WO2019147074A1 - Heterocyclic compound and organic light emitting device using same - Google Patents

Heterocyclic compound and organic light emitting device using same Download PDF

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WO2019147074A1
WO2019147074A1 PCT/KR2019/001108 KR2019001108W WO2019147074A1 WO 2019147074 A1 WO2019147074 A1 WO 2019147074A1 KR 2019001108 W KR2019001108 W KR 2019001108W WO 2019147074 A1 WO2019147074 A1 WO 2019147074A1
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compound
group
layer
substituted
unsubstituted
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PCT/KR2019/001108
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French (fr)
Korean (ko)
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박슬찬
이동훈
장분재
정민우
이정하
한수진
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주식회사 엘지화학
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Priority to CN201980003521.3A priority Critical patent/CN110869366B/en
Publication of WO2019147074A1 publication Critical patent/WO2019147074A1/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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K50/16—Electron 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and much research has been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode, and organic substances between the anode and the cathode.
  • the organic material layer may have a multi-layer structure composed of different materials.
  • 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
  • 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).
  • & Lt ; / RTI &gt are each independently substituted or unsubstituted 0-60 alkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 6-60 aryl ; Substituted or unsubstituted 0 6-60 aryloxy ; Or substituted or unsubstituted 0, ratios and 0 2-60 heteroaryls containing at least one of the foregoing,
  • Each of 3 ⁇ 4 to 3 ⁇ 4 is independently halogen; A hydroxy group; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0 1-60 haloalkyl; Substituted or unsubstituted 0 1-60 thioalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0-60 haloalkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 1-60 alkenyl; Substituted or unsubstituted 0 6-60 aryl; Substituted or unsubstituted 0 6-60 aryloxy; Or substituted or unsubstituted 0, ratio 2019/147074 1 »(: 1 ⁇ ⁇ 2019
  • heteroaryl comprising at least one of the following:
  • the present invention also provides a plasma display panel comprising: a first electrode; A low-twelve electrode provided opposite to 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 .
  • the compound represented by the chemical formula described above can be used as a material for organic emission 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 materials.
  • 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 cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 7, a light emitting layer 8, an electron transporting layer 9, And a cathode (4).
  • Fig. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 8, an electron transporting layer 9, an electron injecting and transporting layer 11, The organic light-emitting device shown in FIG.
  • &quot 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 0 or more atoms, or a substituted or unsubstituted group in which at
  • the "substituent group to which two or more substituents are connected” may be a biphenyl group, that is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected to each other.
  • it is preferably a compound having 1 to 40 carbon atoms.
  • 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.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms.
  • it may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, It is not limited.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a butyldimethylboron group, a triphenylboron group, a phenylboron group and the like.
  • 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. Work 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • the alkyl group has 1 to 20 carbon atoms. According to another 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 alkyl groups are methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, 11-butyl, isobutyl, 1-butyl-6 _, 1-methyl-butyl, 1-ethyl-butyl, pentyl, 11-pentyl, isopentyl, neopentyl, 6 ⁇ pentyl, haeksil, 11 haeksil, 1 - methylpentyl, 2-methylpentyl, 4-eu-methyl-2 -pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, 11-heptyl, 1-methyl haeksil, cyclopentylmethyl, cyclohex
  • 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,
  • 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.
  • the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • 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, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • 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,
  • the heterocyclic group is a heterocyclic group containing 0, a ratio and at least one hetero atom 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 pyrrolyl 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, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, 2019/147074 1 »(: 1 :
  • Benzothiophene group benzofuranyl group, phenanthroline group ( 1) 161131 1 11 01 , isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, etc.
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the above-mentioned aryl group.
  • an aralkyl group, an alkyl an alkyl
  • the aryl group and the alkyl group in the alkylamine group are the same as the alkyl groups described above.
  • the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heterocyclic group.
  • the alkenyl group is the same as the above-mentioned alkenyl group.
  • the explanation on the aryl group described above can be applied, except that arylene is divalent.
  • the description of the above-mentioned heterocyclic groups can be applied, except that the heteroaryltentane is divalent.
  • the hydrocarbon ring is not a monovalent hydrocarbon ring, A description about the heteroaryl group or the cycloalkyl group can be applied.
  • the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and the two substituents are bonded to each other .
  • the moiety is methyl.
  • a,,, 1, 6 and groups may be 0,
  • the above formula (1) may be any one selected from the group consisting of the following compounds. 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • the compound represented by the above formula (1) the number of days any one selected from the group consisting of 10 to.
  • the compound represented by the formula ( 1 ) can be prepared by the following reaction scheme (1).
  • the above production method is more specific in the production example to be described later 2019/147074 1 »(: 1/10/0/0 019/001108
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 . 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting 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 a smaller number of organic layers.
  • the organic material layer may include a hole injecting layer, a hole transporting layer, or a hole injecting and transporting layer (layer for simultaneously injecting and transporting holes), and the hole injecting layer, the hole transporting layer, 1 < / RTI >
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
  • the light-emitting layer includes two or more kinds of hosts, and one of the hosts includes a compound represented by the general formula (1).
  • the organic material layer may include an electron transporting layer, an electron injecting layer, or an electron injecting and transporting layer (a layer simultaneously carrying electron injecting and transporting), and the electron transporting layer, the electron injecting layer, 1 < / RTI >
  • the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer include the compound represented by the above formula (1).
  • the organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1). 2019/147074 1 »(: 1/10/0/0 019/001108
  • 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 an anode, one or more organic compound layers 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.
  • 2 is a cross-sectional view of a light emitting device according to a first embodiment of the present invention, which includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, an electron transport layer 9, ) And a cathode (4).
  • the compound represented by Formula 1 may be contained in at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the electron transport layer, and the electron injection layer.
  • FIG. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 8, an electron transporting layer 9, an electron injecting and transporting layer 11,
  • the organic light-emitting device shown in FIG. the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting and transporting layer.
  • the organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic material layers includes the compound represented by the above formula (1).
  • 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 includes a first electrode, 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • an organic material layer and a second electrode in this order.
  • an organic light emitting device can be manufactured 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, roll 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 (0 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 of sons; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (1), zinc oxide (1 fat); 3 ⁇ 40: during or 32: a combination of a metal and an oxide such as ⁇ ; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene], conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
  • 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 Li ⁇ l l, 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 on the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material due to its ability to transport holes, A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable.
  • the HOMOChighest occupied mol ecular orbital 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 organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are 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 as a hole transport material. Suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • 8-hydroxy-quinoline aluminum complex Show 1 3 ⁇ 4
  • Carbazole-based compounds Dimer styryl ((1 161 ⁇ 26 (one-shot) compound; 8 o'clock (1; 10-hydroxybenzoquinoline metal compound; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly ( 1 -phenylenevinylene) 1) series polymer; Spiro group) compound; Polyfluorene,
  • 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 aromatic aromatic ring derivatives include anthracene derivatives, pyrene derivatives, 10 naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds and the like.
  • 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, 15 fluoranthene compounds, and metal complexes.
  • Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as phytenes, anthracene, chrysene, and peripherrhene having an arylamino group.
  • Examples of the styrylamine compounds include substituted or unsubstituted An aryl group, a silyl group, an alkyl group, an aryl group, an aryl group,
  • a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complexes include iridium complexes, platinum complexes and the like, but are not limited thereto.
  • the electron transport material include a receives the electronic electron transport material with a layer of transporting electrons to the light emitting layer receives electrons from the cathode as a substance that give toward the light emitting layer, the electron mobility larger material from the electron injection layer Is suitable.
  • Specific examples include show 1 complexes of 8-hydroxyquinoline; Complexes containing poem 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like,
  • 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, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has the 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10 -hydroxybenzo [ Bis (2-methyl-8-quinolinato), bis (2-methyl-8-quinolinato) ( 0 -cresolato ), Gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) .
  • 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. 2019/147074 1 »(: 1 ⁇ ⁇ 2019/001108
  • Example 3 Preparation of Compound 3
  • Example 35 Preparation of compound 35 Compound show 4 and 2-bromodibenzoide] The title compound was obtained in the same manner as 3- (4-
  • the glass substrate coated with a thin film of 1,300 ⁇ in the ratio of 0 to 3 was cleaned with ultrasonic waves in distilled water containing detergent.
  • the detergent in the Fischer extinct language ⁇ la 0 0) was used as a product is distilled to Millipore (11 0 0 0) was used as the second filtered distilled water to a filter drive (D) of the product.
  • Millipore 11 0 0 0
  • the plate was washed twice with distilled water and ultrasonically cleaned for 1 minute. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the following 111-1 compound was thermally vacuum deposited on the prepared 10-electrode to a thickness of 50 ⁇ to form a hole injection layer.
  • the following 117-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer to form a hole transport layer and vacuum evaporation was performed on the 1 & .
  • the compound 1 prepared in Example 1 Compound and a phosphorescent dopant (3) were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 nm.
  • the following compound was vacuum-deposited to a thickness of 250 nm 2019/147074 1 »(: 1/10/0/0 019/001108
  • an electron transport layer was formed on the electron transport layer by the co-deposition of the following compounds and nigels at a weight ratio of 98: 2.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 to form a cathode.
  • An organic light emitting device was prepared in the same manner as in Experimental Example 1-1 except that the compound described in the following Table 1 was used instead of the Compound 1 of Example 1 in Experimental Example 1.
  • CE1 and The compounds are as follows.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was washed with ultrasonic waves in distilled water containing dispersant.
  • the detergent was manufactured by Fi Scher Co., and the distilled water used was Mi ll ipore Co. Distilled water, which was secondly filtered with a filter (Fi l ter) 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.
  • the following HI-1 compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer.
  • the following HT-1 compound was vacuum-deposited on the hole injection layer to a thickness of 400 A to form a hole transport layer.
  • a host H1 and a dopant D1 compound were vacuum-deposited to a thickness of 300 A at a weight ratio of 97.5: Thereby forming a light emitting layer.
  • the following compound ET-A was vacuum-deposited on the light emitting layer to a thickness of 50 A to form electron transporting gas.
  • Lithium fluoride (aluminum) was deposited with nickel to a thickness of 2,000 to form a cathode.
  • Substrate 2 anode
  • Electron transport layer 10 Electron injection layer

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Abstract

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

Description

2019/147074 1»（：1^1{2019/001108  2019/147074 1 »(: 1 ^ {2019/001108
【발명의 명칭】 Title of the Invention
헤테로고리 화합물및 이를이용한유기발광소자  Heterocyclic compounds and organic light emitting devices using the same
【기술분야】  TECHNICAL FIELD
관련출원（들）과의 상호인용 Cross-reference with related application (s)
본출원은 2018년 1월 26일자 한국 특허 출원 제 10-2018-0010013호에 기초한우선권의 이익을주장하며， 해당한국특허 출원의 문헌에 개시된모든 내용은본명세서의 일부로서 포함된다.  This application claims the benefit of priority based on Korean Patent Application No. 10-2018-0010013, filed on Jan. 26, 2018, the entire contents of which are incorporated herein by reference.
