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WO2010098119A1 - Composé complexe et dispositif électroluminescent organique contenant le composé complexe - Google Patents

Composé complexe et dispositif électroluminescent organique contenant le composé complexe Download PDF

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WO2010098119A1
WO2010098119A1 PCT/JP2010/001300 JP2010001300W WO2010098119A1 WO 2010098119 A1 WO2010098119 A1 WO 2010098119A1 JP 2010001300 W JP2010001300 W JP 2010001300W WO 2010098119 A1 WO2010098119 A1 WO 2010098119A1
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越智貴彦
富樫和彦
関口未散
藤井謙一
田辺良満
戸谷由之
池田潔
佐土貴康
加藤健一
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Mitsui Chemicals Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/022—Boron compounds without C-boron linkages
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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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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    • H10K50/14—Carrier transporting layers

Definitions

  • the present invention relates to a complex compound and an organic electroluminescence device comprising the complex compound.
  • organic electroluminescence element organic electroluminescence element: organic EL element
  • An organic electroluminescent device has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode. By injecting electrons and holes into the thin film and recombining them, an exciton (Exington) ) And emits light using light emitted when the exciton is deactivated.
  • the organic electroluminescence device can emit light at a low direct current voltage of about several V to several tens V, and various colors (for example, red, blue, green) can be selected by selecting the type of the fluorescent organic compound. Light emission is possible.
  • organic electroluminescent elements having such characteristics have been actively applied to various light emitting elements, display elements, and the like. However, generally, there is a demand for an organic electroluminescence device having low emission luminance, practically higher emission efficiency, and long-life emission.
  • organic electroluminescent elements that emit red, blue, and green light with higher color purity have been demanded with the colorization of various display elements.
  • one problem of the organic electroluminescent element is to improve the performance of the red material, and there is a demand for an organic electroluminescent element that emits light with high color purity, high luminous efficiency, and long life.
  • a red light-emitting element in which naphthacene or a pentacene derivative is added to a light-emitting layer is disclosed (see Patent Document 1).
  • This light-emitting element has excellent red purity but has a luminance half-life of about 150 hours. And it was insufficient.
  • the element which added the dicyano methylene type compound to the light emitting layer is disclosed (refer patent document 2), the purity of red was inadequate.
  • the organic film of the organic electroluminescent element is usually manufactured using a vapor deposition method.
  • a composition composed of a plurality of materials is vapor-deposited from the same vapor deposition source (see Patent Document 12, etc.)
  • the device characteristics may be different from those when vapor-deposited from another vapor deposition source.
  • Patent Document 12 describes that when two types of dopant materials are deposited from the same deposition source, the luminous efficiency of the organic electroluminescent element is improved.
  • the inventors have found that when the host material and the dopant material are deposited from the same deposition source in the light emitting layer, for example, the light emission efficiency of the organic electroluminescent device is lowered. At present, there is a demand for a material system that does not change the element characteristics even in such a manufacturing method.
  • Japanese Patent Laid-Open No. 8-311442 Japanese Patent Laid-Open No. 3-162481 JP 2000-86549 A Japanese Patent Laid-Open No. 10-330295 JP 2002-008867 A JP 2001-267078 A Japanese Patent Laid-Open No. 9-118880 JP 2003-12676 A JP 2005-53900 A International Publication No. 2008/047744 Pamphlet JP 11-97180 A JP 2003-068465 A
  • An object of the present invention is to provide a complex compound and an organic electroluminescence device containing the compound. More specifically, providing a complex compound suitable for a light-emitting material of an organic electroluminescence device, etc., having excellent vapor deposition properties, high thermal stability, excellent color purity (long emission wavelength), and high emission efficiency; An organic electroluminescence device using the compound, which is excellent in stability and durability and excellent in color purity and having high luminous efficiency.
  • the present inventors have conducted extensive studies on various complex compounds and organic electroluminescent devices, and as a result, completed the present invention. That is, the first of the present invention relates to the complex compounds shown below.
  • R 1 to R 6 may be the same or different from each other, and are a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; A branched or cyclic alkylthio group; a linear, branched or cyclic alkenyl group; a linear or branched alkynyl group; a substituted or unsubstituted aromatic hydrocarbon group; a substituted or unsubstituted aromatic heterocyclic group; Unsubstituted aralkyl group; substituted or unsubstituted aryloxy group; substituted or unsubstituted arylthio group; substituted or unsubstituted carboxyl group; substituted or unsubstituted silyl group; substituted or unsubstituted amino group; or cyano group Represents.
  • R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6 may be bonded to each other to form a ring.
  • X 1 and X 2 are each a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a linear, branched or cyclic alkenyl group; A branched alkynyl group; a substituted or unsubstituted aromatic hydrocarbon group; a substituted or unsubstituted aryloxy group;
  • R 7 in the general formula (1) is a substituent represented by the general formula (2).
  • Y 1 , Y 2 , Y 3 and Y 4 are each independently a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic fluorinated alkyl group A linear, branched or cyclic alkoxy group; a substituted or unsubstituted aromatic hydrocarbon group; Z represents a single bond, —O— or —S—.
  • n represents an integer of 1 to 10 and m represents an integer of 0 to 10.
  • a plurality of Y 1 , Y 2 , Y 3 and Y 4 are the same as each other. Or different.
  • a in the general formula (2) is a saturated or unsaturated aliphatic cyclic group having 1 to 15 carbon atoms forming a ring; a saturated or unsaturated heterocyclic group having 1 to 15 carbon atoms forming a ring; Alternatively, it represents a linear, branched or cyclic alkyl group having at least one fluorine atom.
  • a substituted aromatic hydrocarbon group or a substituted fragrance includes a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic haloalkyl group; a linear, branched or cyclic alkoxy group; a linear, branched or cyclic group.
  • the substituent of the substituted silyl group is a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; an aromatic hydrocarbon group; Or an aromatic heterocyclic group is meant.
  • the substituent that the substituted amino group has means a linear, branched or cyclic alkyl group; an aromatic hydrocarbon group, or an aromatic heterocyclic group.
  • ⁇ 2> The complex compound according to ⁇ 1>, wherein A is a saturated aliphatic ring group in the general formula (2).
  • ⁇ 3> The complex compound according to ⁇ 1>, in which, in General Formula (2), A is a linear or branched alkyl group having at least one fluorine atom.
  • ⁇ 4> The complex compound according to any one of ⁇ 1> to ⁇ 3>, wherein in general formula (2), Z is a single bond and m is 0.
  • ⁇ 5> Any one of ⁇ 1> to ⁇ 4>, wherein in the general formula (1), any one of R 1 and R 2 , R 5 and R 6 forms a substituted or unsubstituted aromatic ring A complex compound according to any one of the above.
  • ⁇ 6> The complex compound according to any one of ⁇ 1> to ⁇ 5>, wherein in the general formula (1), X 1 and X 2 are fluorine atoms.
  • 2nd of this invention is related with the organic electroluminescent element shown below.
  • ⁇ 7> An organic electroluminescence device comprising at least one layer containing at least one complex compound according to any one of ⁇ 1> to ⁇ 6> between a pair of electrodes.
  • ⁇ 8> The organic electroluminescence device according to ⁇ 7>, wherein the layer containing the complex compound according to any one of ⁇ 1> to ⁇ 6> is a light emitting layer.
  • ⁇ 9> The organic electroluminescence device according to ⁇ 7>, wherein the layer containing the complex compound according to any one of ⁇ 1> to ⁇ 6> is a hole injection transport layer.
  • ⁇ 10> The organic electroluminescence device according to ⁇ 7>, wherein the layer containing the complex compound according to any one of ⁇ 1> to ⁇ 6> is an electron injecting and transporting layer.
  • ⁇ 11> The organic layer according to ⁇ 8>, wherein the layer containing the complex compound according to any one of ⁇ 1> to ⁇ 6> is a light emitting layer, and the light emitting layer is composed of two or more kinds of compounds.
