｒ４はそれぞれ同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。） (Wherein, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent Good C 2 -C 6 linear or branched alkenyl group, C 1 -C 6 linear or branched alkyloxy group which may have substituent (s), substituent (s) May have 5 carbon atoms 10 cycloalkyloxy groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted fused polycyclic aromatic groups or substituted or unsubstituted aryloxy groups Represents
　上記課題を解決することのできる、本発明の別の有機ＥＬ素子は、
２）陽極と陰極との間に、陽極側から少なくとも第一正孔輸送層と第二正孔輸送層と緑色発光層と電子輸送層とをこの順に備え、前記第一正孔輸送層と前記電子輸送層との間に配置された層のうちの少なくとも一層は、下記一般式（２）で表される、アリールアミン化合物を含有する。 Another organic EL device of the present invention, which can solve the above problems, is
2) Between the anode and the cathode, at least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above At least one of the layers disposed between the electron transporting layer and the electron transporting layer contains an arylamine compound represented by the following general formula (2).
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
（式中、Ａｒ１、Ａｒ2は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ５、Ａｒ６は相互に同一でも異なってもよく、フェニル基、ビフェニリル基、ナフチル基、フェナントレニル基、またはフルオレニル基を表し、Ｒ４は水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。） (Wherein, Ar 1 and Ar 2 may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted fused polycyclic aromatic compounds Ar 5 and Ar 6 may be identical to or different from each other, and may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group, R 4 is a hydrogen atom, a deuterium atom or a fluorine atom A chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a carbon number of 5 to a carbon atom which may have a substituent, 10 cycloalkyl groups, C2-C6 linear or branched alkenyl groups which may have substituents, C1-C6 linear groups which may have substituents The state is also And a branched alkyloxy group, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic ring A group, a substituted or unsubstituted fused polycyclic aromatic group or a substituted or unsubstituted aryloxy group)
　また、上記課題を解決することのできる、本発明のアリールアミン化合物は、下記一般式（１）で表される。 Moreover, the arylamine compound of this invention which can solve the said subject is represented by following General formula (1).
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
（式中、Ａｒ１、Ａｒ2、Ａｒ３、Ａｒ４はそれぞれ同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。） (Wherein, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent Good C 2 -C 6 linear or branched alkenyl group, C 1 -C 6 linear or branched alkyloxy group which may have substituent (s), substituent (s) May have 5 carbon atoms 10 cycloalkyloxy groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted fused polycyclic aromatic groups or substituted or unsubstituted aryloxy groups Represents
　本発明のアリールアミン化合物は、有機ＥＬ素子の発光層または発光層に隣接した第二正孔輸送層として有用であり、電子阻止能力に優れ、優れた電子に対する耐久性を有し、かつアモルファス性が良好であり、薄膜状態が安定で、耐熱性に優れている。本発明の有機ＥＬ素子は発光効率および電力効率が高く、かつ優れた電子に対する耐久性により素子を長寿命化することができる。 The arylamine compound of the present invention is useful as a light emitting layer of the organic EL device or as a second hole transporting layer adjacent to the light emitting layer, has excellent electron blocking ability, has excellent electron durability, and is amorphous. Is excellent, the thin film state is stable, and the heat resistance is excellent. The organic EL device of the present invention is high in luminous efficiency and power efficiency, and can extend the life of the device due to excellent electron durability.
実施例１０～２１および比較例１～６のＥＬ素子構成を示した図である。FIG. 6 is a view showing EL element configurations of Examples 10 to 21 and Comparative Examples 1 to 6.
　以下、本発明の実施形態について詳細に説明する。まず、本実施形態のアリールアミン化合物および有機ＥＬ素子について、その態様を列挙して説明する。なお、本願において「ないし」との用語は範囲を表す用語である。例えば「５ないし１０」との記載は、「５以上１０以下」を意味し、「ないし」の前後に記載される数値自体も含む範囲を表す。 Hereinafter, embodiments of the present invention will be described in detail. First, aspects of the arylamine compound and the organic EL device of the present embodiment are listed and described. In the present application, the term "to" is a term representing a range. For example, the description “5 to 10” means “5 or more and 10 or less”, and indicates a range including the numerical values themselves described before and after “to”.
１）陽極と陰極との間に、陽極側から少なくとも第一正孔輸送層と第二正孔輸送層と緑色発光層と電子輸送層とをこの順に備え、前記第一正孔輸送層と前記電子輸送層との間に配置された層のうちの少なくとも一層は、下記一般式（１）で表される、アリールアミン化合物を含有する、有機ＥＬ素子。 1) Between the anode and the cathode, at least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above An organic EL device, wherein at least one of the layers disposed between the electron transport layer and the layer contains an arylamine compound represented by the following general formula (1).
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000023
（式中、Ａｒ１、Ａｒ2、Ａｒ３、Ａｒ４はそれぞれ同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。） (Wherein, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent Good C 2 -C 6 linear or branched alkenyl group, C 1 -C 6 linear or branched alkyloxy group which may have substituent (s), substituent (s) May have 5 carbon atoms 10 cycloalkyloxy groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted fused polycyclic aromatic groups or substituted or unsubstituted aryloxy groups Represents
２）陽極と陰極との間に、陽極側から少なくとも第一正孔輸送層と第二正孔輸送層と緑色発光層と電子輸送層とをこの順に備え、前記第一正孔輸送層と前記電子輸送層との間に配置された層のうちの少なくとも一層は、下記一般式（２）で表される、アリールアミン化合物を含有する、有機ＥＬ素子。 2) Between the anode and the cathode, at least the first hole transport layer, the second hole transport layer, the green light emitting layer and the electron transport layer are provided in this order from the anode side, and the first hole transport layer and the above An organic EL device, comprising an arylamine compound represented by the following general formula (2), at least one of the layers disposed between the electron transport layer and the electron transport layer.
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000024
（式中、Ａｒ１、Ａｒ2は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ５、Ａｒ６は相互に同一でも異なってもよく、フェニル基、ビフェニリル基、ナフチル基、フェナントレニル基、またはフルオレニル基を表し、Ｒ４は水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。） (Wherein, Ar 1 and Ar 2 may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted fused polycyclic aromatic compounds Ar 5 and Ar 6 may be identical to or different from each other, and may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group, R 4 is a hydrogen atom, a deuterium atom or a fluorine atom A chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a carbon number of 5 to a carbon atom which may have a substituent, 10 cycloalkyl groups, C2-C6 linear or branched alkenyl groups which may have substituents, C1-C6 linear groups which may have substituents The state is also And a branched alkyloxy group, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic ring A group, a substituted or unsubstituted fused polycyclic aromatic group or a substituted or unsubstituted aryloxy group)
３）前記緑色発光層は、ホストと燐光発光性ドーパントとを含み、前記ホストは、下記の化学式Ｈｏｓｔ－Ａで表される少なくとも１種の第１ホスト化合物と、下記の化学式Ｈｏｓｔ－Ｂで表される少なくとも１種の第２ホスト化合物と、を含む、前記１）または２）に記載の有機ＥＬ素子。 3) The green light emitting layer includes a host and a phosphorescent dopant, and the host is a table represented by the following chemical formula Host-B with at least one first host compound represented by the following chemical formula Host-A. The organic EL device according to 1) or 2), further comprising at least one second host compound.
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
（前記Ｈｏｓｔ－Ａ中、Ｚは、それぞれ独立して、ＮまたはＣＲａであり、Ｚのうちの少なくとも一つは、Ｎであり、Ｒ５～Ｒ１４およびＲａは、それぞれ独立して、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換もしくは無置換の炭素数１ないし１５のアルキル基、置換もしくは無置換の環形成炭素数６ないし１２のアリール基であり、前記Ｈｏｓｔ－Ａでトリフェニレン基に置換された６員環の総個数は、６個以下であり、Ｌ１は、置換もしくは無置換のフェニレン基、置換もしくは無置換のビフェニレン基または置換もしくは無置換のターフェニレン基であり、ｎ１～ｎ３は、それぞれ独立して、０または１であり、ｎ１＋ｎ２＋ｎ３≧１である。） (In the above Host-A, Z is each independently N or CRa, at least one of Z is N, and R 5 to R 14 and Ra are each independently a hydrogen atom Deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, The total number of 6-membered rings substituted with a triphenylene group in Host-A is 6 or less, and L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted ter And n1 to n3 each independently represent 0 or 1, and n1 + n2 + n3 ≧ 1).
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000026
（前記Ｈｏｓｔ－Ｂ中、Ｙは単結合、置換若しくは無置換の環形成炭素数６ないし３０のアリーレン基、又は置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリーレン基であり、Ａｒ７は、置換若しくは無置換の環形成炭素数６ないし３０のアリール基、置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリール基であり、Ｒ１５～Ｒ１８は、それぞれ独立して、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、炭素数１ないし１５のアルキル基、置換若しくは無置換の環形成炭素数６ないし５０のアリール基、または置換若しくは無置換の環形成炭素数４ないし５０のヘテロアリール基であり、Ｒ１５～Ｒ１８およびＡｒ７のうちの少なくとも一つは、置換もしくは無置換のトリフェニレン基または置換もしくは無置換のカルバゾリル基を含む。） (In the above Host-B, Y is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, Ar 7 Is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and R 15 to R 18 each independently represent hydrogen Atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring forming C 4 -C to a heteroaryl group 50, at least one of R 15 ~ R 18 and Ar 7 represents a substituted or unsubstituted triphenylene Or a substituted or unsubstituted carbazolyl group.)
４）前記緑色発光層は、ホストと燐光発光性ドーパントとを含み、前記燐光発光性ドーパントは、イリジウムを含む金属錯体である、前記１）～３）のいずれかに記載の有機ＥＬ素子。 4) The organic EL device according to any one of 1) to 3), wherein the green light emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex containing iridium.
５）前記緑色発光層は、ホストと燐光発光性ドーパントとを含み、前記燐光発光性ドーパントは、下記一般式（３）で表される金属錯体である、前記１）～３）のいずれかに記載の有機ＥＬ素子。 5) The green light emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is any of the metal complexes represented by the following general formula (3): Organic EL element as described.
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
（式中、Ｒ１９～Ｒ３４はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、トリメチルシリル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基および縮合多環芳香族基からなる群から選ばれる基によって置換されたジ置換アミノ基を表す。ｎは１～３の整数を表す。） (Wherein, R 19 to R 34 may be the same as or different from each other, and are each independently a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, or a C1-C6 linear group optionally having substituents) Or a branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched chain having 2 to 6 carbon atoms An alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent Trimethylsilyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted fused polycyclic aromatic group, substituted or unsubstituted aryloxy group, or .n representing the family hydrocarbon group, disubstituted amino group substituted by a group selected from the group consisting of aromatic heterocyclic groups and fused polycyclic aromatic group is an integer of 1-3.)
６）前記電子輸送層は、下記一般式（４）で表される、ピリミジン構造を有する化合物を含有する、前記１）～５）のいずれかに記載の有機ＥＬ素子。 6) The organic EL device according to any one of 1) to 5), wherein the electron transporting layer contains a compound having a pyrimidine structure, which is represented by the following general formula (4).
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028
（式中、Ａｒ８は、置換もしくは無置換の芳香族炭化水素基、または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ９、Ａｒ１０は相互に同一でも異なっていてもよく、水素原子、置換もしくは無置換の芳香族炭化水素基、または置換もしくは無置換の縮合多環芳香族基を表し、Ｂは、下記構造式（５）で示される１価基を表す。ここで、Ａｒ９とＡｒ１０は同時に水素原子となることはない。） (Wherein, Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted fused polycyclic aromatic group, and Ar 9 and Ar 10 may be the same as or different from each other, B represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted fused polycyclic aromatic group, and B represents a monovalent group represented by the following structural formula (5): Ar 9 and Ar 10 can not simultaneously be hydrogen atoms.)
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029
（式中、Ａｒ１１は、置換もしくは無置換の芳香族複素環基を表し、Ｒ３５～Ｒ３８は、それぞれ同一でも異なっていてもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、または置換もしくは無置換の縮合多環芳香族基を表す。） (Wherein, Ar 11 represents a substituted or unsubstituted aromatic heterocyclic group, and R 35 to R 38 may be the same or different and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, A cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group; Represents an unsubstituted fused polycyclic aromatic group).
７）前記電子輸送層は、下記一般式（６）で表される、ベンゾアゾール構造を有する化合物を含有する、前記１）～５）のいずれかに記載の有機ＥＬ素子。 7) The organic EL device according to any one of 1) to 5), wherein the electron transporting layer contains a compound having a benzoazole structure, which is represented by the following general formula (6).
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
（式中、Ａｒ１２、Ａｒ１３は相互に同一でも異なっていてもよく、水素原子、重水素原子、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の縮合多環芳香族基、または置換もしくは無置換の芳香族複素環基を表し、Ｖ１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換の芳香族複素環基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、または置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基を表し、Ｘは酸素原子または硫黄原子を表し、Ｗ１、Ｗ２は相互に同一でも異なっていてもよく、炭素原子または窒素原子を表す。） (Wherein, Ar 12 and Ar 13 may be the same as or different from each other, and are a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, Or a substituted or unsubstituted aromatic heterocyclic group, wherein V 1 is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aromatic heterocyclic group A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent And X 2 represents a linear or branched alkenyl group having 2 to 6 carbon atoms which may have X, an oxygen atom or a sulfur atom, and W 1 and W 2 may be the same or different from each other Well, carbon atom or nitrogen Represents a prime atom.)
８）前記第一正孔輸送層は、下記一般式（７）または一般式（８）で表されるトリフェニルアミン誘導体を含有する、前記１）～７）のいずれかに記載の有機ＥＬ素子。 8) The organic EL device according to any one of 1) to 7), wherein the first hole transport layer contains a triphenylamine derivative represented by the following general formula (7) or (8) .
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
（式中、Ｒ３９～Ｒ４４は、それぞれ独立して、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５～１０のシクロアルキル基、置換基を有していてもよい炭素原子数２～６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５～１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または置換もしくは無置換のアリールオキシ基を表す。ｒ１～ｒ６はそれぞれ同一でも異なっていてもよく、ｒ１～ｒ４は０～５の整数を表し、ｒ５、ｒ６は０～４の整数を表す。ｒ１～ｒ６が２以上の整数である場合、同一のベンゼン環に複数個結合するＲ３９～Ｒ４４はそれぞれ同一でも異なっていてもよい。また、ベンゼン環とベンゼン環に置換された置換基とが、同一のベンゼン環に複数置換された置換基同士が、および窒素原子を介して互いに隣接するベンゼン環同士が、それぞれ単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子により結合して環を形成してもよい。Ｋ１は下記構造式（ＨＴＭ－Ａ）～（ＨＴＭ－Ｆ）で示される２価基、または単結合を表す。） (Wherein, R 39 to R 44 each independently represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear C 1-6 linear chain that may have a substituent) Or branched alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, and optionally substituted linear or branched 2 to 6 carbon atoms Alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, cycloalkylo having 5 to 10 carbon atoms which may have a substituent R 1 represents a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. each be the same or different is ~ r 6 At best, if r 1 ~ r 4 represents an integer of 0 to 5, r 5, r 6 is .r 1 ~ r 6 represents an integer of 0 to 4 represent an integer of 2 or more, the same benzene ring Each of R 39 to R 44 bonded to plural groups may be the same or different from each other, and the benzene ring and the substituent substituted to the benzene ring may be substituted each other by plural substituents on the same benzene ring. and via the nitrogen atom is a benzene ring which are adjacent to each other, each a single bond, a substituted or unsubstituted methylene group, optionally .K 1 be bonded to an oxygen atom or a sulfur atom to form a ring is represented by the following general formula ( HTM-A) to (HTM-F) represents a divalent group or a single bond.)
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
（式中、ｊは１～３の整数を表す。） (Wherein, j represents an integer of 1 to 3)
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
（式中、Ｒ４５～Ｒ５６は、それぞれ独立して、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５～１０のシクロアルキル基、置換基を有していてもよい炭素原子数２～６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５～１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または置換もしくは無置換のアリールオキシ基を表す。ｒ７～ｒ１８はそれぞれ同一でも異なっていてもよく、ｒ７～ｒ１２は０～５の整数を表し、ｒ１３～ｒ１８は０～４の整数を表す。ｒ７～ｒ１８が２以上の整数である場合、同一のベンゼン環に複数個結合するＲ４５～Ｒ５６はそれぞれ同一でも異なっていてもよい。また、ベンゼン環とベンゼン環に置換された置換基とが、同一のベンゼン環に複数置換された置換基同士が、および窒素原子を介して互いに隣接するベンゼン環同士が、それぞれ単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子により結合して環を形成してもよい。Ｋ２～Ｋ４はそれぞれ同一でも異なってもよく、一般式（７）に記載の（ＨＴＭ－Ａ）～（ＨＴＭ－Ｆ）で示される２価基、または単結合を表す。） (Wherein, R 45 to R 56 each independently represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear chain having 1 to 6 carbon atoms which may have a substituent) Or branched alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, and optionally substituted linear or branched 2 to 6 carbon atoms Alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, cycloalkylo having 5 to 10 carbon atoms which may have a substituent R 7 represents a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. or different from each ~ r 18 the same May have, if r 7 ~ r 12 represents an integer of 0 ~ 5, r 13 ~ r 18 is .r 7 ~ r 18 represents an integer of 0 to 4 represent an integer of 2 or more, the same benzene ring And R 45 to R 56 bonded to each other may be the same as or different from each other, and the benzene ring and the substituents substituted on the benzene ring may be substituents each substituted on the same benzene ring, and via the nitrogen atom is a benzene ring which are adjacent to each other, each a single bond, a substituted or unsubstituted methylene group, an oxygen atom or .K 2 ~ K 4 be bonded to the sulfur atom to form a ring respectively It may be the same or different, and represents a divalent group represented by (HTM-A) to (HTM-F) described in General Formula (7), or a single bond.)
９）下記一般式（１）で表される、アリールアミン化合物。 9) An arylamine compound represented by the following general formula (1).
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
（式中、Ａｒ１、Ａｒ2、Ａｒ３、Ａｒ４はそれぞれ同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。） (Wherein, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent Good C 2 -C 6 linear or branched alkenyl group, C 1 -C 6 linear or branched alkyloxy group which may have substituent (s), substituent (s) May have 5 carbon atoms 10 cycloalkyloxy groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted fused polycyclic aromatic groups or substituted or unsubstituted aryloxy groups Represents
　一般式（１）中のＡｒ１～Ａｒ４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピリミジニル基、トリアジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、およびカルボリニル基などをあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 1 to Ar 4 in the general formula (1), or “substituted or unsubstituted fused multiple group” Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the ring aromatic group include phenyl group, biphenylyl group, terphenylyl group, naphthyl group and anthracenyl group Group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group Group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group Quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, and the like acridinyl group, and carbolinyl group.
　一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；ビニル基、アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基のような基をあげることができ、これらの置換基は、さらに前記例示した置換基が置換していても良い。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 As the “substituent” in the “substituted aromatic hydrocarbon group”, the “substituted aromatic heterocyclic group” or the “substituted fused polycyclic aromatic group” represented by Ar 1 to Ar 4 in the general formula (1) Specifically, deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom, etc .; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl Linear or branched alkyloxy group having 1 to 6 carbon atoms such as oxy group; alkenyl group such as vinyl group and allyl group; phenyloxy group, tolyloxy group and the like Aryloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoran Aromatic hydrocarbon group or fused polycyclic aromatic group such as tenyl group, triphenylenyl group; pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group , Indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, aromatic heterocyclic ring such as carborinyl group Aryl vinyl groups such as styryl group and naphthyl vinyl group; and groups such as acyl group such as acetyl group and benzoyl group, and these substituents may be further substituted by the above-mentioned substituents. good. In addition, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ３で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、２－ブテニル基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted” represented by R 1 to R 3 in the general formula (1), “having a substituent” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)” As the linear or branched alkyl group of 6, the "C5-C10 cycloalkyl group" or the "C2-C6 linear or branched alkenyl group" are specifically mentioned , Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclo And xyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group, 2-butenyl group and the like, and these groups may be a single bond, a substituted or unsubstituted methylene group, They may be bonded to each other via an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；ビニル基、アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していても良い。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “C1-C6 linear or branched alkyl group having a substituent, which is represented by R 1 to R 3 in the general formula (1),“ c-5 having a substituent ” Specific examples of the "substituent" in the cycloalkyl group of "" or "C2-C6 linear or branched alkenyl group having a substituent" include deuterium atom, cyano group, nitro group; A halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group An alkenyl group such as a phenyl group, an aryloxy group such as a tolyloxy group, an arylalkyloxy group such as a benzyloxy group or a phenethyloxy group; Aromatic hydrocarbon group or fused polycyclic aromatic group such as group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and the like Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group; Examples thereof include groups such as aromatic heterocyclic groups such as benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carborinyl group and the like, and these substituents may be further substituted by the substituents exemplified above. May be In addition, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（１）中のＲ１～Ｒ３で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、ｎ－プロピルオキシ基、イソプロピルオキシ基、ｎ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、１－アダマンチルオキシ基、２－アダマンチルオキシ基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent,” represented by R 1 to R 3 in the general formula (1), or “having a substituent” "C1-C6 linear or branched alkyloxy group" or "C5-C10 cycloalkyloxy group" in the optionally substituted C5-C10 cycloalkyloxy group " As “specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group , Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Etc. can be mentioned, these groups to each other is a single bond, a substituted or unsubstituted methylene group, via an oxygen atom or a sulfur atom may bond to each other to form a ring.
　一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」としては、上記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyloxy group having a substituent, which is represented by R 1 to R 3 in the general formula (1), or“ c5-C having a substituent ” As the “substituent” in the cycloalkyloxy group of 10, a “C1-C6 linear or branched C1-C6 carbon atom having a substituent” represented by R 1 to R 3 in the above general formula (1) can be mentioned The “substituent” in the alkyl group of “C 5 to C 10 cycloalkyl group having a substituent” or “C 2 to C 6 linear or branched alkenyl group having a substituent” The thing similar to what was shown can be mentioned, and the aspect which can take can mention the same thing.