본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한것이다.  The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
【발명의 배경이 되는기술】 TECHNICAL BACKGROUND OF THE INVENTION
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광소자는넓은시야각， 우수한콘트라스트， 빠른응답시간을가지며, 휘도, 구동전압및 응답속도특성이 우수하여 많은연구가진행되고있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 증을 포함하는 구조를 가진다. 상기 유기물 증은 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 엑시톤（6X（:11:011）이 형성되며, 이 엑시톤이 다시 바닥상태로떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로요구되고 있다. 【선행기술문헌】 2019/147074 1»(：1^1{2019/001108 In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and much research has been conducted. The organic light emitting device generally has a structure including an anode and a cathode, and organic substances between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials. 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. If voltage is applied between the two electrodes in the structure of the organic light emitting element in the anode when the hole is, the cathode being so electrons are injected to the organic layer, the injected holes and electrons are met exciton (6 X (: 11: 011 ) the And the light is emitted when the exciton falls back to the ground state. 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] 2019/147074 1 »(: 1 ^ {2019/001108
【특허문헌】 [Patent Literature]
（특허문헌 0001） 한국특허 공개번호제 10-2000-0051826호  (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826
【발명의 내용】 DISCLOSURE OF THE INVENTION
【해결하고자하는과제】  [Problem to be solved]
본 발명은 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자에 관한것이다.  The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
【과제의 해결수단】 MEANS FOR SOLVING THE PROBLEMS
본발명은하기 화학식 1로표시되는화합물을제공한다.  The present invention provides a compound represented by the following formula (1).
[화학식 1]  [Chemical Formula 1]
Figure imgf000003_0001
Figure imgf000003_0001
상기 화학식 1에서，  In Formula 1,
는 0, 또는 0?’ 2이고, Is 0, or 0? 2 ,
묘’ 는 각각 독립적으로 치환 또는 비치환된 01-60 알킬; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 06-60 아릴 ; 치환 또는 비치환된 06-60 아릴옥시 ; 또는 치환 또는 비치환된 0,比 및 중 1개 이상을포함하는 02-60헤테로아릴이고， ≪ / RTI > are each independently substituted or unsubstituted 0-60 alkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 6-60 aryl ; Substituted or unsubstituted 0 6-60 aryloxy ; Or substituted or unsubstituted 0, ratios and 0 2-60 heteroaryls containing at least one of the foregoing,
¾ 내지 ¾은 각각 독립적으로 할로겐; 히드록시기 ; 시아노, 니트릴; 니트로 ; 아미노 ; 치환 또는 비치환된 01-60 알킬 ; 치환 또는 비치환된 01-60 할로알킬 ; 치환 또는 비치환된 01-60 티오알킬 ; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 01-60 할로알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 01-60 알케닐 ; 치환 또는 비치환된 06-60 아릴 ; 치환또는 비치환된 06-60 아릴옥시 ; 또는 치환또는 비치환된 0， 比 2019/147074 1»（：1^1{2019/001108 Each of ¾ to ¾ is independently halogen; A hydroxy group; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0 1-60 haloalkyl; Substituted or unsubstituted 0 1-60 thioalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0-60 haloalkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 1-60 alkenyl; Substituted or unsubstituted 0 6-60 aryl; Substituted or unsubstituted 0 6-60 aryloxy; Or substituted or unsubstituted 0, ratio 2019/147074 1 »(: 1 ^ {2019/001108
및드중 1개 이상을포함하는 02-60헤테로아릴이고， And 0 < 2 > -60 heteroaryl comprising at least one of the following:
6및 §는각각독립적으로 0내지 4이고， 6 and § is from 0 to 4 independently,
13 , 1및 군는각각독립적으로 0내지 3이고， 1 3, 1 and the group is each independently 0 to 3,
：는 0내지 5이다. 또한， 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 저 12 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을포함하는유기 발광소자로서 , 상기 유기물층중 1층이상은상기 화학식 1로표시되는화합물을포함하는, 유기 발광소자를제공한다.  : Is from 0 to 5; The present invention also provides a plasma display panel comprising: a first electrode; A low-twelve electrode provided opposite to 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 .
【발명의 효과】 【Effects of the Invention】
상술한화학식 로표시되는 화합물은유기 발광소자의 유기물증의 재료로서 사용될 수 있으며， 유기 발광소자에서 효율의 향상， 낮은구동전압 및/또는수명 특성을 향상시킬 수 있다. 특히， 상술한 화학식 1로 표시되는 화합물은정공주입， 정공수송， 정공주입 및수송, 발광재료로사용될수 있다.  The compound represented by the chemical formula described above can be used as a material for organic emission 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 materials.
【도면의 간단한설명】 BRIEF DESCRIPTION OF THE DRAWINGS
도 1은 기판 (1) , 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광소자의 예를도시한것이다.  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) , 전자저지층 (7) , 발광층 (8) , 전자수송층 (9)， 전자주입층 (10) 및 음극 (4)로 이루어진유기 발광소자의 예를도시한것이다.  Fig. 2 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 7, a light emitting layer 8, an electron transporting layer 9, And a cathode (4).
도 3은기판 (1) , 양극 (2) , 정공주입층 (5)， 정공수송층 (6)， 발광층 (8)， 전자수송층 (9)， 전자주입 및 수송층 (11)， 및 음극 (4)로 이루어진 유기 발광 소자의 예를도시한것이다.  Fig. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 8, an electron transporting layer 9, an electron injecting and transporting layer 11, The organic light-emitting device shown in FIG.
【발명을실시하기 위한구체적인내용】 DETAILED DESCRIPTION OF THE INVENTION
이하，본발명의 이해를돕기 위하여 보다상세히 설명한다. 본발명은상기 화학식 1로표시되는화합물을제공한다. 2019/147074 1»（：1^1{2019/001108 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). 2019/147074 1 »(: 1 ^ {2019/001108
본명세서에서
Figure imgf000005_0001
다른치환기에 연결되는결합을의미한다. 본명세서에서 ’’치환또는비치환된' 이라는용어는중수소 ; 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 0및 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. 즉, 비페닐기는 아릴기일 수도있고, 2개의 페닐기가연결된치환기로해석될수 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나， 탄소수 1내지 40인 것이 바람직하다. 구체적으로하기와같은구조의 화합물이 될수 있으나， 이에 한정되는것은아니다. 人 人 지 ，人，
Figure imgf000005_0002
본 명세서에 있어서， 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄， 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로치환될수 있다. 구체적으로， 하기 구조식의 화합물이 될수 있으나， 이에 한정되는것은아니다. 2019/147074 1»（：1^1{2019/001108
Figure imgf000006_0001
본 명세서에 있어서， 이미드기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될수있으나, 이에 한정되는것은아니다. In this specification
Figure imgf000005_0001
Means 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 0 or more atoms, or a substituted or unsubstituted group in which at least two of the substituents exemplified above are connected to each other. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group, that is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected to each other. However, it is preferably a compound having 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto:
Figure imgf000005_0002
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 form, but is not limited thereto. 2019/147074 1 »(: 1 ^ {2019/001108
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, it may be a compound having the following structure, but is not limited thereto.
Figure imgf000006_0002
본 명세서에 있어서， 실릴기는 구체적으로 트리메틸실릴기， 트리에틸실릴기， 부틸디메틸실릴기 , 비닐디메틸실릴기， 프로필디메틸실릴기， 트리페닐실릴기， 디페닐실릴기， 페닐실릴기 등이 있으나이에 한정되지 않는다. 본 명세서에 있어서， 붕소기는 구체적으로 트리메틸붕소기， 트리에틸붕소기， ^부틸디메틸붕소기， 트리페닐붕소기， 페닐붕소기 등이 있으나이에 한정되지 않는다. 본 명세서에 있어서， 할로겐기의 예로는 불소， 염소， 브롬 또는 요오드가있다. 본 명세서에 있어서， 상기 알킬기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 2019/147074 1»（：1^1{2019/001108
Figure imgf000006_0002
In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, It is not limited. In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a butyldimethylboron group, a triphenylboron group, a phenylboron group and the like. 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. Work 2019/147074 1 »(: 1 ^ {2019/001108
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 1내지 6이다. 알킬기의 구체적인 예로는 메틸， 에틸， 프로필, 11-프로필， 이소프로필， 부틸， 11-부틸， 이소부틸， 16 _부틸,
Figure imgf000007_0001
1 -메틸-부틸, 1 -에틸-부틸， 펜틸, 11-펜틸， 이소펜틸， 네오펜틸, 6!卜펜틸, 핵실, 11-핵실， 1 -메틸펜틸, 2 -메틸펜틸， 4ᅳ메틸- 2 -펜틸， 3,3 -디메틸부틸， 2 -에틸부틸， 헵틸， 11-헵틸， 1 -메틸핵실， 사이클로펜틸메틸，사이클로핵틸메틸， 옥틸, -옥틸, 라!;-옥틸, 1 -메틸헵틸，According to the embodiment, the alkyl group has 1 to 20 carbon atoms. According to another 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 alkyl groups are methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, 11-butyl, isobutyl, 1-butyl-6 _,
Figure imgf000007_0001
1-methyl-butyl, 1-ethyl-butyl, pentyl, 11-pentyl, isopentyl, neopentyl, 6卜pentyl, haeksil, 11 haeksil, 1 - methylpentyl, 2-methylpentyl, 4-eu-methyl-2 -pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, 11-heptyl, 1-methyl haeksil, cyclopentylmethyl, cyclohexyl methyl haektil, octyl-octyl, LA; - octyl, 1-methylheptyl,
2 -에틸핵실， 2 -프로필펜틸， 11-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 2내지 6이다. 구체적인 예로는 비닐, 1 -프로페닐， 이소프로페닐, 1 -부테닐, 2 -부테닐， 3 -부테닐, 1 -펜테닐,2-ethyl haeksil, 2-propyl-pentyl, 11-nonyl, 2, 2-dimethyl-heptyl, 1-ethyl-propyl, 1, 1-dimethyl-propyl, iso haeksil, 2-methyl pentyl, 4-methyl haeksil, 5- Methylhexyl, and the like, but are not limited thereto. 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,
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 있으나이들에 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 3내지 20이다. 또하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필， 사이클로부틸， 사이클로펜틸， 3 -메틸사이클로펜틸 , 2, 3 -디메틸사이클로펜틸， 사이클로핵실， 3 -메틸사이클로핵실， 4 -메틸사이클로핵실， 2,3 - 2019/147074 1»（：1^1{2019/001108 2-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl- 1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2,2-bis A naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, 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 include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 2019/147074 1 »(: 1 ^ {2019/001108
디메틸사이클로핵실， 3,4,5 -트리메틸사이클로핵실， 4 - 16!寸-부틸사이클로핵실， 사이클로헵틸， 사이클로옥틸등이 있으나， 이에 한정되지 않는다. 본명세서에 있어서， 아릴기는특별히 한정되지 않으나탄소수 6내지 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 한정되는것은아니다. 본 명세서에 있어서, 플루오레닐기는 치환될 수 있고， 치환기 2개가 서로 결합하여 스피로 구조를 형성할수 있다. 상기 플루오레닐기가치환되는 경우, Dimethyl bicyclo haeksil, 3,4,5-trimethyl-bicyclo haeksil, 4 - 1 6寸-! But include butyl cycloalkyl haeksil, cycloheptyl, cyclooctyl, and the like. 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, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group. 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 될수있다. 다만， 이에 한정되는것은아니다. 본 명세서에 있어서， 헤테로고리기는 이종 원소로 0， 比 및 중 1개 이상을 포함하는 헤테로고리기로서， 탄소수는 특별히 한정되지 않으나， 탄소수 2 내지 60인 것끼 바람직하다. 헤테로고리기의 예로는 티오펜기， 퓨란기， 피롤기， 이미다졸기， 티아졸기， 옥사졸기， 옥사디아졸기， 트리아졸기， 피리딜기 , 비피리딜기， 피리미딜기， 트리아진기， 아크리딜기， 피리다진기， 피라지닐기， 퀴놀리닐기， 퀴나졸린기， 퀴녹살리닐기 , 프탈라지닐기， 피리도 피리미디닐기， 피리도 피라지닐기， 피라지노 피라지닐기， 이소퀴놀린기， 인돌기 , 카바졸기， 벤조옥사졸기 , 벤조이미다졸기， 벤조티아졸기 , 2019/147074 1»（：1^1{2019/001108 And so on. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a heterocyclic group containing 0, a ratio and at least one hetero atom 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 pyrrolyl 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, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, 2019/147074 1 »(: 1 ^ {2019/001108
벤조카바졸기， 벤조티오펜기， 디벤조티오펜기， 벤조퓨라닐기 , 페난쓰롤린기 (1 ]161131 111 01 ， 이소옥사졸릴기， 티아디아졸릴기， 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다. 본 명세서에 있어서， 아르알킬기， 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는전술한아릴기의 예시와같다. 본명세서에 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 , 헤테로아릴텐은 2가기인 것을 제외하고는 전술한헤테로고리기에 관한설명이 적용될 수 있다. 본 명세서에 있어서， 탄화수소 고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을제외하고는전술한아릴기 또는사이클로알킬기에 관한설명이 적용될수 있다. 본 명세서에 있어서， 헤테로고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한헤테로고리기에 관한설명이 적용될 수 있다. 한편, 상기 화학식 1에서, 상기 요’ 는메틸인 것이 바람직하다. 상기 화학식 1에서, a, ， ：， 1, 6및 군는 0일수있다. 상기 화학식 1에서 , ¾내지 ¾중적어도하나는시아노일수있다. 상기 화학식 1은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나일수 있다. 2019/147074 1»（：1^1{2019/001108 Benzothiophene group, benzofuranyl group, phenanthroline group ( 1) 161131 1 11 01 , isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, etc. 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 above-mentioned aryl group. In the present specification, an aralkyl group, an alkyl The aryl group and the alkyl group in the alkylamine group are the same as the alkyl groups described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heterocyclic group. In the present specification, The alkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the explanation on the aryl group described above can be applied, except that arylene is divalent. The description of the above-mentioned heterocyclic groups can be applied, except that the heteroaryltentane is divalent. In the present specification, the hydrocarbon ring is not a monovalent hydrocarbon ring, A description about the heteroaryl group or the cycloalkyl group can be applied. 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 the two substituents are bonded to each other . In the above formula (1), it is preferable that the moiety is methyl. In formula (1), a,,, 1, 6 and groups may be 0, The above formula (1) may be any one selected from the group consisting of the following compounds. 2019/147074 1 »(: 1 ^ {2019/001108
Figure imgf000010_0001
상기 의 정의는앞서 언급한바와같다. 바람직하게는, 상기 화학식 1로 표시되는 화합물은， 하기로 구성되는 10 군으로부터 선택되는어느하나일수 있다.
