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WO2010058787A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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Publication number
WO2010058787A1
WO2010058787A1 PCT/JP2009/069543 JP2009069543W WO2010058787A1 WO 2010058787 A1 WO2010058787 A1 WO 2010058787A1 JP 2009069543 W JP2009069543 W JP 2009069543W WO 2010058787 A1 WO2010058787 A1 WO 2010058787A1
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group
layer
light emitting
general formula
electron
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Japanese (ja)
Inventor
和幸 柴田
弥 外山
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Fujifilm Corp
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Fujifilm Corp
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Priority to EP09827568A priority Critical patent/EP2360752A4/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • 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
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/166—Electron transporting layers comprising a multilayered structure
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates to an organic electroluminescent device (hereinafter sometimes referred to as an organic EL device) which can be effectively used for a full color display, a backlight, a surface light source such as an illumination light source, a light source array such as a printer.
  • an organic electroluminescent device hereinafter sometimes referred to as an organic EL device
  • a surface light source such as an illumination light source
  • a light source array such as a printer.
  • An organic EL element is comprised from the several organic compound layer containing a light emitting layer or a light emitting layer, and the counter electrode which pinched
  • electrons injected from the cathode and holes injected from the anode are recombined in the organic compound layer, light emission from the generated excitons, and other energy generated by energy transfer from the excitons It is an element for obtaining light emission utilizing at least one of light emission from excitons of a molecule.
  • the organic EL device has been greatly improved in luminance and device efficiency by using a laminated structure with separated functions.
  • a two-layer stacked device in which a hole transporting layer and a light emitting / electron transporting layer are stacked
  • a three-layer stacked device in which a hole transporting layer, a light emitting layer and an electron transporting layer are stacked
  • a hole transporting layer, a light emitting layer A four-layer stacked element in which a hole blocking layer and an electron transporting layer are stacked is often used.
  • a configuration is disclosed in which a hole blocking layer doped with an electron donative metal complex such as BAlq or Alq is provided at the interface of the light emitting layer facing the cathode, and it is considered that light emission with high luminance is obtained at low driving voltage.
  • an electron donative metal complex such as BAlq or Alq
  • the structure has an electron transporting layer, and a mixed layer containing the electron transporting material of the electron transporting layer and the electron donating material between the electron transporting layer and the cathode. It is disclosed that the light emission efficiency is improved (see, for example, Patent Document 2).
  • An object of the present invention is to provide an organic EL element having high luminous efficiency, low driving voltage and excellent driving durability.
  • An organic electroluminescent device comprising: at least a light emitting layer between a pair of electrodes; a first electron transport layer provided in contact with the cathode side interface of the light emitting layer; and a cathode of the first electron transport layer Sandwiching an organic compound layer including a second electron transport layer provided in contact with the side interface, the light emitting layer containing at least a light emitting material represented by the following general formula (1) and a hole transporting host material;
  • the second electron transport layer is at least one selected from the group consisting of an electron transport material represented by the following general formula (ET), an alkali metal, an alkali metal salt, an alkaline earth metal, and an alkaline earth metal salt
  • An organic electroluminescent device containing at least a species.
  • each of A C1 to A C14 independently represents C—R or N.
  • R represents a hydrogen atom or a substituent.
  • L C1 represents a single bond or a divalent linking group .
  • R 1 represents a hydrogen atom, or a substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, n represents an integer of 0 to 8. When n is an integer of 2 or more, plural R 1 s may be the same as or different from each other)
  • the organic electroluminescent element as described in ⁇ 1> whose compound represented by ⁇ 2> said General formula (1) is a compound represented by following General formula (2).
  • a C15 and A C16 each independently represent C—R or N.
  • R represents a hydrogen atom or a substituent.
  • R C1 to R C16 represent a hydrogen atom or a substituent.
  • At least one selected from the group consisting of alkali metals, alkali metal salts, alkaline earth metals and alkaline earth metal salts is Li, Cs, Ca, LiF, NaF, KF, RbF, CsF, MgF 2 , CaF 2 , SrF 2 , BaF 2 , LiCl, NaCl, KCl, RbCl, CsCl, MgCl 2 , CaCl 2 , CaCl 2 , SrCl 2 , BaCl 2 , LiHCO 3 , NaHCO 3 , KHCO 3 , RbHCO 3 , CsHCO 3 , Li 2
  • the ratio of the total amount of the alkali metal, the alkali metal salt, the alkaline earth metal and the alkaline earth metal salt to the electron transporting material represented by the general formula (ET) in the second electron transporting layer is The organic electroluminescent device according to any one of ⁇ 1> to ⁇ 3>, which is 0.1% by mass or more and 2.0% by mass or less.
  • an organic EL element having high luminous efficiency and low driving voltage and excellent in driving durability is provided.
  • the organic EL device of the present invention comprises at least a light emitting layer, a first electron transporting layer provided in contact with the cathode side interface of the light emitting layer, and a cathode side interface of the first electron transporting layer between a pair of electrodes.
  • An electron transporting layer includes an electron transporting material represented by the following general formula (ET), and at least one selected from the group consisting of an alkali metal, an alkali metal salt, an alkaline earth metal, and an alkaline earth metal salt It is an organic electroluminescent element containing at least.
  • each of A C1 to A C14 independently represents C—R or N.
  • R represents a hydrogen atom or a substituent.
  • L C1 represents a single bond or a divalent linking group.
  • R 1 represents a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms
  • n represents an integer of 0 to 8.
  • n is an integer of 2 or more, plural R 1 s may be the same as or different from each other.
  • At least one of the anode and the cathode is preferably transparent or translucent.
  • a hole transport layer, a light emitting layer, a first electron transport layer, and a second electron transport layer are laminated in order from the anode side.
  • a charge blocking layer or the like may be provided between the hole transport layer and the light emitting layer, or between the light emitting layer and the electron transport layer.
  • a hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer.
  • Each layer may be divided into a plurality of secondary layers.
  • each of A C1 to A C14 independently represents C—R or N.
  • C—R represents that a carbon atom is a ring-constituting atom, and R is a hydrogen atom or a substituent to the carbon atom.
  • Each of A C1 to A C6 independently represents C—R or N.
  • R represents a hydrogen atom or a substituent.
  • an alkyl group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 10), for example, methyl, ethyl, iso-propyl, tert-Butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl etc., alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly The carbon number is preferably 2 to 10, and examples thereof include vinyl, allyl, 2-butenyl, 3-pentenyl and the like, and an alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably It preferably has 2 to 10 carbon atoms and, for example, propargyl, 3-pentynyl and the like can be
  • An alkoxy group preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 10, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like
  • Aryloxy group preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably 6 to 12 carbon atoms, such as phenyl, 1-naphthyloxy, 2-naphthyloxy.
  • Heterocyclic oxy group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like), acyl A group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples include acetyl, benzoyl, formyl, pivaloyl and the like), an alkoxycarbonyl group (preferably Is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl and ethoxycarbonyl), aryloxycarbonyl groups (preferably 7 carbon atoms).
  • acyl A group preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a
  • -30 more preferably 7 to 20 carbon atoms, particularly preferably 7 to 1 carbon atoms And includes, for example, phenyloxycarbonyl and the like), an acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, for example, acetoxy, benzoyloxy And the like), an acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples include acetylamino and benzoylamino).
