WO2014112360A1 - Composé ayant une structure de cycle indéno-acridane, et élément électroluminescent organique - Google Patents

Composé ayant une structure de cycle indéno-acridane, et élément électroluminescent organique Download PDF

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WO2014112360A1
WO2014112360A1 PCT/JP2014/000131 JP2014000131W WO2014112360A1 WO 2014112360 A1 WO2014112360 A1 WO 2014112360A1 JP 2014000131 W JP2014000131 W JP 2014000131W WO 2014112360 A1 WO2014112360 A1 WO 2014112360A1
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紀昌 横山
大三 神田
秀一 林
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保土谷化学工業株式会社
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    • C07—ORGANIC CHEMISTRY
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    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a compound suitable for an organic electroluminescence element, which is a self-luminous element suitable for various display devices, and to the element. Specifically, the present invention relates to a compound having an indenoacridan ring structure and the compound. The present invention relates to an organic electroluminescence device.
  • organic electroluminescence elements are self-luminous elements, they have been actively researched because they are brighter and have better visibility than liquid crystal elements and can be clearly displayed.
  • organic electroluminescence elements using organic materials practical by developing a laminated structure element that shares various roles with each material. They are composed of a phosphor capable of transporting electrons, tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ) and an aromatic amine compound capable of transporting holes, Was injected into the phosphor layer to emit light, whereby high luminance of 1000 cd / m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).
  • Non-Patent Document 2 the use of triplet excitons has been attempted for the purpose of further improving the luminous efficiency, and the use of phosphorescent emitters has been studied (for example, see Non-Patent Document 2).
  • the light emitting layer can also be prepared by doping a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
  • a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
  • the light injected from both electrodes recombines in the light emitting layer to obtain light emission.
  • Improve the probability of recombination of holes and electrons by increasing the hole injection property and blocking the electron injected from the cathode, and further confine excitons generated in the light emitting layer
  • high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.
  • the heat resistance and amorphous nature of the material are important for the lifetime of the element.
  • thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated.
  • the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.
  • NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
  • Amine derivatives have been known (see, for example, Patent Document 1 and Patent Document 2).
  • NPD has a good hole transport capability, but its glass transition point (Tg), which is an index of heat resistance, is as low as 96 ° C., and device characteristics are degraded due to crystallization under high temperature conditions (for example, Non-Patent Document 3).
  • arylamine compounds having a substituted acridan structure represented by the following formula have been proposed. (For example, see Patent Documents 3 to 5).
  • JP-A-8-048656 Japanese Patent No. 3194657 WO2006 / 033563 publication WO2007 / 110228 publication WO 2010/147319
  • the object of the present invention is as a highly efficient and durable organic electroluminescent device material, excellent in hole injection / transport performance, electron blocking ability, high stability in a thin film state, and heat resistance It is another object of the present invention to provide an organic compound having excellent characteristics and to provide an organic electroluminescence device having high luminous efficiency and durability using this compound.
  • the physical characteristics that the organic compound to be provided by the present invention should have include (1) good hole injection characteristics, (2) high hole mobility, and (3) electron blocking ability. (4) The thin film state is stable, and (5) The heat resistance is excellent.
  • the physical characteristics of the organic electroluminescent device to be provided by the present invention include (1) high luminous efficiency and power efficiency, (2) low emission start voltage, and (3) practical use. The drive voltage is low.
  • the inventors of the present invention have an aromatic tertiary amine structure having a high hole injection / transport capability, and an indenoacridan ring structure has an electron blocking property.
  • a compound having an indenoacridan ring structure is designed and chemically synthesized. As a result of prototyping an electroluminescence element and intensively evaluating the characteristics of the element, the present invention has been completed.
  • the present invention is a compound having an indenoacridan ring structure represented by the following general formula (1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond;
  • a and B 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.
  • the present invention is a compound having an indenoacridan ring structure described in the above 1) represented by the following general formula (1-1).
  • A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted condensed polycyclic aromatic divalent group
  • Ar 1 and Ar 2 represent They may be the same as or different from each other, and may have a substituent, a vinyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation.
  • Ar 1 and Ar 2 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
  • R 1 to R 10 May be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group or a linear or branched chain having 1 to 6 carbon atoms which may have a substituent.
