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WO2019209031A1 - Novel heterocyclic compound and organic light emitting device using same - Google Patents

Novel heterocyclic compound and organic light emitting device using same Download PDF

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Publication number
WO2019209031A1
WO2019209031A1 PCT/KR2019/004969 KR2019004969W WO2019209031A1 WO 2019209031 A1 WO2019209031 A1 WO 2019209031A1 KR 2019004969 W KR2019004969 W KR 2019004969W WO 2019209031 A1 WO2019209031 A1 WO 2019209031A1
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WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
group
light emitting
layer
Prior art date
Application number
PCT/KR2019/004969
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French (fr)
Korean (ko)
Inventor
정민우
이동훈
장분재
이정하
한수진
박슬찬
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020190047557A external-priority patent/KR102206482B1/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP19792248.7A priority Critical patent/EP3730488B1/en
Priority to US16/963,189 priority patent/US11925113B2/en
Priority to CN201980009436.8A priority patent/CN111655683B/en
Publication of WO2019209031A1 publication Critical patent/WO2019209031A1/en

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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multilayer structure composed of different materials, and for example, may be formed of 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 [Contents of the Invention]
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same. [Measures of problem]
  • the present invention provides a compound represented by the following formula (1).
  • Yo is substituted 0 6 -60 aryl; Or substituted or unsubstituted 0, and 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0! -60 haloalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 1-60 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • Haloalkoxy Substituted or unsubstituted 0 3 -60 cycloalkyl; Substituted or unsubstituted 02-60 alkenyl; Substituted or unsubstituted 0 6 -60 aryl; Substituted or unsubstituted 0 6 -60 aryloxy; Or 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted non 0 and
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. to provide.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9. And an example of an organic light emitting element composed of a cathode (4).
  • the present invention provides a compound represented by Chemical Formula 1.
  • the term ⁇ substituted or unsubstituted '' is deuterium; halogen; cyano; nitro; hydroxy; carbonyl; ester; imide; amino; phosphine oxide; alkoxy; aryloxy; Alkylthioxy group; arylthioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkyl An amine group; heteroarylamine group; arylamine group; arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of 0 and heteroaryl containing one or more of the atoms, or It means a substituted or unsubstituted linked two or more substituent
  • the ester group may be substituted with oxygen of the ester group having a straight chain, branched or cyclic alkyl group having 6 to 25 carbon atoms or aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto. 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, butylbutyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group.
  • the boron group is specifically trimethyl boron group, triethyl boron group, butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. Another one 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, -butyl, isobutyl, ratchet butyl, 1-Methyl-butyl, 1-ethyl-butyl, pentyl, 11_pentyl, isopentyl, neopentyl, ratchetpentyl, nuclear chamber, 11-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4 -methyl-2- Pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, 11-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuctylmethyl, octyl,
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, it is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms.
  • the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • 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 an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, or the like, but is not limited thereto.
  • heteroaryl is a heteroaryl containing one or more of 0, ⁇ , and £ as a heterologous element, carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group, Pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl, isoquinoline, indole, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group,
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heteroaryl.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description about the aryl group described above may be applied except that the arylten is a divalent group. example 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the description of the aforementioned heteroaryl may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding.
  • the show may be any one selected from the group consisting of:
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently, 3 , at least two of 3 ⁇ 4 to 3 ⁇ 4 are
  • ⁇ 2 and ⁇ are each independently 0, 3 or ⁇ ’
  • 2 to 5 each independently represent a substituted or unsubstituted 0 6-60 aryl; Or 0! -60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, ⁇ and £,
  • Seedlings are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the show may be any one selected from the group consisting of:
  • Hydrogen Deuterium; Cyano; Or substituted or unsubstituted 0 1-10 alkyl.
  • 3 ⁇ 4 to 3 ⁇ 4 may be hydrogen.
  • the compound may be selected from the group consisting of the following compounds:
  • the compound represented by the formula (1) can be prepared by the same method as in the following scheme 1, for example:
  • the description is as defined in the formula (1).
  • the reaction is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And between the first electrode and the second electrode. 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • An organic light emitting device including at least one organic material layer, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1, and provides an organic light emitting device.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic 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 light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 may be used as a host material in the emission layer.
  • the light emitting layer may include two or more types of hosts.
  • one of the hosts may be a compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer. 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting diode according to the present invention may be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time,
  • a conductive metal oxide or an alloy thereof is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
  • the organic light emitting device may be manufactured by sequentially depositing materials.
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide ((1), indium zinc oxide (10)); Combinations of metals and oxides, such as 3 ⁇ 40: hour or 3 ⁇ 2 : ⁇ ; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene], polypyrrole and polyaniline, and the like, but are not limited thereto. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 Ml, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • HOMOC of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic matter.
  • the hole injecting materials include metal porphyrin, oligothiophene, arylamine-based organic matter, nucleonitrile-nuclear azatriphenylene-based organic matter, 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring the holes to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (C3 ⁇ 4); Carbazole series compounds; Dimerized styryl (11161 ⁇ root 1) compounds; 6 o'clock (1; 10 -hydroxybenzo quinoline metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (1) phenylene vinylene) 1) series polymer; Spiro vs. Compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative may be a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • styrylamine compound examples include a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, an aryl group, a silyl group, A substituent selected from the group consisting of an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like is not limited thereto.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • an electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include a complex of 8-hydroxyquinoline; Complexes containing show 13 ⁇ 4; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum or silver layer in each case.
  • the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • said metal complex compound 8-hydroxyquinolinato lithium, bis (8- 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
  • a glass substrate coated with a thin film of I0 (indium tin oxide) having a thickness of 1,300 A was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • Fischer Co. product was used as the detergent
  • distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as the distilled water.
  • the ultrasonic cleaning was repeated 10 times with laminar flow twice.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone and methanol 2019/209031 1 »(: 1 ⁇ 1 ⁇ 2019/004969
  • the substrate was washed with oxygen plasma for 5 minutes and then transported to a vacuum evaporator.
  • a hole injection layer was formed by thermal vacuum deposition of the following ⁇ 1 compound to a thickness of 50 particles on the 110 transparent electrode prepared as described above.
  • the following -1 compound was vacuum-deposited to a thickness of 250 particles on the hole injection layer to form a hole transport layer, and then on the hole transport certificate.
  • the compound was vacuum deposited to a thickness of 50 shows to form an electron blocking layer.
