WO2006103916A1 - Dispositif electroluminescent organique - Google Patents

Dispositif electroluminescent organique Download PDF

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Publication number
WO2006103916A1
WO2006103916A1 PCT/JP2006/304999 JP2006304999W WO2006103916A1 WO 2006103916 A1 WO2006103916 A1 WO 2006103916A1 JP 2006304999 W JP2006304999 W JP 2006304999W WO 2006103916 A1 WO2006103916 A1 WO 2006103916A1
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group
substituted
unsubstituted
carbon atoms
general formula
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PCT/JP2006/304999
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Japanese (ja)
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Takashi Arakane
Toshihiro Iwakuma
Mineyuki Kubota
Masakazu Funahashi
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Idemitsu Kosan Co., Ltd.
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Publication of WO2006103916A1 publication Critical patent/WO2006103916A1/fr

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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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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

Definitions

  • the present invention relates to an organic electoluminescence (EL) device, and more particularly to an organic EL device capable of obtaining red light emission with high color efficiency while having high luminous efficiency and long life.
  • EL organic electoluminescence
  • An organic EL element is a self-luminous element that utilizes the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied.
  • Tnag et al. Employ a layered structure using tris (8-quinolinol) aluminum for the light-emitting layer and triphenyldiamin derivative for the hole-transporting layer.
  • the advantages of the stacked structure are that the efficiency of hole injection into the light-emitting layer can be increased, the efficiency of excitons generated by recombination by blocking electrons injected into the cathode can be increased, and light emission For example, the excitons generated in the layer can be confined.
  • the device structure of an organic EL device is a two-layer type of a hole transport (injection) layer and an electron transport light-emitting layer, or a hole transport (injection) layer, a light-emitting layer, and an electron transport (injection) layer.
  • a three-layer structure is well known.
  • various improvements have been made to the element structure and formation method in order to increase the recombination efficiency of injected holes and electrons.
  • light-emitting elements used for organic EL elements light-emitting materials such as chelate complexes such as tris (8-quinolinol) aluminum complex, coumarin complexes, tetraphenylbutadiene derivatives, bisstyrinylene arylene derivatives, and oxaziazole derivatives are known. It has been reported that light emission in the visible region from blue to red can be obtained. Although the realization of a child is expected (for example, Patent Documents:! To 3 etc.), the luminous efficiency and lifetime have not reached a practical level and are insufficient. In addition, full-color displays require three primary colors (blue, green, and red), but high-efficiency red elements are particularly required.
  • chelate complexes such as tris (8-quinolinol) aluminum complex, coumarin complexes, tetraphenylbutadiene derivatives, bisstyrinylene arylene derivatives, and oxaziazole derivatives. It has been reported that light
  • Patent Document 4 discloses a red light emitting device in which a naphthacene or pentacene derivative is added to a light emitting layer.
  • this device is excellent in red purity, the half-life of the brightness when the applied voltage is as high as 1 IV is about 150 hours, which is insufficient.
  • Patent Document 5 discloses a device in which a dicyanomethylene (DCM) compound is added to a light emitting layer, but the red purity is insufficient.
  • Patent Document 6 discloses a red light-emitting device in which an amine-based aromatic compound is added to a light-emitting layer.
  • DCM dicyanomethylene
  • Patent Documents 7 and 8 disclose an element using an amine-based aromatic compound and Alq as a light emitting layer. This element emits red light but has low efficiency and a short life.
  • Patent Document 9 discloses a device using an amine-based aromatic compound and DPVDPAN (see the comparative example below for the chemical structure) in the light-emitting layer, but a highly efficient device emits red light and emits red light. The element to perform was low efficiency.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 8-239655
  • Patent Document 2 Japanese Patent Laid-Open No. 7-138561
  • Patent Document 3 Japanese Patent Laid-Open No. 3-200289
  • Patent Document 4 Japanese Patent Application Laid-Open No. 8-311442
  • Patent Document 5 Japanese Patent Laid-Open No. 3-162481
  • Patent Document 6 Japanese Unexamined Patent Publication No. 2001-81451
  • Patent Document 7 International Publication WO01Z23497
  • Patent Document 8 Japanese Patent Application Laid-Open No. 2003 — 40845
  • Patent Document 9 Japanese Unexamined Patent Application Publication No. 2003-81924
  • the present invention has been made to solve the above problems, and has high luminous efficiency and long life. Nevertheless, an object is to provide an organic EL device capable of emitting red light with high color purity.
