WO2009107596A1 - Milieu luminescent organique et élément el organique - Google Patents

Milieu luminescent organique et élément el organique Download PDF

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WO2009107596A1
WO2009107596A1 PCT/JP2009/053247 JP2009053247W WO2009107596A1 WO 2009107596 A1 WO2009107596 A1 WO 2009107596A1 JP 2009053247 W JP2009053247 W JP 2009053247W WO 2009107596 A1 WO2009107596 A1 WO 2009107596A1
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group
substituted
unsubstituted
carbon atoms
formula
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PCT/JP2009/053247
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正和 舟橋
昌宏 河村
光則 伊藤
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • H—ELECTRICITY
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene

Definitions

  • the present invention relates to an organic light emitting medium and an organic EL element using the same.
  • an organic EL element (organic electroluminescence element) using light emission of an organic compound.
  • the organic EL element has a plurality of organic thin films stacked between an anode and a cathode.
  • a voltage is applied between the anode and the cathode, holes and electrons are injected into the organic thin film from the anode and the cathode, respectively.
  • Excited molecules are generated in the light emitting layer in the organic thin film by the injected holes and electrons. Then, energy when returning from the excited state to the ground state is emitted as light.
  • Patent Document 1 discloses a combination of an anthracene host and an arylamine.
  • Patent Documents 2 to 4 disclose a combination of an anthracene host having a specific structure and a diaminopyrene dopant.
  • Patent Documents 5 and 6 disclose anthracene-based host materials.
  • WO 2004/018588 WO2004 / 018587 JP 2004-204238 A WO2005 / 108348 publication WO2005 / 054162 publication WO2005 / 061656
  • An object of the present invention is to provide an organic EL element including a combination of a specific host material and a dopant material capable of realizing short-wavelength light emission and long-lifetime blue light emission and high-efficiency and long-lifetime green light emission.
  • An organic light-emitting medium that can be used for an organic thin film layer of an EL element is provided.
  • Another object of the present invention is to use an organic EL element including a combination of a specific host material and a dopant material, which can obtain high luminous efficiency and has a long lifetime, and an organic thin film layer of the organic EL element. It is to provide an organic light-emitting medium that can be used.
  • the present inventors have found that the following problems can be solved by the present invention. According to the present invention, the following organic light emitting media and the like are provided.
  • R 21 to R 24 each independently represents a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted
  • R 21 to R 24 each independently represents a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted
  • a substituted cycloalkyl group having 3 to 50 carbon atoms or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms and one or two pairs of adjacent alkyl groups on the same benzene ring The adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group, provided that the adjacent alkyl group forms a 1-naphthyl group together
  • n1 to n4 are each independently an integer of 0 to 5.
  • R a and R b are each independently a hydrogen atom, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nucleus, A cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted nucleus having 6 to 50 carbon atoms An aryloxy group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
  • R a and R b are hydrogen atoms at the same time.
  • Ar 11 and Ar 12 are each independently a substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms
  • R 1 to R 8 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted group
  • Ar 11 and Ar 12 when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group, the other is not a 4- (1-naphthyl) phenyl-1-yl group. Further, at least one of Ar 11 and Ar 12 is not a substituted or unsubstituted anthryl group.
  • An organic light-emitting medium comprising a diaminopyrene derivative represented by the following formula (1) ′ and an anthracene derivative represented by the following formula (2) ′.
  • R 21 ′ to R 24 ′ each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted 1 to 50 carbon atoms, An alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or a substituted or unsubstituted silyl group having 3 to 20 carbon atoms, When there are one or two sets of adjacent alkyl groups on the same benzene ring, the adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group.
  • n1 ′ to n4 ′ are each independently an integer of 1 to 5.
  • R a ′ and R b ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.
  • Ar 11 ′ and Ar 12 ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms
  • R 1 ′ to R 8 ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy
  • R 1 ′ to R 8 ′ are hydrogen atoms and one of Ar 11 ′ and Ar 12 ′ is an unsubstituted 2-naphthyl group, the other is 4- (1-naphthyl) phenyl-1- It is not an ill group. )
  • An organic electroluminescence device comprising an anode, a cathode, and one or more organic thin film layers between the anode and the cathode, wherein at least one of the organic thin film layers contains the organic light emitting medium.
  • an organic EL element including a combination of a specific host material and a dopant material capable of realizing short-wavelength light emission and long-lifetime blue light emission, and high-efficiency and long-lifetime green light emission, and the organic An organic light-emitting medium that can be used for an organic thin film layer of an EL element can be provided. According to the present invention, it is possible to provide an organic EL element that can obtain high luminous efficiency and has a long lifetime, and an organic light emitting medium that can be used for an organic thin film layer of the organic EL element.
  • the organic light-emitting medium of the present invention includes the organic light-emitting medium I and the organic light-emitting medium II, each including a specific diaminopyrene derivative and a specific anthracene derivative.