  • Compound 1, the following compound-1, and phosphorescent dopant ⁇ 01) -1 prepared in Example 1 as a light emitting layer on the electron blocking layer were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 particles. It was.
  • the following -1 compound was vacuum deposited to a thickness of 250 ⁇ on the light emitting layer to form an electron transport layer, and the following £ 1-2 compound and the needle were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to inject 100 nm thick electrons.
  • a layer was formed.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 particles to form a cathode.
  • An organic light-emitting device was manufactured in the same manner as in Experiment 1, except that the compound shown in Table 1 was used instead of the compound 1 prepared in Example 1.
  • CE1 CE12 and CE3 compounds of the following Table 1 are as follows.
  • the organic light emitting diodes of the Experimental Example and the Comparative Experimental Example were measured voltage and efficiency at a current density of 10— / 011 2 , and lifespan was measured at a current density of 50 ⁇ : #, and the results are shown in Table 1 below. At this time, 1 95 means the time to be 95% of the initial luminance.
  • Substrate 2 Anode

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Abstract

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

Description

2019/209031 1»（：1^1{2019/004969  2019/209031 1 »（： 1 ^ 1 {2019/004969
【발명의 명칭】 [Name of invention]
신규한 헤테로 고리 화합물 및 이를 이용한유기발광소자 【기술분야】  Novel heterocyclic compound and organic light emitting device using the same
관련 출원 (들)과의 상호 인용 Cross Citation with Related Application (s)
본 출원은 2018년 4월 24일자 한국 특허 출원 제 10-2018-0047306호， 및 2019년 4월 23일자 한국 특허 출원 제 10-2019-0047557호에 기초한우선권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다.  This application claims the benefit of priority based on Korean Patent Application No. 10-2018-0047306 of April 24, 2018, and Korean Patent Application No. 10-2019-0047557 of April 23, 2019, and the Korean Patent Application All content disclosed in these references is included as part of this specification.
본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.  The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
【발명의 배경이 되는 기술】 [Technique to become background of invention]
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광소자는 넓은 시야각， 우수한콘트라스트, 빠른 응답 시간을 가지며， 휘도， 구동 전압 및 응답속도특성이 우수하여 많은 연구가진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며， 예컨대 정공 주입층, 정공 수송층, 발광층， 전자수송층, 전자 주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물 층에 주입되게 되고， 주입된 정공과 전자가 만났을 때 엑시톤 (6X0^011)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다. 2019/209031 1»（：1^1{2019/004969 In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted. The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic layer, and excitons (6X0 ^ 011) are formed when the injected holes and the electrons meet each other. When this exciton falls back to the ground, it glows. There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices. 2019/209031 1 »（： 1 ^ 1 {2019/004969
【선행기술문헌】 Prior Art Documents
【특허문헌】  [Patent literature]
（특허문헌 0001） 한국특허 공개번호 제 10-2000-0051826호 【발명의 내용】  (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 [Contents of the Invention]
【해결하고자 하는 과제】  Problem to be solved
본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. 【과제의 해결 수단】  The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same. [Measures of problem]
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.  The present invention provides a compound represented by the following formula (1).
［화학식 1］  [Formula 1]
Figure imgf000003_0001
Figure imgf000003_0001
상기 화학식 1에서， In Chemical Formula 1,
은 0또는 이고，  Is 0 or
요 은 치환된 06-60 아릴; 또는 치환 또는 비치환된 0 , 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상을 포함하는 01-60 헤테로아릴이고, Yo is substituted 0 6 -60 aryl; Or substituted or unsubstituted 0, and 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of
［은 단일 결합 ; 치환 또는 비치환된 06-60 아릴텐 ; 또는 치환 또는 비치환된 0 , 比 ^ 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상을 포함하는 01-60 헤테로아릴텐이고， [Is a single bond; Substituted or unsubstituted 0 6-60 arylten ; Or 0 1 -60 heteroarylten containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, 比 ^ and
¾ 내지 ¾는 각각 독립적으로， 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 01-60 알킬; 치환 또는 비치환된 0!-60 할로알킬 ; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 01-60 2019/209031 1»（：1^1{2019/004969 ¾ to ¾ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0! -60 haloalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 1-60 2019/209031 1 »（： 1 ^ 1 {2019/004969
할로알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 02-60 알케닐 ; 치환 또는 비치환된 06-60 아릴 ; 치환 또는 비치환된 06-60 아릴옥시 ; 또는 치환 또는 비치환된 比 0 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상포함하는 01-60 헤테로아릴이고， Haloalkoxy; Substituted or unsubstituted 0 3 -60 cycloalkyl; Substituted or unsubstituted 02-60 alkenyl; Substituted or unsubstituted 0 6 -60 aryl; Substituted or unsubstituted 0 6 -60 aryloxy; Or 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted non 0 and
111 내지 113은 각각독립적으로, 1 내지 5의 정수이다. 또한， 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물 층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을포함하는， 유기 발광소자를 제공한다.  111 to 113 are each independently an integer of 1 to 5. In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. to provide.
【발명의 효과】 【Effects of the Invention】
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며， 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는수명 특성을 향상시킬 수 있다.  The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
【도면의 간단한설명】 【Brief Description of Drawings】
도 1은 기판 ( 1) , 양극 (2) , 발광층 (3) , 음극 (4)으로 이루어진 유기 발광소자의 예를 도시한 것이다.  FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는 기판 ( 1) , 양극 (2) , 정공주입층 (5) , 정공수송층 (6) , 전자저지층 (7) , 발광층 (3) , 전자수송층 (8) , 전자주입층 (9) 및 음극 (4)로 이루어진 유기 발광소자의 예를 도시한 것이다.  2 shows 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 3, an electron transport layer 8, an electron injection layer 9. And an example of an organic light emitting element composed of a cathode (4).
【발명을실시하기 위한구체적인 내용】 [Specific contents for carrying out invention]
이하， 본 발명의 이해를 돕기 위하여 보다상세히 설명한다. 본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다.  Hereinafter, the present invention will be described in more detail to help understand the present invention. The present invention provides a compound represented by Chemical Formula 1.
