WO2019054634A1 - Novel heterocyclic compound and organic light-emitting device using same - Google Patents

Novel heterocyclic compound and organic light-emitting device using same 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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PCT/KR2018/008986
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French (fr)
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/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880011802.9A priority Critical patent/CN110291077B/en
Publication of WO2019054634A1 publication Critical patent/WO2019054634A1/en

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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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Abstract

The present invention provides a novel heterocyclic compound and an organic light-emitting device using same.

Description

【발명의 명칭】  Title of the Invention
신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자  Novel heterocyclic compounds and organic light emitting devices using the same
【기술분야】 TECHNICAL FIELD
관련 출원 (들)과의 상호 인용 Cross-reference with related application (s)
본 출원은 2017년 9월 12일자 한국 특허 출원 제 10-2017-0116821호， 및 2018년 7월 27일자 한국 특허 출원 제 10-2018-0088195호에 기초한 우선권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다.  This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0116821 filed on September 12, 2017, and Korean Patent Application No. 10-2018-0088195 filed on July 27, 2018, All of which are incorporated herein by reference.
본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.  The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
【발명의 배경이 되는 기술】 TECHNICAL BACKGROUND OF THE INVENTION
' 일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각， 우수한 콘트라스트, 빠른 응답 시간을 가지며， 휘도， 구동 전압 및 웅답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며， 예컨대 정공주입층， 정공수송층， 발광층， 전자수송층， 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이， 음극에서는 전자가 유기물층에 주입되게 되고， 주입된 정공과 전자가 만났을 때 액시톤 (exci ton)이 형성되며， 이 액시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다. 【선행기술문헌】 ' Generally, 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. For example, 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. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, and an exciton is formed when the injected holes and electrons meet each other. The light is emitted when the axon falls back to the floor. There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices. [Prior Art Document]
【특허문헌】  [Patent Literature]
(특허문헌 0001) 한국특허 공개번호 제 10-2000-0051826호 【발명의 내용】  [Patent Document 0001] Korean Patent Publication No. 10-2000-0051826 [Description of the Invention]
【해결하고자 하는 과제】  [Problem to be solved]
본 발명은 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. 【과제의 해결 수단】  The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same. MEANS FOR SOLVING THE PROBLEMS
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.  The present invention provides a compound represented by the following formula (1).
Figure imgf000003_0001
Figure imgf000003_0001
상기 화학식 1에서，  In Formula 1,
^ 및 Y2는 각각 독립적으로 수소; 치환 또는 비치환된 d-40 알킬; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 0 , N , Si 및 S 중 1개 이상을 포함하는 C2— 60 헤테로아릴이고， And Y < 2 > 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 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된. 0， N , Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로아릴이거나， 또는 ΑΓ ι 내지 Ar4는 서로 인접하는 기와 결합하여 축합 고리를 형성하고, 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 Α Γ ι to Ar 4 is a group bonded to adjacent to each other to form a condensed ring,
Li 내지 L3은 각각 독립적으로 직접 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 N , 0， S 및 Si로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로 원자를 포함하는 C2-60 헤테로아릴렌이고， 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 내지 R3은 각각 독립적으로 수소; 중수소; 할로겐; 히도록시기; 시아노; 니트릴; 니트로; 아미노; 치환 또는 비치환된 d— 60 알킬; 치환 또는 비치환된 d-60 할로알킬 ; 치환 또는 비치환된 d-60 티오알킬 ; 치환 또는 비치환된 Cwo 알콕시 ; 치환 또는 비치환된 d-60 할로알콕시 ; 치환 또는 비치환된 C3-60 사이클로알킬 ; 치환 또는 비치환된 d-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C6-60 아릴옥시; 또는 치환 또는 비치환된 0， N, Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로아릴이고， Ri to R < 3 > 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 - 60 heteroaryl containing at least one of O, N, Si and S,
m은 0 내지 4이고，  m is from 0 to 4,
0는 0 내지 2이고,  0 is 0 to 2,
n은 0 내지 3이고，  n is from 0 to 3,
z는 1 내지 4이고， 단, n+z는 4 이하이다. 또한， 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 게 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는， 유기 발광 소자를 제공한다.  z is from 1 to 4, provided that n + z is not greater than 4. 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.
【발명의 효과】 【Effects of the Invention】
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며， 유기 발광 소자에서 효율의 향상， 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 특히， 상술한 화학식 1로 표시되는 화합물은 정공주입， 정공수송, 정공주입 및 수송， 발광 재료로 사용될 수 있다.  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. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, and light emitting material.
【도면의 간단한 설명】 BRIEF DESCRIPTION OF THE DRAWINGS
도 1은 기판 (1)， 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.  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.
도 2는 기판 ( 1)， 양극 (2)， 정공주입층 (5)， 정공수송층 (6)， 정공조절층 (7)， 발광층 (8)， 전자수송층 (9) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.  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.
【발명을 실시하기 위한 구체적인 내용】 DETAILED DESCRIPTION OF THE INVENTION
이하， 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다. 본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention. The present invention provides a compound represented by the above formula (1).
본 명세서에서， ： 및 丁는 다른 치환기에 연결되는 결합을 의미한다. 본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기 ; 히드록시기; 카보닐기; 에스테르기 ; 이미드기 ; 아미노기 ; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, 0 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나， 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대， "2 이상의 치환기가 연결된 치환기' '는 비페닐기일 수 있다. 즉ᅳ 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나ᅳ In the present specification,: and T denotes a bond connected to another substituent. As used herein, the term " 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 unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, " a substituent group to which at least two substituents are connected " 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,
Figure imgf000005_0001
본 명세서에 있어서， 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄， 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로， 하기 구조식의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.
Figure imgf000005_0001
In the present specification, 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.
Figure imgf000006_0001
본 명세서에 있어서， 이미드기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이
Figure imgf000006_0001
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, a compound of the following structure
Figure imgf000006_0002
본 명세서에 있어서， 실릴기는 구체적으로 트리메틸실릴기， 트리에틸실릴기， t-부틸디메틸실릴기， 비닐디메틸실릴기， 프로필디메틸실릴기， 트리페닐실릴기， 디페닐실릴기， 페닐실릴기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 붕소기는 구체적으로 트리메틸붕소기， 트리에틸붕소기， t-부틸디메틸붕소기， 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 할로겐기의 예로는 불소， 염소， 브롬 또는 요오드가 있다. 본 명세서에 있어서， 상기 알킬기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸， 프로필， n-프로필， 이소프로필， 부틸， n-부틸， 이소부틸， tert-부틸， sec-부틸， 1-메틸-부틸， 1_에틸-부틸， 펜틸， n-펜틸， 이소펜틸， 네오펜틸， tert-펜틸， 핵실， n-핵실， 1-메틸펜틸， 2-메틸펜틸， 4-메틸 -2-펜틸， 3 , 3-디메틸부틸， 2-에틸부틸， 헵틸， n-헵틸， 1-메틸핵실， 사이클로펜틸메틸， 사이클로핵틸메틸， 옥틸, n-옥틸， tert-옥틸， 1-메틸헵틸， 2-에틸헥실， 2- 프로필펜틸， n-노닐, 2 , 2-디메틸헵틸， 1-에틸-프로필， 1 , 1-디메틸-프로필， 이소핵실， 2-메틸펜틸， 4-메틸핵실， 5-메틸핵실 등이 있으나， 이들에 한정되지 않는다. 본 명세서에 있어서， 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나， 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐， 이소프로페닐， 1-부테닐， 2-부테닐， 3-부테닐， 1-펜테닐， 2-펜테닐， 3-펜테닐， 3-메틸 -1-부테닐， 1， 3-부타디에닐, 알릴， 1-페닐비닐 -1- 일， 2-페닐비닐— 1-일, 2，2-디페닐비닐— 1-일， 2-페닐 -2- (나프틸 -1-일)비닐 -1-일， 2，2-비스 (디페닐 -1-일)비닐 -1-일， 스틸베닐기， 스티레닐기 등이 있으나 이들에 한정되지 않는다. 본 명세서에 있어서， 사이클로알킬기는 특별히 한정되지 않으나， 탄소수 3 내지 60인 것이 바람직하며， 일 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필， 사이클로부틸, 사이클로펜틸， 3-메틸사이클로펜틸， 2，3-디메틸사이클로펜틸， 사이클로핵실， 3-메틸사이클로핵실， 4-메틸사이클로핵실， 2 , 3- 디메틸사이클로핵실， 3，4，5-트리메틸사이클로핵실， 4-tert-부틸사이클로핵실, 사이클로헵틸， 사이클로옥틸 등이 있으나， 이에 한정되지 않는다. 본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며 , 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기， 바이페닐기， 터페닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기， 안트라세닐기， 페난트릴기, 파이레닐기， 페릴레닐기， 크라이세닐기， 플루오레닐기 등이 될 수 있으나 이에 한정되는 것은 아니다. 본 명세서에 있어서， 플루오레닐기는 치환될 수 있고， 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우，
Figure imgf000006_0002
In the present specification, 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. In the present specification, 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. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine. In the present specification, 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. Specific examples of the alkyl group 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. In the present specification, 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. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl- (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like. In the present specification, 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. According to another embodiment, 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. In the present specification, 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. Examples of the polycyclic aryl group include, but are not limited to, naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klycenyl, In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
Figure imgf000008_0001
Figure imgf000008_0001
등이 될 수 있다. 다만， 이에 한정되는 것은 아니다. 본 명세서에 있어서， 헤테로고리기는 이종 원소로 0， Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서， 탄소수는 특별히 한정되지 않으나， 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기， 피를기， 이미다졸기， 티아졸기， 옥사졸기 , 옥사디아졸기， 트리아졸기， 피리딜기， 비피리딜기， 피리미딜기， 트리아진기， 아크리딜기， 피리다진기， 피라지닐기ᅳ 퀴놀리닐기， 퀴나졸린기, 퀴녹살리닐기， 프탈라지닐기， 피리도 피리미디닐기， 피리도 피라지닐기, 피라지노 피라지닐기， 이소퀴놀린기， 인돌기， 카바졸기, 벤조옥사졸기， 벤조이미다졸기， 벤조티아졸기， 벤조카바졸기 벤조티오펜기， 디벤조티오펜기， 벤조퓨라닐기， 페난쓰롤린기 (phenanthrol ine) , 이소옥사졸릴기, 티아디아졸릴기， 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 마니다. 본 명세서에 있어서， 아르알킬기， 아르알케닐기， 알킬아릴기， 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서， 아르알킬기， 알킬아릴기， 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서， 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서， 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 .설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 바람직하게는， 상기 화학식 1은 하기 화학식 1-1 내지 1-12로 표시되는 화합물 중에서 선택되는 어느 하나일 수 있다. And the like. However, the present invention is not limited thereto. In the present specification, 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. Examples of the heterocyclic group 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, A benzoimidazole group, a benzothiazole group, a benzoxazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, a thio group, A thiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto It's Mani. In the present specification, 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. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group. In this specification, the description of the above-mentioned heterocyclic group except that the heteroarylene is divalent can be applied. In the present specification, 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. In the present specification, 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. Preferably, the formula (1) may be any one selected from compounds represented by the following formulas (1-1) to (1-12).
Figure imgf000009_0001
Figure imgf000009_0001
[화학식 1-3]
Figure imgf000010_0001
[Formula 1-3]
Figure imgf000010_0001
[화학식 1-4] [Formula 1-4]
、1 ,One
Ar: Ar :
[화학식 1-5]  [Formula 1-5]
Ar-ι  Ar-ι
、1 ,One
Ar; Ar ;
Figure imgf000010_0002
Figure imgf000010_0002
[화학식 1-8]
Figure imgf000011_0001
[Chemical Formula 1-8]
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000012_0001
상기 화학식 l-l 내지 1-12에서，  In the above formulas (1-1) to (1-12)
Li , 및 L3은 각각 독립적으로 직접 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 N, 0， S 및 Si로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로 원자를 포함하는 C2-60 헤테로아릴렌이고， 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 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 0， N, Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로아릴이거나， 또는 Αι^ 내지 Ar4는 서로 인접하는 기와 결합하여 축합 고리를 형성할 수 있다. 바람직하께는， A 및 Ar2는 각각 독립적으로 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다. 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 Αι ^ to Ar 4 may form a condensed ring by combining groups that are adjacent to each other. Preferably, A and Ar 2 are each independently selected from the group consisting of
Figure imgf000013_0001
Figure imgf000013_0001
 
