WO2008056746A1 - Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique - Google Patents

Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique Download PDF

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WO2008056746A1
WO2008056746A1 PCT/JP2007/071728 JP2007071728W WO2008056746A1 WO 2008056746 A1 WO2008056746 A1 WO 2008056746A1 JP 2007071728 W JP2007071728 W JP 2007071728W WO 2008056746 A1 WO2008056746 A1 WO 2008056746A1
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organic
compound
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light emitting
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PCT/JP2007/071728
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French (fr)
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Takahiro Kai
Masaki Komori
Toshihiro Yamamoto
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Nippon Steel Chemical Co., Ltd.
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Priority to CN2007800323985A priority Critical patent/CN101511834B/zh
Priority to JP2008543124A priority patent/JP4388590B2/ja
Priority to US12/439,787 priority patent/US8062769B2/en
Priority to EP07831459.8A priority patent/EP2080762B1/en
Publication of WO2008056746A1 publication Critical patent/WO2008056746A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—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
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    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to a novel compound for organic electroluminescence device and organic electroluminescence device (hereinafter referred to as organic EL device). Specifically, a phosphorescent dopant and a host compound having a specific structure are used in combination. Therefore, the present invention relates to an organic EL element exhibiting a high luminance rate.
  • an organic EL element has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. That is, in an organic EL device, when an electric field is applied between both electrodes, electrons are injected from the cathode and holes are injected from the anode, and these recombination energy levels in the light emitting layer change from the conduction band to the valence band. Utilizing the phenomenon of emitting light as energy when returning to.
  • the type of electrode is optimized for the purpose of improving the efficiency of carrier injection from the electrode, and consists of a hole transport layer made of aromatic diamine and an 8-hydroxyquinoline aluminum complex (hereinafter referred to as Alq3).
  • Alq3 8-hydroxyquinoline aluminum complex
  • Patent Document 1 Japanese Translation of Special Publication 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 5 Japanese Patent Laid-Open No. 11-162650
  • Patent Document 6 Japanese Patent Laid-Open No. 11-176578
  • CBP As a host material used in the light emitting layer of an organic EL device, CBP, a rubazole compound introduced in Patent Document 2 is proposed.
  • CBP is used as the host material for Ir (ppy) 3
  • a green phosphorescent light emitting material CBP has a characteristic that it is easy to flow holes and it is difficult to flow electrons, and the charge injection balance is lost, and excess holes flow out to the electron transport layer side.
  • the luminous efficiency from Ir (ppy) 3 decreases.
  • a hole blocking layer is provided between the light emitting layer and the electron transport layer.
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrine phosphorus
  • BAlq and! / p-phenylphenolate-bis (2-methyl -8-Quinolinolato-N1, 08) Aluminum
  • 3-phenyl _4- (1'-naphthyl) -5-phenyl-1,2,4-triazole (hereinafter referred to as TAZ) introduced in Patent Document 4 is also a host material for phosphorescent organic EL devices.
  • the light emitting region is on the side of the hole transport layer because of the characteristic that electrons are easy to flow and holes are difficult to flow. Shi Therefore, depending on the material of the hole transport layer, the light emission efficiency from Ir (ppy) 3 may decrease due to a compatibility problem with Ir (ppy) 3.
  • NPB 4,4'_bis (N- (l-naphthyl) -N-phenylamino) biphenyl
  • Indolo strength rubazole compounds disclosed in Patent Documents 5 and 6 are recommended to be used as hole transport materials, and are used as force phosphorescent host materials for which stability of the compounds is also considered. Does not teach the use of. Also, the structure of the compound is different from the compound of the present invention.
  • An object of the present invention is to provide a practically useful organic EL device having high efficiency and high driving stability, and a compound suitable therefor, in view of the above-described present situation.
  • the present invention provides a practically useful organic EL device having high efficiency, high resistance and driving stability by using a compound having a specific indolo strength rubazole skeleton.
  • the compound for organic electroluminescence device of the present invention is represented by the following general formula (1).
  • ring A represents a heterocyclic ring represented by the formula (la) fused with an adjacent ring at an arbitrary position, X represents N or CH, and at least one of X is a nitrogen atom.
  • Ar to Ar are independent
  • R is hydrogen or a monovalent substituent
  • the compound for organic electroluminescence device represented by the general formula (1) includes a compound represented by the following general formula (2) or (3).
  • the present invention is an organic electroluminescent device having an organic layer containing the above compound for organic electroluminescent devices.
  • an organic electroluminescent device having a light emitting layer between an anode and a cathode laminated on a substrate, wherein the light emitting layer comprises a phosphorescent dopant and the above general formulas (1), (2)
  • an organic electroluminescence device comprising the compound for organic electroluminescence device represented by (3) as a host material.
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.
  • the compound for an organic EL device of the present invention is represented by the general formula (1).
  • the compound represented by the general formula (1) has an indole strength rubazole skeleton in which a strength rubazole ring and an indole ring are condensed.
  • a ring containing three X (referred to as an X-containing ring) is bonded to the base of a force rubazole ring, and R or Ar to Ar is bonded to each ring.
  • the indole ring is ring ⁇ and Ben
  • ring A represents a heterocycle represented by the formula (la) that is condensed with an adjacent ring.
  • the heterocyclic ring represented by the formula (la) can be condensed at any position of the adjacent force rubazole ring. Specifically, it can be condensed at the 2,3-position, 3,4-position or 4,5-position of the force rubazole ring.
  • X represents CH or N, and at least one X is a nitrogen atom.
  • X is a nitrogen atom.
  • 1, 2 or 3 Xs are nitrogen atoms.
  • Ar to Ar are a substituted or unsubstituted aromatic hydrocarbon group or a condensed ring that is not a condensed ring structure.
  • a substituted or unsubstituted aromatic heterocyclic group having no structure is shown.
  • Preferred unsubstituted aromatic hydrocarbon groups include phenyl groups, biphenyl groups, terphenyl groups, tetraphenyl groups and the like.
  • Preferred unsubstituted aromatic heterocyclic groups include pyridyl groups and pyrimidides. Group, triazyl group, imidazolyl group, chenyl group and the like.
  • the substituent is a c to c alkyl group, a c to c alkoxy group, a phenoxy group, an alkyl group.
  • Examples include a ruthio group, a substituted amino group, and a acetyl group. Moreover, C5-C18 aromatic hydrocarbon group, C3-C17 aromatic heterocyclic group, etc. are mentioned.