  • Electroluminescent device The organic electroluminescence device according to ⁇ 7>, wherein the layer containing the complex compound according to any one of ⁇ 1> to ⁇ 6> is an electron injecting and transporting layer.
  • the layer containing the complex compound according to any one of ⁇ 1> to ⁇ 6> is a light emitting layer, and further contains a condensed polycyclic hydrocarbon aromatic compound or a condensed polycyclic heterocyclic compound ⁇ 11 > The organic electroluminescent element of>.
  • the present invention it is possible to provide a novel complex compound and an organic electroluminescence device using the compound. More specifically, it is possible to provide a complex compound suitable for a light-emitting material of an organic electroluminescence device, having excellent vapor deposition properties, high thermal stability, excellent color purity (long emission wavelength), and excellent emission efficiency. Furthermore, it is possible to provide an organic electroluminescence device using the compound, which is excellent in stability and durability and excellent in color purity and having high luminous efficiency.
  • the complex compound of the present invention is a compound represented by the general formula (1). That is, the complex compound of the present invention is a complex compound having a pyromethene skeleton and having boron as an acceptor.
  • the substituents R 1 to R 6 , the substituents X 1 to X 2 , and the substituent R 7 in the general formula (1) will be described.
  • R 1 to R 6 in the general formula (1) may be the same as or different from each other.
  • R 1 to R 6 in the general formula (1) are each a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a linear, branched or cyclic alkylthio group; Linear, branched or cyclic alkenyl group; linear or branched alkynyl group; substituted or unsubstituted aromatic hydrocarbon group; substituted or unsubstituted aromatic heterocyclic group; substituted or unsubstituted aralkyl group; A substituted or unsubstituted arylthio group; a substituted or unsubstituted carboxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; or a cyano group.
  • R 1 to R 6 in the general formula (1) are preferably a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms; a linear, branched or branched group having 1 to 20 carbon atoms A cyclic alkoxy group; a linear, branched or cyclic alkylthio group having 1 to 20 carbon atoms; a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms; a linear or branched group having 2 to 20 carbon atoms A substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms; a substituted or unsubstituted aromatic heterocyclic group having 3 to 40 carbon atoms; a substituted or unsubstituted group having 7 to 40 carbon atoms A substituted or unsubstituted aryloxy group having 3 to 50 carbon atoms (wherein aryl represents an aromatic hydrocarbon group or an aromatic hetero
  • R 1 to R 6 in the general formula (1) are more preferably a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms; a linear or branched group having 1 to 10 carbon atoms.
  • R 1 to R 6 in the general formula (1) are more preferably a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms; a linear or branched group having 1 to 10 carbon atoms. Or a cyclic alkoxy group; a substituted or unsubstituted aromatic hydrocarbon group having 6 to 45 carbon atoms; a substituted or unsubstituted aromatic heterocyclic group having 3 to 35 carbon atoms; a substitution having 1 to 35 carbon atoms A substituted amino group having 1 to 30 carbon atoms: or a cyano group.
  • R 1 to R 6 may be bonded to adjacent substituents to form a ring. That is, R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6 may be bonded to each other to form a ring.
  • R 1 and R 2 , and R 5 and R 6 form a substituted or unsubstituted aromatic ring; more preferably, a combination of either R 1 and R 2 , or R 5 and R 6 is A substituted or unsubstituted aromatic ring is formed.
  • Examples of the ring formed by combining R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , or R 5 and R 6 with each other include the following 1-1 to 1-10: Preferably 1-1 to 1-3; more preferably 1-1 and 1-2.
  • R 1 to R 7 , X 1 and X 2 are defined in the same manner as in the general formula (1).
  • R 11 to R 18 , R 21 to R 28 , R 31 to R 37 and R 41 to R 47 are (Defined in the same manner as R 1 to R 6 in the general formula (1))
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group.
  • substituent that the aromatic hydrocarbon group or the aromatic heterocyclic group may have include a halogen atom; a linear, branched, or cyclic alkyl group; a linear, branched, or cyclic haloalkyl group; A branched or cyclic alkoxy group; a linear, branched or cyclic alkylthio group; an aromatic hydrocarbon group (which may be further mono- or polysubstituted by an alkyl group, an alkoxy group or an aromatic hydrocarbon group); An aromatic heterocyclic group (which may be mono- or polysubstituted by an alkyl group, an alkoxy group or an aromatic hydrocarbon group); an aralkyl group (further an alkyl group, an alkoxy group or an aromatic hydrocarbon group) Mono- or poly-
  • Examples of preferred substituents that the aromatic hydrocarbon group or the aromatic heterocyclic group may have include a linear, branched or cyclic alkyl group; a linear, branched or cyclic haloalkyl group; a linear, branched or cyclic group.
  • Examples of more preferable substituents that the aromatic hydrocarbon group or the aromatic heterocyclic group may have include a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms; a linear chain having 1 to 20 carbon atoms.
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted silyl group.
  • the substituent that the silyl group may have include a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a substituted or unsubstituted aromatic hydrocarbon group (here Substituted or unsubstituted is synonymous with the substituent mentioned in the substituent of the substituted or unsubstituted aromatic hydrocarbon group; or substituted or unsubstituted aromatic heterocyclic group (where substituted or unsubstituted is substituted) Or the same as the substituents mentioned for the substituent of the unsubstituted aromatic heterocyclic group).
  • Examples of preferred substituents that the silyl group may have include a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms; a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms; a carbon atom A substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 carbon atoms; a substituted or unsubstituted aromatic heterocyclic group having 3 to 50 carbon atoms.
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted amino group.
  • substituents that the amino group may have include a linear, branched or cyclic alkyl group; a substituted or unsubstituted aromatic hydrocarbon group (where substituted or unsubstituted aromatic is a substituted or unsubstituted aromatic group). Or substituted or unsubstituted aromatic heterocyclic group (where substituted or unsubstituted is substituted with substituted or unsubstituted aromatic heterocyclic group). Which is the same as the substituents mentioned in the group).
  • amino group may have include linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted aromatic hydrocarbon groups having 6 to 50 carbon atoms; carbon A substituted or unsubstituted aromatic heterocyclic group having 3 to 50 atoms is included.
  • halogen atom represented by R 1 to R 6 in the general formula (1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • R 1 to R 6 in the general formula (1) may be a linear, branched or cyclic alkyl group.
  • Specific examples of the alkyl group represented by R 1 to R 6 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, and n-pentyl group.
  • alkyl group of R 1 to R 6 examples include methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-octyl Oxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group, 2-n- Pentyloxyethyl group, 2-n-hexyloxyethyl group, 2- (2'-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2 ' -Ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group, 2-
  • alkyl group represented by R 1 to R 6 include benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4′-methylbenzyloxy) ethyl group, 2 -(2'-methylbenzyloxy) ethyl group, 2- (4'-fluorobenzyloxy) ethyl group, 2- (4'-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4 ' Includes alkyl groups having an aralkyloxy group, such as -methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) ethyl group, and 2- (4'-methylbenzyloxymethoxy) ethyl group It is.
  • alkyl group represented by R 1 to R 6 examples include a phenyloxymethyl group, a 4-methylphenyloxymethyl group, a 3-methylphenyloxymethyl group, a 2-methylphenyloxymethyl group, and a 4-methoxyphenyl group.
  • alkyl group represented by R 1 to R 6 include an n-butylthiomethyl group, an n-hexylthiomethyl group, a 2-methylthioethyl group, a 2-ethylthioethyl group, and a 2-n-butylthio group.
  • Ethyl group 2-n-hexylthioethyl group, 2-n-octylthioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group Group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group, 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n -Butylthiohexyl group, 8-methylthiooctyl group, 2- (2'-methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl Group, 2-allylthio
  • alkyl group represented by R 1 to R 6 include an alkyl group having a halogen atom.