　一般式（１）中のＲ１～Ｒ３で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、上記一般式（１）中のＡｒ１～Ａｒ４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」に関して示したものと同様のものをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。また、これらの基は置換基を有していてよく、置換基として、上記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 3 in the general formula (1), or “substituted or unsubstituted condensed poly The “aromatic hydrocarbon group”, the “aromatic heterocyclic group” or the “fused polycyclic aromatic group” in the ring aromatic group is represented by Ar 1 to Ar 4 in the above general formula (1) "Aromatic hydrocarbon group" in "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted fused polycyclic aromatic group", "aromatic" Group may be the same as those described with regard to “heterocyclic group” or “fused polycyclic aromatic group”, and these groups may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom You may combine with each other to form a ring. Moreover, these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex The same groups as those described for "substituent" in the "ring group" or "substituted fused polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible embodiments.
　一般式（１）中のＲ１～Ｒ３で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、具体的に、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、ナフチルオキシ基、アントラセニルオキシ基、フェナントレニルオキシ基、フルオレニルオキシ基、インデニルオキシ基、ピレニルオキシ基、ペリレニルオキシ基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。また、これらの基は置換基を有していてよく、置換基として、上記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 Specific examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R 1 to R 3 in the general formula (1) include a phenyloxy group, a biphenylyloxy group and a terphenyl group. Ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc. can be mentioned, and these groups are single They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Moreover, these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex The same groups as those described for "substituent" in the "ring group" or "substituted fused polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible embodiments.
　一般式（１）中のＡｒ１、Ａｒ２としては、「置換もしくは無置換の芳香族炭化水素基」、または「置換もしくは無置換の縮合多環芳香族基」が好ましく、フェニル基、ナフチル基、フェナントレニル基、フルオレニル基がより好ましく、置換基を有するフェニル基、置換基を有するフルオレニル基が特に好ましい。ここで、フェニル基の置換基としては、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、フェナントレニル基、フルオレニル基が好ましく、フルオレニル基の置換基としては、メチル基、フェニル基が好ましい。一般式（１）中のＡｒ３、Ａｒ４としては、「置換もしくは無置換の芳香族炭化水素基」または「置換もしくは無置換の縮合多環芳香族基」が好ましく、フェニル基、ビフェニリル基、ナフチル基、フェナントレニル基、フルオレニル基がより好ましく、無置換のフェニル基、無置換のビフェニリル基、無置換のナフチル基、置換基を有するフルオレニル基がより好ましい。ここで、フルオレニル基の置換基としては、メチル基、フェニル基が好ましい。 As Ar 1 and Ar 2 in the general formula (1), “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted fused polycyclic aromatic group” is preferable, and a phenyl group and a naphthyl group are preferable. A phenanthrenyl group and a fluorenyl group are more preferable, and a substituted phenyl group and a substituted fluorenyl group are particularly preferable. Here, as a substituent of a phenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group, and a fluorenyl group are preferable, and as a substituent of a fluorenyl group, a methyl group and a phenyl group are preferable. As Ar 3 and Ar 4 in the general formula (1), “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted fused polycyclic aromatic group” is preferable, and a phenyl group, a biphenylyl group, A naphthyl group, a phenanthrenyl group, and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, and a fluorenyl group having a substituent are more preferable. Here, as a substituent of a fluorenyl group, a methyl group and a phenyl group are preferable.
　一般式（１）中のＲ１、Ｒ３としては、水素原子、重水素原子が好ましく、合成上の観点から、水素原子がより好ましい。
　一般式（１）中のＲ２としては、「置換もしくは無置換の芳香族炭化水素基」または「置換もしくは無置換の縮合多環芳香族基」が好ましく、フェニル基、ビフェニリル基、ナフチル基、フェナントレニル基、フルオレニル基がより好ましく、無置換のフェニル基、無置換のビフェニリル基、無置換のナフチル基、置換基を有するフルオレニル基がより好ましい。ここで、フルオレニル基の置換基としては、メチル基、フェニル基が好ましい。 As R 1 and R 3 in the general formula (1), a hydrogen atom and a deuterium atom are preferable, and from the viewpoint of synthesis, a hydrogen atom is more preferable.
As R 2 in the general formula (1), “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted fused polycyclic aromatic group” is preferable, and a phenyl group, a biphenylyl group, a naphthyl group, The phenanthrenyl group and the fluorenyl group are more preferable, and the unsubstituted phenyl group, the unsubstituted biphenylyl group, the unsubstituted naphthyl group, and the fluorenyl group having a substituent are more preferable. Here, as a substituent of a fluorenyl group, a methyl group and a phenyl group are preferable.
　一般式（２）中のＲ４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、２－ブテニル基などをあげることができる。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted” represented by R 4 in the general formula (2), “even if it has a substituent” “C 1 to C 6 straight” in “C 5 to C 10 cycloalkyl group” or “C 2 to C 6 linear or branched alkenyl group which may have a substituent (s)” As the chain or branched alkyl group, the “C 5 to C 10 cycloalkyl group” or the “C 2 to C 6 linear or branched alkenyl group”, a methyl group is specifically exemplified. , Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl Groups, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group, 2-butenyl group and the like.
　一般式（２）中のＲ４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；ビニル基、アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができる。 “C1-C6 linear or branched alkyl group having a substituent, which is represented by R 4 in the general formula (2)”, “cycloalkyl having a substituent having 5 to 10 carbon atoms” Examples of the “substituent” in the group ”or“ a C 2 to C 6 linear or branched alkenyl group having a substituent ”specifically include a deuterium atom, a cyano group, a nitro group; Halogen atoms such as chlorine atom, bromine atom and iodine atom; C1-C6 linear or branched alkyloxy groups such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group and the like Alkenyl groups; aryloxy groups such as phenyloxy group and tolyloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group; An aromatic hydrocarbon group or a fused polycyclic aromatic group such as phenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; Group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group And groups such as aromatic heterocyclic groups such as pyrazolyl group, dibenzofuranyl group, dibenzothienyl group and carborinyl group.
　一般式（２）中のＲ４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、ｎ－プロピルオキシ基、イソプロピルオキシ基、ｎ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、１－アダマンチルオキシ基、２－アダマンチルオキシ基などをあげることできる。 “Having a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent,” represented by R 4 in the general formula (2) or “having a substituent As the "C1-C6 linear or branched alkyloxy group" or the "C5-C10 cycloalkyloxy group" in the C5-C10 cycloalkyloxy group is also preferable Specifically, methyloxy, ethyloxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, n-pentyloxy, n-hexyloxy, cyclopentyloxy, cyclohexyloxy Group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group, etc. You can
　一般式（２）中のＲ４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」としては、上記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyloxy group having a substituent, which is represented by R 4 in the general formula (2), or“ cyclo having 5 to 10 carbon atoms having a substituent ” As the “substituent” in the alkyloxy group ”, a“ C 1 to C 6 linear or branched alkyl group having a substituent ”represented by R 1 to R 3 in the above general formula (1) “Substituents” in “C 5 -C 10 cycloalkyl group having substituent (s)” or “C 2 -C 6 linear or branched alkenyl group having substituent (s)” The same thing can be mentioned as the same thing as the thing which can be mentioned.
　一般式（２）中のＲ４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、上記一般式（１）中のＡｒ１～Ａｒ４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」に関して示したものと同様のものをあげることができる。また、これらの基は置換基を有していてよく、置換基として、上記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 4 in the general formula (2), or “substituted or unsubstituted fused polycyclic aromatic group As the “aromatic hydrocarbon group”, the “aromatic heterocyclic group” or the “fused polycyclic aromatic group” in the group, “substituted or substituted Ar 1 to Ar 4 in the above general formula (1)” can be used. "Aromatic hydrocarbon group" in "unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted fused polycyclic aromatic group", "aromatic heterocycle" Mention may be made of the same ones as described for the group "or" fused polycyclic aromatic group ". Moreover, these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex The same groups as those described for "substituent" in the "ring group" or "substituted fused polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible embodiments.
　一般式（２）中のＲ４で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、具体的に、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、ナフチルオキシ基、アントラセニルオキシ基、フェナントレニルオキシ基、フルオレニルオキシ基、インデニルオキシ基、ピレニルオキシ基、ペリレニルオキシ基などをあげることができる。また、これらの基は置換基を有していてよく、置換基として、上記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 Specifically as the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R 4 in General Formula (2), a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group And naphthyloxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, indenyloxy, pyrenyloxy and perylenyloxy groups. Moreover, these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), “substituted aromatic complex The same groups as those described for "substituent" in the "ring group" or "substituted fused polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible embodiments.
　一般式（２）中のＲ４としては、水素原子または「置換もしくは無置換の芳香族炭化水素基」が好ましく、フェニル基、ナフチル基がより好ましく、無置換のフェニル基がより好ましい。 As R 4 in the general formula (2), a hydrogen atom or a “substituted or unsubstituted aromatic hydrocarbon group” is preferable, a phenyl group and a naphthyl group are more preferable, and a non-substituted phenyl group is more preferable.
　一般式（２）中のＡｒ１、Ａｒ２は、上記一般式（１）中のＡｒ１、Ａｒ２と同じである。 Ar 1, Ar 2 in the general formula (2) is the same as Ar 1, Ar 2 in the general formula (1).
　一般式（２）中のＡｒ５、Ａｒ６としては、フェニル基、ビフェニリル基、ナフチル基、フェナントレニル基、またはフルオレニル基がより好ましく、無置換のフェニル基、無置換のビフェニリル基、無置換のナフチル基、置換基を有するフルオレニル基がより好ましい。ここで、フルオレニル基の置換基としては、メチル基、フェニル基が好ましい。 As Ar 5 and Ar 6 in the general formula (2), a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group is more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl A group and a fluorenyl group having a substituent are more preferable. Here, as a substituent of a fluorenyl group, a methyl group and a phenyl group are preferable.
　一般式（ＨＯＳＴ―Ａ）中のＲ５～Ｒ１４およびＲａで表される「置換もしくは無置換の炭素数１ないし１５のアルキル基」としては、具体的に、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、ｓ－ブチル基、イソブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ヒドロキシメチル基、１－ヒドロキシエチル基、２－ヒドロキシエチル基、２－ヒドロキシイソブチル基、１，２－ジヒドロキシエチル基、１，３－ジヒドロキシイソプロピル基、２，３－ジヒドロキシ－ｔ－ブチル基、１，２，３－トリヒドロキシプロピル基、クロロメチル基、１－クロロエチル基、２－クロロエチル基、２－クロロイソブチル基、１，２－ジクロロエチル基、１，３－ジクロロイソプロピル基、２，３－ジクロロ－ｔ－ブチル基、１，２，３－トリクロロプロピル基、ブロモメチル基、１－ブロモエチル基、２－ブロモエチル基、２－ブロモイソブチル基、１，２－ジブロモエチル基、１，３－ジブロモイソプロピル基、２，３－ジブロモ－ｔ－ブチル基、１，２，３－トリブロモプロピル基、ヨードメチル基、１－ヨードエチル基、２－ヨードエチル基、２－ヨードイソブチル基、１，２－ジヨードエチル基、１，３－ジヨードイソプロピル基、２，３－ジヨード－ｔ－ブチル基、１，２，３－トリヨードプロピル基、アミノメチル基、１－アミノエチル基、２－アミノエチル基、２－アミノイソブチル基、１，２－ジアミノエチル基、１，３－ジアミノイソプロピル基、２，３－ジアミノ－ｔ－ブチル基、１，２，３－トリアミノプロピル基、シアノメチル基、１－シアノエチル基、２－シアノエチル基、２－シアノイソブチル基、１，２－ジシアノエチル基、１，３－ジシアノイソプロピル基、２，３－ジシアノ－ｔ－ブチル基、１，２，３－トリシアノプロピル基、ニトロメチル基、１－ニトロエチル基、２－ニトロエチル基、２－ニトロイソブチル基、１，２－ジニトロエチル基、１，３－ジニトロイソプロピル基、２，３－ジニトロ－ｔ－ブチル基、１，２，３－トリニトロプロピル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、４－メチルシクロヘキシル基、１－アダマンチル基、２－アダマンチル基、１－ノルボルニル基、２－ノルボルニル基等が挙げられる。 Specific examples of the “substituted or unsubstituted alkyl group having 1 to 15 carbon atoms” represented by R 5 to R 14 and Ra in the general formula (HOST-A) include a methyl group, an ethyl group and a propyl group. , Isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group Group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group Group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group Pill group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2- Aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3- Liaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl 1,2,3-Tricyanopropyl, Nitromethyl, 1-Nitroethyl, 2-Nitroethyl, 2-Nitroisobutyl, 1,2-Dinitroethyl, 1,3-Dinitroisopropyl, 2,3 -Dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1- And norbornyl group, 2-norbornyl group and the like.
　一般式（ＨＯＳＴ―Ａ）中のＲ５～Ｒ１４およびＲａで表される「置換もしくは無置換の炭素数１ないし１５のアルキル基」における「置換基」としては、前記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 Examples of the “substituent” in the “substituted or unsubstituted C 1 to C 15 alkyl group” represented by R 5 to R 14 and Ra in the general formula (HOST-A) include Or a "C1-C6 linear or branched alkyl group having a substituent," a "C5-C10 cycloalkyl group having a substituent," represented by R 1 to R 3 of Mention may be made of the same ones as described for the “substituent” in the “C2-C6 linear or branched alkenyl group having a substituent”, and the same possible embodiments are also exemplified. You can raise it.
　一般式（ＨＯＳＴ―Ａ）中のＲ５～Ｒ１４およびＲａで表される「置換もしくは無置換の環形成炭素数６ないし１２のアリール基」としては、具体的に、フェニル基、ビフェニリル基、１－ナフチル基、２－ナフチル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロフェニル基、テトラフルオロフェニル基、ペンタフルオロフェニル基、トルイル基、ニトロフェニル基、シアノフェニル基、フルオロビフェニリル基、ニトロビフェニリル基、シアノビフェニル基、シアノナフチル基、ニトロナフチル基、フルオロナフチル基などが挙げられる。上記の中でフェニル基、又はビフェニリル基が特に好ましい。 Specific examples of the “substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms” represented by R 5 to R 14 and Ra in the general formula (HOST-A) include a phenyl group, a biphenylyl group, 1-naphthyl group, 2-naphthyl group, fluorophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group, pentafluorophenyl group, toluyl group, nitrophenyl group, cyanophenyl group, fluorobiphenylyl group, nitro And biphenylyl, cyanobiphenyl, cyanonaphthyl, nitronaphthyl, fluoronaphthyl and the like. Among the above, a phenyl group or a biphenylyl group is particularly preferred.
　一般式（ＨＯＳＴ―Ａ）中のＲ５～Ｒ１４およびＲａで表される「置換もしくは無置換の環形成炭素数６ないし１２のアリール基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 As the “substituent” in the “substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms” represented by R 5 to R 14 and Ra in the general formula (HOST-A), the above general formula (1) The same as the “substituents” in the “substituted aromatic hydrocarbon group”, the “substituted aromatic heterocyclic group” or the “substituted fused polycyclic aromatic group” represented by Ar 1 to Ar 4 in The thing which can be mentioned and the aspect which can be taken can mention the same thing.
　一般式（ＨＯＳＴ―Ａ）中のＬ１で表される「置換もしくは無置換のフェニレン基」、「置換もしくは無置換のビフェニレン基」または「置換もしくは無置換のターフェニレン基」における「置換基」としては、前記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituent” in “substituted or unsubstituted phenylene group”, “substituted or unsubstituted biphenylene group” or “substituted or unsubstituted terphenylene group” represented by L 1 in general formula (HOST-A) Is a “C1-C6 linear or branched alkyl group having a substituent,” a carbon atom having a substituent, represented by R 1 to R 3 in the general formula (1); The same ones as described for the “substituent” in the “C 5 to C 10 cycloalkyl group” or “C 2 to C 6 linear or branched alkenyl group having a substituent” can be mentioned. The same can be mentioned as possible modes.
　一般式（ＨＯＳＴ―Ｂ）中のＲ１５～Ｒ１８で表される「炭素数１ないし１５のアルキル基」としては、具体的に、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、ｓ－ブチル基、イソブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ヒドロキシメチル基、１－ヒドロキシエチル基、２－ヒドロキシエチル基、２－ヒドロキシイソブチル基、１，２－ジヒドロキシエチル基、１，３－ジヒドロキシイソプロピル基、２，３－ジヒドロキシ－ｔ－ブチル基、１，２，３－トリヒドロキシプロピル基、クロロメチル基、１－クロロエチル基、２－クロロエチル基、２－クロロイソブチル基、１，２－ジクロロエチル基、１，３－ジクロロイソプロピル基、２，３－ジクロロ－ｔ－ブチル基、１，２，３－トリクロロプロピル基、ブロモメチル基、１－ブロモエチル基、２－ブロモエチル基、２－ブロモイソブチル基、１，２－ジブロモエチル基、１，３－ジブロモイソプロピル基、２，３－ジブロモ－ｔ－ブチル基、１，２，３－トリブロモプロピル基、ヨードメチル基、１－ヨードエチル基、２－ヨードエチル基、２－ヨードイソブチル基、１，２－ジヨードエチル基、１，３－ジヨードイソプロピル基、２，３－ジヨード－ｔ－ブチル基、１，２，３－トリヨードプロピル基、アミノメチル基、１－アミノエチル基、２－アミノエチル基、２－アミノイソブチル基、１，２－ジアミノエチル基、１，３－ジアミノイソプロピル基、２，３－ジアミノ－ｔ－ブチル基、１，２，３－トリアミノプロピル基、シアノメチル基、１－シアノエチル基、２－シアノエチル基、２－シアノイソブチル基、１，２－ジシアノエチル基、１，３－ジシアノイソプロピル基、２，３－ジシアノ－ｔ－ブチル基、１，２，３－トリシアノプロピル基、ニトロメチル基、１－ニトロエチル基、２－ニトロエチル基、２－ニトロイソブチル基、１，２－ジニトロエチル基、１，３－ジニトロイソプロピル基、２，３－ジニトロ－ｔ－ブチル基、１，２，３－トリニトロプロピル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、４－メチルシクロヘキシル基、１－アダマンチル基、２－アダマンチル基、１－ノルボルニル基、２－ノルボルニル基等が挙げられる。 The general formula (HOST-B) "alkyl group having 1 to 15 carbon atoms" represented by R 15 ~ R 18 being, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl Group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group , 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1 -Chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro- -Butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2 , 3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3 -Diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyano Ethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1,2, 3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t- group Butyl group, 1,2,3-trinitropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2- And norbornyl group and the like.
　一般式（ＨＯＳＴ―Ｂ）中のＲ１５～Ｒ１８で表される「炭素数１ないし１５のアルキル基」における「置換基」としては前記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 Examples of the “substituent” in the “C1-C15 alkyl group” represented by R 15 to R 18 in the general formula (HOST-B) are represented by R 1 to R 3 in the general formula (1). “C1-C6 linear or branched alkyl group having a substituent,” “C5-C10 cycloalkyl group having a substituent,” or “number of carbon atoms having a substituent The same groups as those described with respect to the “substituent” in the “2 to 6 linear or branched alkenyl group” can be mentioned, and the modes which can be taken also can be the same.
　一般式（ＨＯＳＴ―Ｂ）中のＲ１５～Ｒ１８で表される「置換若しくは無置換の環形成炭素数６ないし５０のアリール基」、または「置換若しくは無置換の環形成炭素数４ないし５０のヘテロアリール基」における「環形成炭素数６ないし５０のアリール基」または「環形成炭素数４ないし５０のヘテロアリール基」としては、具体的に、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、インデニル基、ピレニル基、アセトナフテニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピラニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ジベンゾフラニル基、およびジベンゾチエニル基などを挙げることができる。 “Substituted or unsubstituted aryl ring group having 6 to 50 ring carbon atoms” represented by R 15 to R 18 in the general formula (HOST-B), or “substituted ring or unsubstituted ring carbon atoms 4 to 50 Specific examples of the “aryl group having 6 to 50 ring carbon atoms” or the “heteroaryl group having 4 to 50 ring carbon atoms” in the above “heteroaryl group” include a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. Group, anthryl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, acetonaphthenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyranyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, Carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl , It can be exemplified benzoimidazolyl group, a dibenzofuranyl group, and dibenzothienyl group and the like.
　一般式（ＨＯＳＴ―Ｂ）中のＲ１５～Ｒ１８で表される「置換若しくは無置換の環形成炭素数６ないし５０のアリール基」、または「置換若しくは無置換の環形成炭素数４ないし５０のヘテロアリール基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aryl ring group having 6 to 50 ring carbon atoms” represented by R 15 to R 18 in the general formula (HOST-B), or “substituted ring or unsubstituted ring carbon atoms 4 to 50 The “substituted aromatic hydrocarbon group”, the “substituted aromatic heterocyclic group” or the “substituted condensation” represented by Ar 1 to Ar 4 in the general formula (1) as the “substituent” in the heteroaryl group of The same groups as those described for "substituent" in "polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible modes.
　一般式（ＨＯＳＴ―Ｂ）中のＹで表される「置換若しくは無置換の環形成炭素数６ないし３０のアリーレン基」、または「置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリーレン基」における「環形成炭素数６ないし３０のアリーレン基」または「環形成炭素数５ないし３０のヘテロアリーレン基」としては、具体的に、フェニレン基、ビフェニレン基、ターフェニレン基、ナフチレン基、アントリレン基、フェナントリレン基、フルオレニレン基、インデニレン基、ピレニレン基、アセトナフテニレン基、フルオランテニレン基、トリフェニレニレン基、ピリジレン基、ピラニレン基、キノリレン基、イソキノリレン基、ベンゾフラニレン基、ベンゾチエニレン基、インドリレン基、カルバゾリレン基、ベンゾオキサゾリレン基、ベンゾチアゾリレン基、キノキサリレン基、ベンゾイミダゾリレン基、ピラゾリレン基、ジベンゾフラニレン基、およびジベンゾチエニレン基などが挙げられる。 The “substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms” represented by Y in the general formula (HOST-B), or the “substituted or unsubstituted ring having 5 to 30 ring carbon atoms” Specifically, examples of “an arylene group having 6 to 30 ring carbon atoms” or “a heteroarylene group having 5 to 30 ring carbon atoms” in 」” include a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group and an anthrylene group , Phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, acetonaphthenylene group, fluorantenylene group, triphenylenylene group, pyridinene group, pyranylene group, quinolylene group, isoquinolylene group, benzofuranylene group, benzothienylene group, indole group, carbazolylene group Group, benzoxazole Group, benzothiazolyl alkylene group, Kinokisariren group, benzimidazolylene alkylene group, pyrazolylene group, dibenzo furanyl alkylene group, and the like dibenzo thienylene group.