Figure imgf000011_0001
Figure imgf000010_0001
The above definition is as mentioned above. Preferably, the compound represented by the above formula (1), the number of days any one selected from the group consisting of 10 to.
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000012_0001
2019/147074 1»（：1/10公019/001108 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000013_0001
Figure imgf000013_0001
상기 화학식 1로 표시되는 화합물은 하기 반응식 1과 같은 제조 방법으로제조할수 있다. 상기 제조방법은후술할제조예에서 보다구체화될 2019/147074 1»(：1/10公019/001108 The compound represented by the formula ( 1 ) can be prepared by the following reaction scheme (1). The above production method is more specific in the production example to be described later 2019/147074 1 »(: 1/10/0/0 019/001108
수있다. .
[반응식 1] [Reaction Scheme 1]
Figure imgf000014_0001
바와 같다. 상기 화학식 1로 표시되는 화합물은 상기 반응식 1을 참고하여 제조하고자하는화합물의 구조에 맞주어 줄발물질을적절히 대체하여 제조할 수있다. 또한， 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과상기 제 2전극사이에 구비된 1층 이상의 유기물층을포함하는유기 발광소자로서, 상기 유기물층중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는， 유기 발광 소자를 제공한다. 2019/147074 1»（：1^1{2019/001108
Figure imgf000014_0001
Same as. The compound represented by the formula (1) can be prepared by appropriately substituting a starting material in accordance with the structure of the compound to be prepared with reference to the Reaction Scheme 1. Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 . 2019/147074 1 »(: 1 ^ {2019/001108
본발명의 유기 발광소자의 유기물층은 단층구조로 이루어질 수도 있으나, 2층이상의 유기물층이 적층된 다층구조로이루어질수 있다. 예컨대， 본발명의 유기 발광소자는유기물층으로서 정공주입층， 정공수송층， 발광층， 전자수송층， 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다. 또한， 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공주입 및 수송층（정공 주입과 수송을 동시에 하는 층）을 포함할 수 있고， 상기 정공주입층， 정공수송층， 또는 정공주입 및 수송층은 상기 화학식 1로 표시되는화합물을포함한다. 또한， 상기 유기물 층은 발광층을 포함할 수 있고， 상기 발광층은 상기 화학식 1로표시되는화합물을포함한다. 또한, 상기 발광층은 2종 이상의 호스트를포함하고， 상기 호스트 중 하나는상기 화학식 1로표시되는화합물을포함한다. 또한, 상기 유기물 층은 전자수송층， 전자주입층， 또는 전자주입 및 수송층（전자 주입과 수송을 동시에 하는 층）을 포함할 수 있고， 상기 전자수송층, 전자주입층， 또는 전자주입 및 수송층은 상기 화학식 1로 표시되는화합물을포함한다. 또한, 상기 전자수송층， 전자주입층, 또는전자수송및주입층은상기 화학식 1로표시되는화합물을포함한다. 또한， 상기 유기물 층은 발광층 및 전자수송층을 포함하고， 상기 전자수송층은상기 화학식 1로표시되는화합물을포함할수 있다. 2019/147074 1»（：1/10公019/001108 The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. 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 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 a smaller number of organic layers. The organic material layer may include a hole injecting layer, a hole transporting layer, or a hole injecting and transporting layer (layer for simultaneously injecting and transporting holes), and the hole injecting layer, the hole transporting layer, 1 < / RTI > 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). In addition, the light-emitting layer includes two or more kinds of hosts, and one of the hosts includes a compound represented by the general formula (1). The organic material layer may include an electron transporting layer, an electron injecting layer, or an electron injecting and transporting layer (a layer simultaneously carrying electron injecting and transporting), and the electron transporting layer, the electron injecting layer, 1 < / RTI > The electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer include the compound represented by the above formula (1). The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1). 2019/147074 1 »(: 1/10/0/0 019/001108
또한， 본발명에 따른유기 발광소자는， 기판상에 양극， 1층이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일 수 있다. 또한， 본발명에 따른유기 발광소자는기판상에 음극， 1층 이상의 유기물층및 양극이 순차적으로적층된 역방향구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는도 1및 2에 예시되어 있다. 도 1은 기판 (1)， 양극 (2) , 발광층 (3)， 음극 (4)으로 이루어진 유기 발광소자의 예를도시한 것이다. 이와같은구조에 있어서， 상기 화학식 1로 표시되는화합물은상기 발광층에 포함될수 있다. 도 2는 기판 (1)， 양극 (2)， 정공주입층 (5)， 정공수송층 (6) , 於 전자저지층 (7) , 발광층 (8) , 전자수송층 (9) , 전자주입층 (10) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로표시되는화합물은상기 정공주입층， 정공수송층， 전자저지층， 발광층, 전자수송층및 전자주입층중 1층이상에 포함될수 있다. 도 3은기판 (1)， 양극 (2)， 정공주입층 (5)， 정공수송층 (6)， 발광층 (8)， 전자수송층 (9)， 전자주입 및 수송층 (11)， 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 정공주입층， 정공수송층, 발광층， 전자수송층， 및 전자주입 및수송층중 1층이상에 포함될수 있다. 본 발명에 따른 유기 발광 소자는， 상기 유기물 층 중 1층 이상이 상기 화학식 1로표시되는화합물을포함하는 것을 제외하고는당기술분야에 알려져 있는 재료와방법으로 제조될 수 있다. 또한， 상기 유기 발광소자가 복수개의 유기물층을포함하는 경우, 상기 유기물층은동일한물질 또는다른 물질로형성될수있다. 예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제 1 전극， 2019/147074 1»（：1^1{2019/001108 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 an anode, one or more organic compound layers 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 this structure, the compound represented by Formula 1 may be included in the light emitting layer. 2 is a cross-sectional view of a light emitting device according to a first embodiment of the present invention, which includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, an electron transport layer 9, ) And a cathode (4). In such a structure, the compound represented by Formula 1 may be contained in at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the electron transport layer, and the electron injection layer. Fig. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 8, an electron transporting layer 9, an electron injecting and transporting layer 11, The organic light-emitting device shown in FIG. In this structure, the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting and transporting layer. The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more 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 includes a first electrode, 2019/147074 1 »(: 1 ^ {2019/001108
유기물층 및 제 2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때， 스퍼터링법 라 塔）이나 전자범 증발법（근시 크 1011）과 같은
Figure imgf000017_0001
\¾）이· 1）03 1011）방법을 이용하여, 기관 상에 금속 또는 전도성을가지는금속산화물또는 이들의 합금을증착시켜 양극을 형성하고， 그위에 정공주입층， 정공수송층, 발광층및 전자수송층을포함하는유기물 층을형성한후， 그위에 음극으로사용할수있는물질을증착시켜 제조할수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층， 양극 물질을차례로증착시켜 유기 발광소자를만들수있다. 또한， 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공증착법 뿐만아니라용액 도포법에 의하여 유기물층으로형성될수 있다. 여기서， 용액 도포법이라 함은 스핀 코팅, 딥코팅， 닥터 블레이딩, 잉크젯 프린팅， 스크린 프린팅， 스프레이법， 롤 코팅 등을 의미하지만， 이들만으로 한정되는것은아니다. 이와 같은 방법 외에도, 기판상에 음극 물질로부터 유기물층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다（ 0 2003/012890） . 다만, 제조방법이 이에 한정되는것은아니다. 일례로， 상기 제 1 전극은 양극이고， 상기 제 2 전극은 음극이거나， 또는상기 제 1전극은음극이고， 상기 제 2전극은양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나둠, 크롬, 구리, 아연， 금과 같은 금속 또는 아들의 합금; 아연 산화물， 인듐 산화물， 인듐주석 산화물（ ⑴, 인둠아연 산화물（1쪄）과 같은 금속 산화물; ¾0:시 또는 3 2 :況와 같은 금속과 산화물의 조합; 폴리（3- 메틸티오펜）， 폴리［3, 4-（에틸렌- 1， 2 -디옥시）티오펜］作묘的 ， 폴리피롤 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 Li¾Ml과같은다층구조물질등이 있으나, 이들에만한정되는것은아니다. 상기 정공주입 물질로는전극으로부터 정공을주입하는층으로， 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 HOMOChighest occupied mol ecular orbi tal )가 양극 물질의 일함수와 주변 유기물층의 HOMO사이인 것이 바람직하다. 정공주입 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， 이들에만한정 되는것은아니다. 상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을수송받아발광층으로옮겨줄수 있는물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나， 이들에만한정되는것은아니다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 2019/147074 1»（：1^1{2019/001108 An organic material layer and a second electrode in this order. In this case, the sputtering la塔) or electronic pan evaporation (myopia greater than 1, such as 011)
Figure imgf000017_0001
\ ¾) a, 1), 03 1011) using the method, by depositing a metal or metal oxide, or an alloy thereof having a conductivity on the engine to form a cathode, and a hole injection layer, a hole transport layer, emission layer, and an electron Transporting layer, and then depositing a material that can be used as a cathode on the organic layer. In addition to such a method, an organic light emitting device can be manufactured 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, roll 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 (0 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 of sons; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (1), zinc oxide (1 fat); ¾0: during or 32: a combination of a metal and an oxide such as況; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene], conductive polymers such as polypyrrole and polyaniline, but are not limited thereto. 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 Li 占 l l, 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 on the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material due to its ability to transport holes, A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is desirable that the HOMOChighest occupied mol ecular orbital 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 organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are 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 as a hole transport material. Suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. 2019/147074 1 »(: 1 ^ {2019/001108
구체적인 예로 8 -히드록시-퀴놀린 알루미늄착물（쇼1¾）; 카르바졸 계열 화합물; 이량체화 스티릴（（1 161^ 26（1 打기） 화합물; 8시（1 ; 10 -히드록시벤조 퀴놀린_ 금속 화합물; 벤족사졸， 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리（1 페닐렌비닐렌） 1 ） 계열의 고분자; 스피로 대） 화합물; 폴리플루오렌，Specific examples include 8-hydroxy-quinoline aluminum complex (Show 1 ¾ ); Carbazole-based compounds; Dimer styryl ((1 161 ^ 26 (one-shot) compound; 8 o'clock (1; 10-hydroxybenzoquinoline metal compound; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly ( 1 -phenylenevinylene) 1) series polymer; Spiro group) compound; Polyfluorene,
5 루브렌등이 있으나, 이들에만한정되는것은아니다. 상기 발광층은호스트재료및도펀트재료를포함할수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 죽합 방향족환 유도체로는 안트라센 유도체， 피렌 유도체, 10 나프탈렌 유도체， 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고， 헤테로환 함유 화합물로는 카바졸 유도체 , 디벤조퓨란 유도체， 래더형 퓨란화합물， 피리미딘유도체등이 있으나， 이에 한정되지 않는다. 도펀트재료로는방향족아민유도체, 스트릴아민 화합물， 붕소착체， 15 플루오란텐화합물, 금속착체 등이 있다. 구체적으로방향족아민유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서 , 아릴아미노기를 갖는 피텐, 안트라센, 크리센， 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로， 아릴기, 실릴기， 알킬기, 5 rubrene, and the like, but the present invention is 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 aromatic aromatic ring derivatives include anthracene derivatives, pyrene derivatives, 10 naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds and the like. 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, 15 fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as phytenes, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compounds include substituted or unsubstituted An aryl group, a silyl group, an alkyl group, an aryl group, an aryl group,
20 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민， 스티릴디아민， 스티릴트리아민, 스티릴테트라아민등이 있으나， 이에 한정되지 않는다. 또한， 금속착체로는이리듐착체， 백금착체 등이 있으나， 이에 한정되지 않는다. A cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complexes include iridium complexes, platinum complexes and the like, but are not limited thereto.