본 명세서에서, +는 다른 치환기에 연결되는 결합을 의미한다. 2019/209031 1»（：1/10公019/004969 In the present specification, + means a bond connected to another substituent. 2019/209031 1 »（： 1/10 公 019/004969
본 명세서에서 ''치환또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 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 0 및 원자 중 1개 이상을 포함하는 헤테로아릴로 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’'가 바이페닐기인 경우, 바이페닐이기는 1개의 페닐기로 치환된 아릴기이거나， 또는 2개의 페닐기가 연결된 치환기로 해석될 수 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다. As used herein, the term `` substituted or unsubstituted '' is deuterium; halogen; cyano; nitro; hydroxy; carbonyl; ester; imide; amino; phosphine oxide; alkoxy; aryloxy; Alkylthioxy group; arylthioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkyl An amine group; heteroarylamine group; arylamine group; arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of 0 and heteroaryl containing one or more of the atoms, or It means a substituted or unsubstituted linked two or more substituents, for example, when the "substituent linked by two or more substituents" is a biphenyl group, the biphenyl group is one phenyl group It may be interpreted as a substituted aryl group or a substituent to which two phenyl groups are linked. Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
Figure imgf000005_0001
본 명세서에 있어서， 에스테르기는 에스테르기의 산소가 탄소수 내지 25의 직쇄， 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다. 2019/209031 1»（：1^1{2019/004969
Figure imgf000006_0001
본 명세서에 있어서， 이미드기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.
Figure imgf000005_0001
In the present specification, the ester group may be substituted with oxygen of the ester group having a straight chain, branched or cyclic alkyl group having 6 to 25 carbon atoms or aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto. 2019/209031 1 »（： 1 ^ 1 {2019/004969
Figure imgf000006_0001
In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
Figure imgf000006_0002
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기， 트리에틸실릴기， 卜부틸디메틸실릴기， 비닐디메틸실릴기， 프로필디메틸실릴기， 트리페닐실릴기, 디페닐실릴기， 페닐실릴기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 붕소기는 구체적으로 트리메틸붕소기 , 트리에틸붕소기, 부틸디메틸붕소기, 트리페닐붕소기， 페닐붕소기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 할로겐기의 예로는 불소 , 염소， 브롬 또는 요오드가 있다. 본 명세서에 있어서， 상기 알킬기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 2019/209031 1»（：1^1{2019/004969
Figure imgf000006_0002
In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, butylbutyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited to this. In the present specification, the boron group is specifically trimethyl boron group, triethyl boron group, butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto. 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 chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. Another one 2019/209031 1 »（： 1 ^ 1 {2019/004969
실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸， 에틸, 프로필， 11-프로필， 이소프로필, 부틸, -부틸, 이소부틸, 라卜부틸，
Figure imgf000007_0001
1 -메틸-부틸， 1 -에틸-부틸, 펜틸， 11_펜틸， 이소펜틸， 네오펜틸， 라卜펜틸, 핵실， 11-핵실， 1 -메틸펜틸， 2 -메틸펜틸, 4 -메틸- 2 -펜틸, 3，3 -디메틸부틸， 2 -에틸부틸, 헵틸， 11-헵틸， 1 -메틸핵실， 사이클로펜틸메틸，사이클로핵틸메틸， 옥틸， !：_옥틸， 16 _옥틸， 1 -메틸헵틸，According to the exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, 11-propyl, isopropyl, butyl, -butyl, isobutyl, ratchet butyl,
Figure imgf000007_0001
1-Methyl-butyl, 1-ethyl-butyl, pentyl, 11_pentyl, isopentyl, neopentyl, ratchetpentyl, nuclear chamber, 11-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4 -methyl-2- Pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, 11-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuctylmethyl, octyl,! ： _ Octyl, 16_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 2 내지 6이다. 구체적인 예로는 비닐， 1 -프로페닐, 이소프로페닐， 1 -부테닐, 2 -부테닐， 3 -부테닐， 1 -펜테닐，2-ethylnuclear chamber, 2-propylpentyl, 11-nonyl, 2, 2-dimethylheptyl, 1-ethyl-propyl, 1, 1-dimethyl-propyl, isonuclear chamber, 2-methylpentyl, 4-methylnuclear chamber, 5- Methyl nucleus, and the like, but are not limited to these. In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, it is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl,
2 -펜테닐， 3 -펜테닐， 3 -메틸- 1 -부테닐, 1，3 -부타디에닐， 알릴， 1 -페닐비닐- 1- 일， 2 -페닐비닐- 1 -일, 2 , 2 -디페닐비닐- 1 -일， 2 -페닐- 2-（나프틸- 1 -일）비닐- 1 -일， 2 , 2 -비스（디페닐- 1 -일）비닐- 1 -일， 스틸베닐기， 스티레닐기 등이 있으나 이들에 한정되지 않는다. 본 명세서에 있어서， 사이클로알킬기는 특별히 한정되지 않으나， 탄소수 3 내지 60인 것이 바람직하며， 일 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필， 사이클로부틸， 사이클로펜틸， 3 -메틸사이클로펜틸， 2 , 3 -디메틸사이클로펜틸 , 사이클로핵실 , 3 -메틸사이클로핵실 , 4 -메틸사이클로핵실， 2 , 3- 디메틸사이클로핵실， 3 ,4 , 5 -트리메틸사이클로핵실 , 4마6 _부틸사이클로핵실 , 2019/209031 1»（：1^1{2019/004969 2 -pentenyl, 3 -pentenyl, 3 -methyl- 1 -butenyl, 1,3-butadienyl, allyl, 1 -phenylvinyl 1-yl, 2 -phenylvinyl-l-yl, 2, 2 -Diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbe And a nil group, a styrenyl group and the like, but is not limited thereto. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclonuclear chamber, 3-methylcyclonuclear chamber, 4-methylcyclonuclear chamber, 2, 3-dimethylcyclonuclear chamber, 3, 4, 5-trimethylcyclonuclear chamber, 4 hexa 6-butylcyclonuclear chamber, 2019/209031 1 »（： 1 ^ 1 {2019/004969
사이클로헵틸， 사이클로옥틸 등이 있으나, 이에 한정되지 않는다. 본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며， 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기 , 바이페닐기 , 터페닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기， 페난트릴기， 파이레닐기， 페릴레닐기， 크라이세닐기， 등이 될 수 있으나, 이에 한정되는 것은 아니다. 본 명세서에 있어서， 헤테로아릴은 이종 원소로 0 , 比 및 £ 중 1개 이상을 포함하는 헤테로아릴로서， 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로아릴의 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， 벤조카바졸기 , 벤조티오펜기 , 디벤조티오펜기 , 벤조퓨라닐기 ,
Figure imgf000008_0001
Cycloheptyl, cyclooctyl, and the like, but is not limited thereto. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, or the like, but is not limited thereto. In the present specification, heteroaryl is a heteroaryl containing one or more of 0, 比, and £ as a heterologous element, carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group, Pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl, isoquinoline, indole, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group,