　一般式（ＨＯＳＴ―Ｂ）中のＹで表される「置換若しくは無置換の環形成炭素数６ないし３０のアリーレン基」、または「置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリーレン基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 The “substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms” represented by Y in the general formula (HOST-B), or the “substituted or unsubstituted ring having 5 to 30 ring carbon atoms” As the “substituent” in the above, “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the general formula (1), “substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” The same thing as what was shown regarding "substituent" in "group" can be mentioned, and the aspect which can take can mention the same thing.
　一般式（ＨＯＳＴ―Ｂ）中のＡｒ７で表される「置換若しくは無置換の環形成炭素数６ないし３０のアリール基」、または「置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリール基」における「環形成炭素数６ないし３０のアリール基」または「環形成炭素数５ないし３０のヘテロアリール基」としては、具体的に、フェニル基、ナフチル基、アントラセニル基、フェナントリル基、ビフェニル基、ｐ－ターフェニル基、ｍ－ターフェニル基、クォーターフェニル基、フルオレニル基、トリフェニレン基、ビフェニレン基、ピレニル基、ベンゾフルオランテニル基、クリセニル基、フェニルナフチル基、ナフチルフェニル基、ピリジル基、キノリル基、イソキノリル基、ベンゾフリル基、ベンゾチエニル基、インドリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリル基、ベンゾイミダゾリル基、ジベンゾフリル基、ジベンゾチエニル基、カルバゾリル基等が挙げられる。 “Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms” represented by Ar 7 in the general formula (HOST-B), or “heteroaryl having substituted or unsubstituted ring atoms having 5 to 30 ring carbon atoms” Specific examples of the "aryl group having 6 to 30 ring carbon atoms" or the "heteroaryl group having 5 to 30 ring carbon atoms" in the group include phenyl group, naphthyl group, anthracenyl group, phenanthryl group and biphenyl group P-terphenyl group, m-terphenyl group, quaternary phenyl group, fluorenyl group, triphenylene group, biphenylene group, pyrenyl group, benzofluoranthenyl group, chrysenyl group, phenylnaphthyl group, naphthylphenyl group, pyridyl group, quinolyl Group, isoquinolyl group, benzofuryl group, benzothienyl group, indolyl group, ben Examples include zoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group and the like.
　一般式（ＨＯＳＴ―Ｂ）中のＡｒ７で表される「置換若しくは無置換の環形成炭素数６ないし３０のアリール基」、または「置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリール基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms” represented by Ar 7 in the general formula (HOST-B), or “heteroaryl having substituted or unsubstituted ring atoms having 5 to 30 ring carbon atoms” As the “substituent” in the group ”, the“ substituted aromatic hydrocarbon group ”represented by Ar 1 to Ar 4 in the general formula (1), the“ substituted aromatic heterocyclic group ”or the“ substituted fused polycyclic aromatic ring The same thing as what was shown about "substituent" in "group group" can be mentioned, and the aspect which can take can mention the same thing.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、２－ブテニル基、などをあげることができる。また、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted” represented by R 19 to R 34 in the general formula (3), “having a substituent” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)” As the linear or branched alkyl group of 6, the "C5-C10 cycloalkyl group" or the "C2-C6 linear or branched alkenyl group" are specifically mentioned Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, Rohekishiru group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group include a 2-butenyl group, and the like. In addition, these groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」、または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては前記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted” represented by R 19 to R 34 in the general formula (3), “having a substituent” As a "substituent" in the "optionally substituted C5-C10 cycloalkyl group" or "optionally substituted C2-C6 linear or branched alkenyl group" Is a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent, which is represented by R 1 to R 3 in the general formula (1), or a group having 5 carbon atoms having a substituent And the same ones as described for "substituent" in "C.sub.10 cycloalkyl group" or "C.sub.2-C 6 linear or branched alkenyl group having substituent (s)" may be mentioned. The same is true for the It is possible.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、ｎ－プロピルオキシ基、イソプロピルオキシ基、ｎ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、１－アダマンチルオキシ基、２－アダマンチルオキシ基などをあげることできる。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent,” represented by R 19 to R 34 in the general formula (3), or “having a substituent” "C1-C6 linear or branched alkyloxy group" or "C5-C10 cycloalkyloxy group" in the optionally substituted C5-C10 cycloalkyloxy group " As “specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group , Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Or the like can be raised to the group.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」としては、上記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyloxy group having a substituent or a substituted alkyl oxy group” represented by R 19 to R 34 in the general formula (3) As the “substituent” in the cycloalkyloxy group of 10, a “C1-C6 linear or branched C1-C6 carbon atom having a substituent” represented by R 1 to R 3 in the general formula (1) is preferable. The “substituent” in the alkyl group of “C 5 to C 10 cycloalkyl group having a substituent” or “C 2 to C 6 linear or branched alkenyl group having a substituent” The thing similar to what was shown can be mentioned, and the aspect which can take can mention the same thing.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、具体的に、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、ナフチルオキシ基、アントラセニルオキシ基、フェナントレニルオキシ基、フルオレニルオキシ基、インデニルオキシ基、ピレニルオキシ基、ペリレニルオキシ基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 Specific examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R 19 to R 34 in the general formula (3) include a phenyloxy group, a biphenylyloxy group and a terphenyl group. Ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc. can be mentioned, and these groups are single They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換もしくは無置換のアリールオキシ基」における「置換基」としては前記一般式（１）中のＲ１～Ｒ３で表される「置換もしくは無置換のアリールオキシ基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 The “substituent” in the “substituted or unsubstituted aryloxy group” represented by R 19 to R 34 in the general formula (3) is represented by R 1 to R 3 in the general formula (1) The same groups as those described for the "substituent" in the "substituted or unsubstituted aryloxy group" can be mentioned, and the same can be mentioned as possible modes.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」、または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ナフチル基、アントラセニル基、フェナントリル基、ナフタセニル基、ピレニル基、ビフェニリル基、ｐ－ターフェニル基、ｍ－ターフェニル基、クリセニル基、トリフェニレニル基、ペリレニル基、インデニル基、フラニル基、チオフェニル基、ピロリル基、ピラゾリル基、イミダゾリル基、トリアゾリル基、オキサゾリル基、チアゾリル基、オキサジアゾリル基、チアジアゾリル基、ピリジル基、ピリミジニル基、ピラジニル基、トリアジニル基、ベンゾフラニル基、ベンゾチオフェニル基、ベンズイミダゾリル基、インドリル基、キノリニル基、イソキノリニル基、キナゾリニル基、キノキサリニル基、ナフチリジニル基、ベンズオキサジニル基、ベンズチアジニル基、アクリジニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基またはこれらの組み合わせであり得るが、これに制限されない。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 19 to R 34 in the general formula (3), or “substituted or unsubstituted condensation Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the polycyclic aromatic group include phenyl group, naphthyl group, anthracenyl group, phenanthryl group, Naphthalsenyl group, pyrenyl group, biphenylyl group, p-terphenyl group, m-terphenyl group, chrysenyl group, triphenylenyl group, perylenyl group, indenyl group, furanyl group, thiophenyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group , Oxazolyl group, thiazolyl group, oxadiazolyl group, thiadiazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, Liazinyl group, benzofuranyl group, benzothiophenyl group, benzimidazolyl group, indolyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, benzoxazinyl group, benzthiazinyl group, acridinyl group, phenazinyl group, pheno It may be, but is not limited to, a thiazinyl group, a phenoxazinyl group or a combination thereof.
　一般式（３）中のＲ１９～Ｒ３４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」、または「置換もしくは無置換の縮合多環芳香族基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 19 to R 34 in the general formula (3), or “substituted or unsubstituted condensation The “substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the general formula (1), the “substituted aromatic heterocyclic group” or the “substituted group” as the “substituent” in the polycyclic aromatic group ” The same groups as those described for "substituent" in the "fused polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible modes.
　一般式（３）中のＲ１９～Ｒ３４で表される「芳香族炭化水素基、芳香族複素環基および縮合多環芳香族基からなる群から選ばれる基によって置換されたジ置換アミノ基」における、「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ナフチル基、アントラセニル基、フェナントリル基、ナフタセニル基、ピレニル基、ビフェニリル基、ｐ－ターフェニル基、ｍ－ターフェニル基、クリセニル基、トリフェニレニル基、ペリレニル基、インデニル基、フラニル基、チオフェニル基、ピロリル基、ピラゾリル基、イミダゾリル基、トリアゾリル基、オキサゾリル基、チアゾリル基、オキサジアゾリル基、チアジアゾリル基、ピリジル基、ピリミジニル基、ピラジニル基、トリアジニル基、ベンゾフラニル基、ベンゾチオフェニル基、ベンズイミダゾリル基、インドリル基、キノリニル基、イソキノリニル基、キナゾリニル基、キノキサリニル基、ナフチリジニル基、ベンズオキサジニル基、ベンズチアジニル基、アクリジニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基またはこれらの組み合わせであり得るが、これに制限されない。また、これらの「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」は置換基を有していてもよく、当該置換基としては、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Disubstituted amino group substituted by a group selected from the group consisting of an aromatic hydrocarbon group, an aromatic heterocyclic group and a fused polycyclic aromatic group represented by R 19 to R 34 in the general formula (3) Specifically, as the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the above, there may be mentioned phenyl group, naphthyl group, anthracenyl group, phenanthryl group, naphthacenyl group, pyrenyl group Group, biphenylyl group, p-terphenyl group, m-terphenyl group, chrysenyl group, triphenylenyl group, perylenyl group, indenyl group, furanyl group, thiophenyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, oxazolyl group, Thiazolyl group, oxadiazolyl group, thiadiazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl , Benzofuranyl group, benzothiophenyl group, benzimidazolyl group, indolyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, benzoxazinyl group, benzthiazinyl group, acridinyl group, phenazinyl group, phenothiazinyl group It may be, but is not limited to, phenoxazinyl groups or combinations thereof. In addition, these “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” may have a substituent, and examples of the substituent include the compounds represented by the general formula (1) The same as the “substituents” in “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted fused polycyclic aromatic group” represented by Ar 1 to Ar 4 in The thing which can be mentioned and the aspect which can take can mention the same thing.
　一般式（４）中のＡｒ８～Ａｒ１０で表される、「置換もしくは無置換の芳香族炭化水素基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、テトラキスフェニル基、スチリル基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基のような基をあげることができる。 “Aromatic hydrocarbon group” in “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted fused polycyclic aromatic group” represented by Ar 8 to Ar 10 in the general formula (4) Or “condensed polycyclic aromatic group” specifically includes phenyl group, biphenylyl group, terphenylyl group, tetrakisphenyl group, styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group And groups such as pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group.
　一般式（４）中のＡｒ８～Ａｒ１０で表される、「置換芳香族炭化水素基」または「置換縮合多環芳香族基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 As the “substituent” in the “substituted aromatic hydrocarbon group” or the “substituted fused polycyclic aromatic group” represented by Ar 8 to Ar 10 in the general formula (4) The same as those described for the "substituent" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted fused polycyclic aromatic group" represented by Ar 1 to Ar 4 The same can be mentioned as possible embodiments.
　構造式（５）中のＡｒ１１で表される、「置換もしくは無置換の芳香族複素環基」における「芳香族複素環基」としては、具体的に、トリアジニル基、ピリジル基、ピリミジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、カルボリニル基のような基をあげることができる。 Specific examples of the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 11 in the structural formula (5) include a triazinyl group, a pyridyl group and a pyrimidinyl group, Furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group And dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, carborinyl group and the like.
　構造式（５）中のＡｒ１１で表される、「置換芳香族複素環基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される、「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 As a “substituent” in the “substituted aromatic heterocyclic group” represented by Ar 11 in the structural formula (5), a “substituted aroma represented by Ar 1 to Ar 4 in the general formula (1) Groups similar to those described for the "substituent" in the "group hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted fused polycyclic aromatic group" can be mentioned, and the possible embodiments are also the same. I can give something.
　構造式（５）中のＲ３５～Ｒ３８で表される、「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、２－メチルプロピル基、ｔ－ブチル基、ｎ－ペンチル基、３－メチルブチル基、ｔｅｒｔ－ペンチル基、ｎ－ヘキシル基、ｉｓｏ－ヘキシル基およびｔｅｒｔ－ヘキシル基をあげることができる。 Specific examples of “a C1-C6 linear or branched alkyl group” represented by R 35 to R 38 in the structural formula (5) include a methyl group, an ethyl group and an n- group. Propyl, i-propyl, n-butyl, 2-methylpropyl, t-butyl, n-pentyl, 3-methylbutyl, tert-pentyl, n-hexyl, iso-hexyl and tert -A hexyl group can be mentioned.
　構造式（５）中のＲ３５～Ｒ３８で表される、「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、テトラキスフェニル基、スチリル基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、トリアジニル基、ピリジル基、ピリミジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、カルボリニル基のような基をあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensation group” represented by R 35 to R 38 in the structural formula (5) Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the polycyclic aromatic group include phenyl group, biphenylyl group, terphenylyl group, tetrakisphenyl group , Styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group , Thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, Groups such as basilyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl and carborinyl groups be able to.
　構造式（５）中のＲ３５～Ｒ３８で表される、「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される、「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 As a “substituent” in the “substituted aromatic hydrocarbon group”, the “substituted aromatic heterocyclic group” or the “substituted fused polycyclic aromatic group” represented by R 35 to R 38 in the structural formula (5) And the “substituent group” in the “substituted aromatic hydrocarbon group”, the “substituted aromatic heterocyclic group” or the “substituted fused polycyclic aromatic group” represented by Ar 1 to Ar 4 in the general formula (1) The same thing can be mentioned as what was shown regarding ", and the aspect which can take can mention the same thing.
　一般式（４）中のＡｒ８としては、フェニル基、ビフェニリル基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基が好ましく、フェニル基、ビフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基がより好ましい。ここで、フェニル基は置換もしくは無置換の縮合多環芳香族基を置換基として有していることが好ましく、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基から選ばれる置換基を有していることがより好ましい。
　一般式（４）中のＡｒ９としては、置換基を有するフェニル基が好ましく、この場合の置換基としては、フェニル基、ビフェニリル基、ターフェニル基などの芳香族炭化水素基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの縮合多環芳香族基が好ましく、フェニル基、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基がより好ましい。
　一般式（４）中のＡｒ１０としては、置換基を有するフェニル基が好ましく、この場合の置換基としては、フェニル基、ビフェニリル基、ターフェニル基などの芳香族炭化水素基、ナフチル基、アントラセニル基、アセナフテニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの縮合多環芳香族基が好ましく、フェニル基、ナフチル基、アントラセニル基、フェナントレニル基、ピレニル基、フルオランテニル基、トリフェニレニル基がより好ましい。 As Ar 8 in the general formula (4), a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, an acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group Preferably, a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group and a triphenylenyl group are more preferable. Here, the phenyl group preferably has a substituted or non-substituted fused polycyclic aromatic group as a substituent, and is selected from a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group and a triphenylenyl group. It is more preferable to have a substituted substituent.
As Ar 9 in the general formula (4), a phenyl group having a substituent is preferable, and as the substituent in this case, an aromatic hydrocarbon group such as phenyl group, biphenylyl group, terphenyl group, naphthyl group, anthracenyl group And fused polycyclic aromatic groups such as acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group are preferable, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, Pyrenyl group, fluoranthenyl group and triphenylenyl group are more preferable.
As Ar 10 in the general formula (4), a phenyl group having a substituent is preferable, and as the substituent in this case, an aromatic hydrocarbon group such as phenyl group, biphenylyl group, terphenyl group, naphthyl group, anthracenyl group And fused polycyclic aromatic groups such as acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group are preferable, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, Pyrenyl group, fluoranthenyl group and triphenylenyl group are more preferable.
　構造式（５）中のＡｒ１１としては、トリアジニル基、ピリジル基、ピリミジニル基、ピロリル基、キノリル基、イソキノリル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、カルボリニル基などの含窒素複素環基が好ましく、トリアジニル基、ピリジル基、ピリミジニル基、キノリル基、イソキノリル基、インドリル基、キノキサリニル基、ベンゾイミダゾリル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基がより好ましく、ピリジル基、ピリミジニル基、キノリル基、イソキノリル基、インドリル基、キノキサリニル基、ベンゾイミダゾリル基、フェナントロリニル基、アクリジニル基が特に好ましい。 As Ar 11 in the structural formula (5), a triazinyl group, a pyridyl group, a pyrimidinyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl group And nitrogen-containing heterocyclic groups such as pyrazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group and carborinyl group are preferable, and triazinyl group, pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, quinoxalinyl group, benzimidazolyl group Group, naphthyridinyl group, phenanthrolinyl group, acridinyl group is more preferable, and pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, quinoxalinyl group, benzimidazolyl group, phenanthrolyl group. Particular preference is given to nyl and acridinyl.
　一般式（６）中のＡｒ１２、Ａｒ１３およびＶ１で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、スピロビフルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピリミジニル基、トリアジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、およびカルボリニル基などのような基をあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 12 , Ar 13 and V 1 in the general formula (6) Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the above fused polycyclic aromatic group include phenyl group, biphenylyl group, terphenylyl group, and naphthyl. Group, anthracenyl group, phenanthrenyl group, fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, Thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, Groups such as oxo oxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carborinyl group can be exemplified.
　構造式（６）中のＡｒ１２、Ａｒ１３およびＶ１で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「置換基」として、前記一般式（１）中のＡｒ１～Ａｒ４で表される、「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 12 , Ar 13 and V 1 in the structural formula (6) The “substituted aromatic hydrocarbon group” or the “substituted aromatic heterocyclic group” represented by Ar 1 to Ar 4 in the general formula (1) as the “substituent” of the fused polycyclic aromatic group of Or the thing similar to what was shown regarding the "substituent" in "a substituted fused polycyclic aromatic group" can be mentioned, and the aspect which can take can also mention the same thing.
　一般式（６）中のＶ１で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」、または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」、または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、および２－ブテニル基などのような基をあげることができる。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted” represented by V 1 in the general formula (6), or “having a substituent” "C1-C6 cycloalkyl group" in "C5-C10 cycloalkyl group" or "C2-C6 linear or branched alkenyl group optionally having substituent (s)" As the linear or branched alkyl group, the "C5-C10 cycloalkyl group", or the "C2-C6 linear or branched alkenyl group", specifically, Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexene group Groups such as sil, 1-adamantyl, 2-adamantyl, vinyl, allyl, isopropenyl and 2-butenyl may be mentioned.
　一般式（６）中のＶ１で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」、または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては前記一般式（１）中のＲ１～Ｒ３で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted” represented by V 1 in the general formula (6), or “having a substituent” Examples of the “substituent” in the good cycloalkyl group having 5 to 10 carbon atoms or “a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent (s)” “A C1-C6 linear or branched alkyl group having a substituent, represented by R 1 to R 3 in the formula (1),“ a 5- to 10-carbon atom having a substituent, Mention may be made of the same ones as described for "substituent" in "cycloalkyl group" or "C2-C6 linear or branched alkenyl group having a substituent", and possible embodiments Can give the same thing Ru.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、具体的に、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基、シクロペンチル基、シクロヘキシル基、１－アダマンチル基、２－アダマンチル基、ビニル基、アリル基、イソプロペニル基、２－ブテニル基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 “A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent,” represented by R 39 to R 44 in the general formula (7), “having a substituent” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)” As the linear or branched alkyl group of 6, the "C5-C10 cycloalkyl group" or the "C2-C6 linear or branched alkenyl group" are specifically mentioned Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, And Rhexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group, 2-butenyl group and the like, and these groups may be a single bond, a substituted or unsubstituted methylene group, They may be bonded to each other via an oxygen atom or a sulfur atom to form a ring.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；ビニル基、アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基のような基をあげることができ、これらの置換基はさらに、前記例示した置換基が置換していても良い。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “C1-C6 linear or branched alkyl group having a substituent, which is represented by R 39 to R 44 in the general formula (7),“ c-5 having a substituent ” Specific examples of the "substituent" in the cycloalkyl group of "" or "C2-C6 linear or branched alkenyl group having a substituent" include deuterium atom, cyano group, nitro group; A halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group An alkenyl group such as a phenyl group, an aryloxy group such as a tolyloxy group, an arylalkyloxy group such as a benzyloxy group or a phenethyloxy group; Aromatic hydrocarbon group or fused polycyclic aromatic group such as nyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, etc. Group: pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group And groups such as aromatic heterocyclic groups such as benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carborinyl group, etc., and these substituents may be further substituted by the above-mentioned substituents. Even if There. In addition, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、具体的に、メチルオキシ基、エチルオキシ基、ｎ－プロピルオキシ基、イソプロピルオキシ基、ｎ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、１－アダマンチルオキシ基、２－アダマンチルオキシ基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。
　また、これらの基は置換基を有していてよく、置換基として、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent,” represented by R 39 to R 44 in the general formula (7), or “having a substituent” "C1-C6 linear or branched alkyloxy group" or "C5-C10 cycloalkyloxy group" in the optionally substituted C5-C10 cycloalkyloxy group " As “specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group , Cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group Etc. can be mentioned groups, these groups to each other is a single bond, a substituted or unsubstituted methylene group, via an oxygen atom or a sulfur atom may bond to each other to form a ring.
