WO2019054634A1 - Nouveau composé hétérocylique et dispositif électroluminescent organique utilisant celui-ci - Google Patents

Nouveau composé hétérocylique et dispositif électroluminescent organique utilisant celui-ci Download PDF

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WO2019054634A1
WO2019054634A1 PCT/KR2018/008986 KR2018008986W WO2019054634A1 WO 2019054634 A1 WO2019054634 A1 WO 2019054634A1 KR 2018008986 W KR2018008986 W KR 2018008986W WO 2019054634 A1 WO2019054634 A1 WO 2019054634A1
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substituted
unsubstituted
group
compound
layer
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Korean (ko)
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하재승
윤준
이재탁
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주식회사 엘지화학
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Priority claimed from KR1020180088195A external-priority patent/KR102075732B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880011802.9A priority Critical patent/CN110291077B/zh
Publication of WO2019054634A1 publication Critical patent/WO2019054634A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • an organic light emitting phenomenon is a phenomenon in which an organic material is used to convert electric energy into light energy.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, quick response time, and has been studied much because of its excellent luminance, driving voltage, and quick 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 material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826 [Description of the Invention]
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • Y < 2 &gt are each independently hydrogen; Substituted or unsubstituted d- 40 alkyl; Substituted or unsubstituted C 6 -C 60 aryl; Or a substituted or unsubstituted C 2 - 60 heteroaryl containing at least one of O, N, Si and S,
  • An and Ar 2 are each C independently represents a substituted or unsubstituted 6-60 aryl; Substituted or unsubstituted . 0, N, C 2 containing Si and S 1 or more of 60, or heteroaryl, or ⁇ ⁇ ⁇ to Ar 4 is a group bonded to adjacent to each other to form a condensed ring,
  • Li to L < 3 > are each independently a direct bond; Substituted or unsubstituted C 6 - 60 arylene; Or C 2 - 60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O, S and Si,
  • Ri to R < 3 &gt are each independently hydrogen; heavy hydrogen; halogen; Time to come; Cyano; Nitrile; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; Substituted or Unsubstituted d-60 haloalkyl; Substituted or unsubstituted d- 60 thioalkyl; Substituted or unsubstituted C w alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C 3 - 60 cycloalkyl; Substituted or unsubstituted d-60 alkenyl; Substituted or unsubstituted C 6 -C 60 aryl; Substituted or unsubstituted C 6 -C 60 aryloxy; Or a substituted or unsubstituted C 2 -
  • n is from 0 to 4
  • 0 0 to 2
  • n is from 0 to 3
  • the present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.
  • the compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device.
  • the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, and light emitting material.
  • Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
  • FIG. 2 is a sectional view of a light emitting device according to a first embodiment of the present invention which comprises a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a hole adjusting layer 7, a light emitting layer 8, an electron transporting layer 9, And shows an example of an organic light emitting device.
  • the present invention provides a compound represented by the above formula (1).
  • T denotes a bond connected to another substituent.
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsub
  • a substituent group to which at least two substituents are connected &quot may be a biphenyl group, that is, a biphenyl group may be an aryl group and may be interpreted as a substituent in which two phenyl groups are connected. But it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure,
  • the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms.
  • a compound of the following structure is not particularly limited, but is preferably 1 to 25 carbon atoms.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. Another According to the embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- Pentyl, neopentyl, tert-pentyl, n-butyl, n-butyl, 1-methylpentyl, 2-methylpentyl, N-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like.
  • the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms.
  • the cycloalkyl group has 3 to 6 carbon atoms.
  • Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • the 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. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klycenyl,
  • a 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 heterocyclic group is a heterocyclic group containing at least one of O, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a pyridine group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, an isoquinoline group, an indole group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, A benzoimidazole group, a benzothiazole group, a benzoxazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group,
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.
  • the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.
  • the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
  • the description of the aryl group described above can be applied except that arylene is a divalent group.
  • the description of the above-mentioned heterocyclic group except that the heteroarylene is divalent can be applied.
  • the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other.
  • the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
  • the formula (1) may be any one selected from compounds represented by the following formulas (1-1) to (1-12).
  • Li, and L < 3 > are each independently a direct bond; Substituted or unsubstituted C 6 - 60 arylene; Or C 2 - 60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O, S and Si,
  • An and Ar 2 are each C independently represents a substituted or unsubstituted 6-60 aryl; Substituted or unsubstituted 0, N, C 2, including one or more of Si and S ring-or 60 heteroaryl, or ⁇ ⁇ to Ar 4 may form a condensed ring by combining groups that are adjacent to each other.
  • a and Ar 2 are each independently selected from the group consisting of
  • L 3 and L 3 are each independently selected from the group consisting of
  • the compound represented by the formula (1) may be any one selected from the group consisting of
  • the compound represented by the formula (1) can be prepared by the same method as in the following reaction formula (1).
  • the above production method can be more specific in the production example to be described later.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention provides a display device comprising: a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked . have.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a hole controlling layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.
  • the organic material layer may include a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, or a hole controlling layer, and the hole injecting layer, the hole transporting layer, the hole injecting and transporting layer,
  • the hole-controlling layer includes the compound represented by the above formula (1).
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
  • the organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer may include an electron transporting layer,
  • the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound represented by the above formula (1).
  • the organic material layer may include a light emitting layer and a hole transporting layer, and the major transporting layer may include a compound represented by the general formula (1).
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • FIGS. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • FIG. 2 is a schematic view of a light emitting device according to a first embodiment of the present invention which comprises a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a hole adjusting layer 7, a light emitting layer 8, an electron transporting layer 9, And shows an example of an organic light emitting device.
  • the compound represented by Formula 1 may be included in at least one of the hole injection layer, the hole transport layer, the hole control layer, the light emitting layer, and the electron transport layer.
  • the organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
