[go: up one dir, main page]

WO2014057659A1 - Composé, et élément électroluminescent organique produit à l'aide de ce composé - Google Patents

Composé, et élément électroluminescent organique produit à l'aide de ce composé Download PDF

Info

Publication number
WO2014057659A1
WO2014057659A1 PCT/JP2013/006000 JP2013006000W WO2014057659A1 WO 2014057659 A1 WO2014057659 A1 WO 2014057659A1 JP 2013006000 W JP2013006000 W JP 2013006000W WO 2014057659 A1 WO2014057659 A1 WO 2014057659A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
unsubstituted
substituted
organic
light emitting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2013/006000
Other languages
English (en)
Japanese (ja)
Inventor
俊裕 岩隈
真樹 沼田
亮平 橋本
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Publication of WO2014057659A1 publication Critical patent/WO2014057659A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

Definitions

  • the present invention relates to a novel compound, an organic electroluminescence element material using the compound, and an organic electroluminescence element.
  • Organic electroluminescence (EL) elements include a fluorescent type and a phosphorescent type, and an optimum element design has been studied according to each light emission mechanism. With respect to phosphorescent organic EL elements, it is known from their light emission characteristics that high-performance elements cannot be obtained by simple diversion of fluorescent element technology. The reason is generally considered as follows. First, since phosphorescence emission is emission using triplet excitons, the energy gap of the compound used in the light emitting layer must be large. This is because the value of the energy gap (hereinafter also referred to as singlet energy) of a compound usually refers to the triplet energy of the compound (in the present invention, the energy difference between the lowest excited triplet state and the ground state). This is because it is larger than the value of).
  • a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must first be used for the light emitting layer. I must. Furthermore, an electron transport layer and a hole transport layer adjacent to the light emitting layer are provided, and a compound having a triplet energy higher than that of the phosphorescent dopant material must be used for the electron transport layer and the hole transport layer.
  • a compound having a larger energy gap than the compound used for the fluorescent organic EL element is used for the phosphorescent organic EL element. The drive voltage of the entire element increases.
  • hydrocarbon compounds having high oxidation resistance and reduction resistance useful for fluorescent elements have a large energy gap due to the large spread of ⁇ electron clouds. Therefore, in a phosphorescent organic EL element, it is difficult to select such a hydrocarbon compound, and an organic compound containing a heteroatom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element.
  • the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance. That is, since light emitted from singlet excitons has a high relaxation rate that leads to light emission, the diffusion of excitons to the peripheral layers of the light-emitting layer (for example, a hole transport layer or an electron transport layer) hardly occurs and is efficient. Light emission is expected. On the other hand, light emission from triplet excitons is spin-forbidden and has a slow relaxation rate, so that excitons are likely to diffuse into the peripheral layer, and thermal energy deactivation occurs from other than specific phosphorescent compounds. End up. That is, control of the recombination region of electrons and holes is more important than the fluorescent organic EL element.
  • the triplet energy of the host material used for the light-emitting layer needs to be approximately 3.0 eV or more.
  • Patent Documents 1 to 3 disclose materials having an arylamine structure containing a carbazole skeleton.
  • An object of the present invention is to provide a novel material having electron resistance and excellent hole injection and hole transport performance to a light emitting layer, and an organic EL device having a long lifetime and high light emission efficiency.
  • Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylcarbazolyl group, a substituted or unsubstituted aryldibenzofuranyl group, a substituted or unsubstituted aryldibenzothiophenyl A group selected from the group consisting of a group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
  • R 1 to R 14 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon;
  • R 1 to R 14 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon; An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a cyano group, and a substituted or unsubstituted arylcarbazolyl group; Substituted or unsubstituted aryl dibenzofuranyl group, substituted or unsubstituted aryl dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or un
  • [In the formulas (2) to (4), Ar, R 1 to R 14 and X are the same as those in the formula (1). ] 4).
  • Ar represents an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted arylcarbazolyl group, an unsubstituted aryldibenzofuranyl group, or an unsubstituted aryldibenzo. 5.
  • the compound according to 4 which represents a group selected from the group consisting of a thiophenyl group, an unsubstituted carbazolyl group, an unsubstituted dibenzofuranyl group, and an unsubstituted dibenzothiophenyl group. 6).
  • Ar is an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted phenylcarbazolyl group, an unsubstituted phenyldibenzofuranyl group, an unsubstituted phenyldibenzothiophenyl group, an unsubstituted carbazolyl group, an unsubstituted group 6.
  • a material for an organic electroluminescence device comprising the compound according to any one of 1 to 6. 8).
  • An organic electroluminescence device comprising one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers comprises the material for an organic electroluminescence device according to 7. 9.
  • the organic thin film layer includes one or more light emitting layers, 10.
  • the organic electroluminescence device 10 wherein the triplet energy of the phosphorescent material is 1.8 eV or more and less than 2.9 eV. 12