  • Ar or Ar may be condensed with an X-containing ring to form a condensed ring.
  • X in the ⁇ -position with respect to the carbon bonded to the ⁇ of the force rubazole ring is nitrogen It is preferable that in the case of a pyrimidine ring, it is preferable that two Xs at the 0-position are nitrogen.
  • R represents hydrogen or a monovalent substituent.
  • R is independently hydrogen or an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a cyano group, a dialkylamino group, a diarylamino group, a dialalkylamino group, an amino group, a nitro group, an acyl group, an alkoxycarbonyl group, It is a norevoxyl group, an alkoxyl group, an alkylsulfonyl group, a haloalkyl group, a hydroxyl group, an amide group, a substituted or unsubstituted aromatic hydrocarbon group or an aromatic heterocyclic group.
  • Preferred monovalent substituents include C to C alkyl groups, C to C alkoxy groups, and phenols.
  • Examples include a xyl group, an alkylthio group, a substituted amino group, and a acetyl group. Furthermore, a substituted or unsubstituted C5-C18 aromatic hydrocarbon group or C3-C17 aromatic heterocyclic group is preferable.
  • preferred compounds include the compounds represented by the general formulas (2) and (3). And X, Ar to Ar in the general formulas (2) and (3)
  • the compound for an organic EL device of the present invention can be easily produced by a known method.
  • the compound represented by the general formula (2) can be produced by the following reaction formula with reference to the synthesis example shown in Synlett, 2005, No. 1, p42-48.
  • the general formula (3) can be produced by the following reaction formula with reference to the synthesis example shown in Archiv der Pharmazie (Weinheim, Germany), 1987, 320 (3), p280-2.
  • L has the same meaning as Ar to Ar.
  • the compound for an organic electroluminescence device of the present invention provides an excellent organic electroluminescence device by being contained in the organic layer of the organic EL device.
  • it may be contained in at least one organic layer selected from a light emitting layer, a hole transport layer, an electron transport layer and a hole blocking element layer. More preferably, it may be contained as a host material of a light emitting layer containing a phosphorescent dopant.
  • the organic electroluminescent device of the present invention is preferably an organic electroluminescent device having a light emitting layer between an anode and a cathode laminated on a substrate, wherein the light emitting layer comprises a phosphorescent dopant and Contains the above compound for organic EL device as a host material.
  • the structure of the organic EL element is not limited as long as it has a substrate, an anode, a cathode, and a light emitting layer, but has a hole injection transport layer between the anode and the light emitting layer, and an electron injection transport layer between the cathode and the light emitting layer. It is preferable. Furthermore, it is preferable to have a hole blocking layer between the light emitting layer and the electron injecting and transporting layer.
  • a material containing an organometallic complex containing at least one metal selected from ruthenium, rhodium, noradium, silver, rhenium, osmium, iridium, platinum and gold is preferable.
  • organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.
  • Ir having a noble metal element such as Ir as a central metal ( complexes such as ppy) 3, Ir (bt) 2 'acaC complexes such as 3, include complexes such as PtOEt3. Specific examples of these complexes are shown below, but are not limited to the following compounds.
  • the amount of the phosphorescent dopant contained in the light emitting layer is preferably in the range of 5 to 10 wt%.
  • the structure of the organic EL element of the present invention will be described with reference to the drawings.
  • the structure of the organic EL element of the present invention is not limited to the illustrated one.
  • FIG. 1 is a cross-sectional view schematically showing a structural example of a general organic EL device used in the present invention.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is hole transport.
  • 5 represents a light emitting layer
  • 6 represents an electron transport layer
  • 7 represents a cathode.
  • the substrate, the anode, the light emitting layer, and the cathode as the essential layers.
  • Hole between the layer and the electron injecting and transporting layer It may have a blocking layer.
  • the hole injection / transport layer means either or both of a hole injection layer and a hole transport layer
  • the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.
  • the structure opposite to that shown in FIG. 1, that is, the cathode 7, the electron transport layer 6, the light emitting layer 5, the hole transport layer 4, and the anode 2 can be laminated on the substrate 1 in this order.
  • the organic EL element of the present invention between two substrates, at least one of which is highly transparent. Also in this case, layers can be added or omitted as necessary.
  • the present invention can be applied to any of a single element, an element having a structure in which an organic EL element is arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix. Can do.
  • the organic EL device of the present invention by containing a compound having a specific skeleton in the light emitting layer and a phosphorescent light emitting dopant, the organic EL device has higher luminous efficiency and driving than the conventional device using light emission from a singlet state. Devices with greatly improved stability can be obtained and can be used for full-color or multi-color panels!
  • 1,2-cyclohexanedione (33.3 g, 297.0 mmol) and phenylhydrazine hydrochloride (86.0 g, 594.7 mmol) were added to a 2000 ml three-neck flask purged with degassed nitrogen, and 1000 ml of ethanol was added thereto and stirred. Thereafter, 3.0 g (30.6 mmol) of concentrated sulfuric acid was dropped into the flask over 5 minutes. The mixture was then heated to 65 ° C and stirred for 4 hours. After cooling to room temperature, the resulting purple brown crystals were collected by filtration, and the collected crystals were washed twice with 500 ml of ethanol and reslurry washed.
  • the filtrate was transferred to a 2000 ml separatory funnel and separated into an organic layer and an aqueous layer.
  • the organic layer was washed with 500 ml of water three times, and then the obtained organic layer was dehydrated with magnesium sulfate. After magnesium sulfate was filtered off once, the solvent was distilled off under reduced pressure. Thereafter, the residue was purified by column chromatography to obtain 13.7 g (41.2 mmol, yield 40.6%) of white solid A.
  • the resulting white solid A is 11-phenylindolo [2,3_a] force rubazonole.
  • white solid B is 2-chloro-4,6-diphenyl-1,3,5-triazine.
  • Compound 3 had an EI-MS (M + 1) of 563 and a melting point of 263 ° C.
  • Example 2 Evaluation was conducted in the same manner as in Example 2 except that the thin film host material was changed to Alq3 instead of Compound 3, and a thin film was prepared. The results are shown in Table 1.
  • Comparative example 1 X [0061] When compound 3 is used as the host material of the light-emitting layer, energy is transferred to Ir (ppy) 3, and light emission from Ir (ppy) 3 is observed, but when Alq3 is used, Ir It can be seen that energy does not transition to (ppy) 3, and Al q3 itself emits fluorescence.
