WO2017150380A1 - Composé de quinoxaline et utilisation de celui-ci - Google Patents

Composé de quinoxaline et utilisation de celui-ci Download PDF

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WO2017150380A1
WO2017150380A1 PCT/JP2017/007151 JP2017007151W WO2017150380A1 WO 2017150380 A1 WO2017150380 A1 WO 2017150380A1 JP 2017007151 W JP2017007151 W JP 2017007151W WO 2017150380 A1 WO2017150380 A1 WO 2017150380A1
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group
phenyl
independently
carbon atoms
biphenyl
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PCT/JP2017/007151
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Japanese (ja)
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松本直樹
小野洋平
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東ソー株式会社
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Priority claimed from JP2016248534A external-priority patent/JP6780491B2/ja
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Publication of WO2017150380A1 publication Critical patent/WO2017150380A1/fr

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    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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

Definitions

  • the present invention relates to a quinoxaline compound and an organic EL device using the same.
  • An organic EL element is a surface-emitting element in which an organic thin film is held between a pair of electrodes, and has features such as a thin and light weight, a high viewing angle, and a high-speed response, and is expected to be applied to various display elements. . Recently, some practical applications such as mobile phone displays have begun. On the other hand, there is still a problem with the light emission efficiency of the organic EL element, and in particular, a light emitting material (light emission host, light emission dopant) having a large influence on the light emission efficiency is required to be improved.
  • the light emission of the organic EL element is obtained by recombination of electrons and holes injected from the cathode and the anode inside the light emitting layer. Therefore, the material used for the light-emitting layer needs to have a bipolar property capable of receiving both electrons and holes. For example, in an organic EL element using a light emitting layer that cannot transport electrons and holes in a well-balanced manner, extra holes or electrons that do not contribute to light emission are generated, resulting in a decrease in light emission efficiency. Moreover, since excessive holes and electrons induce deterioration of the hole transport layer and the electron transport layer adjacent to the light emitting layer, the lifetime of the organic EL element is deteriorated.
  • carbazole compounds such as 4,4′-bis (9-carbazolyl) biphenyl and 1,3-bis (9-carbazolyl) benzene are well known (for example, see Non-Patent Documents 1 and 2). ).
  • these carbazole compounds are insufficient in terms of the bipolar property of transporting electrons and holes in a well-balanced manner, and satisfactory results are not obtained with respect to the light emission efficiency and lifetime of the organic EL element.
  • the quinoxaline compound represented by the following general formula (1) and have completed the present invention.
  • the quinoxaline compound has a substituent in which a carbazole skeleton is essential at a specific position of the quinoxaline ring, and has not been reported or suggested in the prior art.
  • R 1 and R 2 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms
  • these groups are each independently a methyl group, ethyl group
  • R 3 to R 5 each independently represents a hydrogen atom, a methyl group, a phenyl group, a naphthyl group, or a biphenyl group.
  • Z is a group represented by any one of the following general formulas (2) to (21). )
  • R 6 , R 7 , R 9 , R 10 , R 12 to R 38 , R 40 to R 43 , R 45 to R 48 , R 50 to R 53 , and R 55 to R 66 are each independently hydrogen
  • An atom, a methyl group, a phenyl group, a naphthyl group, or a biphenyl group is represented.
  • R 8 , R 11 , R 39 , R 44 , R 49 , and R 54 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these Each independently represents a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a quinolyl group, Having at least one substituent selected from the group consisting of a pyrimidyl group, a diphenylpyridyl group, a diphenylpyrimidyl group, a diphenyltriazyl group, a dibenzothienyl group, a dibenzofuranyl group, a cyano group, and a deuterium atom; May also be expressed.
  • Ar 1 to Ar 6 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, ethyl group, A substituent selected from the group consisting of a group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a phenyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9-carbazolyl group, a cyano group, and a deuterium atom It may have one or more groups].
  • X represents a single bond, an oxygen atom or a sulfur atom.
  • a quinoxaline compound represented by the general formula (1) [2] R 1 and R 2 are each independently a phenyl group, methylphenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, naphthylphenyl group, phenanthrylphenyl group, pyridyl group, pyridylphenyl.
  • the quinoxaline compound according to [1] which is a group or a hydrogen atom.
  • R 8 , R 11 , R 39 , R 44 , R 49 , and R 54 are each independently a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a triazyl group, a quinolyl group.
  • Group, quinazolyl group, dibenzofuranyl group, or dibenzothienyl group [These groups are each independently methyl group, phenyl group, biphenyl group, naphthyl group, phenanthryl group, pyridyl group, quinolyl group, pyrimidyl group, diphenyl group.
