WO2014112359A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2014112359A1
WO2014112359A1 PCT/JP2014/000130 JP2014000130W WO2014112359A1 WO 2014112359 A1 WO2014112359 A1 WO 2014112359A1 JP 2014000130 W JP2014000130 W JP 2014000130W WO 2014112359 A1 WO2014112359 A1 WO 2014112359A1
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group
substituted
carbon atoms
unsubstituted
ring
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PCT/JP2014/000130
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Japanese (ja)
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亮平 橋本
圭 吉田
俊裕 岩隈
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons

Definitions

  • the present invention relates to an organic electroluminescence element.
  • Organic electroluminescence (EL) elements include a fluorescent type and a phosphorescent type, and an optimum element design has been studied according to each light emission mechanism. With respect to phosphorescent organic EL elements, it is known from their light emission characteristics that high-performance elements cannot be obtained by simple diversion of fluorescent element technology. The reason is generally considered as follows. Since phosphorescent light emission is light emission using triplet excitons, the energy gap of the compound used for the light emitting layer needs to be large. This is because the energy gap (hereinafter also referred to as singlet energy) of a compound is usually larger than the triplet energy (which means the energy difference between the lowest excited triplet state and the ground state) of the compound. It is.
  • a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must first be used for the light emitting layer.
  • Patent Documents 1 to 3 the development of a layer in contact with the anode side of the light emitting layer and the development of an element have been energetically performed.
  • Patent Document 3 proposes that a compound having an amine skeleton is used for the hole transport layer and the charge balance in the light emitting layer is adjusted to achieve both high efficiency and long life of the device.
  • a white organic EL device for illumination or the like includes a green light-emitting layer or a red light-emitting layer / green light-emitting layer, and a red light-emitting layer / blue light-emitting layer through an intermediate electrode, the first light-emitting unit and the second light-emitting unit.
  • stacked tandem light-emitting elements are used.
  • An object of the present invention is to provide a long-life organic EL element in which a red light emitting layer / blue light emitting layer are laminated.
  • the present inventors have found that a compound represented by formula (1) having a specific structure and a red phosphorescent material are included in the first light-emitting layer, and a compound or dibenzo containing a dibenzofuran skeleton in the second light-emitting layer.
  • the present invention was completed by finding that an organic EL device containing a compound containing a thiophene skeleton and a blue phosphorescent material has a long lifetime.
  • the first light emitting layer includes a compound represented by the following formula (1) and a red phosphorescent material
  • the second light emitting layer is provided with an organic electroluminescence device including a compound containing a dibenzofuran skeleton or a compound containing a dibenzothiophene skeleton and a blue phosphorescent material.
  • X is a group represented by O, S, or N-Ra.
  • Y 1 to Y 12 are each a group represented by N or C—Ra.
  • Ar 1 and Ar 2 are each a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • Ra is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms.
  • the plurality of Ras may be the same or different.
  • a long-life organic EL element in which a red light emitting layer / blue light emitting layer are laminated can be provided.
  • the organic EL element of the present invention is Between the anode and the cathode, including a first light emitting layer and a second light emitting layer,
  • the first light emitting layer includes a compound represented by the following formula (1) and a red phosphorescent material
  • the second light-emitting layer includes a compound containing a dibenzofuran skeleton or a compound containing a dibenzothiophene skeleton and a blue phosphorescent material.
  • X is a group represented by O, S, or N-Ra.
  • Y 1 to Y 12 are each a group represented by N or C—Ra.
  • Ar 1 and Ar 2 are each a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • Ra is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms.
  • the plurality of Ras may be the same or different.
  • Y 1 and Y 12 , Y 2 and Y 11 , Y 3 and Y 10 , Y 4 and Y 9 , Y 5 and Y 8 , and Y 6 and Y At least one pair of 7 is not identical to each other.