  • an organic EL device with a configuration in which the hole injection layer was omitted and an electron injection layer was added was created.
  • a glass substrate having an anode made of ITO was formed with a thickness of 150, each thin film at vacuum evaporation method, was laminated in vacuum 4.0 X 10- 4 Pa.
  • NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
  • Compound 3 and ippy) as a light-emitting layer were co-deposited from different vapor deposition sources on the hole transport layer to form a thickness of 25 nm.
  • the concentration of Ir (ppy) was 7.0 wt%.
  • Alq3 was formed to a thickness of 50 mm as an electron transport layer.
  • lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer.
  • aluminum (A1) was formed as an electrode with a thickness of 170 nm on the electron injection layer to produce an organic EL device.
  • 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 host material 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 host material for the light emitting layer.
  • Fig. 1 an organic EL device with an electron injection layer added was created.
  • anode made of thickness 150nm of ITO was formed, the respective thin films by vacuum vapor deposition, are stacked in a vacuum 4.0 X 10- 4 Pa.
  • CuPC copper phthalocyanine
  • NPB was formed to a thickness of 40 nm as a hole transport layer.
  • Compound 3 and Ir (ppy) were co-deposited as a light emitting layer on the hole transport layer from different deposition sources to form a thickness of 35 nm.
  • the concentration of Ir (ppy) was 7.0 wt%
  • Alq3 was formed to a thickness of 40 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer.
  • Al (A1) was formed as an electrode to a thickness of 170 nm to produce an organic EL device.
  • the organic EL element had the light emission characteristics shown in Table 3.
  • the luminance, voltage, and luminous efficiency are values at 10 mA m 2 .
  • the maximum wavelength of the device emission spectrum was 517 nm, and it was found that light emission with Ir (ppy) power was obtained.
  • An organic EL device was prepared in the same manner as in Example 10 except that the compounds obtained in Examples 4 to 8 (Compound Nos. 114, 116, 2, 29, 37 and 1) were used as the main component of the light emitting layer. did. Table 3 shows the emission characteristics. It was confirmed that all of the compounds obtained in Examples 4 to 8 (Compound Nos. 114, 116, 2, 29, 37, and 1) emitted Ir (ppy) power. [0079] [Table 3]
  • the organic EL device of the present invention can emit light with high luminance and high efficiency at a low voltage.
  • the organic EL device according to the present invention is a light source (for example, a light source of a copying machine) that has features as a flat panel display (for example, for an OA computer or a wall-mounted television), an in-vehicle display device, a mobile phone display or a surface light emitter. It can be applied to backlight light sources for liquid crystal displays and instruments), display boards, and indicator lights, and its technical value is great.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

明 細 書
有機電界発光素子用化合物及び有機電界発光素子
技術分野
[0001] 本発明は新規な有機電界発光素子用化合物及び有機電界発光素子（以下、有機 EL素子という）に関するものであり、詳しくは、燐光発光ドーパントと特定の構造を有 するホスト化合物を併用することにより、高輝度率を示す有機 EL素子に関するもので ある。
背景技術
[0002] 一般に、有機 EL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か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] 近年、有機薄膜を用いた EL素子の開発が行われるようになった。特に発光効率を 高めるため、電極からキャリアー注入の効率向上を目的として電極の種類の最適化 を行い、芳香族ジァミンからなる正孔輸送層と 8—ヒドロキシキノリンアルミニウム錯体 (以下、 Alq3という）からなる発光層とを電極間に薄膜として設けた素子の開発により、 従来のアントラセン等の単結晶を用いた素子と比較して大幅な発光効率の改善がな されたこと力、ら、自発光 ·高速応答性とレ、つたと特徴を持つ高性能フラットパネルへの 実用を目指して進められてきた。