  • alkyl groups and substituents A cycloalkyl group having 5 to 10 carbon atoms which may be present, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a substituent.
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, which is a single bond, a substituted or unsubstituted methylene group, an oxygen atom or R 11 to R 14 may be the same or different from each other and may have a substituent and may be a straight chain having 1 to 6 carbon atoms.
  • a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, 11 and R 12 , R 13 and R 14 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, where A and Ar 1 are Single bond, substitution Properly unsubstituted m
  • the present invention also provides an index according to the above 1), wherein in the general formula (1), A is a substituted or unsubstituted aromatic hydrocarbon or a substituted or unsubstituted condensed polycyclic aromatic divalent group. It is a compound having a noacridan ring structure.
  • the present invention also provides an indenoacridan ring structure according to the above 3), wherein in the general formula (1), A is a divalent group formed by removing two hydrogen atoms from substituted or unsubstituted phenyl. It is a compound that has.
  • the present invention also provides an indenoacridan ring structure according to 3) above, wherein in the general formula (1), A is a divalent group formed by removing two hydrogen atoms from substituted or unsubstituted biphenyl. It is a compound that has.
  • the present invention also provides an indenoacridan ring structure according to the above 1), wherein, in the general formula (1), A is a divalent group formed by removing two hydrogen atoms from a substituted or unsubstituted indole. It is a compound that has.
  • this invention is a compound which has the indenoacridan ring structure of said 1) description whose said B is a substituted or unsubstituted carbazolyl group in the said General formula (1).
  • this invention is a compound which has the indenoacridan ring structure of said 1) description whose said B is a substituted or unsubstituted dibenzofuranyl group in the said General formula (1).
  • the present invention is a compound having an indenoacridan ring structure according to the above 1), wherein B in the general formula (1) is a substituted or unsubstituted phenyl group.
  • the present invention also relates to a compound having an indenoacridan ring structure as described in 1) above, wherein B in the general formula (1) is a substituted or unsubstituted biphenyl group.
  • the present invention provides an organic electroluminescent device having a pair of electrodes and at least one organic layer sandwiched between them, wherein the indenoacridan ring structure according to any one of 1) to 10) above is used.
  • the organic electroluminescent element is characterized in that the compound having the above-mentioned compound is used as a constituent material of at least one organic layer.
  • this invention is an organic electroluminescent element of said 11) description whose said organic layer is a positive hole transport layer.
  • this invention is an organic electroluminescent element of said 11) description whose said organic layer is an electron blocking layer.
  • this invention is an organic electroluminescent element of the said 11) description whose said organic layer is a positive hole injection layer.
  • this invention is an organic electroluminescent element of the said 11) description whose said organic layer is a light emitting layer.
  • substituted or unsubstituted aromatic hydrocarbon substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group
  • a in the general formula (1) “Aromatic hydrocarbon”, “Aromatic heterocycle” of “Substituted or unsubstituted aromatic hydrocarbon”, “Substituted or unsubstituted aromatic heterocycle” or “Substituted or unsubstituted condensed polycyclic aromatic”
  • the “fused polycyclic aromatic specifically, benzene, biphenyl, terphenyl, tetrakisphenyl, styrene, naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene, indane, pyrene, pyridine, pyrimidine, triazine, furan, Pyran, thiophene, indole, quino
  • a divalent group of a substituted or unsubstituted aromatic hydrocarbon “a divalent group of a substituted or unsubstituted aromatic heterocyclic ring” or “substituted or
  • the “unsubstituted fused polycyclic aromatic divalent group” is a divalent group formed by removing two hydrogen atoms from the above “aromatic hydrocarbon”, “aromatic heterocycle” or “fused polycyclic aromatic”.
  • aromatic heterocycle in the “divalent group of a substituted or unsubstituted aromatic heterocycle” is a sulfur-containing aromatic heterocycle such as thiophene, benzothiophene, benzothiazole, dibenzothiophene, or furan.
  • Oxygen-containing aromatic heterocycles such as pyran, benzofuran, benzoxazole and dibenzofuran, indole and carbazole are preferred.