  • an acyloxy group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, for example, acetoxy, benzoyloxy And the like
  • an acylamino group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon
  • An alkoxycarbonylamino group (preferably having a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 2 to 12, and examples thereof include methoxycarbonylamino and the like), an aryloxycarbonylamino group (Preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably Or a carbon number of 7 to 12, and examples thereof include phenyloxycarbonylamino and the like), and a sulfonylamino group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number 1 to 12, and examples thereof include methanesulfonylamino, benzenesulfonylamino and the like),
  • a sulfamoyl group (preferably having a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, particularly preferably a carbon number of 0 to 12, and examples thereof include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl and the like
  • Carbamoyl group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like).
  • An alkylthio group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples include methylthio, ethylthio and the like), an arylthio group (preferably Has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, It preferably has 6 to 12 carbon atoms, and examples thereof include phenylthio and the like), heterocyclic thio groups (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • examples thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, a sulfonyl group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 30). And particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl), sulfinyl groups (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 carbon atoms). To 12, and examples thereof include methanesulfinyl, benzenesulfinyl and the like),
  • Ureido group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples include ureide, methyl ureido and phenyl ureido), phosphoric acid amide A group (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and particularly preferably a carbon number of 1 to 12, and examples thereof include diethyl phosphoric acid amide and phenyl phosphoric acid amide); Mercapto group, halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably Is a carbon number of 1 to 30, more preferably a carbon number of 1 to 12, and as
  • R is preferably a hydrogen atom, an alkyl group, an aryl group, a fluorine group, a cyano group or an amino group, and more preferably a hydrogen atom or a fluorine group.
  • AC 1 to AC 6 are preferably C—R.
  • AC 1 to AC 6 are preferably C—R, and R may be connected to each other to form a ring.
  • R preferably is a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group or a cyano group as R of A C2 and A C5 And more preferably a hydrogen atom, an amino group, an alkoxy group, an aryloxy group or a fluorine group, particularly preferably a hydrogen atom or a fluorine group, preferably as R of A C1 , A C3 , A C4 and A C6 A hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group or a cyano group, more preferably a hydrogen atom, an amino group, an alkoxy group, an aryloxy group or a fluorine group,
  • the number of N (representing a nitrogen atom) in each of AC 7 to AC 10 and AC 11 to AC 14 as AC 7 to AC 14 is preferably 0 to 2, and more preferably 0 to 1.
  • N is preferably selected from A C8 ⁇ A C10 and A C12 ⁇ A C14, more preferably selected from A C8, A C9, A C12 , A C13, selected from A C8, A C12 are particularly preferred.
  • a C7 to A C14 represents C—R
  • a hydrogen atom, an alkyl group, a fluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group is preferable as R of A C8 and A C12 Or a cyano group, more preferably a hydrogen atom, a fluoroalkyl group, an alkyl group, an aryl group, a fluorine group or a cyano group, particularly preferably a hydrogen atom, a polyfluoroalkyl group or a cyano group.
  • a C7, A C9, A C11 , or preferably as R represented by A C13 is a hydrogen atom, an alkyl group, fluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group, or a cyano group, More preferably, they are a hydrogen atom, a fluoroalkyl group, a fluorine group or a cyano group, and particularly preferably a hydrogen atom or a fluorine group.
  • R represented by A C10 and A C14 a hydrogen atom or a fluorine group is preferable, and a hydrogen atom is more preferable.
  • R's may be linked to each other to form a ring.
  • L C1 represents a single bond or a divalent linking group.
  • Examples of the divalent linking group represented by L C1 include an alkylene group (methylene, ethylene, propylene etc.), an arylene group (phenylene, naphthalenediyl), a heteroarylene group (pyridine diyl, thiophenediyl etc.), an imino group (- NR-) (phenylimino group etc.), oxy group (-O-), thio group (-S-), phosphinidene group (-PR-) (phenyl phosphinidene group etc.), silylene group (-SiRR'-) (Dimethylsilylene group, diphenylsilylene group, etc.) or a combination thereof.
  • These linking groups may further have a substituent.
  • L C1 is preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group, or a silylene group, more preferably a single bond, an alkylene group, an arylene group, an imino group, More preferably, it is an alkylene group, more preferably a methylene group, still more preferably a disubstituted methylene group, and still more preferably a dimethylmethylene group, a diethylmethylene group, a diisobutylmethylene group, a dibenzylmethylene group, an ethylmethylmethylene A methyl propyl methylene group, an isobutyl methyl methylene group, a diphenyl methylene group, a methyl phenyl methylene group, a cyclohexane diyl group, a cyclopentane diyl group, a fluorenedi
  • a compound represented by the following general formula (2) is preferable.
  • a C15 and A C16 each independently represent C—R or N.
  • C—R represents that a carbon atom is a ring-constituting atom, and R is a hydrogen atom or a substituent to the carbon atom.
  • R C1 to R C16 represent a hydrogen atom or a substituent.
  • AC15 and AC16 each independently represent CR or N.
  • a C15 and A C16 represent C—R
  • a hydrogen atom, an alkyl group, a fluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group is preferable as R of A C15 and A C16
  • R C1 to R C16 represent a hydrogen atom or a substituent.
  • R C1 to R C6 are preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group or a cyano group, more preferably a hydrogen atom, an amino group, an alkoxy group or an aryloxy group A fluorine group, particularly preferably a hydrogen atom or a fluorine group, and particularly preferably a hydrogen atom.
  • R C7 , R C9 , R C11 and R C13 are preferably a hydrogen atom, an alkyl group, a fluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine group, a cyano group, more preferably a hydrogen atom A fluoroalkyl group, a fluorine group or a cyano group, particularly preferably a hydrogen atom or a fluorine group.
  • Each of R C10 and R C14 is preferably a hydrogen atom or a fluorine group, and more preferably a hydrogen atom.
  • R C15 and R C16 a hydrogen atom, methyl group, ethyl group, propyl group, butyl group, fluoromethyl group, fluorine group, isobutyl group, benzyl group, phenyl group, R C15 and R C16 are preferably linked to form a cyclohexane ring.
  • R 15 and R 16 are connected to form a cyclopentane ring, R 15 and R 16 are connected to form a fluorene ring, and more preferably a methyl group, an ethyl group and an isobutyl group.
  • There is a group which forms a cyclohexane ring linked particularly preferably a methyl group, a phenyl group.
  • the compounds represented by the general formula (1) or the general formula (2) may be used alone or in combination of two or more.
  • the mixing ratio thereof is preferably 0.1: 99.9 to 99.9: 0.1 by mass ratio. It is preferably in the range of 1:99 to 99: 1.
  • the light emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer having a function of providing light and emitting light.
  • the light emitting layer in the present invention contains a light emitting material as a compound represented by the general formula (1) or the general formula (2), and contains a hole transport host material as a host material.
  • the light emitting layer in the present invention may further contain other phosphorescent light emitting materials and fluorescent light emitting materials as a light emitting material, or may contain an electron transporting host material as a host material. good.
  • the thickness of the light emitting layer in the present invention is not particularly limited, but is usually 1 nm to 500 nm, preferably 2 nm to 200 nm, more preferably 3 nm to 100 nm.
  • Light Emitting Material As the light emitting material, a compound represented by the general formula (1) or the general formula (2) is used, but other fluorescent light emitting material and phosphorescent light emitting material can be used in combination. In addition, for the purpose of promoting energy transfer from the host material, methods disclosed in Japanese Patent Application Laid-Open Nos. 2007-290748 and 2008-089843 can also be used.
  • (A) Phosphorescent light-emitting material Generally as a phosphorescence light-emitting material, the metal complex containing a transition metal atom or a lanthanoid atom can be mentioned. Transition metal atoms preferably include ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium and platinum, more preferably rhenium, iridium and platinum, and still more preferably iridium and platinum. .
  • lanthanoid atoms examples include lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutesium.