  • the quinoxaline compound according to any one of [1] to [2], wherein [4] R 8 , R 11 , R 39 , R 44 , R 49 , and R 54 are each independently a phenyl group, a methylphenyl group, a naphthyl group, a biphenyl group, a terphenyl group, or a dimethylfluorenyl group.
  • the quinoxaline compound in any one of.
  • Ar 1 to Ar 6 are aromatic hydrocarbon groups having 6 to 14 carbon atoms that may be linked or condensed, or at least one oxygen atom, nitrogen atom, or sulfur atom.
  • heteroaromatic groups these groups are each independently a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a phenyl group, a dibenzofuranyl group, a dibenzo group, Any one of [1] to [3], which may have one or more substituents selected from the group consisting of thienyl group, 9-carbazolyl group, cyano group, and deuterium atom]
  • Ar 1 to Ar 6 are each independently a phenyl group, methylphenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, naphthylphenyl group, dibenzofuranyl group, dibenzothienyl group, dibenzofuran
  • the quinoxaline compound of the present invention has not been reported or suggested in the prior art, as a result of investigation, it has been found that it has a good bipolar property capable of receiving electrons and holes. .
  • the organic EL device having at least one light emitting layer containing the quinoxaline compound of the present invention can efficiently perform both electron injection and hole injection into the light emitting layer. It is suggested that the recombination of holes can be performed efficiently.
  • the quinoxaline compound of the present invention has a significantly lower driving voltage of the organic EL device than the inventive compound disclosed in the prior art based on the structural requirements different from the prior art, and emits light. There was a remarkable effect that the efficiency was remarkably improved and the device life was remarkably improved. Such a remarkable effect of the present invention cannot be easily predicted from the prior art having different constituent requirements.
  • R 1 and R 2 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [ These groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a cyano group.
  • cyano group Represents a deuterium atom or a hydrogen atom.
  • the aromatic hydrocarbon group having 6 to 20 carbon atoms in R 1 and R 2 can be represented as an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be linked or condensed, and as the group, although not particularly limited, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a phenanthryl group, a fluoranthenyl group, an anthryl group, or a pyrenyl group can be mentioned. .
  • the heteroaromatic group having 3 to 20 carbon atoms in R 1 and R 2 can be represented as a heteroaromatic group having 3 to 20 carbon atoms which may be linked or condensed, and the group is particularly limited.
  • a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom, nitrogen atom, or sulfur atom can be given, and more preferably, an oxygen atom, a nitrogen atom
  • Examples of the heteroaromatic group having 3 to 20 carbon atoms containing at least one atom selected from the group consisting of sulfur atoms on the aromatic ring include, but are not particularly limited to, for example, , Pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, pyrazi Group, 1,3,5-triazyl group, indolyl group,
  • the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms in R 1 and R 2 is not particularly limited, and examples thereof include a propyl group, an isopropyl group, an n-butyl group, and a sec-butyl group. Tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group and the like.
  • R 1 and R 2 include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n- Dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-tr
  • R 1 and R 2 are each independently an aromatic hydrocarbon group having 6 to 14 carbon atoms which may be linked or condensed, or at least, in that the effect of extending the lifetime of the organic EL device is high.
  • a C3-C12 heteroaromatic group containing one oxygen atom, nitrogen atom, or sulfur atom [these groups are each independently a methyl group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, And may have one or more substituents selected from the group consisting of a pyridyl group], preferably a methyl group or a hydrogen atom, each independently a phenyl group, a methylphenyl group, a naphthyl group, More preferably a biphenyl group, a terphenyl group, a phenanthryl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridy
  • the aromatic hydrocarbon group that may be linked or condensed with 6 to 14 carbon atoms is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, a biphenyl group, and an anthryl group. It is done.
  • the C3-C12 heteroaromatic group containing at least one oxygen atom, nitrogen atom, or sulfur atom is not particularly limited, but includes a pyridyl group, a phenylpyridyl group, a pyridylphenyl group, a dibenzo group. Examples include a furanyl group or a dibenzothienyl group.
  • R 3 to R 5 each independently represents a hydrogen atom, a methyl group, a phenyl group, a naphthyl group, or a biphenyl group.
  • a hydrogen atom, a methyl group, or a phenyl group is preferable independently from the viewpoint that the effect of extending the lifetime of the organic EL element is high, and a hydrogen atom is more preferable.