  • a divalent group of a substituted or unsubstituted aromatic hydrocarbon a divalent group of a substituted or unsubstituted condensed polycyclic aromatic
  • an indole or carbazole to a hydrogen atom Is preferably a divalent group formed by removing two hydrogen atoms from benzene, biphenyl or indole.
  • substituted or unsubstituted aromatic hydrocarbon substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group
  • substituted or unsubstituted aromatic heterocyclic ring or substituted or unsubstituted condensed polycyclic aromatic divalent group represented by A in the general formula (1)
  • the group may be further substituted by the above-exemplified substituents. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • aromatic hydrocarbon group aromatic heterocyclic group or “fused polycyclic aromatic group”
  • phenyl group biphenylyl group, terphenylyl group, naphthyl group, anthryl group, phenanthryl group , Fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl Group, benzoxazo
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by B in the general formula (1), specifically, , Deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert A linear or branched alkyl group having 1 to 6 carbon atoms such as a butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, or an n-hexyl group; a methyloxy group, an ethyloxy group, a propyloxy group, or the like; A linear or branched alkyl group having 1 to 6 carbon atoms such as a but
  • Aromatic hydrocarbon in “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group” represented by B in the general formula (1)
  • aromatic heterocyclic group or “fused polycyclic aromatic group”
  • substituted or unsubstituted aromatic hydrocarbons represented by B in the above general formula (1)
  • Aromatic hydrocarbon group "aromatic heterocyclic group” or “fused polycycle” in “group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group”
  • the same groups as those shown for the “aromatic group” can be mentioned.
  • these groups may have a substituent, and as the substituent, the above-mentioned “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group”
  • substituent the above-mentioned “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group”
  • lifted and a preferable aspect can also mention the same thing.
  • aromatic heterocyclic group in the “substituted or unsubstituted aromatic heterocyclic group” of B in the general formula (1) is sulfur-containing such as thienyl group, benzothienyl group, benzothiazolyl group, dibenzothienyl group, etc.
  • An aromatic heterocyclic group, a furyl group, a pyranyl group, a benzofuranyl group, a benzoxazolyl group, a dibenzofuranyl group, or other oxygen-containing aromatic heterocyclic ring, or a carbazolyl group is preferable.
  • substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted condensed polycyclic aromatic group”, “aromatic hydrocarbon group, aromatic heterocyclic group” Or a “disubstituted amino group substituted by a group selected from condensed polycyclic aromatic groups”, a carbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group, and particularly “a substituted or unsubstituted aromatic hydrocarbon”.
  • a and B in the general formula (1) may be bonded directly or via respective substituents to form a ring. In this case, a single bond, a substituted or unsubstituted methylene group, an oxygen atom Alternatively, it is preferable to bond via a sulfur atom, and it is more preferable to form a ring via a substituted or unsubstituted methylene group.
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 1 to R 10 in the general formula (1), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”.
  • Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclyl Hexyl group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group, and the like 2-butenyl group.
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R 1 to R 10 in general formula (1), “5 to 10 carbon atoms having a substituent”
  • Specific examples of the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a deuterium atom, a cyano group, and a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl groups; aryloxy groups such as phenyloxy groups and tolyloxy groups; arylalkyloxy groups such as benzyloxy groups and phenethyloxy groups; Aromatic hydrocarbon groups or conden
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent represented by R 1 to R 10 in the general formula (1) or “a carbon atom having 5 to 5 carbon atoms having a substituent”
  • Specific examples of the “substituent” in “10 cycloalkyloxy groups” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyloxy group, ethyloxy
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a propyloxy group; an alkenyl group such as an allyl group; an aryloxy group such as a phenyloxy group or a tolyloxy group; a benzyloxy group or a phenethyloxy group
  • Arylalkyloxy groups such as groups; phenyl groups, biphenylyl groups,
  • a group such as a group heterocyclic group may be further substituted by the above-exemplified substituents.
  • These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 10 in the general formula (1) or “substituted or unsubstituted condensed hydrocarbon group”
  • phenanthryl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, Indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, Razoriru group include dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 1 to R 10 in the general formula (1), Specifically, deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl Straight or branched alkyloxy groups having 1 to 6 carbon atoms such as oxy groups;
  • aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R 1 to R 10 in the general formula (1) include a phenyloxy group, a biphenylyloxy group, a terphenyl group.