  • the phosphorescent material contains a metal complex compound;
  • 14 14.
  • the organic electroluminescence device any one of 8 to 13, wherein the maximum value of the emission wavelength is 430 nm or more and 720 nm or less. 15.
  • the organic electroluminescence device according to claim 7, wherein the organic EL device has a hole transport zone between the light emitting layer and the anode, the hole transport zone has one or more organic thin film layers, and at least one of the organic thin film layers has 7. 15.
  • the organic electroluminescence device according to any one of 8 to 14, comprising a material. 16. 16.
  • the organic electroluminescence device according to 15, wherein the hole transport zone is adjacent to the light emitting layer.
  • the compound of the present invention is represented by the following formula (1).
  • the compound of the present invention eliminates an arylamine structure having poor electron resistance from the structure, thereby providing an organic EL device with electron resistance that can be used as a hole transport material as an electron blocking (blocking) layer and a host material in a light emitting layer. Can be granted.
  • the compound of the present invention can provide an organic EL device having a high excited triplet energy level, a long lifetime, and high luminous efficiency.
  • Ar represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylcarbazolyl group, a substituted or unsubstituted aryldibenzofuranyl group, substituted or unsubstituted It represents a group selected from the group consisting of an unsubstituted aryl dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
  • R 1 to R 14 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon;
  • R 1 to R 14 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, cyano group, substituted or unsubstituted Arylcarbazolyl group, substituted or unsubstituted aryldibenzofuranyl group, substituted or unsubstituted aryldibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, and substituted or unsubstituted It may
  • X represents an oxygen atom or a sulfur atom.
  • “unsubstituted” in “substituted or unsubstituted...” Means that a hydrogen atom is bonded, and “ring-forming carbon” means a saturated ring, an unsaturated ring, or A carbon atom constituting an aromatic ring means “ring-forming atom” means an atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • Ar represents an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted arylcarbazolyl group, an unsubstituted aryldibenzofuranyl group, an unsubstituted aryldibenzothio group.
  • a group selected from the group consisting of a phenyl group, an unsubstituted carbazolyl group, an unsubstituted dibenzofuranyl group, and an unsubstituted dibenzothiophenyl group is preferable.
  • Ar represents an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted phenylcarbazolyl group, an unsubstituted phenyldibenzofuranyl group, an unsubstituted phenyldibenzothio group.
  • a group selected from the group consisting of a phenyl group, an unsubstituted carbazolyl group, an unsubstituted dibenzofuranyl group, and an unsubstituted dibenzothiophenyl group is preferable.
  • alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n -Hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n -Hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group,
  • alkoxy group having 1 to 20 carbon atoms examples include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group and the like, and those having 3 or more carbon atoms are linear, cyclic or branched Among them, those having 1 to 6 carbon atoms are preferable.
  • haloalkyl group having 1 to 20 carbon atoms examples include groups in which one or more halogen atoms are substituted on the above alkyl group having 1 to 20 carbon atoms. Specific examples include a trifluoromethyl group and a pentafluoromethyl group. Etc. are preferred.
  • haloalkoxy group having 1 to 20 carbon atoms examples include groups in which one or more halogen atoms are substituted on the above-described alkoxy group having 1 to 20 carbon atoms. Specific examples include trifluoromethoxy groups, pentafluoroethoxy groups. Groups and the like are preferred.
  • aryl group having 6 to 30 ring carbon atoms include phenyl group, tolyl group, xylyl group, mesityl group, o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, o-terphenylyl group, m- Examples thereof include a terphenylyl group, a p-terphenylyl group, a naphthyl group, a phenanthryl group, and a triphenylene group. Of these, phenyl, m-biphenylyl and m-terphenylyl are preferred.
  • the arylcarbazolyl group is a group in which the carbazolyl group is substituted with an aryl group (for example, the above aryl group having 6 to 30 ring carbon atoms).
  • an aryl group for example, the above aryl group having 6 to 30 ring carbon atoms.
  • a phenyl carbazolyl group, a diphenyl carbazolyl group, etc. are mentioned.
  • the aryl dibenzofuranyl group is a group in which the dibenzofuranyl group is substituted with an aryl group (for example, the above aryl group having 6 to 30 ring carbon atoms). Examples thereof include a phenyl dibenzofuranyl group and a diphenyl dibenzofuranyl group.
  • the aryl dibenzothiophenyl group is a group in which a dibenzothiophenyl group is substituted with an aryl group (for example, the above aryl group having 6 to 30 ring carbon atoms).
  • a phenyl dibenzothiophenyl group, a diphenyl dibenzothiophenyl group, etc. are mentioned.
  • the alkylsilyl group is a group in which the silyl group is substituted with an alkyl group (for example, the above alkyl group having 1 to 20 carbon atoms).
  • an alkyl group for example, the above alkyl group having 1 to 20 carbon atoms.
  • a trimethylsilyl group, a triethylsilyl group, t-butyldimethylsilyl and the like can be mentioned.
  • the arylsilyl group is a group in which the silyl group is substituted with an aryl group (for example, the above aryl group having 6 to 30 ring carbon atoms).
  • an aryl group for example, the above aryl group having 6 to 30 ring carbon atoms.
  • a triphenylsilyl group etc. are mentioned.