  • Z is represented by any one of the following general formulas (2) to (21).
  • R 6 , R 7 , R 9 , R 10 , R 12 to R 38 , R 40 to R 43 , R 45 to R 48 , R 50 to R 53 , and R 55 to R 66 each independently represent a hydrogen atom, a methyl group, a phenyl group, a naphthyl group, or a biphenyl group.
  • R 6 , R 7 , R 9 , R 10 , R 12 to R 38 , R 40 to R 43 , R 45 to R 48 , R 50 to R 53 , and R 55 to R 66 are the long lifetime of the organic EL element. It is preferable that they are each independently a hydrogen atom, a methyl group, or a phenyl group from the viewpoint of excellent conversion effect.
  • R 8 , R 11 , R 39 , R 44 , R 49 , and R 54 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or Heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a phenyl group, a biphenyl group, From the group consisting of naphthyl group, phenanthryl group, pyridyl group, quinolyl group, pyrimidyl group, diphenylpyridyl group, diphenylpyrimidyl group, diphenyltriazyl group, dibenzothienyl group, dibenzofuranyl group, cyano group, and deuterium atom It may have one or more selected substituents].
  • the aromatic hydrocarbon group having 6 to 20 carbon atoms has the same definition as that represented by R 1 and R 2 , and a preferred range Is the same as that shown for R 1 and R 2 .
  • the heteroaromatic group having 3 to 20 carbon atoms has the same definition as that represented by R 1 and R 2 , and a preferred range is as follows. Are the same as those shown for R 1 and R 2 .
  • R 8 , R 11 , R 39 , R 44 , R 49 , and R 54 the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms has the same definition as shown for R 1 and R 2 The preferred range is the same as that shown for R 1 and R 2 .
  • R 8 , R 11 , R 39 , R 44 , R 49 , and R 54 are aromatics that may be linked or condensed with 6 to 14 carbon atoms in that they are excellent in the effect of extending the life of the organic EL device.
  • a hydrocarbon group or a heteroaromatic group having 3 to 12 carbon atoms containing at least one oxygen atom, nitrogen atom or sulfur atom [these groups are each independently a methyl group, a phenyl group, a biphenyl group, , Naphthyl group, phenanthryl group, pyridyl group, quinolyl group, pyrimidyl group, diphenylpyridyl group, diphenylpyrimidyl group, diphenyltriazyl group, dibenzothienyl group, dibenzofuranyl group, cyano group, and deuterium atom It may preferably have one or more substituents selected from the above, and each independently represents a phenyl group
  • the aromatic hydrocarbon group having 6 to 14 carbon atoms which may be linked or condensed has the same definition as that represented by R 1 and R 2 , and the preferred range is also represented by R 1 and R 2 . It is the same as that.
  • the heteroaromatic group having 3 to 12 carbon atoms containing at least one oxygen atom, nitrogen atom or sulfur atom has the same definition as that represented by R 1 and R 2 , and the preferred range is also R 1. And R 2 are the same.
  • Ar 1 to Ar 6 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these Each independently represents a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a phenyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9-carbazolyl group, a cyano group And may have one or more substituents selected from the group consisting of deuterium atoms].
  • the aromatic hydrocarbon group having 6 to 20 carbon atoms has the same definition as that represented by R 1 and R 2 , and the preferred range is the same as that represented by R 1 and R 2 It is.
  • the heteroaromatic group having 3 to 20 carbon atoms has the same definition as that represented by R 1 and R 2 , and the preferred range is the same as that represented by R 1 and R 2. is there.
  • the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms has the same definition as that represented by R 1 and R 2 , and the preferred range is also represented by R 1 and R 2 . It is the same as that shown.
  • Ar 1 to Ar 6 are aromatic hydrocarbon groups having 6 to 14 carbon atoms which may be linked or condensed, or at least one oxygen atom or nitrogen atom, in terms of excellent life extension of the organic EL device.
  • a heteroaromatic group having 3 to 12 carbon atoms containing a sulfur atom [these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms] May have one or more substituents selected from the group consisting of a phenyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9-carbazolyl group, a cyano group, and a deuterium atom] Independently, phenyl group, methylphenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, naphthylphenyl group, dibenzofuranyl group, dibenz
  • a naphthyl group More preferably a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a naphthylphenyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzofuranylphenyl group, or a dibenzothienylphenyl group, More preferably, it is a phenyl group, a methylphenyl group, a naphthyl group, or a biphenyl group.