  • an organic thin film layer that forms an organic EL element is (A) the following general formula (1) and / or (1 ') And a compound having (B) a condensed aromatic ring having a nuclear carbon number of 12 to 50 and an asymmetric structure.
  • the invention has been completed.
  • the present invention provides an organic EL device in which an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between a cathode and an anode, and at least one layer of the organic thin film layer comprises (A) Provided is an organic EL device comprising a compound represented by (1) and / or (1 ′) and (B) a compound having a condensed aromatic ring having 12 to 50 nuclear carbon atoms and an asymmetric structure It is.
  • Ai ⁇ Ar 4 is each independently a group represented by the following General Formula (2), (3) or (4). However, at least one of Ar 1 to Ar 4 is a group represented by the following general formula (2) or (3).
  • R 1 to R 3 are substituted or unsubstituted linear or branched alkyl groups having from 30 to 30 carbon atoms, and the rest are hydrogen atoms.
  • R 4 to R 6 is a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, and the remainder is a hydrogen atom.
  • R 7 ⁇ R U are each independently a hydrogen atom, a substituted or Mu ⁇ conversion linear or branched alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon atoms 1 50 alkoxy groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 50 nuclear carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 5 to 50 nuclear carbon atoms, substituted or unsubstituted nuclear carbon numbers A 5- to 50-aryloxy group, a substituted or unsubstituted aralkyl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, or a halogen atom.
  • R 7 to R may be bonded to each other in contact with P to form a saturated or unsaturated cyclic structure.
  • the organic EL device of the present invention can produce red light with high color purity while having high luminous efficiency and long life.
  • the organic EL device of the present invention is an organic electroluminescent device in which an organic thin film layer comprising a single layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode.
  • A a compound represented by the following general formula (1) and / or (1 ′)
  • B a compound having a condensed aromatic ring having 12 to 50 nuclear carbon atoms and an asymmetric structure .
  • 8 to 8 !: 4 are each independently a group represented by the following general formula (2), (3) or (4). However, at least one of Ar 1 to Ar 4 is a group represented by the following general formula (2) or (3).
  • At least two of R 1 to are substituted or unsubstituted linear or branched alkyl groups having from 30 to 30 carbon atoms, and the remainder is a hydrogen atom.
  • at least two of R 1 to R 3 are each independently a methinole group, an ethyl group, an isopropylinole group, a 1_butyl group, a 2_methylpropyl group, or 1,1-dimethylethyl.
  • a group, dimethyl group or trimethyl group is preferred.
  • R 1 ⁇ examples of the alkyl group of R 3 include, for example, a methinole group, an ethyl group, a propyl group, an isopropylinole group, an n_butyl group, an s_butyl group, an isobutyl group, a t_butyl group, an n_ Pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1 , 3 Dihydroxyisopropyl group, 2,3 dihydroxy-t-butyl group, 1,2,3 trihydroxypropyl group, chloromethyl group, 1 chloroethyl group, 2 chloroethyl group, 2 chloroethyl isobutyl group, 1,2 dichloro Diethyl group
  • a methyl group, an ethyl group, an isopropyl group, a 1-butyl group, a 2-methylpropyl group, a 1,1-dimethylethyl group, a dimethyl group, and a trimethyl group are preferable.
  • At least one of R 4 to R 6 is a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, and the remaining is a hydrogen atom.
  • at least one of R 4 to R 6 is preferably a cyclohexyl group.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1_norbornyl group, and a 2_norbornyl group. And a cyclohexyl group is preferable.
  • R 7 ⁇ R U are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 50 carbon atoms substituted or Mu ⁇ conversion, a substituted or unsubstituted carbon
  • the alkyl group for R 7 to R U for example, a methyl group, Echiru group, propyl group, isopropyl Pinore group, n_ butyl group, s_ butyl group, an isobutyl group, t_ butyl group, n_ pentyl Group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1, 3-dihydroxyisopropyl group, 2,3-dihydroxyt-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1_chloroethyl group, 2_chloroethylol group, 2_chloroisobutyl group Group, 1,2-Dichlorodiethyl group, 1,3-Dicyclodiethy
  • R 7 ⁇ The alkoxy group of R 11 is a group represented by 10 Y, and examples of ⁇ include the same examples as those described for the alkyl group.