  • neodymium, europium and gadolinium are preferred.
  • halogen ligands preferably chlorine ligands
  • aromatic carbocyclic ligands for example, cyclopentadienyl anions, benzene anions, naphthyl anions, etc.
  • Nitrogen-containing heterocyclic ligands eg, phenylpyridine, benzoquinoline, quinolinol, bipyridyl, phenanthroline, etc.
  • diketone ligands eg, acetylacetone, etc.
  • carboxylic acid ligands eg, acetic acid ligand, etc.
  • alcoholato ligands eg, phenolato ligands etc.
  • carbon monoxide ligands isonitrile nitrile ligands, cyano ligands, and more preferably nitrogen-containing heterocyclic ligands.
  • the metal complex may have one transition metal atom in the compound, or may be a so-called dinucle
  • Fluorescent light-emitting dopants generally include benzoxazole, benzoimidazole, benzothiazole, styryl benzene, polyphenyl, diphenyl butadiene, tetraphenyl butadiene, naphthalimide, coumarin, pyran, perinone, oxa Diazole, aldazine, pyraridine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, aromatic dimethyridin compounds, fused polycyclic aromatic compounds (anthracene, phenanthroline, pyrene, perylene, Rubrene or pentacene etc.), metal complexes of 8-quinolinol, various metal complexes represented by pyrromethene complexes and rare earth complex
  • the hole-transporting host material used in the light-emitting layer of the present invention has an ionization potential Ip of 5.1 eV or more and 6.4 eV or less from the viewpoint of improving the durability and decreasing the driving voltage. Is more preferably 5.4 eV or more and 6.2 eV or less, and still more preferably 5.6 eV or more and 6.0 eV or less.
  • the electron affinity Ea is preferably 1.2 eV or more and 3.1 eV or less, more preferably 1.4 eV or more and 3.0 eV or less, and 1.8 eV or more More preferably, it is 2.8 eV or less.
  • the lowest triplet excitation level (hereinafter referred to as T1) is preferably 2.2 eV or more and 3.7 eV or less, more preferably 2.4 eV or more and 3.7 eV or less, and most preferably 2.4 eV or more. It is 4 eV or less.
  • a hole transportable host material the following materials can be mentioned, for example. Pyrrole, indole, carbazole, azaindole, azacarbazole, pyrazole, imidazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary Amine compounds, styrylamine compounds, aromatic dimethyridin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophenes, organosilanes, Carbon films, derivatives thereof and the like can be mentioned.
  • indole derivatives carbazole derivatives, azaindole derivatives, azacarbazole derivatives, aromatic tertiary amine compounds, and thiophene derivatives are preferable, and an indole skeleton, a carbazole skeleton, an azaindole skeleton, an azacarbazole skeleton, or an aromatic Those having a plurality of tertiary amine skeletons are more preferable.
  • Particularly preferred hole transporting host materials in the present invention are carbazole derivatives.
  • a host material in which part or all of hydrogen of the host material is replaced with deuterium can be used (see, for example, Japanese Patent Application No. 2008-126130 application specification, Japanese Patent Application Publication No. 2004-515506). Specific examples of such a hole transporting host material include, but are not limited to, the following.
  • the electron-transporting host material used in the present invention preferably has an electron affinity Ea of 2.5 eV or more and 3.5 eV or less from the viewpoint of improving the durability and lowering the driving voltage. It is more preferably 2.6 eV or more and 3.4 eV or less, and still more preferably 2.8 eV or more and 3.3 eV or less. Further, from the viewpoint of improving the durability and lowering the driving voltage, the ionization potential Ip is preferably 5.7 eV or more and 7.5 eV or less, more preferably 5.8 eV or more and 7.0 eV or less, and 5.9 eV or more More preferably, it is 6.5 eV or less.
  • the lowest triplet excitation level (hereinafter referred to as T1) is preferably 2.2 eV or more and 3.7 eV or less, more preferably 2.4 eV or more and 3.7 eV or less, and most preferably 2.4 eV or more. It is 4 eV or less.
  • Such an electron transporting host include pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandione.
  • the electron transporting host is preferably a metal complex, an azole derivative (benzimidazole derivative, imidazopyridine derivative, etc.), an azine derivative (pyridine derivative, pyrimidine derivative, triazine derivative, etc.), and among them, in the present invention
  • metal complex compounds are preferred.
  • the metal complex compound is more preferably a metal complex having a ligand having at least one nitrogen atom or oxygen atom or sulfur atom coordinated to a metal.
  • the metal ion in the metal complex is not particularly limited, but is preferably beryllium ion, magnesium ion, aluminum ion, gallium ion, zinc ion, indium ion, tin ion, platinum ion or palladium ion, more preferably beryllium ion, It is an aluminum ion, a gallium ion, a zinc ion, a platinum ion or a palladium ion, more preferably an aluminum ion, a zinc ion, a platinum ion or a palladium ion.
  • Examples of the ligand contained in the metal complex include various known ligands. For example, “Photochemistry and Photophysics of Coordination Compounds”, Springer-Verlag, H. Ligands described in Yersin, 1987, “Organometallic Chemistry-Basics and Applications-”, Shokabo, Akio Yamamoto, 1982, etc. may be mentioned.
  • the ligand is preferably a nitrogen-containing heterocyclic ligand (preferably having a carbon number of 1 to 30, more preferably a carbon number of 2 to 20, particularly preferably a carbon number of 3 to 15, and is a monodentate ligand).
  • the ligand may be a bidentate or more ligand, preferably a bidentate or more and a bidentate ligand or a mixed ligand of a bidentate or more than 6 or less and a monodentate ligand. preferable.
  • the ligand examples include, for example, azine ligand (for example, pyridine ligand, bipyridyl ligand, terpyridine ligand, etc.), hydroxyphenylazole ligand (for example, hydroxyphenyl benzimidazole coordination) And a hydroxyphenylbenzoxazole ligand, a hydroxyphenylimidazole ligand, and a hydroxyphenylimidazopyridine ligand, etc.), an alkoxy ligand (preferably having a carbon number of 1 to 30, more preferably a carbon number).
  • azine ligand for example, pyridine ligand, bipyridyl ligand, terpyridine ligand, etc.
  • hydroxyphenylazole ligand for example, hydroxyphenyl benzimidazole coordination
  • alkoxy ligand preferably having a carbon number of 1 to 30, more preferably a carbon number
  • the number of carbon atoms is preferably 1 to 20, particularly preferably 1 to 10, and examples thereof include methoxy, ethoxy, butoxy and 2-ethylhexyloxy), and aryloxy ligands (preferably 6 to 30 carbon atoms, more preferably) Is 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms.
  • the heteroaryloxy ligand (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, particularly preferably a carbon number of 1 to 12, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like. ),
  • An alkylthio ligand (preferably having a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and particularly preferably a carbon number of 1 to 12, and examples include methylthio, ethylthio and the like), and arylthio ligands.
  • carbon atoms Preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples include phenylthio and the like), heteroarylthio ligands (preferably 1 carbon atom) -30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, And 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like), siloxy ligands (preferably having 1 to 30 carbon atoms, more preferably 3 to 25 carbon atoms).
  • aromatic hydrocarbon anion ligands preferably having 6 carbon atoms.
  • aromatic hydrocarbon anion ligands preferably having 6 carbon atoms.
  • -30 more preferably 6 to 25 carbon atoms, particularly preferably 6 to 20 carbon atoms, and examples thereof include phenyl anion, naphthyl anion and anthranyl anion etc., aromatic heterocyclic anion ligand (preferably) Is preferably 1 to 30 carbon atoms, more preferably 2 to 25 carbon atoms, and particularly preferably 2 to 20 carbon atoms.
