WO2006132173A1 - 有機金属錯体及びこれを用いた有機電界発光素子 - Google Patents

有機金属錯体及びこれを用いた有機電界発光素子 Download PDF

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WO2006132173A1
WO2006132173A1 PCT/JP2006/311203 JP2006311203W WO2006132173A1 WO 2006132173 A1 WO2006132173 A1 WO 2006132173A1 JP 2006311203 W JP2006311203 W JP 2006311203W WO 2006132173 A1 WO2006132173 A1 WO 2006132173A1
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group
organic
ring
substituent
aromatic hydrocarbon
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PCT/JP2006/311203
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English (en)
French (fr)
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Toshihiro Yamamoto
Takahiro Kai
Masaki Komori
Hiroshi Miyazaki
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Nippon Steel Chemical Co., Ltd.
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Priority to JP2007520088A priority Critical patent/JP4976288B2/ja
Priority to CN2006800203071A priority patent/CN101193875B/zh
Priority to US11/921,001 priority patent/US8709614B2/en
Publication of WO2006132173A1 publication Critical patent/WO2006132173A1/ja

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    • 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
    • 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
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/221—Carbon nanotubes
    • H10K85/225—Carbon nanotubes comprising substituents
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • 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
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • 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

Definitions

  • the present invention relates to an organometallic complex and an organic electroluminescence device using the same (hereinafter referred to as an organic EL device).
  • an electroluminescent element using an organic substance has a simplest structure including a light emitting layer and a pair of counter electrodes sandwiching the layer.
  • an organic EL element when an electric field is applied between both electrodes, electrons are injected from the cathode and holes are injected from the anode. Utilizes the phenomenon of emitting light as energy when returning to the electronic band.
  • Patent Document 1 Special Table 2003-515897
  • Patent Document 2 JP 2001-313178 A
  • Patent Document 3 JP 2002-305083 A
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-352957
  • Patent Document 1 discloses an L MX complex as a phosphorescent dopant for an organic EL device.
  • Patent Document 2 discloses an organic EL device having a light emitting layer containing 0.5 to 8 wt% of a phosphorescent iridium complex.
  • CBP is exemplified as a preferred host material used for the tris (2-phenylpyridine) iridium (Ir (ppy) 3) force light emitting layer.
  • the host material does not contain a phosphorescent dopant, it is useful as a fluorescent EL element material.
  • the phosphorescent EL element has an advantage of high luminous efficiency. Therefore, compatibility with phosphorescent dopants is important for phosphorescent EL devices.
  • CBP CBP is easy to flow holes and electrons are difficult to flow, so the charge injection balance is disrupted, and excess holes flow out to the electron transport side, resulting in luminous efficiency from Ir (ppy) 3. There is a problem that it decreases.
  • Patent Document 3 is an organic EL device using phosphorescence emission, which includes an organic metal complex (1) including a metal of group 7 to 11 and [-AB-0-] ML (where A is A heterocyclic ring like a diazole ring
  • An organic EL device containing an organometallic complex (2) in a light emitting layer is disclosed.
  • the organometallic complex (1) include iridium complexes such as Ir (ppy) 3 and platinum complexes.
  • Ir (ppy) 3 iridium complexes
  • platinum complexes platinum complexes.
  • CBP CBP is easy to crystallize, so the stability of the film is poor and drive stability is a problem. Therefore, an organometallic complex (2) is proposed as a host material.
  • organometallic complexes (2) represented by the above formula is nearly infinite because L is an arbitrary substituent, the number of organometallic complexes used is not limited.
  • Examples of complexes (2) are: A is a phenyl-substituted benzodiazole ring, B is a benzene ring, M is zinc, n is 2 and j is 0, A is a thiazole ring, and B is a benzene ring. And M is beryllium, n is 2, and j is 0. That is, for any given substituent L, all of the above considerations have been made.
  • Patent Document 4 is an organic EL device using phosphorescence emission, and uses a known iridium complex such as Ir ( ⁇ y) 3 as a dopant to be present in the light emitting layer, a platinum complex, etc. It discloses that a compound having an oxadiazole group or a triazole group is used. By using a compound having an oxaziazole group or a triazole group, The light-emitting layer can be formed by a wet method, and the host material and the dopant can be sufficiently mixed to obtain high-luminance light emission with little uneven emission.
  • the compound having an oxadiazole group or a triazole group as a host material is not disclosed only in a compound containing a metal or a compound, but there is no description that teaches that it is a metal complex.
  • 3-phenyl _4- (1 naphthyl) _5_phenyl -1,2,4-triazole (TAZ) which has been introduced as a compound having a triazole group, has a characteristic that it is easy to flow electrons and difficult to flow holes.
  • the light emitting region is on the hole transport layer side. Therefore, depending on the material of the hole transport layer, the light emission efficiency from Ir (ppy) 3 may be lowered due to a compatibility problem with Ir (ppy) 3.
  • NPB 4, 4'-bis (N- (l-naphthyl) -N-phenylamino) biphenyl
  • energy from Ir (ppy) 3 such as 4,4'-bis (N, N '-(3-tolyl) amino) -3, 3'-dimethylbiphenyl (HMTPD) Power that can be considered as a means of using a material that does not cause a transition as a hole transport layer.
  • An object of the present invention is to provide an organic EL device having high efficiency and high driving stability and an organometallic complex suitable for the organic EL device in view of the above-described present situation.
  • the present invention is an organometallic complex for organic EL represented by the following general formula (I).
  • Ar may have a substituent, may have a divalent aromatic hydrocarbon group or a substituent.