  • Examples of the aromatic hydrocarbon group represented by R 7 to R U include a phenyl group, a 1_naphthyl group, a 2_naphthyl group, a 1_anthrinol group, a 2_anthrinol group, a 9 anthryl group, and a 9- (10-phenolo group.
  • Examples of the aromatic heterocyclic group represented by R 7 to R U include 1_pyrrolyl group, 2_pyrrolyl group, 3_pyrrolyl group, pyradyl group, 2_pyridinyl group, 1_imidazolyl group, 2_imidazolyl group, 1 —Pyrazolinole group, 1_Indolizinyl group, 2_Indolizinyl group, 3_Indolizinyl group, 5-Indolizinyl group, 6-Indolizinyl group, 7-Indolizinyl group, 8-Indolizinyl group, 2Imidazopyridinyl group, 3Imidazopyridinyl group Group, 5 imidazopyridinyl group, 6 imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4 pyridinyl group, 1 indolinole group, 2 indolinole
  • the aryloxy group of R 7 to R ′′ is represented as OY ′, and examples of Y ′ include the same examples as the aromatic hydrocarbon group and aromatic heterocyclic group.
  • Examples of the aralkyl group of R 7 to R ′′ include, for example, benzyl group, 1 phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-tbutyl group, ⁇ -naphthylmethyl group 1 ⁇ -naphthylethyl, 2 a-naphthylethyl, 1 ⁇ -naphthylisopropyl, 2 a-naphthylisopropyl, ⁇ -naphthylmethyl, 1 _ ⁇ -naphthylethyl, 2- ⁇ -naphthylethyl, 1- ⁇ -naphthyl Isopropyl group, 2- ⁇ -naphthylisopropyl group, 1_pyrrolylmethyl group, 2_ (1_pyrrolyl) ethy
  • R 7 ⁇ examples of the cycloalkyl group R 11, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4 hexyl group methylcyclohexyl, 1-Adamanchi group, 2-Adamanchiru group, 1 _ norbornyl Group, 2_norbornyl group and the like.
  • Examples of the halogen atom of R 7 to R U for example, a fluorine atom, a chlorine atom, a bromine atom and an ® ⁇ iodine atom.
  • R 7 to R U may be bonded to each other in contact with P to form a saturated or unsaturated cyclic structure.
  • cyclic structure examples include, for example, cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, cyclobutene, cyclobenten, cyclohexene, cycloheptene, and cyclootaten.
  • examples include 50 aromatic rings, heterocyclic rings having 5 to 50 carbon atoms such as imidazole, pyrrole, furan, thiophene and pyridine.
  • a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms a substituted or unsubstituted nuclear atom number of 5 to 50 Aromatic heterocyclic group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms Group, substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted Examples thereof include a substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted
  • Examples of the condensed aromatic ring having 12 to 50 nuclear carbon atoms include anthracene, phenanthrene, pyrene, taricene, triphenylene, perylene and the like, and anthracene and pyrene are preferable.
  • the condensed aromatic ring-containing compound has an asymmetric structure.
  • it is represented by an asymmetric anthracene derivative represented by the following general formula (5), an asymmetric anthracene derivative represented by the general formula (6), or a general formula (7).
  • Preferred examples include asymmetric pyrene derivatives and asymmetric diphenylanthracene derivatives represented by the general formula (8).
  • X represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic group having 5 to 50 nuclear atoms.
  • Ar 51 and Ar 52 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms, and at least one of Ar 51 and Ar 52 is represented by the following general formula (i): 1_naphthyl group or 2_naphthyl group represented by the following general formula ( ⁇ ). [0028] [Chemical 8]
  • R 51 to R 57 are a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one pair of adjacent R 51 to R 57 is These are bonded together to form a ring structure.
  • a, b and c are each an integer of 0 to 4, and d is an integer of 1 to 3.