  • the aralkylsilyl group is a group in which a silyl group is substituted with an alkyl group (for example, the above alkyl group having 1 to 20 carbon atoms) and an aryl group (for example, the above aryl group having 6 to 30 ring carbon atoms). Examples thereof include t-butyldiphenylsilyl group, diphenylmethylsilyl group, diphenylethylsilyl group and the like.
  • the alkylgermanium group is a group in which the germanium group is substituted with an alkyl group (for example, the above alkyl group having 1 to 20 carbon atoms).
  • an alkyl group for example, the above alkyl group having 1 to 20 carbon atoms.
  • a trimethyl germanium group, a triethyl germanium group, etc. are mentioned.
  • the aryl germanium group is a group in which a germanium group is substituted with an aryl group (for example, the above-mentioned aryl group having 6 to 30 ring carbon atoms).
  • an aryl group for example, the above-mentioned aryl group having 6 to 30 ring carbon atoms.
  • a triphenyl germanium group etc. are mentioned.
  • the aralkyl germanium group is a group in which a germanium group is substituted with an alkyl group (for example, the above alkyl group having 1 to 20 carbon atoms) and an aryl group (for example, the above aryl group having 6 to 30 ring carbon atoms).
  • an alkyl group for example, the above alkyl group having 1 to 20 carbon atoms
  • an aryl group for example, the above aryl group having 6 to 30 ring carbon atoms.
  • t-butyldiphenylgermanium group, diphenylmethylgermanium group, diphenylethylgermanium group and the like can be mentioned.
  • Examples of the substituted aryl group include an aryl group substituted with a carbazolyl group, an aryl group substituted with a dibenzothiophenyl group, and an aryl group substituted with a dibenzofuranyl group.
  • a carbazolylphenyl group, a dibenzothiophenylphenyl group, a dibenzofuranylphenyl group and the like are preferable.
  • Examples of the substituted carbazolyl group include a methyl carbazolyl group, a dimethyl carbazolyl group, a carbazolyl carbazolyl group, and the like.
  • Examples of the substituted dibenzofuranyl group include a cyanodibenzofuranyl group and a carbazolyl dibenzofuranyl group.
  • Examples of the substituted dibenzothiophenyl group include a cyanodibenzothiophenyl group and a carbazolyl dibenzothiophenyl group.
  • the compounds of the present invention can be synthesized by the methods described in the synthesis examples of the examples.
  • the material for an organic EL device of the present invention includes the compound of the present invention.
  • the obtained organic EL device has a long life.
  • the material for an organic EL device of the present invention is particularly suitable as a material for an organic thin film layer constituting the organic EL device, specifically as a host material and a hole transport material for a light emitting layer of the organic EL device.
  • a hole transport layer adjacent to the light emitting layer high luminous efficiency can be maintained even in a high current density region.
  • the organic EL device of the present invention has one or more organic thin film layers including a light emitting layer between an anode and a cathode. At least one of the organic thin film layers contains the material of the present invention. Thereby, the lifetime of an organic EL element can be lengthened.
  • Examples of the organic thin film layer containing the material of the present invention include, but are not limited to, a hole transport layer, a light emitting layer, an electron transport layer, a space layer, and a barrier layer.
  • the material of the present invention is preferably contained in the light emitting layer, and particularly preferably used as a host material for the light emitting layer.
  • the light emitting layer preferably contains a fluorescent light emitting material or a phosphorescent light emitting material, and particularly preferably contains a phosphorescent light emitting material.
  • the organic EL element of this invention has an organic thin film layer in the positive hole transport zone between a cathode and a light emitting layer, and at least 1 layer of this organic thin film layer contains the organic EL element material of this invention. It is preferable (hereinafter, an organic thin film layer which is in the hole transport zone and contains the organic EL device material of the present invention is referred to as an organic thin film layer A).
  • the organic thin film layer A include an electron injection layer, an electron transport layer, and a hole blocking layer.
  • the organic thin film layer A and the light emitting layer are preferably adjacent to each other.
  • the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
  • a tandem type having a plurality of light emitting units may be used, and among them, a phosphorescent type is preferable.
  • the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
  • typical element configurations of simple organic EL elements include the following element configurations.
  • Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided. A typical layer structure of the light emitting unit is shown below.
  • A Hole transport layer / light emitting layer (/ electron transport layer)
  • B Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
  • C Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
  • D Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • E Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • F Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
  • G Hole transport layer / electron barrier layer / light emitting layer (/ electron transport layer)
  • H Hole transport layer / light emitting layer / hole barrier layer (
  • Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
  • hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / Examples include a layer configuration such as an electron transport layer.
  • An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer.
  • a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer.
  • the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
  • the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
  • a known material structure to be supplied can be used.