  • examples thereof include a tolyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group.
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aryloxy group represented by R 1 to R 10 in the general formula (1), specifically, a deuterium atom, a cyano group, a nitro group; a fluorine atom, a chlorine atom, Halogen atoms such as bromine atom and iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n- A linear or branched alkyl group having 1 to 6 carbon atoms such as a hexyl group; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group or a propyloxy group Alkenyl group such as allyl
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent represented by R 11 to R 14 in the general formula (1), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”.
  • Examples of “straight or branched alkyl group of 6”, “cycloalkyl group of 5 to 10 carbon atoms” or “straight chain or branched alkenyl group of 2 to 6 carbon atoms” specifically include Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, Rohekishiru group, 1-adamantyl, 2-adamantyl, vinyl group, allyl group, isopropenyl group include a 2-butenyl group, and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent represented by R 11 to R 14 in the general formula (1), “5 to 10 carbon atoms having a substituent”
  • Specific examples of the “substituent” in the “cycloalkyl group of” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a deuterium atom, a cyano group, and a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl group; aryloxy group such as phenyloxy group and tolyloxy group; arylalkyloxy group such as benzyloxy group and phenethyloxy group; phenyl group; Aroma
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent represented by R 11 to R 14 in the general formula (1) or “a carbon atom having 5 to 5 carbon atoms having a substituent”
  • Specific examples of the “substituent” in “10 cycloalkyloxy groups” include deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyloxy group, ethyloxy
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a propyloxy group; an alkenyl group such as an allyl group; an aryloxy group such as a phenyloxy group or a tolyloxy group; a benzyloxy group or a phenethyloxy group
  • Arylalkyloxy groups such as a group; phenyl group, biphenylyl group
  • substituents may be further substituted by the above-exemplified substituents.
  • substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Substituted or unsubstituted aromatic hydrocarbon group “substituted or unsubstituted aromatic heterocyclic group” represented by R 11 to R 14 in the general formula (1), or “substituted or unsubstituted condensed hydrocarbon group”
  • phenanthryl group fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, Indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group Pyrazolyl group include dibenzofuranyl group, dibenzothienyl group, and carbolinyl group and the like. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R 11 to R 14 in the general formula (1), Specifically, deuterium atom, trifluoromethyl group, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, a linear or branched alkyl group having 1 to 6 carbon atoms such as n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group A linear or branched alkyloxy group having 1 to 6 carbon atoms such as ethyloxy group
  • aryloxy group in the “substituted or unsubstituted aryloxy group” represented by R 11 to R 14 in the general formula (1) include a phenyloxy group, a biphenylyloxy group, and a terphenyl group.
  • examples thereof include a tolyloxy group, a naphthyloxy group, an anthryloxy group, a phenanthryloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group.
  • These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • substituted aryloxy group represented by R 11 to R 14 in the general formula (1)
  • substituents include deuterium atom, trifluoromethyl group, cyano group, nitro group; fluorine Halogen atoms such as atoms, chlorine atoms, bromine atoms, iodine atoms; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, Linear or branched alkyl group having 1 to 6 carbon atoms such as neopentyl group and n-hexyl group; linear or branched alkyl group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group Alkyloxy groups; alkenyl groups such as allyl groups; a
  • the same groups as those mentioned for the “aromatic heterocyclic group” or “fused polycyclic aromatic group” can be mentioned.
  • substituent which these groups may have is also represented by the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensation” represented by B in the general formula (1).
  • the thing similar to what was shown regarding "substituent” of "polycyclic aromatic group” can be mention
  • the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 1 and Ar 2 in the general formula (1-1) is a thienyl group, a benzothienyl group, a benzothiazolyl group.
  • Sulfur-containing aromatic heterocyclic groups such as dibenzothienyl group, furyl group, pyranyl group, benzofuranyl group, benzoxazolyl group, dibenzofuranyl group and other oxygen-containing aromatic heterocycles, or carbazolyl group are preferable.
