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WO2018128425A1 - Complexe d'iridium et élément électroluminescent organique l'utilisant - Google Patents

Complexe d'iridium et élément électroluminescent organique l'utilisant Download PDF

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Publication number
WO2018128425A1
WO2018128425A1 PCT/KR2018/000197 KR2018000197W WO2018128425A1 WO 2018128425 A1 WO2018128425 A1 WO 2018128425A1 KR 2018000197 W KR2018000197 W KR 2018000197W WO 2018128425 A1 WO2018128425 A1 WO 2018128425A1
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group
light emitting
layer
compound
organic light
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PCT/KR2018/000197
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English (en)
Korean (ko)
Inventor
서상덕
김성소
홍성길
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주식회사 엘지화학
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Priority to CN201880002136.2A priority Critical patent/CN109311922A/zh
Publication of WO2018128425A1 publication Critical patent/WO2018128425A1/fr

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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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • 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
    • 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
    • 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

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent research on the luminance, driving voltage, and response speed characteristics.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic charge is often made of a multi-layered structure composed of different materials. .
  • Patent Document 0001 Korean Patent Publication No. 10— 2000-0051826
  • the present invention relates to an rhythm complex and an organic light emitting device using the same.
  • the present invention provides a compound represented by Formula 1 or Formula 2:
  • X is 0 or S
  • 3 ⁇ 4 is d-60 alkyl unsubstituted or substituted with deuterium; Silyl having 1 to 60 carbon atoms; Is substituted or unsubstituted C 6 -60 aryl,
  • R 2 and R 3 are each independently hydrogen; Or Cwo alkyl unsubstituted or substituted with deuterium.
  • n 1 or 2.
  • the present invention is a first electrode; A low 12 electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a light emitting insect including the compound.
  • the compound represented by Chemical Formula 1 or 2 may be used as an organic material layer of the organic light emitting device, particularly a material of the light emitting layer, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting device.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5 ;
  • substituted or unsubstituted is deuterium halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group imad group; amino group; phosphine oxide group; alkoxy group; aryloxy group alkylthioxy group Arylthioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; hetero An arylamine group; an arylamine group; an arylphosphine group; or an unsubstituted or substituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N,
  • the substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group, and can be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40.
  • the compound may be
  • the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula,
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • the compound may be as follows, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group. etc. _ t-butyldimethylsilyl group, a vinyl dimethyl silyl group, a propyl dimethylsilyl group, a triphenylsilyl group diphenylsilyl group, a phenyl silyl groups, but not limited to this.
  • the boron group is specifically trimethyl boron group, triethyl boron group, t- butyl dimethyl boron group. Triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • examples of the halogen groups include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl isobutyl, ter t-butyl, sec-butyl, 1-methyl-butyl, 1_ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber.
  • n-nuclear 1-methylpentyl. 2-methylpentyl.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1—propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3—butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl—1 ⁇ part
  • the cycloalkyl group is not particularly limited. It is preferably 3 to 60 carbon atoms, according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a cyclic group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, It is not limited.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryllenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In the case of the fluorenyl group,
  • the heterocyclic group is a heterocyclic group including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acri Dill, pyridazine.
  • Dibenzothiophene group benzofuranyl group, phenanthroline (phenanthrol ine), isooxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group, but are not limited thereto.
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group mentioned above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the above-mentioned alkyl group.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • 3 ⁇ 4 is unsubstituted or substituted with deuterium alkyl; Silyl having 3 to 10 carbon atoms; Or substituted or unsubstituted Ce-10 aryl. More preferably, ⁇ is methyl, ethyl, propyl.
  • the present invention provides, for example, a method for preparing a compound represented by Chemical Formula 1 or 2 (when n is 2), such as the following Scheme 1, and may be applied when n is 1:
  • the manufacturing method may be embodied in the following examples.
  • the present invention provides an organic light emitting device comprising the compound represented by Formula 1 or 2.
  • the present invention comprises a first electrode; A second electrode provided to face the low U electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the ' organic material layer includes a light emitting layer including a compound represented by Formula 1 or 2 above.
  • the organic material layer of the organic light emitting device of the present invention may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. for example.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic light emitting device according to the present invention, the anode, one layer on the substrate The organic layer and the cathode may be an organic light emitting device having a structure in which the organic layer is sequentially stacked.
  • the organic light emitting diode according to the present invention may be an organic light emitting diode having an inverted type structure in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer.
  • 2 shows a substrate 1, an anode 2, a hole injection layer 5, and a hole transport layer 6; Luminescent (7).
  • the example of the organic light emitting element which consists of the electron carrying layer 8 and the cathode 4 is shown.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except for including the compound represented by Chemical Formula 1 or 2.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate by using a physical vapor deposition method (PVD) such as sputtering or e-beam evaporation (e).