  • the organic light-emitting medium contributes to light emission as a constituent component of the organic thin film layer of the organic EL element, and is present in the layer as, for example, a deposit.
  • the organic light emitting medium I can emit light of a short wavelength including blue light emission with high color purity, contributes to a long life, or obtains high light emission efficiency. it can.
  • the organic light emitting medium II can realize a green organic EL element having a high light emission rate and a long lifetime.
  • the organic light emitting media I and II will be described.
  • nuclear carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • nuclear atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • the substituent in “substituted or unsubstituted...” Is an alkyl group, aryl group, cycloalkyl group, alkoxy group, heterocyclic group, aralkyl group as described later.
  • Organic luminescent medium I includes a diaminopyrene derivative according to the present invention represented by the following formula (1) and an anthracene derivative represented by the following formula (2).
  • the diaminopyrene derivative according to the organic light-emitting medium I is represented by the following formula (1).
  • R 21 to R 24 are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted group.
  • cycloalkyl group is a cycloalkyl group having 3 to 50 nuclear carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and one or two adjacent alkyl groups are present on the same benzene ring
  • Adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group, provided that the adjacent alkyl group forms a 1-naphthyl group together with the benzene ring to which they are bonded.
  • n1 to n4 are each independently an integer of 0 to 5.
  • R a and R b are each independently a hydrogen atom, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted nucleus, A cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted nucleus having 6 to 50 carbon atoms An aryloxy group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group. However, it excludes when R a and R b are hydrogen atoms at the same time.
  • R a and R b are preferably an alkyl group or a cycloalkyl group.
  • the alkyl group is more preferably an alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, or a t-butyl group.
  • the cycloalkyl group is more preferably a cycloalkyl group having 3 to 6 carbon atoms, such as a cyclopropanyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • Examples of the substituted or unsubstituted aryl group represented by R 21 to R 24 include a phenyl group, a methylphenyl group, an ethylphenyl group, a biphenyl group, a cyclopentylphenyl group, a cyclohexylphenyl group, a methylbiphenyl group, an ethylbiphenyl group, and a cyclopentylphenyl.
  • Examples of the substituted or unsubstituted alkyl group of R 21 to R 24 include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl Group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, and the like.
  • Preferred are methyl group, ethyl group, propyl group, and tert-butyl group.
  • the adjacent alkyl groups are bonded to each other to form a substituted or unsubstituted divalent saturated or unsubstituted group.
  • a saturated linking group may be formed.
  • A, D, E, G and J are —CH 2 —, —CR 50 R 51 — (R 50 and R 51 each represent a substituent), —O—, —S—, — N- or -CO- a to h each represents an integer of 1 to 10;
  • R 50 and R 51 each represent a substituent
  • —O—, —S—, — N- or -CO- a to h each represents an integer of 1 to 10;
  • a, b, c, g, and h are 2 or more, a plurality of A, D, E, G, and J may be the same or different.
  • a to c are each preferably 5 or 6
  • d to f are each preferably 2
  • g and h are each preferably 1.
  • the substituent for R 50 and R 51 is preferably a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a nucleus having 6 to 14 carbon atoms.
  • the substituent formed by the bonding group and the benzene ring directly bonded to the nitrogen atom is more preferably a ring having the following structure.
  • Examples of the cycloalkyl group represented by R 21 to R 24 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a bicycloheptyl group, a bicyclooctyl group, and a tricycloheptyl group.
  • Examples of the substituted or unsubstituted aralkyl group of R 21 to R 24 include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ - Naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl group, m
  • R a and R b examples include the same as R 1 to R 8 in the formula (2) described later.
  • the diaminopyrene derivative of the formula (1) is represented by the following formula.
  • R 21 to R 24 , R a and R b are the same as described above.
  • R 21 to R 24 may be the same or different from each other, but it is preferable that R 21 and R 23 , and R 22 and R 24 are the same.
  • R a and R b may be the same or different, but are preferably the same.
  • diaminopyrene derivative represented by the formula (1) include compounds represented by the following formula.
  • An anthracene derivative according to the organic light-emitting medium I is represented by the following formula (2).
  • Ar 11 and Ar 12 are each independently a substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms
  • R 1 to R 8 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted group
  • Ar 11 and Ar 12 when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group, the other is not a 4- (1-naphthyl) phenyl-1-yl group. Further, at least one of Ar 11 and Ar 12 is not a substituted or unsubstituted anthryl group.
  • anthracene derivative represented by the formula (2) preferably when one of Ar 11 and Ar 12 is an unsubstituted 2-naphthyl group, the other is not an aryl-substituted phenyl group.
  • the anthracene derivative according to the present invention is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected depending on the configuration of the organic EL element to be applied and the required characteristics.
  • Ar 11 and Ar 12 in the formula (2) are each independently a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.
  • the anthracene derivative can be classified into a case where Ar 11 and Ar 12 are the same substituted or unsubstituted condensed aryl group and a case where they are different substituted or unsubstituted condensed aryl groups.