  • d is 2 or more, the groups in [] may be the same or different.
  • Examples of the aromatic hydrocarbon group, aromatic heterocyclic group, alkyl group, cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, aralkyl group, and aryloxy group of X include same examples as those mentioned R 7 to R U in the general formula (4) below.
  • the arylthio group of X is represented by —SY ′, and examples of Y ′ include the same examples as the aromatic hydrocarbon group and aromatic heterocyclic group.
  • the alkoxycarbonyl group of X is a group represented by _C0OY, and examples of Y include the same examples as those described above for the alkyl group.
  • Examples of the silyl group of X include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a butyldimethylsilyl group, and a propyldimethylsilyl group.
  • Examples of the condensed aromatic ring group of Ar 51 and Ar 52 include naphthalene, anthracene, phenanthrene, pyrene, taricene, triphenylene, perylene and the like.
  • Examples of the alkyl group of R 51 to R 57 include the same examples as those described for R 7 to R ′′ in the general formula (4).
  • Examples of the cyclic structure formed by R 51 to R 57 include Examples thereof include cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane and norbornane.
  • a 61 and A 62 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 nuclear carbon atoms.
  • Ar 61 and Ar 62 are each independently a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms.
  • R 61 to R 7 ° each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
  • Ar 61 , Ar 62 , R 69 and R TM may be plural or adjacent to each other to form a saturated or unsaturated cyclic structure.
  • Examples of the condensed aromatic ring of A 61 and A 62 include the examples given for Ar 51 and Ar 52 in the general formula (5). Among them, the ones with suitable carbon numbers are listed.
  • Examples of each group of Ar 61 , Ar 62 and R 61 to R 7Q , and examples of the cyclic structure that Ar 61 , Ar 62 , R 69 and R 7 ° may form include those represented by the general formula (4). Examples similar to those mentioned are given.
  • Ar and Ar ′ are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 50 nuclear carbon atoms, or substituted or unsubstituted aromatic heterocyclic rings having 5 to 50 nuclear atoms, respectively. It is a group.
  • L and L ′ are each a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group.
  • n is an integer from 1 to 4
  • s is an integer from 0 to 2
  • t is an integer from 0 to 4.
  • L or Ar is bonded to any one of 1 to 5 positions of pyrene
  • L ′ or Ar is bonded to any of 6 to 10 positions of pyrene.
  • Examples of the aromatic hydrocarbon group and aromatic heterocyclic group for Ar and Ar ′ include the same examples as those given in the general formula (5).
  • R 81 to R 9 ° each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms.
  • each group of Ar 81 , Ar 82 and R 81 to R 9Q include the same examples as those given in the general formula (5).
  • the substituents of the groups of the general formulas (5) to (8) are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 50 nuclear carbon atoms, substituted or unsubstituted nuclear atoms.
  • substituted or unsubstituted alkyl group having 1 to 50 carbon atoms substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted carbon number 1 to 50
  • a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms examples thereof include a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxyl group.
  • the organic thin film layer contains the compound represented by the general formula (1):! To 70% by weight, more preferably! To 20% by weight. .
  • the compound of the component (A) which is preferably contained when the light emitting layer contains the compound of the component (A) and the compound of the component (B) is a dopant, More preferably, the compound of component (B) is a host material.
  • a compound having a condensed aromatic ring having 12 to 50 nuclear carbon atoms and having an asymmetric structure, such as component (B), particularly a compound having a specific terminal substituent as described above, is steric hindrance between compounds. As a result, the concentration quenching due to molecular association can be prevented and the lifetime can be further extended, so that red emission with high color purity can be obtained while having high emission efficiency and long lifetime.
  • the red emission color of organic EL elements can be divided by the maximum emission wavelength of the emission spectrum, orange (585 to 595 nm), red (maximum emission wavelength: 595 to 620 nm), pure red (maximum emission wavelength: 620). ⁇ 700nm).
  • red light emission means that CIEx value in CIE chromaticity coordinates is 0.62 or more (preferably 0.62 or more and less than 0.73), orange Luminescence is a CIEx value between 0 ⁇ 54 and less than 0 ⁇ 62.