  • Y 1 and Y 12 , Y 2 and Y 11 , Y 3 and Y 10 , Y 4 and Y 9 , Y 5 and Y 8 and at least one pair of Y 6 and Y 7 are not identical to each other. That is, the carbazole moiety including Y 1 to Y 6 and the carbazole moiety including Y 7 to Y 12 are different from each other, and the two carbazole moieties do not have a line-symmetric structure.
  • Ar 1 and Ar 2 are preferably different substituents.
  • the crystallinity is reduced, and appropriate charge transport can be maintained by maintaining an amorphous organic film.
  • the organic EL device of the present invention in which a red light emitting layer / blue light emitting layer is laminated includes a green light emitting layer and a red light emitting layer / blue light emitting layer that are stacked as a first light emitting unit and a second light emitting unit via an intermediate electrode.
  • the tandem white light-emitting organic EL device is useful as either the first or second light-emitting unit.
  • 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 light source such as a copying machine, a printer, a backlight of a liquid crystal display or an instrument, a display board, a marker lamp, an illumination device, and the like.
  • X is preferably O or S, more preferably O.
  • the two adjacent Ras may combine to form a ring.
  • the ring formed by combining two adjacent Ras is preferably an aromatic ring.
  • the ring-forming atom may be a heteroaromatic ring containing a heteroatom such as N, O, or S.
  • Y 1 to Y 12 are preferably C—Ra, more preferably C—H.
  • Ar 1 and / or Ar 2 is represented by -L 1 -R 1 .
  • L 1 represents a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms
  • R 1 represents a substituted or unsubstituted ring aryl group. It represents an aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • the compound represented by the formula (1) is preferably a compound represented by the following formula (1a).
  • X, Ar 1 , Ar 2 , Y 1 , Y 2 , Y 5 , Y 6 , Y 7 , Y 8 , Y 11 and Y 12 are as defined in the formula (1). .
  • the compound represented by the formula (1) is preferably a compound represented by the following formula (1b).
  • X, Ar 2 , Y 1 , Y 2 , Y 5 , Y 6 , Y 7 , Y 8 , Y 11 and Y 12 are as defined in the formula (1).
  • Ar 11 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • X is preferably O.
  • Ar 2 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • Ar 1 and Ar 2 , or Ar 11 and Ar 2 are preferably different groups.
  • Ra is substituted or unsubstituted (X 10 is O, S or C—RaRa, Ra is as defined in the above formula (1), Y 20 is C—H or N). It is preferable.
  • the triplet energy of the compound of formula (1) is preferably 2.85 eV or more. Although an upper limit is not limited, Usually, it is 3.5 eV or less. Since the compound of formula (1) has a high hole transport property, the voltage of the device can be reduced.
  • the hole mobility of the compound of formula (1) is preferably 5 ⁇ 10 ⁇ 8 cm 2 / Vs or more. High hole mobility is preferable because the voltage is lowered.
  • the hole mobility (cm 2 / Vs) can be measured using impedance spectroscopy. Specifically, ITO (indium tin oxide) is used as an anode on a substrate, an organic layer containing a measurement target compound is formed thereon, and then Al is stacked as a cathode, thereby producing a hole-only device. A DC voltage carrying an AC voltage of 100 mV is applied, and the complex modulus is measured.
  • the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom.
  • the carbon contained in the substituent is not included in the number of ring-forming carbons.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • the benzene ring has 6 ring carbon atoms
  • the naphthalene ring has 10 ring carbon atoms
  • the pyridinyl group has 5 ring carbon atoms
  • the furanyl group has 4 ring carbon atoms.
  • the carbon number of the alkyl group is not included in the number of ring-forming carbons.
  • the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
  • the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly) Of the ring compound) represents the number of atoms constituting the ring itself.
  • An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
  • an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
  • the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
  • “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.
  • YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the above substituent.
  • the aromatic hydrocarbon ring includes a monocyclic aromatic hydrocarbon ring group and a condensed aromatic hydrocarbon ring group in which a plurality of hydrocarbon rings are condensed, and the heteroaromatic ring is a monocyclic heterocycle.