  • anthracene derivatives represented by the following formulas (2-1) to (2-3) and anthracene derivatives in which Ar 11 and Ar 12 in formula (2) are different substituted or unsubstituted condensed aryl groups Is mentioned.
  • Ar 11 and Ar 12 are substituted or unsubstituted 9-phenanthrenyl groups.
  • R 1 to R 8 are the same as above, R 11 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • Ar 11 and Ar 12 in the formula (2) are substituted or unsubstituted 2-naphthyl groups.
  • R 1 to R 8 and R 11 are the same as above, b is an integer of 1 to 7.
  • b is an integer of 2 or more, a plurality of R 11 may be the same or different on condition that two substituted or unsubstituted 2-naphthyl groups are the same.
  • Ar 11 and Ar 12 in the formula (2) are substituted or unsubstituted 1-naphthyl groups.
  • R 1 to R 8 , R 11 and b are the same as described above.
  • b is an integer of 2 or more, a plurality of R 11 are two substituted or unsubstituted. Each may be the same or different, provided that the 1-naphthyl groups are the same.
  • Examples of the anthracene derivative in which Ar 11 and Ar 12 in Formula (2) are different substituted or unsubstituted condensed aryl groups include a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, and substituted or unsubstituted It is preferably any one of unsubstituted 2-naphthyl groups.
  • Ar 11 is a 1-naphthyl group and Ar 12 is a 2-naphthyl group
  • Ar 11 is a 1-naphthyl group and Ar 12 is a 9-phenanthryl group
  • Ar 11 is 2- This is the case where the naphthyl group and Ar 12 are a 9-phenanthryl group.
  • anthracene derivative (B) In the anthracene derivative, one of Ar 11 and Ar 12 in Formula (2) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 20 nuclear carbon atoms.
  • Specific examples of the anthracene derivative include anthracene derivatives represented by the following formulas (2-4) and (2-5).
  • Ar 11 in the formula (2) is a substituted or unsubstituted 1-naphthyl group
  • Ar 12 is a substituted or unsubstituted phenyl group.
  • Ar 6 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Or an unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a 9,9-dimethylfluoren-1-yl group, or a 9,9-dimethylfluorene-2- Yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group, dibenzofuran-3
  • Ar 6 may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar 6 is bonded.
  • b is an integer of 2 or more, the plurality of R 11 may be the same or different.
  • Ar 11 in the formula (2) is a substituted or unsubstituted 2-naphthyl group
  • Ar 12 is a substituted or unsubstituted phenyl group .
  • Ar 7 is a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted group Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a dibenzofuran-1-yl group, a dibenzofuran-2-yl group, a dibenzofuran-3-yl group, or a dibenzofuran-4-yl group.
  • Ar 7 may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar 7 is bonded.
  • b is an integer of 2 or more
  • the plurality of R 11 may be the same or different.
  • Ar 7 excludes the case where 4- (1-naphthyl) phenyl-1-yl group is formed with the adjacent phenylene group.
  • the anthracene derivative is represented by the following formula (2-6), specifically, any one of the following formulas (2-6-1), (2-6-2), and (2-6-3) It is preferable that it is a derivative represented.
  • R 1 to R 8 and Ar 6 are the same as above,
  • Ar 5 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Alternatively, it is an unsubstituted aralkyl group having 7 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and Ar 5 and Ar 6 are each independently selected.
  • Examples of the substituted or unsubstituted aryl group having 6 to 20 nuclear carbon atoms of Ar 11 and Ar 12 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, and a 9-anthryl group.
  • a substituted phenyl group and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms for example, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group.
  • Ar 5a , Ar 6a and Ar 8 substituted or unsubstituted condensed aryl groups having 10 to 20 nuclear carbon atoms include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9 -Anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group and the like can be mentioned.
  • a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.
  • Examples of the substituted or unsubstituted aryl group having 6 to 50 carbon atoms of R 1 to R 8 , R 11 , Ar 5 and Ar 6 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, 2 -Anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1 -Pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl Group, p-terpheny
  • Examples of the substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms of R 1 to R 8 , R 11 and Ar 5 to Ar 7 include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group 3-benzofuranyl group, 4-benzofuranyl group
  • Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R 1 to R 8 , R 11 and Ar 5 to Ar 7 include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s- Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxy Isobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-d
  • Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms of the substituents R 1 to R 8 , R 11 and Ar 5 to Ar 7 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, 4 -Methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
  • the substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R 1 to R 8 and R 11 is a group represented by —OZ, and Z is the substituted or unsubstituted carbon number of R 1 to R 8. Selected from 1 to 50 alkyl groups.
  • the substituted or unsubstituted aryloxy group having 6 to 50 nuclear carbon atoms of R 1 to R 8 and R 11 is represented as —OY, and Y represents the substituted or unsubstituted nuclear carbon number of the above R 1 to R 8. Selected from 6 to 50 aryl groups.