  • Ar is an aromatic hydrocarbon which may have a substituent
  • a heteroaromatic group that may have a group or substituent, but Ar and Ar combine to form a ring
  • M represents a trivalent metal
  • L represents an arylate or heteroarylate coordination which may have a substituent containing a heterocyclic moiety having at least one nitrogen capable of coordinating to M as a ring atom. Indicates the quantifier.
  • L is exemplified by the ligands represented by the following general formulas (II) to (IV).
  • ring A represents an optionally substituted nitrogen-containing heterocyclic ring
  • ring B represents an optionally substituted aromatic hydrocarbon ring or aromatic heterocyclic ring
  • ring A when ring B has two or more substituents in each ring, they may be bonded to each other to form a ring
  • X represents a carbon atom or a nitrogen atom.
  • R to R represent H or an arbitrary substituent, and adjacent substituents are bonded to each other to form a ring.
  • X represents an oxygen atom or a sulfur atom.
  • R to R are each a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an
  • R to R are independently a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an a
  • Lucenyl group alkynyl group, cyano group, dialkylamino group, diarinoreamino group, diarolequinolamino group, amino group, nitro group, asinole group, alkoxycarbonyl group, carboxy group, alkoxyl group, alkylsulfonyl Group, haloalkyl group, hydroxyl group, amide group
  • an aromatic hydrocarbon group which may have a substituent or a heteroaromatic group which may have a substituent, and adjacent substituents may be bonded to each other to form a ring.
  • examples of Ar and Ar include groups represented by the following general formula (X)
  • R 1 to R 4 independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group,
  • the present invention is an organic electroluminescent device having an organic layer containing the above organic metal complex for organic EL. If the organic layer containing the organic metal complex for organic EL is a light emitting layer further containing a phosphorescent dopant, a phosphorescent organic EL device can be obtained.
  • the organometallic complex of the present invention is represented by the general formula (I).
  • L, Ar, Ar or Ar is preferably a group represented by general formula (11), (111), (IV), (IX) or (X).
  • it is preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a phenyl group that may be substituted by an alkyl group having 1 to 6 carbon atoms.
  • Ar is as described above, but may have a divalent aromatic hydrocarbon group or
  • Preferred examples of the divalent heteroaromatic group which may have a substituent include aromatic hydrocarbon groups such as phenylene, naphthylene, and pyridylene groups, and heteroaromatic groups. And a phenylene group substituted with a ren group or an alkyl group having 1 to 6 carbon atoms.
  • Ar and Ar are as described above, but as an aromatic hydrocarbon group which may have a substituent,
  • the heteroaromatic group which may have a substituent is preferably a heteroaromatic group such as a pyridyl group, a quinolyl group, a chenyl group, a carbazole group, an indolyl group, or a furyl group, and more preferably a pyridinole group. Or a quinolyl group is mentioned.
  • the substituent includes a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, a phenoxy group, and methylphenyloxy.
  • a lower alkyl group having 1 to 6 carbon atoms a lower alkoxy group having 1 to 6 carbon atoms
  • a phenoxy group a phenoxy group
  • methylphenyloxy a group having 1 to 6 carbon atoms
  • benzyloxy group, phenyl group, naphthyl group, dimethylamino group and the like is a substituent.
  • Ar, Ar, and Ar each bind to N to form a triarylamine structure.
  • This triarylamine structure is a structure possessed by a certain kind of hole-transporting organic compound, and preferable Ar, Ar, and Ar can be understood from the strong hole-transporting organic compound. And Many powerful hole transporting organic compounds are known in Patent Documents 1 to 4 and the like.
  • M represents a trivalent metal.
  • Preferable trivalent metals include anoleminium, gallium, indium and the like.
  • L is bonded to the metal M via 0 (oxygen atom), and further has a heterocycle containing a heteroatom capable of coordination with the metal M.
  • the 0 is directly bonded to the aromatic ring-constituting carbon, and a heteroatom capable of coordination bonding exists as a ring-constituting atom.
  • the 0 that binds to M and the heteroatom that coordinates to M are in close proximity.
  • the heteroatom is a force S as described above, preferably a nitrogen atom. It is also possible to have a heteroatom other than the heteroatom that coordinates with M, and in this case, these may be the same or different.
  • the two Ls may be the same or different, but the same in terms of synthesis is easy and advantageous. However, it is not directly related to the use of organic EL materials.
  • L is preferably a ligand represented by the general formulas ( ⁇ ), (III), and (IV).
  • ring A is a ring having a heteroatom capable of coordinating with M
  • ring B is a ring having a ring-constituting carbon bonded to 0.
  • Ring A and ring B may have other hetero atoms or substituents.
  • X is a force as described above, preferably C (carbon atom).
  • the group represented by the general formula (II) is known from Patent Document 3 and the like. Preferably, it is a group represented by the general formula (III), more preferably a general formula (IV).
  • a 6-membered nitrogen-containing heterocyclic ring there is a 6-membered nitrogen-containing heterocyclic ring, and this ring may be condensed with 1 or 2 5- or 6-membered aromatic hydrocarbon ring or heterocyclic ring to form a condensed ring.
  • the ring can have a substituent as described above.
  • Preferred ring B is a 6-membered aromatic hydrocarbon ring or aromatic heterocyclic ring which may have a substituent, and this ring is a 5- or 6-membered aromatic hydrocarbon ring or heterocyclic ring.
  • a fused ring may be formed by condensing force ⁇ or two. This ring may have a substituent as described above.
  • each of which may have a substituent may be a diazo group.
  • Preferred rings B include those each having a substituent, a benzene ring, a pyridine ring, a diazine ring, a triazine ring, and the like, and a ring obtained by condensing these with a benzene ring.
  • R to R are the forces S as described above, preferably hydrogen, carbon number 1
  • the organometallic complex of the present invention can be produced by a known method.