  • pyrrole anions pyrazole anions, pyrazole anions, triazole anions, oxazole anions, benzoxazole anions, thiazole anions, benzothiazole anions, thiophene anions, benzothiophene anions, etc.
  • indolenine anion ligands etc.
  • a nitrogen-containing heterocyclic ligand, an aryloxy ligand, a heteroaryloxy group or a siloxy ligand more preferably a nitrogen-containing heterocyclic ligand, an aryloxy ligand, a siloxy coordination And aromatic hydrocarbon anion ligands or aromatic heterocyclic anion ligands.
  • Examples of the metal complex electron transporting host material are disclosed in, for example, JP-A-2002-235076, JP-A-2004-214179, JP-A-2004-221062, JP-A-2004-221065, JP-A-2004-221068, JP-A-2004-327313, etc.
  • the compounds described can be mentioned.
  • an electron transportable host material although the following materials can be mentioned, for example, it is not limited to these.
  • the weight ratio of the light emitting material to the host material is 50:50 to 0.1: 99.9, preferably 40:60 to 1:99, more preferably 30:70. To 3:97.
  • the light emitting layer of the present invention is disclosed in Japanese Patent Application Nos. 2007-196525, 2007-196527, 2007-196674, 2007-196675, and 2007-196676 for the purpose of improving luminous efficiency and improving durability.
  • the concentration of the luminescent material can be varied sequentially or stepwise in the manner described.
  • the light emitting layer may be two or more layers, one of which may contain the compound represented by the general formula (1) or the general formula (2), and a plurality of layers or all of them.
  • the layer may contain the compound represented by the general formula (1) or the general formula (2).
  • the electron transport layer is a layer having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
  • a material which can be used for the electron injection layer of this invention and an electron carrying layer, and it may be a low molecular weight compound or a high molecular weight compound.
  • the electron transport layer in the present invention is at least a first electron transport layer provided in contact with the cathode side interface of the light emitting layer, and a second electron provided in contact with the cathode side interface of the first electron transport layer.
  • the second electron-transporting layer is represented by the following general formula (ET), an alkali metal, an alkali metal salt, an alkaline earth metal and an alkaline earth metal salt And at least one selected from the group consisting of
  • R 1 represents a hydrogen atom or a substituent
  • n represents an integer of 0 to 8.
  • n is an integer of 2 or more
  • plural R 1 s may be the same as or different from each other.
  • the material that can be used for the first electron-transporting layer of the present invention is not particularly limited, and may be a low molecular weight compound or a high molecular weight compound. Specifically, pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone Derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic tetracarboxylic acid anhydrides such as naphthalene and perylene, phthalocyanine derivatives, metal complex
  • the first electron transport layer in the present invention may or may not contain an electron donating dopant.
  • the first electron transport layer in the present invention does not contain an electron donating dopant.
  • the electron donating dopant introduced into the first electron transporting layer may have an electron donating property and a property to reduce an organic compound, and an alkali metal such as Li, Mg And alkaline earth metals, transition metals including rare earth metals, reducing organic compounds, and the like are preferably used.
  • an alkali metal such as Li, Mg And alkaline earth metals, transition metals including rare earth metals, reducing organic compounds, and the like are preferably used.
  • the metal metals having a work function of 4.2 eV or less can be particularly preferably used.
  • a nitrogen-containing compound, a sulfur-containing compound, a phosphorus-containing compound etc. are mentioned, for example.
  • materials described in JP-A-6-212153, JP-A-2000-196140, JP-A-2003-68468, JP-A-2003-229278, JP-A-2004-342614, etc. can be used.
  • electron donating dopants may be used alone or in combination of two or more.
  • the amount of electron donating dopant used varies depending on the type of material, but is preferably 0.1% by mass to 30% by mass, and more preferably 0.1% by mass to 20% by mass, with respect to the material of the electron transport layer Is more preferably 0.1% by mass to 10% by mass.
  • the thickness of the first electron transporting layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm, from the viewpoint of lowering the driving voltage.
  • the second electron-transporting layer in the present invention comprises at least an electron-transporting material represented by the above general formula (ET), an alkali metal, an alkali metal salt, an alkaline earth metal and an alkaline earth It contains at least one selected from the group consisting of metal salts.
  • the mixing ratio of the total of the alkali metal, the alkaline earth metal or the salts thereof to the electron transporting material represented by the general formula (ET) in the second electron transporting layer is 0.1% by mass to 5.0% by mass
  • the content is preferably 0.1% by mass to 2.0% by mass, and more preferably 0.1% by mass to 1.0% by mass.
  • the thickness of the second electron transport layer is preferably 1 nm to 100 nm, more preferably 2 nm to 30 nm, and still more preferably 5 nm to 20 nm, from the viewpoint of lowering the driving voltage.
  • the ratio of the thickness of the first electron transport layer to the thickness of the second electron transport layer is determined by voltage increase, alkali metal, alkaline earth metal or their salts. From the viewpoint of preventing diffusion, 0.1 to 3 is preferable, 0.1 to 2 is more preferable, and 0.2 to 0.5 is more preferable.
  • R 1 represents a hydrogen atom or a substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms
  • n represents an integer of 0 to 8.
  • n is an integer of 2 or more, plural R 1 s may be the same as or different from each other.
  • alkyl group having 1 to 10 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, 2-butyl group, tert-butyl group, n-pentyl group and 2-pentyl group , 3-pentyl group, neopentyl group, n-hexyl group, 2-hexyl group, 2-ethylhexyl group, 2-butylhexyl group, n-heptyl group, n-octyl group, 2-octyl group, n-nonyl group, And n-decyl group.
  • Examples of the substituted or unsubstituted aryl group having 6 to 30 carbon atoms include phenyl group, 1-naphthyl group, 2-naphthyl group, 4-phenyl-1-naphthyl group, 1-anthryl group, 2-anthryl group, 9 -Anthryl group, 10-phenyl-9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-pyrenyl group, 2-pyrenyl group, 2- Perylenyl group, 3-perylenyl group, 1-fluoranthenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 2-triphenylenyl group, 9,9-dimethylfluoren-2-yl group, 9,9-dibutyl Fluoren-2-yl group, 9,9-dihexyl fluor
  • the substituent in the case of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms is an alkyl group, preferably an alkyl group having 1 to 10 carbon atoms, and specifically, a methyl group, an ethyl group, n -Propyl group, isopropyl group, n-butyl group, 2-butyl group, tert-butyl group, n-pentyl group, 2-pentyl group, 3-pentyl group, neopentyl group, n-hexyl group, 2-hexyl group, Examples thereof include 2-ethylhexyl group, 2-butylhexyl group, n-heptyl group, n-octyl group, 2-octyl group, n-nonyl group, and n-decyl group.
  • Alkali metal used in the present invention as the alkali metal salts, alkaline earth metal and alkaline earth metal salts, Li, Cs, Ca, LiF , NaF, KF, RbF, CsF, MgF 2, CaF 2, SrF 2, BaF 2, LiCl, NaCl, KCl, RbCl, CsCl, MgCl 2, CaCl 2, SrCl 2, BaCl 2, LiHCO 3, NaHCO 3, KHCO 3, RbHCO 3, CsHCO 3, Li 2 CO 3, Na 2 CO 3, K 2 CO 3 , Rb 2 CO 3 , Cs 2 CO 3 , MgCO 3 , CaCO 3 , SrCO 3 , BaCO 3 and the like.
  • it is Li or Cs.
  • the hole injection layer, the hole transport layer is a layer having a function of receiving holes from the anode or the anode side and transporting the holes to the cathode side.