  • An aromatic ring group, a hetero-fused aromatic ring group in which a plurality of heteroaromatic rings are condensed, and a hetero-fused aromatic ring group in which an aromatic hydrocarbon ring and a heteroaromatic ring are condensed are included.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
  • the substituent is, for example, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or a carbon number
  • Examples thereof include a 5- to 18-heteroaromatic ring group, a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n- Heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n- And heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group,
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a norbornyl group, an adamantyl group, etc. Among them, those having 5 or 6 ring carbon atoms are preferable.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • Those having 3 or more carbon atoms may be linear, cyclic or branched, Of these, those having 1 to 6 carbon atoms are preferred.
  • cycloalkoxy group examples include a cyclopentoxy group and a cyclohexyloxy group, and among them, those having 5 or 6 ring carbon atoms are preferable.
  • aromatic hydrocarbon ring group examples include phenyl group, tolyl group, xylyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m -Terphenyl group, p-terphenyl group, naphthyl group, phenanthryl group, triphenylene group and the like.
  • a phenyl group, m-biphenyl group, and m-terphenyl group are preferred. Those having 6 to 18 ring carbon atoms are preferred.
  • arylene group examples include groups in which the above-described aromatic hydrocarbon ring group (aryl group) is divalent.
  • aralkyl group examples include the above-described alkyl group substituted by the above-described aromatic hydrocarbon ring group (aryl group).
  • aromatic heterocyclic group (heteroaromatic ring group) (heteroaryl group)
  • aromatic heterocyclic group include pyrrolyl group, pyrazinyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, indolyl group, isoindolyl group, furyl group, Benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, thienyl Group, pyrrolidinyl group, dioxanyl group, piperidinyl group, morpholinyl group, piperazinyl group, carbazolyl group, thiopheny
  • heteroarylene group examples include groups in which the above-described aromatic heterocyclic group (heteroaryl group) is divalent.
  • fluoroalkyl group examples include a group in which one or more fluorine atoms are substituted on the above-described alkyl group, and specifically include a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group. Etc. are preferred.
  • fluoroalkoxy group examples include groups in which one or more fluorine atoms are substituted on the above-described alkoxy group, and specifically include a trifluoromethoxy group, a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group. Etc. are preferred.
  • Examples of the aryloxy group include a group in which the above-described aryl group is substituted on an oxygen atom.
  • Examples of the arylthio group include a group in which the above aryl group is substituted on a sulfur atom.
  • Examples of the arylsulfonyl group include a group in which the above aryl group is substituted on the sulfonyl group.
  • Examples of the heteroaryloxy group include groups in which the above-described heteroaryl group is substituted on an oxygen atom.
  • Examples of the heteroarylthio group include a group in which the above-described heteroaryl group is substituted on a sulfur atom.
  • heteroarylsulfonyl group examples include a group in which the above aryl group is substituted on the sulfonyl group.
  • alkylene group the group which made the alkyl group mentioned above bivalent is mentioned.
  • cycloalkylene group examples include groups in which the above-described cycloalkyl group is divalent.
  • the triplet energy of the compound of the second light emitting layer is usually 2.85 eV or more, preferably 2.90 eV or more. Although an upper limit is not limited, Usually, it is 3.5 eV or less.
  • the compound of the second light emitting layer has a dibenzofuran skeleton or a dibenzothiophene skeleton. If a compound of the second light-emitting layer having a skeleton such as a dibenzofuran ring or a dibenzothiophene ring having electron resistance while maintaining the electron transporting ability is used, the lifetime can be extended.
  • the compounds of the second light-emitting layer will be described with specific structural formulas, but each compound includes a dibenzofuran skeleton and / or a dibenzothiophene skeleton as a partial structure.
  • the compound of the second light emitting layer is a compound represented by the following formula (2).
  • X 1 is an oxygen atom or a sulfur atom
  • One of X 2 and Y 2 is an oxygen atom, a sulfur atom or NR, and the other is a single bond, C (R) 2 , NR, an oxygen atom or a sulfur atom
  • Each R is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted ring forming carbon number;
  • Z 1 , Z 2 and Z 3 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or
  • n is an integer of 0 to 5, and when n is 2 or more, the plurality of Z 2 may be the same or different from each other, and the plurality of X 2 may be the same or different from each other The plurality of Y 2 may be the same as or different from each other.