In addition, these groups may have a substituent, and as the substituent, “a linear group having 1 to 6 carbon atoms having a substituent, represented by R 39 to R 44 in the general formula (7), Or branched or branched alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, or a substituted or unsubstituted linear or branched alkenyl group having 2 to 6 carbon atoms Examples similar to those described for the "substituent" can be mentioned, and the possible embodiments can also be mentioned the same.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、具体的に、フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基、ピリジル基、ピリミジニル基、トリアジニル基、フリル基、ピロリル基、チエニル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、ナフチリジニル基、フェナントロリニル基、アクリジニル基、およびカルボリニル基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 39 to R 44 in the general formula (7), or “substituted or unsubstituted fused multiple ring” Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "fused polycyclic aromatic group" in the ring aromatic group include phenyl group, biphenylyl group, terphenylyl group, naphthyl group and anthracenyl group Group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group Group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group Examples include quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, carborinyl group and the like, and these groups are a single bond, substituted or They may be bonded to each other via an unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「置換基」としては、具体的に、重水素原子、シアノ基、ニトロ基；フッ素原子、塩素原子、臭素原子、ヨウ素原子などのハロゲン原子；メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、ｎ－ヘキシル基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基；メチルオキシ基、エチルオキシ基、プロピルオキシ基などの炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基；ビニル基、アリル基などのアルケニル基；フェニルオキシ基、トリルオキシ基などのアリールオキシ基；ベンジルオキシ基、フェネチルオキシ基などのアリールアルキルオキシ基；フェニル基、ビフェニリル基、ターフェニリル基、ナフチル基、アントラセニル基、フェナントレニル基、フルオレニル基、インデニル基、ピレニル基、ペリレニル基、フルオランテニル基、トリフェニレニル基などの芳香族炭化水素基もしくは縮合多環芳香族基；ピリジル基、ピリミジニル基、トリアジニル基、チエニル基、フリル基、ピロリル基、キノリル基、イソキノリル基、ベンゾフラニル基、ベンゾチエニル基、インドリル基、カルバゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノキサリニル基、ベンゾイミダゾリル基、ピラゾリル基、ジベンゾフラニル基、ジベンゾチエニル基、カルボリニル基などの芳香族複素環基；スチリル基、ナフチルビニル基などのアリールビニル基；アセチル基、ベンゾイル基などのアシル基；トリメチルシリル基、トリフェニルシリル基などのシリル基のような基をあげることができ、これらの置換基は、さらに前記例示した置換基が置換していても良い。また、これらの置換基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 39 to R 44 in the general formula (7), or “substituted or unsubstituted fused multiple ring” Specific examples of the "substituent" in the "ring aromatic group" include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl group, n -C1-C6 linear or branched, such as -propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl and the like Alkyl groups having 1 to 6 carbon atoms, such as methyloxy, ethyloxy, propyloxy, etc .; and alkyloxy groups having 1 to 6 carbon atoms, such as vinyl, allyl, etc. Phenyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, Aromatic hydrocarbon group or condensed polycyclic aromatic group such as indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl Group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibe Aromatic heterocyclic groups such as zothienyl group, carborinyl group; aryl vinyl groups such as styryl group, naphthyl vinyl group; acyl groups such as acetyl group and benzoyl group; groups such as silyl group such as trimethylsilyl group and triphenylsilyl group These substituents may be further substituted by the substituents exemplified above. In addition, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、具体的に、フェニルオキシ基、ビフェニリルオキシ基、ターフェニリルオキシ基、ナフチルオキシ基、アントラセニルオキシ基、フェナントレニルオキシ基、フルオレニルオキシ基、インデニルオキシ基、ピレニルオキシ基、ペリレニルオキシ基などをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成していてもよい。 Specific examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R 39 to R 44 in the general formula (7) include a phenyloxy group, a biphenylyloxy group and a terphenyl group. Ryloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc. can be mentioned, and these groups are single They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換のアリールオキシ基」における「置換基」としては前記一般式（１）中のＲ１～Ｒ３で表される「置換もしくは無置換のアリールオキシ基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 The “substituent” in the “substituted or unsubstituted aryloxy group” represented by R 39 to R 44 in the general formula (7) is represented by R 1 to R 3 in the general formula (1) The same groups as those described for the "substituent" in the "substituted or unsubstituted aryloxy group" can be mentioned, and the same can be mentioned as possible modes.
　一般式（７）において、ｒ１～ｒ６は同一でも異なっていてもよく、ｒ１～ｒ４は０～５の整数を表し、ｒ５、ｒ６は０～４の整数を表す。ｒ１～ｒ４が２～５の整数である場合、または、ｒ５、ｒ６が２～４の整数である場合、同一のベンゼン環に複数個結合するＲ３９～Ｒ４４はそれぞれ同一でも異なっていてもよく、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 In the general formula (7), r 1 to r 6 may be the same or different, r 1 to r 4 represent an integer of 0 to 5, and r 5 and r 6 represent an integer of 0 to 4. When r 1 to r 4 are integers of 2 to 5 or r 5 and r 6 are integers of 2 to 4, R 39 to R 44 bound to a plurality of identical benzene rings may be identical to each other They may be different from each other, and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（７）中のＫ１で表される「２価の連結基」としては、メチレン基、エチレン基、ｎ－プロピリレン基、イソプロピリレン基、ｎ－ブチリレン基、イソブチリレン基、ｔｅｒｔ－ブチリレン基、ｎ－ペンチリレン基、イソペンチリレン基、ネオペンチリレン基、ｎ－ヘキシリレン基などの「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキレン基」；シクロペンチリレン基、シクロヘキシリレン基、アダマンチリレン基などの「炭素原子数５ないし１０のシクロアルキレン基」；ビニレン基、アリレン基、イソプロペニレン基、ブテニレン基などの「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニレン基」；ベンゼン、ビフェニル、ターフェニル、テトラキスフェニルなどの芳香族炭化水素から水素原子を２個取り除いてできる「芳香族炭化水素の２価基」；ナフタレン、アントラセン、アセナフタレン、フルオレン、フェナントレン、インダン、ピレン、トリフェニレンなどの縮合多環芳香族から水素原子を２個取り除いてできる「縮合多環芳香族の２価基」のような２価基をあげることができる。
　また、これらの２価基は置換基を有していてよい。「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキレン基」、「炭素原子数５ないし１０のシクロアルキレン基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニレン基」の置換基として、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができる。「芳香族炭化水素の２価基」または「縮合多環芳香族の２価基」の置換基として、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。
　一般式（７）中のＫ１で表される「２価の連結基」の好ましい態様としては、上記構造式（ＨＴＭ－Ａ）～（ＨＴＭ－Ｆ）で示される２価基が挙げられる。 As the “divalent linking group” represented by K 1 in the general formula (7), a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butyrylene group, an isobutyrylene group, a tert-butyrylene group And "a C1-C6 linear or branched alkylene group such as n-pentylidene group, isopentylylene group, neopentylene group, n-hexyrylene group"; cyclopentylylene group, cyclohexyarylene group, adamantylylene group And the like. "C5-C10 cycloalkylene group";"vinylene group, allylene group, isopropenylene group, butenylene group" and the like "C2-C6 linear or branched alkenylene group"; benzene Of two hydrogen atoms from aromatic hydrocarbons such as biphenyl, terphenyl and tetrakisphenyl “Divalent group of aromatic hydrocarbon”; “condensed polycyclic aromatics” obtained by removing two hydrogen atoms from fused polycyclic aromatics such as naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene, indane, pyrene and triphenylene It is possible to cite bivalent groups such as “group bivalent group”.
Moreover, these bivalent groups may have a substituent. "C1-C6 linear or branched alkylene group", "C5-C10 cycloalkylene group" or "C2-C6 linear or branched alkenylene group" As the substituent of “a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent” represented by R 39 to R 44 in the general formula (7), “having a substituent” Examples similar to those described for "substituent" in "C5-C10 cycloalkyl group" or "C2-C6 linear or branched alkenyl group having substituent group" Can. As a substituent of “aromatic hydrocarbon bivalent group” or “fused polycyclic aromatic bivalent group”, “substituted or unsubstituted one represented by R 39 to R 44 in the above general formula (7) The same as those described for "substituent" in the "aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted fused polycyclic aromatic group" may be mentioned The same can be mentioned as possible embodiments.
Preferred embodiments of the “divalent linking group” represented by K 1 in the general formula (7) include the divalent groups represented by the above structural formulas (HTM-A) to (HTM-F).
　一般式（８）中のＲ４５～Ｒ５６で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基」または「置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「炭素原子数５ないし１０のシクロアルキル基」または「炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyl group optionally having substituent (s), which may be substituted, represented by R 45 to R 56 in the general formula (8),“ having a substituent ” C 1 -C 10 cycloalkyl group which may be substituted or substituted by “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group which may have a substituent (s)” As the “6 linear or branched alkyl group”, “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group”, the above general formula “A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent,” represented by R 39 to R 44 in (7), “having a substituent Cycloalkyl having 5 to 10 carbon atoms Or “a C 1 -C 6 linear or branched alkyl group” in the “C 2 -C 6 linear or branched alkenyl group optionally having substituent (s)”, “ Mention may be made of the same ones as described for the cycloalkyl group having 5 to 10 carbon atoms or the "linear or branched alkenyl group having 2 to 6 carbon atoms", and the possible modes are also the same. I can give you something.
　一般式（８）中のＲ４５～Ｒ５６で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基」、「置換基を有する炭素原子数５ないし１０のシクロアルキル基」または「置換基を有する炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyl group having a substituent, which is represented by R 45 to R 56 in the general formula (8),“ c-5 having a substituent ” Examples of the “substituent” in the “cycloalkyl group” or the “C2-C6 linear or branched alkenyl group having a substituent” are R 39 to R 44 in the general formula (7). “C1-C6 linear or branched alkyl group having a substituent group”, “C5-C10 cycloalkyl group having a substituent group” or “carbon atom having a substituent group” The same groups as those described with respect to the “substituent” in the “2 to 6 straight or branched alkenyl group” can be mentioned, and the same can be mentioned as possible modes.
　一般式（８）中のＲ４５～Ｒ５６で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基」における「炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「炭素原子数５ないし１０のシクロアルキルオキシ基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Having a substituted or unsubstituted linear or branched alkyloxy group having 1 to 6 carbon atoms” represented by R 45 to R 56 in the general formula (8) or “having a substituent” "C1-C6 linear or branched alkyloxy group" or "C5-C10 cycloalkyloxy group" in the optionally substituted C5-C10 cycloalkyloxy group " Is a “C1-C6 linear or branched alkyloxy group optionally having substituent (s)” represented by R 39 to R 44 in the general formula (7), or "C1-C6 linear or branched alkyloxy group" in "C5-C10 cycloalkyloxy group optionally having substituent (s)" or "C5-C10 carbon atom of Black alkyl group "can be mentioned the same as those shown with respect to, aspects that can be taken can also be mentioned those similar.
　一般式（８）中のＲ４５～Ｒ５６で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有する炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基」または「置換基を有する炭素原子数５ないし１０のシクロアルキルオキシ基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “C1-C6 linear or branched alkyloxy group having a substituent, represented by R 45 to R 56 in the general formula (8), or“ c5-C having a substituent ” Examples of the “substituent” in the cycloalkyloxy group of 10 ”include linear or branched C 1 to C 6 carbon atoms having a substituent represented by R 39 to R 44 in the general formula (7) The same as those described for "substituent" in "alkyloxy group" or "C5-C10 cycloalkyloxy group having a substituent" can be exemplified, and the possible embodiments are also the same You can raise
　一般式（８）中のＲ４５～Ｒ５６で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換の芳香族炭化水素基」、「置換もしくは無置換の芳香族複素環基」または「置換もしくは無置換の縮合多環芳香族基」における「芳香族炭化水素基」、「芳香族複素環基」または「縮合多環芳香族基」に関して示したものと同様のものをあげることができ、これらの基同士が単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。
　また、これらの基は置換基を有していてよく、置換基として、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換芳香族炭化水素基」、「置換芳香族複素環基」または「置換縮合多環芳香族基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 “Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R 45 to R 56 in the general formula (8), or “substituted or unsubstituted fused multiple ring” The “aromatic hydrocarbon group”, the “aromatic heterocyclic group” or the “fused polycyclic aromatic group” in the ring aromatic group is represented by R 39 to R 44 in the general formula (7) "Aromatic hydrocarbon group" in "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted fused polycyclic aromatic group", "aromatic" Group may be the same as those described with regard to “heterocyclic group” or “fused polycyclic aromatic group”, and these groups may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom You may combine with each other to form a ring
In addition, these groups may have a substituent, and as the substituent, “substituted aromatic hydrocarbon group” represented by R 39 to R 44 in the general formula (7), “substituted aromatic complex The same groups as those described for "substituent" in the "ring group" or "substituted fused polycyclic aromatic group" can be mentioned, and the same can be mentioned as possible embodiments.
　一般式（８）中のＲ４５～Ｒ５６で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換もしくは無置換のアリールオキシ基」における「アリールオキシ基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 Examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R 45 to R 56 in the general formula (8) are represented by R 39 to R 44 in the general formula (7). The same as those described for the "aryloxy group" in the "substituted or unsubstituted aryloxy group" can be mentioned, and the same can be mentioned as possible embodiments.
　一般式（８）中のＲ４５～Ｒ５６で表される「置換基を有するアリールオキシ基」における「置換基」としては、前記一般式（７）中のＲ３９～Ｒ４４で表される「置換基を有するアリールオキシ基」における「置換基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 The “substituent” in the “aryloxy group having a substituent” represented by R 45 to R 56 in the general formula (8) is represented by R 39 to R 44 in the general formula (7) The thing similar to what was shown regarding the "substituent" in the "aryloxy group which has a substituent" can be mentioned, and the aspect which can take can also mention the same thing.
　一般式（８）において、ｒ７～ｒ１８は同一でも異なってもよく、ｒ７～ｒ１２は０～５の整数を表し、ｒ１３～ｒ１８は０～４の整数を表す。ｒ７～ｒ１２が２～５の整数である場合、または、ｒ１３～ｒ１８が２～４の整数である場合、同一のベンゼン環に複数個結合するＲ４５～Ｒ５６はそれぞれ同一でも異なっていてもよく、単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子を介して互いに結合して環を形成してもよい。 In the general formula (8), r 7 to r 18 may be the same or different, r 7 to r 12 represent an integer of 0 to 5, and r 13 to r 18 represent an integer of 0 to 4. When r 7 to r 12 is an integer of 2 to 5 or r 13 to r 18 is an integer of 2 to 4, R 45 to R 56 bonded to the same benzene ring may be identical to each other They may be different from each other, and may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
　一般式（８）中のＫ２、Ｋ３、Ｋ４で表される「２価の連結基」としては、前記一般式（７）中のＫ１で表される「２価の連結基」に関して示したものと同様のものをあげることができ、とりうる態様も、同様のものをあげることができる。 Examples of the “divalent linking group” represented by K 2 , K 3 and K 4 in the general formula (8) include “bivalent linking group” represented by K 1 in the general formula (7). The same thing can be mentioned as what was shown about, and the aspect which can take can mention the same thing.
　本実施形態の一般式（１）で表される、アリールアミン化合物は新規の化合物であり、従来の正孔輸送材料より、優れた三重項励起子を閉じ込める能力を有し、優れた正孔輸送能を有し、優れたアモルファス性を有し、かつ薄膜状態が安定である。 The arylamine compound represented by the general formula (1) of the present embodiment is a novel compound, and has an excellent ability to trap triplet excitons and excellent hole transport than conventional hole transport materials. Active, has excellent amorphous property, and is stable in thin film state.
　本実施形態の一般式（１）で表されるアリールアミン化合物は、有機ＥＬ素子の発光層に隣接した第二正孔輸送層および／または発光層のホスト材料として使用することができる。従来の材料に比べて正孔の注入性が高く、移動度が大きく、電子阻止性が高く、しかも電子に対する安定性が高い材料を用いることによって、発光層内で生成した励起子を閉じ込めることができる。これにより、さらに正孔と電子が再結合する確率を向上させ、高発光効率を得ることができる。それと共に、駆動電圧が低下して、有機ＥＬ素子の耐久性が向上するという作用が得られる。 The arylamine compound represented by General formula (1) of this embodiment can be used as a host material of the 2nd positive hole transport layer adjacent to the light emitting layer of an organic EL element, and / or a light emitting layer. It is possible to confine excitons generated in the light emitting layer by using a material that has high hole injection property, high mobility, high electron blocking property, and high electron stability compared to conventional materials. it can. As a result, the probability that holes and electrons recombine can be further improved, and high luminous efficiency can be obtained. At the same time, the driving voltage is lowered, and the durability of the organic EL element is improved.
　本実施形態の一般式（１）で表されるアリールアミン化合物は、有機ＥＬ素子の発光層の構成材料としても使用することができる。当該化合物は、従来の材料に比べて正孔輸送性に優れ、特に緑色燐光性発光材料を含む場合に、より好適に有機ＥＬ素子の発光効率を向上させることができるという作用を有する。 The arylamine compound represented by General formula (1) of this embodiment can also be used as a constituent material of the light emitting layer of an organic EL element. The said compound is excellent in hole transportability compared with the conventional material, and when it contains a green phosphorescence light emitting material especially, it has the effect | action that the luminous efficiency of an organic EL element can be improved more suitably.
　本実施形態の有機ＥＬ素子は、従来の正孔輸送材料より正孔の移動度が大きく、優れた電子の阻止能力を有し、優れたアモルファス性を有し、かつ電気的な還元耐久性が優れた、アリールアミン化合物を用いている。そのため、高効率、高耐久性を実現することが可能となる。 The organic EL device of the present embodiment has hole mobility larger than that of the conventional hole transport material, has excellent electron blocking ability, has excellent amorphous property, and has electric reduction durability. An excellent arylamine compound is used. Therefore, high efficiency and high durability can be realized.
　一般式（１）で表されるアリールアミン化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Although the specific example of a preferable compound is shown below among the arylamine compounds represented by General formula (1), this invention is not limited to these compounds.
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000045
　尚、上述したアリールアミン化合物は、それ自体公知の方法に準じて合成することができる（例えば、特許文献８参照）。例えば、後述する実施例に示すように、ジ置換アミンとハロゲン化された置換芳香族炭化水素をカップリング反応により反応させて、得られた化合物をさらにハロゲン化させて芳香族炭化水素のボロン酸とカップリング反応により反応させることで、上述したアリールアミン化合物を合成することができる。 The above-described arylamine compound can be synthesized according to a method known per se (see, for example, Patent Document 8). For example, as shown in Examples described later, a disubstituted amine and a halogenated substituted aromatic hydrocarbon are reacted by a coupling reaction, and the resulting compound is further halogenated to obtain a boronic acid of an aromatic hydrocarbon. The arylamine compounds described above can be synthesized by reacting them with a coupling reaction.
　本実施形態の有機ＥＬ素子に好適に用いられる、化学式（Ｈｏｓｔ－Ａ）で表される化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the compounds represented by the chemical formula (Host-A) suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is limited to these compounds It is not a thing.
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
　尚、上述した含窒素ヘテロ芳香族環構造を有する化合物は、それ自体公知の方法に準じて合成することができる（例えば、特許文献４、５参照） The above-mentioned compound having a nitrogen-containing heteroaromatic ring structure can be synthesized according to a method known per se (see, for example, Patent Documents 4 and 5).
　本実施形態の有機ＥＬ素子に好適に用いられる、化学式（Ｈｏｓｔ－Ｂ）で表される化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the compounds represented by the chemical formula (Host-B) suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is limited to these compounds It is not a thing.
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000055
　尚、上述した含カルバゾール構造を有する化合物は、それ自体公知の方法に準じて合成することができる（例えば、特許文献４、５参照）。 The compounds having a carbazole-containing structure described above can be synthesized according to a method known per se (see, for example, Patent Documents 4 and 5).
　本実施形態の有機ＥＬ素子に好適に用いられる、化学式（３）で表される化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the compounds represented by the chemical formula (3) suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is not limited to these compounds. Absent.
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000057
　尚、上述したイリジウム錯体は、それ自体公知の方法に準じて合成することができる（例えば、特許文献９、１０参照）。 The above-mentioned iridium complex can be synthesized according to a method known per se (see, for example, Patent Documents 9 and 10).
　本実施形態の有機ＥＬ素子に好適に用いられる、前記一般式（４）で表されるピリミジン環構造を有する化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the compounds having a pyrimidine ring structure represented by the general formula (4), which are suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is not limited thereto. It is not limited to the compounds.
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000062
Figure JPOXMLDOC01-appb-C000062
　尚、上述したピリミジン環構造を有する化合物は、それ自体公知の方法によって合成することができる（例えば、特許文献１０、１１参照）。 The compounds having a pyrimidine ring structure described above can be synthesized by a method known per se (see, for example, Patent Documents 10 and 11).
　本実施形態の有機ＥＬ素子に好適に用いられる、前記一般式（６）で表されるベンゾアゾール環構造を有する化合物の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the compounds having the benzoazole ring structure represented by the general formula (6), which are suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention It is not limited to the compounds of
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000064
Figure JPOXMLDOC01-appb-C000064
Figure JPOXMLDOC01-appb-C000065
Figure JPOXMLDOC01-appb-C000065
Figure JPOXMLDOC01-appb-C000066
Figure JPOXMLDOC01-appb-C000066
　尚、上述したベンゾアゾール環構造を有する化合物は、それ自体公知の方法に準じて合成することができる（例えば、特許文献１３，１４）。 The above-mentioned compound having a benzoazole ring structure can be synthesized according to a method known per se (for example, Patent Documents 13 and 14).
　本実施形態の有機ＥＬ素子に好適に用いられる、前記一般式（７）で表されるトリフェニルアミン誘導体の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the triphenylamine derivatives represented by the above general formula (7) which are suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is not limited to these compounds. It is not limited.
Figure JPOXMLDOC01-appb-C000067
Figure JPOXMLDOC01-appb-C000067
Figure JPOXMLDOC01-appb-C000068
Figure JPOXMLDOC01-appb-C000068
　本実施形態の有機ＥＬ素子に好適に用いられる、前記一般式（８）で表されるトリフェニルアミン誘導体の中で、好ましい化合物の具体例を以下に示すが、本発明は、これらの化合物に限定されるものではない。 Among the triphenylamine derivatives represented by the general formula (8), which are suitably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown below, but the present invention is not limited to these compounds. It is not limited.