[0004] 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。上記の芳香族ジァミンからなる正孔輸送層と Alq3からなる発光層とを設け た素子をはじめとした多くの素子が蛍光発光を利用したものであった力 S、燐光発光を 用いる、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。この目的のためにタマリ ン誘導体やべンゾフエノン誘導体を発光層とすることが検討されてきた力 S、極めて低 い輝度しか得られなかった。その後、三重項状態を利用する試みとして、ユーロピウ ム錯体を用いることが検討されてきた力 これも高効率の発光には至らなかった。
[0005] 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
特許文献 5：特開平 11-162650号公報
特許文献 6：特開平 11-176578号公報
[0006] 有機 EL素子の発光層に用いる燐光発光ドーパントとしては、特許文献 1等に多数 開示されている。代表的には、トリス (2-フエ二ルビリジン)イリジウム錯体（以下、 Ir(ppy)
3という）がある。
[0007] 有機 EL素子の発光層に用いるホスト材料として提案されているのは、特許文献 2で 紹介されて!/、る力ルバゾール化合物の CBPである。緑色燐光発光材料の Ir(ppy)3の ホスト材として 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層側に流出し、結果として Ir(ppy)3から の発光効率が低下する。
[0008] 上記の解決手段として、例えば特許文献 3のように、発光層と電子輸送層の間に正 孔阻止層を設ける手段がある。この正孔阻止層により正孔を発光層中に効率よく蓄 積することによって、発光層中での電子との再結合確率を向上させ、発光の高効率 化を達成すること力できる。現状一般的に用いられている正孔阻止材料として、 2,9- ジメチル -4,7-ジフエニル -1, 10-フエナント口リン（以下、 BCPという）及び p-フエニルフ エノラート-ビス (2-メチル -8-キノリノラート- N1, 08)アルミニウム（以下、 BAlqと!/、う）が 挙げられる。これにより電子輸送層で電子と正孔の再結合が起こることを防止できる 1S BCPは室温でも結晶化し易く材料としての信頼性に欠けるため、素子寿命が極 端に短い。また、 BAlqは Tgが約 100°Cと比較的良好な素子寿命結果が報告されてい る力 正孔阻止能力が十分でなぐ Ir(ppy)3からの発光効率は低下する。
[0009] 一方、特許文献 4で紹介されている 3-フエニル _4-(1'-ナフチル) -5-フエニル -1,2,4 -トリアゾール (以下、 TAZという）も燐光有機 EL素子のホスト材として提案されている 、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(ppy)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-フエニルアミ ノ)ビフエニル（以下、 NPBという）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] また、特許文献 5及び 6で開示されているインドロ力ルバゾール化合物は、正孔輸 送材料としての使用が推奨されており、化合物の安定性も謳われている力 燐光ホス ト材料としての使用を教えるものではない。また、化合物の構造も本発明の化合物と 相違する。
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実用上有用な有 機 EL素子及びそれに適する化合物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、特定構造の化合物を有機 EL素子に使用する 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。
[0013] すなわち、本発明は、特定のインドロ力ルバゾール骨格の化合物を使用することに より、高効率かつ高レ、駆動安定性を有した実用上有用な有機 EL素子を提供するも のである。
[0014] 本発明の有機電界発光素子用化合物は、下記一般式（1)で表される。
Figure imgf000006_0001
ここで、環 Aは隣接環と任意の位置で縮合する式（la)で表される複素環を表し、 X は、 N又は CHを示し、 Xのうち少なくとも一つは、窒素原子である。 Ar〜Arは、独立
1 3 に縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を 示し、 Ar、 Arは Xを含む環と縮合環を形成してもよい。 Rは水素又は 1価の置換基を
2 3
示す。
一般式（1)で表される有機電界発光素子用化合物には、下記一般式（2)又は（3) で表される化合物がある。
Figure imgf000006_0002
一般式（2)及び（3)中、 X及び Ar〜ΑΓは一般式（1)のそれらと同意である。
1 3
[0016] また本発明は、上記の有機電界発光素子用化合物を含む有機層を有する有機電 界発光素子である。有利には、基板上に積層された陽極と陰極の間に、発光層を有 する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと上記一般式 (1)、（2)又は（3)で表される有機電界発光素子用化合物をホスト材料として含有す ることを特徴とする有機電界発光素子である。
図面の簡単な説明
[0017] [図 1]有機 EL素子の一例を示した模式断面図を示す。
符号の説明
[0018] 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
[0019] 以下、本発明の実施の形態を詳細に説明する。
[0020] 本発明の有機 EL素子用化合物は、上記一般式（1)で表される。一般式（1)で表さ れる化合物は、力ルバゾール環と、インドール環が縮合したインドロ力ルバゾール骨 格を有する。そして、 3個の Xを含む環 (X含有環という）が力ルバゾール環の Νに結合 し、各環に R又は Ar〜Arが結合した構造を有する。なお、インドール環は環 Αとベン
1 3
ゼン環との縮合環である。
[0021] 式中、環 Aは隣接環と縮合する式（la)で表される複素環を表す。ここで、式（la)で 表される複素環は隣接する力ルバゾール環の任意の位置で縮合することができる。 具体的には、力ルバゾール環の 2,3-位、 3,4-位又は 4,5-位の位置で縮合することが できる。
[0022] 力ルバゾール環の Nに結合する X含有環において、 Xは CH又は Nを示す力 少なく とも一つの Xは窒素原子である。好ましくは 1、 2又は 3つの Xが窒素原子である。
[0023] Ar〜Arは、縮環構造でない置換若しくは未置換の芳香族炭化水素基又は縮環
1 3
構造でない置換若しくは未置換の芳香族複素環基を示す。好ましい未置換の芳香 族炭化水素基としては、フエニル基、ビフエ二ル基、ターフェニル基、テトラフェニル 基等が挙げられる。好ましい未置換の芳香族複素環基としては、ピリジル基、ピリミジ ル基、トリアジル基、イミダゾリル基、チェニル基等が挙げられる。
これらの芳香族炭化水素基又は芳香族複素環基が置換基を有する場合、好ましレ、 置換基としては c〜cのアルキル基、 c〜cのアルコキシ基、フエノキシ基、アルキ
1 4 1 4
ルチオ基、置換アミノ基、ァセチル基等が挙げられる。また、炭素数 5〜； 18の芳香族 炭化水素基、及び炭素数 3〜； 17の芳香族複素環基等が挙げられる。
また、 Ar又は Arは X含有環と縮合して縮合環を形成してもよい。
2 3
[0024] 力ルバゾール環の Νに結合する X含有環において、この環がピリジン環の場合は、 一般式（1)において、力ルバゾール環の Νに結合する炭素に対し Ρ-位の Xが窒素で あること力 S好ましく、ピリミジン環の場合は、 0-位の 2つの Xが窒素であることが好まし い。