  • n is an integer of 0 or 1.
  • R ′ is, for example, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 ring carbon atoms.
  • the compound of the second light emitting layer is preferably a compound represented by the following formula (2-1).
  • G 1 to G 6 are each independently CR 1 or a nitrogen atom.
  • G 11 to G 18 are each independently CR 2 or a nitrogen atom.
  • R and R 1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted carbon, An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring group; Aryloxy group having 6 to 18 ring carbon atoms, substituted or unsubstituted heteroaryloxy group having 5 to 18 ring atoms, substituted or unsubstitute
  • R 1 of G 2 and G 5 is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or An unsubstituted silyl group, a fluorine atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms.
  • R 2 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • each R 2 may be the same or different.
  • R, R 1 and R 2 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 carbon atoms.
  • a heteroaromatic ring group a silyl group, a fluorine atom, a fluoroalkyl group having 1 to 20 carbon atoms, a fluoroalkoxy group having 1 to 20 carbon atoms, or a cyano group.
  • Xa is an oxygen atom or a sulfur atom.
  • the compound of the second light emitting layer is preferably represented by any one of the following formulas (2-2a) to (2-2c), (2-3a) to (2-3c), and (2-4a). Is done.
  • G 211 to G 214 are each independently CR 21 or a nitrogen atom.
  • G 221 to G 228 are each independently CR 22 or a nitrogen atom.
  • Ga to Gk are each independently CR 23 or a nitrogen atom.
  • G 214 and Ga are carbon atoms, they may be bonded via an oxygen or sulfur atom.
  • G213 and Gd are carbon atoms, they may be bonded via an oxygen or sulfur atom.
  • R 21 , R 22 and R 23 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, substituted Or an unsubstituted aryloxy group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 5 to 18 ring atoms, a substituted or unsubstituted silyl group, a fluorine atom, substituted or unsubstituted A fluoroalkyl group having 1 to 20 carbon atoms,
  • the plurality of R 21 may be the same or different from each other.
  • the plurality of R 22 may be the same or different from each other.
  • the plurality of R 23 may be the same or different from each other.
  • R 21 , R 22 and R 23 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 alkoxy groups, cycloalkoxy groups having 3 to 20 ring carbon atoms, aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms, aryloxy groups having 6 to 18 ring carbon atoms, 5 to 5 ring atoms
  • X 1 is an oxygen atom or a sulfur atom.
  • X 2 is an oxygen atom, a sulfur atom, or C (CH 3 ) 2 . )
  • the compound of the second light emitting layer is preferably represented by any of the following formulas (2-5a) to (2-5f).
  • E 1 and E 2 are each independently an oxygen atom, a sulfur atom or NR 5 ; However, at least one of E 1 and E 2 is an oxygen atom or a sulfur atom, G 51 to G 60 are each independently CR 6 or a nitrogen atom.
  • R 5 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted ring carbon atom having 6 to 30 carbon atoms.
  • R 6 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • the plurality of R 5 may be the same or different from each other.
  • the plurality of R 6 may be the same or different from each other.
  • R 5 and R 6 have a substituent
  • the substituent R ′ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, or an alkoxy having 1 to 20 carbon atoms.
  • a cycloalkoxy group having 3 to 20 ring carbon atoms an aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, and a hetero ring having 5 to 18 ring atoms.
  • the compound of the second light emitting layer may be a compound represented by the following formulas (2-4) to (2-9).
  • X 1 and X 2 are each independently an oxygen atom or a sulfur atom
  • Each R 1 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted ring forming carbon;
  • An aromatic hydrocarbon ring group of 6-30, or a substituted or unsubstituted aromatic heterocyclic group of 3-30 ring-forming atoms, s, t, and u are each independently an integer of 1-4.