  • Ar 1 and Ar 2 in the general formula (1-1) are a “substituted or unsubstituted aromatic hydrocarbon group”, a “substituted or unsubstituted condensed polycyclic aromatic group”, or a carbazolyl group. Is preferred. Ar 1 and Ar 2 in the general formula (1-1) may be bonded directly or via respective substituents to form a ring. In this case, a single bond, a substituted or unsubstituted methylene group, Bonding is preferably via an oxygen atom or a sulfur atom, more preferably forming a ring via a substituted or unsubstituted methylene group.
  • Ar 1 and A in the general formula (1-1) may be bonded directly or via respective substituents to form a ring.
  • the bonding is preferably via an atom or a sulfur atom, more preferably a ring is formed through a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, and the ring is formed through a substituted or unsubstituted methylene group. It is particularly preferred to form.
  • the compound represented by the general formula (1) of the present invention which has an indenoacridan ring structure, is a novel compound, and has an excellent electron blocking ability than a conventional hole transport material, and an excellent amorphous And a thin film state is stable.
  • the compound having an indenoacridan ring structure represented by the general formula (1) of the present invention is a hole injection layer and / or a hole transport layer of an organic electroluminescence device (hereinafter abbreviated as an organic EL device). It can be used as a constituent material.
  • an organic EL device By using a material with higher hole injection properties, higher mobility, higher electron blocking properties, and higher electron stability than conventional materials, it is possible to confine excitons generated in the light emitting layer.
  • the probability of recombination of holes and electrons can be improved, high luminous efficiency can be obtained, the driving voltage is lowered, and the durability of the organic EL element is improved.
  • the compound having an indenoacridan ring structure represented by the general formula (1) of the present invention can also be used as a constituent material of an electron blocking layer of an organic EL device.
  • the driving voltage is lowered and current resistance is maintained while having high luminous efficiency. Is improved and the maximum light emission luminance of the organic EL element is improved.
  • the compound having an indenoacridan ring structure represented by the general formula (1) of the present invention can also be used as a constituent material of a light emitting layer of an organic EL device.
  • the material of the present invention which has excellent hole transportability compared to conventional materials and has a wide band gap, is used as a host material for the light-emitting layer, and supports a fluorescent or phosphorescent emitter called a dopant to emit light. By using it as a layer, it has the effect
  • the organic EL device of the present invention has a higher hole mobility than that of a conventional hole transport material, an excellent electron blocking ability, an excellent amorphous property, and a stable thin film state. Since a compound having a clidan ring structure is used, high efficiency and high durability can be realized.
  • the compound having an indenoacridan ring structure of the present invention is useful as a constituent material of a hole injection layer, a hole transport layer, an electron blocking layer or a light emitting layer of an organic EL device, and has an excellent electron blocking ability.
  • the amorphous property is good, the thin film state is stable, and the heat resistance is excellent.
  • the organic EL device of the present invention has high luminous efficiency and high power efficiency, which can reduce the practical driving voltage of the device. The emission start voltage can be lowered and the durability can be improved.
  • FIG. 1 is a 1 H-NMR chart of the compound of Example 1 of the present invention (Compound 2).
  • 2 is a 1 H-NMR chart of the compound of Example 2 of the present invention (Compound 19).
  • FIG. FIG. 3 is a 1 H-NMR chart of the compound of Example 3 of the present invention (Compound 30).
  • FIG. 3 is a 1 H-NMR chart of the compound of Example 4 of the present invention (Compound 31).
  • FIG. 6 is a 1 H-NMR chart of the compound of Example 5 of the present invention (Compound 32).
  • FIG. 6 is a 1 H-NMR chart of the compound of Example 6 of the present invention (Compound 33).
  • FIG. 6 is a 1 H-NMR chart of the compound of Example 7 of the present invention (Compound 34).
  • FIG. 3 is a diagram showing EL element configurations of Examples 10 to 16 and Comparative Example 1.
  • the compound having an indenoacridan ring structure of the present invention is a novel compound, and these compounds can be synthesized as follows, for example.
  • methyl 2- (9,9-dimethylfluoren-2-yl) aminobenzoate is synthesized by reaction of methyl 2-aminobenzoate with 9,9-dimethyl-2-iodofluorene, and methyl magnesium chloride
  • 2- ⁇ 2- (9,9-dimethylfluoren-2-yl) amino) phenyl ⁇ propan-2-ol was synthesized and subjected to a cyclization reaction, whereby 7,7,13,13 -Tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine can be synthesized.