25 상기 전자 수송 물질로는 전자주입층으로부터 전자를 수취하여 발광층까지 전자를수송하는층으로 전자수송 물질로는 음극으로부터 전자를 잘주입 받아발광층으로옮겨줄수 있는물질로서， 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8 -히드록시퀴놀린의 쇼1 착물; 시 3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나， 25, the electron transport material include a receives the electronic electron transport material with a layer of transporting electrons to the light emitting layer receives electrons from the cathode as a substance that give toward the light emitting layer, the electron mobility larger material from the electron injection layer Is suitable. Specific examples include show 1 complexes of 8-hydroxyquinoline; Complexes containing poem 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like,
30 이들에만한정되는 것은 아니다. 전자수송층은종래기술에 따라사용된 바와 2019/147074 1»（：1^1{2019/001108 30 is not limited only to these. The electron transporting layer may be a < RTI ID = 0.0 > 2019/147074 1 »(: 1 ^ {2019/001108
같이 임의의 원하는캐소드물질과함께 사용할수 있다. 특히, 적절한캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘， 바륨, 칼슘， 이테르븀 및 사마륨이고， 각경우알루미늄층또는실버층이 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［비퀴놀리나토）베릴륨， 비스（ 10 -하이드록시벤조［비퀴놀리나토）아연 , 비스（2 -메틸- 8- 퀴놀리나토）클로로갈륨， 비스（ 2 -메틸- 8 -퀴놀리나토）（ 0 -크레졸라토）갈륨， 비스（2 -메틸- 8 -퀴놀리나토）（ 1 -나프톨라토）알루미늄 , 비스（2 -메틸- 8- 퀴놀리나토）（2 -나프톨라토）갈륨등이 있으나， 이에 한정되지 않는다. 본발명에 따른유기 발광소자는사용되는재료에 따라전면 발광형， 후면발광형 또는양면 발광형일수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양전지 또는유기 트랜지스터에 포함될수 있다. 2019/147074 1»（：1^1{2019/001108 As well as any desired cathode material. 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, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10 -hydroxybenzo [ Bis (2-methyl-8-quinolinato), bis (2-methyl-8-quinolinato) ( 0 -cresolato ), Gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) . 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. 2019/147074 1 »(: 1 ^ {2019/001108
이하， 발명의 이해를 돕기 위하여 바람직한 실시예들이 제시된다. 그러나 하기의 실시예들은 본 발명을 예시하기 위한 것일 뿐， 본 발명을 이들만으로한정하는것은아니다. Best Mode for Carrying Out the Invention Hereinafter, preferred embodiments are shown to facilitate understanding of the present invention. However, the following examples are intended to illustrate the present invention without limiting it thereto.
［제조예］ [Manufacturing Example]
제조예 1： 중간체사의 제조  Preparation Example 1: Preparation of intermediate product
Figure imgf000021_0001
질소 분위기에서 5001111 둥근 바닥 플라스크에 2 -클로로- 4-（4- 클로로페닐）- 6 -페닐- 1,3, 5 -트리아진（15.0용， 49.64_01）， 디벤조比 ］티오펜- 4- 일보론산（11.3§， 49.64_01）을테트라하이드로퓨란 21（½1에 완전히 녹인후 탄산칼륨수용액（150미1）을 첨가하고, 테트라키스-（트리페닐포스핀）팔라듐（1.¾, 1.49^101）을 넣은 후 6 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에탄올 250 로 재결정하여 상기 화합물 사
Figure imgf000021_0002
수율: 94%）을 제조하였다（¾13［¾1+비+= 450）. 제조예 2：중간체 의 제조 2019/147074 1»(：1/10公019/001108
Figure imgf000022_0001
Figure imgf000021_0001
500 1111 round bottom flask under nitrogen 2-chloro-4- (4-chlorophenyl) - 6-phenyl-1, 3, 5-triazine (, 49.64_ 01 for 15.0), dibenzo比] thiophene- 4 Daily acid (11.3 §, 49.64_ 01) of tetrahydrofuran 21 (after completely dissolved in ½1 potassium carbonate solution (150 mi 1), tetrakis- (triphenylphosphine) palladium (1.¾, 1.49 < / RTI > 101 ) was added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethanol 250 to obtain
Figure imgf000021_0002
Yield: 94%) was prepared (13 13 (1 1 + non + = 450). Production Example 2: Preparation of Intermediate 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000022_0001
46.89_01)에 비스 (피나콜라토)디보론 (13.1용, 51.581^101 ) , ?<1(<¾크)2 (0.8요， 1.41_01)， 灰¾¾ (0.8용, 2.81^01) , 0 (13.8묘, 140.68^1101)를 디옥세인Bis (pinacolato) diboron (for 13.1, 51.58 1 ^ 10 1) ,? <1 (<¾ size) 2 (0.8 yo, 1.41_ 0, 1), for灰¾ ¾ (0.8 to 1 46.89_ 0) , 2.81 ^ 0: 1), 0 (13.8 mu, 140.68 ^ 110 1) hexanes-dioxide
300此에 넣고 환류하여 2사간동안 교반했다. 四比를 통해 반응 종결을 확인 한뒤 필터하여 336를 제거하고 용액을 감압농축했다. 이것을期 (：13녹여서 완전히 물로 씻어 주고 생성물이 녹아있는 용액을 감압 농죽하고 에탄올을 이용하여 재결정하여 상기 화합물 요2 (21.1§ 수율 83%)를 제조하였다 (¾保［¾1+비+= 542) 제조예 3： 중간체쇼3의 제조 300, and the mixture was refluxed and stirred for 2 hours. After confirming the completion of the reaction through the four ratio, 336 was removed by filtration, and the solution was concentrated under reduced pressure. This期(: 1 3 dissolved to prepare a fully washed with water nongjuk reduced pressure and the solution with the product was dissolved and recrystallized using ethanol to yaw the compound 2 (21.1 § yield 83%) (¾保[¾1 + Non + = 542) Production Example 3: Preparation of intermediate show 3
Figure imgf000022_0002
질소 분위기에서 止 둥근 바닥 플라스크에 화합물 쇼2 (21.1§, 8.97_01), 1 -브로모- 2 -니트로벤젠 (8.7용, 42.86,01)을 테트라하이드로퓨란 00미1에 완전히 녹인 후 2 탄산칼륨수용액 (60 )을 첨가하고， 테트라키스 2019/147074 1»（：1/10公019/001108
Figure imgf000022_0002
Compound show 2 (21.1 §, 8.97_ 0 1) and 1-bromo-2-nitrobenzene (8.7, 42.86, 0 1) were completely dissolved in tetrahydrofuran 00 μl in a round bottom flask under nitrogen atmosphere 2 aqueous potassium carbonate solution (60) was added, tetrakis 2019/147074 1 »(: 1/10/0/0 019/001108
（트리페닐포스핀）팔라듐（1.4용， 1. 1711111101）을 넣은 후 24시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물층을 제거하고 무수황산마그네슘으로 건조한후감압농축시키고에탄올 250 로재결정하여 상기 화합물요3 （17.4§, 수율: 83%）을제조하였다 1\1+}1］+= 537） 제조예 4： 중간체쇼4의 제조 (Triphenylphosphine) palladium (1.4 eq, 1.1711111101) was added thereto, followed by heating and stirring for 24 hours. It cooled to room temperature, removing the water layer, and 3 (17.4 §, yield: 83%) of the compound I is concentrated under reduced pressure after dried over anhydrous magnesium sulfate and recrystallized with ethanol to 250 was prepared in a 1 \} 1 + 1] + = 537) Production Example 4: Preparation of intermediate show 4
Figure imgf000023_0001
Figure imgf000023_0001
A3 4 A3 4
질소 분위기에서 止 둥근 바닥 플라스크에 화합물 쇼3 （17Ag 32.43 101）에 트리에틸포스파이트 （1001此, 580.3_01）을첨가하고 3시간동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 고체를 얻고 이를 물로 씻어준다. 얻은 화합물을 건조하여 화합물 요4 （11.3용, 수율: 69%）를 제조하였다 3［1\1내］+= 505） Was added triethyl phosphite (100 1此, 580.3_ 01) the compound in止round bottom flask under nitrogen show 3 (17Ag 32.43 101), and the resulting mixture was stirred under heating for 3 hours. Lower the temperature to room temperature and filter to obtain a solid and wash it with water. The obtained compound was dried to obtain Compound 4 (11.3, yield: 69%). 3 [1 + 1] + = 505)
［실시예］ [Example]
실시예 1： 화합물 1의 제조  Example 1: Preparation of Compound 1
Figure imgf000023_0002
질소 분위기에서 比 둥근 바닥 플라스크에 화합물 쇼4 （11.3용, 2019/147074 1»（：1/10公019/001108
Figure imgf000023_0002
To a round bottom flask in nitrogen atmosphere was added compound 4 (11.3, 2019/147074 1 »(: 1/10/0/0 019/001108
22.39_01), 2 -브로모디벤조比 ］티오펜 (6.1당， 23.51_01)， 소듐 터트- 부톡사이드 (4.3용, 44.79_01)에 자일렌 20이를 첨가한 뒤 비스 (트리-터트- 부틸포스핀)팔라듐 (0) (0.1§， 0.22_01)을 넣고 1시간동안가열 교반하였다. 상온으로 온도를 낮추고 필터하여 고체를 얻고 이를 물로 씻어준다. 얻은 화합물을건조하여 화합물 1 (5.7§ 수율: 37%)를제조하였다 아¾«1］+= 687). 실시예 2： 화합물 2의 제조
Figure imgf000024_0001
2 -브로모디벤조比,1］티오펜 대신 4 -브로모디벤조比 ］티오펜을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한 방법으로 화합물 2를 제조하였다 3［1\1+비+= 687). 실시예 3： 화합물 3의 제조 22.39_ 0 1), 2-bromo-modify-benzo比] thiophene (6.1 per 23.51_ 0 1), sodium tert-butoxide (4.3, 0 44.79_ 1) xylene back-bis (tri-20 was added to this, for - tert-butyl put phosphine) palladium (0) (0.1 §, 0.22_ 0 1) was stirred under heating for 1 hour. Lower the temperature to room temperature and filter to obtain a solid and wash it with water. Dry the obtained compound Compound 1 was prepared (5.7 § yield 37%) of O ¾ «1] + = 687) . Example 2: Preparation of compound 2
Figure imgf000024_0001
2-bromo-modify-benzo比, 1] thiophene instead of 4-bromo-modify-benzo比] was prepared and the same procedure as compound 2, and a process for preparing a compound 1, except for using thiophene-3 In 1 \ 1 + Non + = 687). Example 3: Preparation of Compound 3
Figure imgf000024_0002
Figure imgf000024_0002
