WO2018155826A1 - Nouveau composé et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé et élément électroluminescent organique l'utilisant Download PDF

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WO2018155826A1
WO2018155826A1 PCT/KR2018/001181 KR2018001181W WO2018155826A1 WO 2018155826 A1 WO2018155826 A1 WO 2018155826A1 KR 2018001181 W KR2018001181 W KR 2018001181W WO 2018155826 A1 WO2018155826 A1 WO 2018155826A1
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group
substituted
compound
unsubstituted
light emitting
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PCT/KR2018/001181
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English (en)
Korean (ko)
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김진주
곽지원
이성재
한수진
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주식회사 엘지화학
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Priority claimed from KR1020180009506A external-priority patent/KR102021584B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880002837.6A priority Critical patent/CN109476597B/zh
Publication of WO2018155826A1 publication Critical patent/WO2018155826A1/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • 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, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer electron transport layer, an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by Formula 1:
  • al and a2 are each independently an integer of 0 to 2
  • bl to b6 each independently represent an integer of 0 to 3;
  • the present invention is a first electrode; A low) two electrode provided opposite the one electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. .
  • 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 an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • ⁇ ⁇ " means a bond connected to another substituent, and a single bond means the case where no separate atom exists in the part represented by and L ⁇ 2> .
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may 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 have a structure as follows.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • tert-butyl sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl ⁇ isopentyl, neopentyl, ter t-pentyl, nuclear chamber, n-nuclear chamber, 1 ⁇ methylpentyl, 2- Methylpentyl, 4-methyl ⁇ 2—pentyl, 3, 3-dimethylbutyl, 2—ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n—octyl, ter t -Octyl, 1-methylheptyl, 2-ethylnuclear, 2-propylpentyl, n-nonyl, 2, 2-dimethylheptyl, 1-ethyl-propyl, 1, 1-di
  • 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.
  • cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms.
  • the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3 ⁇ methylcyclopentyl, 2, 3—dimethylcyclopentyl, cyclonuclear chamber, 3-methylcyclonuclear chamber, 4-methylcyclonuclear chamber, 2, 3-dimethylcyclonuclear chamber, 3, 4, 5—trimethylcyclonuclear chamber, 4— t ert- Butylcyclonuclear chamber, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but may be 6 to 60 carbon atoms . It is preferably, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, 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 phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl 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.
  • the fluorenyl group is substituted
  • the present invention is not limited thereto.
  • the heteroaryl is a heteroaryl containing one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • by the heteroaryl of Tero arylamine is a description associated with the above-mentioned heteroaryl group may be applied.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aforementioned aryl group may be applied except that arylene is bivalent.
  • the description of the aforementioned heteroaryl may be applied except that the heteroarylene is divalent.
  • the hydrocarbon ring is not monovalent, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocycle is not one group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding.
  • the present invention provides a compound represented by the formula (1).
  • L 2 are each independently substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted Anthracenylene substituted or unsubstituted fluoranthhenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted carbazoleylene, substituted or unsubstituted fluorenylene Or substituted or unsubstituted spiro-fluorenylene.
  • L 2 may each independently be a single bond, or any one selected from the group consisting of: Specifically, for example, and L 2 may be each independently a single bond, or one as follows: Furthermore, An is a substituted or unsubstituted C 6 - 20 aryl; Or C 2 containing 1 to 3 heteroatoms, a substituted or unsubstituted ring of the S - to 20 may be an interrogating aryl. For example, An may each independently be any one selected from the group consisting of:
  • Each L is independently a single bond; Or substituted or unsubstituted C 6 -60 arylene, ⁇ Is 0, s, or CZ 4 Z 5 ,
  • li to Z 5 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; d- 20 alkyl; d- 20 haloalkyl; C 6 - 20 aryl; 20 is a heteroaryl, - C 2 containing the solution for interrogating atom of 0 or S 1 or more
  • nl to n3 are each independently an integer of 0 to 3.
  • ⁇ ⁇ to 3 ⁇ 4 are each independently hydrogen, deuterium, phenyl, or biphenyl,
  • ⁇ 4 and ⁇ 5 are each independently methyl or phenyl
  • nl to ⁇ 3 are each independently 0, 1, or 2.