  • FIG. 1 is a schematic view showing a layer structure of an embodiment of the organic EL device of the present invention.
  • the organic EL element 1 has a configuration in which an anode 20, a hole transport zone 30, a light emitting layer 40, an electron transport zone 50, and a cathode 60 are laminated on a substrate 10 in this order.
  • the hole transport zone 30 refers to a layer sandwiched between the anode 20 and the light emitting layer 40 and means, for example, a hole transport layer, a hole injection layer, an electron barrier layer, or the like.
  • the electron transport zone 50 refers to a layer sandwiched between the cathode 60 and the light emitting layer 40 and means, for example, an electron transport layer, an electron injection layer, a hole barrier layer, or the like.
  • the barrier layer can confine electrons and holes in the light emitting layer 40 and increase the probability of exciton generation in the light emitting layer 40. These need not be formed, but are preferably formed in one or more layers.
  • the organic thin film layer is each organic layer provided in the hole transport zone 30, each light emitting layer 40, and each organic layer provided in the electron transport zone 50.
  • at least one layer contains the organic EL element material of the present invention.
  • the content of this material with respect to one organic thin film layer containing the organic EL device material of the present invention is preferably 1 to 100% by weight.
  • a host combined with a fluorescent dopant is referred to as a fluorescent host
  • a host combined with a phosphorescent dopant is referred to as a phosphorescent host.
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the configuration other than the layer using the organic EL element material of the present invention described above is not particularly limited, and a known material or the like can be used.
  • a known material or the like can be used.
  • the structural member of an organic EL element is demonstrated easily, the material applied to the organic EL element of this invention is not limited to the following.
  • the organic EL element of the present invention is produced on a translucent substrate.
  • the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to use a material having a work function of 4.5 eV or more.
  • Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
  • the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the cathode plays a role of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer, and is preferably formed of a material having a small work function.
  • the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, you may take out light emission from the cathode side as needed.
  • An organic layer having a light emitting function includes a host material and a dopant material.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
  • the light emitting layer employs, for example, a double host (also referred to as host / cohost) that adjusts the carrier balance in the light emitting layer by combining an electron transporting host and a hole transporting host.
  • the light emitting layer preferably contains a first host material and a second host material, and the first host material is preferably the organic EL device material of the present invention.
  • you may employ adopt the double dopant from which each dopant light-emits by putting in 2 or more types of dopant materials with a high quantum yield. Specifically, a mode in which yellow emission is realized by co-evaporating a host, a red dopant, and a green dopant to make the light emitting layer common is used.
  • the above light-emitting layer is a laminate in which a plurality of light-emitting layers are stacked, so that electrons and holes are accumulated at the light-emitting layer interface, and the recombination region is concentrated at the light-emitting layer interface to improve quantum efficiency. Can do.
  • the ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.
  • the light emitting layer can be formed by a known method such as a vapor deposition method, a spin coating method, or an LB method (Langmuir Broadgett method).
  • the light emitting layer can also be formed by thinning a solution obtained by dissolving a binder such as a resin and a material compound in a solvent by a spin coating method or the like.
  • the light emitting layer is preferably a molecular deposited film.
  • the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state.
  • the thin film (molecular accumulation film) formed by the LB method can be classified by the difference in the aggregation structure and the higher-order structure, and the functional difference resulting therefrom.
  • the dopant material is selected from known fluorescent dopants exhibiting fluorescent emission or phosphorescent dopants exhibiting phosphorescent emission.
  • the fluorescent dopant is selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, fluorene derivatives, boron complexes, perylene derivatives, oxadiazole derivatives, anthracene derivatives, chrysene derivatives, and the like.
  • a fluoranthene derivative, a pyrene derivative, and a boron complex are used.
  • the phosphorescent dopant (phosphorescent material) that forms the light emitting layer is a compound that can emit light from the triplet excited state, and is not particularly limited as long as it emits light from the triplet excited state, but Ir, Pt, Os, Au, Cu
  • An organometallic complex containing at least one metal selected from the group consisting of, Re and Ru and a ligand is preferable.
  • the ligand preferably has an ortho metal bond.
  • a metal complex containing a metal atom selected from Ir, Os and Pt is preferable in that the phosphorescent quantum yield is high and the external quantum efficiency of the light-emitting element can be further improved, and an iridium complex, an osmium complex, or a platinum complex.
  • metal complexes such as orthometalated complexes (the ligand has a metal atom and an orthometal bond), more preferred are iridium complexes and platinum complexes, and particularly preferred are orthometalated iridium complexes.