  • various intermediate layers are preferably interposed between the pair of electrodes and the light emitting layer.
  • the intermediate layer include a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.
  • the force for which the configuration of (8) is preferably used is not limited to these.
  • This organic EL element is usually produced on a translucent substrate.
  • This translucent substrate is a substrate that supports organic EL elements, and the translucency is 50 for light in the visible region of 400 to 700 nm. It is preferable to use a smoother substrate that is more than / o.
  • a translucent substrate for example, a glass plate, a synthetic resin plate, or the like is preferably used.
  • glass plates include soda-lime glass, glass containing strontium, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the synthetic resin plate include polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, and polysulfone resin.
  • anode a material having a large work function (4 eV or more) metal, alloy, electrically conductive compound or a mixture thereof is preferably used.
  • electrode materials include metals such as Au, Cul, IT ⁇ (indium tinoxide), Sn ⁇ ,
  • Examples include conductive materials such as ZnO and In-Zn-O.
  • a thin film can be formed from these electrode materials by a method such as vapor deposition or sputtering.
  • the anode desirably has such a characteristic that when light emitted from the light emitting layer is extracted from the anode, the transmittance for light emission from the anode is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ or less.
  • the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to l x m, preferably 10 to 200 nm.
  • the cathode those having a low work function, (4 eV or less) metal, an alloy, an electrically conductive compound, and a mixture thereof as an electrode material are used.
  • electrode materials are sodium, sodium-potassium alloy, magnesium, lithium, magnesium silver alloy, aluminum / aluminum oxide, Al / Li 0, Al / LiO, Al / LiF, aluminum.
  • Examples include lithium alloys, indium, and rare earth metals.
  • This cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the transmittance for the light emission of the cathode is preferably larger than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / b or less, and the film thickness is usually 10 nm to l zm, preferably 50 to 200 nm.
  • a chalcogenide layer is formed on at least one surface of the pair of electrodes thus prepared. These are sometimes referred to as surface layers).
  • a chalcogenide (including oxide) layer of metal such as silicon or aluminum is formed on the anode surface on the light emitting layer side, and a metal halide layer or metal oxide layer is formed on the cathode surface on the light emitting layer side. It is good to arrange. Thereby, the drive can be stabilized.
  • Preferred examples of the chalcogenide include SiOx (l ⁇ X ⁇ 2), AlOx (l ⁇ X ⁇ 1.5), Si ON, SiAlON, etc.
  • examples of the metal halide include LiF, MgF
  • the metal oxide examples include Cs.
  • both the electron transport property and the hole transport property of the light emitting layer are improved by the use ratio of the component (A) and the component (B). It is possible to omit intermediate layers such as layers, hole transport layers, and electron injection layers.
  • the surface layer can be provided also in this case and is preferable.
  • the mixed region of the electron transfer compound and the reducing dopant or the mixed region of the hole transfer compound and the oxidizing dopant is formed on at least one surface of the pair of electrodes thus prepared.
  • the electron transfer compound is reduced and becomes an anion, and the mixed region more easily injects and transfers electrons to the light emitting layer.
  • the hole transfer compound is oxidized and becomes a cation, so that the mixed region more easily injects and transfers holes to the light emitting layer.
  • a preferable oxidizing dopant there are various Lewis acid acceptor compounds.
  • Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and their compounds.
  • the light emitting layer is
  • Injection function function that can inject holes from the anode or hole injection layer when an electric field is applied, and can inject electrons from the negative electrode or electron injection layer
  • Transport function Function to move injected charges (electrons and holes) by the force of electric field
  • Luminescent function provides a field for recombination of electrons and holes, and has a function to connect this to light emission.
  • the light emitting layer is particularly preferably a molecular deposited film.
  • the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state.
  • This molecular deposited film has an agglomerated structure and a high structure compared to the thin film (molecular accumulation film) formed by the LB method It can be classified by the difference in the next structure and the functional difference resulting therefrom.
  • a binder such as a resin and a material compound are dissolved in a solvent to form a solution, which is then thin-filmed by spin coating or the like.
  • the light emitting layer can also be formed by annealing.
  • the light emitting layer may contain other known light emitting materials other than the component (A) and the component (B).