  • alkyl group having a halogen atom include fluoromethyl group, 6-fluorohexyl group, trifluoromethyl group, perfluoroethyl group, perfluoro-n-propyl group, perfluoro-n-hexyl group, 6- Alkyl groups having fluorine atoms such as fluorohexyl group, 4-fluorocyclohexyl group; dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chlorooctyl group An alkyl group having a chlorine atom such as a 2,2,2-trichloroethyl group is included.
  • alkyl group represented by R 1 to R 6 include 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxy group.
  • Alkyl groups having a hydroxyl group such as a hexyl group, a 5-hydroxyheptyl group, an 8-hydroxyoctyl group, a 10-hydroxydecyl group, a 12-hydroxydodecyl group, and a 2-hydroxycyclohexyl group are included.
  • R 1 to R 6 in the general formula (1) may be a linear, branched or cyclic alkoxy group, or a linear, branched or cyclic alkylthio group.
  • alkoxy or alkylthio group of R 1 ⁇ R 6 include, but are alkoxy group or alkylthio group derived from the alkyl groups shown as the specific examples of the alkyl group of R 1 ⁇ R 6, limited to Not.
  • R 1 to R 6 in the general formula (1) may be a linear, branched or cyclic alkenyl group.
  • alkenyl group represented by R 1 to R 6 include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclo A hydrocarbon group containing a double bond, such as a pentenyl group, is included.
  • R 1 to R 6 in the general formula (1) may be a linear or branched alkynyl group.
  • the alkynyl group of R 1 to R 6 include an acetylenyl group, a propynyl group, a 1-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 2-methyl-1-pentynyl group, and a phenylacetylenyl group.
  • a hydrocarbon group containing a triple bond include an acetylenyl group, a propynyl group, a 1-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 2-methyl-1-pentynyl group, and a phenylacetylenyl group.
  • a hydrocarbon group containing a triple bond may be a hydrocarbon group containing a triple bond.
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group. Although the specific example is shown below, it is not necessarily limited to these.
  • aromatic hydrocarbon group of R 1 to R 6 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 4-phenyl-1-naphthyl group, a 6-phenyl-2-naphthyl group, a 2- Anthracenyl group, 9-anthracenyl group, 9-methyl-10-anthracenyl group, 9-phenyl-10-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group 9-methyl-10-phenanthryl group, 9-phenyl-10-phenanthryl group, 1-methyl-9-phenanthryl group, 1-phenyl-9-phenanthryl group, 2-methyl-9-phenanthryl group, 2-phenyl- 9-phenanthryl group, 1,8-dimethyl-9-phenanthryl group, 1,8-diphenyl
  • aromatic hydrocarbon group of R 1 to R 6 include 1-pyrenyl group, 2-pyrenyl group, 1-phenyl-2-pyrenyl group, 1-methyl-2-pyrenyl group, 2-phenyl -1-pyrenyl group, 2-methyl-1-pyrenyl group, 4,5-dimethyl-1-pyrenyl group, 6-phenyl-1-pyrenyl group, 6-methyl-1-pyrenyl group, 6-tert-butyl- 1-pyrenyl group, 6-cyclohexyl-1-pyrenyl group, 7-phenyl-1-pyrenyl group, 7-methyl-1-pyrenyl group, 7-phenyl-2-pyrenyl group, 7-methyl-2-pyrenyl group, 7-tert-butyl-2-pyrenyl group, 1,8-diphenyl-2-pyrenyl group, 1,8-dimethyl-2-pyrenyl group, 5,9-dicyclohexyl-2-pyrenyl group, 3,6-
  • aromatic hydrocarbon group of R 1 to R 6 examples include a 2-perylenyl group, a 3-perylenyl group, a 2-fluoranthenyl group, a 3-fluoranthenyl group, a 7-fluoranthenyl group, An 8-fluoranthenyl group and the like are included.
  • aromatic hydrocarbon group of R 1 to R 6 include 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2 -Ethylphenyl group, 4-n-propylphenyl group, 2-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec -Butylphenyl group, 2-sec-butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, 2-tertbutylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group 2-neopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 3-n-
  • aromatic hydrocarbon group of R 1 to R 6 include 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2 -Ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 3-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2- Neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2′-ethylbutyloxy) phenyl group, 4-n-octyloxy
  • aromatic hydrocarbon group of R 1 to R 6 examples include a 4-phenylphenyl group, a 3-phenylphenyl group, a 2-phenylphenyl group, a 2,6-diphenylphenyl group, and a 3,5-diphenyl group.
  • aromatic hydrocarbon group of R 1 to R 6 examples include a 4-fluorophenyl group, a 3-fluorophenyl group, a 2-fluorophenyl group, a 4-chlorophenyl group, a 3-chlorophenyl group, and a 2-chlorophenyl group.
  • aromatic hydrocarbon group of R 1 to R 6 examples include 3-N, N-diphenylaminophenyl group, 4-N, N-diphenylaminophenyl group, 6-N, N-diphenylamino-
  • aromatic hydrocarbon group having a diarylamino group such as a 2-naphthyl group and a 4-N, N-diphenylamino-1-naphthyl group is included.
  • aromatic hydrocarbon group of R 1 to R 6 include 9,9-dimethyl-9H-fluoren-2-yl group, 9,9-diethyl-9H-fluoren-2-yl group, 9 , 9-Di-n-hexyl-9H-fluoren-2-yl group, 9,9-di-n-octyl-9H-fluoren-2-yl group, 9,9-diphenyl-9H-fluoren-2-yl Group, 9,9-dicyclohexyl-9H-fluoren-2-yl group, 9,9-dibenzyl-9H-fluoren-2-yl group, 7-N, N-diphenylamino-9,9-dimethyl-9H-fluorene Fluorenyl groups are included, such as a -2-yl group.
  • aromatic hydrocarbon group represented by R 1 to R 6 include 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, and 3,5-bistrifluoromethyl. Includes phenyl group, 4-perfluoroethylphenyl group, 2-methylthiophenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group, 4-ethylthiophenyl group, 4-cyanophenyl group, 3-cyanophenyl group, etc. It is.
  • aromatic hydrocarbon group of R 1 to R 6 examples include 2-trimethylsilylphenyl group, 3-trimethylsilylphenyl group, 4-trimethylsilylphenyl group, 3,5-bistrimethylsilylphenyl group, and 4-triethylsilyl group.
  • Examples of the aromatic heterocyclic group of R 1 to R 6 include a 4-quinolinyl group, a 3-quinolinyl group, a 2-quinolinyl group, a 1-phenyl-isoquinolin-3-yl group, and a 2-phenyl-7-naphthyridinyl group.
  • 2-phenanthrolinyl group 4-pyridinyl group, 3-pyridinyl group, 2-pyridinyl group, 2-phenyl-5-pyridyl group, 2-phenyl-4-pyridyl group, 2,5-diphenyl-4- Pyridyl group, 2- (2′-pyridyl) -5-pyridyl group, 2,5-di (2′-pyridyl) -4-pyridyl group, 2-ethyl-6-phenyl-4-pyridyl group, 2,3 , 4-triphenyl-6-pyridyl group, 3-ethyl-4-pyridyl group, 2-pyrimidinyl group, 2-phenyl-5-pyrimidinyl group, 2- (2 ′, 6′-dimethylphenyl) -5-pyrimidinyl Group, 4,5-diphenyl-2-pyrimidinyl group, 2-pyridazinyl group, 2-pyrazinyl group, 4,6-diphen
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted aralkyl group.
  • aralkyl groups of R 1 to R 6 include benzyl group, ⁇ -methylbenzyl group, ⁇ -ethylbenzyl group, phenethyl group, ⁇ -methylphenethyl group, ⁇ -methylphenethyl group, ⁇ , ⁇ -dimethylbenzyl.