  • the triplet energy of the phosphorescent material is preferably 1.8 eV or more and less than 2.9 eV.
  • the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1 to 70% by mass, more preferably 1 to 30% by mass. If the phosphorescent dopant content is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration quenching can be avoided.
  • the phosphorescent host is a compound having a function of efficiently emitting the phosphorescent dopant by efficiently confining the triplet energy of the phosphorescent dopant in the light emitting layer.
  • the organic EL device material of the present invention is suitable as a phosphorescent host.
  • the light emitting layer may contain 1 type of organic EL element material of this invention, and may contain 2 or more types of organic EL element material of this invention.
  • a compound other than the material for the organic EL device of the present invention can be appropriately selected as the phosphorescent host according to the purpose.
  • the organic EL device material of the present invention and other compounds may be used in combination as a phosphorescent host material in the same light emitting layer, and when there are a plurality of light emitting layers, the phosphorescent host of one of the light emitting layers.
  • the material for an organic EL device of the present invention may be used as a material, and a compound other than the material for an organic EL device of the present invention may be used as a phosphorescent host material for another light emitting layer.
  • the organic EL device material of the present invention can be used for organic layers other than the light emitting layer. In that case, a compound other than the organic EL device material of the present invention is used as the phosphorescent host of the light emitting layer. May be.
  • compounds other than the organic EL device material of the present invention and suitable as a phosphorescent host include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole 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 dimethylidene compounds, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene derivatives And metal complexes of heterocycl
  • the organic EL element material of the present invention is used as the first host material
  • the organic EL element material other than the organic EL element material of the present invention is used as the second host material.
  • a compound may be used.
  • the terms “first host material” and “second host material” mean that the plurality of host materials contained in the light emitting layer have different structures from each other. It is not specified by the material content. It does not specifically limit as said 2nd host material, It is a compound other than the organic EL element material of this invention, and the same thing as the above-mentioned compound as a compound suitable as a phosphorescent host is mentioned.
  • the second host material a compound having no cyano group is preferable.
  • the second host is preferably a carbazole derivative, arylamine derivative, fluorenone derivative, or aromatic tertiary amine compound.
  • the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and still more preferably 10 to 50 nm.
  • the thickness is 5 nm or more, it is easy to form a light emitting layer, and when the thickness is 50 nm or less, an increase in driving voltage can be avoided.
  • the electron transport layer is an organic layer formed between the light emitting layer and the cathode, and has a function of transporting electrons from the cathode to the light emitting layer.
  • an organic layer close to the cathode may be defined as an electron injection layer.
  • the electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.
  • an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
  • the electron transport layer of the organic EL device of the present invention particularly preferably contains at least one nitrogen-containing heterocyclic derivative represented by the following formulas (E) to (G).
  • Z 1 , Z 2 and Z 3 are each independently a nitrogen atom or a carbon atom.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted carbon An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R 1 may be the same or different from each other. Further, two adjacent R 1 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • Ar 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Alternatively, it is an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • Ar 1 or Ar 2 is a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted condensed aromatic group having 9 to 50 ring atoms. It is a heterocyclic group.
  • Ar 3 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
  • L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent ring having 9 to 50 ring atoms.
  • aryl group having 6 to 50 ring carbon atoms examples include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, chrysenyl group, pyrenyl group, biphenylyl group, terphenylyl group, tolyl group, fluoranthenyl group, fluorenyl group Etc.
  • heteroaryl groups having 5 to 50 ring atoms include pyrrolyl, furyl, thienyl, silolyl, pyridyl, quinolyl, isoquinolyl, benzofuryl, imidazolyl, pyrimidyl, carbazolyl, selenophenyl Group, oxadiazolyl group, triazolyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinoxalinyl group, acridinyl group, imidazo [1,2-a] pyridinyl group, imidazo [1,2-a] pyrimidinyl group and the like.
  • Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • Examples of the haloalkyl group having 1 to 20 carbon atoms include groups obtained by substituting one or more hydrogen atoms of the alkyl group with at least one halogen atom selected from fluorine, chlorine, iodine and bromine.
  • Examples of the alkoxy group having 1 to 20 carbon atoms include groups having the above alkyl group as an alkyl moiety.
  • Examples of the arylene group having 6 to 50 ring carbon atoms include groups obtained by removing one hydrogen atom from the aryl group.
  • Examples of the divalent condensed aromatic heterocyclic group having 9 to 50 ring atoms include groups obtained by removing one hydrogen atom from the condensed aromatic heterocyclic group described as the heteroaryl group.