  • a metal M trialkoxide compound such as an aluminum trialkoxide reacts with a compound having both a phenol ring and a heterocycle such as 2- (2-hydroxyphenyl) benzoxazole as an intermediate.
  • the complex is reacted with a triarylamine type phenol compound such as 4-diphenylaminophenol to obtain the organometallic complex of the present invention.
  • a alkoxide compound is reacted with a compound having both a phenol ring and a heterocycle such as 2- (2-hydroxyphenyl) benzoxazole to form complex (XI) as an intermediate, and then Ar Manufactured by reacting with a compound represented by Ar N- Ar -OH
  • organometallic complex of this invention is shown below, it is not limited to these.
  • the organic EL device of the present invention has an anode and a cathode on the substrate, and an organic layer provided therebetween, and at least one of the organic layers contains the organometallic complex.
  • the organic layer containing the organometallic complex of the present invention is suitable for a light emitting layer, and particularly suitable for a light emitting layer containing a phosphorescent dopant.
  • the organometallic complex of the present invention is preferably the main component in the light emitting layer.
  • this light emitting layer uses the organometallic complex as a host material,
  • a light emitting layer doped with a phosphorescent dopant is desirable.
  • Examples of the phosphorescent dopant material include those containing an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
  • organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.
  • Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element of Ir such as the central metal, Ir (bt) 2 'a CaC complexes such as 3, complexes such as PtOEt3 is Can be mentioned. Specific examples of these complexes are shown below. The compounds are not limited to the following compounds.
  • the amount thereof ranges from 5 to 10% by weight. It is preferable that it exists in.
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.
  • FIG. 1 is a cross-sectional view schematically showing a general organic EL device.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is a hole transport layer
  • 5 is a light emitting layer
  • 6 Represents an electron transport layer
  • 7 represents a cathode.
  • the substrate, the anode, the hole transport layer, the light emitting layer, the electron transport layer, and the cathode are required layers.
  • the hole injection layer 3 and the like can be omitted, and other layers such as a hole blocking layer may be provided as necessary.
  • a cathode 7, an electron transport layer 6, a light-emitting layer 5, a hole transport layer 4, and an anode 2 can be laminated on the substrate 1 in this order.
  • One of them is highly transparent, and the organic EL device of the present invention can be provided between two substrates.
  • the present invention relates to an element having a structure in which organic EL elements are arranged in a single element or array.
  • the compound number corresponds to the number given to the chemical formula given as a preferred specific example of the organometallic complex of the present invention.
  • Compound 1 had an EI-MS (M + 1) of 708 and a melting point of 274 ° C.
  • the vacuum degree 4.0 X 10- 4 Pa conditions compound 1 and Ir (ppy) 3 and was deposited different evaporation sources force at the concentration of LK y) 3 is 7.0%
  • a thin film was formed at a thickness of 50 nm at 1.0 A / second.
  • the prepared thin film was evaluated with a fluorescence measuring apparatus.
  • the excitation wavelength is the maximum absorption wavelength of Compound 1, and the light emitted at that time was observed. Light emission from the dopant was observed rather than light emission from the host.
  • Example 2 Evaluation was performed in the same manner as in Example 2 except that a thin film was prepared by changing Compound 1 as a main component of the thin film to Alq3. Emission from the host was observed, but no emission from the dopant was observed.
  • an organic EL device with a configuration in which the hole injection layer was omitted and an electron injection layer was added was created.
  • NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
  • Compound 1 and Ir (ppy) as a light-emitting layer are shared on the hole transport layer from different evaporation sources.
  • Alq3 was formed to a thickness of 50 nm.
  • lithium fluoride (LiF) was formed as an electron injection layer to a thickness of 0.5 mm.
  • Al (A1) was formed as an electrode to a thickness of 170 nm, and an organic EL device was produced.
  • Table 1 the luminance, voltage, and luminous efficiency are values at 10 mA m 2 . Note that the maximum wavelength of the device emission spectrum was 517 nm, which proved that Ir (ppy) light emission was obtained.
  • An organic EL device was prepared in the same manner as in Example 3 except that HMTPD was used as the hole transport layer and TAZ was used as the main component of the light emitting layer.
  • An organic EL device was produced in the same manner as in Example 3 except that TAZ was used as the main component of the light emitting layer.
  • the organic EL device of the present invention can emit light with high luminance and high efficiency at a low voltage. Therefore, the organic EL element according to the present invention is applied to a flat panel display (for example, a computer A or a wall-mounted TV), an in-vehicle display element, a mobile phone display, or a light source (for example, a copier). Applications to light sources, back light sources for liquid crystal displays and instruments, display panels, beacon lights, etc. will expand.