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000070
　尚、上述したトリアリールアミン構造を有する化合物は、それ自体公知の方法に準じて合成することができる（例えば、特許文献１、２および特許文献１５参照）。 The compound having a triarylamine structure described above can be synthesized according to a method known per se (see, for example, Patent Documents 1, 2 and 15).
　一般式（１）～（８）、（ＨＯＳＴ－Ａ）および（ＨＯＳＴ－Ｂ）の精製はカラムクロマトグラフによる精製、シリカゲル、活性炭、活性白土等による吸着精製、溶媒による再結晶や晶析法、昇華精製法などによって行える。化合物の同定は、ＮＭＲ分析によって行える。物性値として、融点、ガラス転移点（Ｔｇ）と仕事関数の測定を行う。融点は蒸着性の指標となるものであり、ガラス転移点（Ｔｇ）は薄膜状態の安定性の指標となり、仕事関数は正孔輸送性や正孔阻止性の指標となるものである。
　その他、本実施形態の有機ＥＬ素子に用いられる化合物としては、カラムクロマトグラフによる精製、シリカゲル、活性炭、活性白土等による吸着精製、溶媒による再結晶や晶析法などによって精製を行った後、最後に昇華精製法によって精製されたものを用いる。 Purification of the general formulas (1) to (8), (HOST-A) and (HOST-B) is purification by column chromatography, adsorption purification with silica gel, activated carbon, activated clay or the like, recrystallization or crystallization method with a solvent, It can be performed by a sublimation purification method or the like. Identification of compounds can be done by NMR analysis. As physical property values, measurement of melting point, glass transition point (Tg) and work function is performed. The melting point is an index of vapor deposition property, the glass transition point (Tg) is an index of stability of the thin film state, and the work function is an index of hole transporting property or hole blocking property.
In addition, as a compound used for the organic EL element of the present embodiment, after purification by column chromatography, adsorption purification with silica gel, activated carbon, activated clay or the like, recrystallization with a solvent or crystallization method, etc. Use those purified by the sublimation purification method.
　融点とガラス転移点（Ｔｇ）は、粉体を用いて高感度示走査熱量計（ブルカー・エイエックスエス製、ＤＳＣ３１００ＳＡ）によって測定できる。 The melting point and the glass transition point (Tg) can be measured using a powder by a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS).
　仕事関数は、ＩＴＯ基板の上に１００ｎｍの薄膜を作製して、イオン化ポテンシャル測定装置（住友重機械工業株式会社製、ＰＹＳ－２０２）によって求めることができる。 The work function can be obtained by preparing a thin film of 100 nm on an ITO substrate and using an ionization potential measurement device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).
　これらの化合物のＴ１は、測定した燐光スペクトルより算出できる。燐光スペクトルは市販の分光光度計を用いて測定できる。一般的な燐光スペクトルの測定方法としては溶媒に溶解し、低温下励起光を照射して測定する方法（例えば、非特許文献３参照）、あるいは、シリコン基板上に蒸着して薄膜とし、低温下励起光を照射して燐光スペクトルを測定する方法などがある（例えば、特許文献１６参照）。Ｔ１は、燐光スペクトルの短波長側の第１ピークの波長あるいは短波長側の立ち上がり位置の波長を読み取り、下記の式に従って光のエネルギー値に換算することによって算出できる。Ｔ１は燐光発光体の三重項励起子の閉じ込め能の指標となる。 T1 of these compounds can be calculated from the measured phosphorescence spectrum. The phosphorescence spectrum can be measured using a commercially available spectrophotometer. A general method of measuring the phosphorescence spectrum is a method of dissolving in a solvent and irradiating it with excitation light at low temperature (for example, see Non-Patent Document 3), or depositing it on a silicon substrate to form a thin film There is a method of measuring excitation light and measuring a phosphorescence spectrum (see, for example, Patent Document 16). T1 can be calculated by reading the wavelength of the first peak on the short wavelength side of the phosphorescence spectrum or the wavelength of the rising position on the short wavelength side and converting it into the energy value of light according to the following equation. T1 is an indicator of the trapping ability of the triplet exciton of the phosphorescence material.
Figure JPOXMLDOC01-appb-M000071
Figure JPOXMLDOC01-appb-M000071
　ここで、Ｅは光エネルギーの値を、ｈはプランク定数（６．６３×１０－３４Ｊｓ）を、ｃは光速（３．００×１０８ｍ／ｓ）を、λは燐光スペクトルの短波長側の立ち上がるところの波長（ｎｍ）を表す。そして、１ｅＶは１．６０×１０－１９Ｊとなる。 Here, E is the light energy value, h is Planck's constant (6.63 × 10 -34 Js), c is the speed of light (3.00 × 10 8 m / s), λ is the short wavelength of the phosphorescence spectrum Represents the wavelength (nm) at which the side rises. Then, 1 eV is 1.60 × 10 −19 J.
　本実施形態の有機ＥＬ素子の構造としては、基板上に順次に、陽極、正孔注入層、第一正孔輸送層、第二正孔輸送層、発光層、電子輸送層、電子注入層および陰極が積層されたもの、また、当該構造に加えて発光層と電子輸送層との間に正孔阻止層を有するものがあげられる。これらの多層構造においては有機層を何層か省略あるいは兼ねることが可能であり、例えば電子注入層と電子輸送層とを兼ねた構成（層）とすること、などもできる。また、同一の機能を有する有機層を２層以上積層した構成とすることが可能であり、発光層を２層積層した構成、電子輸送層を２層積層した構成、などもできる。 The structure of the organic EL device of the present embodiment includes, in order on the substrate, an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and What has a cathode laminated | stacked, Moreover, what has a hole blocking layer between a light emitting layer and an electron carrying layer in addition to the said structure is mention | raise | lifted. In these multilayer structures, it is possible to omit or combine several organic layers, and for example, a configuration (layer) combining an electron injection layer and an electron transport layer can be used. In addition, two or more organic layers having the same function can be stacked, or two light emitting layers can be stacked, or two electron transporting layers can be stacked.
　本実施形態の有機ＥＬ素子の陽極としては、ＩＴＯや金のような仕事関数の大きな電極材料が用いられる。本実施形態の有機ＥＬ素子の正孔注入層として、前記一般式（７）、（８）で表されるアリールアミン化合物の他に、銅フタロシアニンに代表されるポルフィリン化合物、スターバースト型のトリフェニルアミン誘導体、ヘキサシアノアザトリフェニレンのようなアクセプター性の複素環化合物や塗布型の高分子材料を用いることができる。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the anode of the organic EL element of the present embodiment, an electrode material having a large work function such as ITO or gold is used. As the hole injection layer of the organic EL device of the present embodiment, in addition to the arylamine compounds represented by the general formulas (7) and (8), porphyrin compounds represented by copper phthalocyanine, triburst of starburst type Amine derivatives, acceptor heterocyclic compounds such as hexacyanoazatriphenylene and coated polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　本実施形態の有機ＥＬ素子の第一正孔輸送層として、前記一般式（７）、（８）で表されるアリールアミン化合物がより好ましいが、その他に、Ｎ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（ｍ－トリル）－ベンジジン（以後、ＴＰＤと略称する）やＮ，Ｎ’－ジフェニル－Ｎ，Ｎ’－ジ（α－ナフチル）－ベンジジン（以後、ＮＰＤと略称する）、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラビフェニリルベンジジンなどのベンジジン誘導体、１，１－ビス［(ジ－４－トリルアミノ)フェニル］シクロヘキサン（以後、ＴＡＰＣと略称する）なども用いることができる。これらは、単独で成膜しても良いが、他の材料とともに混合して成膜した単層として使用しても良く、上記複数の材料を単独で成膜した層同士、上記複数の材料を混合して成膜した層同士、または上記複数の材料を単独で成膜した層と混合して成膜した層との積層構造としても良い。また、正孔の注入・輸送層として、ポリ（３，４－エチレンジオキシチオフェン）（以後、ＰＥＤＯＴと略称する）／ポリ（スチレンスルフォネート）（以後、ＰＳＳと略称する）などの塗布型の高分子材料を用いることができる。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the first hole transport layer of the organic EL device of the present embodiment, the arylamine compounds represented by the general formulas (7) and (8) are more preferable, and in addition, N, N′-diphenyl-N, N'-di (m-tolyl) -benzidine (hereinafter abbreviated as TPD), N, N'-diphenyl-N, N'-di (α-naphthyl) -benzidine (hereinafter abbreviated as NPD), N Benzidine derivatives such as N, N ', N'-tetrabiphenylyl benzidine, 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), and the like can also be used. Although these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed by independently forming the above-mentioned plurality of materials, and the above-mentioned plurality of materials. A stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a plurality of the above materials alone may be employed. In addition, as a hole injection / transport layer, a coating type such as poly (3,4-ethylenedioxythiophene) (hereinafter referred to as PEDOT) / poly (styrene sulfonate) (hereinafter referred to as PSS), etc. Polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　また、正孔注入層あるいは正孔輸送層において、該層に通常使用される材料に対し、さらにトリスブロモフェニルアミンヘキサクロルアンチモン、ラジアレン誘導体（例えば、後述する化合物（Acceptor-1）、また特許文献１７参照）をＰドーピングしたものや、ＴＰＤなどのベンジジン誘導体の構造をその部分構造に有する高分子化合物などを用いることができる。 In addition, in the hole injection layer or the hole transport layer, trisbromophenylamine hexachloroantimony, a radialene derivative (for example, a compound (Acceptor-1) described later), and a patent document in addition to materials generally used in the layer. 17) may be P-doped, and a polymer compound having a structure of a benzidine derivative such as TPD in its partial structure may be used.
　本実施形態の有機ＥＬ素子の第二正孔輸送層として、本実施形態の一般式（１）で表されるアリールアミン化合物のほか、４，４’，４’’－トリ（Ｎ－カルバゾリル）トリフェニルアミン（以後、ＴＣＴＡと略称する）、９，９－ビス［４－（カルバゾール－９－イル）フェニル］フルオレン、１，３－ビス（カルバゾール－９－イル）ベンゼン（以後、ｍＣＰと略称する）、２，２－ビス（４－カルバゾール－９－イルフェニル）アダマンタン(以後、Ａｄ－Ｃｚと略称する)などのカルバゾール誘導体、９－［４－（カルバゾール－９－イル）フェニル］－９－［４－（トリフェニルシリル）フェニル］－９Ｈ－フルオレンに代表されるトリフェニルシリル基とトリアリールアミン構造を有する化合物などの電子阻止作用を有する化合物を用いることができる。これらは、単独で成膜しても良いが、他の材料とともに混合して成膜した単層として使用しても良く、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層との積層構造としても良い。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the second hole transport layer of the organic EL device of the present embodiment, in addition to the arylamine compound represented by the general formula (1) of the present embodiment, 4,4 ′, 4 ′ ′-tri (N-carbazolyl) Triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis [4- (carbazol-9-yl) phenyl] fluorene, 1,3-bis (carbazol-9-yl) benzene (hereinafter abbreviated as mCP) Carbazole derivatives such as 2, 2-bis (4-carbazol-9-ylphenyl) adamantane (hereinafter abbreviated as Ad-Cz), 9- [4- (carbazol-9-yl) phenyl] -9 Compound having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure represented by-[4- (triphenylsilyl) phenyl] -9H-fluorene It can be used. These layers may be formed separately, but may be used as a single layer formed by mixing with other materials, layers formed separately, layers formed by mixing, or layers A stacked structure of a layer formed separately and a layer formed by mixing may be employed. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　本実施形態の有機ＥＬ素子の発光層のホストとしては、正孔輸送性のホスト材料または電子輸送性のホスト材料を用いることができる。正孔輸送性のホスト材料としては、前記一般式（ＨＯＳＴ－Ｂ）で表されるカルバゾール環構造を有する化合物または本実施形態の一般式（１）で表されるアリールアミン化合物の他に、４，４’－ジ（Ｎ－カルバゾリル）ビフェニル（ＣＢＰ）やＴＣＴＡ、ｍＣＰなどのカルバゾール誘導体などを用いることができる。電子輸送性のホスト材料としては、前記一般式（ＨＯＳＴ－Ａ）で表される含窒素ヘテロ芳香族環構造を有する化合物の他に、ｐ－ビス（トリフェニルシリル）ベンゼン(ＵＧＨ２)や２，２’，２’’－(１，３，５－フェニレン)－トリス（１－フェニル－１Ｈ－ベンズイミダゾール）（ＴＰＢｉ）などを用いることができる。これらは、単独で成膜しても良いが、複数の材料を混合して成膜した単層として使用しても良く、単独で成膜した層同士、混合して成膜した層同士、または単独で成膜した層と混合して成膜した層との積層構造としても良い。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As a host of the light emitting layer of the organic EL device of the present embodiment, a hole transporting host material or an electron transporting host material can be used. In addition to the compound having a carbazole ring structure represented by the general formula (HOST-B) or the arylamine compound represented by the general formula (1) of the present embodiment as the hole transporting host material, 4 It is possible to use carbazole derivatives such as 4,4'-di (N-carbazolyl) biphenyl (CBP), TCTA, mCP and the like. As the electron transporting host material, p-bis (triphenylsilyl) benzene (UGH2) or 2, in addition to the compound having a nitrogen-containing heteroaromatic ring structure represented by the above general formula (HOST-A) 2 ′, 2 ′ ′-(1,3,5-phenylene) -tris (1-phenyl-1H-benzimidazole) (TPBi) can be used. Although these may be formed separately, they may be used as a single layer formed by mixing a plurality of materials, layers formed independently, layers formed by mixing, or each other A stacked structure of a layer formed separately and a layer formed by mixing may be employed. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　本実施形態では、電子輸送能を有した第１ホスト化合物と、正孔輸送能を有した第２ホスト化合物の二種類以上の化合物を用いるのが好ましい。前記第２ホスト化合物は、１種または２種以上が用いられてもよい。前記第１ホスト化合物と前記第２ホスト化合物とは、例えば、１：１０～１０：１の重量比で含まれてもよい。 In the present embodiment, it is preferable to use two or more compounds of a first host compound having an electron transporting ability and a second host compound having a hole transporting ability. One or two or more species of the second host compound may be used. The first host compound and the second host compound may be contained, for example, in a weight ratio of 1:10 to 10: 1.
　本実施形態の有機ＥＬ素子の発光層の前記第１ホスト化合物としては、前記一般式（ＨＯＳＴ－Ａ）で表される含窒素ヘテロ芳香族環構造を有する化合物が好ましく、前記第２ホスト化合物としては、前記一般式（ＨＯＳＴ－Ｂ）で表されるカルバゾール環構造を有する化合物または本実施形態の一般式（１）で表されるアリールアミン化合物が好ましい。 As the first host compound of the light emitting layer of the organic EL device of the present embodiment, a compound having a nitrogen-containing heteroaromatic ring structure represented by the general formula (HOST-A) is preferable, and as the second host compound The compound is preferably a compound having a carbazole ring structure represented by the general formula (HOST-B) or an arylamine compound represented by the general formula (1) of the present embodiment.
　前述した第１ホスト化合物および第２ホスト化合物以外に１種以上のホスト化合物をさらに含むことができる。 In addition to the first host compound and the second host compound described above, one or more host compounds can be further included.
　本実施形態の有機ＥＬ素子の燐光性発光材料として、本実施形態の一般式（３）で表されるイリジウム錯体がより好ましいが、その他に、Ｐｔ、Ｏｓ、Ｔｉ、Ｚｒ、Ｈｆ、Ｅｕ、Ｔｂ、Ｔｍ、Ｆｅ、Ｃｏ、Ｎｉ、Ｒｕ、Ｒｈ、Ｐｄまたはこれらの組み合わせを含む有機金属化合物を使用することができる。前記ドーパントは、赤色、緑色または青色のドーパントであってもよく、高性能の有機ＥＬ素子を作製することができる。 The iridium complex represented by the general formula (3) of this embodiment is more preferable as the phosphorescent light emitting material of the organic EL element of this embodiment, but in addition, Pt, Os, Ti, Zr, Hf, Eu, Tb Organometallic compounds comprising Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof can be used. The dopant may be a red, green or blue dopant, and a high performance organic EL device can be produced.
　燐光性発光材料のホスト材料へのドープは濃度消光を避けるため、発光層全体に対して1～３０重量パーセントの範囲で、共蒸着によってドープすることが好ましい。 It is preferable to dope the host material with the phosphorescent light emitting material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light emitting layer in order to avoid concentration quenching.
　これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　本実施形態の有機ＥＬ素子の正孔阻止層として、前記一般式（４）、（６）で表されるベンゾアゾール化合物、ピリミジン化合物がより好ましいが、その他に、バソクプロイン（以後、ＢＣＰと略称する）などのフェナントロリン誘導体や、ＢＡｌｑなどのキノリノール誘導体の金属錯体のほか、各種の希土類錯体、オキサゾール誘導体、トリアゾール誘導体、トリアジン誘導体など、正孔阻止作用を有する化合物を用いることができ、電子輸送層の材料を兼ねてもよい。これらは、単独で成膜しても良いが、他の材料とともに混合して成膜した単層として使用しても良く、上記複数の材料を単独で成膜した層同士、上記複数の材料を混合して成膜した層同士、または上記複数の材料を単独で成膜した層と混合して成膜した層との積層構造としても良い。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the hole blocking layer of the organic EL device of the present embodiment, the benzoazole compounds and pyrimidine compounds represented by the general formulas (4) and (6) are more preferable, but in addition, vasocuproin (hereinafter abbreviated as BCP) In addition to phenanthroline derivatives such as) and metal complexes of quinolinol derivatives such as BAlq, various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and other compounds having a hole blocking function can be used. It may double as a material. Although these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed by independently forming the above-mentioned plurality of materials, and the above-mentioned plurality of materials. A stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a plurality of the above materials alone may be employed. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　本実施形態の有機ＥＬ素子の電子輸送層として、前記一般式（４）、（６）で表されるベンゾアゾール化合物、ピリミジン化合物がより好ましいが、その他に、Ａｌｑ３、ＢＡｌｑ、後述する化合物（ＥＴＭ－１）をはじめとするキノリノール誘導体の金属錯体のほか、各種金属錯体、トリアゾール誘導体、トリアジン誘導体、オキサジアゾール誘導体、ピリジン誘導体、ベンズイミダゾール誘導体、チアジアゾール誘導体、アントラセン誘導体、カルボジイミド誘導体、キノキサリン誘導体、ピリドインドール誘導体、フェナントロリン誘導体、シロール誘導体なども用いることができる。これらは、単独で成膜しても良いが、他の材料とともに混合して成膜した単層として使用しても良く、上記複数の材料を単独で成膜した層同士、上記複数の材料を混合して成膜した層同士、または上記複数の材料を単独で成膜した層と混合して成膜した層との積層構造としても良い。これらの材料は蒸着法の他、スピンコート法やインクジェット法などの公知の方法によって薄膜形成を行うことができる。 As the electron transport layer of the organic EL device of the present embodiment, benzoazole compounds and pyrimidine compounds represented by the above general formulas (4) and (6) are more preferable, but in addition, Alq 3 , BAlq, compounds to be described later Other metal complexes of quinolinol derivatives including ETM-1), various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, Pyridoindole derivatives, phenanthroline derivatives, silole derivatives and the like can also be used. Although these may be formed separately, they may be used as a single layer formed by mixing with other materials, layers formed by independently forming the above-mentioned plurality of materials, and the above-mentioned plurality of materials. A stacked structure of layers formed by mixing and forming a film or layers formed by mixing and forming a plurality of the above materials alone may be employed. These materials can be formed into a thin film by a known method such as a spin coat method or an ink jet method other than the vapor deposition method.
　本実施形態の有機ＥＬ素子の電子注入層として、フッ化リチウム、フッ化セシウムなどのアルカリ金属塩、フッ化マグネシウムなどのアルカリ土類金属塩、リチウムキノリノールなどのキノリノール誘導体の金属錯体、酸化アルミニウムなどの金属酸化物などを用いることができるが、電子輸送層と陰極の好ましい選択においては、これを省略することができる。 As the electron injection layer of the organic EL device of this embodiment, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, aluminum oxide and the like Metal oxides of the above can be used, but this can be omitted in the preferred selection of the electron transport layer and the cathode.
　さらに、電子注入層あるいは電子輸送層において、該層に通常使用される有機化合物に対し、さらにセシウムやフッ化リチウム、及びイッテルビウムなどの金属をＮドーピングしたものを用いることができる。 Furthermore, in the electron injection layer or the electron transport layer, organic compounds commonly used in the layer may be further N-doped with a metal such as cesium, lithium fluoride and ytterbium.
　本実施形態の有機ＥＬ素子の陰極として、アルミニウム、イッテルビウムのような仕事関数の低い電極材料や、マグネシウム銀合金、マグネシウムインジウム合金、アルミニウムマグネシウム合金のような、より仕事関数の低い合金が電極材料として用いられる。 As a cathode of the organic EL element of the present embodiment, an electrode material having a low work function such as aluminum or ytterbium, or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy as an electrode material Used.
　以下、本発明の実施の形態について、実施例により具体的に説明するが、本発明はその要旨を越えない限り、以下の実施例に限定されるものではない。 EXAMPLES Hereinafter, the embodiments of the present invention will be specifically described by way of examples. However, the present invention is not limited to the following examples as long as the gist of the present invention is not exceeded.
＜ジ（ビフェニル－４－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－１）の合成＞
　窒素置換した反応容器に、ジ（ビフェニル－４－イル）－アミン：５０．０ｇ、５’－ブロモ－１，１’：３’，１’’ターフェニル：５７．７ｇ、ｔ－ブトキシナトリウム：５９．８ｇ、トルエン：１０００ｍＬを加え、３０分間超音波を照射しながら窒素ガスを通気した。酢酸パラジウム：１．４ｇ、ｔ－ブチルホスフィンの５０％（ｗ／ｖ）トルエン溶液：２．５ｍＬを加えて加熱還流下にて４時間撹拌した。放冷した後、ＥｔＯＡｃ、Ｈ２Ｏを加えて、分液操作にて有機層を抽出し、減圧下で濃縮して粗製物を得た。粗製物にトルエン／アセトン混合溶媒を加えて析出した固体を採取し、ジ（ビフェニル－４－イル）－（１，１’：３’，１’’－ターフェニル－５’－イル）－アミンの白色粉体：７３．９ｇ（収率８６％）を得た。 Synthesis of Di (biphenyl-4-yl)-(2′-phenyl-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine (Compound 1-1)>
In a nitrogen-substituted reaction vessel, 50.0 g of di (biphenyl-4-yl) -amine, 57.7 g of 5'-bromo-1,1 ': 3', 1 '' terphenyl, 57.7 g of sodium t-butoxy: 59.8 g and toluene: 1000 mL were added, and nitrogen gas was bubbled while being irradiated with ultrasonic waves for 30 minutes. Palladium acetate: 1.4 g, 50% (w / v) solution of t-butyl phosphine in toluene: 2.5 mL was added and the mixture was stirred for 4 hours while heating under reflux. After cooling, EtOAc and H 2 O were added, and the organic layer was extracted by liquid separation operation and concentrated under reduced pressure to obtain a crude product. Toluene / acetone mixed solvent is added to the crude product, and the precipitated solid is collected, and di (biphenyl-4-yl)-(1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine White powder of: 73.9 g (yield 86%) was obtained.
　ジ（ビフェニル－４－イル）－（１，１’：３’，１’’－ターフェニル－５’－イル）－アミン：６２．３ｇ、ジクロロメタン：１２５０ｍＬを窒素置換した反応容器に加え、氷浴にて冷却した。Ｎ－ブロモスクシンイミド：２０．２ｇを添加して、８時間撹拌した。反応液を減圧下で濃縮した後、メタノールを加えて析出した固体を採取し、（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－ジ（ビフェニル－４－イル）－アミンの白色固体：６０．０ｇ（収率８４％）を得た。 Di (biphenyl-4-yl)-(1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine: 62.3 g, dichloromethane: 1250 mL was added to a nitrogen-substituted reaction vessel, and ice was added. It cooled with the bath. N-bromosuccinimide: 20.2 g was added and stirred for 8 hours. The reaction solution is concentrated under reduced pressure, methanol is added, and the precipitated solid is collected, and (2'-bromo-1,1 ': 3', 1 ''-terphenyl-5'-yl) -di (di) White solid of biphenyl-4-yl) -amine: 60.0 g (yield 84%) was obtained.
　窒素置換した反応容器に、（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－ジ（ビフェニル－４－イル）－アミン：１０．０ｇ、トルエン：８０ｍＬ、エタノール：４０ｍＬ、フェニルボロン酸：２．３ｇ、続いて、予め炭酸カリウム：６．６ｇをＨ２Ｏ：３０ｍＬに溶解した水溶液を加えて３０分間超音波を照射しながら窒素ガスを通気した。テトラキストリフェニルホスフィンパラジウム：０．４ｇを加えて加熱還流下にて２４時間撹拌した。放冷した後、ＥｔＯＡｃ、Ｈ２Ｏを加えて、分液操作にて有機層を抽出し、減圧下で濃縮して粗製物を得た。粗製物にトルエンを加えて析出した固体を採取し、ジ（ビフェニル－４－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－１）の白色粉体：４．０ｇ（収率４０％）を得た。 (2'-Bromo-1,1 ': 3', 1 ''-terphenyl-5'-yl) -di (biphenyl-4-yl) -amine: 10.0 g, toluene in a nitrogen-substituted reaction vessel 80 mL, ethanol: 40 mL, phenylboronic acid: 2.3 g, followed by the addition of an aqueous solution of potassium carbonate: 6.6 g previously dissolved in 30 mL of H 2 O and bubbling nitrogen gas while irradiating ultrasonic waves for 30 minutes did. Tetrakistriphenylphosphine palladium: 0.4 g was added, and the mixture was stirred for 24 hours while heating under reflux. After cooling, EtOAc and H 2 O were added, and the organic layer was extracted by liquid separation operation and concentrated under reduced pressure to obtain a crude product. Toluene is added to the crude product and the precipitated solid is collected, and di (biphenyl-4-yl)-(2'-phenyl-1,1 ': 3', 1 ''-terphenyl-5'-yl)- White powder of amine (compound 1-1): 4.0 g (yield 40%) was obtained.
Figure JPOXMLDOC01-appb-C000072
Figure JPOXMLDOC01-appb-C000072
　得られた白色粉体についてＮＭＲを使用して構造を同定した。
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）で以下の３５個の水素のシグナルを検出した。
δ（ｐｐｍ）＝７．６０（７Ｈ）、７．４６（４Ｈ）、７．４１－７．３０（６Ｈ）、７．２８（２Ｈ）、７．１８－６．８６（１３Ｈ）、６．８９（３Ｈ）。 The structure of the resulting white powder was identified using NMR.
The following 35 hydrogen signals were detected by 1 H-NMR (CDCl 3 ).
δ (ppm) = 7.60 (7H), 7.46 (4H), 7.41-7.30 (6H), 7.28 (2H), 7.18-6.86 (13H), 6. 89 (3H).
＜（ビフェニル－４－イル）－（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－２）の合成＞
　実施例１と同様の手法で合成した、（ビフェニル－４－イル）－（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－アミン：１７．６ｇに、トルエン：１７０ｍＬ、エタノール：３５ｍＬ、フェニルボロン酸：３．７ｇ、続いて、予め炭酸カリウム：４．４ｇをＨ２Ｏ：３０ｍＬに溶解した水溶液を加えて３０分間超音波を照射しながら窒素ガスを通気した。テトラキストリフェニルホスフィンパラジウム：０．６ｇを加えて加熱還流下にて２４時間撹拌した。放冷した後、分液操作によって有機層を採取した。水および飽和食塩水を用いて洗浄を行い、無水硫酸マグネシウムを用いて乾燥し、減圧下で濃縮して粗製物を得た。粗製物をトルエン／ｎ－ヘプタン混合溶媒を用いて、カラムクロマトグラフィーによる精製を行うことによって、（ビフェニル－４－イル）－（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－２）の白色粉体：１１．２ｇ（収率６４％）を得た。 <(Biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)-(2'-phenyl-1,1 ': 3', 1 ''-terphenyl-5'-yl Synthesis of) -amine (compound 1-2)>
(Biphenyl-4-yl)-(2′-bromo-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl)-(9,9) synthesized in the same manner as in Example 1. -Dimethyl-9H-fluoren-2-yl) -amine: To 17.6 g, toluene: 170 mL, ethanol: 35 mL, phenylboronic acid: 3.7 g, followed by potassium carbonate: 4.4 g of H 2 O: An aqueous solution dissolved in 30 mL was added and nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. 0.6 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 24 hours while heating under reflux. After allowing to cool, the organic layer was collected by liquid separation operation. The residue was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product. The crude product is purified by column chromatography using a toluene / n-heptane mixed solvent to give (biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)-(2 11.2 g (yield 64%) of white powder of '-phenyl-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine (compound 1-2) was obtained.
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-C000073
　得られた白色粉体についてＮＭＲを使用して構造を同定した。
　１Ｈ－ＮＭＲ（ＣＤＣｌ３）で以下の３９個の水素のシグナルを検出した。
δ（ｐｐｍ）＝７．５３－７．６９（５Ｈ）、７．２１－７．４８（１４Ｈ）、６．９６－７．１２（１２Ｈ）、６．８１－６．９０（２Ｈ）、１．５１（６Ｈ）。 The structure of the resulting white powder was identified using NMR.
The following 39 hydrogen signals were detected by 1 H-NMR (CDCl 3 ).
δ (ppm) = 7.53-7.69 (5 H), 7.21-7. 48 (14 H), 6.96-7.12 (12 H), 6.81-6.90 (2 H), 1 .51 (6H).
＜ジ（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－３）の合成＞
　実施例１と同様の手法で合成した、（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－ジ（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－アミン：１０．０ｇに、トルエン：８０ｍＬ、エタノール：４０ｍＬ、フェニルボロン酸：２．１ｇ、続いて、予め炭酸カリウム：５．９ｇをＨ２Ｏ：３０ｍＬに溶解した水溶液を加えて３０分間超音波を照射しながら窒素ガスを通気した。テトラキストリフェニルホスフィンパラジウム：０．３ｇを加えて加熱還流下にて５時間撹拌した。放冷した後、ＥｔＯＡｃ、Ｈ２Ｏを加えて、分液操作にて有機層を抽出し、減圧下で濃縮して粗製物を得た。粗製物にＴＨＦ／アセトン混合溶媒を加えて析出した固体を採取し、ジ（９，９－ジメチル－９Ｈ－フルオレン－２－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－３）の白色粉体：７．７ｇ（収率７７％）を得た。 <Di (9,9-dimethyl-9H-fluoren-2-yl)-(2′-phenyl-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine (compound 1- 3) Synthesis>
(2′-Bromo-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -di (9,9-dimethyl-9H-fluorene) synthesized in the same manner as in Example 1. 2-yl) -amine: To 10.0 g, toluene: 80 mL, ethanol: 40 mL, phenylboronic acid: 2.1 g, followed by an aqueous solution previously dissolving 5.9 g of potassium carbonate in 30 mL of H 2 O Nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. 0.3 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 5 hours while heating under reflux. After cooling, EtOAc and H 2 O were added, and the organic layer was extracted by liquid separation operation and concentrated under reduced pressure to obtain a crude product. The crude product is mixed with THF / acetone mixed solvent, and the precipitated solid is collected, and di (9,9-dimethyl-9H-fluoren-2-yl)-(2'-phenyl-1,1 ': 3', 1 White powder of '′ -terphenyl-5′-yl) -amine (compound 1-3): 7.7 g (yield 77%) was obtained.
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000074
　得られた白色粉体についてＮＭＲを使用して構造を同定した。
　１Ｈ－ＮＭＲ（ＤＭＳＯ－ｄ６）で以下の４３個の水素のシグナルを検出した。
δ（ｐｐｍ）＝７．８１（２Ｈ）、７．７６（２Ｈ）、７．５３（４Ｈ）、７．３１（４Ｈ）、７．１８（２Ｈ）、７．０８（６Ｈ）、７．０３－６．９２（９Ｈ）、６．８３（２Ｈ）、１．４４（１２Ｈ）。 The structure of the resulting white powder was identified using NMR.
The following 43 hydrogen signals were detected by 1 H-NMR (DMSO-d 6 ).
δ (ppm) = 7.81 (2H), 7.76 (2H), 7.53 (4H), 7.31 (4H), 7.18 (2H), 7.08 (6H), 7.03 -6.92 (9 H), 6.83 (2 H), 1.44 (12 H).
＜（ビフェニル－４－イル）－（９，９－ジフェニル－９Ｈ－フルオレン－２－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－４）の合成＞
　実施例１と同様の手法で合成した、（ビフェニル－４－イル）－（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－（９，９－ジフェニル－９Ｈ－フルオレン－２－イル）－アミン：１４．０ｇに、トルエン：１４０ｍＬ、エタノール：３５ｍＬ、フェニルボロン酸：３．２ｇ、続いて、予め炭酸カリウム：４．９ｇをＨ２Ｏ：３５ｍＬに溶解した水溶液を加えて３０分間超音波を照射しながら窒素ガスを通気した。テトラキストリフェニルホスフィンパラジウム：０．４ｇを加えて加熱還流下にて２０時間撹拌した。放冷した後、ＥｔＯＡｃ、Ｈ２Ｏを加えて、分液操作にて有機層を抽出し、減圧下で濃縮して粗製物を得た。粗製物にトルエン／アセトン混合溶媒を加えて析出した固体を採取し、（ビフェニル－４－イル）－（９，９－ジフェニル－９Ｈ－フルオレン－２－イル）－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－４）の白色粉体：７．５ｇ（収率５４％）を得た。 <(Biphenyl-4-yl)-(9,9-diphenyl-9H-fluoren-2-yl)-(2'-phenyl-1,1 ': 3', 1 ''-terphenyl-5'-yl Synthesis of))-Amine (Compound 1-4)>
(Biphenyl-4-yl)-(2′-bromo-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl)-(9,9) synthesized in the same manner as in Example 1. -Diphenyl-9H-fluoren-2-yl) -amine: 14.0 g, toluene: 140 mL, ethanol: 35 mL, phenylboronic acid: 3.2 g, followed by potassium carbonate: 4.9 g in advance: H 2 O: An aqueous solution dissolved in 35 mL was added and nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.4 g was added, and the mixture was stirred for 20 hours while heating under reflux. After cooling, EtOAc and H 2 O were added, and the organic layer was extracted by liquid separation operation and concentrated under reduced pressure to obtain a crude product. Toluene / acetone mixed solvent is added to the crude product, and the precipitated solid is collected, and (biphenyl-4-yl)-(9,9-diphenyl-9H-fluoren-2-yl)-(2'-phenyl-1, White powder of 1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine (compound 1-4): 7.5 g (yield 54%) was obtained.
Figure JPOXMLDOC01-appb-C000075
Figure JPOXMLDOC01-appb-C000075
　得られた白色粉体についてＮＭＲを使用して構造を同定した。
　１Ｈ－ＮＭＲ（ＤＭＳＯ－ｄ６）で以下の４３個の水素のシグナルを検出した。
δ（ｐｐｍ）＝７．９１（１Ｈ）、７．８７（１Ｈ）、７．６５（４Ｈ）、７．４９－７．０４（２６Ｈ）、６．９９（３Ｈ）、６．９４（２Ｈ）、６．９０（４Ｈ）、６．７９（２Ｈ）。 The structure of the resulting white powder was identified using NMR.
The following 43 hydrogen signals were detected by 1 H-NMR (DMSO-d 6 ).
δ (ppm) = 7.91 (1 H), 7.87 (1 H), 7.65 (4 H), 7.49-7.04 (26 H), 6.99 (3 H), 6.94 (2 H) , 6.90 (4H), 6.79 (2H).
＜（ビフェニル－４－イル）－｛４－（ナフチル－２－イル）－フェニル）｝－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－５８）の合成＞
　実施例１と同様の手法で合成した、（ビフェニル－４－イル）－（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－｛４－（ナフチル－２－イル）－フェニル）｝－アミン：１０．０ｇに、トルエン：７０ｍＬ、エタノール：３０ｍＬ、フェニルボロン酸：２．７ｇ、続いて、予め炭酸カリウム：６．１ｇをＨ２Ｏ：２０ｍＬに溶解した水溶液を加えて３０分間超音波を照射しながら窒素ガスを通気した。テトラキストリフェニルホスフィンパラジウム：０．３ｇを加えて加熱還流下にて２４時間撹拌した。放冷した後、メタノールを加えて析出した固体を採取して粗製物を得た。粗製物にＴＨＦ／アセトン混合溶媒を加えて析出した固体を採取し、（ビフェニル－４－イル）－（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－｛４－（ナフチル－２－イル）－フェニル）｝－アミン（化合物１－５８）の白色粉体：６．５ｇ（収率６５％）を得た。 <(Biphenyl-4-yl)-{4- (naphthyl-2-yl) -phenyl)}-(2′-phenyl-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -Synthesis of amine (compound 1-58)>
(Biphenyl-4-yl)-(2′-bromo-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl)-{4- () synthesized in the same manner as in Example 1. Naphthyl-2-yl) -phenyl)}-amine: 10.0 g, toluene: 70 mL, ethanol: 30 mL, phenylboronic acid: 2.7 g, followed by potassium carbonate: 6.1 g H 2 O: 20 mL The aqueous solution dissolved in was added, and nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. 0.3 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 24 hours while heating under reflux. After allowing to cool, methanol was added and the precipitated solid was collected to obtain a crude product. The crude product is mixed with THF / acetone mixed solvent, and the precipitated solid is collected, and (biphenyl-4-yl)-(2′-bromo-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′- 6.5 g (yield: 65%) of white powder of (yl)-{4- (naphthyl-2-yl) -phenyl)}-amine (compound 1-58) was obtained.
Figure JPOXMLDOC01-appb-C000076
Figure JPOXMLDOC01-appb-C000076
　得られた白色粉体についてＮＭＲを使用して構造を同定した。
　１Ｈ－ＮＭＲ（ＤＭＳＯ－ｄ６）で以下の３７個の水素のシグナルを検出した。
δ（ｐｐｍ）＝８．２１（１Ｈ）、７．９６（３Ｈ）、７．８６（３Ｈ）、７．７０（４Ｈ）７．５２（２Ｈ）、７．４５（２Ｈ）、７．３５（５Ｈ）、７．１９－６．９６（１５Ｈ）、６．８６（２Ｈ）。 The structure of the resulting white powder was identified using NMR.
The following 37 hydrogen signals were detected by 1 H-NMR (DMSO-d 6 ).
δ (ppm) = 8.21 (1 H), 7.96 (3 H), 7.86 (3 H), 7.70 (4 H) 7.52 (2 H), 7.45 (2 H), 7.35 ( 5H), 7.19-6.96 (15H), 6.86 (2H).
＜ジ｛４－（ナフチル－２－イル）－フェニル）｝－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－６２）の合成＞
　実施例１と同様の手法で合成した、（２’－ブロモ－１，１’：３’，１’’－ターフェニル－５’－イル）－ジ｛４－（ナフチル－２－イル）－フェニル）｝－アミン：１５．０ｇに、トルエン：１６０ｍＬ、エタノール：４０ｍＬ、フェニルボロン酸：３．０ｇ、続いて、予め炭酸カリウム：５．７ｇをＨ２Ｏ：４０ｍＬに溶解した水溶液を加えて３０分間超音波を照射しながら窒素ガスを通気した。テトラキストリフェニルホスフィンパラジウム：０．５ｇを加えて加熱還流下にて２１時間撹拌した。放冷した後、分液操作によって有機層を採取した。水および飽和食塩水を用いて洗浄を行い、無水硫酸マグネシウムを用いて乾燥し、減圧下で濃縮して粗製物を得た。粗製物にトルエン／ｎ－ヘプタン混合溶媒を加えて析出した固体を採取し、ジ｛４－（ナフチル－２－イル）－フェニル）｝－（２’－フェニル－１，１’：３’，１’’－ターフェニル－５’－イル）－アミン（化合物１－６２）の白色粉体：８．２ｇ（収率５５％）を得た。 <Di {4- (naphthyl-2-yl) -phenyl)}-(2′-phenyl-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -amine (compound 1-62) Synthesis of
(2′-Bromo-1,1 ′: 3 ′, 1 ′ ′-terphenyl-5′-yl) -di {4- (naphthyl-2-yl)-synthesized in the same manner as in Example 1. Phenyl)}-amine: To 15.0 g of toluene: 160 mL, ethanol: 40 mL, phenylboronic acid: 3.0 g, followed by an aqueous solution previously dissolving 5.7 g of potassium carbonate in 40 mL of H 2 O Nitrogen gas was bubbled while irradiating ultrasonic waves for 30 minutes. 0.5 g of tetrakistriphenylphosphine palladium was added, and the mixture was stirred for 21 hours while heating under reflux. After allowing to cool, the organic layer was collected by liquid separation operation. The residue was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product. The crude product is mixed with a mixed solvent of toluene and n-heptane, and the precipitated solid is collected, and di {4- (naphthyl-2-yl) -phenyl)}-(2'-phenyl-1,1 ': 3', White powder of 1 ′ ′-terphenyl-5′-yl) -amine (compound 1-62): 8.2 g (yield 55%) was obtained.
Figure JPOXMLDOC01-appb-C000077
Figure JPOXMLDOC01-appb-C000077
　得られた白色粉体についてＮＭＲを使用して構造を同定した。
　１Ｈ－ＮＭＲ（ＤＭＳＯ－ｄ６）で以下の３９個の水素のシグナルを検出した。
δ（ｐｐｍ）＝８．２２（２Ｈ）、８．０３－７．９０（６Ｈ）、７．８６（６Ｈ）、７．５３（４Ｈ）７．３９（４Ｈ）、７．１９－６．９８（１５Ｈ）、６．８７（２Ｈ）。 The structure of the resulting white powder was identified using NMR.
The following 39 hydrogen signals were detected by 1 H-NMR (DMSO-d 6 ).
δ (ppm) = 8.22 (2H), 8.03-7.90 (6H), 7.86 (6H), 7.53 (4H) 7.39 (4H), 7.19-6.98 (15 H), 6.87 (2 H).
　一般式（１）で表されるアリールアミン化合物について、高感度示差走査熱量計（ブルカー・エイエックスエス製、ＤＳＣ３１００Ｓ）によってガラス転移点を求めた。
　　　　　　　　　　　　　　　　ガラス転移点　
実施例１の化合物　　　　　　　　１１０℃
実施例２の化合物　　　　　　　　１２１℃
実施例３の化合物　　　　　　　　１３５℃
実施例４の化合物　　　　　　　　１４０℃
実施例５の化合物　　　　　　　　１１５℃
実施例６の化合物　　　　　　　　１２１℃ The glass transition point of the arylamine compound represented by the general formula (1) was determined by a high sensitivity differential scanning calorimeter (DSC3100S, manufactured by Bruker AXS).
Glass transition point
Compound of Example 1 110 ° C.
Compound of Example 2 121 ° C.
Compound of Example 3 135 ° C.
Compound of Example 4 140 ° C.
Compound of Example 5: 115 ° C.
Compound of Example 6 121 ° C.
　一般式（１）で表されるアリールアミン化合物は１００℃以上のガラス転移点を有しており、薄膜状態が安定であることを示すものである。 The arylamine compound represented by the general formula (1) has a glass transition point of 100 ° C. or more, which indicates that the thin film state is stable.
　実施例１～実施例６の化合物を用いて、ＩＴＯ基板の上に膜厚１００ｎｍの蒸着膜を作製して、イオン化ポテンシャル測定装置（住友重機械工業株式会社製、ＰＹＳ－２０２型）で仕事関数を測定した。
　　　　　　　　　　　　　仕事関数
実施例１の化合物　　　　　５．７１ｅＶ
実施例２の化合物　　　　　５．６２ｅＶ
実施例３の化合物　　　　　５．５８ｅＶ
実施例４の化合物　　　　　５．６９ｅＶ
実施例５の化合物　　　　　５．７０ｅＶ
実施例６の化合物　　　　　５．６９ｅＶ Using the compounds of Examples 1 to 6, deposited films of 100 nm in thickness are prepared on an ITO substrate, and work function is measured with an ionization potential measuring device (PYS-202 type, manufactured by Sumitomo Heavy Industries, Ltd.). Was measured.
Compound of Work Function Example 1 5.71 eV
Compound of Example 2 5.62 eV
Compound of Example 3 5.58 eV
Compound of Example 4 5.69 eV
Compound of Example 5 5.70 eV
Compound of Example 6 5.69 eV
　このように実施例１～実施例６の化合物はＮＰＤ、ＴＰＤなどの一般的な正孔輸送材料がもつ仕事関数５．４ｅＶと比較して、好適なエネルギー準位を示しており、良好な正孔輸送能力を有していることが分かる。 Thus, the compounds of Examples 1 to 6 show favorable energy levels as compared with the work function 5.4 eV of common hole transport materials such as NPD, TPD, etc. It can be seen that it has a hole transport capacity.
　実施例１～実施例４の化合物について、１．０×１０－５ｍｏｌ／Ｌの２－メチルテトラヒドロフラン溶液を調製した。調製した溶液を専用の石英管に入れ、純窒素を通気することによって酸素分を除き、更に酸素分が混入しないようにセプタムラバーによる栓をした。７７Ｋに冷却した後、蛍光リン光分光光度計（日本分光株式会社製、ＦＰ－８５００型）を用い、励起光を照射して燐光スペクトルを測定した。燐光スペクトルの短波長側の第１ピークの波長を読み取り、該波長値を光のエネルギーに換算してＴ１を算出した。なお、下記には参考としてＨＴＭ－２および化合物（３－３）のＴ１も併記する。
　　　　　　　　　　　　　　　　　　　　Ｔ１
実施例１の化合物（１－１）　　　　　２．５５ｅＶ
実施例２の化合物（１－２）　　　　　２．５８ｅＶ
実施例３の化合物（１－３）　　　　　２．５８ｅＶ
実施例４の化合物（１－４）　　　　　２．５７ｅＶ
ＨＴＭ－２　　　　　　　　　　　　　２．４０ｅＶ
化合物３－３　　　　　　　　　　　　２．４３ｅＶ For the compounds of Examples 1 to 4, a solution of 1.0 × 10 −5 mol / L of 2-methyltetrahydrofuran was prepared. The prepared solution was placed in a dedicated quartz tube, oxygen was removed by bubbling with pure nitrogen, and stoppered with septamuraber to prevent further mixing of oxygen. After cooling to 77 K, the phosphorescence spectrum was measured by irradiating excitation light using a fluorescent phosphorescence spectrophotometer (FP-8500 manufactured by JASCO Corp.). The wavelength of the first peak on the short wavelength side of the phosphorescence spectrum was read, and the wavelength value was converted to light energy to calculate T1. In the following, HTM-2 and T1 of compound (3-3) are also described as a reference.
T1
Compound (1-1) of Example 1 2.55 eV
Compound (1-2) of Example 2 2.58 eV
Compound (1-3) of Example 3 2.58 eV
Compound (1-4) of Example 4 2.57 eV
HTM-2 2.40 eV
Compound 3-3 2.43 eV
Figure JPOXMLDOC01-appb-C000078
Figure JPOXMLDOC01-appb-C000078
Figure JPOXMLDOC01-appb-C000079
Figure JPOXMLDOC01-appb-C000079
Figure JPOXMLDOC01-appb-C000080
Figure JPOXMLDOC01-appb-C000080
Figure JPOXMLDOC01-appb-C000081
Figure JPOXMLDOC01-appb-C000081
Figure JPOXMLDOC01-appb-C000082
Figure JPOXMLDOC01-appb-C000082
Figure JPOXMLDOC01-appb-C000083
Figure JPOXMLDOC01-appb-C000083
　このように本開示で用いられる化合物は一般的に用いられる正孔輸送材料であるトリ（ｍ－ターフェニル－４－イル）アミン（ＨＴＭ－２）がもつＴ１より大きい値を有している。トリアリールアミンの窒素原子に対してメタ位に置換された二つのフェニル基によってアミン周辺の骨格に大きなねじれが生じ、さらに窒素原子に対してパラ位に置換されたフェニル基が大きな立体障害基として作用することで、本開示で用いられる化合物はＨＴＭ－２に比べて高いＴ１を実現している。また本開示で用いられる化合物は緑色燐光性発光材料であるトリス（４-メチル-２,５-ジフェニルピリジン）イリジウム（III）（化合物３－３）がもつＴ１より大きい値を有しており、発光層で励起された三重項励起子を充分閉じ込める能力を有している。 Thus, the compound used in the present disclosure has a value larger than T1 of tri (m-terphenyl-4-yl) amine (HTM-2) which is a commonly used hole transport material. The two phenyl groups substituted in the meta position to the nitrogen atom of the triarylamine cause a large twist in the backbone around the amine, and the phenyl group substituted in the para position to the nitrogen atom as a large sterically hindered group By acting, the compounds used in the present disclosure achieve higher T1 than HTM-2. In addition, the compound used in the present disclosure has a value larger than T1 possessed by tris (4-methyl-2,5-diphenylpyridine) iridium (III) (compound 3-3) which is a green phosphorescent light-emitting material, It has the ability to sufficiently confine triplet excitons excited in the light emitting layer.
　有機ＥＬ素子は、図１に示すように、ガラス基板１上に透明陽極２としてＩＴＯ電極をあらかじめ形成したものの上に、正孔注入層３、第一正孔輸送層４、第二正孔輸送層５、発光層６、電子輸送層７、電子注入層８、および陰極（アルミニウム電極）９を、この順に蒸着して作製した。 As shown in FIG. 1, the organic EL device has a hole injection layer 3, a first hole transport layer 4, and a second hole transport on a glass substrate 1 on which an ITO electrode is formed in advance as a transparent anode 2. The layer 5, the light emitting layer 6, the electron transport layer 7, the electron injection layer 8, and the cathode (aluminum electrode) 9 were produced by vapor deposition in this order.
　具体的には、膜厚１５０ｎｍのＩＴＯを成膜したガラス基板１をイソプロピルアルコール中にて超音波洗浄を２０分間行った後、２００℃に加熱したホットプレート上にて１０分間乾燥を行った。その後、ＵＶオゾン処理を１５分間行った後、このＩＴＯ付きガラス基板を真空蒸着機内に取り付け、０．００１Ｐａ以下まで減圧した。続いて、透明陽極２を覆うように正孔注入層３として、下記構造式の化合物Acceptor－１と化合物（７－３）とを、蒸着速度比がAcceptor－１：化合物（７－３）＝３：９７となる蒸着速度で透明陽極２の上に二元蒸着し、膜厚が１０ｎｍとなるように正孔注入層３を形成した。この正孔注入層３の上に、第一正孔輸送層４として化合物（７－３）を膜厚が７０ｎｍとなるように蒸着した。この第一正孔輸送層４の上に、第二正孔輸送層５として実施例２の化合物（１－２）を膜厚が１０ｎｍとなるように蒸着した。この第二正孔輸送層５の上に、発光層６として前記第１ホスト化合物（Ａ－１９）と前記第２ホスト化合物（Ｂ－２２）とを同時にホストとして用い、ドーパントとして前記イリジウム化合物(３－３)を５ｗｔ％にドーピングして、膜厚４０ｎｍになるように化合物を真空蒸着した。ここで前記第１ホスト化合物（Ａ－１９）と前記第２ホスト化合物（Ｂ－２２）とは１：１の比率で用いた。 Specifically, the glass substrate 1 on which ITO having a film thickness of 150 nm was formed was subjected to ultrasonic cleaning for 20 minutes in isopropyl alcohol and then dried for 10 minutes on a hot plate heated to 200.degree. Thereafter, UV ozone treatment was carried out for 15 minutes, and then the ITO-attached glass substrate was mounted in a vacuum deposition machine, and the pressure was reduced to 0.001 Pa or less. Subsequently, a compound Acceptor-1 of the following structural formula and a compound (7-3) are formed as a hole injection layer 3 so as to cover the transparent anode 2, and the deposition rate ratio is Acceptor-1: Compound (7-3) = Binary vapor deposition was performed on the transparent anode 2 at a vapor deposition rate of 3:97, and the hole injection layer 3 was formed to have a film thickness of 10 nm. The compound (7-3) was vapor-deposited as the first hole transport layer 4 on the hole injection layer 3 to a film thickness of 70 nm. The compound (1-2) of Example 2 was vapor deposited as the second hole transport layer 5 on the first hole transport layer 4 so as to have a film thickness of 10 nm. On the second hole transport layer 5, the first host compound (A-19) and the second host compound (B-22) are simultaneously used as a light emitting layer 6 as a host, and the iridium compound (d The compound was vacuum deposited to a film thickness of 40 nm by doping 3-3 wt% to 5 wt%. Here, the first host compound (A-19) and the second host compound (B-22) were used at a ratio of 1: 1.
　次に、この発光層６の上に、電子輸送層７として下記構造式の化合物（４－７８）と下記構造式の化合物ＥＴＭ－１とを、蒸着速度比が化合物（４－７８）：ＥＴＭ－１＝５０：５０となる蒸着速度で二元蒸着し、膜厚が３０ｎｍとなるように電子輸送層６を形成した。この電子輸送層７の上に、電子注入層８としてフッ化リチウムを膜厚１ｎｍとなるように蒸着した。最後に、電子注入層８の上にアルミニウムを１００ｎｍの厚みとなるように蒸着して陰極９を形成した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Next, on the light emitting layer 6, the compound (4-78) having a deposition rate ratio of the compound (4-78): ETM is used as the electron transport layer 7 and the compound (4-78) of the following structural formula and the compound ETM-1 of the following structural formula. Binary vapor deposition was performed at a vapor deposition rate of -1 = 50: 50 to form an electron transport layer 6 so as to have a film thickness of 30 nm. Lithium fluoride was vapor-deposited as the electron injection layer 8 to a film thickness of 1 nm on the electron transport layer 7. Finally, aluminum was vapor deposited on the electron injection layer 8 to a thickness of 100 nm to form a cathode 9. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-C000085
Figure JPOXMLDOC01-appb-C000085
Figure JPOXMLDOC01-appb-C000086
Figure JPOXMLDOC01-appb-C000086
Figure JPOXMLDOC01-appb-C000087
Figure JPOXMLDOC01-appb-C000087
Figure JPOXMLDOC01-appb-C000088
Figure JPOXMLDOC01-appb-C000088
Figure JPOXMLDOC01-appb-C000089
Figure JPOXMLDOC01-appb-C000089
Figure JPOXMLDOC01-appb-C000090
Figure JPOXMLDOC01-appb-C000090
Figure JPOXMLDOC01-appb-C000091
Figure JPOXMLDOC01-appb-C000091
　実施例１０において、電子輸送層７の材料として化合物（４－７８）の代わりに化合物（６－１）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 10 except that the compound (6-1) was used instead of the compound (4-78) as the material of the electron transport layer 7. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
Figure JPOXMLDOC01-appb-C000092
Figure JPOXMLDOC01-appb-C000092
　実施例１０において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに実施例３の化合物（１－３）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Example 10 is the same as Example 10 except that the compound (1-3) of Example 3 is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5. Made. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
Figure JPOXMLDOC01-appb-C000093
Figure JPOXMLDOC01-appb-C000093
　実施例１２において、電子輸送層７の材料として化合物（４－７８）の代わりに化合物（６－１）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 12, except that the compound (6-1) was used instead of the compound (4-78) as the material of the electron transport layer 7. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１０において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに実施例４の化合物（１－４）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Example 10 is repeated except that the compound (1-4) of Example 4 is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5 Made. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
Figure JPOXMLDOC01-appb-C000094
Figure JPOXMLDOC01-appb-C000094
　実施例１４において、電子輸送層７の材料として化合物（４－７８）の代わりに化合物（６－１）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 14, except that the compound (6-1) was used instead of the compound (4-78) as the material of the electron transport layer 7. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１０において、第２ホスト材料として化合物（Ｂ－２２）の代わりに実施例２の化合物（１－２）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（１－２）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 10 except that the compound (1-2) of Example 2 was used instead of the compound (B-22) as the second host material. Here, the first host compound (A-19) and the second host compound (1-2) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１１において、第２ホスト材料として化合物（Ｂ－２２）の代わりに実施例２の化合物（１－２）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（１－２）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 11 except that the compound (1-2) of Example 2 was used instead of the compound (B-22) as the second host material. Here, the first host compound (A-19) and the second host compound (1-2) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１２において、第２ホスト材料として化合物（Ｂ－２２）の代わりに実施例３の化合物（１－３）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（１－３）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 12 except that the compound (1-3) of Example 3 was used instead of the compound (B-22) as the second host material. Here, the first host compound (A-19) and the second host compound (1-3) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１３において、第２ホスト材料として化合物（Ｂ－２２）の代わりに実施例３の化合物（１－３）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（１－３）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 13, except that the compound (1-3) of Example 3 was used instead of the compound (B-22) as the second host material. Here, the first host compound (A-19) and the second host compound (1-3) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１４において、第２ホスト材料として化合物（Ｂ－２２）の代わりに実施例４の化合物（１－４）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（１－４）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 14, except that the compound (1-4) of Example 4 was used instead of the compound (B-22) as the second host material. Here, the first host compound (A-19) and the second host compound (1-4) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１５において、第２ホスト材料として化合物（Ｂ－２２）の代わりに実施例４の化合物（１－４）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（１－４）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 An organic EL device was produced in the same manner as in Example 15 except that the compound (1-4) of Example 4 was used instead of the compound (B-22) as the second host material. Here, the first host compound (A-19) and the second host compound (1-4) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
［比較例１］
　比較のために、実施例１０において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに化合物（ＨＴＭ－２）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Comparative Example 1
For comparison, in the same manner as in Example 10, except that the compound (HTM-2) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, an organic EL device Was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
Figure JPOXMLDOC01-appb-C000095
Figure JPOXMLDOC01-appb-C000095
［比較例２］
　比較のために、実施例１１において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに化合物（ＨＴＭ－２）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Comparative Example 2
For comparison, in the same manner as in Example 11, except that the compound (HTM-2) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, an organic EL device was obtained. Was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
［比較例３］
　比較のために、実施例１０において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに下記構造式の化合物（Ｂ－２２）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Comparative Example 3
For comparison, in Example 10, a compound (B-22) of the following structural formula was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5. The organic EL device was manufactured. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
Figure JPOXMLDOC01-appb-C000096
Figure JPOXMLDOC01-appb-C000096
［比較例４］
　比較のために、実施例１１において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに化合物（Ｂ－２２）を用いた以外は同様にして有機ＥＬ素子を作製した。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Comparative Example 4
For comparison, in the same manner as in Example 11, except that the compound (B-22) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, an organic EL device was obtained. Was produced. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
［比較例５］
　比較のために、実施例１４において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに化合物（ＨＴＭ－２）を用い、第２ホスト材料として実施例２の化合物（１－２）の代わりに化合物（ＨＴＭ－２）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（ＨＴＭ－２）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Comparative Example 5
For comparison, in Example 14, the compound (HTM-2) is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, and Example 2 as the second host material. An organic EL device was produced in the same manner except that the compound (HTM-2) was used instead of the compound (1-2). Here, the first host compound (A-19) and the second host compound (HTM-2) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
［比較例６］
　比較のために、実施例１５において、第二正孔輸送層５の材料として実施例２の化合物（１－２）の代わりに化合物（ＨＴＭ－２）を用い、第２ホスト材料として実施例２の化合物（１－２）に代わりに化合物（ＨＴＭ－２）を用いた以外は同様にして有機ＥＬ素子を作製した。ここで第１ホスト化合物（Ａ－１９）と第２ホスト化合物（ＨＴＭ－２）とは１：１の比率で用いた。作製した有機ＥＬ素子について、大気中、常温で特性測定を行った。作製した有機ＥＬ素子に直流電圧を印加したときの発光特性の測定結果を表１にまとめて示した。 Comparative Example 6
For comparison, in Example 15, the compound (HTM-2) is used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5, and Example 2 as the second host material. An organic EL device was produced in the same manner except that the compound (HTM-2) was used instead of the compound (1-2). Here, the first host compound (A-19) and the second host compound (HTM-2) were used at a ratio of 1: 1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the light emission characteristics when a direct current voltage is applied to the manufactured organic EL element.
　実施例１０～２１および比較例１～６で作製した有機ＥＬ素子を用いて、素子寿命を測定した結果を表１にまとめて示した。素子寿命は、発光開始時の発光輝度（初期輝度）を１００００ｃｄ／ｍ２として定電流駆動を行った時、発光輝度が９５００ｃｄ／ｍ２（初期輝度を１００％とした時の９５％に相当：９５％減衰）に減衰するまでの時間として測定した。 The device life was measured using the organic EL devices produced in Examples 10 to 21 and Comparative Examples 1 to 6, and the results are shown in Table 1. Element life, when the emission start time of the emission luminance (initial luminance) was driven with a constant current as 10000 cd / m 2, equivalent to 95% when the emission luminance is taken as 100% of 9500cd / m 2 (initial luminance: The time to decay to 95%) was measured.
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000097
　表１に示すように、本開示のアリールアミン化合物を第二正孔輸送材料としてそれぞれ用いた実施例１０～１５と、前記化合物(ＨＴＭ－２)及び前記化合物(Ｂ－２２)を第二正孔輸送材料としてそれぞれ用いた比較例１～４との比較において、電流密度１０ｍＡ／ｃｍ２の電流を流したときの発光効率は、比較例１～４の有機ＥＬ素子の７２．０６～７３．０３ｃｄ／Ａに対し、実施例１０～１５の有機ＥＬ素子では７６．０５～７８．００ｃｄ／Ａと高効率であった。また、電力効率においても、比較例１～４の有機ＥＬ素子の５２．００～５３．２７ｌｍ／Ｗに対し、実施例１０～１５の有機ＥＬ素子では５７．３１～５８．９９ｌｍ／Ｗと高効率であった。一方、素子寿命（９５％減衰）においては、比較例１～４の有機ＥＬ素子では３４１～４００時間であったのに対し、実施例１０～１５の有機ＥＬ素子では４６１～５８５時間であり、大きく長寿命化していることが分かる。 As shown in Table 1, Examples 10-15 using the arylamine compound of the present disclosure as the second hole transport material, the compound (HTM-2) and the compound (B-22) as the second positive. In comparison with Comparative Examples 1 to 4 respectively used as the hole transport material, the luminous efficiency when passing a current density of 10 mA / cm 2 is 72.06 to 73. of the organic EL elements of Comparative Examples 1 to 4. The efficiency was as high as 76.05 to 78.00 cd / A in the organic EL elements of Examples 10 to 15 with respect to 03 cd / A. Further, with respect to the power efficiency, the organic EL elements of Examples 10 to 15 are as high as 57.31 to 58.99 lm / W, compared with 52.00 to 53.27 lm / W of the organic EL elements of Comparative Examples 1 to 4. It was efficient. On the other hand, the element life (95% attenuation) was 341 to 400 hours for the organic EL elements of Comparative Examples 1 to 4, but 461 to 585 hours for the organic EL elements of Examples 10 to 15, It can be seen that the service life is greatly extended.
　表１に示すように、本開示のアリールアミン化合物を第二正孔輸送材料及び第２ホスト材料として用いた実施例１６～２１と、前記化合物(ＨＴＭ－２)を第二正孔輸送材料及び第２ホスト材料として用いた比較例５，６、及び前記化合物(Ｂ－２２)を第二正孔輸送材料および第２ホスト材料として用いた比較例３，４との比較において、電流密度１０ｍＡ／ｃｍ２の電流を流したときの発光効率は、比較例３～６の有機ＥＬ素子の６３．７４～７３．０３ｃｄ／Ａに対し、実施例１６～２１の有機ＥＬ素子では７３．９８～７６．０４ｃｄ／Ａと高効率であった。また、電力効率においても、比較例３～６の有機ＥＬ素子の４５．９３～５３．２７ｌｍ／Ｗに対し、実施例１６～２１の有機ＥＬ素子では５５．５３～５６．３２ｌｍ／Ｗと高効率であった。一方、素子寿命（９５％減衰）においては、比較例３～６の有機ＥＬ素子では３０９～３８４時間であったのに対し、実施例１６～２１の有機ＥＬ素子では４０８～４８０時間であり、大きく長寿命化していることが分かる。 As shown in Table 1, Examples 16 to 21 using the arylamine compound of the present disclosure as a second hole transport material and a second host material, the compound (HTM-2) as a second hole transport material, and In comparison with Comparative Examples 5 and 6 used as the second host material and Comparative Examples 3 and 4 using the compound (B-22) as the second hole transport material and the second host material, the current density is 10 mA / The luminous efficiency when a current of 2 cm 2 was passed was 73.98 to 76 for the organic EL devices of Examples 16 to 21, compared to 63.74 to 73.03 cd / A for the organic EL devices of Comparative Examples 3 to 6. The efficiency was as high as .04 cd / A. Further, with respect to the power efficiency, the organic EL elements of Examples 16 to 21 are as high as 55.53 to 56.32 Im / W, compared with 45.93 to 53.27 Im / W of the organic EL elements of Comparative Examples 3 to 6 It was efficient. On the other hand, the element life (95% attenuation) was 309 to 384 hours for the organic EL elements of Comparative Examples 3 to 6, while it was 408 to 480 hours for the organic EL elements of Examples 16 to 21, It can be seen that the service life is greatly extended.
　表１の結果から明らかなように、電子輸送能が高い第１ホスト材料と、正孔輸送能を有する第２ホスト材料を共に使用した発光層を備える有機ＥＬ素子であって、本開示のアリールアミン化合物を第二正孔輸送層の材料として用いた有機ＥＬ素子は、同じくアリールアミン化合物である前記化合物（ＨＴＭ－２）を用いた有機ＥＬ素子と比較しても、電力効率の向上や、長寿命化を達成できることがわかった。これは本開示のアリールアミン化合物がＨＴＭ－２のＴ１より大きな値を有していることに起因している。本開示のアリールアミン化合物を用いた有機ＥＬ素子はＨＴＭ－２を用いた有機ＥＬ素子に比べ、発光層で励起された三重項励起子を充分閉じ込めることができている。これにより、効率特性の向上と同時に寿命特性も顕著に改善された有機ＥＬ素子が実現されている。またカルバゾール誘導体である前記化合物（Ｂ－２２）を第二正孔輸送層の材料として用いた有機ＥＬ素子と比較しても、電力効率の向上や、長寿命化を達成できることがわかった。特定の構造を有するアリールアミン化合物を組み合わせることによって、正孔が効率良く発光層へ供給され、発光層内での電子過多が改善された。これにより、発光層内のキャリアバランスがより精緻化され、効率特性の向上と同時に寿命特性も顕著に改善させた有機ＥＬ素子が実現されている。 As is clear from the results of Table 1, an organic EL device comprising the light emitting layer using both the first host material having high electron transporting ability and the second host material having hole transporting ability, which is an aryl of the present disclosure The organic EL device using the amine compound as the material of the second hole transport layer is improved in power efficiency as compared with the organic EL device using the compound (HTM-2) which is also the arylamine compound, It turned out that long life can be achieved. This is due to the fact that the arylamine compound of the present disclosure has a value greater than T1 of HTM-2. The organic EL device using the arylamine compound of the present disclosure is capable of sufficiently confining triplet excitons excited in the light emitting layer, as compared to the organic EL device using HTM-2. As a result, an organic EL element is realized in which the lifetime characteristics are significantly improved simultaneously with the improvement of the efficiency characteristics. It was also found that the power efficiency can be improved and the life can be extended even when compared with the organic EL device using the compound (B-22) which is a carbazole derivative as a material of the second hole transport layer. By combining an arylamine compound having a specific structure, holes are efficiently supplied to the light emitting layer, and the electron excess in the light emitting layer is improved. As a result, the carrier balance in the light emitting layer is further refined, and an organic EL element is realized in which the efficiency characteristics are improved and the lifetime characteristics are significantly improved.
　さらに本開示のアリールアミン化合物を第２ホスト材料として用いた有機ＥＬ素子では、同じくアリールアミン化合物である前記化合物（ＨＴＭ－２）を用いた有機ＥＬ素子と比較しても、電力効率の向上や、長寿命化を達成できることがわかった。本開示のアリールアミン化合物は緑色燐光性発光材料である前記化合物（化合物３－３）がもつＴ１より大きい値を有しており、第２ホスト材料として用いても励起された三重項励起子を充分閉じ込めることができている。一方、ＨＴＭ－２はＴ１が低く三重項励起子の閉じ込めが不充分であり、励起した三重項励起子が失活することで、発光効率と素子寿命が大きく低下した。またカルバゾール誘導体である前記化合物（Ｂ－２２）と比較しても電力効率の向上や、長寿命化を達成できることがわかった。優れた電気的耐久性と、優れた正孔輸送能を有する特定のアリールアミン化合物を組み合わせることによって、正孔が効率良く発光層へ供給され、発光層内での電子過多が改善された。これにより、発光層内のキャリアバランスがより精緻化され、効率特性の向上と同時に寿命特性も顕著に改善させた有機ＥＬ素子が実現されている。 Furthermore, in the organic EL device using the arylamine compound of the present disclosure as the second host material, the power efficiency can be improved as compared with the organic EL device using the compound (HTM-2), which is also the arylamine compound. It turned out that long life can be achieved. The arylamine compound of the present disclosure has a value larger than T 1 possessed by the above-mentioned compound (compound 3-3) which is a green phosphorescent light-emitting material, and an excited triplet exciton is obtained even when used as a second host material It can be confined enough. On the other hand, HTM-2 has low T1 and insufficient confinement of triplet excitons, and the deactivation of the excited triplet excitons significantly reduces the luminous efficiency and the device lifetime. It was also found that the improvement of the power efficiency and the prolongation of the life can be achieved as compared with the above-mentioned compound (B-22) which is a carbazole derivative. By combining a specific arylamine compound having excellent electrical durability and excellent hole transporting ability, holes are efficiently supplied to the light emitting layer, and the electron excess in the light emitting layer is improved. As a result, the carrier balance in the light emitting layer is further refined, and an organic EL element is realized in which the efficiency characteristics are improved and the lifetime characteristics are significantly improved.
　なお、本願は、２０１７年１２月５日付で出願された日本国特許出願（特願２０１７－２３３１４８）に基づいており、その全体が引用により援用される。また、ここに引用されるすべての参照は全体として取り込まれる。
　本発明を特定の態様を参照して詳細に説明したが、本発明の精神と範囲を離れることなく様々な変更および修正が可能であることは、当業者にとって明らかである。 The present application is based on the Japanese Patent Application (Japanese Patent Application No. 2017-233148) filed on December 5, 2017, which is incorporated by reference in its entirety. Also, all references cited herein are taken as a whole.
Although the present invention has been described in detail with reference to particular 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 present invention.
　本発明の有機ＥＬ素子は、発光効率が向上するとともに耐久性が大きく改善されており、例えば、家庭電化製品や照明の用途への展開が可能となった。 The organic EL device of the present invention is improved in luminous efficiency and greatly improved in durability. For example, it has become possible to develop home appliances and lighting applications.
　１　　ガラス基板
　２　　透明陽極
　３　　正孔注入層
　４　　第一正孔輸送層
　５　　第二正孔輸送層
　６　　発光層
　７　　電子輸送層
　８　　電子注入層
　９　　陰極 Reference Signs List 1 glass substrate 2 transparent anode 3 hole injection layer 4 first hole transport layer 5 second hole transport layer 6 light emitting layer 7 electron transport layer 8 electron injection layer 9 cathode

Claims (9)

  1. 　陽極と陰極との間に、陽極側から少なくとも第一正孔輸送層と第二正孔輸送層と緑色発光層と電子輸送層とをこの順に備え、前記第一正孔輸送層と前記電子輸送層との間に配置された層のうちの少なくとも一層は、下記一般式（１）で表される、アリールアミン化合物を含有する、有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000001
     （式中、Ａｒ１、Ａｒ2、Ａｒ３、Ａｒ４はそれぞれ同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。）     Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a green light emitting layer and an electron transport layer are provided in this order from the anode side, and the first hole transport layer and the electron transport An organic EL device, wherein at least one of the layers disposed between the layer and the layer contains an arylamine compound represented by the following general formula (1).
    Figure JPOXMLDOC01-appb-C000001
     (Wherein, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent Good C 2 -C 6 linear or branched alkenyl group, C 1 -C 6 linear or branched alkyloxy group which may have substituent (s), substituent (s) May have 5 carbon atoms 10 cycloalkyloxy groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted fused polycyclic aromatic groups or substituted or unsubstituted aryloxy groups Represents
  2. 　陽極と陰極との間に、陽極側から少なくとも第一正孔輸送層と第二正孔輸送層と緑色発光層と電子輸送層とをこの順に備え、前記第一正孔輸送層と前記電子輸送層との間に配置された層のうちの少なくとも一層は、下記一般式（２）で表される、アリールアミン化合物を含有する、有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000002
     （式中、Ａｒ１、Ａｒ2は相互に同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ５、Ａｒ６は相互に同一でも異なってもよく、フェニル基、ビフェニリル基、ナフチル基、フェナントレニル基、またはフルオレニル基を表し、Ｒ４は水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。）     Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a green light emitting layer and an electron transport layer are provided in this order from the anode side, and the first hole transport layer and the electron transport An organic EL device, wherein at least one of the layers disposed between the layer and the layer contains an arylamine compound represented by the following general formula (2).
    Figure JPOXMLDOC01-appb-C000002
     (Wherein, Ar 1 and Ar 2 may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted fused polycyclic aromatic compounds Ar 5 and Ar 6 may be identical to or different from each other, and may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group or a fluorenyl group, R 4 is a hydrogen atom, a deuterium atom or a fluorine atom A chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a carbon number of 5 to a carbon atom which may have a substituent, 10 cycloalkyl groups, C2-C6 linear or branched alkenyl groups which may have substituents, C1-C6 linear groups which may have substituents The state is also And a branched alkyloxy group, a substituted or unsubstituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic ring A group, a substituted or unsubstituted fused polycyclic aromatic group or a substituted or unsubstituted aryloxy group)
  3. 　前記緑色発光層は、ホストと燐光発光性ドーパントとを含み、前記ホストは、下記の化学式Ｈｏｓｔ－Ａで表される少なくとも１種の第１ホスト化合物と、下記の化学式Ｈｏｓｔ－Ｂで表される少なくとも１種の第２ホスト化合物と、を含む、請求項１または２に記載の有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000003
     （前記Ｈｏｓｔ－Ａ中、Ｚは、それぞれ独立して、ＮまたはＣＲａであり、Ｚのうちの少なくとも一つは、Ｎであり、Ｒ５～Ｒ１４およびＲａは、それぞれ独立して、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換もしくは無置換の炭素数１ないし１５のアルキル基、置換もしくは無置換の環形成炭素数６ないし１２のアリール基であり、前記Ｈｏｓｔ－Ａでトリフェニレン基に置換された６員環の総個数は、６個以下であり、Ｌ１は、置換もしくは無置換のフェニレン基、置換もしくは無置換のビフェニレン基または置換もしくは無置換のターフェニレン基であり、ｎ１～ｎ３は、それぞれ独立して、０または１であり、ｎ１＋ｎ２＋ｎ３≧１である。）
    Figure JPOXMLDOC01-appb-C000004
     （前記Ｈｏｓｔ－Ｂ中、Ｙは単結合、置換若しくは無置換の環形成炭素数６ないし３０のアリーレン基、又は置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリーレン基であり、Ａｒ７は、置換若しくは無置換の環形成炭素数６ないし３０のアリール基、置換若しくは無置換の環形成炭素数５ないし３０のヘテロアリール基であり、Ｒ１５～Ｒ１８は、それぞれ独立して、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、炭素数１ないし１５のアルキル基、置換若しくは無置換の環形成炭素数６ないし５０のアリール基、または置換若しくは無置換の環形成炭素数４ないし５０のヘテロアリール基であり、Ｒ１５～Ｒ１８およびＡｒ７のうちの少なくとも一つは、置換もしくは無置換のトリフェニレン基または置換もしくは無置換のカルバゾリル基を含む。）     The green light emitting layer includes a host and a phosphorescent dopant, and the host is represented by the following chemical formula Host-B, and at least one first host compound represented by the following chemical formula Host-A. The organic EL device according to claim 1, comprising at least one second host compound.
    Figure JPOXMLDOC01-appb-C000003
     (In the above Host-A, Z is each independently N or CRa, at least one of Z is N, and R 5 to R 14 and Ra are each independently a hydrogen atom Deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, The total number of 6-membered rings substituted with a triphenylene group in Host-A is 6 or less, and L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted ter And n1 to n3 each independently represent 0 or 1, and n1 + n2 + n3 ≧ 1).
    Figure JPOXMLDOC01-appb-C000004
     (In the above Host-B, Y is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, Ar 7 Is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and R 15 to R 18 each independently represent hydrogen Atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring forming C 4 -C to a heteroaryl group 50, at least one of R 15 ~ R 18 and Ar 7 represents a substituted or unsubstituted triphenylene Or a substituted or unsubstituted carbazolyl group.)
  4. 　前記緑色発光層は、ホストと燐光発光性ドーパントとを含み、前記燐光発光性ドーパントは、イリジウムを含む金属錯体である、請求項１～３のいずれか一項に記載の有機ＥＬ素子。 The organic EL device according to any one of claims 1 to 3, wherein the green light emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex containing iridium.
  5. 　前記緑色発光層は、ホストと燐光発光性ドーパントとを含み、前記燐光発光性ドーパントは、下記一般式（３）で表される金属錯体である、請求項１～３のいずれか一項に記載の有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000005
     （式中、Ｒ１９～Ｒ３４はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、トリメチルシリル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換のアリールオキシ基、または芳香族炭化水素基、芳香族複素環基および縮合多環芳香族基からなる群から選ばれる基によって置換されたジ置換アミノ基を表す。ｎは１～３の整数を表す。）     The green light emitting layer according to any one of claims 1 to 3, wherein the green light emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex represented by the following general formula (3). Organic EL elements.
    Figure JPOXMLDOC01-appb-C000005
     (Wherein, R 19 to R 34 may be the same as or different from each other, and are each independently a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, or a C1-C6 linear group optionally having substituents) Or a branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched chain having 2 to 6 carbon atoms An alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent Trimethylsilyl group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted fused polycyclic aromatic group, substituted or unsubstituted aryloxy group, or .n representing the family hydrocarbon group, disubstituted amino group substituted by a group selected from the group consisting of aromatic heterocyclic groups and fused polycyclic aromatic group is an integer of 1-3.)
  6. 　前記電子輸送層は、下記一般式（４）で表される、ピリミジン構造を有する化合物を含有する、請求項１～５のいずれか一項に記載の有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000006
     （式中、Ａｒ８は、置換もしくは無置換の芳香族炭化水素基、または置換もしくは無置換の縮合多環芳香族基を表し、Ａｒ９、Ａｒ１０は相互に同一でも異なっていてもよく、水素原子、置換もしくは無置換の芳香族炭化水素基、または置換もしくは無置換の縮合多環芳香族基を表し、Ｂは、下記構造式（５）で示される１価基を表す。ここで、Ａｒ９とＡｒ１０は同時に水素原子となることはない。）
    Figure JPOXMLDOC01-appb-C000007
     （式中、Ａｒ１１は、置換もしくは無置換の芳香族複素環基を表し、Ｒ３５～Ｒ３８は、それぞれ同一でも異なっていてもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、または置換もしくは無置換の縮合多環芳香族基を表す。）     The organic EL device according to any one of claims 1 to 5, wherein the electron transport layer contains a compound having a pyrimidine structure, which is represented by the following general formula (4).
    Figure JPOXMLDOC01-appb-C000006
     (Wherein, Ar 8 represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted fused polycyclic aromatic group, and Ar 9 and Ar 10 may be the same as or different from each other, B represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted fused polycyclic aromatic group, and B represents a monovalent group represented by the following structural formula (5): Ar 9 and Ar 10 can not simultaneously be hydrogen atoms.)
    Figure JPOXMLDOC01-appb-C000007
     (Wherein, Ar 11 represents a substituted or unsubstituted aromatic heterocyclic group, and R 35 to R 38 may be the same or different and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, A cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group; Represents an unsubstituted fused polycyclic aromatic group).
  7. 　前記電子輸送層は、下記一般式（６）で表される、ベンゾアゾール構造を有する化合物を含有する、請求項１～５のいずれか一項に記載の有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000008
     （式中、Ａｒ１２、Ａｒ１３は相互に同一でも異なっていてもよく、水素原子、重水素原子、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の縮合多環芳香族基、または置換もしくは無置換の芳香族複素環基を表し、V１は置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の縮合多環芳香族基、置換もしくは無置換の芳香族複素環基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、または置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基を表し、Ｘは酸素原子または硫黄原子を表し、Ｗ１、Ｗ２は相互に同一でも異なっていてもよく、炭素原子または窒素原子を表す。）     The organic EL device according to any one of claims 1 to 5, wherein the electron transport layer contains a compound having a benzoazole structure, which is represented by the following general formula (6).
    Figure JPOXMLDOC01-appb-C000008
     (Wherein, Ar 12 and Ar 13 may be the same as or different from each other, and are a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, Or a substituted or unsubstituted aromatic heterocyclic group, wherein V 1 is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted aromatic heterocyclic group A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent And X 2 represents a linear or branched alkenyl group having 2 to 6 carbon atoms which may have X, an oxygen atom or a sulfur atom, and W 1 and W 2 may be the same or different from each other Well, carbon atom or nitrogen It represents an atom.)
  8. 　前記第一正孔輸送層は、下記一般式（７）または一般式（８）で表されるトリフェニルアミン誘導体を含有する、請求項１～７のいずれか一項に記載の有機ＥＬ素子。
    Figure JPOXMLDOC01-appb-C000009
     （式中、Ｒ３９～Ｒ４４は、それぞれ独立して、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５～１０のシクロアルキル基、置換基を有していてもよい炭素原子数２～６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５～１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または置換もしくは無置換のアリールオキシ基を表す。ｒ１～ｒ６はそれぞれ同一でも異なっていてもよく、ｒ１～ｒ４は０～５の整数を表し、ｒ５、ｒ６は０～４の整数を表す。ｒ１～ｒ６が２以上の整数である場合、同一のベンゼン環に複数個結合するＲ３９～Ｒ４４はそれぞれ同一でも異なっていてもよい。また、ベンゼン環とベンゼン環に置換された置換基とが、同一のベンゼン環に複数置換された置換基同士が、および窒素原子を介して互いに隣接するベンゼン環同士が、それぞれ単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子により結合して環を形成してもよい。Ｋ１は下記構造式（ＨＴＭ－Ａ）～（ＨＴＭ－Ｆ）で示される２価基、または単結合を表す。）
    Figure JPOXMLDOC01-appb-C000010
     （式中、ｊは１～３の整数を表す。）
    Figure JPOXMLDOC01-appb-C000011
    Figure JPOXMLDOC01-appb-C000012
    Figure JPOXMLDOC01-appb-C000013
    Figure JPOXMLDOC01-appb-C000014
    Figure JPOXMLDOC01-appb-C000015
    Figure JPOXMLDOC01-appb-C000016
     （式中、Ｒ４５～Ｒ５６は、それぞれ独立して、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５～１０のシクロアルキル基、置換基を有していてもよい炭素原子数２～６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１～６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５～１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基、または置換もしくは無置換のアリールオキシ基を表す。ｒ７～ｒ１８はそれぞれ同一でも異なっていてもよく、ｒ７～ｒ１２は０～５の整数を表し、ｒ１３～ｒ１８は０～４の整数を表す。ｒ７～ｒ１８が２以上の整数である場合、同一のベンゼン環に複数個結合するＲ４５～Ｒ５６はそれぞれ同一でも異なっていてもよい。また、ベンゼン環とベンゼン環に置換された置換基とが、同一のベンゼン環に複数置換された置換基同士が、および窒素原子を介して互いに隣接するベンゼン環同士が、それぞれ単結合、置換もしくは無置換のメチレン基、酸素原子または硫黄原子により結合して環を形成してもよい。Ｋ２～Ｋ４はそれぞれ同一でも異なってもよく、一般式（７）に記載の（ＨＴＭ－Ａ）～（ＨＴＭ－Ｆ）で示される２価基、または単結合を表す。）     The organic EL device according to any one of claims 1 to 7, wherein the first hole transporting layer contains a triphenylamine derivative represented by the following general formula (7) or (8).
    Figure JPOXMLDOC01-appb-C000009
     (Wherein, R 39 to R 44 each independently represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear C 1-6 linear chain that may have a substituent) Or branched alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, and optionally substituted linear or branched 2 to 6 carbon atoms Alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, cycloalkylo having 5 to 10 carbon atoms which may have a substituent R 1 represents a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. each be the same or different is ~ r 6 At best, if r 1 ~ r 4 represents an integer of 0 to 5, r 5, r 6 is .r 1 ~ r 6 represents an integer of 0 to 4 represent an integer of 2 or more, the same benzene ring Each of R 39 to R 44 bonded to plural groups may be the same or different from each other, and the benzene ring and the substituent substituted to the benzene ring may be substituted each other by plural substituents on the same benzene ring. and via the nitrogen atom is a benzene ring which are adjacent to each other, each a single bond, a substituted or unsubstituted methylene group, optionally .K 1 be bonded to an oxygen atom or a sulfur atom to form a ring is represented by the following general formula ( HTM-A) to (HTM-F) represents a divalent group or a single bond.)
    Figure JPOXMLDOC01-appb-C000010
     (Wherein, j represents an integer of 1 to 3)
    Figure JPOXMLDOC01-appb-C000011
    Figure JPOXMLDOC01-appb-C000012
    Figure JPOXMLDOC01-appb-C000013
    Figure JPOXMLDOC01-appb-C000014
    Figure JPOXMLDOC01-appb-C000015
    Figure JPOXMLDOC01-appb-C000016
     (Wherein, R 45 to R 56 each independently represent a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear chain having 1 to 6 carbon atoms which may have a substituent) Or branched alkyl group, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, and optionally substituted linear or branched 2 to 6 carbon atoms Alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, cycloalkylo having 5 to 10 carbon atoms which may have a substituent R 7 represents a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group. or different from each ~ r 18 the same May have, if r 7 ~ r 12 represents an integer of 0 ~ 5, r 13 ~ r 18 is .r 7 ~ r 18 represents an integer of 0 to 4 represent an integer of 2 or more, the same benzene ring And R 45 to R 56 bonded to each other may be the same as or different from each other, and the benzene ring and the substituents substituted on the benzene ring may be substituents each substituted on the same benzene ring, and via the nitrogen atom is a benzene ring which are adjacent to each other, each a single bond, a substituted or unsubstituted methylene group, an oxygen atom or .K 2 ~ K 4 be bonded to the sulfur atom to form a ring respectively It may be the same or different, and represents a divalent group represented by (HTM-A) to (HTM-F) described in General Formula (7), or a single bond.)
  9. 　下記一般式（１）で表される、アリールアミン化合物。
    Figure JPOXMLDOC01-appb-C000017
     （式中、Ａｒ１、Ａｒ2、Ａｒ３、Ａｒ４はそれぞれ同一でも異なってもよく、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、Ｒ１、Ｒ２、Ｒ３はそれぞれ同一でも異なってもよく、水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、ニトロ基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキル基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキル基、置換基を有していてもよい炭素原子数２ないし６の直鎖状もしくは分岐状のアルケニル基、置換基を有していてもよい炭素原子数１ないし６の直鎖状もしくは分岐状のアルキルオキシ基、置換基を有していてもよい炭素原子数５ないし１０のシクロアルキルオキシ基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基、置換もしくは無置換の縮合多環芳香族基または置換もしくは無置換のアリールオキシ基を表す。）     The arylamine compound represented by following General formula (1).
    Figure JPOXMLDOC01-appb-C000017
     (Wherein, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different, and each is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group R 1 , R 2 and R 3 may be the same or different and each has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a substituent Good C 2 -C 6 linear or branched alkenyl group, C 1 -C 6 linear or branched alkyloxy group which may have substituent (s), substituent (s) May have 5 carbon atoms 10 cycloalkyloxy groups, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted fused polycyclic aromatic groups or substituted or unsubstituted aryloxy groups Represents
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