[0025] Rは、水素又は 1価の置換基を表す。 Rは独立に、水素又はアルキル基、ァラルキ ル基、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、ジァリールァミノ 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、力 ノレボキシル基、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、置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基である。好 ましい 1価の置換基としては、 C〜Cのアルキル基、 C〜Cのアルコキシ基、フエノ
1 4 1 4
キシ基、アルキルチオ基、置換アミノ基、ァセチル基等が挙げられる。更に、置換若し くは未置換の炭素数 5〜； 18の芳香族炭化水素基又は炭素数 3〜； 17の芳香族複素 環基が好ましく挙げられる。
[0026] 上記一般式（1)で表される化合物の中でも、好ましい化合物として上記一般式（2) 及び（3)で表される化合物がある。そして、一般式（2)及び（3)における X、 Ar〜Ar
1 3 及び Rは、一般式（1)中の X、 Ar〜Ar及び Rと対応し、同意である。好ましい X、 Ar
1 3 1
〜Ar及び Rについても上記と同様である。なお、同意であるとは、これらの記号の定
3
義が同一という意味であり、これらの記号が複数存在する場合は、上記定義の範囲 内で相互に変化してもよい。
[0027] 本発明の有機 EL素子用化合物は公知の方法で容易に製造することができる。例 えば、一般式（2)で表される化合物は、 Synlett，2005，No. l，p42-48に示される合成例 を参考にして以下の反応式により製造することができる。
Figure imgf000009_0001
Figure imgf000009_0002
また、一般式（3)は、 Archiv der Pharmazie (Weinheim, Germany), 1987,320(3),p280 -2に示される合成例を参考にして以下の反応式により製造することができる。次式に おいて、 Lは Ar 〜Arと同じ意味を有する。
3
Figure imgf000009_0003
[0030] 一般式（1)又は（2)、 （3)で表される化合物の好ましい具体例を以下に示す力 こ れらに限定するものではない。
Figure imgf000010_0001
(1) (3)
Figure imgf000010_0002
Figure imgf000011_0001
) ( 52
( ) (ε ) ( )
Figure imgf000012_0001
ZLU0/L00Zdr/13d 01- 917.9S0/800Z OAV

Figure imgf000013_0001
Figure imgf000013_0002
Figure imgf000014_0001
星9
Figure imgf000015_0001
Figure imgf000016_0001
0037
Figure imgf000017_0001
Figure imgf000017_0002
0038 皿
() 1 ΐΐ
Figure imgf000018_0001
Figure imgf000019_0001
) ()9 Ν τ u Ν ΐ
Figure imgf000020_0001
( 1 2 9 ) ( 1 3 0 ) ( 1 3 1 )
Figure imgf000020_0002
( 1 3 2 )
[0042] 本発明の有機電界発光素子用化合物は、有機 EL素子の有機層に含有させること により、優れた有機電界発光素子を与える。有利には、発光層、正孔輸送層、電子 輸送層及び正孔阻止素子層から選ばれる少なくとも一つの有機層に含有させること がよい。更に好ましくは、燐光発光ドーパントを含有する発光層のホスト材料として含 有させることがよい。
[0043] 本発明の有機電界発光素子は、有利には基板上に積層された陽極と陰極の間に 、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパント と上記の有機 EL素子用化合物をホスト材料として含有する。有機 EL素子の構造は 、基板、陽極、陰極及び発光層を有するものであればよいが、陽極と発光層の間に 正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有することが好ましい。 更に、発光層と電子注入輸送層の間に正孔阻止層を有することが好ましい。
[0044] 発光層における燐光発光ドーパント材料としては、ルテニウム、ロジウム、ノ 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よい。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。
[0045] 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が、下記の化合物に限定されない。
Figure imgf000021_0001
Figure imgf000022_0001
[0048] 前記燐光発光ドーパントが発光層中に含有される量は、 5〜； 10重量％の範囲にあ ることが好ましい。
[0049] 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が、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。
[0050] 図 1は本発明に用いられる一般的な有機 EL素子の構造例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。本発明の有機 EL素子では、基板、陽極、発光 層及び陰極を必須の層として有する力 必須の層以外の層以外に、正孔注入輸送 層、電子注入輸送層を有することがよぐ更に発光層と電子注入輸送層の間に正孔 阻止層を有することがよい。なお、正孔注入輸送層は、正孔注入層と正孔輸送層の いずれか又は両者意味し、電子注入輸送層は、電子注入層と電子輸送層のいずれ か又は両者意味する。
[0051] 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、既述したように少なくとも一 方が透明性の高い 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。この場合も、必要により層を追加したり、省略したりすることが可能である。
[0052] 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 とができる。本発明の有機 EL素子によれば、発光層に特定の骨格を有する化合物と 、燐光発光ドーパントを含有させることにより、従来の一重項状態からの発光を用い た素子よりも発光効率が高くかつ駆動安定性においても大きく改善された素子が得 られ、フルカラーあるいはマルチカラーのパネルへの応用にお!/、て優れた性能を発 揮できる。
実施例
[0053] 以下、本発明につき、実施例によって更に詳しく説明する力 本発明は勿論、これ らの実施例に限定されるものではなぐその要旨を越えない限りにおいて、種々の形 態で実施することが可能である。なお、化合物番号は上記化学式に付した番号に対 応する。
[0054] 実施例 1
脱気窒素置換した 2000ml三口フラスコに 1,2-シクロへキサンジオン 33.3g(297.0mm ol)、フエニルヒドラジン塩酸塩 86.0g (594.7mmol)を加え、これにエタノール 1000mlを 加えて攪拌させた。その後、同フラスコ内に濃硫酸 3.0g (30.6mmol)を 5分間かけ滴下 した。その後 65°Cまで加熱し、 4時間攪拌した。室温まで冷却した後、生じた紫茶色 結晶を濾取した後、濾取した結晶をエタノール 500mlで二回、リスラリー洗浄をおこな つた。これを、減圧乾燥して紫茶色粉末 80.0g (280.5mmol、収率 96.3%)を得た。 次に、 1000ml三口フラスコに上記紫茶色粉末 72.0g (261.5mmol)を加え、これに酢 酸 720g、トリフルォロ酢酸 72.0gを加えて攪拌させた。その後 100°Cまで加熱し、 15時 間攪拌した。室温まで冷却した後、生じた黄色結晶を濾取した後、濾取した結晶を酢 酸 200mlでリンス洗浄をおこなった後、へキサン 200mlでリンス洗浄をおこなった。これ を、減圧乾燥して白色粉末 A' 30.0g (117.1mmol、収率 44.8%)を得た。得られた白色 粉末 A，は、インドロ [2，3-a]力ルバゾールである。