Figure imgf000008_0001
이소옥사졸릴기， 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다. 본 명세서에 있어서， 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서， 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴텐은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 2019/209031 1»（：1^1{2019/004969 There is an isoxoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto. 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 example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heteroaryl. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description about the aryl group described above may be applied except that the arylten is a divalent group. example 2019/209031 1 »（： 1 ^ 1 {2019/004969
명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 한편， 상기 화학식 1에서， 쇼 은 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다. In the specification, the description of the aforementioned heteroaryl may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding. On the other hand, in Formula 1, the show may be any one selected from the group consisting of:
Figure imgf000009_0001
Figure imgf000009_0001
상기에서,  In the above,
¾ 내지 ¾은 각각 독립적으로,
Figure imgf000009_0002
3이되， ¾ 내지 ¾중 2개 이상은 이고， ¾ to ¾ are each independently,
Figure imgf000009_0002
3 , at least two of ¾ to ¾ are
^2 및 九은 각각 독립적으로， 0 , 3 또는 ■’ 이고， ^ 2 and 九 are each independently 0, 3 or ■ ’
2 내지 5는 각각 독립적으로 , 치환 또는 비치환된 06-60 아릴 ; 또는 치환 또는 비치환된 0， ^ 및 £로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상을 포함하는 0!-60 헤테로아릴이고， 2 to 5 each independently represent a substituted or unsubstituted 0 6-60 aryl; Or 0! -60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, ^ and £,
묘’ 는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 2019/209031 1»（：1^1{2019/004969 Seedlings are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; 2019/209031 1 »（： 1 ^ 1 {2019/004969
아미노 ; 치환 또는 비치환된 01-60 알킬 ; 치환 또는 비치환된 01-60 할로알킬 ; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 01-60 할로알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 02-60 알케닐 ; 치환 또는 비치환된 06-60 아릴 ; 치환 또는 비치환된 06-60 아릴옥시 ; 또는 치환 또는 비치환된 比 0 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 01-60 헤테로아릴이고， Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0 1-60 haloalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 01-60 haloalkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 2-60 alkenyl; Substituted or unsubstituted 0 6-60 aryl; Substituted or unsubstituted 0 6-60 aryloxy; Or 0 1-60 heteroaryl containing one or more hetero atoms selected from the group consisting of substituted or unsubstituted non 0 and
:14 내지 1111은 각각 독립적으로, 1 내지 5의 정수일 수 있다. 바람직하게는， 쇼 은 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다.  14 to 1111 may be each independently an integer of 1 to 5. Preferably, the show may be any one selected from the group consisting of:
Figure imgf000010_0001
2019/209031 1»（：1^1{2019/004969
Figure imgf000011_0001
상기에서，
Figure imgf000010_0001
2019/209031 1 »（： 1 ^ 1 {2019/004969
Figure imgf000011_0001
Above
2 및 5 에 대한설명은 앞서 정의한 바와 같다. 바람직하게는, 상기 화학식 1에서， 느은 단일 결합， 또는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다. The description of 2 and 5 is as defined above. Preferably, in Chemical Formula 1, a single bond, or any one selected from the group consisting of:
Figure imgf000011_0002
바람직하게는, 상기 화학식 1에서， ¾ 내지
Figure imgf000011_0003
각각 독립적으로， 2019/209031 1»（：1^1{2019/004969
Figure imgf000011_0002
Preferably, in Chemical Formula 1, ¾ to
Figure imgf000011_0003
Each independently, 2019/209031 1 »（： 1 ^ 1 {2019/004969
수소 ; 중수소 ; 시아노 ; 또는 치환또는 비치환된 01-10 알킬일 수 있다 . 예를 들어， ¾ 내지 ¾은 수소일 수 있다. 예를 들어， 상기 화합물은， 하기 화합물로 구성되는 군으로부터 선택될 수 있다: Hydrogen ; Deuterium; Cyano; Or substituted or unsubstituted 0 1-10 alkyl. For example, ¾ to ¾ may be hydrogen. For example, the compound may be selected from the group consisting of the following compounds:
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000018_0001
Figure imgf000018_0001
 2019/209031 1»（：1^1{2019/004969  2019/209031 1 »（： 1 ^ 1 {2019/004969
한편, 상기 화학식 1로 표시되는 화합물은 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다: On the other hand, the compound represented by the formula (1) can be prepared by the same method as in the following scheme 1, for example:
[반응식 1]  Scheme 1
Figure imgf000019_0001
Figure imgf000019_0001
설명은 상기 화학식 1에서 정의한 바와 같다. 상기 반응은 스즈키 커플링 반응으로서， 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며， 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 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 전극과 상기 제 2 전극 사이에 구비된 2019/209031 1»（：1^1{2019/004969 The description is as defined in the formula (1). The reaction is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The manufacturing method may be more specific in the production examples to be described later. In addition, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And between the first electrode and the second electrode. 2019/209031 1 »（： 1 ^ 1 {2019/004969
1층 이상의 유기물 층을포함하는 유기 발광소자로서， 상기 유기물 층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. 본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나， 2층 이상의 유기물 층이 적층된 다층 구조로 이루어질 수 있다. 예컨대， 본 발명의 유기 발광소자는유기물 층으로서 정공주입층， 정공수송층, 전자저지층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을포함할수 있다. 구체적으로, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은상기 화학식 1로 표시되는 화합물을포함할수 있다. 이때， 상기 화학식 1로 표시되는 화합물은 발광층에서 호스트 물질로 사용될 수 있다. 또한， 상기 발광층은 2종 이상의 호스트를 포함할 수 있다. 또한, 상기 호스트 중 하나가상기 화학식 1로 표시되는 화합물일 수 있다. 또한， 본 발명에 따른유기 발광소자는, 기판상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대 , 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다. 도 1은 기판 ( 1)， 양극 (2) , 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은상기 발광층에 포함될 수 있다. 2019/209031 1»（：1^1{2019/004969 An organic light emitting device including at least one organic material layer, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. 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 injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. Specifically, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 may be used as a host material in the emission layer. In addition, the light emitting layer may include two or more types of hosts. In addition, one of the hosts may be a compound represented by Chemical Formula 1. In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material 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. 1 and 2. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. 2019/209031 1 »（： 1 ^ 1 {2019/004969