Figure imgf000014_0001
Figure imgf000014_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000015_0001
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000017_0001
Figure imgf000017_0002
Figure imgf000017_0002
Figure imgf000017_0003
Figure imgf000017_0003
¾은 각각 독립적으로 수소; 중수소; 할로겐; 시아노; 니트릴; 니트로; 아미노; 치환 또는 비치환된 d-60 알킬 ; 치환 또는 비치환된 d-60 할로알킬 ; 치환 또는 비치환된 d-60 알콕시 ; 치환 또는 비치환된 d-60 할로알콕시 ; 치환 또는 비치환된 C3-60 사이클로알킬 ; 치환 또는 비치환된 d-60 알케닐; 치환 또 는 비치환된 C6-60 아릴 ; 치환 또는 비치환된 C6-60 아릴옥시 ; 또는 치환 또는 비치환된 0， N, Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로아릴일 수 있다. 바람직하게는， 내지 L3은 각각 독립적으로 하기로 구성되는 군으로 부터 선택되는 어느 하나일 수 있다. Each independently represents hydrogen; heavy hydrogen; halogen; Cyano; Nitrile; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d- 60 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 - 60 aryl; Substituted or unsubstituted C 6 -C 60 aryloxy; Or a substituted or unsubstituted C 2 -C 60 heteroaryl containing one or more of O, N, Si and S; Preferably, L 3 and L 3 are each independently selected from the group consisting of
Figure imgf000018_0001
바람직하게는， 상기 화학식 1로 표시되는 화합물은， 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다.
Figure imgf000018_0001
Preferably, the compound represented by the formula (1) may be any one selected from the group consisting of
Figure imgf000019_0001
Figure imgf000019_0001
 
Figure imgf000020_0001
Figure imgf000020_0001
 
Figure imgf000021_0001
Figure imgf000021_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV /// O 9868008ϊ02Μ1><ί6SZA 986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000022_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000023_0001
22 /// O 9868008ϊ02Μ1><ί6SZA 22 /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000024_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000026_0001
 /// O 9868008ϊ02Μ1><ί6SZA  /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000027_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000028_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000029_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000032_0001
986800/8l0raM/13d 986800 / 8l0raM / 13d
Figure imgf000033_0001
Figure imgf000033_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV 986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV
Figure imgf000034_0001
Figure imgf000034_0001
33 //:/ O 9868008ϊ02χΙ22so6sAV 33 // : / O 9868008ϊ02χΙ22so 6 sAV
Figure imgf000035_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000036_0001

Figure imgf000037_0001

Figure imgf000037_0001
Figure imgf000038_0001
9ε
Figure imgf000038_0001
9?
Figure imgf000039_0001
Figure imgf000039_0001
986800/8l0ZHM/13d 9l7S0/6I0Z OAV 986800 / 8l0ZHM / 13d 9l7S0 / 6I0Z OAV
O/6SZAV S9/:£/s2Ml 9868008 O / 6SZAV S9 /: £ / s2M l 986800 8
Figure imgf000040_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000041_0001
40 //:/ O8ϊ02Μ12 i2iso6szAV77 40 //: / O 8i0 2M12 i 2 i so 6 s z AV 77
Figure imgf000042_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000044_0001
43
Figure imgf000045_0001
43
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000046_0001
 
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV
Figure imgf000048_0001
986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000049_0001
986800/81 Oia¾/X3d :9tS0/6I0Z: OAV 986800/81 Oia¾ / X3d: 9tS0 / 6I0Z: OAV
Figure imgf000050_0001
Figure imgf000050_0001

Figure imgf000051_0001
L9 
Figure imgf000051_0001
L9
Figure imgf000052_0001
Figure imgf000052_0001
986800/8ΪΟΖΗΝ/Χ3<Ι ^£9fS0/6l0Z OAV /8ΐ02¾/:>1¾ 986800 / 8ΪΟΖΗΝ / Χ3 <Ι ^ £ 9fS0 / 6l0Z OAV / 8 ΐ 02¾ /:> 1¾
Figure imgf000053_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000054_0001
力 Force
Figure imgf000055_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000056_0001
SO/SOZ ΟΛ\ SO / SOZ ΟΛ \
Figure imgf000057_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000058_0001
986800/8l0ZHM/X3d OAV /// O 9868008ϊ02Μ1><ί6SZA 986800 / 8l0ZHM / X3d OAV /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000059_0001
Figure imgf000059_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000060_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000062_0001
61 29 61 29
Figure imgf000063_0001
Figure imgf000063_0001
986800/8I0Za¾/X3d 986800 / 8I0Za¾ / X3d
^9^0/6103 OAV ^ 9 ^ 0/6103 OAV
Figure imgf000064_0001
Figure imgf000064_0001
63 //:/ O 9868008ϊ02Μ1κί6SZAV 63 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000065_0001
Figure imgf000065_0001
/¾l:>d 3l~s o^yw / ¾l: > d 3l ~ so ^ y w
Figure imgf000066_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000067_0001
66 //:/ O 9868008ϊ02Μ1κί6SZAV 66 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000068_0001
Figure imgf000068_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000069_0001
Figure imgf000069_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000070_0001
Figure imgf000070_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000071_0001
Figure imgf000071_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000072_0001
Figure imgf000072_0001
Figure imgf000073_0001
Figure imgf000073_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000074_0001
Figure imgf000074_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000075_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000079_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV
Figure imgf000080_0001
986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000081_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV
Figure imgf000082_0001
Figure imgf000083_0001
986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV
Figure imgf000082_0001
Figure imgf000083_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000084_0001
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000087_0001
86
Figure imgf000088_0001
86
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000089_0001
88 88
Figure imgf000090_0001
Figure imgf000090_0001
Figure imgf000090_0002
Figure imgf000091_0001
Figure imgf000090_0002
Figure imgf000091_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000092_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000093_0001
Figure imgf000094_0001
//:/ O 9868008ϊ02Μ1κί6SZAV
Figure imgf000094_0001
// : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000095_0001
Figure imgf000095_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000096_0001
Figure imgf000096_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000097_0001
Figure imgf000097_0001
Figure imgf000098_0001
98/8/:6800s2Ml>d/ o2?6sz0/w.
Figure imgf000098_0001
98/8 / : 6800s2M l > d / o2? 6sz0 / w.
Figure imgf000099_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000100_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000101_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000103_0001
Figure imgf000103_0002
Figure imgf000103_0002
Figure imgf000103_0003
Figure imgf000103_0003
102
Figure imgf000104_0001
102
Figure imgf000104_0001
Figure imgf000105_0001
Figure imgf000105_0001
98680//08s2M:l2/S06S ΟZΜ. 98680 // 0 8 s2M : l 2 / S06S AUTO.
Figure imgf000106_0001
Figure imgf000106_0001
Figure imgf000107_0001
Figure imgf000107_0001
Figure imgf000108_0001
Figure imgf000109_0001
Figure imgf000108_0001
Figure imgf000109_0001
Figure imgf000110_0001
Figure imgf000110_0001
Figure imgf000111_0001
Figure imgf000111_0001
986800/810ΖΗΉ/Χ3<Ι ^£91^50/6101 Ο
Figure imgf000112_0001
986800 / 810ZZ / X3 < / RTI &gt;
Figure imgf000112_0001
8/s/:>d/ Ο 9680082M9fs06SZΛ 8 / s / : > d / Ο 96800 8 2M9fs06SZΛ
Figure imgf000113_0001
Figure imgf000113_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000114_0001
Figure imgf000114_0001
986/8008s2/:¾l2 i2iso/6si Ο... 986/800 8 s2 /: ¾ l 2 i 2 i so / 6 s i Ο ...
Figure imgf000115_0001
Figure imgf000115_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000116_0001
Figure imgf000116_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000117_0001
Figure imgf000117_0001
Figure imgf000118_0001
Figure imgf000118_0001
117 /8s2M/:l>d S9/i6si o/w 117 / 8 s2 M /: l> d S 9 / i6 s i o / w
Figure imgf000119_0001
Figure imgf000119_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000120_0001
Figure imgf000120_0001
Figure imgf000121_0001
Figure imgf000121_0001
20 20
Figure imgf000122_0001
Figure imgf000122_0001
Figure imgf000122_0002
Figure imgf000122_0002
Figure imgf000122_0003
Figure imgf000122_0003
121 121
Figure imgf000123_0001
Figure imgf000123_0001
ı22 I22
Figure imgf000124_0001
Figure imgf000124_0001
 