[0055] 次に、脱気窒素置換した 1000ml三口フラスコに上記で得た白色粉末 26.0g (101.4m mol)、ョードベンゼン 122.7g (601.4mmol)、よう化銅 54.7g (287.2mmol)、炭酸カリウム 66.7g (482.6mmol)、これにキノリン 800mlを加えて攪拌させた。その後 190°Cまで加熱 し、 72時間攪拌した。一旦、室温まで冷却した後、水 500ml、ジクロロメタン 500mlを加 え、攪拌を行った後、生じた黄色結晶を濾取した。濾液を 2000ml分液ロートへ移し、 有機層と水層に分画した。有機層を 500mlの水で三回洗浄し、その後、得られた有機 層を硫酸マグネシウムで脱水を行い、一旦、硫酸マグネシウムを濾別した後、溶媒を 減圧留去した。その後、カラムクロマトグラフィーで精製して白色固体 A 13.7g (41.2m mol、収率 40.6%)を得た。得られた白色固体 Aは、 11-フエニルインドロ [2，3_a]力ルバ ゾーノレである。
[0056] 次に、脱気窒素置換した 200ml三口フラスコに塩化シァヌル 12.5g (0.068mol)、脱水 THF 55mlを加え、氷浴中にて窒素気流中下で攪拌を行う。その後、 32%臭化フエ二 ルマグネシウム THF溶液 105.6g(0.186mol)を同フラスコ内に 2時間かけ滴下した。滴 下中の温度は 15°C以下を保った。滴下終了後、 1.5時間攪拌を継続した。その後、同 フラスコ内にトルエン 80gを加えた。その後、氷浴中にて冷却を行い、同フラスコ内に 1 2%HClaq 76.5g(0.254mol)を 15分かけ滴下した。滴下中の温度は 30°C以下を保つ た。フラスコ内容物を 500ml分液ロートへ移し、有機層と水層に分画した。有機層を 10 0mlの水で三回洗浄し、その後、得られた有機層を硫酸マグネシウムで脱水を行い、 一旦、硫酸マグネシウムを濾別した後、溶媒を減圧留去し 21. lgのクルード品を得た。 その後、メタノール 110gを加え、攪拌を 1時間行った後に析出物を濾別し、真空乾燥 機にて減圧乾燥を行い白色固体 B 14.5g (6.5mmol、収率 50.2%)を得た。得られた 白色固体 Bは、 2-クロ口- 4,6 -ジフエニル -1,3,5-トリアジンである。
[0057] 次に、脱気窒素置換した 2000ml三口フラスコに 55%水素化ナトリウム 2.18g (50.0mm ol)、脱水 Ν,Ν' -ジメチルホルムアミド 70mlを加え、窒素気流中下で攪拌を行う。上記 で得た白色固体 A 13.5g (40.6mmol)に脱水 N，N，-ジメチルホルムアミド 150mlを加え 、溶解させ、その後、同フラスコ内に 10分間かけ滴下した。滴下終了後、 1時間攪拌 を継続した。その後、上記で得た白色固体 B 10.4g (39.0mmol)に脱水 Ν,Ν' -ジメチ ルホルムアミド 150mlを加え、溶解させ、その後、同フラスコ内に 1時間かけ滴下した。 滴下終了後、 3時間攪拌を継続した。その後、水 600gを加え、析出した結晶を濾取し た。濾取した結晶を水 300gで二回リスラリーを行い、その後、メタノール 300gにてリス ラリーを行った。得られた結晶を真空乾燥機にて減圧乾燥を行い、黄色結晶 21.0g を得た。
次に 1000mlフラスコに上記で得た黄色結晶 21.0g、 THF108.6gを加え、溶解させた 。同フラスコ内にメタノール 660gを滴下した。析出物を濾別し、真空乾燥機にて減圧 乾燥を行い黄色固体（化合物 3) 12.7g (22.6mmol、収率 54.6%)を得た。
化合物 3の EI— MS (M+ 1)は 563、融点は 263°Cであった。
[0058] 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 3を蒸着 源から蒸着し、薄膜を O. lnm/秒にて 50匪の厚さで形成した。作成した薄膜を、蛍光 測定装置にて評価したところ、発光が観察された。
別に、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 3と Ir(ppy)3とを異なる蒸着源から蒸着し、 Ir(ppy)3の濃度が 7.0 %であるような薄膜を 0.1 匪/秒にて 50隱の厚さで形成した。この作成した薄膜を、蛍光測定装置にて評価し た。励起波長は化合物 3の極大吸収波長を使用し、そのときに出てくる光を観察し、 化合物 3単独の薄膜の場合に出てくる光と比較した。結果を表 1に示す。
[0059] 比較例 1
薄膜のホスト材料を化合物 3に代えて、 Alq3に変えて薄膜を作成した以外は、実施 例 2と同様にして評価した。結果を表 1に示す。
[0060] [表 1] ホス卜からの発光 ドーバントからの発光
実施例 2 X 〇
比較例 1 〇 X [0061] 発光層のホスト材料に化合物 3を用いた場合、 Ir(ppy)3にエネルギーが遷移し、 Ir (p py) 3からの発光が観察されるが、 Alq3を用いた場合は、 Ir(ppy)3にエネルギーが遷移 せず、 Al q3自身が蛍光を発することがわかる。
[0062] 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 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 3と i ppy)とを異なる蒸着源から、共 蒸着し、 25nmの厚さに形成した。この時、 Ir(ppy)の濃度は 7.0 wt%であった。次に、 電子輸送層として Alq3を 50隱の厚さに形成した。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 0.5nm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。
[0063] 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 2のような 発光特性を有することが確認された。表 2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かった。
[0064] 比較例 2
正孔輸送層として HMTPDを、発光層のホスト材料として 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。
[0065] 比較例 3
発光層のホスト材料として、 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。
[0066] [表 2] 輝度 (cd/m2) 電圧 (V) 視感発光効率
(lm/W)
実施例 3 2720 5. 2 16. 4
比較例 2 2050 13. 2 4. 9
比較例 3 1270 9. 5 4. 2 [0067] 実施例 4
(化合物 114の合成）
脱気窒素置換した 2000ml三口フラスコに 3，3 ' _メチレンジィンドール50.698(0.2058 mol)、オルトギ酸トリェチル 30.55g (0.2061mol)を加え、これにメタノール 640gを加えて 攪拌した。これに、濃硫酸 5.0g (0.0515mol)を 3分間かけ滴下した後、 1時間加熱還流 した。室温まで冷却した後、生じた赤茶色結晶を濾取し、得られた結晶をメタノール 5 00mlにて二回リスラリー洗浄した。溶媒を減圧留去し、赤茶色粉末状の固体 C36.81g (0.1438mol、収率 69.9%)を得た。この固体 Cはインドロ [3，2_b]力ルバゾールである。
[0068] 次に、脱気窒素置換した 2000ml三口フラスコに、 55%水素化ナトリウム 4.36g (100.0m mol)、脱水 DMF 70mlを加え、窒素気流下で攪拌した。これに、上記固体 C 10.4g (40. 6mmol)の脱水 DMF (150ml)溶液を 10分間かけ滴下し、滴下終了後、 1時間攪拌した 。次いで、 2-クロ口- 4,6-ジフエニル -1,3,5-トリァジン 20.9g (78.0mmol)の脱水 DMF (3 00ml)溶液を 1時間かけ滴下した。滴下終了後、 3時間攪拌を継続し、その後、水 900 gを加え、析出した結晶を濾取した。濾取した結晶を水 450gで二回リスラリー洗浄し、 更にメタノール 450gにてリスラリー洗浄した。溶媒を減圧留去し、褐色結晶 42.0gを得 た。これを THF及びメタノールにて晶析精製した後、溶媒を減圧留去し、淡褐色固体 (化合物 114) 13.4g (18.6mmol、収率 46%)を得た。