도 2는 기판 ( 1) , 양극 (2) , 정공주입층 (5)， 정공수송층 (6) , 전자저지층 (7) , 발광층 (3)， 전자수송층 (8)， 전자주입층 (9) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 정공 주입층， 정공 수송층， 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한， 상기 유기 발광 소자가 복수개의 유기물 층을 포함하는 경우, 상기 유기물 층은 동일한 물질 또는 다른물질로 형성될 수 있다. 예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제 1 전극， 유기물 층 및 제 2 전극을 순차적으로 적층시켜 께조할 수 있다. 이때，
Figure imgf000021_0001
2 shows 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 3, an electron transport layer 8, an electron injection layer 9. And an example of an organic light-emitting device composed of a cathode (4). In such a structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials. For example, the organic light emitting diode according to the present invention may be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time,
Figure imgf000021_0001
전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고， 그 위에 정공 주입층, 정공 수송층， 발광층 및 전자수송층을포함하는 유기물 층을 형성한후, 그 위에 음극으로 사용할수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물 층, 양극 물질을 차례로 증착시켜 유기 발광소자를 만들 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서， 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩， 잉크젯 프린팅， 스크린 프린팅， 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다. 이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물 층， 양극 2019/209031 1»（：1^1{2019/004969 A conductive metal oxide or an alloy thereof is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. Can be prepared. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. In addition, the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto. In addition to these methods, the organic material layer and the anode from the cathode material on the substrate 2019/209031 1 »（： 1 ^ 1 {2019/004969
물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다 0 2003/012890） . 다만， 제조 방법이 이에 한정되는 것은 아니다. 일례로， 상기 제 1 전극은 양극이고， 상기 제 2 전극은 음극이거나, 또는 상기 제 1 전극은 음극이고, 상기 제 2 전극은 양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나둠， 크롬, 구리 , 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물， 인듐 산화물， 인듐주석 산화물（ ⑴， 인둠아연 산화물（1 0）과 같은 금속 산화물; ¾0 :시 또는 3炯2 :況와 같은 금속과 산화물의 조합; 폴리（3- 메틸티오펜）， 폴리［3 , 4-（에틸렌- 1 , 2 -디옥시）티오펜］어묘아）， 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물 층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘， 칼슘, 나트륨， 칼륨， 티타늄， 인둠， 이트륨, 리튬， 가돌리늄， 알루미늄, 은， 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02Ml과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 정공주입층은 전극으로부터 정공을 주입하는 층으로， 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과， 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고， 발광층에서 생성된 여기자의 전자 주입층 또는 전자주입재료에의 이동을 방지하며 , 또한， 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMOChighest occupi ed molecul ar orbi tal）가 양극 물질의 일함수와 주변 유기물 증의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린（porphyr in）, 올리고티오펜， 아릴아민 계열의 유기물， 핵사니트릴핵사아자트리페닐렌 계열의 유기물 , 2019/209031 1»（：1^1{2019/004969 The organic light emitting device may be manufactured by sequentially depositing materials. 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, the second electrode is an anode. As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (⑴, indium zinc oxide (10)); Combinations of metals and oxides, such as ¾0: hour or 3 炯2 : 況; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene], polypyrrole and polyaniline, and the like, but are not limited thereto. It is preferable that the cathode material is 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; Multilayer structure materials such as LiF / Al or Li0 2 Ml, and the like, but are not limited thereto. The hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. HOMOC of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic matter. Specific examples of the hole injecting materials include metal porphyrin, oligothiophene, arylamine-based organic matter, nucleonitrile-nuclear azatriphenylene-based organic matter, 2019/209031 1 »（： 1 ^ 1 {2019/004969
퀴나크리돈（（111 13（： （10116）계열의 유기물, 페릴렌 16116） 계열의 유기물， 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. 상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로， 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물， 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나， 이들에만 한정되는 것은 아니다. 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. 구체적인 예로 8 -히드록시-퀴놀린 알루미늄 착물（시¾）; 카르바졸 계열 화합물; 이량체화 스티릴（ 11161· 근선 1） 화합물; 6시（1 ; 10 -히드록시벤조 퀴놀린_ 금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리（1）_ 페닐렌비닐렌） 1 ） 계열의 고분자; 스피로 대） 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 발광층은 호스트 재료 및 도펀트 재료를 포함할수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체， 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체， 페난트렌 화합물, 플루오란텐 화합물 등이 있고， 헤테로환 함유 화합물로는 카바졸 유도체， 디벤조퓨란 유도체， 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나， 이에 한정되지 않는다. 도펀트 재료로는 방향족 아민 유도체， 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물， 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서， 2019/209031 1»（：1^1{2019/004969 Quinacridone ((111 13 (： (10116)) series organic materials, perylene 16116) series organic materials, anthraquinone and polyaniline and polythiophene based conductive polymers, but are not limited thereto. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. A hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring the holes to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (C¾); Carbazole series compounds; Dimerized styryl (11161 · root 1) compounds; 6 o'clock (1; 10 -hydroxybenzo quinoline metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (1) phenylene vinylene) 1) series polymer; Spiro vs. Compounds; Polyfluorene, rubrene and the like, but are not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative may be a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, 2019/209031 1 »（： 1 ^ 1 {2019/004969