  • a flat panel display for example, a computer A or a wall-mounted TV
  • an in-vehicle display element for example, a mobile phone display
  • a light source for example, a copier

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nanotechnology (AREA)
  • Electroluminescent Light Sources (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

  発光効率を改善し、駆動安定性を充分に確保し、かつ簡略な構成をもつ有機電界発光素子（有機ＥＬ素子）及びそれに適する有機金属錯体に関する。   この有機金属錯体は、下記一般式（Ｉ）で表される。 （式中、Ａｒ１は置換基を有してもよい芳香族炭化水素基又は複素芳香族基を示し、Ａｒ２、Ａｒ３は置換基を有してもよい芳香族炭化水素基又は複素芳香族基を示す。Ｍは３価の金属を示し、ＬはＭに対し配位結合可能な窒素を少なくとも1つ環構成原子として有する複素環部位を含むアリレート配位子を示す。）。この有機金属錯体は、燐光発光ドーパントと共に有機ＥＬ素子の発光層を構成する材料として適する。

Description

明 細 書
有機金属錯体及びこれを用レ、た有機電界発光素子
技術分野
[0001] 本発明は有機金属錯体及びこれを用いた有機電界発光素子（以下、有機 EL素子 という）に関するものである。
背景技術
[0002] —般に、有機物を用いた電界発光素子は、その最も簡単な構造としては発光層及 び該層を挟んだ一対の対向電極から構成されている。すなわち、有機 EL素子では、 両電極間に電界が印加されると、陰極から電子が注入され、陽極から正孔が注入さ れ、これらが発光層において再結合エネルギー準位が伝導帯力ら価電子帯に戻る 際にエネルギーとして光を放出する現象を利用する。
[0003] 有機 EL素子及びそれに使用される有機 EL材料は多数の文献で知られている。ま た、素子の発光効率を上げる試みとして、蛍光ではなく燐光を用いることも検討され ている。すなわち、三重項励起状態からの発光を利用すれば、従来の蛍光（一重項) を用いた素子と比べて、 3倍程度の効率向上が期待される。この目的のために燐光 発光ドーパントの開発が多数行われている。
[0004] 本発明に関連する文献としては次の特許文献がある。
特許文献 1：特表 2003-515897号公報
特許文献 2：特開 2001-313178号公報
特許文献 3：特開 2002-305083号公報
特許文献 4：特開 2002-352957号公報
[0005] 特許文献 1は、有機 EL素子用の燐光性ドーパントとしての L MX錯体が示されて
2
いる。ここで、 Lは置換べンゾォキサゾール等であり、 Mはイリジウムであり、 Xは電子 又はホールをトラップする機能を果たす配位子である錯体が好ましいものとして例示 されている。そして、発光層に用いるホスト材料として提案されているのは、カルバゾ ール化合物であり、特に 4，4'-N，N-ジカルバゾールビフエニル（CBP)が好ましいとし ている。 [0006] 特許文献 2は、燐光性のイリジウム錯体を 0. 5〜8wt%含む発光層を有する有機 E L素子を開示している。ここで、イリジウム錯体としてはトリス (2-フエニルピリジン)イリジ ゥム（Ir(ppy)3)力 発光層に用いるホスト材料としては CBPが好ましいものとして例示 されている。
[0007] ホスト材は燐光性ドーパントを含まない場合は、蛍光発光の EL素子材料として有用 であるが、上記のように燐光発光の EL素子は発光効率が高いという利点がある。そ こで、燐光発光の EL素子とする場合は、燐光性ドーパントとの適合性が重要となる。 上記 CBPを用いると、 CBPは正孔を流し易く電子を流しにくい特性上、電荷注入バラ ンスが崩れ、過剰の正孔は電子輸送側に流出し、結果として Ir(ppy)3からの発光効率 が低下するという問題点がある。
[0008] 特許文献 3は、燐光発光を利用した有機 EL素子であって、 7〜： 11族の金属を含む 有機金属錯体 (1)と [-A-B-0-] M-L (ここで、 Aはジァゾール環のような複素環であり
、 Bはベンゼン環のような環であり、 Mは 1〜3族又は 12〜： 13族の金属であり、 Lは置 換基であり、 nは Mの価数である）で表される有機金属錯体 (2)を発光層に含む有機 E L素子が開示されている。ここで、有機金属錯体 (1)としては、 Ir(ppy)3等のイリジウム 錯体ゃ白金錯体等が例示されている。そして、従来の Ir(ppy)3等のイリジウム錯体と C BPのようなホスト材料との組合せからなる発光層では、 CBPが結晶化しやすレ、ため膜 の安定性が悪ぐ駆動安定性に問題があるとして、有機金属錯体 (2)をホスト材料とし て提案している。し力 ながら、上記のような式で表される有機金属錯体 (2)の数は、 L は任意の置換基としているため無限に近いほどあるにも係らず、具体的に使用され た有機金属錯体 (2)の例は、 Aがフエニル置換ベンゾジァゾール環で、 Bがベンゼン環 で、 Mが亜鉛で、 nが 2で、 jが 0である錯体と、 Aがチアゾール環で、 Bがベンゼン環で、 Mがベリリウムで、 nが 2で、 jが 0である錯体の 2例にとどまる。すなわち、任意の置換基 Lにつレ、ての検討はなされてレ、ないに等しいとレ、える。