  • the organic light emitting diode when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention can be manufactured by sequentially laminating a gate electrode, an organic material layer, and a second electrode on a substrate.
  • a metal oxide or a metal oxide having conductivity or an alloy thereof may be formed on the substrate using a PVDCphys i cal Vapor Deposition method such as a sputtering method or an e-beam evaporation method
  • a hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a substance usable as a cathode is deposited thereon.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, coating, and the like. But is not limited thereto.
  • an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 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 and the second electrode is a cathode.
  • the anode material a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (II), indium zinc oxide (IZO); ⁇ 0: ⁇ 1 SN0 or 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] (PEDOT), polypyrrole and polyaniline, no.
  • the negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO 2 / Al, but the present invention is not limited thereto.
  • the hole injecting material is a layer for injecting holes from the electrode.
  • the hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material.
  • a compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable.
  • the highest occupied molecular orbital (H0M0) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include The organic material may be selected from the group consisting of metal porphyrin, oligothiophene, arylamine-based organic materials, nuclear nitrile-tetracyclopentene-based organic materials, quinacridone-based organic materials, perylene- And conductive polymers such as polyaniline and polythiophene series, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material.
  • a hole transport material Is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but the present invention is not limited thereto.
  • the light emitting material may be a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative examples include pyrene, anthracene, chrysene, and ferriflantene having an arylamino group.
  • the styrylamine compound examples include substituted or unsubstituted arylamine having at least one A substituted or unsubstituted aryl group, an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group.
  • the electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, iterbum and samarium, in each case followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, 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- (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] (2-methyl-8-quinolinato) gallium, bis (2-methyl-8-quinolinato) (2-methyl-8-quinolinato) (2-naphthalato) gallium, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-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 an organic light emitting device.
  • the preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. Production Example 1
  • the organic layer was dried over anhydrous magnesium sulfate, and the residue was distilled under reduced pressure, and the residue was recrystallized from ethyl acetate and a nucleic acid to obtain 29.63 g of the compound Al-2 (85.6 g, 85%) as a colorless oil. %).
  • Compound B1-2 was synthesized by the same method except that B1-1 was used instead of A1-1 in the synthesis of A1
  • Compound B1-3 was synthesized by the same method except that B1-2 was used instead of A1-2 in the synthesis of Al
  • Compound B2-1 was synthesized by the same method except that B1-3 was used instead of A1-3 in the synthesis of A2-1
  • A3-2 was prepared by synthesizing A2-3 instead of A2-1 and using 4-chlorophenylboronic acid instead of 3-chlorophenylboronic acid in the synthesis of A3-1 above
  • A2-3 A3-3 Synthesis was carried out in the same manner as in A3-1 except that A2-3 was used instead of A2-1 and 2-chlorophenylboronic acid was used instead of 3-chlorophenylboronic acid to obtain A3- 3 was prepared
  • A3-4 A3-4 was synthesized in the same manner as above except that A2-4 was used instead of A2-1 in the synthesis of A3-1 above
  • A3-5 A3-5 was synthesized by the same method except that A2-4 was used instead of A2-2 in the synthesis of A4-1 above
  • B2-B3-The synthesis of A3-1 above was repeated except that B2-1 was used instead of A2-1, and 4-chlorophenylboronic acid was used instead of 3-chlorophenylboronic acid to obtain B3-1 .
  • B3-3 was prepared by the same method except for using 2-chlorophenylboronic acid.
  • B3-4 was synthesized by the same method except for using B2-4 instead of A2- .2 in the synthesis of A4-1
  • A2-3 Compound 5 was prepared by the same method except that A2-3 was used instead of A2-1 in the synthesis of Compound 1 above.
  • A3- 17 A3-1 was used in place of A2-1 in the synthesis of Compound 1, and N-phenyl- [l, l ' -biphenyl] -4-amine was used to prepare Compound 17
  • A3-2 was used in place of A2-1 in the synthesis of the compound 1, a di ([1,1'-biphenyl] -
  • a glass substrate (corning 7059 glass) coated with a thin film of 1,000 A thick indium tin oxide was placed in distilled water containing a dispersant and washed with ultrasonic waves.
  • the detergent was a product of Fischer Co.
  • the distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. For 30 minutes After washing, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
  • a hexagonal nitrile hexaazatriephenylenene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer.
  • Compound 1 synthesized in Preparation Example 4-1 which is a hole transporting material on the hole injection layer was vacuum deposited to a thickness of 900 A to form an optically active transport layer.
  • HT2 was vacuum-deposited on the hole transport layer to a thickness of 50 A To form a hole control layer.
  • host HI and a dopant D1 compound (25: 1) were vacuum deposited on the hole-transporting layer to a thickness of 300 A as a light emitting layer.
  • an E1 compound was vacuum deposited on the light emitting layer to a thickness of 300 A to form an electron transporting layer.
  • an organic light emitting device was produced.
  • the deposition rate of organic material was maintained at a rate of 1 / sec
  • the deposition rate of lithium fluoride was 0.2 A / sec
  • the deposition rate of aluminum was 3 to 7 A / sec.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the compound described in Table 1 was used instead of Compound 1 as the hole transporting layer.
  • the current, 20 mA / cm 2 was applied to the organic light emitting devices prepared in Examples 1 to 20 and Comparative Examples 1 to 3 to measure voltage, efficiency, color coordinates and lifetime.
  • ITO Indium Tin Oxide
  • the substrate corning 7059 glass
  • the detergent was a product of Fischer Co.
  • the distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used.
  • ITO was washed for 30 minutes and then ultrasonically washed for 2 minutes with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
  • a hexagonal nitrile hexaazatriephenylenene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer.
  • a hole transport layer was formed by vacuum evaporation of a hole transport layer (HT), which is a material for transporting holes, to a thickness of 900 A.
  • HT hole transport layer
  • a host HI and a dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 A as a compound emitting layer.
  • an electron transport layer was formed by thermally vacuum depositing an E1 compound on the light emitting layer to a thickness of 300 A, and then lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2,000 A were sequentially deposited on the electron transport layer to form a cathode To prepare an organic light emitting device.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 1 A / sec
  • the deposition rate of lithium fluoride was 0.2 A / sec
  • the deposition rate of aluminum was 3 to 7 A / sec.
  • the current, current (20 mA / cm 2 ) was applied to the organic light emitting devices prepared in Examples 21 to 42 and Comparative Examples 4 to 8 to measure voltage, efficiency, color coordinates and lifetime.
  • Example 37 Compound 21 3.88 6.23 (0.135, 0.138) 54.2
  • Example 38 Compound 22 3.72 6.1 (0.133, 0.139) 55.2
  • Example 39 Compound 23 3.65 5.98 (0.135, 0.138) 51.8
  • the compound represented by the chemical formula according to the present invention can function as a hole transporting and hole controlling in an organic electronic device including an organic light emitting device. And that it exhibits excellent properties in terms of stability.