  • the thickness of the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm. Moreover, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative as a component of the electron injection layer that can be provided adjacent to the electron transport layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
  • an organic layer close to the anode may be defined as a hole injection layer.
  • the hole injection layer has a function of efficiently injecting holes from the anode into the organic layer unit.
  • an aromatic amine compound for example, an aromatic amine derivative represented by the following formula (H) is preferably used.
  • Ar 1 ⁇ Ar 4 is a substituted or an aromatic hydrocarbon group or fused aromatic hydrocarbon group unsubstituted ring carbon atoms 6 to 50, a substituted or unsubstituted ring atoms of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups and aromatic heterocyclic groups or condensed aromatic heterocyclic groups are bonded.
  • L represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 50. Represents an aromatic heterocyclic group or a condensed aromatic heterocyclic group.
  • An aromatic amine represented by the following formula (J) is also preferably used for forming the hole transport layer.
  • the hole transport layer of the organic EL device of the present invention may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
  • the thickness of the hole transport layer is not particularly limited, but is preferably 10 to 200 nm.
  • a layer containing an acceptor material may be bonded to the anode side of the hole transport layer or the first hole transport layer. This is expected to reduce drive voltage and manufacturing costs.
  • the acceptor material a compound represented by the following formula (K) is preferable.
  • R 21 to R 26 may be the same as or different from each other, and each independently represents a cyano group, —CONH 2 , a carboxyl group, or —COOR 27 (R 27 is a group having 1 to 20 carbon atoms) Represents an alkyl group or a cycloalkyl group having 3 to 20 carbon atoms, provided that one or more pairs of R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 are combined together.
  • a group represented by —CO—O—CO— may be formed.
  • R 27 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.
  • n doping is a method of doping a metal such as Li or Cs into an electron transport material
  • p doping is F 4 TCNQ (2, 3, 5, 6) as a hole transport material.
  • the space layer is a fluorescent layer for the purpose of adjusting the carrier balance so that excitons generated in the phosphorescent layer are not diffused into the fluorescent layer. It is a layer provided between the layer and the phosphorescent light emitting layer.
  • the space layer can be provided between the plurality of phosphorescent light emitting layers. Since the space layer is provided between the light emitting layers, a material having both electron transport properties and hole transport properties is preferable. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.
  • the organic EL device of the present invention preferably has a barrier layer such as an electron barrier layer, a hole barrier layer, or a triplet barrier layer in a portion adjacent to the light emitting layer.
  • the electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
  • the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. is there.
  • the triplet barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the surrounding layers, and confins the triplet excitons in the light emitting layer, thereby transporting electrons other than the light emitting dopant of the triplet excitons. It has a function of suppressing energy deactivation on the molecules of the layer.
  • the phosphorescent devices When providing the triplet barrier layer, the phosphorescent devices, triplet energy E T d of the phosphorescent dopant in the light emitting layer and the triplet energy of the compound used as a triplet barrier layer and E T TB, E T d ⁇ If the energy magnitude relationship of E T TB is satisfied, the triplet exciton of the phosphorescent dopant is confined (cannot move to other molecules) and the energy deactivation path other than light emission on the dopant is interrupted. It is assumed that light can be emitted with high efficiency.
  • the organic EL element material of the present invention can be used as a triplet barrier layer having a TTF element structure described in International Publication WO2010 / 134350A1.
  • the electron mobility of the material constituting the triplet barrier layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm.
  • the electron mobility is determined by impedance spectroscopy.
  • the electron injection layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm. This facilitates the injection of electrons from the cathode into the electron transport layer, and also promotes the injection of electrons into the adjacent barrier layer and the light emitting layer, thereby enabling driving at a lower voltage.
  • an electron donating dopant and an organometallic complex is added to the interface region between the cathode and the organic thin film layer.
  • the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
  • the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
  • alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
  • alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
  • a work function of 2.9 eV or less is particularly preferable.
  • the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
  • alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
  • alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
  • the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), include such terbium fluoride (TbF 3) is, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl thiadiazole, hydroxydiaryl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.
  • the electron donating dopant and the organometallic complex it is preferable to form a layer or an island in the interface region.
  • a forming method while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and an electron is deposited in the organic material.