  • each group and its substituent in the compound of the second light emitting layer include those exemplified for the compound of formula (1).
  • a phosphorescent material (sometimes called a phosphorescent dopant) will be described.
  • the phosphorescent material is a so-called phosphorescent dopant.
  • the phosphorescent dopant include metal complex compounds, preferably a compound having a metal atom selected from Ir, Pt, Os, Au, Cu, Re and Ru and a ligand.
  • the ligand preferably has an ortho metal bond.
  • the phosphorescent dopant is preferably a compound containing a metal atom selected from Ir, Os and Pt in that the phosphorescent quantum yield is high and the external quantum efficiency of the light-emitting element can be further improved, and an iridium complex, It is more preferable that it is a metal complex such as an osmium complex and a platinum complex, among which an iridium complex and a platinum complex are more preferable, and an orthometalated iridium complex is most preferable.
  • the dopant may be a single type or a mixture of two or more types.
  • the red phosphorescent material contained in the first light emitting layer is a compound that can emit phosphorescence having an emission wavelength in the range of 550 to 750 nm, preferably in the range of 570 to 730 nm.
  • Examples of the compound used as the red phosphorescent material include Ir (pic) 3 , (pic) 2 Ir (acac), (btp) 2 Ir (acac), and (pic) 2 Ir (acac), (Btp) 2 Ir (acac) and the like are preferable.
  • the triplet energy Eg T of the red phosphorescent material is preferably 2.10 eV or more.
  • the blue phosphorescent material contained in the second light emitting layer is a compound that can emit phosphorescence having an emission wavelength in the range of 430 to 550 nm, preferably in the range of 430 to 530 nm, more preferably in the range of 430 to 510 nm.
  • the compound used as the blue phosphorescent material include FIrpic, FCNIrpic, FIr6, iridium complex of carbene ligand, iridium complex of phenylimidazole ligand, iridium complex of carbene ligand, phenylimidazole, and the like.
  • An iridium complex of a ligand or the like is preferable.
  • the triplet energy Eg T of the blue phosphorescent material is preferably 2.70 eV or more.
  • the organic EL device of the present invention includes a first light emitting layer containing the compound of the above formula (1) and a red phosphorescent material, and a compound containing a dibenzofuran skeleton or a compound containing a dibenzothiophene skeleton and a blue phosphorescent material.
  • Other configurations are not particularly limited as long as they have an element configuration including a second light-emitting layer that includes.
  • the first light emitting layer may contain one or more compounds of formula (1).
  • the first light-emitting layer contains one kind of red phosphorescent material (phosphorescent dopant) alone or two or more kinds.
  • the second light emitting layer may contain one or more compounds containing a dibenzofuran skeleton and / or a compound containing a dibenzothiophene skeleton.
  • a 2nd light emitting layer contains blue phosphorescent light emitting material (phosphorescent dopant) 1 type individually, or contains 2 or more types.
  • the first light emitting layer and the second light emitting layer are preferably adjacent to each other.
  • the organic layer adjacent to the second light emitting layer may contain a compound containing a dibenzofuran skeleton and / or a compound containing a dibenzothiophene skeleton alone or in combination of two or more.
  • This organic layer can function as a hole blocking layer.
  • a hole transporting material is added to the first light emitting layer, deterioration of the compound of the formula (1) is suppressed, so that the lifetime of the element can be improved.
  • the first light-emitting layer is preferably composed of only the compound of formula (1) and the red phosphorescent material, or only the compound of formula (1), the red phosphorescent material and the hole transporting material (including inevitable impurities). .
  • the addition concentration of the red phosphorescent dopant or hole transporting material in the first light emitting layer is not particularly limited, but is preferably 0.1 to 20% by weight (wt%), more preferably 0.1% each. ⁇ 10 wt% (wt%).
  • Examples of the hole transporting material include a material for a hole injection / transport layer described later.
  • the addition concentration of the blue phosphorescent dopant in the second light emitting layer is not particularly limited, but is preferably 0.1 to 40% by weight (wt%), more preferably 0.1 to 30% by weight (wt%). It is.