APCI-MS, m/z 719 [M+l]+ 融点， 498°C
[0069] 実施例 5
(化合物 116の合成）
脱気窒素置換した 200ml三口フラスコに、インドロ [3，2-b]力ルバゾール 1.3g (5.1mm ol)、ナトリウム _tert_ブトキシド 1.4g (14.6mmol)、酢酸パラジウム 8.2mg (0.037mmol)、 2,6-ジフエニル -4-ョードピリジン 6.4g (17.9mmol)及びキシレン 80mlを加え、室温で 1 時間攪拌した。これにトリ- tert-ブチルホスフィン 64mg(0.32mmol)を加え、 120°Cで 40 時間加熱攪拌した。室温まで冷却した後、水 70mlを加え、析出物を濾取した。得られ た固体をメタノール、トルエン、クロ口ホルムにて順次、加熱リスラリー精製することによ り淡褐色固体（化合物 116) 1.0g (1.4mmol、収率 27.5%)を得た。
APCI-MS, m/z 715 [M+l]+ 融点， 426°C [0070] 実施例 6
(化合物 2の合成）
脱気窒素置換した 1000ml三口フラスコに、 55%水素化ナトリウム 2.18g (0.056mol)、 脱水 DMF240mlを加え、窒素気流下で攪拌した。これに、 11-フエニルインドロ [2，3_a] 力ルバゾール 13.3g (0.04mol)の脱水 DMF (25ml)溶液を 10分間かけて滴下し、滴下 終了後、 1時間攪拌した。更に、 2， 4,6-トリクロ口- 1,3-ピリミジン 8.8g (0.048mol)の脱 水 DMF (150ml)溶液を 1時間かけ滴下した。滴下終了後、 3時間攪拌を継続し、その 後、水 500mlを加え、析出した結晶を濾取した。濾取した結晶を水 300gで二回リスラリ 一洗浄し、更にメタノール 300gにてリスラリー洗浄した。溶媒を減圧留去し、単黄色結 晶 18.2gを得た。得られた結晶を精製せずに、次の反応に用いた。
[0071] 次に 2000ml三口フラスコに、上記で得た単黄色結晶 18.2g (0.038mol)、フエ二ルポ ロン酸 9.73g (0.08mol)、テトラキス（トリフエニルホスフィン）パラジウム 1.84g (0.0016mo 1)エタノール 150ml、トルエン 450mlを加えて攪拌した。その後、炭酸ナトリウム 29.8g (0 .28mol)の水 (140ml)溶液を加え、 85°Cで 4時間攪拌した。室温まで冷却した後、水 20 0ml、トルエン 200mlを加え、有機層と水層に分画し、有機層を 200mlの水で洗浄した 。有機層を硫酸マグネシウムにて脱水し、硫酸マグネシウムを濾別した後、溶媒を減 圧留去した。これをジクロロメタン及びエタノールにて晶析精製した後、溶媒を減圧留 去し、白色固体（化合物 2) 5.2g (0.0092mol、収率 23%)を得た。
APCI-MS, m/z 563 [M+l]+ 融点， 252°C
[0072] 実施例 7
(化合物 29の合成）
脱気窒素置換した 100ml三口フラスコに、酢酸パラジウム（11) 0.21 g (0.94 mmol)、キ シレン（20 ml)、トリ tert-ブチルホスフィン 0.76 g (3.76 mmol)を加え、 60°Cで 30分 加熱攪拌した。この溶液を、窒素気流下 60°Cに熱されたインドロ [2，3-a]力ルバゾール 4.61 g (0.0180 mol)、 4-カルバゾリルブロモベンゼン 5.8 g (0.018 mol)及び tert-ブ トキシナトリウム 7.7 g (0.080 mol),のキシレン（180 ml)溶液中に送液した。その後 13 0°Cまで昇温し、同温度で 5時間加熱攪拌した。室温まで冷却した後、水 200 mlを 加えた。油水分離し、有機層を減圧濃縮し、粗生成物を得た。これをジクロロメタン及 びエタノールにて晶析精製した後、溶媒を減圧留去し、 11- (4-カルバゾリルフエニル )インドロ [2，3-a]力ルバゾール 4.2 g (0.0084 mol、収率 47%)を得た。
[0073] 次に、脱気窒素置換した 200ml三口フラスコに、 55%水素化ナトリウム 0.42g (0.0096m ol)、脱水 DMF 10mlを加え、窒素気流下で攪拌した。上記 11- (4-カルバゾリルフエ二 ノレ）インドロ [2，3-a]力ルバゾール 4.0 g(0.008 mol)の脱水 DMF (20ml)溶液を、 10分間 力、けて滴下した。滴下終了後、 1時間程度攪拌した後、これに 2-クロ口- 4,6-ジフエ二 ル -1,3,5-トリアジン 2.14 g (0.008 mol)の脱水 DMF (20ml)溶液を 1時間かけ滴下した 。滴下終了後、 3時間攪拌した後、水 100gを加え、析出した結晶を濾取した。濾取し た結晶を水 100gで二回リスラリー洗浄し、更にメタノール 100gにてリスラリー洗浄した 。溶媒を減圧留去し、 THF/メタノールによる晶出精製することで、黄色固体 (化合物 29) 3.0g (0.0041mol、収率 51%)を得た。
APCI-MS, m/z 729 [M+l]+ 融点， 319°C
[0074] 実施例 8
(化合物 37の合成）
脱気窒素置換した 2000ml三口フラスコに 55%水素化ナトリウム 4.80g (1 lO.Ommol)、 脱水 DMF 70mlを加え、窒素気流下で攪拌した。これに、インドロ [2，3_a]カルバゾー ノレ 13.5g (52.7mmol)の脱水 DMF (150ml)溶液を、 10分間かけて滴下した。滴下終了 後、 1時間程度攪拌した後、これに 2-クロ口- 4,6-ジフエニル -1,3,5-トリァジン 29.4g ( l lO.Ommol)の脱水 DMF(150)溶液を 1時間かけ滴下した。滴下終了後、 3時間攪拌し た後、水 900gを加え、析出した結晶を濾取した。濾取した結晶を水 450gで二回リスラ リー洗浄し、更にメタノール 450gにてリスラリー洗浄した。溶媒を減圧留去し、結晶 35 .0gを得た。これを THF/メタノールによる晶出精製することで、黄色固体 (化合物 37) 24g (33.4mmol、収率 63.4%)を得た。
APCI-MS, m/z 719 [M+l]+ 融点， 426°C
[0075] 実施例 9
(化合物 1の合成）
脱気窒素置換した 20ml三口フラスコに、酢酸パラジウム（11) 0.071 g (0.32 mmol)、 キシレン（5 ml)、トリ tert-ブチルホスフィン 0· 32 ml(1.26 mmol)を加え、 60°Cで 30 分加熱攪拌した。この溶液を、窒素気流下 60°Cに熱された 11-フエニルインドロ [2，3-a ]力ルバゾール 1.99 g (0.0060 mol)、 2,6-ジフエニル- 4-ョードピリジン 2.46 g (0.0069 mol)及び tert-ブトキシナトリウム 2.57 g (0.0267 mol),のキシレン（60 ml)溶液中に 送液した。その後 130°Cまで昇温し、同温度で 5時間加熱攪拌した。室温まで冷却し た後、水 70 mlを加えた。油水分離し、有機層を減圧濃縮し、 4.85gの粗生成物を得 た。これをジクロロメタン及びエタノールにて晶析精製した後、溶媒を減圧留去し、白 色固体（化合物 1) 1.43 g (0.0025mol、収率 36%)を得た。
APCI-MS, m/z 562 [M+l]+ 融点， 277°C，287°C
[0076] 実施例 10
図 1において、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 150nm 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上に正孔注入層として、銅フタロシアニン (C uPC)を 20 nmの厚さに形成した。次に、正孔輸送層として NPBを 40 nm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 3と Ir(ppy)とを異なる蒸着源 力ら、共蒸着し、 35nmの厚さに形成した。この時、 Ir(ppy)の濃度は 7.0 wt%であった