아릴아미노기를 갖는 피렌， 안트라센, 크리센， 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로， 아릴기, 실릴기， 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다 . 구체적으로 스티릴아민 , 스티릴디아민 , 스티릴트리아민, 스티릴테트라아민 등이 있으나， 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나， 이에 한정되지 않는다. 상기 전자수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서， 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8 -히드록시퀴놀린의 시 착물; 쇼1¾를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘， 바륨 , 칼슘, 이테르븀 및 사마륨이고， 각 경우 알루미늄 층 또는실버층이 뒤따른다. 상기 전자 주입층은 전극으로부터 전자를 주입하는 층으로， 전자를 수송하는 능력을 갖고， 음극으로부터의 전자 주입 효과， 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며， 발광층에서 생성된 여기자의 정공 주입층에의 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- 2019/209031 1»（：1^1{2019/004969 Pyrene, anthracene, chrysene, and periplanthene having an arylamino group. Examples of the styrylamine compound include a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, an aryl group, a silyl group, A substituent selected from the group consisting of an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto. The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As an electron transporting material, a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include a complex of 8-hydroxyquinoline; Complexes containing show 1¾; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum or silver layer in each case. The electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds and nitrogen-containing five-membered ring derivatives; and the like, but are not limited thereto. As said metal complex compound, 8-hydroxyquinolinato lithium, bis (8- 2019/209031 1 »（： 1 ^ 1 {2019/004969
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）갈륨 등이 있으나， 이에 한정되지 않는다. 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다. 상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다. 제조예 1： 중간체 5의 제조 Hydroxyquinolinato zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl- 8-hydroxyquinolinato aluminum tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [biquinolinato] beryllium, bis (10-hydroxybenzo [biquinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0-cresolato) gallium, bis (2-methyl-8-quinolinato) （1-naphthol Lato aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, etc., are not limited to this. The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto. Production Example 1 Preparation of Intermediate 5
Figure imgf000025_0001
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Figure imgf000025_0001
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1) 화합물 A-1의 합성 1) Synthesis of Compound A-1
2 -브로모펜올 (49.4 g, 287.3 mmol) 및 2 -클로로- 6 -플루오로페닐보론산 (50.0 g, 287.3 mmol)를 테트라하이드로퓨란 (THF) 500 ml에 녹였다. 여기에 탄산나트륨 (Na2C03) 2M 용액 (430 mL), 테트라키스 (트리페닐포스핀)팔라듐 (0)2-bromophenol (49.4 g, 287.3 mmol) and 2-chloro-6-fluorophenylboronic acid (50.0 g, 287.3 mmol) were dissolved in 500 ml of tetrahydrofuran (THF). Sodium carbonate (Na 2 CO 3 ) 2M solution (430 mL), tetrakis (triphenylphosphine) palladium (0)
[Pd(PPh3)4](10.0 g, 8.6 mmol)을 넣고 12 시간 환류시켰다. 반응이 끝난 후 상온으로 냉각시키고, 생성된 혼합물을 물과 톨루엔으로 3회 추출하였다. 톨루엔 층을분리한뒤 황산마그네슘 (magnesium sulfate)으로 건조하여 여과한 여액을 감압 증류하여 얻은 혼합물을 클로로폼 및 핵산을 이용한 컬럼크포마토그래피에서 정제하여 화합물 A-U34.4 g, 수율 54 을 얻었다. [Pd (PPh 3 ) 4 ] (10.0 g, 8.6 mmol) was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, and the filtrate was filtered and distilled under reduced pressure. The mixture was purified by column chromatography using chloroform and nucleic acid to obtain Compound A-U34.4 g, yield 54. .
MS:_]+=223 MS: _] + = 223
2) 화합물 A-2의 합성 2) Synthesis of Compound A-2
화합물 A-K30 g, 135.1 _ol)를 클로로포름 300 ml에 용해시킨다. 여기에 N-브로모석시드이미드 (160.3 g, 270.25 mmol)을 넣고 실온에서 4 시간 동안 교반하였다. 반응이 종료된 후 물을 첨가한다. 이후 층분리 후 소둠싸이오설페이트 솔루션으로 2차례 교반후 층분리 하였다. 이후 증류하여 화합물 A-2(51.1 g, 수율 100幻을 얻었다.  30 g of compound A-K, 135.1 _ol) are dissolved in 300 ml of chloroform. N-bromosuccinimide (160.3 g, 270.25 mmol) was added thereto and stirred at room temperature for 4 hours. After the reaction is completed, water is added. Thereafter, the layers were separated and stirred two times with sodium thiosulfate solution, followed by layer separation. Distillation was carried out to give compound A-2 (51.1 g, yield 100 kPa).
MS:_]+=379 MS: _] + = 379
3) 화합물 A-3의 합성 3) Synthesis of Compound A-3
화합물 A-2(51.1 g， 135.1 mmol)을 증류된 다이메틸포름아마이드 (DMF) (400ml)에 녹인다. 이를 0°C 로 냉각시키고， 여기에 나트륨하이드리드 (sodium hydride)(3.5 g, 145.9 mmol)를 천천히 적가하였다. 20분동안 교반한 뒤 100°C에서 1시간 동안 교반하였다. 반응이 종료된 후 상온으로 냉각하고, 에탄올 (Ethanol) 100 ml을 천천히 넣었다. 위 혼합물을 감압증류 하여 얻은 혼합물을 클로로포름 및 에틸아세테이트로 재결정하여 화합물 A-3C32.9 g, 수율 68 을 얻었다. Compound A-2 (51.1 g, 135.1 mmol) is dissolved in distilled dimethylformamide (DMF) (400 ml). It was cooled to 0 ° C, and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the mixture was stirred at 100 ° C for 1 hour. After the reaction was completed and cooled to room temperature, 100 ml of ethanol (Ethanol) was slowly added. The mixture obtained by distillation under reduced pressure was recrystallized with chloroform and ethyl acetate to give a compound A-3C32.9 g, yield 68.
MS:[M+H]+=359 2019/209031 1»（：1^1{2019/004969 MS: [M + H] + = 359 2019/209031 1 »（： 1 ^ 1 {2019/004969
4) 화합물 A-4의 합성 4) Synthesis of Compound A-4
화합물 A-3C32.9 g, 91.9 mmol) 및 페닐 보론산 (24.7 g, 202.3 mmol)를 테트라하이드로퓨란 (THF)300 ml에 녹였다. 여기에 탄산칼륨 (K2C03) 2 M 용액 (140 mL), 테트라키스 (트리페닐포스핀)팔라듐 (0) [Pd(PPh3)4] (2.1 g, 2 mol%)을 넣고 6 시간동안환류시켰다. 반응이 끝난후 상온으로 냉각시키고, 생성된 혼합물을 물과 톨루엔으로 3회 추출하였다. 톨루엔층을 분리한 뒤 황산마그네슘 (magnesium sulfate)으로 건조하여 여과한 여액을 감압 증류하여 얻은 혼합물을 클로로폼 및 에틸아세테이트를 이용해 재결정 하여 화합물 A- 4(20.8 g, 수율 64 «을얻었다. Compound A-3C32.9 g, 91.9 mmol) and phenyl boronic acid (24.7 g, 202.3 mmol) were dissolved in 300 ml of tetrahydrofuran (THF). Potassium carbonate (K 2 CO 3 ) 2 M solution (140 mL), tetrakis (triphenylphosphine) palladium (0) [Pd (PPh 3 ) 4 ] (2.1 g, 2 mol%) were added thereto for 6 hours. During reflux. After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, and the filtrate was filtered and distilled under reduced pressure. The mixture was recrystallized with chloroform and ethyl acetate to obtain Compound A-4 (20.8 g, yield 64 «).