  • FIG. 1 is a schematic view showing a layer structure of an embodiment of the organic EL device of the present invention.
  • the organic EL element 1 includes an anode 20, a hole injection layer 30, a hole transport layer 40, an electron blocking layer 50, a first light emitting layer 60, a second light emitting layer 62, and a hole blocking layer 70 on a substrate 10.
  • the electron transport layer 80, the electron injection layer 90, and the cathode 100 are stacked in this order. Any of the hole injection layer, the hole transport layer, the electron blocking layer, the hole blocking layer, the electron transport layer, and the electron injection layer may be formed.
  • the organic EL element of the present invention can employ various known configurations.
  • the configuration other than the layer using the organic EL element material of the present invention described above is not particularly limited, and a known material or the like can be used.
  • a known material or the like can be used.
  • the layer of the element of Embodiment 1 is demonstrated easily, the material applied to the organic EL element of this invention is not limited to the following.
  • a glass plate, a polymer plate or the like can be used as the substrate.
  • the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfone, and polysulfone.
  • the anode is made of, for example, a conductive material, and a conductive material having a work function larger than 4 eV is suitable.
  • the conductive material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and their alloys, ITO substrate, tin oxide used for NESA substrate, indium oxide, and the like.
  • examples thereof include metal oxides and organic conductive resins such as polythiophene and polypyrrole.
  • the anode may be formed with a layer structure of two or more layers if necessary.
  • the cathode is made of, for example, a conductive material, and a conductive material having a work function smaller than 4 eV is suitable.
  • the conductive material include, but are not limited to, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and alloys thereof.
  • the alloy 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.
  • the cathode may be formed with a layer structure of two or more layers, and the cathode can be produced by forming a thin film from the conductive material by a method such as vapor deposition or sputtering.
  • the transmittance of the cathode for light emission is preferably greater 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.
  • the organic EL element of the present invention may have a fluorescent light emitting layer.
  • a known material can be used for the fluorescent light emitting layer.
  • the light emitting layer may be a double host (also referred to as a host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer. Moreover, it is good also as a double dopant.
  • each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.
  • the light emitting layer may be a single layer or a laminated structure. When the light emitting layer is stacked, the recombination region can be concentrated on the light emitting layer interface by accumulating electrons and holes at the light emitting layer interface. This improves the quantum efficiency.
  • the hole injection layer and the hole transport layer help to inject holes into the light emitting layer and transport them to the light emitting region, and have high hole mobility and low ionization energy. Is a layer.
  • As the material for the hole injection / transport layer a material that transports holes to the light emitting layer with lower electric field strength is preferable. Further, when an electric field is applied with a hole mobility of, for example, 10 4 to 10 6 V / cm, At least 10 ⁇ 4 cm 2 / V ⁇ sec is preferable.
  • the material for the hole injection / transport layer include triazole derivatives (see US Pat. No. 3,112,197) and oxadiazole derivatives (see US Pat. No. 3,189,447). ), Imidazole derivatives (see JP-B-37-16096, etc.), polyarylalkane derivatives (US Pat. Nos. 3,615,402, 3,820,989, 3,542,544) Nos. 45-555, 51-10983, 51-93224, 55-17105, 56-4148, 55-108667, 55-156953, 56-36656, etc.), pyrazoline derivatives and pyrazolone derivatives (US Pat. No. 3,180,729, No. 4) Nos.
  • Gazette 55-52063, 55-52064, 55-46760, 57-11350, 57- No. 148749, JP-A-2-311591, etc.), stilbene derivatives (JP-A Nos. 61-210363, 61-228451, 61-14642, 61-72255, etc.) 62-47646, 62-36684, 62-10652, 62-30255, 60-93455, 60-94462, 60-174749, 60 -175052, etc.), silazane derivatives (US Pat. No. 4,950,950), polysilanes (JP-A-2-204996), aniline copolymers (JP-A-2-282263) Etc.
  • inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.
  • a cross-linkable material can be used as the material for the hole injection / transport layer.