것을 제외하고 화합물 1을 제조하는 방법과 동일한 방법으로 화합물 3을 제조하였다 (¾¾¾+!1］+= 687). \¥0 2019/147074 ! ：1710公019/001108 And the compound 3 in the same method as that for preparing the compound 1 was prepared (¾¾¾ +! 1] + = 687) , except that. \ ¥ 0 2019/147074! : 1710 公 019/001108
실시예 4： 화합물 4의 제조 Example 4: Preparation of compound 4
Figure imgf000025_0001
Figure imgf000025_0001
4 화합물 쇼4와 2 -브로모디벤조比,（1］티오펜 대신 1-（4- （디벤조比,（1］티오펜- 4 -일）- 6 -페닐- 1,3, 5 -트리아진- 2 -일）-에-카바졸과 3 - 브로모디벤조比 ］티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 4를제조하였다어3 +비+= 687）. 실시예 5： 화합물 5의 제조 4 compound with 4 and 2-bromodibenzo ratios, (1) 1 - (4- (dibenzoic ratio, (1) thiophene-4-yl) -6- triazin-2-yl) - a-carbazole and 3-bromo-modify-benzo比] compound 1 was prepared for compound 4 in the same manner as how to make and, except for using thiophene-control 3 + non + = 687). Example 5: Preparation of compound 5
Figure imgf000025_0002
Figure imgf000025_0002
3 -브로모디벤조比 ］티오펜 대신 2 -브로모디벤조比，（1］티오펜을 사용한 것을 제외하고 화합물 4를 제조하는 방법과 동일한 방법으로 화합물 5를 제조하였다 아¾!대］+= 687）. 실시예 6： 화합물 6의 제조 2019/147074 1»（：1/10公019/001108
Figure imgf000026_0001
화합물 쇼4와 2 -브로모디벤조［13 , (1］티오펜 대신 3-(4-(디벤조 比 , (1］티오펜- 4 -일 )-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일)-에-카바졸과 4 - 브로모디벤조［13 ］티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 6을제조하였다 (¾恨［¾1+11］+= 687) . 실시예 7： 화합물 7의 제조 3-bromo-modify-benzo比] thiophene instead of 2 - bromo-modify-benzo比, (1] was prepared in the compound 5 in the same way to manufacture the compound 4 except for using thiophene-O ¾ versus] + = 687 ). Example 6: Preparation of compound 6 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000026_0001
Compound show 4 and 2-bromodibenzo [ 13, ( 1) thiophene instead of 3- (4- (dibenzo r, 1) thiophen- Compound 6 was prepared in the same manner as Compound 1 except that 4-bromodibenzo [l, 3 ] thiophene was used instead of 4-bromo-2- (4- 11] + = 687). Example 7: Preparation of compound 7
Figure imgf000026_0002
화합물 쇼4와 2 -브로모디벤조 0,(1］티오펜 대신 3-(4-
Figure imgf000026_0002
Compound show 4 and 2-bromodibenzo-O, ( 1) 3- (4-
(디벤조比， (1］티오펜- 4 -일 )-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일 )-애_카바졸과 3 - 브로모디벤조［1),(1］티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 7을제조하였다 3»+비+= 687) . 실시예 8： 화합물 8의 제조 2019/147074 1»（：1/10公019/001108 (Dibenzo-ratio, ( 1) thiophen-4-yl) -6-phenyl-1,3,5-triazin- ] to manufacture the compound 1, except for using thiophene and the compound 7 was prepared in the same manner 3 »+ non + = 687). Example 8: Preparation of compound 8 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000027_0001
화합물 요4와 2 -브로모디벤조에］티오펜 대신 3-(4-
Figure imgf000027_0001
Compound (4) and 2- (bromodibenzoate) thiophene were used instead of 3- (4-
(디벤조比 , 1］티오펜- 4 -일 )-6 -페닐 1 , 3 , 5 -트리아진- 2 -일 )-9} 카바졸과 1 - 브로모디벤조比, 1］티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 8을제조하였다 (1此［1+}1］+= 687) . 실시예 9： 화합물 9의 제조 (1) thiophene-4-yl) -6-phenyl 1,3,5-triazine-2-yl) -9} carbazole and 1-bromodibenzo ratio, Compound 8 was prepared in the same manner as Compound 1 was prepared (1 [1 +} 1] + = 687). Example 9: Preparation of Compound 9
Figure imgf000027_0002
화합물 쇼4와 2 -브로모디벤조［ 비티오펜 대신 4-(4 -
Figure imgf000027_0002
Compound show 4 and 2-bromodibenzo [4- (4-
(디벤조比，1］티오펜- 4 -일 )-6 -페닐- 1， 3 , 5 -트리아진- 2 -일 )-抑-카바졸과 4 - 브로모디벤조［1), 1］티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 9을제조하였다 (¾松 +1!］+= 687) . 실시예 10: 화합물 10의 제조 2019/147074 1»（：1/10公019/001108 (Dibenzo r, 1] thiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -sup-carbazole and 4-bromodibenzo [ was except that thiophene was prepared in the same manner as compound 9, and a process for preparing a compound 1 (¾松+1!] + = 687). Example 10: Preparation of compound 10 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000028_0001
화합물 쇼4와 2 -브로모디벤조比, <1]티오펜 대신 4-（4-
Figure imgf000028_0001
Compound show 4 and 2-bromodibenzo ratio, <1> 4- (4-
（디벤조比 ,（1]티오펜- 4 -일）- 6 -페닐- 1， 3 , 5 -트리아진- 2 -일）-애-카바졸과 2- 브로모디벤조 [13 ,（1]티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 10을제조하였다 아 +비 687）. 실시예 11: 화합물 11의 제조 (Dibenzo-ratio, (1) thiophen-4-yl) -6-phenyl-1,3,5-triazin- Compound 10 was prepared in the same manner as Compound 1 except that thiophene was used. Example 11: Preparation of compound 11
Figure imgf000028_0002
화합물 쇼4와 2 -브로모디벤조比 ]티오펜 대신 4-（4-
Figure imgf000028_0002
Compound show 4 and 2-bromodibenzoide] The title compound was obtained in the same manner as in 4- (4-
（디벤조比 ,（1]티오펜- 4 -일）- 6 -페닐- 1， 3， 5 -트리아진- 2 -일）-에-카바졸과 1 - 브로모디벤조比,到티오펜을사용한것을제외하고화합물 1을제조하는방법과 동일한방법으로화합물 11을제조하였다 3[¾1태]+= 687）. 실시예 12: 화합물 12의 제조 2019/147074 1»(：1/10公019/001108 (Dibenzo ratio, (1) thiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -e-carbazole and 1-bromodibenzo ratios, Compound 11 was prepared in the same manner as Compound 1 except for using 3 [tert-butyl] + = 687). Example 12: Preparation of Compound 12 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000029_0001
화합물 쇼4와 2 -브로모디벤조［ 到티오펜 대신 1-（4-
Figure imgf000029_0001
Compound show 4 and 2-bromodibenzo [1- (4-
（디벤조比 ,（1］티오펜- 4 -일）-6 -페닐- 1， 3 , 5 -트리아진- 2 -일）-예-카바졸과 4- 브로모디벤조比세퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 12를제조하였다（¾1 ^비+= 671）. 실시예 13: 화합물 13의 제조
Figure imgf000029_0002
화합물 쇼4와 와 2 -브로모디벤조［13 ,（1］티오펜 대신 1-(4-(Dibenzo ratio, (1) thiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -Y-carbazole and 4-bromodibenzo in the same way except that the manufacturing of the compound 1 was prepared in the compound 12 (¾1 ^ ratio + = 671). Example 13: Preparation of compound 13
Figure imgf000029_0002
Compound show 4 and 2-bromodibenzo [ 13, l- (4-
（디벤조［13 ,（1］티오펜- 4 -일）- 6 -페닐- 1 ,3 , 5 -트리아진- 2 -일）- 911-카바졸과 2 브로모디벤조比 ,（1］퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 13을제조하였다 +비 671）. 실시예 14: 화합물 14의 제조 2019/147074 1»（：1/10公019/001108 (Di-benzo [1, 3, (1] thiophen-4-yl) - 6-phenyl-1, 3, 5-triazine-2-yl) - 911- carbazole and 2-bromo-modify-benzo比, (1 Compound 13 was prepared in the same manner as compound 1 except that furan was used. Example 14: Preparation of compound 14 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000030_0001
Figure imgf000030_0001
（디벤조比 ,비티오펜- 4 -일）- 6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）-애-카바졸과 3- 브로모디벤조［）3 ,（1］퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 14를제조하였다 +비 671）. 실시예 15: 화합물 15의 제조 A carbazole with 3-bromo-modify-benzo [3) 3, (1] furan - (dibenzo比, bithiophene-4-yl) - 6-phenyl-1, 3, 5-triazine-2-yl) - Ke Compound 14 was prepared in the same manner as Compound 1 was prepared except for using Compound 671). Example 15: Preparation of compound 15
Figure imgf000030_0002
화합물 쇼4와 2 -브로모디벤조比 ］티오펜 대신 2-（4-
Figure imgf000030_0002
Compound show 4 and 2-bromodibenzoide] 2- (4-
（디벤조比 ,（1］티오펜- 4 -일）-6 -페닐- 1， 3 , 5 -트리아진- 2 -일）-예-카바졸과 2 - 브로모디벤조［ 비퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 15를제조하였다（1將［¾1+}1］+= 671）. 실시예 16: 화합물 16의 제조 (Dibenzo ratio, (1) thiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -Y- carbazole and 2-bromodibenzo [bifuran Compound 1 was prepared in the same manner as Compound 1 except that (1-tert-butylphenol + 1) + = 671). Example 16: Preparation of Compound 16
Figure imgf000030_0003
2019/147074 1»（：1^1{2019/001108
Figure imgf000030_0003
2019/147074 1 »(: 1 ^ {2019/001108
화합물 쇼4와 2 -브로모디벤조［13，（1］티오펜 대신 2-（4-Compound show 4 and 2-bromodibenzo [ 13 , (1) 2- (4-
（디벤조比 ,비티오펜- 4 -일）- 6 -페닐- 1， 3 , 5 -트리아진- 2 -일）-예_카바졸과 1 - 브로모디벤조［1）,（1］퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 16을제조하였다어마 +비 671）. 실시예 17: 화합물 17의 제조
Figure imgf000031_0001
화합물 쇼4와 2 -브로모디벤조［13 ,（1］티오펜 대신 3-（4-1-bromodibenzo [1], (1) furan-2-yl) -bis Compound 16 was prepared in the same manner as Compound 1 was prepared except that it was used. Example 17: Preparation of compound 17