  • a method of dispersing at least one of a donor dopant and an organometallic complex reducing dopant is preferable.
  • the dispersion concentration is usually organic substance: electron donating dopant and / or organometallic complex in a molar ratio of 100: 1 to 1: 100, preferably 5: 1 to 1: 5.
  • At least one of the electron donating dopant and the organometallic complex is formed in a layered form
  • at least one of the electron donating dopant and the organometallic complex is formed.
  • These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
  • an electron donating dopant and an organometallic complex is formed in an island shape
  • a light emitting material or an electron injecting material which is an organic layer at the interface is formed in an island shape, and then the electron donating dopant and the organometallic complex are formed. At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
  • the ratio of at least one of the main component (light-emitting material or electron injection material), the electron-donating dopant, and the organometallic complex is, as a molar ratio, the main component: the electron-donating dopant.
  • / or organometallic complex 5: 1 to 1: 5, preferably 2: 1 to 1: 2.
  • each layer of the organic EL device of the present invention a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied. be able to.
  • the thickness of each layer is not particularly limited, but must be set to an appropriate thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the organic EL device of the present invention preferably has a maximum emission wavelength of 430 nm or more and 720 nm or less.
  • Example 1 A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode (manufactured by Geomatech) was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and further subjected to UV (Ultraviolet) ozone cleaning for 30 minutes.
  • ITO transparent electrode manufactured by Geomatech
  • the glass substrate with the transparent electrode thus cleaned is attached to the substrate holder of the vacuum evaporation apparatus, and first, on the surface of the glass substrate on which the transparent electrode line is formed, the transparent electrode is covered, Material 1 was deposited with a thickness of 20 nm to obtain a hole injection layer. Subsequently, the material 2 was vapor-deposited on this film
  • compound A as a phosphorescent host material and material 3 which is a phosphorescent material were co-evaporated at a thickness of 50 nm to obtain a phosphorescent layer.
  • concentration of Compound A in the phosphorescent light emitting layer was 80% by mass, and the concentration of Material 3 was 20% by mass.
  • the material 5 was deposited on the phosphorescent layer at a thickness of 10 nm to obtain a hole blocking layer. Furthermore, after depositing material 4 with a thickness of 10 nm to obtain an electron transport layer, LiF with a thickness of 1 nm and metal Al with a thickness of 80 nm were sequentially laminated to obtain a cathode. Note that LiF, which is an electron injecting electrode, was formed at a rate of 1 ⁇ / min.
  • Table 1 shows the evaluation results of the voltage and light emission efficiency (external quantum efficiency) at a current density of 1 mA / cm 2 and the luminance 50% lifetime (time during which the luminance is reduced to 50%) at an initial luminance of 3,000 cd / m 2 .
  • Examples 2-5 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that compounds B to E shown in Table 1 below were used in place of compound A as the phosphorescent host material. The results are shown in Table 1.
  • Comparative Examples 1 and 2 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Comparative Compounds 1 and 2 shown in Table 1 below were used as the phosphorescent host material instead of Compound A. The results are shown in Table 1.
  • Example 1 the material 2 for the hole transport layer was vapor-deposited with a thickness of 50 nm, and further, the compounds A to E shown in Table 2 below were vapor-deposited with a thickness of 10 nm on the compound A as a host material for the light-emitting layer.
  • An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the material 5 was used instead of the above. The results are shown in Table 2.
  • Example 6 an organic EL device was prepared and evaluated in the same manner as in Example 6 except that Comparative Compounds 1 and 2 shown in Table 2 below were used instead of Compound A in the hole transport layer. The results are shown in Table 2.
  • Examples 11-15 organic EL elements were produced and evaluated in the same manner as in Examples 6 to 10 except that the material 6 was used instead of the material 5 as the host material of the light emitting layer. The results are shown in Table 3.
  • Example 11 an organic EL device was prepared and evaluated in the same manner as in Example 11 except that Comparative Compounds 1 and 2 shown in Table 3 below were used instead of Compound A in the hole transport layer. The results are shown in Table 3.
  • the organic EL device using the compound of the present invention as the phosphorescent host material of the phosphorescent light emitting layer has a significantly longer life than the case of using the comparative compound, and the voltage is high. Low and high external quantum efficiency was obtained. Further, from the results of Examples 6 to 15, the organic EL device using the compound of the present invention as the hole transport layer has a significantly longer life than the case of using the comparative compound, and has a high external quantum efficiency. Efficiency was obtained.
  • the compound of the present invention can be used for organic EL devices, organic EL displays, lighting, organic semiconductors, organic solar cells, and the like.
  • the material for an organic EL device of the present invention is useful as a material for realizing an organic EL device with high efficiency and long life.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/JP2013/006000 2012-10-12 2013-10-08 Composé, et élément électroluminescent organique produit à l'aide de ce composé Ceased WO2014057659A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012227200 2012-10-12
JP2012-227200 2012-10-12