  • R 1 to R 6 include 4-allylbenzyl group, 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, 4- (4′-methylphenyl) benzyl.
  • Aralkyl groups having aryl groups or aralkyl groups, such as groups, are included.
  • aralkyl group of R 1 to R 6 examples include a 4-methoxybenzyl group, a 2-methoxybenzyl group, a 2-ethoxybenzyl group, a 4-n-butoxybenzyl group, and a 4-n-heptyloxybenzyl group.
  • An aralkyl group having:
  • aralkyl groups of R 1 to R 6 include aralkyl groups having a hydroxyl group such as a 4-hydroxybenzyl group, a 3-hydroxybenzyl group, a 2-hydroxybenzyl group, and a 4-hydroxy-3-methoxybenzyl group.
  • aralkyl groups having a halogen atom such as 4-fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, and 3,4-dichlorobenzyl group.
  • aralkyl group of R 1 to R 6 examples include a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, and the like.
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted arylthio group.
  • the aryloxy group or arylthio group R 1 ⁇ R 6 are specific examples of the substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, the R 1 ⁇ R 6 Listed substituted or unsubstituted aromatic hydrocarbon groups, or substituted or unsubstituted aryloxy groups derived from substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted arylthio groups However, it is not limited to these.
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted carboxyl group.
  • Specific examples of the carboxyl group of R 1 to R 6 include, but are not limited to, carboxyl group, methyl carboxyl group, ethyl carboxyl group, phenyl carboxyl group, isopropyl carboxyl group, 1-n-butenyl carboxyl group, and the like. Not.
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted silyl group.
  • the silyl group of R 1 to R 6 include silyl group, methylsilyl group, dimethylsilyl group, trimethylsilyl group, diethylmethylsilyl group, ethyldimethylsilyl group, triethylsilyl group, tri-n-propylsilyl group, tri- Isopropylsilyl group, cyclohexyldimethylsilyl group, dimethylmethoxysilyl group, methyldimethoxysilyl group, trimethoxysilyl group, dimethylethoxysilyl group, dimethyl n-propoxysilyl group, dimethylisopropoxysilyl group, dimethylphenylsilyl group, methyldiphenyl Examples include, but are not limited to, a silyl group, a triphenylsilyl group, a dimethyl-p-
  • R 1 to R 6 in the general formula (1) may be a substituted or unsubstituted amino group.
  • Specific examples of the amino group of R 1 to R 6 include an unsubstituted amino group; N-methylamino group, N-ethylamino group, Nn-propylamino group, N-isopropylamino group, Nn- Butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentylamino group, Nn-hexylamino group, N- An amino group having an alkyl group, such as a cyclohexylamino group, is included.
  • amino group of R 1 to R 6 include N-benzylamino group, N-phenethylamino group, N-phenylamino group, N- (1-naphthyl) amino group, N- (2-naphthyl).
  • Amino group N- (4-phenylphenyl) amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group, N- (4-methylphenyl) amino group, N- Examples include an amino group having an aralkyl group or an aryl group, such as a (2-methylphenyl) amino group, an N- (2-anthracenyl) amino group, and an N- (9-anthracenyl) amino group.
  • amino group of R 1 to R 6 include N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group, N, N-di-isopropyl.
  • N-di-n-butylamino group N, N-di-isobutylamino group, N, N-di-sec-butylamino group, N, N-di-n-pentylamino group, N , N-dicyclopentylamino group, N, N-dicyclohexylamino group, N, N-dibenzylamino group, N, N-diphenethylamino group, N-methyl-N-ethylamino group, N-methyl-N- n-propylamino group, N-methyl-N-isopropylamino group, N-methyl-N-n-butylamino group, N-methyl-N-tert-butylamino group, N-methyl-N-cyclopentylamino group, N-methyl-N-cyclohexylamino group, N-methyl-N-benzylamino group, N-methyl-N-phen
  • amino group of R 1 to R 6 include N, N-diphenylamino group, N-phenyl-N- (4-methylphenyl) amino group, N-phenyl-N- (3-methylphenyl). ) Amino group, N-phenyl-N- (2-methylphenyl) amino group, N-phenyl-N- (4-methoxyphenyl) amino group, N-phenyl-N- (3-methoxyphenyl) amino group, N -Phenyl-N- (2-methoxyphenyl) amino group, N-phenyl-N- (1-naphthyl) amino group, N-phenyl-N- (2-naphthyl) amino group, N-phenyl-N- (4 -Phenyl-1-naphthyl) amino group, N-phenyl-N- (4-phenylphenyl) amino group, N-phenyl-N- (3-phenylphenyl) amino group
  • amino group of R 1 to R 6 include an N-carbazolyl group, 3,6-dimethyl-N-carbazolyl group, 3,6-diphenyl-N-carbazolyl group, 3,6-bis (N , N-diphenylamino) -N-carbazolyl group, 3,6-bis [N-phenyl-N- (1′-naphthyl) amino] -N-carbazolyl group, 3,6-bis [N-phenyl-N— (4′-phenylphenyl) amino] -N-carbazolyl group, 3,6-bis [N-carbazolyl] -N-carbazolyl group, 3- (N, N-diphenylamino) -N-carbazolyl group, 3- ( N, N-diphenylamino) -6-phenyl-N-carbazolyl group, 3- [N-phenyl-N- (1′-naphthyl
  • amino group of R 1 to R 6 include an N-phenothiazinyl group and an N-phenoxazinyl group.
  • X 1 and X 2 in the general formula (1) are each independently a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a linear, branched or cyclic alkenyl group; A linear or branched alkynyl group; a substituted or unsubstituted aromatic hydrocarbon group; a substituted or unsubstituted aryloxy group.
  • X 1 and X 2 in the general formula (1) are preferably each independently a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a substituted or unsubstituted aryl group Represents a substituted or unsubstituted aryloxy group.
  • X 1 and X 2 in the general formula (1) are more preferably each independently a fluorine atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a substituted or unsubstituted aryl Group represents a substituted or unsubstituted aryloxy group.
  • X 1 and X 2 in the general formula (1) more preferably represent a fluorine atom.
  • X 1 and X 2 in the general formula (1) may be a substituted or unsubstituted aromatic hydrocarbon group.
  • the aromatic hydrocarbon group may have include a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic haloalkyl group; a linear, branched or cyclic alkoxy group; Chain, branched or cyclic alkylthio groups; aromatic hydrocarbon groups; aromatic heterocyclic groups; aralkyl groups; aryloxy groups; arylthio groups; substituted or unsubstituted silyl groups; or substituted or unsubstituted amino groups It is.
  • a halogen atom of X 1 and X 2 a linear, branched or cyclic alkyl group; a linear, branched or cyclic alkoxy group; a linear, branched or cyclic alkenyl group; a linear or branched alkynyl group;
  • Specific examples of a substituted aryl group; a substituted or unsubstituted aryloxy group include the halogen atoms listed as specific examples of R 1 to R 6 ; a linear, branched, or cyclic alkyl group; a linear, branched, or cyclic group.
  • Examples include, but are not limited to, alkoxy groups; linear, branched or cyclic alkenyl groups; linear or branched alkynyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted aryloxy groups. is not.
  • R 7 in the general formula (1) is a substituent represented by the general formula (2).
  • R 7 in the general formula (1) is a substituent represented by the general formula (2).
  • n represents an integer of 1 to 10
  • m represents an integer of 0 to 10.
  • n represents an integer of 1 to 6
  • m represents an integer of 0 to 6.
  • n represents an integer of 1 to 3
  • m represents an integer of 0 to 3.
  • n in the general formula (2) is 2 or more, a plurality of Y 1 and Y 2 may be the same or different from each other.
  • m in General Formula (2) is 2 or more, a plurality of Y 3 and Y 4 may be the same or different from each other.