  • A may be any one selected from the group consisting of:
  • al and a2 may be each independently 1 or 2.
  • Ri to R 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; d- 20 alkyl; Or C 6 - 20 may be an aryl group.
  • Ri to 3 ⁇ 4 may each independently be hydrogen, deuterium, halogen, cyano, nitro, methyl, or phenyl, and bl to b6 may each independently be 0 or 1.
  • al represents the number of, and when al is 2 or more, two or more may be the same or different from each other.
  • the description of bl to b6 and nl to n3 may be understood with reference to the description of al and the structure of Chemical Formula 1.
  • the compound may be represented by the formula 1A, 1B or 1C:
  • Arl is as defined in the formula (1).
  • the compound may be any one selected from the group consisting of the following compounds:
  • the compound represented by Formula 1 has a structure in which a penal and a linker (or a nitrogen atom) bonded to position 9 of two carbazole groups are connected to an ortho position, and the organic light emitting device using the same is represented by 9 of two carbazole groups.
  • a penal and a linker (or a nitrogen atom) bonded to position 9 of two carbazole groups are connected to an ortho position
  • the organic light emitting device using the same is represented by 9 of two carbazole groups.
  • a compound having a structure in which a phenyl bonded to a position and a linker (or a nitrogen atom) are connected to a met a or para position they may have high efficiency, low driving voltage, high brightness, and long life.
  • the compound represented by Formula 1 may be prepared by the same method as in Scheme 1 below. The manufacturing method may be embodied more than in the production examples to be described later.
  • the reaction is a step of preparing a compound represented by Chemical Formula A (corresponding to a compound represented by Chemical Formula 1 herein) by reacting the compound represented by Chemical Formula I—a with the compound represented by Chemical Formula 1-b. .
  • the reaction is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the compound represented by Formula 1 of the present application can be prepared by appropriately replacing the starting material in accordance with the structure of the compound to be prepared with reference to Scheme 1.
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the present invention comprises a first electrode; A second electrode provided to face the first electrode; And between the first electrode and the second electrode.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • 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 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 material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, an electron transport layer and an electron injection layer between the light emitting layer and the second electrode, in addition to the light emitting layer as an organic layer. It may have a structure to.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more layers of organic matters, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light emitting diode 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. As shown in FIG.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4; It is.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes a compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting diode 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.
  • PVD physical vapor deposition
  • the alloy may be deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Chemical Formula 1 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 blading, inkjet 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).
  • 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 usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, acetic acid 3] .water, indium tin oxide (?), And indium zinc oxide (IZ0); ⁇ 0: A1 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-l, 2-dioxy) thiophene] (PED0T), polypyri and polyaniline, and the like, but are not limited thereto. no.
  • 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 metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, 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 the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic matter, nucleonitrile-nuclear azatriphenylene-based organic matter, Quinacridone (quinacr i done) -based organics, perylene-based organics, anthraquinone ' and polyaniline and polythiophene-based conductive polymers, but is not limited to these.
  • 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 material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the light emitting layer may include a host material and a dopant material as described above.
  • the host material may further 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, and fluoranthene compounds
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types.
  • the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, as an aromatic amine derivative Having a substituted or unsubstituted arylamino group .
  • Examples of the condensed aromatic ring derivative include pyrene, anthracene and chrysene periplanthene having an arylamino group.
  • Examples of the styrylamine compound include a substituted or unsubstituted arylamine.
  • a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted.
  • styryl amine, styryl diamine, styryl triamine, styryl tetraamine and the like but is not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes .
  • 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 that can inject electrons well from the cathode and transfer them to the light emitting layer. Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; 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.
  • cathode materials are conventional materials having a low work function followed by a layer of aluminum or silver. And specifically seseum, barium, calcium, yite 'reubyum and samarium, in each case followed by a layer of aluminum or silver layer.
  • the electron-implanted layer is a layer which injects electrons from an electrode, has the ability to transport electrons, an electron injection effect from a cathode, a light emitting layer or a. Having an excellent electron injection effect to a light emitting material, generated in the light emitting excitons
  • the compound which prevents the movement to a hole injection layer, and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, di.phenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and derivatives thereof, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10—hydroxybenzo [h] quinolinato) zinc, bis (2—methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( 0—cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium, etc.