MS:_]+=355 MS: _] + = 355
5) 화합물 A-5의 합성 5) Synthesis of Compound A-5
화합물 A-4(20.8 g, 58.7 mmol), 비스 (피나콜라토)디보론 (Bis(pinacolato)diborone)(25.0 g, 70.6 mmol), 포타슘아세테이트 (potassium acetate)(16.9 g, 176.2 mmol), 비스 (디벤질리딘아세톤)팔라듐 (1.0 g, 1.8 mmol)및 트리사이클로핵실포스핀 (1.0 g, 3.5 mmol)을 다이옥세인 (300 ml)에 넣고 12시간 동안 환류시켰다. 반응이 종료된 후 상온으로 식힌 뒤 감압 증류하여 용매를 제거하였다. 이것을클로로포름 (Chloroform)에 녹이고물로 3회 씻어낸 뒤 유기층을 분리하여 황산 마그네슘 (Magnesium sulfate)으로 건조하였다. 이를감압증류하여 화합물 A-5C25.0 g, 수율 77 «을제조하였다.  Compound A-4 (20.8 g, 58.7 mmol), Bis (pinacolato) diborone (25.0 g, 70.6 mmol), Potassium acetate (16.9 g, 176.2 mmol), Bis (Dibenzylideneacetone) palladium (1.0 g, 1.8 mmol) and tricyclonucleosilphosphine (1.0 g, 3.5 mmol) were added to dioxane (300 ml) and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and then distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water, and then the organic layer was separated and dried over magnesium sulfate. It was distilled under reduced pressure to prepare Compound A-5C25.0 g, yield 77 «.
MS： [M+H]+=447 MS: [M + H] + = 447
[실시예 ] EXAMPLE
실시예 1： 화합물 1의 제조 2019/209031 1»（：1^1{2019/004969
Figure imgf000028_0001
Example 1 Preparation of Compound 1 2019/209031 1 »（： 1 ^ 1 {2019/004969
Figure imgf000028_0001
넣고 교반 및 환류하였다. 이
Figure imgf000028_0002
67 1 01)를 물 30 에 녹여 투입한 후 충분히 교반 후 테트라키스 (트리페닐포스핀)팔라듐 (0) ＜1 1¾3)4]
Figure imgf000028_0003
2.2 _01)을 투입하였다. 4시간 반응 후 상온으로 온도를 낮추고 여과하였다. 여과물을 클로로포름과 물로 추출한 후 유기층을 황산마그네슘을 이용해 건조하였다. 이후 유기층을 감압증류 후 에틸 아세테이트를 이용해 재결정하였다. 생성된 고체를 여과후 건조하여 화합물 1 Stir and reflux. this
Figure imgf000028_0002
67 1 0 1) is dissolved in water 30 and added, followed by stirring sufficiently. Tetrakis (triphenylphosphine) palladium (0) <1 1¾ 3 ) 4 ]
Figure imgf000028_0003
2.2 _ 0 1) was added. After 4 hours the reaction was cooled to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid is filtered and dried to compound 1
Figure imgf000028_0004
상기 반응식과 같이， 2 -클로로- 4,6 -디페닐- 1，3,5 -트리아진 대신 2 - 2019/209031 1»（：1^1{2019/004969
Figure imgf000028_0004
As in the above scheme, 2 -chloro-4,6-diphenyl-1,3,5-triazine instead of 2- 2019/209031 1 »（： 1 ^ 1 {2019/004969
([1,1’-비페닐]- 4 -일)- 4 -클로로- 6 -페닐- 1，3, 5 -트리아진을 반응에 사용하는 것을 것을 제외하고는， 상기 실시예 1과 동일한 방법으로, 화합물 2
Figure imgf000029_0001
77%)을 제조하였다. The same method as in Example 1, except that ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was used in the reaction. As compound 2
Figure imgf000029_0001
77%) was prepared.
Figure imgf000029_0002
상기 반응식과 같이, 2 -클로로- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 9-(4- 클로로- 6 -페닐- 1,3, 5 -트리아진- 2 -일)-班卜카바졸을 반응에 사용하는 것을 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 화합물 3 (9.5
Figure imgf000029_0003
66%)을 제조하였다.
Figure imgf000029_0002
9- (4-chloro-6-phenyl-1,3,5-triazine-2-yl) instead of 2-chloro-4-, 6-diphenyl-1,3,5-triazine Compound 3 (9.5) in the same manner as in Example 1, except that Yokkabazole was used in the reaction.
Figure imgf000029_0003
66%) was prepared.
_]+ = 628 실시예 4： 화합물 4의 제조 _] + = 628 Example 4: Preparation of Compound 4
Figure imgf000029_0004
상기 반응식과 같이, 2 -클로로- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2- 2019/209031 1»（：1^1{2019/004969
Figure imgf000029_0004
As shown in the above scheme, 2- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. 2019/209031 1 »（： 1 ^ 1 {2019/004969
클로로- 4-（디벤조比,（1］퓨란 -4 -일）- 6 -페닐- 1，3,5 -트리아진을 반응에 사용하는 것을 것을 제외하고는, 상기 실시예 1과 동일한 방법으로， 화합물 4
Figure imgf000030_0001
51%）을제조하였다. In the same manner as in Example 1, except that chloro-4- (dibenzoy-, (1] furan-4-yl) -6-phenyl-1,3,5-triazine was used in the reaction. ， Compound 4
Figure imgf000030_0001
51%) was manufactured.
!£： ［¾1州］+ = 642 실시예 5： 화합물 5의 제조 ! £ ： [¾1 state] + = 642 Example 5 Preparation of Compound 5
Figure imgf000030_0002
Figure imgf000030_0002
5 상기 반응식과 같이， 2 -클로로- 4, 6 -디페닐- 1， 3, 5 -트리아진 대신 2- 클로로- 4-（디벤조
Figure imgf000030_0003
페닐- 1,3,5 -트리아진을 반응에 사용하는 것을 것을 제외하고는, 상기 실시예 1과 동일한 방법으로, 화합물 5
Figure imgf000030_0004
63%）을제조하였다. 5 As in the above scheme, 2-chloro-4 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
Figure imgf000030_0003
Compound 5 in the same manner as in Example 1, except that phenyl-1,3,5-triazine was used in the reaction
Figure imgf000030_0004
63%) was manufactured.