  • Y 1 , Y 2 , Y 3 and Y 4 in the general formula (2) are each independently a hydrogen atom; a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic fluorinated alkyl.
  • Y 1 , Y 2 , Y 3 and Y 4 in the general formula (2) may be a substituted or unsubstituted aromatic hydrocarbon group.
  • Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom; a linear, branched or cyclic alkyl group; a linear, branched or cyclic haloalkyl group; a linear, branched or cyclic alkoxy group.
  • halogen atom, alkyl group, alkoxy group, and aromatic hydrocarbon group of Y 1 , Y 2 , Y 3 and Y 4 in the general formula (2) include R 1 to R 6 in the general formula (1).
  • Specific examples include, but are not limited to, halogen atoms, alkyl groups, alkoxy groups, and aromatic hydrocarbon groups.
  • the fluorinated alkyl group represented by Y 1 , Y 2 , Y 3 and Y 4 in the general formula (2) is one in which all hydrogen atoms in the alkyl group are substituted with fluorine atoms (perfluoroalkyl group), and an alkyl group Any in which some of the hydrogen atoms are substituted with fluorine atoms is preferred.
  • fluorinated alkyl group examples include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, perfluoroethyl group, perfluoro-n-propyl group, perfluoro-n-butyl group, perfluoro-n.
  • -Pentyl group 2,2,2-trifluoroethyl group, 3,3,3-trifluoro-n-propyl group, 2,2,3,3,3-pentafluoro-n-propyl group, 1H, 1H -Nonafluoro-n-pentyl group and the like.
  • Z in the general formula (2) represents a single bond, —O— or —S—, preferably a single bond.
  • a in the general formula (2) is a saturated or unsaturated aliphatic cyclic group having 1 to 15 carbon atoms forming a ring; a saturated or unsaturated heterocyclic group having 1 to 10 carbon atoms forming a ring; Alternatively, it represents a linear, branched or cyclic alkyl group having at least one fluorine atom.
  • the number of carbon atoms constituting the ring of the “saturated or unsaturated aliphatic ring group” is preferably 1 to 12.
  • the number of carbon atoms constituting the ring of the “saturated or unsaturated heterocyclic group” is preferably 1-8.
  • A preferably represents a saturated or unsaturated aliphatic ring group; or a linear, branched or cyclic alkyl group having at least one fluorine atom.
  • A represents more preferably a saturated aliphatic ring group; or a linear or branched alkyl group having at least one fluorine atom.
  • saturated or unsaturated aliphatic ring group represented by A include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a 1-norbornyl group, 2-norbornyl group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, 1-cyclooctenyl group, 1,3-cyclohexadienyl group, 1 , 5-cyclooctadienyl group and the like, but is not limited thereto.
  • saturated or unsaturated heterocyclic group represented by A include 2-thienyl group, 3-furyl group, 2H-pyran-3-yl group, 1-isobenzofuranyl group, 2-imidazolyl group, 3 -Isothiazoyl group, 2-pyridyl group, pyrimidinyl group, 3-indolidinyl group, 1-indolyl group, 3-indolyl group, 3H-indol-2-yl group, 3-furazanyl group, 2-quinolinolyl group, 2-quinoxalinyl group Examples include, but are not limited to, a 3-isoquinolinolyl group.
  • linear, branched or cyclic alkyl group having at least one fluorine atom represented by A include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, and a perfluoro-n-propyl group.
  • the number of carbon atoms of the substituent represented by the general formula (2) is preferably 4 to 40, more preferably 5 to 30, and still more preferably 6 to 20.
  • Specific examples of the substituent represented by the general formula (2) include, but are not limited to, the following substituents (2-1 to 2-68).
  • the substituent represented by the general formula (2) is a substituent (2-1 to 2-8, 2-24 to 2-29, 2-35, 2-41 to 2-47, 2-57. 2-58, 2-63, 2-65 to 2-67), and more preferably (2-1 to 2-8, 2-25 to 2-29).
  • complex compound represented by the general formula (1) according to the present invention include the following compounds (Exemplary compounds A-1 to A-62, B-1 to B-8, C-1 to C— 16, D-1 to D-8, E-1 to E-16, F-1 to F-34, G-1 to G-8, and H-1 to H-8). Not.
  • the complex compound represented by the general formula (1) of the present invention can be produced by a method known per se. For example, it can be produced by the method described in J. Org. Chem, 72, 269, (2007). That is, for example, the pyrrole compound represented by the general formula (3) or the general formula (4) is acylated [for example, Tetrahedron Letters, 30, 241, (1989), Tetrahedron Letters, 43, 8133, (2002), J Org. Chem, 72, 269, (2007) can be referred to].
  • the acylated compound represented by the general formula (5) is reacted with the compound represented by the general formula (4), or the acylated compound represented by the general formula (6) and the general formula (3)
  • a dipyrromethene compound represented by the general formula (7) is obtained by reacting with the compound represented.
  • the reaction may be performed, for example, in the presence of phosphorus oxychloride, hydrobromic acid, etc., in a solvent such as 1,2-dichloroethane, if desired [for example, the method described in J. Org. Chem, 72, 269, (2007) Can be referred to].
  • the complex compound represented by the general formula (1) can be obtained by reacting the compound represented by the general formula (7) with a boron halide derivative (for example, boron trifluoride diethyl ether complex).
  • a boron halide derivative for example, boron trifluoride diethyl ether complex.
  • R 1 to R 6 represent the same meaning as in the general formula (1) and R 7 )
  • the organic electroluminescence device usually has at least one light emitting layer containing at least one light emitting component sandwiched between a pair of electrodes.
  • a charge injection transport layer such as an electron injection transport layer containing a transport component can also be provided.
  • the light emitting layer is a hole injection transport layer and / or an electron injection transport layer.
  • a type of element configuration that also serves as a single layer type element configuration.
  • a two-layer element configuration in which a hole injection transport layer is provided on the anode side of the light emitting layer may be adopted.
  • the light-emitting layer does not have a sufficient electron injection function and / or electron transport function
  • a two-layer device structure in which an electron injection / transport layer is provided on the cathode side of the light-emitting layer can be obtained.
  • a three-layer element configuration in which the light-emitting layer is sandwiched between a hole injecting and transporting layer and an electron injecting and transporting layer may be employed.
  • each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single layer structure or a multilayer structure; the hole injecting and transporting layer and the electron injecting and transporting layer
  • the layer having an injection function and the layer having a transport function can be separately provided.
  • the organic electroluminescent device of the present invention at least one layer containing at least one complex compound represented by the general formula (1) is sandwiched between a pair of electrodes.
  • the organic electroluminescent element of the present invention contains the complex compound represented by the general formula (1) as a component of the charge injection / transport layer (hole injection / transport layer and / or electron injection / transport layer) and / or the light-emitting layer. It is preferable to contain it as a constituent component of the light emitting layer.
  • the complex compound represented by the general formula (1) may be used alone or in combination.
  • the layer structure of the organic electroluminescent element of the present invention is not particularly limited.
  • EL-1 anode / hole injection transport layer / light emitting layer / electron injection transport layer / cathode type element shown in FIG.
  • EL-2 Anode / hole injection / transport layer / light emitting layer / cathode-type device shown in FIG.
  • EL-3 Anode
  • an anode / hole injection / transport layer / electron injection / transport layer / light emitting layer / electron injection / transport layer / cathode-type device (EL-5) having a light emitting layer sandwiched between electron injection / transport layers, etc. Can be mentioned.
  • the element configuration (EL-4) of the organic electroluminescent element of the present invention is: An element of a type in which a light emitting component is sandwiched between a pair of electrodes as a light emitting layer: A device (EL-6) of the type shown in FIG. 6 sandwiched between a pair of electrodes in a single layer form in which a hole injection transport component, a light emission component and an electron injection component are mixed as a light emitting layer: As shown in FIG. 7, a type of element (EL-7) sandwiched between a pair of electrodes in a single layer form in which a hole injecting and transporting component and a light emitting component are mixed as a light emitting layer: As shown in FIG. 8, the light emitting layer may be a type of element (EL-8) sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injection component are mixed.