Figure imgf000125_0001
Figure imgf000125_0001
 
Figure imgf000126_0001
Figure imgf000126_0001
 
Figure imgf000127_0001
Figure imgf000127_0001
상기 화학식 1로 표시되는 화합물은 하기 반웅식 1과 같은 제조 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 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.
[반웅식 1] However,
Figure imgf000128_0001
Figure imgf000128_0001
Figure imgf000128_0002
Figure imgf000128_0002
상기 반웅식 1에서, Yi , Y2 , Li, L2, L3 , An 및 Ar2에 대한 설명은 상기 화학식 1에서 정의한 바와 같다. 한편， 상기 반웅식 1에서 X는 C1 또는 F이고， n은 1 내지 4일 수 있다. 상기 화학식 1로 표시되는 화합물은 상기 반웅식 1을 참고하여 제조하고자 하는 화합물의 구조에 맞추어 출발 물질을 적절히 대체하여 제조할 수 있다. 또한， 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로， 본 발명은 게 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. 본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나， 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 .있다. 예컨대， 본 발명의 유기 발광 소자는 유기물 충으로서 정공주입층， 정공수송층， 정공조절층， 발광층， 전자수송층， 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할수 있다. 또한， 상기 유기물 층은 정공주입층， 정공수송층， 정공 주입과 수송을 동시에 하는 층， 또는 정공조절층을 포함할 수 있고， 상기 정공주입층， 정공수송층, 정공 주입과 수송을 동시에 하는 층, 또는 정공조절층은 상기 화학식 1로 표시되는 화합물을포함한다. 또한， 상기 유기물 층은 발광층을 포함할 수 있고， 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한， 상기 유기물 층은 전자수송층, 또는 전자주입층을 포함할수 있고， 상기 전자수송층， 또는 전자주입층은상기 화학식 1로 표시되는 Banung in the formula (1), a description of Yi, Y 2, Li, L 2, L 3, An and Ar 2 are as defined in formula (I). On the other hand, in Equation 1, X may be C1 or F, and n may be 1 to 4. The compound represented by the formula (1) can be prepared by appropriately substituting the starting material in accordance with the structure of the compound to be prepared with reference to the above-mentioned Hanwoi 1. Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. For example, 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. For example, 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. However, 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). In addition, 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,
화합물을포함한다. 또한， 상기 전자수송층， 전자주입층， 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한， 상기 유기물 층은 발광층 및 정공수송층을 포함하고， 상기 전공수송층은 상기 화학식 1로 표시되는 화합물을 포함할수 있다. 또한, 본 발명에 따른 유기 발광 소자는， 기판상에 양극， 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판상에 음극， 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대， 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다. 도 1은 기판 ( 1)， 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 았다. 도 2는 기판 ( 1)， 양극 (2)， 정공주입층 (5)， 정공수송층 (6)， 정공조절층 (7) , 발광층 (8)， 전자수송층 (9) 및 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 정공주입층， 정공수송층， 정공조절층， 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 본 발명에 따른 유기 발광 소자는， 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우， 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. 예컨대， 본 발명에 따른 유기 발광 소자는 기판 상에 게 1 전극， 유기물층 및 제 2 전극올 순차적으로 적층시켜 제조할 수 있다. 이때， 스퍼터링법 (sput ter ing)이나 전자범 증발법 (e—beam evaporat ion)과 같은 PVDCphys i cal Vapor Depos i t ion)방법을 이용하여， 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고， 그 위에 정공 주입층， 정공 수송층， 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후， 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도， 기판 상에 음극 물질부터 유기물층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한， 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서， 용액 도포법이라 함은 스핀 코팅， 딥코팅， 닥터 블레이딩， 잉크젯 프린팅， 스크린 프린팅， 스프레이법， 를 코팅 등을 의미하지만， 이들만으로 한정되는 것은 아니다. 이와 같은 방법 외에도， 기판 상에 음극 물질로부터 유기물층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다 (W0 2003/012890) . 다만， 제조 방법이 이에 한정되는 것은 아니다. 일례로， 상기 제 1 전극은 양극이고, 상기 제 2 전극은 음극이거나， 또는 상기 제 1 전극은 음극이고， 상기 제 2 전극은 양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐， 크롬， 구리 , 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물， 인듐 산화물， 인듐주석 산화물 ( ΠΌ) , 인듐아연 산화물 ( IZ0)과 같은 금속 산화물; Ζη0:Α1 또는 SN02 :Sb와 같은 금속과 산화물의 조합; 폴리 (3- 메틸티오펜)， 폴리 [3 , 4- (에틸렌 -1 ,2-디옥시 )티오펜] (PED0T) , 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘， 칼슘， 나트륨， 칼륨， 티타늄， 인듐， 이트륨, 리튬， 가돌리늄， 알루미늄， 은， 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02/Al과 같은 다층 구조 물질 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 정공 주입 물질로는 전극으로부터 정공을 주입하는 층으로， 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과， 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고， 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며， 또한， 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 H0M0(highest occupi ed molecular orbi tal )가 양극 물질의 일함수와 주변 유기물 층의 HOMO사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린 (porphyr in) , 올리고티오펜, 아릴아민 계열의 유기물， 핵사니트릴핵사아자트리페닐렌 계열의 유기물， 퀴나크리돈 (quinacr idone)계열의 유기물， 페릴렌 (perylene) 계열의 유기물， 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나， 이들에만 한정 되는 것은 아니다. 상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로， 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물， 전도성 고분자， 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 둥이 있으나， 이들에만 한정되는 것은 아니다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 밫을 낼 수 있는 물질로서， 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물 (Al ) ; 카르바졸 계열 화합물; 이량체화 스티릴 (dimer i zed styryl ) 화합물; BAlq; 10-히드록시벤조 퀴놀린- 금속 화합물; 벤족사졸， 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리 (P- 페닐렌비닐렌) (PPV) 계열의 고분자; 스피로 (spi ro) 화합물; 폴리플루오렌， 루브렌 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체， 피렌 유도체， 나프탈렌 유도체， 펜타센 유도체， 페난트렌 화합물， 플루오란텐 화합물 등이 있고， 헤테로환 함유 화합물로는 카바졸 유도체， 디벤조퓨란 유도체， 래더형 퓨란 화합물， 피리미딘 유도체 등이 있으나， 이에 한정되지 않는다. 도펀트 재료로는 방향족 아민 유도체， 스트릴아민 화합물， 붕소 착체， 플루오란텐 화합물， 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서， 아릴아미노기를 갖는 피렌， 안트라센， 크리센， 페리플란텐 등이 있으며， 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로， 아릴기， 실릴기， 알킬기， 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민， 스티릴디아민， 스티릴트리아민， 스티릴테트라아민 등이 있으나， 이에 한정되지 않는다. 또한， 금속 착체로는 이리듐 착체， 백금 착체 등이 있으나， 이에 한정되지 않는다. 상기 전자 수송 물질로는 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서， 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 A1 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본 -금속 착물 등이 있으나， 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히， 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘， 바륨， 칼슘， 이테르붐 및 사마륨이고， 각 경우 알루미늄 층 또는 실버층이 뒤따른다. 상기 전자주입층은 전극으로부터 전자를 주입하는 층으로， 전자를 수송하는 능력을 갖고， 음극으로부터의 전자 주입 효과， 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며， 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한， 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄， 다이페노퀴논， 티오피란 다이옥사이드， 옥사졸， 옥사다이아졸， 트리아졸， 이미다졸， 페릴렌테트라카복실산， 프레오레닐리덴 메탄， 안트론 등과 그들의 유도체， 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나， 이에 한정되지 않는다. 상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스 (8- 하이드록시퀴놀리나토)아연， 비스 (8-하이드록시퀴놀리나토)구리， 비스 (8- 하이드록시퀴놀리나토)망간， 트리스 (8-하이드록시퀴놀리나토)알루미늄, 트리스 (2-메틸 -8-하이드록시퀴놀리나토)알루미늄， 트리스 (8- 하이드록시퀴놀리나토)갈륨， 비스 (10-하이드록시벤조 [h]퀴놀리나토)베릴륨， 비스 (10-하이드록시벤조 [h]퀴놀리나토)아연， 비스 (2-메틸 -8- 퀴놀리나토)클로로갈륨， 비스 (2-메틸 -8-퀴놀리나토) ( 0-크레졸라토)갈륨， 비스 (2-메틸 -8-퀴놀리나토 ) (1-나프를라토)알루미늄， 비스 (2-메틸 -8- 퀴놀리나토) (2-나프를라토)갈륨 등이 있으나, 이에 한정되지 않는다. 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형， 후면 발광형 또는 양면 발광형일 수 있다. 또한， 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다. 상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다. 제조예 1 &Lt; / RTI &gt; Further, 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). In addition, 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. In addition, 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. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in 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. Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. 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. In such a structure, 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). In addition, 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. For example, 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. In this case, 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. In addition to such a method, 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. In addition, 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. Here, 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. In addition to such a method, 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). However, the manufacturing method is not limited thereto. In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is a cathode. As 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. Specific examples of 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); Ζη0: Α1 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. Specific examples of 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. It is preferable that 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. Specific examples of 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. 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. Specific examples include 8-hydroxy-quinoline aluminum complex (Al); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly (P-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto. 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. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, as the aromatic amine derivative Examples of the condensed aromatic ring derivative having a substituted or unsubstituted arylamino group include pyrene, anthracene, chrysene, and ferriflantene having an arylamino group. Examples of the styrylamine compound 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto. 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. In particular, an example of 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. Specific examples thereof include 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. In addition, 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