。次に、電子輸送層として Alq3を 40nm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 0.5nm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
〇
[0077] 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 3のような 発光特性を有することが確認された。表 3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かった。
[0078] 実施例 11〜； 16
発光層の主成分として、実施例 4〜8で得られた化合物（化合物 No.114、 116、 2、 29 、 37及び 1)を用いた以外は実施例 10と同様にして有機 EL素子を作成した。表 3に 発光特性を示す。実施例 4〜8で得られた化合物（化合物 No.114、 116、 2、 29、 37及 び 1)すべてにおいて、 Ir(ppy)力、らの発光が得られていることを確認した。 [0079] [表 3]
Figure imgf000031_0001
産業上の利用の可能性
[0080] 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素子はフラットパネル'ディスプレイ (例えば OA 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、標識灯への応用が考えられ、その技術的価値は大きいものであ

Claims

請求の範囲
[1] 下記一般式（1)で示される有機電界発光素子用化合物。
Figure imgf000032_0001
ここで、環 Aは隣接環と任意の位置で縮合する式（la)で表される複素環を表し、 X は、 CH又は Nを示し、 Xのうち少なくとも一つは、窒素原子である。 Ar〜Arは、独立
1 3 に縮環構造でない置換若しくは未置換の芳香族炭化水素基又は芳香族複素環基を 示し、 Ar又は Arは Xを含む環と縮合環を形成してもよい。 Rは水素又は 1価の置換
2 3
基を示す。
[2] 一般式（1)において、 Rが独立に、水素又はアルキル基、ァラルキル基、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、ジァリールアミノ基、ジァラルキ ルァミノ基、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 若しくは未置換の芳香族炭化水素基又は芳香族複素環基である請求項 1に記載の 有機電界発光素子用化合物。
[3] 一般式（1)において、 Rが独立に、水素、置換若しくは未置換の炭素数 5〜； 18の芳 香族炭化水素基又は炭素数 3〜； 17の芳香族複素環基からなる請求項 1に記載の有 機電界発光素子用化合物。
[4] 一般式（1)において、 Ar〜Arが独立して、置換若しくは未置換のフエニル基、又
1 3
は置換若しくは未置換の炭素数 2〜5の芳香族複素環基からなる請求項 1に記載の 有機電界発光素子用化合物。
下記一般式（2)又は（3)で示される請求項 1に記載の有機電界発光素子用化合物
Figure imgf000033_0001
ここで、 X及び Ar〜ΑΓは、式（1)及び（la)中の X及び Ar〜ΑΓと同意である。
1 3 1 3
[6] 請求項;!〜 5のいずれかに記載の有機電界発光素子用化合物を含む有機層を有 する有機電界発光素子。
[7] 有機電界発光素子用化合物を含む有機層が、発光層、正孔輸送層、電子輸送層 及び正孔阻止素子層から選ばれる少なくとも一つの層である請求項 6記載の有機電 界発光素子。
[8] 有機電界発光素子用化合物を含む有機層が、基板上に積層された陽極と陰極の 間に、発光層を有する有機電界発光素子の発光層であり、該発光層が燐光発光性 ドーパントと該有機電界発光素子用化合物をホスト材料として含有する請求項 6記載 の有機電界発光素子。
[9] 陽極と発光層の間に正孔注入輸送層を有し、陰極と発光層の間に電子注入輸送 層を有してなる請求項 8記載の有機電界発光素子。
[10] 発光層と電子注入輸送層の間に正孔阻止層を有してなる請求項 9記載の有機電 界発光素子。
PCT/JP2007/071728 2006-11-09 2007-11-08 Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique WO2008056746A1 (fr)

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WO2024094592A2 (de) 2022-11-01 2024-05-10 Merck Patent Gmbh Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen
WO2024105066A1 (en) 2022-11-17 2024-05-23 Merck Patent Gmbh Materials for organic electroluminescent devices
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EP4386065A1 (en) 2022-12-14 2024-06-19 Universal Display Corporation Organic electroluminescent materials and devices
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WO2024132993A1 (de) 2022-12-19 2024-06-27 Merck Patent Gmbh Materialien für elektronische vorrichtungen
WO2024133048A1 (en) 2022-12-20 2024-06-27 Merck Patent Gmbh Method for preparing deuterated aromatic compounds
WO2024149694A1 (de) 2023-01-10 2024-07-18 Merck Patent Gmbh Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen
WO2024153568A1 (de) 2023-01-17 2024-07-25 Merck Patent Gmbh Heterocyclen für organische elektrolumineszenzvorrichtungen
WO2024170605A1 (en) 2023-02-17 2024-08-22 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2024184050A1 (de) 2023-03-07 2024-09-12 Merck Patent Gmbh Cyclische stickstoffverbindungen für organische elektrolumineszenzvorrichtungen
WO2024194264A1 (de) 2023-03-20 2024-09-26 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
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CN101511834A (zh) 2009-08-19
EP2080762B1 (en) 2016-09-14
EP2080762A4 (en) 2012-03-14
KR20090086057A (ko) 2009-08-10
JPWO2008056746A1 (ja) 2010-02-25
TW200838979A (en) 2008-10-01
EP2080762A1 (en) 2009-07-22
TWI418607B (zh) 2013-12-11
US8062769B2 (en) 2011-11-22
CN101511834B (zh) 2013-03-27
JP4388590B2 (ja) 2009-12-24
KR100955993B1 (ko) 2010-05-04
US20100187977A1 (en) 2010-07-29

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