  • the material that can be used for the hole injection layer and the hole transport layer of the present invention and a low molecular weight compound, a high molecular weight compound, or an inorganic material may be used.
  • pyrrole derivatives carbazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives , Silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethyridin compounds, phthalocyanine compounds, porphyrin compounds, thiophene derivatives, organic silane derivatives, carbon, phenyl azole, phenyl azine as ligands It is preferable that it is a layer containing a metal complex and the like.
  • hole injection and transport materials include, but are not limited to, those of H-1 to 25.
  • the inorganic material include silicon oxide, silicon dioxide, germanium oxide, germanium dioxide, germanium oxide, vanadium pentoxide, molybdenum trioxide, aluminum oxide, iron dioxide, iron trioxide and the like.
  • the hole injecting layer or the hole transporting layer of the organic EL device of the present invention can contain an electron accepting dopant.
  • an electron accepting dopant in the hole injection layer.
  • an inorganic compound or an organic compound can be used as long as it has an electron accepting property and a property of oxidizing an organic compound.
  • examples of the inorganic compound include ferric chloride, metal chlorides such as aluminum chloride, gallium chloride, indium chloride, antimony pentachloride and the like, vanadium pentoxide, and metal oxides such as molybdenum trioxide.
  • a compound having a nitro group, a halogen, a cyano group, a trifluoromethyl group or the like as a substituent a quinone compound, an acid anhydride compound, a fullerene or the like can be suitably used.
  • organic electron donors specifically, hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane, tetrafluorotetracyanoquinodimethane, p-fluoranil, p-chloranil, p-bromonil, p-benzoquinone 2,6-dichlorobenzoquinone, 2,5-dichlorobenzoquinone, tetramethylbenzoquinone, 1,2,4,5-tetracyanobenzene, o-dicyanobenzene, p-dicyanobenzene, 1,4-dicyanotetrafluorobenzene, 2,3-Dichloro-5,6-dicyanobenzoquinone, p-dinitrobenzene, m-dinitrobenzene, o-dinitrobenzene, p-cyanonitrobenzene, m-cyanonitrobenzene, o-
  • organic electron donors may be used alone or in combination of two or more.
  • Publication No. 2001-102175 Publication No. 2001-160493 Publication No. 2002-252085 Publication No. 2002-56985 Publication No. 2003-157981 Publication No. 2003-217862 Preferably, the compounds described in JP-A-2003-229278, JP-A-2004-342614, JP-A-2005-72012, JP-A-2005-166637, JP-A-2005-209643, etc. are preferably used. Can do.
  • electron accepting dopants may be used alone or in combination of two or more.
  • the amount of the electron accepting dopant used varies depending on the type of material, but is preferably 0.01% by mass to 50% by mass, more preferably 0.05% by mass to 20% by mass, with respect to the hole transport layer material More preferably, it is 0.1% by mass to 10% by mass.
  • the thickness of each of the hole injection layer and the hole transport layer is preferably 500 nm or less from the viewpoint of lowering the driving voltage.
  • the thickness of the hole transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 300 nm, and still more preferably 10 nm to 200 nm.
  • the thickness of the hole injection layer is preferably 0.1 nm to 500 nm, more preferably 0.5 nm to 300 nm, and still more preferably 1 nm to 200 nm.
  • the hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the above-mentioned materials, or may have a multilayer structure composed of a plurality of layers of the same composition or different compositions. .
  • an electrically inactive hydrocarbon compound such as an adamantane compound can be added to the hole transport layer by the method disclosed in JP-A-2005-294249 or the like for the purpose of improving the luminous efficiency.
  • the hole injection layer and T1 of the hole transport layer are not particularly limited, but for the purpose of suppressing exciton diffusion, the difference between T1 of the hole transport layer adjacent to the light emitting layer and T1 of the light emitting layer is within 1 eV Is preferred.
  • the organic compound layer in the present invention has, from the anode side, a light emitting layer, a first electron transporting layer, and a second electron transporting layer, and preferably a hole transporting layer, a light emitting layer, a first electron transporting layer, and The aspect laminated
  • a charge blocking layer (electron blocking layer, hole blocking layer) or the like may be provided between the hole transporting layer and the light emitting layer, or between the light emitting layer and the electron transporting layer.
  • a hole injection layer may be provided between the anode and the hole transport layer
  • an electron injection layer may be provided between the cathode and the electron transport layer.
  • Each layer may be divided into a plurality of secondary layers.
  • the step layer can be effectively provided by the method disclosed in Japanese Patent Application Laid-Open Nos. 2006-279014 and 2006-351680 for the purpose of injecting charges more effectively into the light emitting layer.
  • the step layer is composed of a plurality of layers including the hole transport layer adjacent to the light emitting layer, and the ionization potential of the light emitting layer is Ip1, and the ionization potential of the hole transport layer adjacent to the light emitting layer is Ip2.
  • the electron transport layer comprises a plurality of layers including a layer adjacent to the light emitting layer, satisfying the relationship of Ip1>Ip2> Ip3, and the electron affinity of the light emitting layer
  • the organic electroluminescent element satisfies the relationship of Ea1 ⁇ Ea2 ⁇ Ea3 where Ea1 is an electron affinity of the electron transport layer adjacent to the light emitting layer Ea2 and electron affinities of the other electron transport layers are Ea3.
  • the step layer can be thinned by the method disclosed in JP-A-2006-351715, and charge can be injected more effectively.
  • a thin film organic layer may be provided between the cathode and the electron transport layer by the method disclosed in JP 2007-227888 A for the purpose of injecting electrons effectively from the cathode to the electron transport layer to lower the voltage. it can.
  • the charge generation layer is provided by a method disclosed in Japanese Patent Application Laid-Open Nos. 2003-272860, 11-329748, etc. to make a multi-photon type device. You can also.
  • an organic compound layer including a light emitting layer is provided between the reflective plate (or the reflective electrode) and the semitransparent electrode for the purpose of further improving the luminous efficiency, the durability and the chromaticity.
  • the substrate from which the light emitted from the light emitting layer is taken out is preferably a substrate that does not scatter or attenuate.
  • a substrate that does not scatter or attenuate include zirconia-stabilized yttrium (YSZ), inorganic materials such as glass, polyethylene terephthalate, polybutylene phthalate, polyesters such as polyethylene naphthalate, polystyrene, polycarbonate, polyether sulfone, polyarylate, polyimide, polycycloolefin And norbornene resins and organic materials such as poly (chlorotrifluoroethylene).
  • YSZ zirconia-stabilized yttrium
  • inorganic materials such as glass, polyethylene terephthalate, polybutylene phthalate, polyesters such as polyethylene naphthalate, polystyrene, polycarbonate, polyether sulfone, polyarylate, polyimide, polycycloolefin And norbornene
  • an alkali-free glass as its material in order to reduce ions eluted from the glass.
  • soda lime glass it is preferable to use what provided barrier coatings, such as a silica.
  • barrier coatings such as a silica.
  • an organic material it is preferable to be excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation and processability.
  • the shape of the substrate is preferably a plate.
  • the structure of the substrate may be a single-layer structure, a laminated structure, a single member, or two or more members.
  • a moisture permeation preventive layer can be provided on the front surface or the back surface of the substrate.
  • materials for the moisture permeation preventive layer (gas barrier layer) inorganic substances such as silicon nitride and silicon oxide are suitably used.
  • the moisture permeation preventing layer (gas barrier layer) can be formed, for example, by a high frequency sputtering method.
  • a hard coat layer, an undercoat layer or the like may be provided.