  • the layer configuration of the organic electroluminescent device of the present invention is not limited to these device configurations, and each type of device may be provided with a plurality of hole injection transport layers, light emitting layers, and electron injection transport layers. . Further, in each type of device, the hole injection / transport layer is disposed between the light emitting layer, the hole injection / transport component and the light emitting component mixed layer and / or the light emitting layer and the electron injection / transport layer between the light emitting component and the light emitting component. And a mixed layer of electron injecting and transporting components can be provided.
  • Preferred configurations of the organic electroluminescent device of the present invention include (EL-1) type device, (EL-2) type device, (EL-5) type device, (EL-6) type device or (EL-7) type. More preferably, it is an (EL-1) type element, an (EL-2) type element or an (EL-7) type element.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injecting and transporting layer
  • 4 is a light emitting layer
  • 5 is an electron injecting and transporting layer
  • 6 is a cathode
  • 7 is a power source.
  • the organic electroluminescent element of the present invention is preferably supported on the substrate 1.
  • the substrate is not particularly limited, but a transparent or translucent substrate is preferable.
  • the material of the substrate include soda lime glass and borosilicate glass, and transparent polymers such as polyester, polycarbonate, polysulfone, polyethersulfone, polyacrylate, polymethyl methacrylate, polypropylene, and polyethylene.
  • the substrate may be a translucent plastic sheet, quartz, transparent ceramics, or a composite sheet combining these.
  • the emission color can be controlled by combining, for example, a color filter film, a color conversion film, or a dielectric reflection film with the substrate.
  • the electrode material of the anode 2 is preferably a metal, alloy or conductive compound having a relatively large work function.
  • electrode materials used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In 2 O 3 ), tin oxide (SnO 2 ), zinc oxide, ITO ( Indium tin oxide (Indium Tin Oxide), polythiophene, polypyrrole, and the like are included. These electrode materials may be used alone or in combination. These electrode materials can be disposed on the substrate by a method such as vapor deposition or sputtering to form an anode.
  • the anode may have a single layer structure or a multilayer structure.
  • the sheet electrical resistance of the anode is preferably several hundred ⁇ / ⁇ or less, and more preferably set to about 5 to 50 ⁇ / ⁇ .
  • the thickness of the anode is generally set to about 5 to 1000 nm, more preferably about 10 to 500 nm, although it depends on the material of the electrode material.
  • the hole injection transport layer 3 contains a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes.
  • the hole injection / transport layer of the electroluminescent element of the present invention contains at least one complex compound represented by the general formula (1) and / or another compound having a hole injection / transport function.
  • Examples of compounds having other hole injecting and transporting functions include phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazole derivatives, hydrazone derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and its derivatives, polythiophene And derivatives thereof, poly-N-vinylcarbazole and the like.
  • the compounds having a hole injecting and transporting function may be used alone or in combination.
  • More preferable examples of the compound having a hole injecting and transporting function other than the complex compound represented by the general formula (1) of the present invention that can be used in the organic electroluminescence device of the present invention include a triarylamine derivative, Polythiophene and its derivatives, poly-N-vinylcarbazole and its derivatives are included.
  • Specific examples of triarylamine derivatives include 4,4′-bis [N-phenyl-N- (4 ”-methylphenyl) amino] -1,1′-biphenyl, 4,4′-bis [N-phenyl].
  • the inclusion of the complex compound represented by the general formula (1) in the hole injection transport layer is preferably 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, still more preferably 3 to 97% by weight.
  • the light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.
  • a light emitting layer contains at least 1 type of the compound which has a complex compound represented by General formula (1), and / or the other light emission function.
  • Examples of compounds having a light emitting function other than the complex compound represented by the general formula (1) include acridone derivatives, quinacridone derivatives, diketopyrrolopyrrole derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes, Stilbene derivatives, coumarin derivatives, pyran derivatives (eg DCM1, DCM2), anthracene derivatives, oxazone derivatives (eg Nile Red), benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamate derivatives, poly -N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polybiphenylene vinylene and derivatives thereof Conductor, poly terpolymers phenylene vinylene and derivatives thereof, poly nap
  • polycyclic aromatic compounds having a light-emitting function examples include rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10 -Bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthcenyl) benzene, 4,4'-bis (9 "-ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1 , 2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivatives and the like.
  • triarylamine derivatives having a light emitting function examples include the compounds described above as compounds having a hole injecting and transporting function.
  • organometallic complexes having a light-emitting function examples include tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2- (2′-hydroxyphenyl) benzothiazole zinc salt, 4-hydroxy Examples include zinc salt of acridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone, and the like.
  • stilbene derivatives having a light emitting function examples include 1,1,4,4-tetraphenyl-1,3-butadiene, 4,4′-bis (2,2-diphenylvinyl) biphenyl, and 4,4′-bis. [(1,1,2-triphenyl) ethenyl] biphenyl and the like are included.
  • Examples of coumarin derivatives having a light emitting function include coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin 153, coumarin 307, coumarin 311, coumarin 314, coumarin 334, Coumarin 338, Coumarin 343, Coumarin 500 and the like are included.
  • anthracene derivatives having a light-emitting function examples include 9,10-bis (2′-naphthyl) anthracene derivatives, 9,10-bis (1 ′, 1 ′′ -bis-3′-biphenyl) anthracene derivatives, and the like. .
  • the compound having a light emitting function other than the complex compound represented by the general formula (1) is preferably an acridone derivative, a quinacridone derivative, a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex, or a stilbene derivative; More preferred are compounds, triarylamine derivatives, and organometallic complexes.
  • the light emitting layer of the organic electroluminescent element of this invention contains the compound of a phosphorescence (triplet light emission) luminescent property as a compound which has light emission functions other than the complex compound represented by General formula (1). Good.
  • Examples of phosphorescent compounds include tris (2-phenylpyrimidyl) iridium complex, tris [2- (2′-fluorophenyl) pyridyl] iridium complex, bis (2-phenylpyridyl) acetylacetonatoiridium complex Bis [2- (2 ′, 4′-difluorophenyl) pyridyl] acetylacetonatoiridium complex, 2,3,7,8,12,13,17,18-octaethyl-21H, 23H porphyrin platinum complex, etc. It is.
  • the organic electroluminescent element of the present invention preferably contains a complex compound represented by the general formula (1) in the light emitting layer.
  • a complex compound represented by the general formula (1) in the light emitting layer.
  • the complex represented by the general formula (1) in the light emitting layer The proportion of the compound is preferably adjusted to 0.001 to 99.999% by weight.
  • the light emitting layer may contain a combination of a host compound and a guest compound (dopant material) as described in J. Appl. Phys., 65, 3610 (1989) and JP-A-5-214332. Good.
  • the complex compound represented by the general formula (1) can be used as a host compound of the light emitting layer, and can also be used as a guest compound.
  • the guest compound may be, for example, a compound having the above other light emitting function, but is a polycyclic aromatic compound. It is preferable.
  • the host compound is a condensed polycyclic hydrocarbon aromatic compound, a condensed polycyclic heterocyclic compound, a triarylamine derivative, an organic metal.
  • a complex or a stilbene derivative more preferably a triarylamine derivative, a condensed polycyclic hydrocarbon aromatic compound, a condensed polycyclic heterocyclic compound, or an organometallic complex; a condensed polycyclic hydrocarbon aromatic compound, or A condensed polycyclic heterocyclic compound is more preferable.
  • condensed polycyclic hydrocarbon aromatic compounds include naphthacene derivatives, anthracene derivatives, pentacene derivatives, perylene derivatives, chrysene derivatives, and the like.
  • condensed polycyclic heterocyclic compound include quinoline derivatives and carbazole derivatives.