  • PVD physical vapor deposition method
  • An organic light emitting device is fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate Can be.
  • the compound represented by Chemical Formula 1 or 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor ball raiding, ink jet printing, screen printing, spraying, coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (W0 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include vanadium, chromium, copper and zinc.
  • Metals such as gold or alloys thereof;
  • Metal oxides such as zinc oxide, rhythm oxide, rhodium tin oxide (rro), zirconia zinc oxide ( ⁇ ⁇ ⁇ ); ⁇ 0: ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb;
  • Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene KPED0T), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium lithium, and gadolinium.
  • Metals such as aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode, and has a capability of transporting holes to a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect to a light emitting layer or a light emitting material, and excitons generated in the light emitting layer.
  • the compound which prevents the movement to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. It is preferable that the HOMO highest occupied molecul ar orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injection materials include metal porphyrin, oligothiophene, and arylamine series.
  • Organic matter A nucleus nitrile nucleated azatriphenylene-based organic matter, a quinacrlone-based organic matter, and a perylene-based organic matter. Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport layer is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the light emitting insect refers to a layer that emits light in the visible region by transporting and combining holes and electrons from the hole transport insect and the electron transport layer, respectively.
  • the emission layer may include a host material and a dopant material, and the compound represented by Chemical Formula 1 or 2 may be used as the dopant material.
  • the host material include a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable. Specific examples include A 1 complex of 8-hydroxyquinoline; Complexes including Al q 3 ; Organic radical compound; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum layer or silver worm. Specifically cesium. Barium, calcium. Ytterbium and samarium, followed by a layer of aluminum or silver in each case.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, and the hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper and bis (8-hydroxyquinolinato) manganese.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Chemical Formula 1 or 2 may be included in the organic solar cell or the organic transistor in addition to the organic light emitting device. Fabrication of the compound represented by Formula 1 or 2 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
  • iridium (III) chloride hydrate (15.0 g, 42.5 ⁇ l ol), and 2-phenylpyridine (2.2 g, 14.0 ⁇ l ol) were added 2-ethoxyethanol (140 ml). Put together with water (47 ml) and stir for 18 h under argon atmosphere reflux conditions. After the reaction was completed, the mixture was cooled to room temperature, the precipitate was filtered, washed with methanol and nucleic acid, dried, and used for the next reaction without further purification (21.7 g, yield 95%).
  • Compound 2 was prepared by the same method as the method for preparing compound 1, except that intermediate 2 was used instead of intermediate 1.
  • Compound 5 was prepared in the same manner as in the preparation of compound 1, except that Intermediate C was used instead of Intermediate A, and Intermediate 2 was used instead of Intermediate 1.
  • Compound 6 was prepared by the same method as the preparation of compound 1, except that Intermediate C was used instead of Intermediate A, and Intermediate 5 was used instead of Intermediate 1.
  • ITOClndi ⁇ Tin Oxide was thin film-coated glass substrate with a thickness of 1,400 A and placed in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • Fischer Co.'s Decon TM C0N705 was used as a detergent, and distilled water was filtered using a 0.22 ⁇ ⁇ sterilizing filter from Millipore Co.'s second distilled water.
  • ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried and then transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • a mixture of 95 wt% of the following HT-A compound and 5 wt% of the following P-D0PANT compound was thermally vacuum deposited to a thickness of 100 A on the ⁇ ⁇ transparent electrode thus prepared, followed by deposition of only the following HT-A compound to a thickness of 1150 A.
  • the following HT-B compound was thermally vacuum deposited to a thickness of 450 A on the hole transporter to form an electron blocking layer.
  • a mixture of the following GH compound (94 wt%) and compound 1 (6 wt%) prepared as a dopant as a host was vacuum deposited to a thickness of 400 A to form a light emitting layer.
  • the following ET-A compound was vacuum deposited to a thickness of 50 A on the light emitting layer to form a hole blocking layer.
  • the following ET-B compound and the following Liq compound were mixed at a weight ratio of 2: 1, and thermally vacuum-bonded to a thickness of 250 A to form an electron transporting layer, followed by LiF and magnesium at a weight ratio of 1: 1.
  • Magnesium and silver were mixed at a weight ratio of 1: 4 on the electron injection layer, and then, at a thickness of 160 A.
  • An organic light-emitting device was manufactured in the same manner as in Experiment 1, except for using the compound shown in Table 1 instead of the compound 1.
  • GD-4 GD-5 Voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light emitting diodes manufactured in the above Experimental Example and Comparative Experimental Example, respectively. The results are shown in the table below. 1 is shown. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm 2 .
  • the lifetime (T95) means the time until the initial luminance drops to 95% at a current density of 20 niA / cni 2 .
  • substrate 2 anode

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Abstract

La présente invention concerne un composé d'iridium et un élément électroluminescent organique l'utilisant.
PCT/KR2018/000197 2017-01-04 2018-01-04 Complexe d'iridium et élément électroluminescent organique l'utilisant WO2018128425A1 (fr)

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WO2019221484A1 (fr) * 2018-05-14 2019-11-21 주식회사 엘지화학 Composé organométallique et diode électroluminescente organique le comprenant
EP4328285A1 (fr) * 2022-08-25 2024-02-28 Beijing Summer Sprout Technology Co., Ltd. Matériau électroluminescent organique et dispositif associé

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JP2016219490A (ja) * 2015-05-15 2016-12-22 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置

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