  • the substrate may be washed and / or pretreated before and / or after preparation of the electrode, or before forming the organic compound layer.
  • the washing can be carried out with any of water, pure water, ion-exchanged water, acid, alkaline water and organic solvents, and may be immersed and ultrasonic cleaning.
  • pretreatment may be performed for the purpose of decomposing and removing an organic substance, for the purpose of improving adhesiveness, and for the purpose of promoting charge injection from an electrode to an organic compound layer.
  • UV-ozone treatment, oxygen plasma treatment and the like are preferably used, but it is not particularly limited.
  • the anode generally has only to have a function as an electrode for supplying holes to the organic compound layer, and there is no particular limitation on the shape, structure, size, etc., depending on the application and purpose of the light emitting device. And can be appropriately selected from known electrode materials.
  • the anode may be provided as a transparent anode on the side from which light is extracted, and may or may not be transparent on the side opposite to the side from which light is extracted.
  • anode As a material of an anode, a metal, an alloy, a metal oxide, a conductive compound, or these mixtures are mentioned suitably, for example.
  • the anode material include conductive metals such as tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), zinc indium oxide (IZO), etc.
  • Metals such as oxides, gold, silver, chromium and nickel, mixtures or laminates of these metals and conductive metal oxides, inorganic conductive substances such as copper iodide and copper sulfide, polyaniline, polythiophene, polypyrrole, etc.
  • ITO organic conductive materials, and laminates of these with ITO.
  • conductive metal oxides are preferred.
  • ITO is preferable in terms of productivity, high conductivity, transparency and the like, but it may be laminated with other materials, and an auxiliary electrode etc. May be provided
  • the anode may be, for example, a printing method, a wet method such as a coating method, a vacuum evaporation method, a physical method such as a sputtering method or an ion plating method, or a chemical method such as CVD or plasma CVD. It can be formed on the substrate according to a method appropriately selected in consideration of the compatibility with the material to be processed. For example, when ITO is selected as the material of the anode, the anode can be formed according to a direct current or high frequency sputtering method, a vacuum evaporation method, an ion plating method or the like.
  • the work function of the anode is not limited as long as holes can be injected into the hole injection layer or the hole transport layer adjacent to the anode, and 4.0 eV or more and 6.0 eV or less is preferable, and 4.5 eV More than 5.8 eV is more preferable.
  • the work function of the anode can be adjusted to an arbitrary value by UV ozone treatment or oxygen plasma treatment.
  • the position at which the anode is formed is not particularly limited and may be appropriately selected depending on the application and purpose of the light emitting device, but is preferably formed on the substrate.
  • the anode may be formed on the whole of one surface of the substrate, or may be formed on a part thereof.
  • the patterning when forming the anode may be performed by chemical etching such as photolithography, or may be performed by physical etching such as laser, or a mask may be overlaid to perform vacuum deposition or sputtering. It may be carried out by the lift-off method or the printing method.
  • the thickness of the anode can be appropriately selected depending on the material constituting the anode, and can not be generally defined, but is usually about 10 nm to 50 ⁇ m, preferably 50 nm to 20 ⁇ m.
  • the resistance value of the anode is preferably 10 3 ⁇ / sq or less, more preferably 10 2 ⁇ / sq or less.
  • the anode When the anode is transparent, it may be colorless and transparent or colored and transparent.
  • permeability in order to take out light emission from the transparent anode side, 60% or more is preferable and 70% or more is more preferable.
  • the transparent anode is described in detail in "New Development of Transparent Electrode Film” supervised by Yutaka Sawada (CMC) (1999), and the matters described here can be applied to the present invention.
  • ITO or IZO is used, and a transparent anode formed at a low temperature of 150 ° C. or less is preferable.
  • the cathode only needs to have a function as an electrode for injecting electrons into the organic compound layer, and there is no particular limitation on the shape, structure, size, etc., depending on the application and purpose of the light emitting device. It can be appropriately selected from known electrode materials. In the case where the cathode side is a side from which light is taken out, it is preferable that the cathode side is transparent or translucent.
  • a material which comprises a cathode a metal, an alloy, a metal oxide, electroconductive compounds, these mixtures etc. are mentioned, for example.
  • Specific examples include alkali metals (eg, LI, Na, K, Cs etc.), alkaline earth metals (eg Mg, Ca etc.), gold, silver, lead, aluminum, sodium-potassium alloy, lithium-aluminum alloy, magnesium Silver alloys, indium and rare earth metals such as ytterbium etc.
  • alkali metals eg, LI, Na, K, Cs etc.
  • alkaline earth metals eg Mg, Ca etc.
  • ytterbium rare earth metals
  • the work function of the cathode is not particularly limited as long as the work function can inject electrons into the adjacent organic compound layer, and is preferably 2.5 eV or more and 4.5 eV or less, more preferably 2.5 eV or more and 4.3 eV or less It is.
  • alkali metals and alkaline earth metals are preferable as the material constituting the cathode from the point of electron injection, and materials mainly composed of aluminum are preferable from the viewpoint of excellent storage stability, but conductive materials such as ITO and the like are preferable. And a layered structure with the metal oxide.
  • the material mainly composed of aluminum means aluminum alone, an alloy of aluminum and 0.01% to 10% by weight of alkali metal or alkaline earth metal, or a mixture thereof (eg, lithium-aluminum alloy, magnesium-aluminum alloy) Etc).
  • the cathode described above is configured from a printing method, a wet method such as a coating method, a physical method such as a vacuum evaporation method, a sputtering method, an ion plating method, or a chemical method such as CVD or plasma CVD. It can be formed according to a method appropriately selected in consideration of the compatibility with the material. For example, when a metal or the like is selected as the material of the cathode, one or more of them can be simultaneously or sequentially sputtered or the like.
  • the patterning when forming the cathode may be performed by chemical etching such as photolithography, or may be performed by physical etching using a laser or the like, or may be performed by vacuum deposition or sputtering by overlapping a mask. It may be done by the lift-off method or the printing method.
  • the position at which the cathode is formed is not particularly limited, and may be formed on the whole of the organic compound layer, or may be formed on a part thereof.
  • a dielectric layer of an alkali metal or alkaline earth metal fluoride, oxide or the like may be inserted between the cathode and the organic compound layer with a thickness of 0.1 nm to 5 nm.
  • This dielectric layer can also be viewed as a type of electron injection layer.
  • the dielectric layer can be formed by, for example, a vacuum evaporation method, a sputtering method, an ion plating method or the like.
  • the thickness of the cathode can be appropriately selected depending on the material constituting the cathode, and can not be generally defined, but is usually about 5 nm to 5 ⁇ m, preferably 10 nm to 1 ⁇ m.
  • the cathode may be transparent or opaque.
  • the transparent cathode can be formed by forming a thin film of a material of the cathode to a thickness of 1 nm to 10 nm and further laminating a transparent conductive material such as ITO or IZO.
  • ITO or IZO transparent conductive material
  • the anode side can be made transparent, and the cathode side can be made opaque (reflection electrode) to make a bottom emission type element.
  • both the anode and the cathode can be transparent to make both-side light emission type.
  • the organic compound layer in the present invention includes, as the organic compound layer other than the light emitting layer and the electron transporting layer, layers such as a hole transporting layer, a charge blocking layer, a hole injecting layer and an electron injecting layer.
  • each layer constituting the organic compound layer is suitably formed by any of dry film forming method such as vapor deposition method and sputtering method, wet coating method, transfer method, printing method, ink jet method and the like. be able to.
  • the dry film forming method is mainly an evaporation method.