  • the organic light emitting device according to the present invention 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 Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the production of the compound represented by Chemical Formula 1 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. Production Example
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Mi 1 lipore Co. was used as distilled water.
  • the ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and 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.
  • nuclei nitrile hexaazatriphenylene (HAT) of the following formula on the ⁇ transparent electrode by thermal vacuum deposition to a thickness of 500A to form a hole injection layer.
  • Compound 1 which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport worm.
  • TCTA EB 1
  • the following compound ⁇ and LiQ were vacuum deposited on the emission layer at a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300A.
  • LiF Lithium fluoride
  • aluminum at a thickness of 2,000 A were sequentially deposited on the electron injection and transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec.
  • the organic light emitting device was manufactured by maintaining ( ⁇ 7 to 5 X 10 "6 torr.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using Compound HT 1 to HT 3 instead of Compound 1 in Experimental Example 1-1.
  • the glass substrate coated with a thin film of I0 (indium tin oxide) ⁇ , ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly was used as a filter of ⁇ 1 ipore Co. product as distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and 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 nucleus nitrile nuxaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 A on the prepared IT0 transparent electrode to form a hole injection layer.
  • An organic light emitting device was manufactured by sequentially depositing lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2,000 A on the electron transport layer to form a cathode.
  • LiF lithium fluoride
  • the deposition rate of organic material was maintained at 1 A / sec
  • LiF was maintained at 0.2 A / sec
  • aluminum was maintained at a deposition rate of 3 to 7 A / sec . 2-10
  • An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except for using.
  • the glass substrate coated with a thin film of I0 (indium tin oxide) ⁇ , ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • Fischer Co. product was used as a detergent
  • distilled water filtered as a second filter was used as a filter of Mi 1 lipore Co. product as distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and 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.
  • hexanitrile nuxaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 A on the IT0 transparent electrode thus prepared to form a hole injection layer.
  • the hole transport layer was formed by vacuum depositing the following HT 1-1, which is a material for transporting holes on the hole injection layer.
  • the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the electron blocking layer with a film thickness of 300A.
  • the following compound ET1 and LiQ were vacuum deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport insect at a thickness of 300A.
  • Lithium fluoride (LiF) and aluminum at a thickness of 2,000 A were sequentially deposited on the electron injection and transport layer to form a cathode. .
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec.
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 1 ( ⁇ 6 torr.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 3-1 except for using the following EB 1 to EB 3 instead of the compound 1 in Experimental Example 3-1.
  • Substrate 2 Anode
  • Hole injection 6 Hole transport layer

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique l'utilisant.
PCT/KR2018/001181 2017-02-24 2018-01-26 Nouveau composé et élément électroluminescent organique l'utilisant WO2018155826A1 (fr)

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KR1020180009506A KR102021584B1 (ko) 2017-02-24 2018-01-25 신규한 화합물 및 이를 이용한 유기발광 소자

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WO2019189033A1 (fr) * 2018-03-28 2019-10-03 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2021060239A1 (fr) * 2019-09-26 2021-04-01 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN113382983A (zh) * 2019-01-30 2021-09-10 Lt素材株式会社 化合物、有机光电装置以及显示装置
US11479544B2 (en) * 2017-03-08 2022-10-25 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
WO2023027173A1 (fr) * 2021-08-27 2023-03-02 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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KR20160091198A (ko) * 2015-01-23 2016-08-02 삼성에스디아이 주식회사 유기 광전자 소자 및 표시 장치
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Publication number Priority date Publication date Assignee Title
US11479544B2 (en) * 2017-03-08 2022-10-25 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
WO2019189033A1 (fr) * 2018-03-28 2019-10-03 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
CN113382983A (zh) * 2019-01-30 2021-09-10 Lt素材株式会社 化合物、有机光电装置以及显示装置
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EP3919475A4 (fr) * 2019-01-30 2022-10-19 LT Materials Co., Ltd. Composé, dispositif optoélectronique organique et dispositif d'affichage
WO2021060239A1 (fr) * 2019-09-26 2021-04-01 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
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WO2023027173A1 (fr) * 2021-08-27 2023-03-02 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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