  • the substituted or unsubstituted arylthio group having 6 to 50 nuclear carbon atoms represented by R 11 is represented by —SY, and Y represents the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms represented by R 1 to R 8. To be elected.
  • the substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms of R 11 (the alkyl part has 1 to 49 carbon atoms) is represented as —COOZ, and Z is the substituted or unsubstituted carbon number of R 1 to R 8. It is selected from 1 to 49 alkyl groups.
  • Examples of the substituted silyl group of R 1 to R 8 and R 11 include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.
  • halogen atoms for R 1 to R 8 and R 11 include fluorine, chlorine, bromine, iodine and the like.
  • R 1 to R 8 are hydrogen atoms.
  • anthracene derivative represented by the formula (2) include derivatives represented by the following formula.
  • the diaminopyrene derivative represented by the formula (1) is, for example, introduced into a dibromopyrene obtained by bromination of commercially available pyrene by a known method, then brominated again, and correspondingly reacted under a metal catalyst. It can be synthesized by reacting with a secondary amine compound.
  • the anthracene derivative represented by Formula (2) is compoundable by the method of WO2004 / 018587, for example.
  • the organic light-emitting medium of the present invention is in a state in which the anthracene derivative represented by the diaminopyrene derivative represented by the formula (1) as described above coexists.
  • the mass ratio of the diaminopyrene derivative represented by the formula (1) and the anthracene derivative represented by the formula (2) is preferably 50:50 to 0.1: 99.9, and 20:80 to 1 : 99 is more preferable.
  • Organic light emitting medium II includes a diaminopyrene derivative according to the present invention represented by the following formula (1) ′ and an anthracene derivative represented by the following formula (2) ′.
  • the diaminopyrene derivative according to the organic light emitting medium II is represented by the following formula (1) ′.
  • R 21 ′ to R 24 ′ each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the adjacent alkyl groups may be bonded to each other to form a substituted or unsubstituted divalent linking group.
  • n1 ′ to n4 ′ are each independently an integer of 1 to 5.
  • R a ′ and R b ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms.
  • Examples of the substituted or unsubstituted aryl group and substituted or unsubstituted alkyl group having 6 to 50 nuclear carbon atoms of R 21 ′ to R 24 ′ are the same as those of R 21 to R 24 in the above formula (1). is there.
  • the adjacent alkyl groups are bonded to each other to form a substituted or unsubstituted divalent saturated or unsubstituted group.
  • a saturated linking group may be formed.
  • A, D, E, G and J are —CH 2 —, —CR 50 R 51 — (R 50 and R 51 each represent a substituent), —O—, —S—, — N- or -CO- a to h each represents an integer of 1 to 10;
  • R 50 and R 51 each represent a substituent
  • —O—, —S—, — N- or -CO- a to h each represents an integer of 1 to 10;
  • a, b, c, g, and h are 2 or more, a plurality of A, D, E, G, and J may be the same or different.
  • a to c are each preferably 5 or 6
  • d to f are each preferably 2
  • g and h are each preferably 1.
  • the substituent for R 50 and R 51 is preferably a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a nucleus having 6 to 14 carbon atoms.
  • the substituent formed by the bonding group and the benzene ring directly bonded to the nitrogen atom is more preferably a ring having the following structure.
  • R 21 ' ⁇ R 24' in R 21 ' ⁇ R 24' are the same as those of R 21 ⁇ R 24 in the formula (1).
  • R 21 ′ to R 24 ′ are preferably a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t-butyl group, substituted or unsubstituted An unsubstituted cyclohexyl group, or a substituted or unsubstituted trimethylsilyl group.
  • the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms of R a ′ and R b ′ is defined as “substituted or unsubstituted nuclear carbon atoms of 6 to 50 defined by R 11 in formula (2) ′ described later. And is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
  • the diaminopyrene derivative of the formula (1) ′ is represented by the following formula.
  • R 21 ′ to R 24 ′ , R a ′ and R b ′ are the same as described above.
  • R 21 ′ to R 24 ′ may be the same or different, but it is preferable that R 21 ′ and R 23 ′ and R 22 ′ and R 24 ′ are the same.
  • R a ′ and R b ′ may be the same or different, but are preferably the same.
  • diaminopyrene derivative represented by the formula (1) ′ include compounds represented by the following formula.
  • An anthracene derivative according to the organic light-emitting medium II is represented by the following formula (2) ′.
  • Ar 11 ′ and Ar 12 ′ are each independently a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms or a heterocyclic group having 5 to 50 nuclear atoms
  • R 1 ′ to R 8 ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, substituted or unsubstituted
  • anthracene derivative of the present invention preferably, when one of Ar 11 ′ and Ar 12 ′ is an unsubstituted 2-naphthyl group, the other is not an aryl-substituted phenyl group.
  • the anthracene derivative according to the present invention is preferably any of the following anthracene derivatives (A) ′, (B) ′, and (C) ′, and is selected depending on the configuration of the organic EL element to be applied and the required characteristics.