[0009] 特許文献 4は、燐光発光を利用した有機 EL素子であって、発光層に存在させるド 一パントとして公知の Ir (卯 y)3等のイリジウム錯体、白金錯体等を用い、ホスト材料とし てォキサジァゾール基又はトリァゾール基を有する化合物を使用することを開示して いる。ォキサジァゾール基又はトリァゾール基を有する化合物を使用することにより、 湿式法により発光層を形成でき、ホスト材料とドーパントとは十分に混合されて発光 むらの少ない高輝度の発光をえることができるとしている。し力 ながら、ホスト材料と してのォキサジァゾール基又はトリァゾール基を有する化合物は、金属を含まなレ、ィ匕 合物のみが開示されているにとどまり、金属錯体であることを教える記載はなレ、。しか も、トリァゾール基を有する化合物として紹介されている 3-フエニル _4-(1しナフチル） _5_フエニル -1，2,4 -トリアゾール (TAZ)は、電子を流しやすく正孔を流しにくい特性 上、発光領域が正孔輸送層側となる。したがって、正孔輸送層の材料によっては Ir(p py)3との相性問題により、 Ir(ppy)3からの発光効率が低下することも考えられる。例え ば、正孔輸送層として高性能、高信頼性、高寿命の点から最も良く使用されている 4, 4'-ビス (N-(l-ナフチル) -N-フエニルァミノ)ビフヱニル（NPB)は、 Ir(ppy)3との相性が 悪ぐ Ir(ppy)3から NPBにエネルギー遷移が起き、発光効率が低下するという問題が ある。
[0010] 上記の解決手段として、 4,4'-ビス (N,N'-(3-トルィル)ァミノ) -3、 3'-ジメチルビフエ二 ル（HMTPD)のような Ir(ppy)3からエネルギー遷移が起こらない材料を正孔輸送層と して用いる手段が考えられる力 発光効率等の点で優れたものとはいえない。
発明の開示
発明が解決しょうとする課題
[0011] 有機 EL素子をフラットパネル ·ディスプレイ等の表示素子に応用するためには、素 子の発光効率を改善すると同時に駆動時の安定性を十分に確保する必要がある。 本発明は、上記現状に鑑み、高効率かつ高い駆動安定性を有した有機 EL素子及 びそれに適する有機金属錯体を提供することを目的とする。
課題を解決するための手段
[0012] 本発明者らは、鋭意検討した結果、発光層の正孔及び電子のバランスを適正化す ることで、上記課題を解決することができることを見出し、本発明を完成するに至った 。すなわち、正孔輸送性の高いトリフヱニルァミン骨格を金属錯体に導入することによ り、錯体自身の正孔輸送性を向上することができ、その結果、電子と正孔のバランス が適正化され、より広い発光領域を有することが可能となり、発光効率の向上が図れ ることを見出し、本発明に至ったものである。 [0013] 本発明は、下記一般式 (I)で表される有機 EL用有機金属錯体である。
Ar,
/
LpiVi—— O—— Ar ~~
\
( I )
(式中、 Arは置換基を有してもよい 2価の芳香族炭化水素基又は置換基を有しても
1
よい 2価の複素芳香族基を示す。 Ar、 Arは置換基を有してもよい芳香族炭化水素
2 3
基又は置換基を有してもよい複素芳香族基を示すが、 Arと Arが結合して環を形成
2 3
することはない。 Mは 3価の金属を示し、 Lは Mに対し配位結合可能な窒素を少なくと も 1つ環構成原子として有する複素環部位を含む置換基を有してもよいァリレート又 はへテロァリレート配位子を示す。）
[0014] 一般式 (I)において、 Lとしては下記一般式 (II)〜（IV)で表される配位子が例示さ れる。
Figure imgf000005_0001
( I I )
(式中、環 Aは置換基を有していてもよい含窒素複素環を示し、環 Bは置換基を有し ていてもよい芳香族炭化水素環又は芳香族複素環を示し、環 A及び環 Bが各々の環 において置換基を 2以上有する場合は相互に結合して環を構成してもよい。 Xは炭 素原子又は窒素原子を示す。 )
[0016]
R6 R7
( III)
(式中、 R〜Rは H又は任意の置換基を示し、隣り合う置換基は相互に結合して環を
1 8
構成してもよい。 Xは酸素原子又は硫黄原子を示す。 )
Figure imgf000006_0001
( I V)
(式中、 R〜Rは、各々に、水素原子、ハロゲン原子、アルキル基、ァラルキル基、ァ
1 8
ルケニル基、アルキニル基、シァノ基、ジァノレキルアミノ基、ジァリールアミノ基、ジァ ラルキノレアミノ基、アミノ基、ニトロ基、アシノレ基、アルコキシカルボニル基、カルボキ シル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基 、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複素 芳香族基を示す。 )
一般式 (I)において、 Arとしては下記一般式 (IX)で表される基が例示される。
Figure imgf000007_0001
( IX)
(式中、 R〜R は独立に、水素原子、ハロゲン原子、アルキル基、ァラルキル基、ァ
9 12
ルケニル基、アルキニル基、シァノ基、ジアルキルアミノ基、ジァリーノレアミノ基、ジァ ラノレキノレアミノ基、アミノ基、ニトロ基、アシノレ基、アルコキシカルボニル基、カルボキ シル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基
、置換基を有してもよい芳香族炭化水素基又は置換基を有してもよい複素芳香族基 を示し、隣り合う置換基は相互に結合して環を構成してもよい。 )
一般式 (I)において、 Ar、 Arとしては、下記一般式 (X)で表される基が例示される
Figure imgf000007_0002
(式中、 R 〜R は、独立に、水素原子、ハロゲン原子、アルキル基、ァラルキル基、
13 17
アルケニル基、アルキニル基、シァノ基、ジアルキルアミノ基、ジァリーノレアミノ基、ジ ァラルキルアミノ基、アミノ基、ニトロ基、ァシル基、アルコキシカルボニル基、カルボ キシノレ基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド 基、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複 素芳香族基を示し、隣り合う置換基は相互に結合して環を構成してもよい。 )
[0020] また、本発明は、上記の有機 EL用有機金属錯体を含む有機層を有する有機電界 発光素子である。この有機 EL用有機金属錯体を含む有機層が、更に燐光発光ドー パントを含有する発光層であると燐光発光性の有機 EL素子が得られる。