  • a compound having an indenoacridan ring structure of the present invention in which the 5-position is substituted with an aryl group can be synthesized.
  • the introduction of a substituent to the indenoacridan ring can be achieved, for example, by bromination of the indenoacridan substituted with an aryl group at the 5-position with N-bromosuccinimide or the like at the 2-position.
  • Indenoacridan derivatives can be synthesized, and bromo-substituted products with different substitution positions can be obtained by changing the bromination reagent and conditions.
  • a compound having an indenoacridan ring structure of the present invention in which a substituent is introduced into the cridane ring can be synthesized.
  • Tg glass transition point
  • work function index of hole transportability
  • the glass transition point (Tg) was determined with a high sensitivity differential scanning calorimeter (Bruker AXS, DSC3100SA) using powder.
  • the work function was measured using an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) after forming a 100 nm thin film on the ITO substrate.
  • PYS-202 manufactured by Sumitomo Heavy Industries, Ltd.
  • the structure of the organic EL device of the present invention includes an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on the substrate, and between the anode and the hole transport layer. And those having an electron injection layer between the electron transport layer and the cathode.
  • these multilayer structures several organic layers can be omitted.
  • a structure having an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode sequentially on a substrate can be used. .
  • an electrode material having a large work function such as ITO or gold is used.
  • a hole injection layer of the organic EL device of the present invention in addition to a compound having an indenoacridan ring structure represented by the general formula (1) of the present invention, a porphyrin compound typified by copper phthalocyanine, a starburst type Materials such as triphenylamine derivatives and various triphenylamine tetramers, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • N, N′-diphenyl-N, N′-di (M-tolyl) benzidine (hereinafter abbreviated as TPD)
  • NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
  • NPD N, N, N ′
  • Benzidine derivatives such as N′-tetrabiphenylylbenzidine, 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine trimers and tetramers
  • TAPC 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS poly (styrene sulfonate)
  • a material that is usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony or the like, or a TPD structure having a partial structure. Molecular compounds and the like can be used.
  • Compounds can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • the light emitting layer of the organic EL device of the present invention various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, etc., in addition to metal complexes of quinolinol derivatives including Alq 3 Can be used.
  • the light-emitting layer may be composed of a host material and a dopant material.
  • the host material may be added to the light-emitting material.
  • Thiazole derivatives can be used as the dopant material.
  • quinacridone, coumarin, rubrene, perylene, and derivatives thereof benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • a phosphorescent material can be used as the light emitting material.
  • a phosphorescent emitter of a metal complex such as iridium or platinum can be used.
  • Green phosphorescent emitters such as Ir (ppy) 3
  • blue phosphorescent emitters such as FIrpic and FIr6, red phosphorescent emitters such as Btp 2 Ir (acac), and the like are used as host materials.
  • carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, mCP, etc.
  • a compound having an indenocarbazole ring structure represented can be used as a hole injection / transport host material.
  • a compound having an indenocarbazole ring structure represented can be used.
  • an electron transporting host material p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) can be used, and a high-performance organic EL device can be produced.
  • the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”).
  • BCP bathocuproine
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • various rare earth complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline, in addition to metal complexes of quinolinol derivatives including Alq 3 and BAlq.
  • Derivatives, phenanthroline derivatives, silole derivatives and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • an alkali metal salt such as lithium fluoride and cesium fluoride
  • an alkaline earth metal salt such as magnesium fluoride
  • a metal oxide such as aluminum oxide
  • an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
  • the glass transition point was calculated
  • the compound of the present invention has a glass transition point of 100 ° C. or higher, which indicates that the thin film state is stable in the compound of the present invention.
  • the compound of the present invention exhibits a suitable energy level as compared with the work function 5.54 eV of general hole transport materials such as NPD and TPD, and has a good hole transport capability.
  • the organic EL element has a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2 as shown in FIG. 6, an electron injection layer 7 and a cathode (aluminum electrode) 8 were deposited in this order.
  • the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, HIM-1 having the following structural formula was formed to a thickness of 20 nm as a hole injection layer 3 so as to cover the transparent anode 2. On this hole injection layer 3, the compound (compound 2) of Example 1 of the present invention was formed as a hole transport layer 4 so as to have a film thickness of 40 nm.