  • the aromatic hydrocarbon group having 6 to 14 carbon atoms which may be linked or condensed has the same definition as that represented by R 1 and R 2 , and the preferred range is also represented by R 1 and R 2 . It is the same as that.
  • the heteroaromatic group having 3 to 12 carbon atoms containing at least one oxygen atom, nitrogen atom or sulfur atom has the same definition as that represented by R 1 and R 2 , and the preferred range is also R 1. And R 2 are the same.
  • X represents a single bond, an oxygen atom or a sulfur atom.
  • the quinoxaline compound represented by the general formula (1) can be synthesized by the following route, for example.
  • a halogenated quinoxaline compound (21) is obtained by a condensation reaction of halogenated orthophenylenediamines (19) and 1,2-diketones (20). Subsequently, the halogenated quinoxaline compound (21) and the secondary amine compound represented by the general formula (22) are reacted using a copper catalyst or a palladium catalyst in the presence of a base, according to the general formula (1).
  • the quinoxaline compound represented can be obtained.
  • R 1 to R 5 and Z represent the same definition as in the general formula (1).
  • A represents a halogen atom (iodine, bromine, chlorine, or fluorine).
  • the compounds represented by the general formulas (19), (20) and (22) commercially available compounds can be used, or they can be synthesized based on generally known methods.
  • the quinoxaline compound represented by the general formula (1) of the present invention can be preferably used as a light emitting host material, a light emitting dopant material, an electron transport material, and a hole transport material for an organic EL device.
  • the quinoxaline compound represented by the general formula (1) of the present invention has bipolar properties, can stably transport holes and electrons, and further has excellent light emission characteristics. When used as a light emitting layer, it is possible to achieve high efficiency and long life of the organic EL element.
  • the quinoxaline compound represented by the general formula (1) of the present invention is used as a light emitting layer of an organic EL device
  • the quinoxaline compound is used alone, used by doping a known light emitting host material, or a known It can be used by doping with a luminescent dopant.
  • the quinoxaline compound represented by the general formula (1) when used as a hole transport layer or an electron transport layer of an organic EL device, a conventionally known fluorescent or phosphorescent light-emitting material is used. can do.
  • the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
  • Examples of a method for forming a light emitting layer, a hole transport layer, or an electron transport layer containing the quinoxaline compound represented by the general formula (1) include known methods such as vacuum deposition, spin coating, and casting. Can be applied.
  • those including a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are preferable. Layers may be omitted, or vice versa.
  • the anode and cathode of the organic EL element are connected to a power source through an electrical conductor.
  • the organic EL element operates by applying a potential between the anode and the cathode.
  • Holes are injected into the organic EL element from the anode, and electrons are injected into the organic EL element at the cathode.
  • the organic EL element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate.
  • the electrode in contact with the substrate is called the lower electrode for convenience.
  • the lower electrode is an anode, but the organic EL element of the present invention is not limited to such a form.
  • the substrate may be light transmissive or opaque depending on the intended emission direction. The light transmission characteristics can be confirmed by electroluminescence emission through the substrate. Generally, transparent glass or plastic is used as the substrate in such a case.
  • the substrate may be a composite structure including multiple material layers.
  • the anode is formed by passing or substantially passing the emission.
  • the general transparent anode (anode) material used in the present invention is not particularly limited, and examples thereof include indium-tin oxide (ITO), indium-zinc oxide (IZO), and tin oxide. .
  • ITO indium-tin oxide
  • IZO indium-zinc oxide
  • tin oxide tin oxide
  • Other metal oxides such as aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide can also be used.
  • metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode.
  • the anode can be modified with plasma-deposited fluorocarbon. If electroluminescence emission is confirmed only through the cathode, the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium, platinum and the like.
  • a plurality of hole transporting layers such as a hole injection layer and a hole transport layer can be provided between the anode and the light emitting layer.
  • the hole injection layer and the hole transport layer have a function of transmitting holes injected from the anode to the light emitting layer.
  • the hole injection layer and the hole transport layer are often used in a lower electric field. Holes can be injected into the light emitting layer.
  • a known hole injection material and hole transport material can be used as the hole transport layer and / or the hole injection layer.
  • a known hole injection material and hole transport material can be used as the hole transport layer and / or the hole injection layer.
  • the hole injecting material and the hole transporting material those described above can be used, and porphyrin compounds, aromatic tertiary amine compounds, and s
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′.
  • inorganic compounds such as p-type-Si and p-type-SiC can be used as the hole injection material and the hole transport material.
  • the hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the light emitting layer contains the quinoxaline compound of the present invention.