Figure imgf000134_0001
Figure imgf000134_0001
A1-1 A1-1
9, 9-디메틸 -9^플루오렌 -2-을 (150g, 713.3醒 ol )을 DMF(400ml )에 첨가하여 용해시킨 후 0°C에서 NBS(128.22 g, 720.4mraol )를 천천히 적가하고 실온에서 3 시간 동안 교반하였다. 상온에서 물과 클로로포름으로 추출한 후 흰색의 고체를 핵산으로 재결정하여 상기 화합물 Al-l(165g, 80%)을 제조하였다. (150 g, 713.3 mmol) was dissolved in DMF (400 ml) and then NBS (128.22 g, 720.4 mraol) was slowly added dropwise at 0 ° C and the mixture was stirred at room temperature And stirred for 3 hours. After extraction with water and chloroform at room temperature The white solid was recrystallized from a nucleic acid to give the above compound Al-1 (165 g, 80%).
MS[M+H]+= 290.17 MS [M + H] &lt; + &gt; = 290.17
Figure imgf000135_0001
Figure imgf000135_0001
질소 분위기에서 상기 화합물 Al-l(30g, 103.7mmol)( 비스 (피나콜라토)다이보론 (30.29g, 119.3mmol) 및 아세트산칼륨 (14.24g, 145.1mmol)을 섞고， 디옥산 (300ml)을 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스 (디벤질리딘아세톤)팔라듐 (1192mg, 0.02mol%)과 트리사이클로핵실포스핀 (1163mg, 0.04 mol%)을 넣고 3시간 동안 가열 및 교반하였다. 반웅 종료 후， 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고， 유기층을 무수황간마그네슘으로 건조하였다. 감압 증류 후 에틸아세테이트과 핵산으로 재결정하여 상기 화합물 Al-2 (29.63g, 85%)를 제조하였다. Mixing the compound Al-l (30g, 103.7mmol) ( bis (pinacolato) di boron (30.29g, 119.3mmol) and potassium acetate (14.24g, 145.1mmol) under nitrogen, was added to dioxane (300ml) (Dibenzylidineacetone) palladium (1192 mg, 0.02 mol%) and tricyclohexylphosphine (1163 mg, 0.04 mol%) were placed in a reflux condenser, and the mixture was heated and stirred for 3 hours. 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. %).
MS[M+H]+= 337.24 MS [M + H] &lt; + &gt; = 337.24
Figure imgf000135_0002
Figure imgf000135_0002
상기 화합물 Al-2(30g, 89.2隱01)를 2M 수산화나트륨 용액에 투입하고The above compound Al-2 (30 g, 89.2 mmol O 1) was added to a 2 M sodium hydroxide solution
0°C로 온도 안정화시킨 후 과산화수소 (30ml, 267.6mmol)를 교반하면서. 첨가하여 반웅을 완결하였다. 반응 종료 후， 물을 투입하여 30분간 교반 후 상온으로 은도를 낮춘 후 상기 화합물 Al-3( 17.15g, 85%)을 제조하였다. After stabilizing the temperature to 0 ° C, hydrogen peroxide (30 ml, 267.6 mmol) was added with stirring . To complete the reaction. After completion of the reaction, water was added and stirred for 30 minutes After lowering the silver concentration to room temperature, the above compound Al-3 (17.15 g , 85%) was prepared.
MS[M+H]+= 227.28 MS [M + H] &lt; + &gt; = 227.28
Figure imgf000136_0001
Figure imgf000136_0001
B1-1 B1-1
상기 A1-1의 합성에서 9， 9-디메틸 -9^플루오렌 -2-올 대신 9， 9-디페닐- 9 플루오렌 -2-올을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B1-1을 제조하였다  Synthesis was performed in the same manner as in the synthesis of the above A1-1 except that 9,9-diphenyl-9fluoren-2-ol was used instead of 9,9-dimethyl-9 ^ fluoren- 1 was prepared
MS[M+H]+= 414.31 MS [M + H] &lt; + &gt; = 414.31
Figure imgf000136_0002
상기 A1의 합성에서 A1-1 대신 B1-1을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B1-2를 제조하였다
Figure imgf000136_0002
Compound B1-2 was synthesized by the same method except that B1-1 was used instead of A1-1 in the synthesis of A1
MS[M+H]+= 461.38 제조예 1-6: B1-3의 합성 MS [M + H] &lt; + &gt; = 461.38 Preparation Example 1-6: Synthesis of B1-3
Figure imgf000137_0001
Figure imgf000137_0001
상기 Al의 합성에서 A1-2 대신 B1-2를 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B1-3을 제조하였다  Compound B1-3 was synthesized by the same method except that B1-2 was used instead of A1-2 in the synthesis of Al
MS[M+H]+= 351.42 제조예 2 MS [M + H] &lt; + &gt; = 351.42 Preparation 2
Figure imgf000137_0002
Figure imgf000137_0002
Al-3(30g, 132.5mmol ) , 4-브로모 -1 , 2-디플루오로벤젠 (25.82g, 133.8mmol ) 및 포타슘카보네이트 (51.17g, 265.1mmol )을 DMF(300ml )에 첨가하여 환류 교반시킨다. 반웅 완료 후 상온으로 식히고 필터한다. 상온에서 물과 클로로포름으로 추출한 후 흰색의 고체를 에틸아세테이트와 핵산으로 컬럼하여 상기 화합물 A2-l(15.7g, 35¾»)을 제조하였다. (25.82 g, 133.8 mmol) and potassium carbonate (51.17 g, 265.1 mmol) were added to DMF (300 ml) and refluxed with stirring . After completion of the reaction, cool to room temperature and filter. After extraction with water and chloroform at room temperature, the white solid was columned with ethyl acetate and nucleic acid to give the above compound A2-1 (15.7 g, 35.4 &gt;).
MS[M+H]+= 380.25 MS [M + H] &lt; + &gt; = 380.25
Figure imgf000137_0003
Figure imgf000137_0003
A1-3  A1-3
A2-2 상기 A2-1의 합성에서 컬럼으로 분리하여 화합물 A2-2를 제조하였다 MS[M+H]+= 380.25 제조예 2-3: A2— 3의 합성 A2-2 Compound A2-2 was prepared by separating into a column in the synthesis of A2-1 above. MS [M + H] + = 380.25 Preparation 2-3: Synthesis of A2-3
Figure imgf000138_0001
Figure imgf000138_0001
A1-3 A2-3  A1-3 A2-3
상기 A2-1의 합성에서 4-브로모 -1,2-디플루오로벤젠 대신 1-브로모- In the synthesis of the above A2-1, 1-bromo-1,2-difluorobenzene was used instead of 4-
2, 3-디플루오로벤젠을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 A2-3을 제조하였다 2, 3-difluorobenzene, the compound A2-3 was prepared
MS[M+H]+= 380.25 제조예 2-4: A2-4의 합성  MS [M + H] &lt; + &gt; = 380.25 Preparation 2-4: Synthesis of A2-4
Figure imgf000138_0002
Figure imgf000138_0002
상기 A2-3의 합성에서 컬럼으로 분리하여 화합물 A2-4를 제조하였다 MS[M+H]+= 380.25 Compound A2-4 was prepared by separating into a column in the synthesis of A2-3 above. MS [M + H] &lt; + &gt; = 380.25
Figure imgf000138_0003
Figure imgf000138_0003
A2-5  A2-5
A1-3  A1-3
상기 A2-1의 합성에서 4-브로모 -1,2-디플루오로벤젠 디클로로 -2，3-디플루오로벤젠을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 A2-5를 제조하였다 In the synthesis of the above A2-1, 4-bromo-1,2-difluorobenzene Dichloro-2,3-difluorobenzene, the compound A2-5 was prepared
MS[M+H]+= 370.24 MS [M + H] &lt; + &gt; = 370.24
Figure imgf000139_0001
Figure imgf000139_0001
상기 A2-5의 합성에서 1,2-디클로로 -4 ,5-디플루오로벤젠 대신 1,2- 디클로로 -4，5-디플루오로벤젠을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 A2-6을 제초하였다  Dichloro-4,5-difluorobenzene was used instead of 1,2-dichloro-4, 5-difluorobenzene in the synthesis of the above A2-5, the compound A2- 6 was weeded
MS[M+H]+= 370.24  MS [M + H] &lt; + &gt; = 370.24
Figure imgf000139_0002
Figure imgf000139_0002
상기 A2-1의 합성에서 A1-3 대신 B1-3을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B2— 1을 제조하였다  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
MS[M+H]+= 504.40 제조예 2-8: B2-2의 합성
Figure imgf000140_0001
MS [M + H] &lt; + &gt; = 504.40 Preparation Example 2-8: Synthesis of B2-2
Figure imgf000140_0001
B1-3  B1-3
B2-2  B2-2
상기 B2-1의 합성에서 컬럼으로 분리하여 화합물 B2-2를 제조하였다 MS[M+H]+= 504.40 제조예 2-9： B2-3의 합성 Compound B2-2 was prepared by separating into a column from the above synthesis of B2-1. MS [M + H] + = 504.40 Preparation Example 2-9: Synthesis of B2-3
Figure imgf000140_0002
Figure imgf000140_0002
B1-3 B2-3  B1-3 B2-3
상기 B2-1의 합성에서 4-브로모 -1 , 2-디플루오로벤젠 대신 1-브로모- In the synthesis of B2-1 above, 1-bromo-1,2-difluorobenzene was used instead of 4-bromo-
2，3-디플루오로벤젠을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B2-3을 제조하였다 2,3-difluorobenzene was used in place of 2,3-difluorobenzene, to thereby produce Compound B2-3
MS[M+H]+= 504.40 MS [M + H] &lt; + &gt; = 504.40
Figure imgf000140_0003
Figure imgf000140_0003
상기 B2-3의 합성에서 컬럼으로 분리하여 화합물 B2-4를 제조하였다 MS[M+H]+= 504.40 제조예 2-11: B2-5의 합성 Compound B2-4 was prepared by separating into a column in the synthesis of B2-3 above. MS [M + H] &lt; + &gt; = 504.40 Production example 2-11: Synthesis of B2-5
Figure imgf000141_0001
Figure imgf000141_0001
상기 B2-1의 합성에서 4-브로모 -1， 2-디플루오로벤젠 대신 1，4- 디클로로 -2 , 3-디플루오로벤젠을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B2-5를 제조하였다  Except that 1,4-dichloro-2,2,3-difluorobenzene was used in place of 4-bromo-1,2-difluorobenzene in the synthesis of B2-1 above to obtain Compound B2-5 Was prepared
MS[M+H]+= 494.38 MS [M + H] &lt; + &gt; = 494.38
Figure imgf000141_0002
Figure imgf000141_0002
상기 B2-5의 합성에서 1， 2-디클로로 -4， 5-디플루오로벤젠 대신 1，2- 디클로로 -4 , 5-디플루오로벤젠을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 B2-6을 제조하였다  Dichloro-4, 5-difluorobenzene was used instead of 1,2-dichloro-4, 5-difluorobenzene in the synthesis of B2-5 above to obtain Compound B2- 6 was prepared