  • Binary vapor deposition was performed to form a film thickness of 30 nm.
  • this emitting layer 5 was formed to have the Alq 3 film thickness 30nm as an electron transport layer 6.
  • lithium fluoride was formed as the electron injection layer 7 so as to have a film thickness of 0.5 nm.
  • aluminum was deposited to a thickness of 150 nm to form the cathode 8.
  • the characteristic measurement was performed at normal temperature in air
  • Example 10 In Example 10, except that the compound (Compound 19) of Example 2 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 2) of Example 1 of the present invention as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 In Example 10, except that the compound (Compound 30) of Example 3 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 2) of Example 1 of the present invention as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 In Example 10, except that the compound (Compound 31) of Example 4 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 2) of Example 1 of the present invention as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 except that the compound of Example 5 of the present invention (Compound 32) was formed to a film thickness of 40 nm instead of the compound of Compound 1 of the present invention (Compound 2) as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 In Example 10, except that the compound (Compound 33) of Example 6 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 2) of Example 1 of the present invention as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 In Example 10, except that the compound (Compound 34) of Example 7 of the present invention was formed so as to have a film thickness of 40 nm instead of the compound (Compound 2) of Example 1 of the present invention as the material of the hole transport layer 4.
  • An organic EL element was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • Example 10 HTM-1 having the following structural formula was formed to a film thickness of 40 nm in place of the compound of Example 1 of the present invention (Compound 2) as the material of the hole transport layer 4.
  • Compound 2 the compound of Example 1 of the present invention
  • the driving voltage when a current density of 10 mA / cm 2 was passed was 5.17 V of the organic EL element using HTM-1, and that of Examples 1 to 7 of the present invention.
  • the organic EL device using the compound could be driven at a low voltage of 4.75 to 4.94V.
  • the organic EL element using the compounds of Examples 1 to 7 of the present invention is 6.30 to 7.5 compared to 5.49 lm / W of the organic EL element using HTM-1. Both were greatly improved at 18 lm / W. Further, both the luminance and the luminous efficiency were improved in the organic EL device using the compound of the present invention compared to the organic EL device using HTM-1.
  • the organic EL device using the compound having an indenoacridan ring structure of the present invention is more efficient than the known organic EL device using HTM-1. It was found that an improvement and a decrease in practical driving voltage can be achieved.
  • the compound having an indenoacridan ring structure of the present invention is excellent as a compound for an organic EL device because it has a high hole transport ability, an excellent electron blocking ability, an excellent amorphous property, and a stable thin film state. ing.
  • an organic EL device using the compound, high luminous efficiency and power efficiency can be obtained, practical driving voltage can be lowered, and durability can be improved. For example, it has become possible to develop home appliances and lighting.

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Abstract

Le problème décrit par la présente invention est de pourvoir à : un composé organique doté de propriétés caractéristiques telles que le composé organique peut manifester une excellente performance d'injection/de transport de trous et une excellente capacité à arrêter les électrons, est très stable quand il est converti sous la forme d'un film mince, et a une excellente résistance thermique, quand il est utilisé à titre de matériau pour un élément électroluminescent organique à haut rendement et durabilité élevée ; et un élément électroluminescent organique à haut rendement lumineux et durabilité élevée, qui est fabriqué à l'aide dudit composé. La solution selon l'invention porte sur un composé ayant une structure de cycle indéno-acridane, qui est représenté par la formule générale (1) ; et un élément électroluminescent organique comprenant une paire d'électrodes et une ou plusieurs couches organiques en sandwich entre les électrodes, ledit élément électroluminescent organique étant caractérisé en ce que le composé est utilisé à titre de matériau constitutif pour au moins une des couches organiques.
PCT/JP2014/000131 2013-01-17 2014-01-15 Composé ayant une structure de cycle indéno-acridane, et élément électroluminescent organique WO2014112360A1 (fr)

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WO2016027687A1 (fr) * 2014-08-20 2016-02-25 保土谷化学工業株式会社 Élément électroluminescent organique
CN109844978A (zh) * 2016-10-19 2019-06-04 保土谷化学工业株式会社 茚并咔唑化合物及有机电致发光元件

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