Figure imgf000031_0001
Compound show 4 and 2-bromodibenzo [ 13, (1) 3- (4-
（디벤조比，（1］티오펜- 4 -일）- 6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）-에_카바졸과 4 - 브로모디벤조［¾>，（!］퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 17을제조하였다（¾1 ¾1내］+= 671）. 실시예 18: 화합물 18의 제조
Figure imgf000031_0002
화합물 요4와 2 -브로모디벤조比,（1］티오펜 대신 3-（4-(Dibenzo比, (1] thiophen-4-yl) - 6-phenyl-1, 3, 5-triazine-2-yl) - a _ carbazole and 4-bromo-modify-benzo [¾>, (! ] Furan, Compound 17 was prepared in the same manner as Compound 1 was prepared (in 1/1, 1/1) + = 671). Example 18: Preparation of compound 18
Figure imgf000031_0002
Bromodibenzoic ratio of compound (4) and (3) (4-
（디벤조［ , <1］티오펜- 4 -일）-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）-911-카바졸과 2- 브로모디벤조［13 ,（1］퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 18을제조하였다 라 비+= 671）. 실시예 19: 화합물 19의 제조 2019/147074 1»（：1/10公019/001108 (1, 3, 5-triazin-2-yl) -911-carbazole and 2-bromodibenzo [13, a method for preparing a furan, except for using compound 1 and compound 18 in the same way was prepared the non-La + = 671). Example 19: Preparation of compound 19 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000032_0001
화합물 쇼4와 2 -브로모디벤조 [1,1]티오펜 대신 4-(4-
Figure imgf000032_0001
Compound Scheme 4 and 4- (4-tert-butyldimethylsilyloxy)
(디벤조比 ,비티오펜- 4 -일 )-6 -페닐- 1， 3 , 5 -트리아진- 2 -일 )-예-카바졸과 4- 브로모디벤조比,1]퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 19를제조하였다 아 +비 671). 실시예 20： 화합물 20의 제조 (Dibenzo ratio, bithiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -e-carbazole and 4-bromodibenzo ratio, 1] furan Compound 19 was prepared in the same manner as Compound 1 was prepared. Example 20: Preparation of compound 20
Figure imgf000032_0002
화합물 요4와 2 -브로모디벤조比,1]티오펜 대신 4-(4-
Figure imgf000032_0002
Compound 4 and 2-bromodibenzoic ratio, 1] 4- (4-
(디벤조比 ,1]티오펜- 4 -일 )-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일 )-에_카바졸과 3 - 브로모디벤조比 ]퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 20을제조하였다 아¾1+비+= 671). 실시예 21： 화합물 21의 제조 (Dibenzo r, 1] thiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -hexaborazole and 3-bromodibenzo ratio] furan how to manufacture the compound 1 and compound 20 were prepared in the same manner ah ¾1 + non + = 671). Example 21: Preparation of compound 21
Figure imgf000032_0003
2019/147074 1»（：1/10公019/001108
Figure imgf000032_0003
2019/147074 1 »(: 1/10/0/0 019/001108
화합물 쇼4와
Figure imgf000033_0001
대신 4-（4-Compound show 4 and
Figure imgf000033_0001
Instead, 4- (4-
（디벤조比 ,비티오펜- 4 -일）- 6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）-애_카바졸과 1 - 브로모디벤조比 ]퓨란을 사용한 것을 제외하고 화합물 1을 제조하는 방법과 동일한방법으로화합물 21을제조하였다（1狀 +비+= 671）. 실시예 22： 화합물 22의 제조 (Dibenzo ratio, bithiophen-4-yl) -6-phenyl-1,3,5-triazine-2- Compound 1 was prepared in the same manner as Compound 1 (1 type + ratio + 671). Example 22: Preparation of compound 22
Figure imgf000033_0002
화합물 요4와 2 -브로모디벤조比 ]티오펜 대신 1-（4- （디벤조比，到티오펜- 4 -일）- 6 -페닐- 1,3, 5 -트리아진- 2 -일）-애-카바졸과 1 - 브로모- 9 ,9 -디메틸-에-플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 22를제조하였다 아 +비 697）. 실시예 23： 화합물 23의 제조
Figure imgf000033_0002
Phenyl-1,3,5-triazin-2-yl) thiophene instead of 1- (4- (dibenzo r, a thiophen-4-yl) Compound 69 was prepared in the same manner as compound 1, except that 1-bromo-9-methoxy-9-methoxy-benzenesulfonyl chloride and 1-bromo-9,9- dimethyl-e-fluorene were used. Example 23: Preparation of Compound 23
Figure imgf000033_0003
화합물 요4와 2 -브로모디벤조 [13 ,（1]티오펜 대신 1-（4-
Figure imgf000033_0003
Compound (4) and 2-bromodibenzo [ 13, (1) 1- (4-
（디벤조比 ,則티오펜- 4 -일）-6 -페닐- 1， 3 , 5 -트리아진- 2 -일）-抑_카바졸과 3 - 2019/147074 1»（：1/10公019/001108 (Dibenzo r, thiophene-4-yl) -6-phenyl-1,3,5-triazin-2-yl) 2019/147074 1 »(: 1/10/0/0 019/001108
브로모- 9, 9 -디메틸-에_플루오텐을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 23을제조하였다여 ¾1+비+= 697) . 실시예 24： 화합물 24의 제조
Figure imgf000034_0001
화합물 쇼4와 2 -브로모디벤조 [1 , 1]티오펜 대신 2-(4-Bromo-9, 9-dimethyl-on and open the compound 1, except for using X-fluoro _ was prepared in the same manner as compound 23 and the method for producing a non-¾1 + + = 697). Example 24: Preparation of Compound 24
Figure imgf000034_0001
Compound Scheme 4 and 2-bromodibenzo [l, l] thiophene in place of 2- (4-
(디벤조比 , (1]티오펜- 4 -일 )-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일 )-에_카바졸과 1 - 브로모- 9, 9 -디메틸-에_플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 24를제조하였다 3¾+비+= 697) . 실시예 25： 화합물 25의 제조
Figure imgf000034_0002
화합물 요4와 2 -브로모디벤조比，비티오펜 대신 2-(4-(Dibenzoic ratio, (1) thiophen-4-yl) -6-phenyl-1,3,5-triazin- to develop, except for using the fluorene compound 1 and compound 24 were prepared by the same method as that for preparing non-3¾ + + = 697). Example 25: Preparation of compound 25
Figure imgf000034_0002
Compound 4 and 2-bromodibenzoate, instead of bithiophene, 2- (4-
(디벤조比，비티오펜- 4 -일)- 6 -페닐- 1， 3， 5 -트리아진- 2 -일 )-抑_카바졸과 2 - 브로모- 9, 9 -디메틸-抑-플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 25를제조하였다 (¾6 +비+= 697) . 실시예 26： 화합물 26의 제조 2019/147074 1»（：1/10公019/001108
Figure imgf000035_0001
화합물 쇼4와 2 -브로모디벤조 [ 비티오펜 대선 2-(4-(Dibenzo ratio, bithiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -down carbazole and 2-bromo-9,9- and the compound 1, except that the fluorene compound 25 was prepared by the same method as that for preparing (+ ¾6 ratio + = 697). Example 26: Preparation of compound 26 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000035_0001
Compound show 4 and 2-bromodibenzo [bithiophene preselected 2- (4-
(디벤조比，1]티오펜- 4 -일)- 6 -페닐- 1 , 3， 5 -트리아진- 2 -일 )-에-카바졸과 4- 브로모- 9, 9 -디메틸-抑-플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 26을제조하였다 31＞내]+= 697) . 실시예 27： 화합물 27의 제조
Figure imgf000035_0002
화합물 쇼4와 2 -브로모디벤조 [1 , 1]티오펜 대신 3-(4-(Dibenzo r, 1] thiophen-4-yl) -6-phenyl-1,3,5-triazin- 2- yl) -e-carbazole and 4-bromo-9,9- - fluorenyl how except that the fluorene to prepare compound 1 and compound 26 in the same manner was prepared 31> I] + = 697). Example 27: Preparation of compound 27
Figure imgf000035_0002
Compound Scheme 4 and 3- (4-tert-butoxycarbonylamino) pyridine instead of 2-bromodibenzo [1,1]
(디벤조比 , 1]티오펜- 4 -일 )-6 -페닐- 1 , 3， 5 -트리아진- 2 -일)-에_카바졸과 2 - 브로모- 9 ,9 -디메틸-抑-플루오텐을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 27을제조하였다 0此[¾1+비+= 697) . 실시예 28： 화합물 28의 제조
Figure imgf000035_0003
(Dibenzoic ratio, 1] thiophen-4-yl) -6-phenyl-1,3,5-triazin- 2- yl) -ethoxazole and 2-bromo-9,9- - how to manufacture the compound 1, except for using X-fluoro and the compound was prepared in the same way 27 0此[¾1 + non + = 697). Example 28: Preparation of compound 28
Figure imgf000035_0003
28 화합물 A4와 2 -브로모디벤조 [b，d]티오펜 대신 3-（4-28 Compound (A4) and 3- (4-tert-butyldibenzo [b, d]
（디벤조 [b， d]티오펜- 4 -일）-6 -페닐- 1， 3， 5 -트리아진- 2 -일）- 9H-카바졸과 3 - 브로모- 9, 9 -디메틸- 9H-플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 28을제조하였다（MS[M+H]+= 697）. 실시예 29： 화합물 29의 제조 (Dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazin- Compound 28 was prepared (MS [M + H] &lt; + &gt; = 697) in the same manner as Compound 1 except for using 9H-fluorene. Example 29: Preparation of compound 29
Figure imgf000036_0001
Figure imgf000036_0001
29 화합물 쇼4와 2 -브로모디벤조比 ]티오펜 대신 4-（4- 29 Compound Scheme 4 and 2-bromodibenzoide] 4- (4-
（디벤조比 ,（1]티오펜- 4 -일）-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）-卵-카바졸과 2 - 브로모- 9, 9 -디메틸- 911-플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 29를제조하였다 3[¾1내]+= 697）. 실시예 30： 화합물 30의 제조 (Dibenzoic ratio, (1) thiophen-4-yl) -6-phenyl-1,3,5-triazin- and the compound 1, except for using 911- fluorene was prepared compound 29 by the same method as that for producing 3 [¾1 I] + = 697). Example 30: Preparation of compound 30
Figure imgf000036_0002