  • Ar 11 ′ and Ar 12 ′ in the formula (2) ′ are each independently a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms.
  • the anthracene derivative can be classified into a case where Ar 11 ′ and Ar 12 ′ are the same substituted or unsubstituted condensed aryl group and a case where they are different substituted or unsubstituted condensed aryl groups.
  • anthracene derivatives represented by the following formulas (2-1) ′ to (2-3) ′, and substituted or unsubstituted condensed aryl in which Ar 11 ′ and Ar 12 ′ in formula (2) ′ are different And anthracene derivatives as groups.
  • Ar 11 ′ and Ar 12 ′ are substituted or unsubstituted 9-phenanthrenyl groups.
  • R 1 ′ to R 8 ′ are the same as above, R 11 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • Ar 11 ′ and Ar 12 ′ in the formula (2) ′ are substituted or unsubstituted 2-naphthyl groups.
  • R 1 ′ to R 8 ′ and R 11 are the same as above, b is an integer of 1 to 7.
  • a plurality of R 11 may be the same or different on condition that two substituted or unsubstituted 2-naphthyl groups are the same.
  • Ar 11 ′ and Ar 12 ′ in the formula (2) ′ are substituted or unsubstituted 1-naphthyl groups.
  • R 1 ′ to R 8 ′ , R 11 and b are the same as those described above.
  • b is an integer of 2 or more, a plurality of R 11 are substituted with two substituents or Each may be the same or different, provided that the unsubstituted 1-naphthyl groups are the same.
  • Ar 11 ′ and Ar 12 ′ in the formula (2) ′ are the same substituted or unsubstituted fluoranthenyl group.
  • an anthracene derivative in which Ar 11 ′ and Ar 12 ′ in the formula (2) ′ are the same substituted or unsubstituted pyrenyl group are also preferable.
  • Ar 11 ′ and Ar 12 ′ in formula (2) ′ are different substituted or unsubstituted condensed aryl groups
  • Ar 11 ′ and Ar 12 ′ are represented by formulas (2-1) ′ to (2- 3) ′, a substituted or unsubstituted 9-phenanthrenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, and a substituted or unsubstituted fluoranthenyl group Is preferred.
  • Ar 11 ′ is a 1-naphthyl group and Ar 12 ′ is a 2-naphthyl group
  • Ar 11 ′ is a 1-naphthyl group and Ar 12 ′ is a 9-phenanthryl group
  • Ar This is the case where 11 ′ is a 2-naphthyl group and Ar 12 ′ is a 9-phenanthryl group.
  • anthracene derivative (B) ') In the anthracene derivative, one of Ar 11 ′ and Ar 12 ′ in the formula (2) ′ is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted condensed aryl group having 10 to 50 nuclear carbon atoms. ing. Specific examples of the anthracene derivative include anthracene derivatives represented by the following formulas (2-4) ′ and (2-5) ′.
  • Ar 11 ′ in the formula (2) ′ is a substituted or unsubstituted 1-naphthyl group
  • Ar 12 ′ is a substituted or unsubstituted phenyl group. It has become.
  • Ar 6 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Or an unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a 9,9-dimethylfluoren-1-yl group, or a 9,9-dimethylfluorene-2- Yl group, 9,9-dimethylfluoren-3-yl group, 9,9-dimethylfluoren-4-yl group, dibenzofuran-1-yl group, dibenzofuran-2-yl group
  • Ar 6 may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar 6 is bonded.
  • b is an integer of 2 or more, the plurality of R 11 may be the same or different.
  • Ar 11 ′ in the formula (2) ′ is a substituted or unsubstituted 2-naphthyl group
  • Ar 12 ′ is a substituted or unsubstituted phenyl group. It has become.
  • Ar 7 is a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted group Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 nucleus atoms, a dibenzofuran-1-yl group, a dibenzofuran-2-yl group, a dibenzofuran-3-yl group, or a dibenzofuran-4-yl group.
  • Ar 7 may form a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted dibenzofluorenyl group together with the benzene ring to which Ar 7 is bonded.
  • b is an integer of 2 or more
  • the plurality of R 11 may be the same or different.
  • Ar 7 excludes the case where 4- (1-naphthyl) phenyl-1-yl group is formed with the adjacent phenylene group.
  • Ar 11 ′ in the formula (2) ′ is a substituted or unsubstituted fluoranthenyl group
  • Ar Anthracene derivatives in which 12 ′ is a substituted or unsubstituted phenyl group are also preferable.
  • the anthracene derivative is represented by the following formula (2-6) ′, specifically, the following formulas (2-6-1) ′, (2-6-2) ′ and (2-6-3) ′. It is preferable that it is a derivative represented by either.
  • Ar 5 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, a substituted group Alternatively, it is an unsubstituted aralkyl group having 7 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and Ar 5 and Ar 6 are each independently selected.