  • a light emitting layer containing another known light emitting material may be laminated on the light emitting layer containing the compound according to the present invention.
  • the hole injecting / transporting layer is a layer that helps injecting holes into the light emitting layer and transports them to the light emitting region, and has a high hole mobility and usually has an ion energy of 5.5 eV or less. And small les.
  • a material that transports holes to the light-emitting layer with a lower electric field strength is preferred.
  • the mobility force of holes is small, for example, when an electric field of 10 4 to 10 6 VZcm is applied. even without those which are 10- 6 cm 2 / V * s is preferable.
  • a material that has been conventionally used as a hole transport material in an optical material, or a known medium-powered material used for a hole injection layer of an organic EL element is selected. Can be used.
  • the hole injection' transport material may be formed into a thin film by a known method such as vacuum deposition, spin coating, casting, or LB. ,.
  • the thickness of the hole injecting / transporting layer is not particularly limited, but is usually 5 nm to 5 ⁇ m.
  • the electron injection layer 'transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility
  • the adhesion improving layer is the electron injection layer.
  • it is a layer made of a material that particularly adheres well to the cathode.
  • the material used for the electron injection layer is preferably a metal complex of 8-hydroxyquinoline or a derivative thereof.
  • metal complexes of 8-hydroxyquinoline or its derivatives include metal chelate oxinoid compounds containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline) such as tris (8-quinolinol) aluminum. It can be used as an electron injection material.
  • a chelate of oxine generally 8-quinolinol or 8-hydroxyquinoline
  • 8-quinolinol 8-hydroxyquinoline
  • tris (8-quinolinol) aluminum 8-quinolinol
  • 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, oxidizing power, subsequentlyium, calcium fluoride, aluminum nitride, Examples thereof include titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. A mixture or laminate of these may be used.
  • an anode for example, an anode, a light emitting layer, a hole injection layer as necessary, and an electron injection layer as necessary are formed by the above-described materials and methods.
  • a cathode may be formed on the substrate.
  • the organic EL element can be fabricated in the reverse order from the cathode to the anode.
  • a thin film having an anode material strength is formed on a suitable translucent substrate by vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm, and used as an anode.
  • a hole injection layer is provided on the anode.
  • the hole injection layer can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. A homogeneous film can be obtained immediately and pinholes are not easily generated. In view of the above, it is preferable to form the film by a vacuum evaporation method.
  • the deposition conditions vary depending on the compound used (material of the hole injection layer), the crystal structure and recombination structure of the target hole injection layer, etc.
  • a light emitting layer is provided on the hole injection layer.
  • This light-emitting layer is also formed by thinning the film using a material comprising the compounds of the components (A) and (B) according to the present invention by a method such as vacuum deposition, sputtering, spin coating, or casting.
  • a method such as vacuum deposition, sputtering, spin coating, or casting.
  • vacuum deposition from the standpoint that a homogeneous film is obtained and pinholes are not easily generated. It is preferable.
  • the deposition conditions vary depending on the compound used, but in general, it is possible to select from the same condition range as the formation of the hole injection layer.
  • the film thickness is preferably in the range of 10 to 40 nm.
  • an electron injection layer is provided on the light emitting layer. Also in this case, like the hole injection layer and the light emitting layer, it is preferable to form by a vacuum evaporation method because it is necessary to obtain a homogeneous film.
  • the vapor deposition conditions can be selected from the same condition ranges as those for the hole injection layer and the light emitting layer.
  • the cathode is made of metal, and vapor deposition or sputtering can be used. However, vacuum deposition is preferred to protect the underlying organic layer from damage during film formation.
  • the above organic EL device is preferably manufactured from the anode to the cathode consistently by a single vacuum.
  • a transparent electrode made of indium oxide having a thickness of 120 nm was provided on a 7 mm size glass substrate. This glass substrate was ultrasonically cleaned in isopropyl alcohol for 5 minutes, then UV ozone cleaned for 30 minutes, and this substrate was placed in a vacuum evaporation system.
  • ⁇ ⁇ ', ⁇ "—bis [4- (diphenylamino) phenol] - ⁇ ', ⁇ "-diphenylbiphenyl4,4'-diamin is added to the substrate as a hole injection layer at 60 nm.