Figure imgf000036_0002
30 화합물 쇼4와 2 -브로모디벤조 [!），（!]티오펜 대신 4-（4- 30 Compound Scheme 4 and 2-bromodibenzo [!), 4- (4-
（디벤조比，到티오펜- 4 -일）-6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）-예-카바졸과 4- 브로모- 9 ,9 -디메틸-抑-플루오렌을사용한 것을 제외하고 화합물 1을 제조하는 방법과동일한방법으로화합물 30을제조하였다（¾保[!«+}{]+= 697）. 2019/147074 1»（：1/10公019/001108 (Dibenzo ratios, all thiophen-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -methanone and 4-bromo-9,9- fluorenyl how except that the fluorene to prepare compound 1 and compound 30 in the same way was prepared (¾保[! «+} {] + = 697). 2019/147074 1 »(: 1/10/0/0 019/001108
실시예 31： 화합물 31의 제조 Example 31: Preparation of compound 31
Figure imgf000037_0001
화합물 쇼4 대신 화합물 요4_1을 사용한 것을 제외하고 화합물 1을 제조하는방법과동일한방법으로화합물 31을제조하였다 으 +비 712）. 실시예 32： 화합물 32의 제조
Figure imgf000037_0001
Compound 31 was prepared in the same manner as Compound 1 except that Compound 4-1 was used instead of Compound 4. Example 32: Preparation of compound 32
Figure imgf000037_0002
화합물 쇼4와 2 -브로모디벤조比 ,（1］티오펜 대신 3-（4-
Figure imgf000037_0002
Compound show 4 and 2-bromodibenzo ratio, (1) 3- (4-
（디벤조比 ］티오펜- 4 -일）- 6 -페닐- 1,3, 5 -트리아진- 2 -일）-애-카바졸과 8 - 브로모디벤조比，（1］티오펜- 2 -카보니트릴을 사용한 것을 제외하고 화합물 1을 제조하는방법과동일한방법으로화합물 32를제조하였다（¾犯［¾1대］+= 712）. 실시예 33： 화합물 33의 제조 (1) thiophene-2 (dibenzoyl) thiophene-4-yl) -6-phenyl-1,3,5-triazine- -Carbenitrile, Compound 32 was prepared (compound [1] = + 712). Example 33: Preparation of compound 33
Figure imgf000037_0003
2019/147074 1»（：1/10公019/001108
Figure imgf000037_0003
2019/147074 1 »(: 1/10/0/0 019/001108
화합물 요4와 2 -브로모디벤조比,비티오펜 대신 3-（4-Compound 4 and 2-bromodibenzoate were used instead of 3- (4-
（디벤조比 ,（1]티오펜- 4 -일）-6 -페닐- 1 , 3 5 -트리아진- 2 -일）-에_카바졸과 6 - 브로모디벤조 [1）,（1]티오펜- 3 -카보니트릴을 사용한 것을 제외하고 화합물 1을 제조하는방법과동일한방법으로화합물 33을제조하였다 아¾1+11]+= 712）. 실시예 34： 화합물 34의 제조
Figure imgf000038_0001
화합물 요4 대신 화합물 쇼4-2를 사용한 것을 제외하고 화합물 21을 제조하는방법과동일한방법으로화합물 34를제조하였다 3[1\«1]+= 696）. 실시예 35： 화합물 35의 제조
Figure imgf000038_0002
화합물 쇼4와 2 -브로모디벤조比 ]티오펜 대신 3-（4-(1), (1), (2), (3), (4) and (6) thiophene-3-the same method as compound 33 with the exception that the method for preparing a hydrochloride of compound 1 was prepared ah ¾1 + 11] + = 712) . Example 34: Preparation of compound 34
Figure imgf000038_0001
Compound 34 was prepared in the same manner as Compound 21 except that Compound Scheme 4-2 was used instead of Compound Scheme 4: 3 [1 \ 1] + = 696. Example 35: Preparation of compound 35
Figure imgf000038_0002
Compound show 4 and 2-bromodibenzoide] The title compound was obtained in the same manner as 3- (4-
（디벤조比（1]티오펜- 4 -일）-6 -페닐- 1 3 5 -트리아진- 2 -일）-抑_카바졸과 7 - 브로모디벤조比 ]퓨란- 2 -카보니트릴을 사용한 것을 제외하고 화합물 1을 제조하는방법과동일한방법으로화합물 35를제조하였다 ¼대]+= 696）. 실시예 36： 화합물 36의 제조 2019/147074 1»（：1/10公019/001108 (Dibenzoic ratio (1) thiophene-4-yl) -6-phenyl-1,3,5-triazin-2-yl) -down carbazole and 7-bromodibenzoic acid] furan-2-carbonitrile and compound 1 was prepared in the compound 35 in the same method as that for preparing for ¼] + = 696), except for using. Example 36: Preparation of compound 36 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000039_0001
화합물 쇼4와 2 -브로모디벤조比，（1]티오펜 대신 3-（4-
Figure imgf000039_0001
Compound show 4 and 2-bromodibenzo ratio, (1) 3- (4-
（디벤조比 ,（1]티오펜- 4 -일）-6 -페닐ᅳ 1 , 3 , 5 -트리아진- 2 -일）-抑_카바졸과 8- 브로모디벤조比，비퓨란- 2 -카보니트릴을 사용한 것을 제외하고 화합물 1을 제조하는방법과동일한방법으로화합물 36을제조하였다 3[¾1+비+= 696）. (Dibenzo ratio, (1) thiophen-4-yl) -6-phenylphenyl 1,3,5-triazin-2-yl) -down carbazole and 8-bromodibenzoic ratio, -carbonitrile was, except for using the nitrile to produce the compound 36 in the same method as that for preparing the compound 1 3 [¾1 + non + = 696).
[실험예] [Experimental Example]
실험예 1-1 Experimental Example 1-1
이^ 1;比 0 （3근）가 1，300ᅀ의 두께로 박막코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때， 세제로는 피셔사어 此라 00.） 제품을사용하였으며， 증류수로는 밀리포어사（ 11 0 00.） 제품의 필터（ 라）로 2차로걸러진 증류수를사용하였다. 打0를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 1◦분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간세정한후진공증착기로기판을수송시켰다. 상기와같이 준비된 1 0투명 전극위에 하기 111-1 화합물을 50入의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 117-1 화합물을 250쇼의 두께로 열 진공 증착하여 정공수송층을 형성하고， 1^1-1 증착막 위에 하기 난 -2 화합물을 50人 두께로 진공 증착하여 전자저지층을 형성하였다. 상기 ^^1-2 증착막 위에 발광층으로서 앞서 실시예 1에서 제조한 화합물 1, 하기
Figure imgf000039_0002
화합물， 및 인광도펀트 ⑶ 을 44:44:12의 중량비로 공증착하여 400ᅀ 두께의 발광층을 형성하였다. 상기 발광층 위에 하기 £：1니 화합물을 250ᅀ의 두께로 진공 2019/147074 1»（：1/10公019/001108 The glass substrate coated with a thin film of 1,300 比 in the ratio of 0 to 3 was cleaned with ultrasonic waves in distilled water containing detergent. At this time, the detergent in the Fischer extinct language此la 0 0) was used as a product is distilled to Millipore (11 0 0 0) was used as the second filtered distilled water to a filter drive (D) of the product. After washing for 30 minutes, the plate was washed twice with distilled water and ultrasonically cleaned for 1 minute. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. The following 111-1 compound was thermally vacuum deposited on the prepared 10-electrode to a thickness of 50 탆 to form a hole injection layer. The following 117-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer to form a hole transport layer and vacuum evaporation was performed on the 1 &amp; . On the above-mentioned ^^ 1-2 vapor deposition film, the compound 1 prepared in Example 1,
Figure imgf000039_0002
Compound and a phosphorescent dopant (3) were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 nm. On the light-emitting layer, the following compound was vacuum-deposited to a thickness of 250 nm 2019/147074 1 »(: 1/10/0/0 019/001108
증착하여 전자수송증을형성하고，상기 전자수송증위에 98:2의 중량비로하기 £7ᄂ2 화합물 및 니를 공증착하여 전자주입층을 형성하였다. 상기 전자주입층 위에 1000入두께로알루미늄을증착하여 음극을형성하였다. And an electron transport layer was formed on the electron transport layer by the co-deposition of the following compounds and nigels at a weight ratio of 98: 2. Aluminum was deposited on the electron injection layer to a thickness of 1000 to form a cathode.
Figure imgf000040_0001
상기의 과정에서 유기물의 증착속도는 0.4〜 0.7入八^를유지하였고， 알루미늄은 2 人八 의 증착속도를유지하였으며， 증착시 진공도는 1 X 10 -7 ~ 5 X 10-8 10^를유지하였다. 실험예 1-1내지 1-36 2019/147074 1»(：1^1{2019/001108
Figure imgf000040_0001
Was the deposition rate of the organic material in the above process was maintained at 0.4~ 0.7入八^, aluminum is deposited at a rate of 2人八, During the deposition, a vacuum 1 X 10 - 7 ~ 5 X 10 -8 to 10 ^ Respectively. Experimental Examples 1-1 to 1-36 2019/147074 1 »(: 1 ^ {2019/001108
상기 실험예 1-1에서 실시예 1의 화합물 1 대신 하기 표 1에 기재된 화합물을사용하는것을제외하고는，상기 실험예 1-1과동일한방법으로유기 발광소자를제조하였다. 비교실험예 1-1및 1-2 An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that the compound described in Table 1 was used instead of the compound 1 of Example 1 in Experimental Example 1-1. Comparative Experimental Examples 1-1 and 1-2
상기 실험예 1에서 실시예 1의 화합물 1 대신 하기 표 1에 기재된 화합물을사용하는것을제외하고는，상기 실험예 1_1과동일한방법으로유기 발광소자를 제조하였다. 한편， 하기 표 1의 CE1 및
Figure imgf000041_0001
화합물은 하기와 같다. An organic light emitting device was prepared in the same manner as in Experimental Example 1-1 except that the compound described in the following Table 1 was used instead of the Compound 1 of Example 1 in Experimental Example 1. On the other hand, CE1 and
Figure imgf000041_0001
The compounds are as follows.
Figure imgf000041_0002
상기 실험예 및 비교실험예에서 유기 발광 소자를 10 八: 1112의 전류 밀도에서 구동 전압과 발광 효율을 측정하였고， 50 —/（계2의 전류 밀도에서 초기 휘도 대비 95%가 되는 시간（1그95）을측정하였다. 그 결과를 하기 표 1에 나타내었다.
Figure imgf000041_0002
Experimental Example and Comparative Test Example An organic light emitting device 10八in: We measured the driving voltage and luminous efficiency at a current density of 111 2, and 50 - / (Re 2 time at which the 95% compared to the initial luminance at a current density of (1 95 ) was measured. The results are shown in Table 1 below.