[0021] 以下、本発明を更に説明する。
[0022] 本発明の有機金属錯体は前記一般式 (I)で表わされる。一般式 (I)において、 L、 A r、Ar又は Arとしては、一般式 (11)、（111)、（IV)、（IX)又は（X)で表される基が好ま
1 2 3
しいものとして挙げられる。また、一般式（ΙΠ)、 (IV)において、 R〜Rは前記のとおり
1 8
であるが、好ましくは水素原子、炭素数 1〜6のアルキル基、炭素数 1〜6のアルコキ シル基、炭素数 1〜6のアルキル基が置換してもよいフエニル基である。
[0023] Arは前記のとおりであるが、置換基を有してもよい 2価の芳香族炭化水素基又は
1
置換基を有してもよい 2価の複素芳香族基としてはフエ二レン基、ナフチレン基、ピリ ジレン基等の芳香族炭化水素基又は複素芳香族基が好ましく例示され、より好ましく はフエ二レン基又は炭素数 1〜6のアルキル基が置換したフエ二レン基が挙げられる [0024] Ar、 Arは前記のとおりであるが、置換基を有してもよい芳香族炭化水素基として
2 3
はフヱニル基、ナフチル基、ァセナフチル基、アントリル基等の芳香族炭化水素基が 好ましく例示され、より好ましくはフヱニル基、ナフチル基が挙げられる。置換基を有 してもよい複素芳香族基としては、ピリジル基、キノリル基、チェニル基、カルバゾー ル基、インドリル基、フリル基等の複素芳香族基が好ましく例示され、より好ましくはピ リジノレ基又はキノリル基が挙げられる。芳香族炭化水素基及び複素芳香族基が置換 基を有する場合、置換基としては炭素数 1〜6の低級アルキル基、炭素数 1〜6の低 級アルコキシ基、フエノキシ基、メチルフエニルォキシ基、ベンジルォキシ基、フエ二 ル基、ナフチル基、ジメチルァミノ基等が挙げられる。
[0025] なお、 Ar、 Ar、 Arは、それぞれが Nと結合してトリアリールァミン構造を形成する
1 2 3
。このトリアリールァミン構造は、ある種の正孔輸送性有機化合物が有する構造であり 、力かる正孔輸送性有機化合物からも好ましい Ar、 Ar、 Arが理解できる。そして、 力かる正孔輸送性有機化合物は、特許文献 1〜4等において多数知られている。
[0026] Mは 3価の金属を表す。好ましい 3価の金属としては、ァノレミニゥム、ガリウム、イン ジゥム等が挙げられる。
[0027] 一般式 (I)において、 Lは金属 Mと 0 (酸素原子）を介して結合しているが、更に金属 Mと配位結合可能なヘテロ原子を含む複素環を有する。そして、上記 0は芳香族環 構成炭素に直接結合しており、配位結合可能なヘテロ原子は環構成原子として存在 する。そして、 Mと結合する 0と、 Mと配位結合するへテロ原子は、近接位に存在する ことになる。ここで、ヘテロ原子は上記のとおりである力 S、好ましくは窒素原子である。 なお、 Mと配位結合するへテロ原子以外のへテロ原子を有することもでき、この場合こ れらは同一であっても、異なってもよい。また、 2つの Lは同一であっても、異なってい ても差し支えなレ、が、合成の点では同一であるものが容易で有利である。しかし、有 機 EL材料の用途とは直接の関係はない。
[0028] Lとしては、一般式 (Π)、 (III)、 (IV)で表される配位子が好ましレ、ものとして挙げられ る。
[0029] 一般式 (II)において、環 Aは Mと配位結合可能なヘテロ原子を有する環であり、環 Bは 0と結合する環構成炭素を有する環である。環 A及び環 Bは、その他のヘテロ原 子を有してもよぐ置換基を有してもよい。 Xは上記のとおりである力 好ましくは C (炭 素原子）である。
[0030] 一般式 (II)で表される基は、特許文献 3等で知られているものがある。好ましくは、 一般式 (III)、より好ましくは一般式 (IV)で表される基である。
[0031] 一般式 (II)において、好ましい環 Aとしては、置換基を有していてもよい 5員環又は
6員環の含窒素複素環があり、この環に 5又は 6員環の芳香族炭化水素環又は複素 環が 1又は 2個縮合して縮合環を形成していてもよい。そして、この環は上記のような 置換基を有しうる。また、好ましい環 Bとしては、置換基を有してもよい 6員環の芳香 族炭化水素環又は芳香族複素環であり、この環に 5又は 6員環の芳香族炭化水素環 又は複素環力 ^又は 2個縮合して縮合環を形成していてもよい。そして、この環は上 記のような置換基を有しうる。
[0032] 具体的には、好ましい環 Aとしては、それぞれ置換基を有していてもよレ、、ジァゾ一 ル環、チアゾール環、ォキサゾール環、チアジアゾール環、ォキサジァゾール環、トリ ァゾール環、ピリジン環、ジァジン環、トリアジン環等やこれらとベンゼン環が縮合した ベンゾジァゾール環、ベンゾチアゾール環、ベンゾチアジアゾール環、ベンゾォキサ ジァゾール環、ベンゾトリアゾール環、キノリン環、イソキノリン環、ベンゾジァジン環、 ベンゾトリアジン環等がある。好ましい環 Bとしては、それぞれ置換基を有していてもよ レ、、ベンゼン環、ピリジン環、ジァジン環、トリアジン環等やこれらとベンゼン環が縮合 した環がある。
[0033] 一般式 (IV)において、 R〜Rは上記のとおりである力 S、好ましくは水素、炭素数 1
1 8
〜6のアルキル又は炭素数 1〜6のアルキルが置換してもよいフエニル基である。
[0034] 本発明の有機金属錯体は公知の方法で製造することができる。例えば、アルミユウ ムトリアルコキシドのような金属 Mのトリアルコキシド化合物と、 2-(2-ヒドロキシフエニル )ベンゾォキサゾールのようなフエノール環とヘテロ環の両者を有する化合物を反応さ せて中間体としての錯体を得て、この錯体に 4-ジフヱニルァミノフエノールのようなトリ ァリールァミン型のフエノール化合物と反応させることにより、本発明の有機金属錯体 を得る。
[0035] これを化学式で表せば次のようになる。まず、 M (OR)で表わされる金属 Mのトリア
3