MS[M+H]+= 494.38 제조예 3 MS [M + H] &lt; + &gt; = 494.38 Preparation 3
Figure imgf000141_0003
Figure imgf000141_0003
A2-1 A3-1 A2-l(20g, 52.7瞧01)과 3-클로로페닐보로닉산 (8.66g, 55.3mmol)을 테트라하이드로퓨란 (300ml)에 첨가한 후 2M 포타슘카보네이트 수용액 (150ml)을 첨가하고， 테트라키스트리페닐-포스피노팔라듐 (1.21g, 2mol¾ 를 넣은 후， 10시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반웅을 종결한 후 포타슘카보네이트 수용액을 제거하여 층분리하였다. 용매 제거 후 흰색의 고체를 에틸아세테이트로 재결정하여 상기 화합물 A3-K19.48 g, 수율 90%)을 제조하였다. A2-1 A3-1 A2-l (20g, 52.7瞧0 1) and 3-chlorophenyl view it followed by the addition of acid (8.66g, 55.3mmol) in tetrahydrofuran (300ml) was added 2M potassium carbonate aqueous solution (150ml) and tetrakis Triphenylphosphino palladium (1.21 g, 2mol) was added, and the mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature, the reaction mixture was terminated and the aqueous potassium carbonate solution was removed to separate the layers. Acetate to obtain 19.48 g of the above compound A3-K (yield 90%).
MS[M+H]+= 411.90  MS [M + H] &lt; + &gt; = 411.90
Figure imgf000142_0001
상기 A3-1의 합성에서 A2-1대신 A2-2를， 3—클로로페닐보로닉산 대신 4- 클로로페닐보로닉산을 사용한 것을 제외하고는 동일한 방법으로 합성하여 A3- 2를 제조하였다
Figure imgf000142_0001
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
MS[M+H]+= 411.90 MS [M + H] &lt; + &gt; = 411.90
Figure imgf000142_0002
Figure imgf000142_0002
질소 분위기에서 상기 화합물 A2-2(20g, 52.7mmol), 비스 (피나콜라토)다이보론 (14.72g, 57.97匪01) 및 아세트산칼륨 (10.34g, 105.4mmol)을 섞고， 디옥산 (300ml)를 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스 (디벤질리딘아세톤)팔라듐 (606mg, 1.05mol)과 트리사이클로핵실포스핀 (591mg, 2.10 mmol)을 넣고 3시간 동안 가열 및 교반하였다. 반웅 종료 후， 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고， 유기층을 무수황간마그네슴으로 건조하였다. 감압 증류 후 테트라하이드로퓨란과 에틸아세테이트로 재결정하여 상기 화합물 A4-l(19.1g, 85%)을 제조하였다. Mixing the compound A2-2 (20g, 52.7mmol), bis (pinacolato) di boron (14.72g, 57.97匪0 1), and potassium acetate (10.34g, 105.4mmol) under nitrogen and dioxane (300ml) Was added and heated with stirring. Bis (dibenzylidineacetone) palladium (606 mg, 1.05 mol) and tricyclohexylphosphine (591 mg, 2.10 mmol) were added under reflux for 3 hours, Lt; / RTI &gt; After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous yellow magnets. After distillation under reduced pressure, the residue was recrystallized from tetrahydrofuran and ethyl acetate to give the above compound A4-1 (19.1 g, 85%).
MS[M+H]+= 427.32 MS [M + H] &lt; + &gt; = 427.32
Figure imgf000143_0001
상기 A3-1 의 합성에서 A2-1 대신 A4-1를， 3-클로로페닐보로닉산 대신
Figure imgf000143_0001
In the above synthesis of A3-1, A4-1 was used instead of A2-1, 3-chlorophenylboronic acid
5-브로모나프탈렌 -1-올을 사용한 것을 제외하고는 동일한 방법으로 합성하여 A4-2 를 제조하였다 Except that 5-bromonaphthalen-1-ol was used instead of 5-bromonaphthalen-1-ol to prepare A4-2
MS[M+H]+= 443.51 MS [M + H] &lt; + &gt; = 443.51
Figure imgf000143_0002
화합물 A4-2(15g, 33.89瞧 ol )와 포타슘카보네이트 (7.0g, 50.7匪01 )를 AN (200ml ) 및 H20(50ml )에 넣고 교반한 뒤 NNF(13.3g, 44.05瞧 ol )를 넣는다. 에틸아세테이트와 물을 이용하여 추출하고 용매 제거 후， 테트라하이드로퓨란과 에틸아세테이트로 재결정하여 화합물 A4-3(10.84g, 75%)을 제조하였다. MS[M+H]+= 426.51 제조예 3-6: A3-3의 합성
Figure imgf000143_0002
The mixture was stirred in an AN (200 ml) and H 2 O (50 ml), and NNF (13.3 g, 44.05 瞧 ol) was added to the mixture of compound A4-2 (15 g, 33.89 瞧 ol) and potassium carbonate (7.0 g, 50.7 匪 01). The reaction mixture was extracted with ethyl acetate and water, and the solvent was removed. The residue was recrystallized from tetrahydrofuran and ethyl acetate to obtain Compound A4-3 (10.84 g, 75%). MS [M + H] &lt; + &gt; = 426.51 Preparation Example 3-6: Synthesis of A3-3
Figure imgf000144_0001
Figure imgf000144_0001
A2-3 A3-3 상기 A3-1의 합성에서 A2-1 대신 A2-3을， 3-클로로페닐보로닉산 대신 2-클로로페닐보로닉산을 사용한 것을 제외하고는 동일한 방법으로 합성하여 A3-3 를 제조하였다  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
MS[M+H]+= 411.90 MS [M + H] &lt; + &gt; = 411.90
Figure imgf000144_0002
Figure imgf000144_0002
A3-4 상기 A3-1의 합성에서 A2— 1 대신 A2-4를 사용한 것을 제외하고는 동일한 방법으로 합성하여 A3-4를 제조하였다  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
MS[M+H]+= 411.90 제조예 3-8: A3-5의 합성
Figure imgf000145_0001
MS [M + H] &lt; + &gt; = 411.90 Preparation Example 3-8: Synthesis of A3-5
Figure imgf000145_0001
A3-5 상기 A4-1의 합성에서 A2-2 대신 A2-4를 사용한 것을 제외하고는 동일한 방법으로 합성하여 A3-5 를 제조하였다  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
MS[M+H]+= 427.32 MS [M + H] &lt; + &gt; = 427.32
Figure imgf000145_0002
Figure imgf000145_0002
B2- B3- 상기 A3-1의 합성,에서 A2-1 대신 B2-1을， 3-클로로페닐보로닉산 대신 4-클로로페닐보로닉산을 사용한 것을 제외하고는 동일한 방법으로 합성하여 B3-1 를 제조하였다.  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 .
MS[M+H]+= 536.04 MS [M + H] &lt; + &gt; = 536.04
Figure imgf000145_0003
상기 A3-1의 합성에서 A2-1 대신 B2-2를 사용한 것을 제외하고는 동일한 방법으로 합성하여 B3-2를 제조하였다.
Figure imgf000145_0003
Except for using B2-2 instead of A2-1 in the synthesis of A3-1 above Synthesis was conducted in the same manner to prepare B3-2.
MS[M+H] += 536.04  MS [M + H] &lt; + &gt; = 536.04
Figure imgf000146_0001
Figure imgf000146_0001
상기 A3-1의 합성에서 A2— 1 대신 B2-3를， 3-클로로페닐보로닉산 대신Instead of A2-1, B2-3 was used in the synthesis of A3-1, instead of 3-chlorophenylboronic acid
2-클로로페닐보로닉산을 사용한 것을 제외하고는 동일한 방법으로 합성하여 B3-3을 제조하였다. B3-3 was prepared by the same method except for using 2-chlorophenylboronic acid.
MS[M+H]+= 536.04  MS [M + H] &lt; + &gt; = 536.04
Figure imgf000146_0002
상기 A4-1의 합성에서 A2-.2 대신 B2-4를 사용한 것을 제외하고는 동일한 방법으로 합성하여 B3-4를 제조하였다
Figure imgf000146_0002
B3-4 was synthesized by the same method except for using B2-4 instead of A2- .2 in the synthesis of A4-1
MS[M+H] += 551 .46 제조예 4  MS [M + H] &lt; + &gt; = 551.46 [
제조예 4-1: 화합물 1의 합성 Production Example 4-1: Synthesis of Compound 1
Figure imgf000147_0001
Figure imgf000147_0001
A2-l(15g, 39.55mmol ) , 다이 ( [1，1' -바이페닐] -4-일)아민 (12.96g, 40.3½mol ) 및 소듐 -t-부특사이드 (5.3， 55.37mol )을 자일렌에 넣고 가열 교반한 뒤 환류시키고 [비스 (트라이 _t-부틸포스핀) ]팔라듐 (404mg, 2mmol%)을 넣는다. 상온으로 은도를 낮추고 반응을 종결한 후， 테트라하이드로퓨란과 에틸아세테이트를 이용해 재결정하여 화합물 1(19.6g, 82%)을 제조하였다. (13.5 g, 39.55 mmol), di ([1,1'-biphenyl] -4-yl) amine (12.96 g, 40.3 m mol) and sodium- , And the mixture was stirred under heating, refluxed, and [bis (tri-t-butylphosphine)] palladium (404 mg, 2 mmol%) was added. After lowering the silver concentration to room temperature and terminating the reaction, the compound 1 was recrystallized by using tetrahydrofuran and ethyl acetate to prepare Compound 1 (19.6 g, 82%).
MS[M+H]+= 620.76 MS [M + H] &lt; + &gt; = 620.76
Figure imgf000147_0002
상기 화합물 1의 합성에서 다이 ( [1，1' -바이페닐] -4-일)아민 대신 N- ( [1，1' -다이페닐] -4-일) -9， 9-다이메틸 -9H—플루오렌 -2-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 2를 제조하였다
Figure imgf000147_0002
([L, l ' -diphenyl] -4-yl) -9,9-dimethyl-9H -Fluorene-2-amine, the compound 2 was prepared
MS[M+H]+= 660.83 제조예 4-3: 화합물 3의 합성 MS [M + H] &lt; + &gt; = 660.83 Preparation Example 4-3: Synthesis of Compound 3
Figure imgf000148_0001
상기 화합물 1의 합성에서 A2-1 대신 A2-2를, 다이 ([1，1' -바이페닐] - 4-일)아민 대신 N,9,9-트리페닐 -9H-플루오렌 -3-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 3을 제조하였다
Figure imgf000148_0001
A2-2 was used instead of A2-1 in the synthesis of Compound 1, N, 9,9-triphenyl-9H-fluorene-3-amine ( Was used to synthesize Compound 3
MS[M+H]+= 708.87 MS [M + H] &lt; + &gt; = 708.87
Figure imgf000148_0002
상기 화합물 1 의 합성에서 A2-1 대신 A2-2를， 다이 ([1，1' -바이페닐] - 4-일)아민 대신 4- (디벤조 [b,d]퓨란 -4-일) -N-페닐아닐린을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 4를 제조하였다
Figure imgf000148_0002
(Dibenzo [b, d] furan-4-yl) - amine instead of di [(1,1'-biphenyl- N-phenylaniline was used instead of N-phenylaniline, compound 4 was prepared
MS[M+H]+= 634.75 MS [M + H] &lt; + &gt; = 634.75
Figure imgf000148_0003
Figure imgf000148_0003
A2-3 상기 화합물 1의 합성에서 A2-1 대신 A2-3을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 5를 제조하였다. 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.
MS[M+H]+= 620.76 MS [M + H] &lt; + &gt; = 620.76
Figure imgf000149_0001
Figure imgf000149_0001
상기 화합물 1 의 합성에서 A2-1 대신 A2-2를， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 N,9-디페닐 -9H-카바졸 -3-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 6을 제조하였다 A2-2 was used instead of A2-1 in the synthesis of Compound 1, and N, 9-diphenyl-9H-carbazol-3-amine was used in place of di [(1,1'-biphenyl- Was synthesized in the same way to give Compound 6
MS[M+H]+= 633.76 MS [M + H] &lt; + &gt; = 633.76
Figure imgf000149_0002
상기 화합물 1 의 합성에서 A2-1 대신 A2-4를， 다이 ([1，1' -바이페닐] - 4-일)아민 대신 Ν-([1,1' -다이페닐] -4-일) -9,9-다이메틸 -9Η-플루오렌 -2- 아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 7을 제조하였다
Figure imgf000149_0002
A2- ([1,1'-diphenyl] -4-yl) amine was used instead of di [(1,1'-biphenyl- -9,9-dimethyl-9H-fluorene-2-amine was used to prepare Compound 7
MS[M+H]+= 660.83 제조예 4-8: 화합물 8의 합성
Figure imgf000150_0001