  • the deposition rate by deposition of the organic compound layer is preferably 0.1 angstrom / second to 100 angstrom / second, more preferably 0.1 angstrom / second to 50 angstrom / second.
  • the heating temperature is not limited as long as the material is not decomposed.
  • the degree of vacuum at the time of vapor deposition film formation is preferably 10 ⁇ 2 Pa to 10 ⁇ 9 Pa, and more preferably 10 ⁇ 3 Pa to 10 ⁇ 8 Pa.
  • the vacuum atmosphere at the time of vapor deposition film formation may be either an air vacuum atmosphere or an inert gas vacuum atmosphere such as nitrogen or argon.
  • baking treatment can be performed, or a getter agent or the like can be heated to remove moisture and oxygen in the deposition tank.
  • a getter agent or the like can be heated to remove moisture and oxygen in the deposition tank.
  • moisture adhering to the substrate can be removed or the film quality of the organic film can be controlled.
  • the host material and the light emitting material can be separately deposited in separate evaporation sources for co-evaporation, or they can be vapor deposited by mixing in one evaporation source.
  • thermoball or the like can be provided to the deposition source. Moreover, it can also be heat-treated after film formation.
  • the temperature for heat treatment is not particularly limited, and may be set arbitrarily, even if it is higher than or equal to the glass transition point of the material to be configured.
  • heat treatment can also be performed.
  • the temperature for heat treatment is not particularly limited, and may be set arbitrarily, even if it is higher than or equal to the glass transition point of the material to be configured.
  • the entire organic EL element may be protected by a protective layer.
  • the material contained in the protective layer may be any material having a function to prevent substances such as moisture and oxygen that accelerate element deterioration from entering the element. Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, Ni, MgO, SiO, SiO 2 , Al 2 O 3 , GeO, NiO, CaO, BaO, Fe 2 O 3 , metal oxides such as Y 2 O 3 , TiO 2 , metal nitrides such as SiN x , SiN x O y , metal fluorides such as MgF 2 , LiF, AlF 3 , CaF 2 , polyethylene, polypropylene, polymethyl Methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymer of chlorotrifluor
  • the method for forming the protective layer is not particularly limited.
  • vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency radiation) Excitation ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, transfer method can be applied.
  • the entire device may be sealed using a sealing container. It can also be sealed with an inorganic film such as SiN or SiON. Furthermore, solid sealing can be performed by the method disclosed in JP-A-2005-294249 and the like. In addition, a water absorbent or an inert liquid may be enclosed in the space between the sealed container and the light emitting element.
  • the water absorbent is not particularly limited, and, for example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride And cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieves, zeolites, and magnesium oxide.
  • the inert liquid is not particularly limited. For example, paraffins, liquid paraffins, perfluoroalkanes, perfluoroamines, fluorinated solvents such as perfluoroethers, chlorinated solvents, and silicone oils It can be mentioned.
  • the organic electroluminescent device of the present invention emits light by applying a direct current (which may optionally include an alternating current component) voltage (usually 2 to 15 volts) or direct current between the anode and the cathode. You can get it.
  • a direct current which may optionally include an alternating current component
  • alternating current component usually 2 to 15 volts
  • the method of driving the organic electroluminescent device of the present invention those disclosed in JP-A Nos. 2-148687, 6-301355, 5-29080, 7-134558, 8-234685 and 8-241047 can be used.
  • the driving methods described in each publication, Patent No. 2784615, and US Patent Nos. 5828429 and 6023308 can be applied.
  • the device of the present invention can be heat-treated by the method disclosed in Japanese Patent Application No. 2008-48630 etc.
  • the TFT can use either amorphous silicon, low temperature polysilicon, or an oxide semiconductor.
  • the light emitting element of the present invention can improve the light extraction efficiency by various known devices. For example, processing the substrate surface shape (for example, forming a fine concavo-convex pattern), controlling the refractive index of the substrate, ITO layer, organic compound layer, controlling the film thickness of the substrate, ITO layer, organic compound layer, etc.
  • processing the substrate surface shape for example, forming a fine concavo-convex pattern
  • controlling the refractive index of the substrate, ITO layer, organic compound layer controlling the film thickness of the substrate, ITO layer, organic compound layer, etc.
  • the chromaticity can be further improved by installing a color filter or using a color conversion material.
  • other color light emitting materials can be added to the device of the present invention to reproduce other colors including white.
  • the light emitting layer may be a single layer light emitting layer or a plurality of light emitting layers, or may be a multi-photon type device.
  • the device of the present invention can also be combined with other pixels in the panel to achieve many color reproductions. In that case, three color sub-pixels of red, green, and blue may be combined, and which color to combine may be determined according to the purpose.
  • the panel can be driven either by active drive or passive drive. Also, both current drive and voltage drive can be taken.
  • the organic electroluminescent device of the present invention can be suitably used for display devices, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signs, interiors, optical communication and the like.
  • Example 1 Production of Organic EL Element 1 of the Present Invention
  • a transparent support substrate was prepared by depositing indium tin oxide (hereinafter abbreviated as ITO) to a thickness of 100 nm and forming a film on a 25 mm ⁇ 25 mm ⁇ 0.7 mm glass substrate (manufactured by Tokyo Sanyo Vacuum Co., Ltd.) .
  • the transparent support substrate was etched and washed. On this, the following organic compound layers were sequentially provided by vacuum evaporation at a deposition rate of 1 ⁇ / sec.
  • Hole injection layer 4,4 ′, 4 ′ ′-tris (2-naphthylphenylamino) triphenylamine (abbreviated as 2-TNATA) and 2,3,5,6-tetrafluoro-7,7,8, 8-Tetracyanoquinodimethane (abbreviated as F4-TCNQ) was co-evaporated such that F4-TCNQ was 1.0% by mass with respect to 2-TNATA, and the thickness was 120 nm.
  • Hole transport layer The hole transport material was N, N′-dinaphthyl-N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviated as ⁇ -NPD). The thickness was 10 nm.
  • Electron block layer The following compound a was vapor-deposited to a thickness of 3 nm.
  • Light emitting layer 1,3-bis (N-carbazol-9-yl) benzene (abbreviated as mCP) as a host material, a platinum complex Pt-1 as a light emitting material, and a mass ratio of mCP to Pt-1 of 85:15 Co-evaporated to be The thickness was 30 nm.
  • First electron transporting layer Aluminum (III) bis (2-methyl-8-quinolato) -4-phenylphenolate (abbreviated as BAlq) was deposited to a thickness of 10 nm.
  • Second electron-transporting layer Baxocuproin (abbreviated as BCP) and Li shown below as a compound represented by the general formula (ET), and the doping amount of Li relative to BCP is 0.4% by mass As co-evaporated. The thickness was 20 nm.
  • LiF was vapor deposited to a thickness of 1 nm as an electron injection layer, and then patterned with a shadow mask to provide Al having a thickness of 100 nm as a cathode by a vacuum vapor deposition method.
  • the produced laminate was placed in a nitrogen gas-substituted glove box, and sealed with a glass sealing can and an ultraviolet curing adhesive (XNR5516HV, manufactured by Nagase Ciba).
  • Element 2 of the present invention In the same manner as the device 1 of the present invention, except that mCP in the light emitting layer is changed to the following hole transportable host material A, and the others have the same composition as the device 1 of the present invention. did.
  • Element 3, 5 and 6 of the present invention In the same manner as in the device 1 of the present invention, except that the Li doping amount to BCP in the second electron transport layer is changed, the others have the same composition as the device 1 of the present invention. 6 was produced.
  • the element 3 of the present invention the doping amount of Li is 0.1% by mass.
  • Element 5 of the present invention Li doping amount is 0.6% by mass.