ルコキシド化合物と、 2-(2-ヒドロキシフエニル)ベンゾォキサゾールのようなフエノール 環とヘテロ環の両者を有する化合物を反応させて中間体としての錯体 (XI)を一旦形 成させ、その後 Ar Ar N- Ar -OHで表される化合物と反応させることによって製造す
2 3 1
ること力 sできる。
Figure imgf000011_0001
本発明の有機金属錯体の好ましい具体例を以下に示すが、これらに限定するもの ではない。
Figure imgf000012_0001
次に、本発明の有機金属錯体を用いた、有機 EL素子について説明する。本発明 の有機 EL素子は、基板上に陽極及び陰極と、これらの間に設けられた有機層を有し 、該有機層の少なくとも 1層が該有機金属錯体を含有する。本発明の有機金属錯体 を含む有機層は、発光層に適し、特に燐光発光ドーパントを含む発光層に適する。 発光層に使用する場合、本発明の有機金属錯体は、発光層における主成分である ことが好まし 特に、この発光層は該有機金属錯体をホスト材料とし、該ホスト材料 に対して燐光発光ドーパントをドープしてなる発光層であることが望ましい。
[0039] 燐光発光ドーパント材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、 オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金 属錯体を含有するものが例示される。かかる有機金属錯体は、前記特許文献等で公 知であり、これらが選択されて使用可能である。
[0040] 好ましい燐光発光ドーパントとしては、 Ir等の貴金属元素を中心金属として有する Ir (ppy)3等の錯体類、 Ir(bt)2 'aCaC3等の錯体類、 PtOEt3等の錯体類が挙げられる。こ れらの錯体類の具体例を以下に示す力 下記の化合物に限定されない。
Figure imgf000013_0001
[0042]
Figure imgf000014_0001
[0044] 燐光発光ドーパントが発光層中に含有される場合、その量は 5〜 10重量％の範囲 にあることが好ましい。
図面の簡単な説明
[0045] [図 1]有機 EL素子の一例を示した模式断面図。
符号の説明
[0046] 1 基板、 2 陽極、 3 正孔注入層、 4 正孔輸送層、 5 発光層、 6 電子輸送層、
7 陰極
発明を実施するための最良の形態
[0047] 次に、本発明の有機 EL素子の構造について、図面を参照しながら説明する力 本 発明の有機 EL素子の構造は何ら図示のものに限定されるものではない。
[0048] 図 1は一般的な有機 EL素子を模式的に示す断面図であり、 1は基板、 2は陽極、 3 は正孔注入層、 4は正孔輸送層、 5は発光層、 6は電子輸送層、 7は陰極を各々表わ す。有機 EL素子は、基板、陽極、正孔輸送層、発光層、電子輸送層及び陰極を必 須の層とすることが望ましい。この場合、正孔注入層 3等は省略可能であり、また必要 により正孔阻止層等の他の層を設けてもよい。
[0049] なお、図 1とは逆の構造、すなわち、基板 1上に陰極 7、電子輸送層 6、発光層 5、 正孔輸送層 4、陽極 2の順に積層することも可能であり、少なくとも一方が透明性の高 レ、 2枚の基板の間に本発明の有機 EL素子を設けることも可能である。
[0050] 本発明は、有機 EL素子が、単一の素子、アレイ状に配置された構造からなる素子
、陽極と陰極が X—Yマトリックス状に配置された構造のいずれにおいても適用するこ とがでさる。
実施例
[0051] 以下、本発明を実施例によって更に詳しく説明するが、これらの実施例に限定され るものではない。なお、化合物番号は本発明の有機金属錯体の好ましい具体例とし て挙げた化学式に付した番号に対応する。
[0052] 実施例 1
脱気窒素置換した 100ml三口フラスコにアルミニウムトリイソプロボキシド 3.0g、 2-(2- ヒドロキシフエ二ノレ)ベンゾォキサゾール 6.2gを加え、これに無水トルエン 50mlを加え て溶解させた。その後 60。Cまで加熱し、 30分攪拌した。これに 4-ジフエニルァミノフエ ノール 3.8gの溶けた無水トルエン 50mlをゆっくり滴下して、そのまま 60°Cにて 3時間攪 拌した。室温まで冷却した後、生じた白色沈殿を濾取した後、ろ液を 1/2量まで濃縮 した。 1/2量まで濃縮したろ液中に析出した結晶をろ別し、トルエンで洗浄した。これ を、減圧乾燥して黄色粉末 (化合物 l ; M=Al) 9.0gを得た。この一部を昇華精製し、素 子作成に用いた。
化合物 1の EI— MS (M+ 1)は 708、融点は 274°Cであった。
[0053] 実施例 2
ガラス基板上に真空蒸着法にて、真空度 4.0 X 10— 4 Paの条件にて化合物 1と Ir(ppy )3とを異なる蒸着源力 蒸着し、 lK y)3の濃度が 7.0 %である薄膜を 1.0A/秒にて 50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物 1の極大吸収波 長であり、そのときに出てくる光を観察した。ホストからの発光ではなぐドーパントから の発光が観測された。
[0054] 比較例 1
薄膜主成分である化合物 1を Alq3に変えて薄膜を作成した以外は、実施例 2と同様 に評価した。ホストからの発光が観測され、ドーパントからの発光は観測されなかった
[0055] 実施例 3
図 1において、正孔注入層を省略し、電子注入層を追加した構成の有機 EL素子を 作成した。膜厚 150議の ITOからなる陽極が形成されたガラス基板上に、各薄膜を真 空蒸着法にて、真空度 4.0 X 10— 4 Paで積層させた。まず、 ITO上に正孔輸送層として NPBを 60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物 1と Ir(ppy)とを異なる蒸着源から、共
3
蒸着し、 25議の厚さに形成した。 Ir(ppy)の濃度は 7.0 %であった。次に、電子輸送
3