상기 화합물 1의 합성에서 A2-1 대신 A2-4를, 다이 ( [ 1，1' -바이페닐] -MS [M + H] &lt; + &gt; = 660.83 Preparation Example 4-8: Synthesis of Compound 8
Figure imgf000150_0001
A2-4 in place of A2-1 in the synthesis of Compound 1, di [(1,1'-biphenyl] -
4-일)아민 대신 4ᅳ (9，9-디페닐-911-플루오렌-4-일) -페닐아닐린을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 8을 제조하였다 (9,9-diphenyl-9,11-fluoren-4-yl) -phenylaniline was used in place of 4-
MS[M+H]+= 784.97 MS [M + H] &lt; + &gt; = 784.97
Figure imgf000150_0002
상기 화합물 1 의 합성에서 A2-1 대신 B2-1을， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 N-페닐 -[ 1，1' ： 4' ， 1" -터페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 9를 제조하였다
Figure imgf000150_0002
In the synthesis of the compound 1, B2-1 was used instead of A2-1, and N-phenyl- [1,1 ': 4', 1 '' - tert- Phenyl] -4-amine, the compound 9 was prepared
MS[M+H]+= 744.91 제조예 4-10: 화합물 10의 합성 MS [M + H] &lt; + &gt; = 744.91 Preparation Example 4-10: Synthesis of Compound 10
Figure imgf000151_0001
상기 화합물 1의 합성에서 A2-1 대신 B2-1을， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 다이 ( [1，1' -바이페닐] -4-일) -(1，1' -디페닐) -2-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 10을 제조하였다.
Figure imgf000151_0001
In the synthesis of the compound 1, B2-1 was used instead of A2-1, di ([1,1'-biphenyl] -4-yl) - (1,1'-diphenyl) -2-amine, the compound 10 was prepared.
MS[M+H]+= 744.91 MS [M + H] &lt; + &gt; = 744.91
Figure imgf000151_0002
상기 화합물 1 의 합성에서 A2-1 대신 B2-2를， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 9，9-디메틸^-페닐-911-플루오렌-2-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 11을 제조하였다
Figure imgf000151_0002
In the synthesis of Compound 1, B2-2 was used instead of A2-1, 9,9-dimethyl-phenyl-911-fluorene-2-amine Was synthesized in the same manner as above to give Compound 11
MS[M+H]+= 708.87 MS [M + H] &lt; + &gt; = 708.87
Figure imgf000151_0003
화합물 1의 합성에서 A2-1 대신 B2-2를， 다이 ( [1 , 1' -바이페닐] - 4-일)아민 대신 N, 9， 9-트리페닐 -9H—플루오렌 -2-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 12를 제조하였다
Figure imgf000151_0003
In the synthesis of Compound 1, B2-2 was used instead of A2-1, a dye ([1,1'-biphenyl] - 4-yl) amine instead of N, 9,9-triphenyl-9H-fluorene-2-amine, Compound 12 was prepared
MS[M+H]+= 833.02 MS [M + H] &lt; + &gt; = 833.02
Figure imgf000152_0001
Figure imgf000152_0001
13  13
B2-3 상기 화합물 1의 합성에서 A2 1 대신 B2-3을， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 N-페닐나프탈렌 -1-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 13을 제조하였다  B2-3 In the synthesis of the compound 1, except for using B2-3 instead of A2 1 and using N-phenylnaphthalen-1-amine instead of di [(1,1 '-biphenyl] -4-yl) amine To prepare Compound 13
MS[M+H]+= 642.77 MS [M + H] &lt; + &gt; = 642.77
Figure imgf000152_0002
Figure imgf000152_0002
상기 화합물 1의 합성에서 A2-1 대신 B2-3을, 다이 ( [ 1，1' —바이페닐] - 4-일)아민 대신 N-페닐 -[ 1 , 1' -비페닐] -3-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 14를 제조하였다 In the synthesis of Compound 1, B2-3 was used instead of A2-1, N-phenyl- [1,1'-biphenyl] -3-amine Was synthesized in the same manner as above to give Compound 14
MS[M+H]+= 668.81 제조예 4-15: 화합물 15 의 합성 MS [M + H] &lt; + &gt; = 668.81 Preparation Example 4-15: Synthesis of Compound 15
Figure imgf000153_0001
상기 화합물 1의 합성에서 A2-1 대신 B2-4을， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 N-페닐 -[1，1' ： 4' , 1" -터페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 15 를 제조하였다
Figure imgf000153_0001
In the synthesis of the compound 1, B2-4 was used instead of A2-1 and N-phenyl- [1,1 ': 4', 1 '' - tert- Phenyl] -4-amine, the compound 15 was prepared
MS[M+H]+= 744.91 MS [M + H] &lt; + &gt; = 744.91
Figure imgf000153_0002
상기 화합물 1의 합성에서 A2-1 대신 B2-4를， 다이 ( [1，1' -바이페닐] - -일)아민 대신 다이 ( [1，1' -바이페닐] -4-일) -(1，1' -디페닐) -2-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 16을 제조하였다
Figure imgf000153_0002
In the synthesis of the compound 1, B2-4 was used instead of A2-1, and a dye ([1,1'-biphenyl] -4-yl) - ( 1,1 '-diphenyl) -2-amine was used to prepare compound 16
MS[M+H]+= 744.91 MS [M + H] &lt; + &gt; = 744.91
Figure imgf000153_0003
Figure imgf000153_0003
A3- 17 상기 화합물 1의 합성에서 A2-1 대신 A3-1을， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 N-페닐 -[1，1' -비페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 17을 제조하였다 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
MS[M+H]+= 620.76 MS [M + H] &lt; + &gt; = 620.76
Figure imgf000154_0001
상기 화합물 1 의 합성에서 A2-1 대신 A3-2를， 다이 ( [1,1' -바이페닐] -
Figure imgf000154_0001
A3-2 was used in place of A2-1 in the synthesis of the compound 1, a di ([1,1'-biphenyl] -
4-일)아민 대신 N-페닐디벤조 [b,d]푸란 -1-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 18을 제조하였다 Dibenzo [b, d] furan-1-amine instead of N-phenyl dibenzo [b, d] furan-1-amine
MS[M+H]+= 634.75 MS [M + H] &lt; + &gt; = 634.75
Figure imgf000154_0002
상기 화합물 1 의 합성에서 A2-1 대신 A4-3을， 다이 ([1，1ᅳ -바이페닐] -
Figure imgf000154_0002
In the synthesis of Compound 1, A4-3 was used instead of A2-1, a dye ([1,1'-biphenyl] -
4-일)아민 대신 4-브로모 -Ν,Ν-디페닐아닐린을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 19를 제조하였다 4-yl) amine was used instead of 4-bromo-N, N-diphenyl aniline, compound 19 was prepared
MS[M+H]+= 670.82 제조예 4-20: 화합물 20의 합성 MS [M + H] &lt; + &gt; = 670.82 Preparation Example 4-20: Synthesis of Compound 20
Figure imgf000155_0001
Figure imgf000155_0001
상기 화합물 1의 합성에서 A2-1 대신 A3-3을， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 Ν-( [ 1 , 1' -다이페닐] -4-일) -9，9-다이메틸 -9Η-플루오렌 -2- 아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 20을 제조하였다 (1, 1 '-diphenyl] -4-yl) amine instead of di [(1,1'-biphenyl- -9,9-dimethyl-9H-fluorene-2-amine, the compound 20 was prepared
MS[M+H]+= 736.96 MS [M + H] &lt; + &gt; = 736.96
Figure imgf000155_0002
상기 화합물 1의 합성에서 A2-1 대신 A3-4를 사용한 것을 제외하고 동일한 방법으로 합성하여 화합물 21을 제조하였다
Figure imgf000155_0002
Compound 21 was prepared by the same method except that A3-4 was used instead of A2-1 in the synthesis of Compound 1
MS[M+H]+= 696.86 제조예 4-22: 화합물 22의 합성 MS [M + H] &lt; + &gt; = 696.86 Preparation 4-22: Synthesis of Compound 22
Figure imgf000156_0001
상기 화합물 1의 합성에서 A2-1 대신 A3-5를， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 4' -브로모 -Ν,Ν-디페닐 -[ 1，1' -디페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 22를 제조하였다
Figure imgf000156_0001
In the synthesis of Compound 1, A3-5 was used instead of A2-1, 4'-bromo-N, N-diphenyl- [1,1'-biphenyl- '-Diphenyl] -4-amine, the compound 22 was prepared
MS[M+H]+= 620.76 MS [M + H] &lt; + &gt; = 620.76
Figure imgf000156_0002
Figure imgf000156_0002
상기 화합물 1 의 합성에서 A2-1 대신 B3-1을， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 N-페닐 -[1，1' -비페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 23올 제조하였다 B3-1 was used instead of A2-1 in the synthesis of Compound 1, and N-phenyl- [l, l ' -biphenyl] -4-amine Was used in the same manner as above to prepare 23
MS[M+H]+= 744.91 제조예 4-24: 화합물 24의 합성 MS [M + H] &lt; + &gt; = 744.91 Preparation Example 4-24: Synthesis of Compound 24
Figure imgf000157_0001
상기 화합물 1 의 합성에서 A2 1 대신 B3-2를， 다이 ([1，1' -바이페닐] - 4-일)아민 대신 N-페닐 -[1，1' :4' ,1" -터페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 24를 제조하였다
Figure imgf000157_0001
In the synthesis of Compound 1, B3-2 was used instead of A2 1, and N-phenyl- [1,1 ': 4', 1 "-terphenyl (1,1'-biphenyl- ] -4-amine, the compound 24 was prepared
MS[M+H]+= 821.00 MS [M + H] &lt; + &gt; = 821.00
Figure imgf000157_0002
Figure imgf000157_0002
상기 화합물 1 의 합성에서 A2-1 대신 B3-3를， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 N-페닐 -비페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 25를 제조하였다  Except that B3-3 was used instead of A2-1 in the synthesis of Compound 1 and N-phenyl-biphenyl] -4-amine was used instead of di [(1,1 '-biphenyl] The compound 25 was synthesized by the same method
MS[M+H]+= 744.91 MS [M + H] &lt; + &gt; = 744.91
Figure imgf000157_0003
상기 화합물 1의 합성에서 A2-1 대신 B3-4를， 다이 ( [ 1，1' -바이페닐] -
Figure imgf000157_0003
B3-4 was used in place of A2-1 in the synthesis of the compound 1, di [(1,1'-biphenyl] -
4-일)아민 대신 4-브로모 -Ν,Ν-디페닐아닐린을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 26을 제조하였다 4-yl) amine was used instead of 4-bromo-N, N-diphenyl aniline, Compound 26 was prepared
MS[M+H]+= 668.81 MS [M + H] &lt; + &gt; = 668.81
Figure imgf000158_0001
상기 화합물 1 의 합성에서 A2-1 대신 A2-5를， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 N-페닐 _[ 1，1' —비페닐] -4-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 27을 제조하였다
Figure imgf000158_0001
In the synthesis of Compound 1, A2-5 was used instead of A2-1, and N-phenyl [l, l ' -biphenyl] -4-amine Was used, to thereby prepare Compound 27
MS[M+H]+= 787.98 MS [M + H] &lt; + &gt; = 787.98
Figure imgf000158_0002
상기 화합물 1 의 합성에서 A2-1 대신 A2-6을， 다이 ( [ 1，1' -바이페닐] - 4-일)아민 대신 N-페닐디벤조 [b , d]푸란 -1-아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 28 를 제조하였다