  • the following compound (B) -1 as a host material and the following compound (A) -5 as a dopant were co-deposited at a weight ratio of 40: 4, and then deposited to a thickness of 40 nm.
  • tris (8-hydroxyquinonato) aluminum hereinafter referred to as Alq is used as an electron injection layer.
  • An organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Table 1 were used as the host material and dopant of the light emitting layer.
  • the compounds used in Examples 2 to 8 shown in Table 1 are shown below.
  • the obtained device was energized at a current density of 10 mA / cm 2 in the same manner as in Example 1.
  • Table 1 shows the results of a DC continuous energization test with an initial luminance of 5000 cd / m 2 .
  • An organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Table 1 were used as the host material and dopant of the light emitting layer.
  • the compounds used in Comparative Examples 1 to 10 shown in Table 1 are shown below.
  • the obtained device was subjected to an energization test at a current density of 10 mA / cm 2 in the same manner as in Example 1, and the results of a DC continuous energization test with an initial luminance of 5000 cd / m 2 are shown in Table 1.
  • the organic EL device of the present invention can emit red light with high color purity while having high luminous efficiency and long life. Therefore, it is useful as a practical organic EL device, and is particularly suitable for a full-color display.

Abstract

L’invention concerne un dispositif électroluminescent organique où un film mince organique composé d’une ou plusieurs couches comprenant au moins une couche émettrice de lumière est interposé entre une cathode et une anode, et au moins une couche dans le film mince organique contient un composé (A) ayant un substituant terminal spécifique et un composé (B) de structure asymétrique qui a un cycle aromatique fondu ayant de 12 à 50 atomes de carbone nucléaires. Ce dispositif électroluminescent organique est capable d’émettre une lumière rouge de pureté de couleur élevée tout en ayant une efficacité lumineuse élevée et une longue vie.
PCT/JP2006/304999 2005-03-25 2006-03-14 Dispositif electroluminescent organique WO2006103916A1 (fr)

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KR100901887B1 (ko) * 2008-03-14 2009-06-09 (주)그라쎌 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광소자

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WO2003010127A1 (fr) * 2001-07-23 2003-02-06 Petroleum Energy Center, A Juridical Incorporated Foundation Composes aromatiques et dispositifs electroluminescents organiques fabriques a l'aide de ces derniers
WO2004018587A1 (fr) * 2002-08-23 2004-03-04 Idemitsu Kosan Co., Ltd. Dispositif organique electroluminescent et derive d'anthracene
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WO2005081587A1 (fr) * 2004-02-19 2005-09-01 Idemitsu Kosan Co., Ltd. Dispositif électroluminescent organique de couleur blanche
WO2005086539A1 (fr) * 2004-03-05 2005-09-15 Idemitsu Kosan Co., Ltd. Dispositif d’affichage à électroluminescence organique
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JP2000273056A (ja) * 1999-01-19 2000-10-03 Idemitsu Kosan Co Ltd アミノ又はスチリル化合物及びそれを用いた有機エレクトロルミネッセンス素子
WO2001023497A1 (fr) * 1999-09-30 2001-04-05 Idemitsu Kosan Co., Ltd. Element electroluminescent organique
WO2003010127A1 (fr) * 2001-07-23 2003-02-06 Petroleum Energy Center, A Juridical Incorporated Foundation Composes aromatiques et dispositifs electroluminescents organiques fabriques a l'aide de ces derniers
WO2004018587A1 (fr) * 2002-08-23 2004-03-04 Idemitsu Kosan Co., Ltd. Dispositif organique electroluminescent et derive d'anthracene
WO2005011333A1 (fr) * 2003-07-28 2005-02-03 Idemitsu Kosan Co., Ltd. Element electroluminescent organique a lumiere blanche
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WO2009008199A1 (fr) * 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. Dérivé de naphtalène, matière pour élément électroluminescent organique et élément électroluminescent organique utilisant la matière
WO2009008198A1 (fr) * 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. Dérivé de naphtalène, matière pour un élément électroluminescent organique, et élément électroluminescent organique utilisant la matière
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US8025815B2 (en) 2007-07-07 2011-09-27 Idemitsu Kosan Co., Ltd. Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same

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