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

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un dispositif électroluminescent organique l'utilisant.
PCT/KR2018/008986 2017-09-12 2018-08-07 Nouveau composé hétérocylique et dispositif électroluminescent organique utilisant celui-ci WO2019054634A1 (fr)

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WO2021080334A1 (fr) * 2019-10-23 2021-04-29 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé

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JP2006339577A (ja) * 2005-06-06 2006-12-14 Konica Minolta Holdings Inc 有機半導体薄膜及び有機薄膜トランジスタ
WO2009148015A1 (fr) * 2008-06-05 2009-12-10 出光興産株式会社 Composé halogéné, composé polycyclique, et élément électroluminescent organique comprenant le composé polycyclique
KR20120103551A (ko) * 2009-06-30 2012-09-19 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR20130064601A (ko) * 2011-12-08 2013-06-18 주식회사 두산 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
CN106279055A (zh) * 2015-05-12 2017-01-04 上海和辉光电有限公司 一种茚并杂代蒽化合物及其应用

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KR101537005B1 (ko) * 2012-09-28 2015-07-20 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치

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JP2006339577A (ja) * 2005-06-06 2006-12-14 Konica Minolta Holdings Inc 有機半導体薄膜及び有機薄膜トランジスタ
WO2009148015A1 (fr) * 2008-06-05 2009-12-10 出光興産株式会社 Composé halogéné, composé polycyclique, et élément électroluminescent organique comprenant le composé polycyclique
KR20120103551A (ko) * 2009-06-30 2012-09-19 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR20130064601A (ko) * 2011-12-08 2013-06-18 주식회사 두산 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
CN106279055A (zh) * 2015-05-12 2017-01-04 上海和辉光电有限公司 一种茚并杂代蒽化合物及其应用

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021080334A1 (fr) * 2019-10-23 2021-04-29 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé

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