Publications (1)

Publication Number Publication Date
WO2014057659A1 true WO2014057659A1 (fr) 2014-04-17

Family

ID=50477141

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/006000 Ceased WO2014057659A1 (fr) 2012-10-12 2013-10-08 Composé, et élément électroluminescent organique produit à l'aide de ce composé

Country Status (1)

Country Link
WO (1) WO2014057659A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111116561A (zh) * 2019-12-03 2020-05-08 北京绿人科技有限责任公司 一种含稠环结构的化合物及其应用和一种有机电致发光器件
WO2022134074A1 (fr) * 2020-12-25 2022-06-30 京东方科技集团股份有限公司 Dispositif électroluminescent organique, panneau d'affichage et dispositif d'affichage et dispositif électroluminescent
JP2022166086A (ja) * 2017-02-09 2022-11-01 株式会社半導体エネルギー研究所 化合物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009148062A1 (fr) * 2008-06-05 2009-12-10 出光興産株式会社 Composé polycyclique et dispositif électroluminescent organique l'utilisant
WO2012011756A1 (fr) * 2010-07-21 2012-01-26 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositifs organiques électroluminescents les comprenant
JP2012028548A (ja) * 2010-07-23 2012-02-09 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子、これを用いた表示装置、照明装置
WO2012050371A1 (fr) * 2010-10-13 2012-04-19 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant
EP2450975A2 (fr) * 2010-11-04 2012-05-09 Cheil Industries Inc. Composé pour dispositif opto-électronique organique, diode électroluminescente organique l'incluant et affichage incluant la diode électroluminescente organique
WO2012165832A1 (fr) * 2011-05-30 2012-12-06 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique les utilisant
WO2013154325A1 (fr) * 2012-04-10 2013-10-17 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009148062A1 (fr) * 2008-06-05 2009-12-10 出光興産株式会社 Composé polycyclique et dispositif électroluminescent organique l'utilisant
WO2012011756A1 (fr) * 2010-07-21 2012-01-26 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés organiques électroluminescents et dispositifs organiques électroluminescents les comprenant
JP2012028548A (ja) * 2010-07-23 2012-02-09 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子、これを用いた表示装置、照明装置
WO2012050371A1 (fr) * 2010-10-13 2012-04-19 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant
EP2450975A2 (fr) * 2010-11-04 2012-05-09 Cheil Industries Inc. Composé pour dispositif opto-électronique organique, diode électroluminescente organique l'incluant et affichage incluant la diode électroluminescente organique
WO2012165832A1 (fr) * 2011-05-30 2012-12-06 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique les utilisant
WO2013154325A1 (fr) * 2012-04-10 2013-10-17 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022166086A (ja) * 2017-02-09 2022-11-01 株式会社半導体エネルギー研究所 化合物
US12459892B2 (en) 2017-02-09 2025-11-04 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
CN111116561A (zh) * 2019-12-03 2020-05-08 北京绿人科技有限责任公司 一种含稠环结构的化合物及其应用和一种有机电致发光器件
CN111116561B (zh) * 2019-12-03 2022-06-17 北京绿人科技有限责任公司 一种含稠环结构的化合物及其应用和一种有机电致发光器件
WO2022134074A1 (fr) * 2020-12-25 2022-06-30 京东方科技集团股份有限公司 Dispositif électroluminescent organique, panneau d'affichage et dispositif d'affichage et dispositif électroluminescent
CN114981274A (zh) * 2020-12-25 2022-08-30 京东方科技集团股份有限公司 有机电致发光器件、显示面板、显示装置和发光装置
US12356855B2 (en) 2020-12-25 2025-07-08 Boe Technology Group Co., Ltd. Organic electroluminescence device, display panel, display device, and light emitting device

Similar Documents

Publication Publication Date Title
JP6195828B2 (ja) 有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子
JP6157617B2 (ja) 有機エレクトロルミネッセンス素子用材料、これを用いた有機エレクトロルミネッセンス素子及び電子機器
JP5870045B2 (ja) ビスカルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子
JP6199752B2 (ja) 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子、並びに含窒素複素環化合物
JP5993934B2 (ja) 有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子
CN103098253B (zh) 有机电致发光元件
JP6270735B2 (ja) 芳香族アミン誘導体及び有機エレクトロルミネッセンス素子
JP6114232B2 (ja) 複素環化合物、これを用いた有機エレクトロルミネッセンス素子用材料、並びにこれを用いた有機エレクトロルミネッセンス素子及び電子機器
JP6322587B2 (ja) 有機エレクトロルミネッセンス素子
CN104471734B (zh) 有机电场发光元件
JP6182217B2 (ja) 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子および電子機器
WO2012165256A1 (fr) Elément électroluminescent organique
JP2014094935A (ja) 化合物、及びそれを用いた有機エレクトロルミネッセンス素子
WO2014051004A1 (fr) Matériau pour éléments électroluminescents organiques, et élément électroluminescent organique
WO2014054263A1 (fr) Matériau destiné à un élément organique électroluminescent, et élément organique électroluminescent produit en utilisant ledit matériau
CN106133937B (zh) 有机电场发光元件用材料以及使用其的有机电场发光元件
WO2014057659A1 (fr) Composé, et élément électroluminescent organique produit à l'aide de ce composé
KR102370068B1 (ko) 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014050093A1 (fr) Matériau destiné à un élément électroluminescent organique, et élément électroluminescent organique produit en utilisant celui-ci
JP6088323B2 (ja) 含窒素芳香族複素環誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子
JP6088324B2 (ja) 含窒素芳香族複素環誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子
JP2014196251A (ja) ヘテロアレーン誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子
JP2014196252A (ja) ヘテロアレーン誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13845991

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13845991

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP