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WO2019111844A1 - Composé d'arylamine et élément électroluminescent organique - Google Patents

Composé d'arylamine et élément électroluminescent organique 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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望月　俊二
剛史 山本
幸喜 加瀬
駿河　和行
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Hodogaya Chemical Co Ltd
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Hodogaya Chemical Co Ltd
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Priority to KR1020207014080A priority Critical patent/KR102705103B1/ko
Priority to JP2019558196A priority patent/JP7163311B2/ja
Priority to CN201880078675.4A priority patent/CN111433930B/zh
Publication of WO2019111844A1 publication Critical patent/WO2019111844A1/fr
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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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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Luminescent Compositions (AREA)

Abstract

Dispositif EL organique qui comprend au moins, entre une anode et une cathode, une première couche de transport de trous, une seconde couche de transport de trous, une couche d'émission de lumière verte et une couche de transport d'électrons dans cet ordre à partir du côté anode, au moins une couche disposée entre la première couche de transport de trous et la couche de transport d'électrons contenant un composé d'arylamine représenté par la formule générale (1).
PCT/JP2018/044353 2017-12-05 2018-12-03 Composé d'arylamine et élément électroluminescent organique Ceased WO2019111844A1 (fr)

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JP2019558196A JP7163311B2 (ja) 2017-12-05 2018-12-03 有機エレクトロルミネッセンス素子
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WO2025060725A1 (fr) * 2023-09-20 2025-03-27 京东方科技集团股份有限公司 Composés amines aromatiques, dispositif électroluminescent et appareil d'affichage

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