【표 11 [Table 11
Figure imgf000041_0003
2019/147074 1»（：1/10公019/001108
Figure imgf000041_0003
2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000042_0001
Figure imgf000042_0001
Figure imgf000043_0001
상기 표 1에서 나타난바와같이， 본발명의 화합물을발광층물질로 사용할 경우， 비교실험예에 비하여 효율 및 수명이 우수한 특성을 나타내는 것을확인할수있었다. 실험예 2-1
Figure imgf000043_0001
As shown in Table 1, when the compound of the present invention was used as a light emitting layer material, it was confirmed that the compound exhibited excellent efficiency and lifetime in comparison with the comparative example. Experimental Example 2-1
IT0( indium t in oxide)가 1,000 A 두께로 박막 코팅된 유리 기판 (corning 7059 glass)을, 분산제를 녹인 증류수에 넣고초음파로 세척하였다. 세제는 Fi scher Co.의 제품을 사용하였으며, 증류수는 Mi l l ipore Co. 제품의 필터 (Fi l ter)로 2차 걸러진 증류수를 사용하였다. IT0를 30 분간 세척한후， 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜， 아세톤， 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. 이렇게 준비된 IT0 투명 전극 위에 하기 HI-1 화합물을 500 A의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 HT-1 화합물을 400 A의 두께로 진공 증착하여 정공수송층을 형성하고, 상기 정공수송층 위에 호스트 H1과 도판트 D1 화합물을 97.5: 2.5의 중량비로 300A의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층 위에 하기 화합물 ET-A를 50 A의 두께로 진공 증착하여 전자수송증을 형성하였다. 상기 전자수송층 위에 실시예 1에서 제조한 화합물 1과 LiQ(Li thium Quinol ate)를 1: 1의 중량비로 진공 증착하여 350 A의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12 A 두께로 2019/147074 1»（：1^1{2019/001108 A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was washed with ultrasonic waves in distilled water containing dispersant. The detergent was manufactured by Fi Scher Co., and the distilled water used was Mi ll ipore Co. Distilled water, which was secondly filtered with a filter (Fi l ter) 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. The following HI-1 compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer. The following HT-1 compound was vacuum-deposited on the hole injection layer to a thickness of 400 A to form a hole transport layer. On the hole transport layer, a host H1 and a dopant D1 compound were vacuum-deposited to a thickness of 300 A at a weight ratio of 97.5: Thereby forming a light emitting layer. The following compound ET-A was vacuum-deposited on the light emitting layer to a thickness of 50 A to form electron transporting gas. Compound 1 prepared in Example 1 and LiQ (Li thium Quinolate) were vacuum deposited on the electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 A. On the electron injecting and transporting layer, 2019/147074 1 »(: 1 ^ {2019/001108
리튬플로라이드（니 와 2,000入 두께로 알루미늄을 증착하여 음극을 형성하였다. Lithium fluoride (aluminum) was deposited with nickel to a thickness of 2,000 to form a cathode.
Figure imgf000044_0001
Figure imgf000044_0001
상기의 과정에서 유기물의 증착속도는 0.4 0.7入/3 를유지하였고， 음극의 리튬플로라이드는 크入八 , 알루미늄은 요ᅀ八%의 증착 속도를 유지하였으며， 증착시 진공도는 2X10^ - 5X10 ® 100를유지하여， 유기 발광 소자를제작하였다. 실험예 2-2내지 2-36 The deposition rate of the organic material in the above process, 0.4 0.7 was maintained入/ 3, the lithium fluoride of the cathode is greater入八, aluminum I were deposited at speeds of ᅀ 八%, During the deposition, a vacuum 2X10 ^ - 5X10 ® by keeping the 100 was produced in the organic light emitting device. Experimental Examples 2-2 to 2-36
상기 실험예 2-1에서 실시예 1의 화합물 1 대신 하기 표 2에 기재된 화합물을사용하는것을제외하고는，상기 실험예 2-1과동일한방법으로유기 발광소자를제조하였다. 비교실험예 2-1및 2-2  An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the compound described in the following Table 2 was used instead of the compound 1 of Example 1 in Experimental Example 2-1. Comparative Experimental Examples 2-1 and 2-2
상기 실험예 2-1에서 실시예 1의 화합물 1 대신 하기 표 2에 기재된 화합물을사용하는것을제외하고는，상기 실험예 2-1과동일한방법으로유기 발광소자를제조하였다.하기
Figure imgf000044_0002
화합물은하기와같다. 2019/147074 1»(：1/10公019/001108
Figure imgf000045_0001
An organic light emitting device was prepared in the same manner as in Experimental Example 2-1 except that the compound described in the following Table 2 was used instead of the Compound 1 of Example 1 in Experimental Example 2-1.
Figure imgf000044_0002
The compounds are as follows. 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000045_0001
0º6  0º6
상기 실험예 및 비교실험예에서 유기 발광 소자를 10—/（에2의 전류 밀도에서 구동 전압과 발광 효율을 측정하였고， 50 八: 의 전류 밀도에서 초기 휘도 대비 95%가되는 시간 0 95）을측정하였다. 그 결과를 하기 표 1에 나타내었다. Experimental Example and Comparative Test Example An organic light emitting device 10 in the - / (were measured drive voltage and luminous efficiency at a current density of 2, 50八: hour 0 to 95 where 95% of the initial luminance at a current density of) the Respectively. The results are shown in Table 1 below.
【표 2】 [Table 2]
Figure imgf000045_0002
2019/147074 1»（：1/10公019/001108
Figure imgf000045_0002
2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000046_0001
2019/147074 1»（：1^1{2019/001108
Figure imgf000046_0001
2019/147074 1 »(: 1 ^ {2019/001108
Figure imgf000047_0001
상기 표 2에 나타난 바와 같이, 본 발명의 화합물을 전자수송층 물질로 사용할 경우， 비교실험예에 비하여 효율 및 수명이 우수한 특성을 나타내는것을확인할수있었다.
Figure imgf000047_0001
As shown in Table 2, when the compound of the present invention was used as an electron transport layer material, it was confirmed that the compound exhibited excellent efficiency and lifetime in comparison with Comparative Experimental Example.
【부호의 설명】 DESCRIPTION OF REFERENCE NUMERALS
기판 2： 양극  Substrate 2: anode
3 발광층 4： 음극  3 Emission layer 4: cathode
5 정공주입층 6： 정공수송층  5 Hole injection layer 6: Hole transport layer
7 전자저지층 8： 발광층  7 electron blocking layer 8: light emitting layer
9 전자수송층 10： 전자주입층  9 Electron transport layer 10: Electron injection layer
11: 전자주입 및수송층  11: electron injection and transport layer

Claims

2019/147074 1»(：1/10公019/001108 【청구범위】 【청구항 1] 하기 화학식 1로표시되는화합물: Claims 1. A compound represented by the following formula (1): wherein R 1, R 2, R 3, R 4, R 5,
[화학식 1]  [Chemical Formula 1]
Figure imgf000048_0001
Figure imgf000048_0001
묘’ 는 각각 독립적으로 치환 또는 비치환된 01-60 알킬; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 06-60 아릴 ; 치환 또는 비치환된 06-60 아릴옥시 ; 또는 치환 또는 비치환된 0, 및 중 1개 이상을포함하는 02-60헤테로아릴이고, &Lt; / RTI &gt; are each independently substituted or unsubstituted 0-60 alkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 6-60 aryl ; Substituted or unsubstituted 0 6-60 aryloxy ; Or substituted or unsubstituted 0, and 0 2-60 heteroaryl containing at least one of the foregoing,
¾ 내지 ¾은 각각 독립적으로 할로겐; 히드록시기; 시아노, 니트릴; 니트로 ; 아미노 ; 치환 또는 비치환된 0!-60 알킬 ; 치환 또는 비치환된 01-60 할로알킬 ; 치환 또는 비치환된 01-60 티오알킬 ; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 01-60 할로알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 0!-60 알케닐 ; 치환 또는 비치환된 06-60 아릴; 치환 또는 비치환된 06-60 아릴옥시; 또는 치환또는 비치환된 0 凡 및 중 1개 이상을포함하는 02-60헤테로아릴이고， Each of ¾ to ¾ is independently halogen; A hydroxy group; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted 0-60 alkyl; Substituted or unsubstituted 0 1-60 haloalkyl; Substituted or unsubstituted 0 1-60 thioalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0-60 haloalkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0-60 alkenyl; Substituted or unsubstituted 0 6-60 aryl; Substituted or unsubstituted 0 6-60 aryloxy; Or substituted or unsubstituted 0-60 heteroaryl containing 0 or more of one or more,
3 , 6및융는각각독립적으로 0내지 4이고， 3, 6 and Y are each independently 0 to 4,
13， （1및 군는각각독립적으로 0내자 3이고， 1 3 , (1 and the group are each 0 independently of 0 and 3,
는 0내지 5이다.  Lt; / RTI &gt;
【청구항 2】 [Claim 2]
제 1항에 있어서， 2019/147074 1»（：1^1{2019/001108 The method according to claim 1, 2019/147074 1 »(: 1 ^ {2019/001108
요’ 는메틸인， 화합물. Is methyl.
【청구항 3] [3]
제 1항에 있어서，  The method according to claim 1,
b, （：, <1, 근및 군는 0인， 화합물.  b, (:, < 1, the moiety and the group are 0).
【청구항 4] [4]
제 1항에 있어서,  The method according to claim 1,
¾내지 ¾중적어도하나는시아노인， 화합물.  One to three or four of the radicals are cyano.
【청구항 5] [Claim 5]
제 1항에 있어서，  The method according to claim 1,
상기 화학식 1은 하기로 구성되는 군으로부터 선택되는 어느 하나로 표시되는, 화합물:  Wherein the compound represented by Formula 1 is represented by any one selected from the group consisting of:
Figure imgf000049_0001
Figure imgf000049_0001
2019/147074 1»（：1^1{2019/001108 2019/147074 1 »(: 1 ^ {2019/001108
Figure imgf000050_0001
에 대한설명은제 1항에서 정의한바와같다.
Figure imgf000050_0001
Is as defined in claim 1.
【청구항 6] [Claim 6]
제 1항에 있어서，  The method according to claim 1,
상기 화학식 1로 표시되는 화합물은 하기 화합물로 구성되는 군으로부터 선택되는어느하나인, 화합물: Wherein the compound represented by Formula 1 is any one selected from the group consisting of the following compounds:
Figure imgf000051_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000052_0001
2019/147074 1»（：1/10公019/001108 2019/147074 1 »(: 1/10/0/0 019/001108
Figure imgf000053_0001
Figure imgf000053_0001
【청구항 7】 7.
제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 2019/147074 1»（：1^1{2019/001108 A first electrode; A second electrode facing the first electrode; And the first 2019/147074 1 »(: 1 ^ {2019/001108
전극과 상기 제 2 전극 사이에 구비된 1증 이상의 유기물증을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 제 1항 내지 제 6항 중 어느 하나의 항에 따른화합물을포함하는, 유기 발광소자. Wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 6, and at least one of the organic layers comprises a compound according to any one of claims 1 to 6. Light emitting element.
5 【청구항 8] 5 [Claim 8]
제 7항에 있어서，  8. The method of claim 7,
상기 화합물을포함하는유기물층은전자주입층; 전자수송층; 전자주입 및수송층; 또는발광층인， 유기 발광소자.  The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Electron injection and transport layer; Or a light emitting layer.
10 【청구항 9] 10 [Claim 9]
제 8항에 있어서 ,  9. The method of claim 8,
상기 발광층은 2종 이상의 호스트를포함하고, 상기 호스트중 하나가 상기 화합물인, 유기 발광소자.  Wherein the light emitting layer comprises two or more kinds of hosts, and one of the hosts is the compound.
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KR20150070860A (en) * 2013-12-17 2015-06-25 삼성전자주식회사 Condensed cyclic compound and organic light emitting device including the same
KR20180055688A (en) * 2016-11-17 2018-05-25 주식회사 엘지화학 Compound and organic light emitting device comprising the same

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