  • substituted or unsubstituted aryl groups having 6 to 50 nuclear carbon atoms of R 11 , Ar 5 and Ar 6 , Ar 11 ′ and Ar 12 ′ are the same as those of Ar 11 and Ar 12 in the above formula (2). It is.
  • an unsubstituted phenyl group, a substituted phenyl group, and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms eg, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group
  • fused aryl groups Ar 5a, Ar 6a and substituted or unsubstituted C 10 -C 20 Ar 8 is the same as this of Ar 5a, Ar 6a and Ar 8 in the formula (2) .
  • 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, pyrenyl group (1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group), and fluorenyl group (2-fluorenyl group) are preferable.
  • Examples of the heterocyclic group of R 11 and Ar 5 ⁇ substituted or unsubstituted 5 to 50 ring atoms of Ar 7, this of R 1 ⁇ R 8, R 11 and Ar 5 ⁇ Ar 7 in the above formula (2) Is the same.
  • Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R 1 ′ to R 8 ′ , R 11 and Ar 5 to Ar 7 include R 1 to R 8 , R 11 and Ar in the above formula (2). This is the same as 5 to Ar 7 .
  • Preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group and t-butyl group.
  • Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms of the substituents R 1 ′ to R 8 ′ , R 11 and Ar 5 to Ar 7 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like. Preferably, they are a cyclopentyl group and a cyclohexyl group.
  • the substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R 1 ′ to R 8 ′ and R 11 is a group represented by —OZ, and Z is the substituted or unsubstituted group of R 1 ′ to R 8 ′. It is selected from substituted alkyl groups having 1 to 50 carbon atoms.
  • R 1 ′ to R 8 ′ , R 11 and Ar 5 to Ar 7 substituted or unsubstituted C 7-50 aralkyl groups (the aryl moiety has 6 to 49 carbon atoms, the alkyl moiety has 1 to 44 carbon atoms) ) are the same as those of R 1 to R 8 , R 11 and Ar 5 to Ar 7 in the above formula (2).
  • the substituted or unsubstituted aryloxy group and arylthio group having 6 to 50 nuclear carbon atoms of R 1 ′ to R 8 ′ and R 11 are represented by —OY and —SY, respectively, and Y represents the above R 1 ′ to R It is selected from 8 ' substituted or unsubstituted aryl groups having 6 to 50 nuclear carbon atoms.
  • a substituted or unsubstituted alkoxy group having 2 to 50 carbon atoms (the alkyl moiety has 1 to 49 carbon atoms) of R 1 ′ to R 8 ′ and R 11 is represented as —COOZ, and Z represents the above R 1 ′ to R It is selected from 8 ' substituted or unsubstituted alkyl groups having 1 to 49 carbon atoms.
  • Examples of the substituted silyl group of R 1 ′ to R 8 ′ and R 11 include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triphenylsilyl group.
  • halogen atoms for R 1 ′ to R 8 ′ and R 11 include fluorine, chlorine, bromine and iodine.
  • anthracene derivative represented by the formula (2) ′ of the present invention include the following.
  • the diaminopyrene derivative represented by the formula (1) ′ is prepared by, for example, introducing a substituent into dibromopyrene obtained by bromination of commercially available pyrene by a known method, and then brominating it again under a metal catalyst. Can be synthesized by reacting with a secondary amine compound.
  • the anthracene derivative represented by the formula (2) ′ can be synthesized, for example, by the method described in WO 2004/018585.
  • the organic light-emitting medium of the present invention is in a state where an anthracene derivative represented by the diaminopyrene derivative formula (2) ′ represented by the formula (1) ′ as described above coexists.
  • the mass ratio of the diaminopyrene derivative represented by the formula (1) ′ and the anthracene derivative represented by the formula (2) ′ is preferably 50:50 to 0.1: 99.9, and 20:80 More preferably, it is ⁇ 1: 99.
  • the organic EL device of the present invention is a device in which one or more organic thin film layers are formed between an anode and a cathode.
  • the organic thin film layer is a plurality of layers, one layer is a light emitting layer.
  • a light emitting layer as an organic thin film layer is formed between the anode and the cathode.
  • At least one of the organic thin film layers contains the organic light emitting medium of the present invention, and in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material. Further, a hole injection material or an electron injection material may be contained.
  • at least one layer (preferably light emitting layer) of the organic thin film layers may be formed from the organic light emitting medium of the present invention.
  • the organic light emitting medium of the present invention has high light emission characteristics.
  • the organic EL device of the present invention is an organic EL device in which an organic thin film layer comprising at least two layers including at least a light emitting layer is sandwiched between a cathode and an anode, and the organic EL device of the present invention is interposed between the anode and the light emitting layer. It is also preferable to have an organic layer whose main component is a luminescent medium. Examples of the organic layer include a hole injection layer and a hole transport layer.
  • organic EL elements having a plurality of organic thin film layers are (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole). (Injection layer / light emitting layer / electron injection layer / cathode) and the like.