  • the organic electroluminescent element of the present invention preferably contains a complex compound represented by the general formula (1) as a guest compound in the light emitting layer.
  • the complex compound represented by the general formula (1) when used as a guest compound, the light emitting layer preferably contains 0.001 to 40% by weight of the complex compound represented by the general formula (1). The content is more preferably 0.01 to 30% by weight, and still more preferably 0.1 to 20% by weight.
  • the light emitting layer is formed using the complex compound represented by the general formula (1) as a host compound, it is preferably 0.001 to 40% by weight, more preferably based on the complex compound represented by the general formula (1). 0.01 to 30% by weight, more preferably 0.1 to 20% by weight of guest compound is used.
  • the content of the complex compound represented by the general formula (1) in the light emitting layer is preferably It is 40.0% to 99.9% by weight, and more preferably 60.0 to 99.9% by weight.
  • the amount of the guest material used is 0.001 to 40% by weight, preferably 0.05 to 30% by weight, more preferably 0.1 to 20% by weight with respect to the complex compound represented by the general formula (1). % By weight.
  • the complex compound represented by General formula (1) may be used independently, and may be used together.
  • the electron injection / transport layer 5 is a layer containing a compound having a function of facilitating injection of electrons from the cathode and / or a function of transporting injected electrons.
  • the compound having an electron injecting and transporting function that can be used in the organic electroluminescence device of the present invention may be a complex compound represented by the general formula (1) or other compounds.
  • Examples of compounds having an electron injecting and transporting function other than the complex compound represented by the general formula (1) include organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenyl Examples include quinone derivatives, nitro-substituted fluorenone derivatives, and thiopyrandioxide derivatives.
  • organometallic complexes having an electron injecting and transporting function examples include organoaluminum complexes such as tris (8-quinolinolato) aluminum, organic beryllium complexes such as bis (10-benzo [h] quinolinolato) beryllium, and beryllium of 5-hydroxyflavone Salts, aluminum salts of 5-hydroxyflavone and the like; preferably, an amine compound or an organoaluminum complex represented by the general formula (1) of the present invention.
  • the organoaluminum complex is an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand.
  • the organoaluminum complex having a substituted or unsubstituted 8-quinolinolate ligand is, for example, a compound represented by general formula (a) to general formula (c).
  • organoaluminum complexes having a substituted or unsubstituted 8-quinolinolato ligand include tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8- Quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, etc.
  • Complexes with 8-quinolinolate ligands are included.
  • organoaluminum complexes having substituted or unsubstituted 8-quinolinolato ligands include bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) ( 2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (4-methylphenolate) aluminum, bis (2- Methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato)
  • organoaluminum complexes having substituted or unsubstituted 8-quinolinolato ligands include bis (2-methyl-8-quinolinolato) aluminum- ⁇ -oxo-bis (2-methyl-8-quinolinolato) Aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum- ⁇ -oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8-quinolinolato) aluminum- ⁇ -oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum- ⁇ -oxo-bis (2-methyl-4-methoxy-) 8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum- ⁇ -oxo-bis (2-methyl-5-cyano-8-quinolinolato)
  • the compounds having an electron injection function may be used alone or in combination.
  • the electrode material of the cathode 6 is preferably a metal, alloy or conductive compound having a relatively small work function.
  • electrode materials used for the cathode include lithium salts of organic acids such as lithium, lithium-indium alloy, lithium fluoride, lithium benzoate, lithium acetate, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver Alloys, magnesium-indium alloys, indium, ruthenium, titanium, manganese, yttrium, aluminum, aluminum-lithium alloys, aluminum-calcium alloys, aluminum-magnesium alloys, graphite thin and the like. These electrode materials may be used alone or in combination.
  • Electrode materials can be disposed on the electron injecting and transporting layer by, for example, vapor deposition, sputtering, ion vapor deposition, ion plating, or cluster ion beam to form a cathode.
  • the cathode may have a single layer structure or a multilayer structure.
  • the sheet electrical resistance of the cathode is preferably several hundred ⁇ / ⁇ or less.
  • the thickness of the cathode is usually 5 to 1000 nm, preferably 10 to 500 nm, although it depends on the electrode material used.
  • At least one of the anode and the cathode is preferably transparent or translucent, and generally has a transmittance of emitted light of 70% or more.
  • the organic electroluminescent device of the present invention may contain a singlet oxygen quencher in at least one of the hole injection transport layer, the light emitting layer, and the electron injection transport layer.
  • the singlet oxygen quencher is not particularly limited, and is, for example, rubrene, nickel complex, diphenylisobenzofuran, etc., preferably rubrene.
  • the layer containing a singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer; more preferably a hole injection transport layer.
  • the hole injection / transport layer contains a singlet oxygen quencher
  • it may be uniformly contained in the hole injection / transport layer, and may be a layer adjacent to the hole injection / transport layer (for example, a light emitting layer having a light emitting function). You may make it contain in the vicinity of an electron injection transport layer).
  • the content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.05 to 30% by weight, more preferably the total amount constituting the layer to be contained (for example, hole injection transport layer). 0.1 to 20% by weight.
  • the formation method of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, and for example, vacuum deposition method, ionization deposition method, solution coating method (for example, spin coating method, casting method, dip coating) Method, bar coat method, roll coat method, Langmuir-Blodget method, inkjet method) and the like.
  • each layer (hole injection transport layer, light emitting layer, electron injection transport layer, etc.) by vacuum deposition
  • the conditions for vacuum deposition are not particularly limited, but are usually about 10 ⁇ 3 Pa or less. It is preferable to carry out under a vacuum at a boat temperature (deposition source temperature) of about 50 to 500 ° C., a substrate temperature of about ⁇ 50 to 300 ° C., and a deposition rate of about 0.001 to 50 nm / sec.
  • each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is preferably formed continuously under vacuum. It becomes possible to manufacture an organic electroluminescent element excellent in various characteristics by forming continuously.
  • each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer is formed using a plurality of compounds by vacuum deposition
  • the temperature of each boat containing the compounds is individually controlled and co-evaporated. It is preferable to do.
  • the solvent may be an organic solvent or water.
  • organic solvents include hydrocarbon solvents such as hexane, octane, decane, toluene, xylene, ethylbenzene, 1-methylnaphthalene; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; dichloromethane, chloroform, tetra Halogenated hydrocarbon solvents such as chloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene; ester solvents such as ethyl acetate, butyl a
  • a solvent is included.
  • a solvent may be used independently and may be used together.
  • a solvent for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like is used as a dispersion method. Can be used.
  • binder resins that can be used for each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl methacrylate, poly Methyl acrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polyfluorene and derivatives thereof, Polymeric compounds such as polythienylene vinylene and its derivatives are included.
  • Binder resins may be used alone or in combination.
  • the amount of the binder resin used is not particularly limited, but usually the total amount of the component and the binder resin forming each layer such as the hole injection transport layer, the light emitting layer, and the electron injection transport layer.
  • the content of the binder resin is 5 to 99.9% by weight, preferably 10 to 99% by weight (relative to the total amount of each component when a single-layer element is formed).
  • the concentration of the coating solution is not particularly limited, and may be set to a concentration range suitable for producing a film having a desired thickness by a coating method to be performed.
  • the concentration of the usual coating solution is set to 0.1 to 50% by weight, preferably 1 to 30% by weight.
  • each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, but is usually 5 nm to 5 ⁇ m.
  • the organic electroluminescent element of the present invention may have a protective layer (sealing layer) for the purpose of preventing contact with oxygen, moisture, etc., and the element may be contained in an inert substance (for example, paraffin, It can also be protected by enclosing it in liquid paraffin, silicon oil, fluorocarbon oil, zeolite-containing fluorocarbon oil).
  • an inert substance for example, paraffin, It can also be protected by enclosing it in liquid paraffin, silicon oil, fluorocarbon oil, zeolite-containing fluorocarbon oil.