  • a known light emitting material light emitting host material, fluorescent dopant, phosphorescent dopant
  • the quinoxaline compound of the present invention can be selected and combined with the quinoxaline compound of the present invention.
  • Examples of the luminescent host material include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthranyl group.
  • DPVBi 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl
  • BCzVBi 4,4′-bis (9-ethyl-3-carbazovinylene) 1,1′-biphenyl
  • TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene
  • ADN (9,10-di (2-naphthyl) anthracene
  • CBP 4,4′-bis (carbazole-9) -Yl) biphenyl
  • CDBP 4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl
  • fluorescent dopants examples include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium or thiapyrylium compound, fluorene derivative, perifuranthene derivative, indenoperylene derivative, Examples thereof include bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
  • phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.
  • dopants examples include Alq 3 (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) 3 ( And tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.
  • Examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes.
  • Examples of the alkali metal complex, alkaline earth metal complex, or earth metal complex include 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate).
  • a hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance.
  • Desirable compounds for the hole element layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).
  • an electron injection layer may be provided for the purpose of improving the electron injection property and improving device characteristics (for example, light emission efficiency, constant voltage driving, or high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. Is mentioned.
  • metal complexes alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO 2 , AlO, SiN, SiON, AlON, Various oxides such as GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C, and inorganic compounds such as nitride and oxynitride can also be used.
  • the cathode used in the present invention can be formed from any conductive material.
  • Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • the compound was identified by 1 H-NMR measurement and 13 C-NMR measurement.
  • the compound was identified by 1 H-NMR measurement and 13 C-NMR measurement.
  • the compound was identified by FDMS, 1 H-NMR measurement, and 13 C-NMR measurement.
  • the compound was identified by FDMS, 1 H-NMR measurement, and 13 C-NMR measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS, 1 H-NMR measurement, and 13 C-NMR measurement.
  • the compound was identified by FDMS, 1 H-NMR measurement, and 13 C-NMR measurement.
  • the compound was identified by FDMS and 1 H-NMR measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS, 1 H-NMR measurement, and 13 C-NMR measurement.
  • the compound was identified by FDMS measurement.
  • the compound was identified by FDMS, 1 H-NMR measurement, and 13 C-NMR measurement.
  • NPD 4,4′-bis [N- (1-naphthyl) -N-phenyl] biphenyl
  • Examples 17 to 30 (device evaluation) Instead of compound (D5), compound (F5), (B4), (C18), (D16), (E13), (G1), (H1), (J5), (K1), (N6), (P1 ), (Q1), (R4), or an organic EL device similar to that of Example 16 was produced except that it was changed to (S1).
  • Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
  • Comparative Examples 1 to 4 The same as Example 16, except that the compound (D5) was changed to 4,4′-bis (carbazol-9-yl) biphenyl (CBP), compound (a), compound (b) or compound (c). An organic EL element was produced. Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
  • the organic EL device containing the quinoxaline compound of the present invention having good bipolar properties can be expected to improve the recombination efficiency of electrons and holes in the light emitting layer. Therefore, the quinoxaline compound of the present invention can provide an organic EL device having high luminance and efficiency and excellent lifetime.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé de quinoxaline qui convient comme matériau luminescent de dispositifs EL organiques. On utilise un composé de quinoxaline représenté par la formule générale (I). R1-R5 et Z sont tels que décrits dans les revendications.
PCT/JP2017/007151 2016-02-29 2017-02-24 Composé de quinoxaline et utilisation de celui-ci WO2017150380A1 (fr)

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CN110483528A (zh) * 2019-07-04 2019-11-22 浙江华显光电科技有限公司 一种新型磷光主体化合物和使用该化合物的电致发光器件
CN112552282A (zh) * 2020-12-07 2021-03-26 浙江华显光电科技有限公司 一种有机化合物和使用该化合物的有机光电元件

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Publication number Priority date Publication date Assignee Title
CN110386925A (zh) * 2018-04-18 2019-10-29 祥德科技股份有限公司 用于有机发光元件的双极分子衍生物
CN110483528A (zh) * 2019-07-04 2019-11-22 浙江华显光电科技有限公司 一种新型磷光主体化合物和使用该化合物的电致发光器件
CN110483528B (zh) * 2019-07-04 2022-02-15 浙江华显光电科技有限公司 一种磷光主体化合物和使用该化合物的电致发光器件
CN112552282A (zh) * 2020-12-07 2021-03-26 浙江华显光电科技有限公司 一种有机化合物和使用该化合物的有机光电元件

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