  • organic light-emitting medium of the present invention further known light-emitting materials, doping materials, hole-injecting materials, and electron-injecting materials can be used for the multiple layers as needed.
  • the organic EL element can prevent the brightness
  • a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission.
  • the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call.
  • an electron injection layer a layer that injects electrons from an electrode is referred to as an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
  • an electron injection layer a layer that injects electrons from an electrode
  • an electron transport layer a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer.
  • Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
  • Examples of host materials or doping materials that can be used in the light emitting layer together with the organic light emitting medium of the present invention include, for example, naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentaene.
  • Condensed polyaromatic compounds such as pentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and the like
  • organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinato) aluminum, triarylamine derivatives, styrylamido Derivatives, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid ester derivatives, diketopyrrolopyrrole derivatives, acridone derivatives,
  • a hole injection material As a hole injection material, it has the ability to transport holes, has a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or organic light emitting medium, and excitons generated in the light emitting layer
  • the compound which prevents the movement to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable.
  • phthalocyanine derivatives naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl Examples include alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers. However, it is not limited to these.
  • more effective hole injection materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
  • aromatic tertiary amine derivative include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4 '-Diamine, N, N, N', N '-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N', N '-(4-methylphenyl) ) -1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-( Methylpheny
  • phthalocyanine (Pc) derivative examples include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as VOPc, TiOPc, MoOPc, and GaPc—O—GaPc.
  • the organic EL device of the present invention includes a layer containing these aromatic tertiary amine derivatives and / or phthalocyanine derivatives, for example, the hole transport layer or the hole injection layer, between the light emitting layer and the anode. Preferably formed.
  • an electron injection material it has the ability to transport electrons, has an electron injection effect from the cathode, and an excellent electron injection effect for the light emitting layer or light emitting material.
  • the compound which prevents the movement to and is excellent in thin film forming ability is preferable.
  • 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable.
  • a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), such as tris (8-quinolinolato) aluminum, is injected. It can be used as a material.
  • examples of the oxadiazole derivative include electron transfer compounds represented by the following general formula.
  • Ar 1 , Ar 2 , Ar 3 , Ar 5 , Ar 6 , and Ar 9 each represent a substituted or unsubstituted aryl group, and may be the same or different from each other.
  • Ar 4 , Ar 7 and Ar 8 represent a substituted or unsubstituted arylene group, and may be the same or different.
  • examples of the aryl group include a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
  • examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
  • examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
  • This electron transfer compound is preferably a thin film-forming compound.
  • electron transfer compound examples include the following. Me represents methyl and tBu represents tbutyl.
  • materials represented by the following general formulas (A) to (F) can also be used as the electron injection material.
  • a 1 to A 3 are each independently a nitrogen atom or a carbon atom.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms
  • Ar 2 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • any one of Ar 1 and Ar 2 is a substituted or unsubstituted condensed ring group having 10 to 60 nuclear carbon atoms, or a substituted or unsubstituted monoheterocondensed ring group having 5 to 60 nucleus atoms.
  • L 1 , L 2 and L are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, or a substituted or unsubstituted An unsubstituted fluorenylene group.
  • R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R 1 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or —L 1 —Ar 1 —Ar 2 The nitrogen-containing heterocyclic derivative represented by this.
  • HAr-L-Ar 1 -Ar 2 (Wherein HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent, L has a single bond, an arylene group having 6 to 60 nuclear carbon atoms which may have a substituent, a heteroarylene group having 5 to 60 nuclear atoms which may have a substituent, or a substituent.
  • a fluorenylene group which may be Ar 1 is an optionally substituted divalent aromatic hydrocarbon group having 6 to 60 nuclear carbon atoms
  • Ar 2 is an aryl group having 6 to 60 nuclear carbon atoms which may have a substituent or a heterocyclic group having 5 to 60 nuclear atoms which may have a substituent.
  • X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, alkoxy group, alkenyloxy group, alkynyloxy group, hydroxy group, substituted or unsubstituted aryl group, substituted Or an unsubstituted heterocyclic ring or a structure in which X and Y are combined to form a saturated or unsaturated ring
  • R 1 to R 4 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, Alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group
  • R 1 to R 8 and Z 2 are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, or an alkoxy group.
  • an aryloxy group, X, Y and Z 1 each independently represent a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group;
  • the substituents of Z 1 and Z 2 may be bonded to each other to form a condensed ring.
  • N represents an integer of 1 to 3, and when n is 2 or more, Z 1 may be different.
  • Q 1 and Q 2 each independently represent a ligand represented by the following general formula (G)
  • L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, —OR 1 (R 1 is a hydrogen atom, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group) or —O—Ga—Q 3 (Q 4 ) (Q 3 and Q 4 are the same as Q 1 and Q 2 ).
  • rings A 1 and A 2 are 6-membered aryl ring structures condensed with each other which may have a substituent.
  • This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.