  • the element of the present invention 6 the doping amount of Li is 1% by mass.
  • Elements 7 to 10 of the present invention In the same manner as in the element 1 of the present invention, except that BCP is used as a compound represented by the general formula (ET) in the second electron transport layer and the following bathophenanthroline is used, and the Li doping amount to bathophenanthroline is changed
  • the elements 7 to 10 of the present invention were manufactured using the same composition as that of the element 1 of the present invention except for the above.
  • the element 7 of the present invention the doping amount of Li is 0.1% by mass.
  • the element 8 of the present invention the doped amount of Li is 0.4% by mass.
  • the element 9 of the present invention the Li doping amount is 0.6% by mass.
  • the element 10 of the present invention the doping amount of Li is 1% by mass.
  • Elements 11 to 14 of the present invention In the same manner as in the device 1 of the present invention, except that BCP in the second electron transport layer is doped with Cs and the doping amount of Cs in BCP is changed, and the other components are the same as the device 1 of the present invention.
  • the elements 11 to 14 of the present invention were produced.
  • the element 11 of the present invention the doping amount of Cs is 0.1% by mass.
  • the element 12 of the present invention the doping amount of Cs is 0.4% by mass.
  • the element 13 of the present invention the doping amount of Cs 0.6 mass%.
  • the element 14 of the present invention the doping amount of Cs is 1% by mass.
  • Elements 15 to 18 of the present invention In the same manner as in the element 2 of the present invention, except that BCP in the second electron transport layer is doped with Cs and the doping amount of Cs in BCP is changed, the other components are the same as the element 2 of the present invention
  • the elements 15 to 18 of the present invention were produced.
  • the element 15 of the present invention the doping amount of Cs is 0.1% by mass.
  • the element 16 of the present invention the doping amount of Cs is 0.4% by mass.
  • the element 17 of the present invention the doping amount of Cs is 0.6% by mass.
  • the element 18 of the present invention the doping amount of Cs is 1% by mass.
  • Element 19 of the present invention In the same manner as in the element 1 of the present invention, except that 0.4 mass% of Cs 2 CO 3 is doped to BCP in the second electron transport layer, and the other composition is the same as the element 1 of the present invention.
  • the element 19 was manufactured.
  • Device 20 of the present invention A device 20 of the present invention is prepared in the same manner as the device 1 of the present invention except that 0.4 mass% of Ca is doped to BCP in the second electron transport layer, and the other components have the same composition as the device 1 of the present invention. Was produced.
  • Element 21 of the present invention A device of the present invention is prepared in the same manner as the device 1 of the present invention except that 0.4 wt% of CaF 2 is doped to BCP in the second electron transport layer, and the others have the same composition as the device 1 of the present invention. 21 was produced.
  • Element 22 of the present invention was prepared in the same manner as the preparation of the element 1 of the present invention, except that Pt-1 was replaced with the exemplified compound 26 in the preparation of the element 1 of the present invention.
  • the obtained device was evaluated in the same manner as the device 1 of the present invention.
  • Element 23 of the present invention was prepared in the same manner as the preparation of the element 1 of the present invention, except that Pt-1 was replaced with exemplified compound 29 in the preparation of the element 1 of the present invention.
  • the obtained device was evaluated in the same manner as the device 1 of the present invention.
  • Comparative element 1 A comparative device 1 was produced in the same manner as the device 1 of the present invention except that the second electron transport layer was changed to BCP alone, and the other compositions were the same as the device 1 of the present invention.
  • a device for comparison 3 was produced with the same composition as the device 1 of the present invention.
  • Light emitting layer using mCP as a host material and Ir (ppy) 3 (tris (2-phenylpyridine) iridium) as a light emitting material, the mass ratio of mCP to Ir (ppy) 3 is 85: 15 It was deposited.
  • a comparative device 4 was produced with the same composition as the device 2 of the present invention.
  • Light emitting layer using hole transporting host material A as a host material and Ir (ppy) 3 as a light emitting material, the mass ratio of hole transporting host material A to Ir (ppy) 3 is 85: 15 As co-evaporated.
  • ⁇ Element 5 of comparison> A comparative device 5 was produced in the same manner as the comparative device 3, except that the material to be doped to the second electron transport layer was changed from Li to Cs, and the other components were the same as the comparative device 3 and the same composition.
  • ⁇ Element of comparison 6> In the same manner as Comparative Example 4 except that the material to be doped in the second electron transport layer was changed from Li to Cs 2 CO 3 , and the others had the same composition as Comparative Example 4 and Comparative Example 6 was fabricated. .
  • a comparative device 7 was produced in the same manner as the device 1 of the present invention except that the second electron transport layer was changed as follows, and the other components were the same as those of the device 1 of the present invention.
  • Second electron transport layer co-evaporation of tris (8-hydroxyquinolinate) aluminum (abbreviated as Alq) and Li instead of BCP so that the doping amount of Li with respect to Alq is 0.4% by mass did.
  • the thickness was 20 nm.
  • Driving Voltage A direct current voltage was applied to each element to emit light, using a source measure unit 2400 manufactured by Toyo Technology Co., Ltd. The voltage at which the value of the current supplied to the device became 10 mA / cm 2 was measured as a drive voltage.
  • Driving durability luminance half time A DC voltage was applied to each element to give a luminance of 1000 cd / m 2, and the device was continuously driven to measure the time until the luminance reached 500 cd / m 2 . The luminance half time was taken as an indicator of driving durability.

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Abstract

L'invention porte sur un élément électroluminescent organique pour lequel une couche de composé organique qui contient au moins une couche électroluminescente, une première couche de transport d'électrons formée en contact avec l'interface côté cathode de la couche électroluminescente susmentionnée, et une seconde couche de transport d'électrons formée en contact avec l'interface côté cathode de la première couche de transport d'électrons susmentionnée, est prise en sandwich entre une paire d'électrodes; la couche électroluminescente susmentionnée contient au moins un matériau électroluminescent représenté par la formule générale (1) et un matériau hôte pouvant transporter les trous; et la seconde couche de transport d'électrons susmentionnée contient un matériau pouvant transporter les électrons représentés par la formule générale (ET) et au moins un type choisi dans un groupe comprenant un métal alcalin, un sel de métal alcalin, un métal alcalinoterreux, et un sel de métal alcalinoterreux.
PCT/JP2009/069543 2008-11-21 2009-11-18 Élément électroluminescent organique Ceased WO2010058787A1 (fr)

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JP2012186392A (ja) * 2011-03-07 2012-09-27 Seiko Epson Corp 発光素子、発光装置、表示装置および電子機器
CN103732602B (zh) * 2011-08-10 2017-02-08 默克专利有限公司 金属络合物
JP2013179293A (ja) * 2012-02-09 2013-09-09 Yamagata Univ 有機電子デバイス及びその製造方法
TWI496330B (zh) * 2012-08-08 2015-08-11 Univ Nat Chiao Tung 製造有機電子元件的裝置及其方法
JP6222712B2 (ja) * 2013-07-10 2017-11-01 株式会社Ｊｏｌｅｄ 有機ｅｌ素子、および有機ｅｌ表示パネル
JP6510223B2 (ja) * 2014-12-11 2019-05-08 株式会社Ｊｏｌｅｄ 有機ｅｌ素子および有機ｅｌ素子の製造方法
WO2017033317A1 (fr) * 2015-08-26 2017-03-02 パイオニア株式会社 Dispositif électroluminescent
JP6815294B2 (ja) * 2016-09-30 2021-01-20 株式会社Ｊｏｌｅｄ 有機ｅｌ素子、および有機ｅｌパネル

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