Figure imgf000158_0002
In the synthesis of Compound 1, A2-6 was used instead of A2-1, and N-phenyldibenzo [b, d] furan-1-amine was used in place of di [(1,1'-biphenyl- Was synthesized in the same way to give Compound 28
MS[M+H]+= 815.94
Figure imgf000159_0001
상기 화합물 1 의 합성에서 A2-1 대신 B2-5를， 다이 ([1，1' -바이페닐] - 4-일)아민 대신 N-페닐— 1-나프틸아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 29를 제조하였다 MS [M + H] &lt; + &gt; = 815.94
Figure imgf000159_0001
Except that B2-5 was used instead of A2-1 in the synthesis of Compound 1 and N-phenyl-1-naphthylamine was used in place of di [(1,1'-biphenyl] To give Compound 29
MS[M+H]+= 860.04 MS [M + H] &lt; + &gt; = 860.04
Figure imgf000159_0002
상기 화합물 1의 합성에서 A2-1 대신 B2-6을， 다이 ( [1，1' -바이페닐] - 4-일)아민 대신 디페닐아민을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 30를 제조하였다
Figure imgf000159_0002
Synthesis was carried out in the same manner as in the synthesis of the compound 1, except that B2-6 was used instead of A2-1 and diphenylamine was used instead of di [(1,1 '-biphenyl] -4-yl) amine to give Compound 30 Gt;
MS[M+H]+= 759.92 실시예 1 MS [M + H] &lt; + &gt; = 759.92 Example 1
ΠΌ (인듐 주석 산화물)가 1,000 A 두께로 박막 코팅된 유리 기판 (corning 7059 glass)을， 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터 (Filter)로 2차 걸러진 증류수를 사용하였다. ΠΌ를 30분간 세척한 후， 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜， 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. 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.
이렇게 준비된 ITO 투명 전극 위에 핵사니트릴 핵사아자트리페닐기렌 (hexani tr i le hexaazatr i phenyl ene)를 500A의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 정공을 수송하는 물질인 위 제조예 4-1에서 합성한 화합물 1을 900 A의 두께로 진공 증착하여 전공수송층을 형성한 후， 이어서 상기 정공수송층 위에 HT2를 막두께 50A으로 진공증착하여 정공조절층을 형성하였다. 이후， 상기 정공조절층 위에 발광층으로 호스트 HI과 도판트 D1 화합물 (25 : 1)을 300A의 두께로 진공 증착하였다. 이어서 상기 발광층 위에 E1 화합물을 300A의 두께로 진공 증착하여 전자수송층을 형성하였다. 상기 전자수송층 위에 순차적으로 12A 두께의 리튬 플루오라이드 (L i F)와 2 , 000A 두께의 알루미늄을 증착하여 음극을 형성하여， 유기 발광 소자를 제조하였다. 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. Subsequently, HT2 was vacuum-deposited on the hole transport layer to a thickness of 50 A To form a hole control layer. Subsequently, 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. Subsequently, an E1 compound was vacuum deposited on the light emitting layer to a thickness of 300 A to form an electron transporting layer. By forming the cathode by sequentially depositing lithium fluoride fluoroalkyl 12A thickness (L i F) and 2, 000A thick aluminum on the electron transport layer, an organic light emitting device was produced.
상기의 과정에서 유기물의 증착속도는 lA/sec를 유지하였고， 리튬플루라이드는 0.2A/sec , 알루미늄은 3 ~ 7A/sec의 증착속도를 유지하였다. In the above process, 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, and the deposition rate of aluminum was 3 to 7 A / sec.
Hexan
Figure imgf000161_0001
itrile hexazatriphenylene
Figure imgf000161_0002
Hexan
Figure imgf000161_0001
itrile hexazatriphenylene
Figure imgf000161_0002
Figure imgf000161_0003
실시예 2내지 20및 비교예 1 내지 3
Figure imgf000161_0003
Examples 2 to 20 and Comparative Examples 1 to 3
상기 실시예 1에서 정공수송층으로 화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 제조하였다. 상기 실시예 1 내지 20 및 비교예 1 내지 3에서 제조한 유기 발광 소자에 전류 (20mA/cm2)를 인가하여， 전압， 효율， 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. 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.
【표 11 [Table 11
Figure imgf000162_0001
Figure imgf000162_0001
실시예 21 Example 21
ITO (인듐 주석 산화물)가 1 ,000 Α 두께로 박막 코팅된 유리 기판 (corning 7059 glass)을， 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며， 증류수는 Millipore Co. 제품의 필터 (Filter)로 2차 걸러진 증류수를 사용하였다. IT0를 30분간 세척한 후， 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜， 아세톤， 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. ITO (Indium Tin Oxide) is a thin film-coated glass with a thickness of 1,000 A The substrate (corning 7059 glass) was immersed in distilled water 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. 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.
이렇게 준비된 ITO 투명 전극 위에 핵사니트릴 핵사아자트리페닐기렌 (hexanitrile hexaazatr i phenyl ene)를 500A의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 정공을 수송하는 물질인 ΗΊΊ을 900A의 두께로 진공 증착하여 정공수송층을 형성하고， 상기 정공수송층 위에 제조예 4-3에서 합성한 화합물 3을 막두께 50 A으로 진공 증착하여 정공조절층을 형성하였다. 화합물 발광층으로 호스트 HI과 도판트 D1 화합물 (25:1)을 300 A의 두께로 진공 증착하였다. 이후， 상기 발광층 위에 E1 화합물을 300 A의 두께로 열 진공 증착하여 전자수송층을 형성하고， 이어서 상기 전자수송층 위에 순차적으로 12A 두께의 리튬 플루오라이드 (LiF)와 2,000A 두께의 알루미늄을 증착하여 음극을 형성하여， 유기 발광 소자를 제조하였다.  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. Vacuum deposition of Compound 3 synthesized in Production Example 4-3 on the hole transport layer to a thickness of 50 A To form a control 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. Thereafter, 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.
상기의 과정에서 유기물의 증착속도는 1 A /sec를 유지하였고, 리튬플루라이드는 0.2A/sec, 알루미늄은 3 ~ 7A/sec의 증착속도를 유지하였다. In the above process, the deposition rate of the organic material was maintained at 1 A / sec, the deposition rate of lithium fluoride was 0.2 A / sec, and the deposition rate of aluminum was 3 to 7 A / sec.
Figure imgf000164_0001
Figure imgf000164_0001
ı63 I63
실시예 22내지 42및 비교예 4내지 8 Examples 22 to 42 and Comparative Examples 4 to 8
상기 실시예 21 에서 정공조절층으 ο로 화합물 3 대신 하기 표 2에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 o  Except that the compound described in the following Table 2 was used instead of the compound 3 as the hole control layer in Example 21,
제조하였다. .
~  ~
상기 실시예 21 내지 42 및 비교예 4 내지 8에서 제조한 유기 발광 소자에 전류 (20mA/cm2)를 인가하여， 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. 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.
【표 2] 정공조절층 전압 (V) 효율 (Cd/A) 색좌표 (x,y) 수명 (Τ95, h) 실시예 21 화합물 3 3.58 5.55 (0.135, 0.138) 51.5 (T, 95) Example 21 Compound 3 3.58 5.55 (0.135, 0.138) 51.5 (t,
실시예 22 화합물 4 3.52 5.68 (0.133， 0.139) 50.5  Example 22 Compound 4 3.52 5.68 (0.133, 0.139) 50.5
실시예 23 화합물 5 3.59 6.11 52.1  Example 23 Compound 5 3.59 6.11 52.1
실시예 24 화합물 6 3.66 5.92 (0.134, 0.138) 49.8  Example 24 Compound 6 3.66 5.92 (0.134, 0.138) 49.8
실시예 25 화합물 8 3.68 5.69 (0.136, 0.139) 53.5  Example 25 Compound 8 3.68 5.69 (0.136, 0.139) 53.5
실시예 26 화합물 9 3.53 5.99 (0.136, 0.139) 51.0  Example 26 Compound 9 3.53 5.99 (0.136, 0.139) 51.0
실시예 27 화합물 10 3.52 6.12 (0.136， 0.123) 54.8  Example 27 Compound 10 3.52 6.12 (0.136, 0.123) 54.8
실시예 28 화합물 11 3.55 6.23 (0.134， 0.138) 55.0  Example 28 Compound 11 3.55 6.23 (0.134, 0.138) 55.0
실시예 29 화합물 12 3.79 6.22 (0.135， 0.138) 53.1  Example 29 Compound 12 3.79 6.22 (0.135, 0.138) 53.1
실시예 30 화합물 14 3.78 5.99 (0.134, 0.137) 52.8  Example 30 Compound 14 3.78 5.99 (0.134, 0.137) 52.8
실시예 31 화합물 15 3.66 6.03 (0.135, 0.138) 50.6 Example 31 Compound 15 3.66 6.03 (0.135, 0.138) 50.6
실시예 32 화합물 16 3.62 6.21 (0.134， 0.138) 53.4 Example 32 Compound 16 3.62 6.21 (0.134, 0.138) 53.4
실시예 33 화합물 17 3.77 6.2 (0.136， 0.139) 55.8 Example 33 Compound 17 3.77 6.2 (0.136, 0.139) 55.8
실시예 34 화합물 18 3.68 6.21 (0.135, 0.138) 52.4 Example 34 Compound 18 3.68 6.21 (0.135, 0.138) 52.4
실시예 35 화합물 19 3.78 6.01 (0.133, 0.139) 55.9 Example 35 Compound 19 3.78 6.01 (0.133, 0.139) 55.9
실시예 36 화합물 20 3.77 6.12 (0.135, 0.138) 56.0 Example 36 Compound 20 3.77 6.12 (0.135, 0.138) 56.0
실시예 37 화합물 21 3.88 6.23 (0.135， 0.138) 54.2 실시예 38 화합물 22 3.72 6.1 (0.133, 0.139) 55.2 실시예 39 화합물 23 3.65 5.98 (0.135, 0.138) 51.8 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
실시예 40 화합물 24 3.71 6.02 (0.134, 0.138) 53.4  Example 40 Compound 24 3.71 6.02 (0.134, 0.138) 53.4
실시예 41 화합물 25 3.58 6.12 (0.136, 0.139) 55.1  Example 41 Compound 25 3.58 6.12 (0.136, 0.139) 55.1
실시예 42 화합물 26 3.74 6.31 (0.136， 0.139) 52.8  Example 42 Compound 26 3.74 6.31 (0.136, 0.139) 52.8
비교예 4 HT2 4.11 5.32 (0.136, 0.123) 42.0  Comparative Example 4 HT2 4.11 5.32 (0.136, 0.123) 42.0
비교예 5 HT5 4.05 5.28 (0.136, 0.139) 41.8  Comparative Example 5 HT5 4.05 5.28 (0.136, 0.139) 41.8
비교예 6 HT6 4.21 5.23 (0.136, 0.139) 44.9  Comparative Example 6 HT6 4.21 5.23 (0.136, 0.139) 44.9
비교예 7 HT7 3.98 5.31 (0.136, 0.123) 45.8  Comparative Example 7 HT7 3.98 5.31 (0.136, 0.123) 45.8
비교예 8 HT8 3.99 5.58 (0.134, 0.138) 48.2  Comparative Example 8 HT8 3.99 5.58 (0.134, 0.138) 48.2
상기 표 1 및 2에 따르며， 본 발명에 따른 화학식의 화합물 유도체는 유기 발광 소자를 비롯한 유기 전자 소자에서 정공 수송 및 정공조절 역할을 할 수 있으며， 이러한 화합물 유도체를 포함하는 소자는 효율， 구동전압， 안정성 면에서 우수한특성을 나타냄을 확인했다. According to Tables 1 and 2, 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.
【부호의 설명】 DESCRIPTION OF REFERENCE NUMERALS
기판
Figure imgf000166_0001
Board
Figure imgf000166_0001
3 발광층 으그  3 light emitting layer
ᄆ — I  ᄆ - I
5 정공주입층 정공수송층  5 Hole injection layer Hole transport layer
정공조절층 발광층  The hole-
전자수송층  Electron transport layer