  • substituents of the rings A 1 and A 2 forming the ligand of the general formula (G) include chlorine, bromine, iodine, halogen atoms of fluorine, methyl group, ethyl group, propyl group, Substituted or unsubstituted alkyl groups such as butyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group, phenyl group, naphthyl group, 3-methyl A substituted or unsubstituted aryl group such as phenyl group, 3-methoxyphenyl group, 3-fluorophenyl group, 3-trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitrophenyl group, methoxy group, n- Butoxy group, t-butoxy group, trichlor
  • the organic EL device of the present invention include a device containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer.
  • the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals.
  • preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV).
  • a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. .
  • alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element.
  • a combination of two or more alkali metals is also preferable.
  • a combination containing Cs such as Cs and Na, Cs and K, Cs and Rb, or Cs. And a combination of Na and K.
  • Cs such as Cs and Na, Cs and K, Cs and Rb, or Cs.
  • Na and K a combination of Na and K.
  • an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented and the electron injection property can be improved.
  • an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
  • preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
  • preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe
  • preferable alkali metal halides include, for example, LiF, NaF, KF, CsF, LiCl, KCl, and NaCl.
  • preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
  • the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.
  • a cathode what uses a metal, an alloy, an electroconductive compound, and a mixture thereof with a small work function (4 eV or less) as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, cesium, magnesium / silver alloy, aluminum / aluminum oxide, Al / Li 2 O, Al / LiO, Al / LiF, aluminum Examples include lithium alloys, indium, and rare earth metals.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the transmittance of the light emitted from the cathode is larger than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • an organic EL element applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leakage or short circuit.
  • an insulating thin film layer may be inserted between the pair of electrodes.
  • Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.
  • a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Further, palladium, etc. and alloys thereof, ITO (indium tin oxide) substrate, tin oxide used for NESA substrate, metal oxide such as indium oxide, and organic conductive resin such as polythiophene and polypyrrole are used.
  • Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these.
  • Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.
  • the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the light emission wavelength region of the device.
  • the substrate is also preferably transparent.
  • the transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering.
  • the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
  • the substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
  • Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone.
  • each layer of the organic EL device for the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to.
  • the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
  • an appropriate resin or additive may be used for improving film formability and preventing pinholes in the film.
  • Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole.
  • the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
  • the material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.
  • Example 1 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the glass substrate with the transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and first, a compound A-1 having a film thickness of 60 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. Was deposited. Subsequent to the formation of the A-1 film, A-2 having a thickness of 20 nm was formed on the A-1 film. Further, the host material EM1 and the dopant material DM7-4 of the present invention were formed on the A-2 film at a film thickness ratio of 40: 2 to form a blue light emitting layer.
  • Alq having a thickness of 20 nm was deposited as an electron transport layer by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode to form an organic EL light emitting device.
  • Example 2 organic EL devices were similarly produced using the host materials and dopant materials shown in Tables 1 to 5 instead of the host material EM1 and the dopant material DM7-4.
  • Example 1 an organic EL device was prepared in the same manner using the following compound A instead of the host material EM1 and the following compound B instead of the dopant material DM7-4.
  • Example 2 an organic EL device was similarly prepared using the following compound C instead of the host material EM1 and the following compound D instead of the dopant material DM7-4.
  • Example 3 an organic EL device was similarly prepared using the following compound E instead of the host material EM1 and the following compound F instead of the dopant material DM7-4.
  • Tables 1 to 5 show the light emission wavelength and the half-life at an initial luminance of 1000 cd / m 2 of the organic EL element.
  • Example 4 Comparative Example 4 In Example 1, the following compound H-1 ′ was used instead of the host material EM1, and the dopant material DM2-4 ′ was used instead of the dopant material DM7-4, and an organic EL device was similarly produced.
  • Example 1 an organic EL device was produced in the same manner using the compound H-1 ′ in place of the host material EM1 and the dopant material DM10-4 ′ in place of the dopant material DM7-4.
  • Example 6 Comparative Example 6 In Example 1, the following compound H-2 ′ was used in place of the host material EM1, and the following compound D-1 ′ was used in place of the dopant material DM7-4 to similarly produce an organic EL device.
  • Example 7 Comparative Example 7 In Example 1, the following compound H-3 ′ was used in place of the host material EM1, and the following compound D-2 ′ was used in place of the dopant material DM7-4 to similarly produce an organic EL device.
  • Tables 6 to 12 show the luminous efficiencies of the organic EL devices obtained in Examples 175 to 430 and Comparative Examples 4 to 7 and the half lives at an initial luminance of 1000 cd / m 2 .
  • the organic EL element using the organic light emitting medium of the present invention is useful as a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.
  • a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.

Abstract

L'invention porte sur un milieu luminescent organique comprenant un dérivé de diaminopyrène représenté par la formule (1) et un dérivé d'anthracène représenté par la formule (2).
PCT/JP2009/053247 2008-02-25 2009-02-24 Milieu luminescent organique et élément el organique WO2009107596A1 (fr)

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