層として Alq3を 50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフ ッ化リチウム（LiF)を 0.5匪の厚さに形成した。最後に、電子注入層上に、電極として アルミニウム (A1)を 170nmの厚さに形成し、有機 EL素子を作成した。 [0056] 得られた有機 EL素子に外部電源を接続し直流電圧を印加したところ、表 1のような 発光特性を有することが確認された。表 1において、輝度、電圧及び発光効率は、 10 mAん m2での値を示す。なお、素子発光スペクトルの極大波長は 517 nmであり、 Ir(ppy )力もの発光が得られていることがわ力つた。
3
[0057] 比較例 2
正孔輸送層として HMTPDを、発光層の主成分として TAZを用いた以外は実施例 3 と同様にして有機 EL素子を作成した。
[0058] 比較例 3
発光層の主成分として、 TAZを用いた以外は実施例 3と同様にして有機 EL素子を 作成した。
[0059] [表 1]
Figure imgf000017_0001
産業上の利用の可能性
[0060] 本発明の有機 EL素子は、低電圧において高輝度 ·高効率で発光させることが可能 となる。従って、本発明による有機 EL素子をフラットパネル ·ディスプレイ (例えば、〇 Aコンピュータ用や壁掛けテレビ）、車載表示素子、携帯電話表示や面発光体として の特徴を生力した光源 (例えば、複写機の光源、液晶ディスプレイや計器類のバック ライト光源）、表示板、標識灯等への応用が広がる。

Claims

請求の範囲
[1] 下記一般式 (I)で表される有機 EL用有機金属錯体。
Figure imgf000018_0001
( I )
(式中、 Arは置換基を有してもよい 2価の芳香族炭化水素基又は置換基を有しても
1
よい 2価の複素芳香族基を示す。 Ar 、 Arは置換基を有してもよい芳香族炭化水素
2 3
基又は置換基を有してもよい複素芳香族基を示すが、 Arと Arが結合して環を形成
2 3
することはない。 Mは 3価の金属を示し、 Lは Mに対し配位結合可能な窒素を少なくと も 1つ環構成原子として有する複素環部位を含む置換基を有してもよいァリレート又 はへテロァリレート配位子を示す。）
[2] Lが下記一般式 (Π)で表される配位子である請求項 1記載の有機 EL用有機金属錯 体。
Figure imgf000018_0002
( I I )
(式中、環 Aは置換基を有していてもよい含窒素複素環を示し、環 Bは置換基を有し ていてもよい芳香族炭化水素環又は芳香族複素環を示し、環 A及び環 Bが各々の環 において置換基を 2以上有する場合は相互に結合して環を構成してもよい。 Xは炭 素原子又は窒素原子を示す。 )
[3] Lが下記一般式 (III)で表される配位子である請求項 1記載の有機 EL用有機金属
Figure imgf000019_0001
(III)
(式中、 R〜Rは H又は任意の置換基を示し、隣り合う置換基は相互に結合して環を
1 8
構成してもよい。 Xは酸素原子又は硫黄原子を示す。 )
Lが下記一般式 (IV)で表される配位子である請求項 1記載の有機 EL用有機金属 錯体。
Figure imgf000019_0002
(IV) (式中、 R〜Rは、各々に、水素原子、ハロゲン原子、アルキル基、ァラルキル基、ァ
1 8
ルケニル基、アルキニル基、シァノ基、ジアルキルアミノ基、ジァリーノレアミノ基、ジァ ラノレキノレアミノ基、アミノ基、ニトロ基、アシノレ基、アルコキシカルボニル基、カルボキ シル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基 、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複素 芳香族基を示す。 )
Arが下記一般式 (IX)で表される請求項 1〜4のいずれかに記載の有機 EL用有機
1
金属錯体。
Figure imgf000020_0001
( I X)
(式中、 R〜R は独立に、水素原子、ハロゲン原子、アルキル基、ァラルキル基、ァ
9 12
ルケニル基、アルキニル基、シァノ基、ジアルキルアミノ基、ジァリーノレアミノ基、ジァ ラノレキノレアミノ基、アミノ基、ニトロ基、アシノレ基、アルコキシカルボニル基、カルボキ シル基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド基 、置換基を有してもよい芳香族炭化水素基又は置換基を有してもよい複素芳香族基 を示し、隣り合う置換基は相互に結合して環を構成してもよい。 )
Ar、 Arが下記一般式 (X)で表されるァリール基である請求項 1〜5のいずれかに
2 3
記載の有機 EL用有機金属錯体。
Figure imgf000020_0002
(式中、 R 〜R は、独立に、水素原子、ハロゲン原子、アルキル基、ァラルキル基、
13 17
アルケニル基、アルキニル基、シァノ基、ジアルキルアミノ基、ジァリーノレアミノ基、ジ ァラルキルアミノ基、アミノ基、ニトロ基、ァシル基、アルコキシカルボニル基、カルボ キシノレ基、アルコキシル基、アルキルスルホニル基、ハロアルキル基、水酸基、アミド 基、置換基を有していてもよい芳香族炭化水素基又は置換基を有していてもよい複 素芳香族基を示し、隣り合う置換基は相互に結合して環を構成してもよい。 )
[7] 請求項:!〜 6のいずれかに記載の有機 EL用有機金属錯体を含む有機層を有する 有機電界発光素子。
[8] 有機 EL用有機金属錯体を含む有機層が、更に燐光発光ドーパントを含有する発 光層である請求項 7記載の有機電界発光素子。
PCT/JP2006/311203 2005-06-07 2006-06-05 有機金属錯体及びこれを用いた有機電界発光素子 WO2006132173A1 (ja)

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US20090026923A1 (en) 2009-01-29
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