Claims

【청구범위】 【청구항 1] 하기 화학식 1로 표시되는 화합물: Claims 1. A compound represented by the following formula (1):
[화학식 1]  [Chemical Formula 1]
Figure imgf000167_0001
Figure imgf000167_0001
상기 화학식 1에서,  In Formula 1,
Yl 및 Υ2는 각각 독립적으로 수소; 치환 또는 비치환된 d-40 알킬; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 0， N , Si 및 S 중Yl and Υ 2 are each independently hydrogen, Substituted or unsubstituted d-40 alkyl; Substituted or unsubstituted C 6 -C 60 aryl; Or substituted or unsubstituted 0, N, Si and S
1개 이상을 포함하는 C2-60 헤테로아릴이고， A C 2 -60 heteroaryl containing 1 or more,
An 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 치환 또는 비치환된 0， N , Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로아릴이거나, 또는 A 내지 Ar4는 서로 인접하는 기와 결합하여 축합 고리를 형성하고， An and Ar 2 are each independently a substituted or unsubstituted C 6 - 60 substituted or unsubstituted C 2 - 60 heteroaryl containing at least one of O, N, Si and S, or A to Ar 4 are Bonded to each other to form a condensed ring,
내지 L3은 각각 독립적으로 직접 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 N , 0， S 및 Si로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로 원자를 포함하는 C2-60 헤테로아릴렌이고， To L &lt; 3 &gt; 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 내지 ¾은 각각 독립적으로 수소; 중수소; 할로겐; 히도록시기; 시아노; 니트릴; 나트로; 아미노; 치환 또는 비치환된 d-60 알킬 ; 치환 또는 비치환된 d-60 할로알킬 ; 치환 또는 비치환된 d-60 티오알킬 ; 치환 또는 비치환된 Cwo 알콕시 ; 치환 또는 비치환된 d-60 할로알콕시 ; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 d-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C6-60 아릴옥시 ; 또는 치환 또는 비치환된 0， N , Si 및 S 중 1개 이상을 포함하는 C2— 60 헤테로아릴이고， Ri and / are each independently hydrogen; heavy hydrogen; halogen; Time to come; Cyano; Nitrile; Natro; 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 - 60 heteroaryl containing at least one of O, N, Si and S,
m은 0 내지 4이고  m is from 0 to 4
0는 0 내지 2이고  0 is 0 to 2
n은 0 내지 3이고 z는 1 내자 4이고， 단， n+z는 4 이하이다. n is from 0 to 3 z is 1 antiferromagnetic 4, provided that n + z is 4 or less.
【청구항 2] [Claim 2]
거 U항에 있어서，  In the above,
상기 화학식 1은 하기 화학식 1-1 내지 1-12로 표시되는 중에서 선택되는 어느 하나인， 화합물:  Wherein the compound represented by Formula 1 is any one selected from the following Formulas 1-1 to 1-12:
Figure imgf000168_0001
Figure imgf000168_0001
[화학식 1-5] [Formula 1-5]
Figure imgf000169_0001
Figure imgf000170_0001
Figure imgf000169_0001
Figure imgf000170_0001
상기 화학식 1-1 내지 1-12에서，  In the above Formulas 1-1 to 1-12,
Li, , , A 및 Ar2에 대한 설명은 제 1항에서 정의한 바와 같다. Li,,, A and Ar 2 are the same as defined in claim 1.
【청구항 3] [3]
제 1에 있어서，  In the first aspect,
An 및 Ar2는 각각 독립적으로 하기로 구성되는 군으로부터 선택되는 느 하나인， 화합물: And Ar &lt; 2 &gt; are each independently selected from the group consisting of:
Figure imgf000171_0001
Figure imgf000171_0001
170
Figure imgf000172_0001
//:/ O 9868008ϊ02Μ1κί6SZAV170
Figure imgf000172_0001
// : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000173_0001
Figure imgf000173_0001
Figure imgf000173_0002
Figure imgf000173_0002
Figure imgf000174_0001
Figure imgf000174_0001
Figure imgf000174_0002
Figure imgf000174_0002
173 173
Figure imgf000175_0001
Figure imgf000175_0001
Figure imgf000175_0002
Figure imgf000175_0002
Figure imgf000175_0003
Figure imgf000175_0003
R3은 각각 독립적으로 수소 ; 중수소 ; 할로겐 ; 히드록시기; 시아노 ; 니 트릴 ; 니트로 ; 아미노; 치환 또는 비치환된 d-so 알킬 ; 치환 또는 비치환된 d- 60 할로알킬 ; 치환 또는 비치환된 d-60 알콕시 ; 치환 또는 비치환된 60 할로 알콕시 ; 치환 또는 비치환된 C3-60 사이클로알킬 ; 치환 또는 비치환된 ( -60 알 케닐; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C6-60 아릴옥시 ; 또 는 치환 또는 비치환된 0， N, Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로아 릴이다. R &lt; 3 &gt; are each independently hydrogen; Deuterium; Halogen; A hydroxy group; Cyano; Nitrile; Nitro; Amino; Substituted or unsubstituted d-so alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d- 60 alkoxy; Substituted or unsubstituted 60 haloalkoxy; Substituted or unsubstituted C 3 - 60 cycloalkyl; Substituted or unsubstituted (- 60 alkenyl group; a substituted or unsubstituted C 6 - 60 aryl, substituted or unsubstituted C 6 - 60 aryloxy; or a substituted or unsubstituted 0, N, Si and S 1 C 2 - 60 Hetero A It is a reel.
【청구항 4] [4]
제 1에 있어서,  In the first aspect,
Li 내지 L3은 각각 독립적으로 직접결합 또는 하기로 구성되 부터 선택되는 어느 하나인， 화합물. Li and L &lt; 3 &gt; are each independently a direct bond or any one selected from the group consisting of
Figure imgf000176_0001
Figure imgf000176_0001
【청구항 5】 [Claim 5]
제 1항에 있어서，  The method according to claim 1,
상기 화학식 1로 표시되는 화합물은 하기 화합물로 구성되는 군으로부 터 선택되는 어느 하나인 것을 특징으로 하는， 화합물: //:/ O 9868008ϊ02Μ1κί6SZAV The compound represented by Formula 1 is any one selected from the group consisting of the following compounds: // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000177_0001
Figure imgf000177_0001
Figure imgf000178_0001
Figure imgf000178_0001
Figure imgf000178_0002
Figure imgf000178_0002
Figure imgf000178_0003
Figure imgf000178_0003
177 177
Figure imgf000179_0001
Figure imgf000179_0001
178
Figure imgf000180_0001
178
Figure imgf000180_0001
OAV/:d2NI>/8s OAV / : d2NI > / 8 s
Figure imgf000181_0001
Figure imgf000181_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000182_0001
Figure imgf000182_0001
Figure imgf000183_0001
Figure imgf000183_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000184_0001
Figure imgf000184_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000185_0001
Figure imgf000185_0001
981- 981-
Figure imgf000186_0001
Figure imgf000186_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV 986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV
00 00
Figure imgf000187_0001
Figure imgf000187_0001
Figure imgf000188_0001
Figure imgf000188_0001
Figure imgf000189_0001
Figure imgf000189_0001
188 188
Figure imgf000190_0001
Figure imgf000190_0001
986800/8l0rH¾/X3d
Figure imgf000191_0001
986800 / 8l0rH¾ / X3d
Figure imgf000191_0001
Figure imgf000192_0001
Figure imgf000192_0001
191 //:/ O 9868008ϊ02Μ1κί6SZAV 191 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000193_0001
Figure imgf000193_0001
£61- £ 61-
Figure imgf000194_0001
Figure imgf000194_0001
986800/810ΖΗΜ/Χ3Ι 986800 / 810ZZM / X3I
Figure imgf000195_0001
Figure imgf000195_0001
194 194
Figure imgf000196_0001
Figure imgf000196_0001
195 /// O 9868008ϊ02Μ1><ί6SZA 195 /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000197_0001
Figure imgf000197_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000198_0001
Figure imgf000198_0001
Figure imgf000199_0001
Figure imgf000199_0001
198 /// O 9868008ϊ02Μ1><ί6SZA 198 /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000200_0001
Figure imgf000200_0001
Figure imgf000201_0001
Figure imgf000201_0001
Figure imgf000201_0002
Figure imgf000201_0002
Figure imgf000202_0001
Figure imgf000202_0001
201
Figure imgf000203_0001
201
Figure imgf000203_0001
Figure imgf000204_0001
Figure imgf000204_0001
203 //:/ O 9868008ϊ02Μ1κί6SZAV 203 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000205_0001
Figure imgf000205_0001
Figure imgf000206_0001
Figure imgf000206_0001
Ο/Λ\8102X Ο / Λ \ 810 2X
Figure imgf000207_0001
Figure imgf000207_0001
Figure imgf000208_0001
Figure imgf000208_0001
207 207
Figure imgf000209_0001
Figure imgf000209_0001
208
Figure imgf000210_0001
208
Figure imgf000210_0001
Figure imgf000211_0001
:91S0/610Z OAV
Figure imgf000211_0001
: 91S0 / 610Z OAV
986800/8l0∑H5I/X3d 986800/810? H5I / X3d
Figure imgf000212_0001
Figure imgf000212_0001
2 2
Figure imgf000213_0001
Figure imgf000213_0001
Figure imgf000213_0002
Figure imgf000213_0002
212 212
Figure imgf000214_0001
Figure imgf000214_0001
213 213
0 ¾ 0 ¾
Figure imgf000215_0001
Figure imgf000215_0001
Figure imgf000216_0001
Figure imgf000216_0001
215 //:/ O 9868008ϊ02Μ1κί6SZAV 215 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000217_0001
Figure imgf000217_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000218_0001
Figure imgf000218_0001
Figure imgf000219_0001
Figure imgf000219_0001
218 218
Figure imgf000220_0001
Figure imgf000220_0001
219 219
Figure imgf000221_0001
Figure imgf000221_0001
220 //:/ O 9868008ϊ02Μ1κί6SZAV 220 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000222_0001
Figure imgf000222_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000223_0001
Figure imgf000223_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000224_0001
Figure imgf000224_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000225_0001
Figure imgf000225_0001
Figure imgf000226_0001
Figure imgf000226_0001
225 //:/ O 9868008ϊ02Μ1κί6SZAV 225 // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000227_0001
Figure imgf000227_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000228_0001
Figure imgf000228_0001
Figure imgf000229_0001
Figure imgf000229_0001
Figure imgf000230_0001
Figure imgf000230_0001
Figure imgf000230_0002
Figure imgf000231_0001
Figure imgf000230_0002
Figure imgf000231_0001
Figure imgf000232_0001
Figure imgf000232_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000233_0001
Figure imgf000233_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000234_0001
Figure imgf000234_0001
Figure imgf000235_0001
Figure imgf000235_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000236_0001
Figure imgf000236_0001
Figure imgf000237_0001
Figure imgf000237_0001
Figure imgf000238_0001
Figure imgf000238_0001
Figure imgf000239_0001
Figure imgf000239_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV 6£Z 986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV 6 £ Z
Figure imgf000240_0001
Figure imgf000240_0001
986800/8ΐ0ΖΗΜ/Χ3<Ι 9l7S0/6I0Z OAV
Figure imgf000241_0001
Figure imgf000242_0001
986800 / 8ΐ0ZMI / Χ3 <Ι 9l7S0 / 6I0Z OAV
Figure imgf000241_0001
Figure imgf000242_0001
Figure imgf000243_0001
Figure imgf000243_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000244_0001
Figure imgf000244_0001
Figure imgf000245_0001
Figure imgf000245_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000246_0001
Figure imgf000246_0001
Figure imgf000247_0001
Figure imgf000247_0001
Figure imgf000247_0002
Figure imgf000247_0002
246
Figure imgf000248_0001
246
Figure imgf000248_0001
Figure imgf000249_0001
Figure imgf000249_0001
Figure imgf000250_0001
Figure imgf000250_0001
249 9868//3008s2Md/ K9S06S OZAV 249 9868 // 300 8 s2Md / K9S06S OZAV
Figure imgf000251_0001
Figure imgf000251_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000252_0001
Figure imgf000252_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000253_0001
Figure imgf000253_0001
Figure imgf000254_0001
Figure imgf000254_0001
986800/8T0rH¾/13d 986800 / 8T0rH¾ / 13d
/ O S96SZAV//: 9868008SSMl>d / O S96SZAV // : 986800 8 SSMl > d
Figure imgf000255_0001
Figure imgf000255_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000256_0001
Figure imgf000256_0001
Figure imgf000257_0001
Figure imgf000257_0001
986800/810ZH¾/13d 1-f91"S0/6l0l ΟΛ\ / 986800/81023:12/ O6SZAV 986800 / 810ZH / 13d 1-f91 " S0 / 6l0l ΟΛ \ / 986800/8 1 023: 12 / O 6 S Z AV
Figure imgf000258_0001
Figure imgf000258_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000259_0001
Figure imgf000259_0001
Figure imgf000260_0001
Figure imgf000260_0001
i0
Figure imgf000262_0001
i0
Figure imgf000262_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000263_0001
Figure imgf000263_0001
Figure imgf000264_0001
Figure imgf000264_0001
Figure imgf000265_0001
Figure imgf000265_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000266_0001
Figure imgf000266_0001
Figure imgf000267_0001
Figure imgf000267_0001
Figure imgf000268_0001
Figure imgf000268_0001
986800/8l0ta¾/13d t 9l7S0/6I0i OAV
Figure imgf000269_0001
986800 / 8l0ta¾ / 13d t 9l7S0 / 6I0i OAV
Figure imgf000269_0001
Figure imgf000270_0001
Figure imgf000270_0001
Figure imgf000271_0001
Figure imgf000271_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000272_0001
Figure imgf000272_0001
Figure imgf000273_0001
Figure imgf000273_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000274_0001
Figure imgf000274_0001
/// O 9868008ϊ02Μ1><ί6SZA /// O 986800 8ϊ0 2M1 >< 6SZA
Figure imgf000275_0001
Figure imgf000275_0001
Figure imgf000276_0001
Figure imgf000276_0001
275 98/68008l0/:2Ml>dS/06SZ O.. 275 98/6800 8l0 /: 2Ml> dS / 06SZ O ..
Figure imgf000277_0001
Figure imgf000277_0001
//:/ O 9868008ϊ02Μ1κί6SZAV // : / O 986800 8ϊ0 2M1κί6SZAV
Figure imgf000278_0001
Figure imgf000278_0001
Figure imgf000279_0001
Figure imgf000279_0001
986800/8l0Za¾/X3d 986800 / 8l0Za¾ / X3d
Figure imgf000280_0001
Figure imgf000280_0001
Figure imgf000280_0002
Figure imgf000280_0002
Figure imgf000280_0003
Figure imgf000280_0003
279 279
Figure imgf000281_0001
Figure imgf000281_0001
280 280
Figure imgf000282_0001
Figure imgf000282_0001
281 281
Figure imgf000283_0001
Figure imgf000283_0001
282 282
Figure imgf000284_0001
Figure imgf000284_0001
283 283
Figure imgf000285_0001
Figure imgf000285_0001
【청구항 6】 [Claim 6]
제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 게 2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 제 1항 내지 제 5항 중 어느 하나의 항에 따른 화합물을 포함하는 것인， 유기 발광 소자.  A first electrode; A second electrode facing the first 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 contains the compound according to any one of claims 1 to 5 The organic light-emitting device.
【청구항 7】 7.
제 6항에 있어서，  The method according to claim 6,
상기 화합물을 포함하는 유기물층은 정공주입층; 정공수송층; 정공 주입과 수송을 동시에 하는 층; 정공조절층; 또는 발광층인 것을 특징으로 하는， 유기 발광 소자.  The organic compound layer containing the compound may include a hole injection layer; A hole transport layer; A layer simultaneously injecting and transporting holes; A hole control layer; Or a light emitting layer.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021080334A1 (en) * 2019-10-23 2021-04-29 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006339577A (en) * 2005-06-06 2006-12-14 Konica Minolta Holdings Inc Organic semiconductor thin film and organic thin film transistor
WO2009148015A1 (en) * 2008-06-05 2009-12-10 出光興産株式会社 Halogen compound, polycyclic compound, and organic electroluminescence element comprising the polycyclic compound
KR20120103551A (en) * 2009-06-30 2012-09-19 메르크 파텐트 게엠베하 Materials for organic electroluminescence devices
KR20130064601A (en) * 2011-12-08 2013-06-18 주식회사 두산 Novel compounds and organic electro luminescence device using the same
CN106279055A (en) * 2015-05-12 2017-01-04 上海和辉光电有限公司 A kind of indeno anthracene compound of miscellaneous generation and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101537005B1 (en) * 2012-09-28 2015-07-20 제일모직 주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006339577A (en) * 2005-06-06 2006-12-14 Konica Minolta Holdings Inc Organic semiconductor thin film and organic thin film transistor
WO2009148015A1 (en) * 2008-06-05 2009-12-10 出光興産株式会社 Halogen compound, polycyclic compound, and organic electroluminescence element comprising the polycyclic compound
KR20120103551A (en) * 2009-06-30 2012-09-19 메르크 파텐트 게엠베하 Materials for organic electroluminescence devices
KR20130064601A (en) * 2011-12-08 2013-06-18 주식회사 두산 Novel compounds and organic electro luminescence device using the same
CN106279055A (en) * 2015-05-12 2017-01-04 上海和辉光电有限公司 A kind of indeno anthracene compound of miscellaneous generation and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021080334A1 (en) * 2019-10-23 2021-04-29 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device thereof

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