  • Mater. 2008, 20, 413-422, Chem. Mater. Examples include a layer obtained by insolubilizing a cross-linking material such as 2011, 23 (3), 658-681, WO2008108430, WO2009102027, WO2009123269, WO2010016555, WO2010018813 by heat, light or the like.
  • the electron injection layer and the electron transport layer are layers that assist the injection of electrons into the light emitting layer and transport them to the light emitting region, and have high electron mobility.
  • an electrode for example, a cathode
  • the electron injecting / transporting layer is appropriately selected with a film thickness of several nm to several ⁇ m.
  • the electron mobility is preferably at least 10 ⁇ 5 cm 2 / Vs or more when an electric field of V / cm is applied.
  • an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, such as a pyridine ring. , Pyrimidine ring, triazine ring, benzimidazole ring, phenanthroline ring, quinazoline ring and the like.
  • an organic layer having semiconductivity may be formed by doping a donor material (n) and acceptor material (p).
  • a donor material (n) and acceptor material (p) A typical example of N doping is to dope an electron transport material with a metal such as Li or Cs, and a typical example of P doping is to dope an acceptor material such as F4TCNQ into a hole transport material (for example, see Japanese Patent No. 3695714).
  • each layer of the organic EL device of the present invention a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied. be able to.
  • the thickness of each layer is not particularly limited, but must be set to an appropriate 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 measuring method of the characteristic of a compound is as follows.
  • (1) Triplet energy (E T ) The measurement was performed using a commercially available apparatus F-4500 (manufactured by Hitachi).
  • the conversion formula of triplet energy (E T ) is as follows.
  • E T (eV) 1239.85 / ⁇ ph
  • “ ⁇ ph ” (unit: nm) draws a tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side when the phosphorescence spectrum is represented with the phosphorescence intensity on the vertical axis and the wavelength on the horizontal axis. , The wavelength value of the intersection of the tangent and the horizontal axis.
  • Ionization potential A thin film of the measurement compound was formed on the ITO substrate by a vacuum deposition method or a coating method, and the measurement was performed using a commercially available atmospheric photoelectron spectrometer AC-3 (manufactured by Riken Keiki Co., Ltd.).
  • the evaluation method of the organic EL element is as follows.
  • the organic EL device of the example using the compound of the present invention as the host of the red phosphorescent light emitting layer has an improved half-life compared to the device of Comparative Example 1.
  • Example 1 A glass substrate with a 130 nm-thick ITO electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes.
  • the glass substrate with the ITO electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound (HI1) is first thickened so as to cover the ITO electrode line on the surface on which the ITO electrode line is formed.
  • the compound (HT1) was then vapor deposited by resistance heating at a thickness of 50 nm, and thin films were sequentially formed. The film formation rate was 1 ⁇ / s. These thin films function as a hole injection layer and a hole transport layer, respectively.
  • a compound (1) and a compound (RD1) were simultaneously deposited by resistance heating to form a thin film having a thickness of 10 nm.
  • the film formation rates were 1.0 ⁇ / s and 0.064 ⁇ / s, respectively.
  • the compound (RD1) was deposited so as to have a mass ratio of 6% with respect to the total mass of the compound (1) and the compound (RD1).
  • This thin film functions as a red phosphorescent light emitting layer.
  • the compound (H1) and the compound (BD1) were simultaneously deposited by resistance heating to form a thin film having a thickness of 50 nm.
  • the compound (BD1) was deposited so as to have a mass ratio of 20% with respect to the total mass of the compound (H1) and the compound (BD1).
  • the film formation rates were 1.2 ⁇ / s and 0.3 ⁇ / s, respectively.
  • This thin film functions as a phosphorescent light emitting layer.
  • a thin film having a thickness of 10 nm was formed on the phosphorescent light emitting layer by resistance heating vapor deposition of the compound (H1). The film formation rate was 1 ⁇ / s. This thin film functions as a hole blocking layer.
  • a compound (ET1) was deposited by resistance heating vapor deposition to form a thin film having a thickness of 10 nm.