  • protective layer materials include organic polymer materials (eg, fluororesin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide) ), Inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide, metal sulfide), and photo-curing resin.
  • the protective layer material may be used alone or in combination.
  • the protective layer may be a single layer or a multilayer.
  • the organic electroluminescent element of the present invention may have a metal oxide film (for example, aluminum oxide film) or a metal fluoride film as a protective film on the electrode.
  • the organic electroluminescent element of the present invention may have an interface layer (intermediate layer) on the surface of the anode.
  • the material of the interface layer can be an organic phosphorus compound, polysilane, aromatic amine derivative, phthalocyanine derivative, or the like.
  • the surface of the electrode eg, anode
  • the organic electroluminescent element of the present invention can be usually used as a DC drive type element, but can also be used as an AC drive type element.
  • the organic electroluminescence device of the present invention may be a passive drive type such as a segment type or a simple matrix drive type, and an active drive type such as a TFT (thin film transistor) type or an MIM (metal-insulator-metal) type. It may be.
  • the driving voltage is usually 2 to 30V.
  • the organic electroluminescent element of the present invention includes a panel-type light source (for example, a backlight for a clock, a liquid crystal panel, etc.), various light-emitting elements (for example, an alternative to a light-emitting element such as an LED), and various display elements [for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], various signs, various sensors, and the like.
  • a panel-type light source for example, a backlight for a clock, a liquid crystal panel, etc.
  • various light-emitting elements for example, an alternative to a light-emitting element such as an LED
  • various display elements for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], various signs, various sensors, and the like.
  • a glass substrate having an ITO transparent electrode (anode) having a thickness of 150 nm was subjected to ultrasonic cleaning using a neutral detergent, Semicoclean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and isopropyl alcohol.
  • the substrate was dried with nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 2 ⁇ 10 ⁇ 5 Pa.
  • N ′, N ′′ -bis [4- (N, N-diphenylamino) phenyl] -N ′, N ′′ -diphenyl-1,1′-biphenyl-4,4′-diamine is placed on the ITO transparent electrode.
  • N, N′-diphenyl-N, N′-di (1 ′′ -naphthyl) -1,1′-biphenyl-4,4′-diamine was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec. Evaporation was performed to form a second hole injection transport layer.
  • rubrene and the compound of Exemplified Compound A-9 were co-deposited to a thickness of 40 nm from different deposition sources at a deposition rate of 0.3 nm / sec and a deposition rate of 0.003 nm / sec, respectively, to form a light emitting layer.
  • tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm to form an electron injecting and transporting layer. Furthermore, lithium fluoride is vapor-deposited thereon to a thickness of 0.5 nm at a vapor deposition rate of 0.02 nm / sec, and finally aluminum is vapor-deposited to a thickness of 100 nm at a vapor deposition rate of 2.0 nm / sec to form a cathode. An organic electroluminescent element was produced. Vapor deposition was carried out while maintaining the vacuum state of the vapor deposition tank.
  • a DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was driven at a constant current density of 10 mA / cm 2 in a dry atmosphere at room temperature. Initially, red light emission with a luminance of 670 cd / m 2 and an emission wavelength of 624 nm was confirmed.
  • this organic electroluminescent element was continuously driven at a constant current density of an initial luminance of 5000 cd / m 2 , the time until the luminance was attenuated to 90% of the initial value was 1000 hours.
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-10 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that instead of using the compound of Illustrative Compound A-9 in forming the light emitting layer, the compound of Illustrative Compound A-14 was used. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-9 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-9 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-9 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that instead of using the compound of exemplary compound A-9 instead of using the compound of exemplary compound A-9, the light emitting layer was formed. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that instead of using the compound of exemplary compound A-9 instead of using the compound of exemplary compound A-9, the light emitting layer was formed. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that instead of using the compound of exemplary compound A-9 instead of using the compound of exemplary compound A-9, the light emitting layer was formed. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-7 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-14 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the compound of Illustrative Compound A-9 was used instead of the Compound of Illustrative Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that instead of using the compound of exemplary compound A-9 instead of using the compound of exemplary compound A-9, the light emitting layer was formed. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1). [Comparative Example 1]
  • Example 14 the organic electroluminescent device was formed according to the procedure described in Example 14 except that the following compound (DOP-1) was used instead of the compound of Exemplary Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 the organic electroluminescent device was formed by following the procedure described in Example 14 except that the following compound (DOP-2) was used in place of the compound of Exemplary Compound A-9 in forming the light emitting layer. Was made. Red light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).
  • Example 14 in forming the light emitting layer, each of the compounds of rubrene and Exemplified Compound A-9 was mixed with a thickness of 40 nm from different deposition sources at a deposition rate of 0.3 nm / sec and a deposition rate of 0.003 nm / sec. Instead of vapor deposition, rubrene and the compound of Exemplified Compound A-9 were mixed at a ratio of 99: 1, and the mixture was vapor deposited from the same vapor deposition source at a deposition rate of 0.3 nm / sec to a thickness of 40 nm. According to the operation described in Example 14, an organic electroluminescent element was produced. Red light emission was confirmed from the device. An efficiency drop of 10% was observed from the luminous efficiency of Example 14. [Comparative Example 3]
  • Example 14 in forming the light emitting layer, each of the compounds of rubrene and Exemplified Compound A-9 was mixed with a thickness of 40 nm from different deposition sources at a deposition rate of 0.3 nm / sec and a deposition rate of 0.003 nm / sec. Instead of vapor deposition, it was carried out except that the compound of rubrene and DOP-2 was mixed at a ratio of 99: 1, and the mixture was vapor deposited from the same vapor deposition source to a thickness of 40 nm at a vapor deposition rate of 0.3 nm / sec. According to the operation described in Example 14, an organic electroluminescent device was produced. Red light emission was confirmed from the device. An efficiency reduction of 25% was observed from the luminous efficiency of Comparative Example 2.
  • the decrease in the luminous efficiency in the initial stage is less in the compound represented by the general formula (1) than in the compound DOP-2, and the vapor deposition property is excellent.
  • a novel complex compound and an organic electroluminescence device using the complex compound. More specifically, a complex compound suitable for a light emitting material of an organic electroluminescent device, excellent in vapor deposition property, high in thermal stability, excellent in color purity (emission wavelength is long), and excellent in stability and durability. In addition, it has become possible to provide an organic electroluminescent device excellent in color purity.
  • Substrate 2 Anode 3: Hole injection / transport layer 3a: Hole injection / transport component 4: Light emitting layer 4a: Light emission component 5: Electron injection / transport layer 5 ′′: Electron injection / transport layer 5a: Electron injection / transport component 6: Cathode 7: Power supply

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Abstract

La présente invention porte sur un composé complexe représenté par la formule générale (1). R7 dans la formule générale (1) est représenté par la formule générale (2) et A représente un groupe alicyclique (in)saturé, un groupe hétérocyclique (in)saturé ou un groupe alkyle linéaire, ramifié ou cyclique comportant au moins un atome de fluor. Le composé complexe est approprié pour être utilisé comme matière luminescente pour des dispositifs électroluminescents organiques, etc. Le composé présente d'excellentes propriétés de dépôt en phase vapeur, une stabilité thermique élevée, une excellente pureté de couleur (de longues longueurs d'onde de luminescence) et un rendement de luminescence élevé.
PCT/JP2010/001300 2009-02-27 2010-02-25 Composé complexe et dispositif électroluminescent organique contenant le composé complexe Ceased WO2010098119A1 (fr)

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CN110114701A (zh) * 2016-12-19 2019-08-09 富士胶片株式会社 波长转换用发光性树脂组合物及其制造方法、以及波长转换部件及发光元件
CN111357128A (zh) * 2017-11-24 2020-06-30 学校法人关西学院 有机元件用材料以及使用其的有机电场发光元件

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