  • the film formation rate was 1 ⁇ / s.
  • This film functions as an electron injection layer.
  • LiF having a film thickness of 1.0 nm was deposited on the electron injection layer at a film formation rate of 0.1 ⁇ / s.
  • metal aluminum was vapor-deposited on the LiF film at a film formation rate of 8.0 ⁇ / s to form a metal cathode having a film thickness of 80 nm, thereby manufacturing an organic EL element.
  • Example 2 and Comparative Examples 1 and 2 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in Table 2 were used as the host material for the red phosphorescent light emitting layer instead of the compound (1). The results are shown in Table 3. The “half life (relative%)” is a relative ratio when the half life of the element of Comparative Example 2 is 100%. Table 1 shows the triplet energy and ionization potential of the compounds used, and Table 2 shows the evaluation results of the devices.
  • the organic EL device of the example using the compound of the present invention as the host material of the red phosphorescent light emitting layer has an improved lifetime as compared with the devices of Comparative Examples 1 and 2. .
  • Example 3 and 4 and Comparative Examples 3 and 4 The same procedure as in Example 1 was conducted except that compound (H2) was used as the host for the phosphorescent layer instead of compound (H1), and the compounds listed in Table 3 were used as the host material for the red phosphorescent layer instead of compound (1). Thus, an organic EL element was produced and evaluated. The results are shown in Table 3. The “half life (relative%)” is a relative ratio when the half life of the element of Comparative Example 4 is 100%.
  • the organic EL device of the example using the compound of the present invention as the host material of the red phosphorescent light emitting layer has an improved lifetime as compared with the devices of Comparative Examples 3 and 4. .

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Abstract

L'invention concerne un élément électroluminescent organique qui contient une première couche électroluminescente et une seconde couche électroluminescente entre une électrode positive et une électrode négative, la première couche électroluminescente contenant un matériau électroluminescent phosphorescent dans le rouge et un composé représenté par la formule (1), et la seconde couche électroluminescente contient un matériau électroluminescent phosphorescent dans le bleu et un composé contenant un squelette de dibenzothiophène ou un composé contenant un squelette de dibenzofurane.
PCT/JP2014/000130 2013-01-15 2014-01-14 Élément électroluminescent organique WO2014112359A1 (fr)

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Cited By (1)

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WO2015159706A1 (fr) * 2014-04-16 2015-10-22 出光興産株式会社 Composé, élément électroluminescent organique et dispositif électronique

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WO2008149617A1 (fr) * 2007-06-04 2008-12-11 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique et appareil d'éclairage
WO2009008100A1 (fr) * 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Matériau pour élément à électroluminescence organique, et élément à électroluminescence organique préparé à l'aide du matériau
WO2009148062A1 (fr) * 2008-06-05 2009-12-10 出光興産株式会社 Composé polycyclique et dispositif électroluminescent organique l'utilisant
US20120168734A1 (en) * 2009-08-11 2012-07-05 Duksan High Metal Co., Ltd. Compound containing 5-membered heterocycles, organic light-emitting device using same, and terminal comprising the latter

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WO2008149617A1 (fr) * 2007-06-04 2008-12-11 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique et appareil d'éclairage
WO2009008100A1 (fr) * 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Matériau pour élément à électroluminescence organique, et élément à électroluminescence organique préparé à l'aide du matériau
WO2009148062A1 (fr) * 2008-06-05 2009-12-10 出光興産株式会社 Composé polycyclique et dispositif électroluminescent organique l'utilisant
US20120168734A1 (en) * 2009-08-11 2012-07-05 Duksan High Metal Co., Ltd. Compound containing 5-membered heterocycles, organic light-emitting device using same, and terminal comprising the latter

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Publication number Priority date Publication date Assignee Title
WO2015159706A1 (fr) * 2014-04-16 2015-10-22 出光興産株式会社 Composé, élément électroluminescent organique et dispositif électronique
US10249826B2 (en) 2014-04-16 2019-04-02 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescent element and electronic device

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