¾保: ［¾1대］+ = 658 ¾ 保: [¾1] + = 658
Figure imgf000030_0005
2019/209031 1»（：1^1{2019/004969
Figure imgf000030_0005
2019/209031 1 »（： 1 ^ 1 {2019/004969
상기 반응식과 같이, 2 -클로로- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 9-（4- （4 -클로로- 6 -페닐- 1,3, 5 -트리아진- 2 -일）페닐）-예-카바졸을 반응에 사용하는 것을 것을 제외하고는， 상기 실시예 1과 동일한 방법으로， 화합물 6
Figure imgf000031_0001
81%）을 제조하였다. As shown in the above reaction scheme, 9- (4- (4-chloro-4-6-phenyl-l, 3,5-triazine-2-2) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. Compound 6), in the same manner as in Example 1, except for using phenyl) -ex-carbazole in the reaction.
Figure imgf000031_0001
81%) was prepared.
Figure imgf000031_0002
상기 반응식과 같이, 2 -클로로- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 9-（3- （4 -클로로- 6 -페닐- 1 , 3 , 5 -트리아진- 2 -일）페닐）-애-카바졸을 반응에 사용하는 것을 것을 제외하고는， 상기 실시예 1과 동일한 방법으로, 화합물 7
Figure imgf000031_0003
53%）을 제조하였다.
Figure imgf000031_0002
As shown in the above scheme, 9- (3- (4- (4-chloro-6-phenyl-1,3,5-triazine-2-2-) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. Compound 7) in the same manner as in Example 1, except for using phenyl) -a-carbazole in the reaction.
Figure imgf000031_0003
53%).
13： [¾_+ = 717 실시예 8： 화합물 8의 제조 13: [¾_ + = 717 Example 8 Preparation of Compound 8
Figure imgf000031_0004
2019/209031 1»（：1^1{2019/004969
Figure imgf000031_0004
2019/209031 1 »（： 1 ^ 1 {2019/004969
상기 반응식과 같이, 2 -클로로- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 - 클로로- 6 -페닐- 1,3, 5 -트리아진- 2 -일)- 9 -페닐- -카바졸을 반응에 사용하는 것을 것을 제외하고는， 상기 실시예 1과 동일한 방법으로， 화합물 8
Figure imgf000032_0001
59%)을 제조하였다. As in the above scheme, 2- (4-chloro-6-phenyl-1,3,5-triazine-2-yl) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. Compound 8, in the same manner as in Example 1, except that 9-phenyl-carbazole is used in the reaction.
Figure imgf000032_0001
59%) was prepared.
1此: ［¾1+비+ = 717 실시예 9： 화합물 9의 제조 1 ′: [¾1 + ratio + = 717 Example 9: Preparation of compound 9
Figure imgf000032_0002
상기 반응식과 같이， 2 -클로로- 4,6 -디페닐- 1，3,5 -트리아진 대신 3-(4- 클로로- 6 -페닐- 1,3, 5 -트리아진- 2 -일)- 9 -페닐-班!-카바졸을 반응에 사용하는 것을 것을 제외하고는, 상기 실시예 1과 동일한 방법으로， 화합물 9
Figure imgf000032_0003
Figure imgf000032_0002
As in the above scheme, 3- (4-chloro-6-phenyl-1,3,5-triazine-2-yl)-instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Compound 9, in the same manner as in Example 1, except that 9-phenyl- 班! -Carbazole is used in the reaction.
Figure imgf000032_0003
74%)을 제조하였다. 74%) was prepared.
［¾1+비+ = 717 (¾1 + ratio + = 717
［실험예］ [Experimental example]
실험예 1  Experimental Example 1
IT0( indium tin oxide)가 1,300A의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때， 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며， 증류수로는 밀리포어사 (Mi 11 ipore Co.) 제품의 필터 (Filter)로 2차로 걸러진 증류수를 사용하였다. IT0를 30분간 세척한 후 층류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜， 아세톤 및 메탄올의 용제로 초음파 세척을 2019/209031 1»（：1^1{2019/004969 A glass substrate coated with a thin film of I0 (indium tin oxide) having a thickness of 1,300 A was put in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as the detergent, and distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as the distilled water. After washing IT0 for 30 minutes, the ultrasonic cleaning was repeated 10 times with laminar flow twice. After the distilled water has been washed, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone and methanol 2019/209031 1 »（： 1 ^ 1 {2019/004969
하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간세정한후 진공 증착기로 기판을 수송시켰다. And dried and then transported to a plasma cleaner. In addition, the substrate was washed with oxygen plasma for 5 minutes and then transported to a vacuum evaporator.
상기와 같이 준비된 110 투명 전극 위에 하기 -1 화합물을 50入의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 -1 화합물을 250入의 두께로 열 진공 증착하여 정공수송층을 형성하고, 상기 정공수송증 위에 하기
Figure imgf000033_0001
화합물을 50쇼 두께로 진공 증착하여 전자저지층을 형성하였다. 상기 전자저지층 위에 발광층으로서 앞서 실시예 1에서 제조한 화합물 1， 하기 애-1 화합물, 및 인광 도펀트 ¥01)-1을 44: 44 : 12의 중량비로 공증착하여 400入 두께의 발광층을 형성하였다. 상기 발광층 위에 하기 -1 화합물을 250ᅀ의 두께로 진공 증착하여 전자수송층을 형성하고, 상기 전자수송층 위에 하기 £1-2 화합물 및 니를 98 : 2의 중량비로 진공 증착하여 100쇼 두께의 전자주입층을 형성하였다. 상기 전자주입층 위에 1000入 두께로 알루미늄을 증착하여 음극을 형성하였다. A hole injection layer was formed by thermal vacuum deposition of the following −1 compound to a thickness of 50 particles on the 110 transparent electrode prepared as described above. The following -1 compound was vacuum-deposited to a thickness of 250 particles on the hole injection layer to form a hole transport layer, and then on the hole transport certificate.
Figure imgf000033_0001
The compound was vacuum deposited to a thickness of 50 shows to form an electron blocking layer. Compound 1, the following compound-1, and phosphorescent dopant ¥ 01) -1 prepared in Example 1 as a light emitting layer on the electron blocking layer were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 particles. It was. The following -1 compound was vacuum deposited to a thickness of 250 위에 on the light emitting layer to form an electron transport layer, and the following £ 1-2 compound and the needle were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to inject 100 nm thick electrons. A layer was formed. Aluminum was deposited on the electron injection layer to a thickness of 1000 particles to form a cathode.
2019/209031 1»（：1/10公019/004969 2019/209031 1 »（： 1/10 公 019/004969
Figure imgf000034_0001
Figure imgf000034_0001
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7요 를유지하였고， 알루미늄은 2 ᅀ/3 의 증착속도를유지하였으며， 증착시 진공도는 1 X 10一7 ~ 5 X 10 8 ^를유지하였다. 실험예 2내지 9및 비교실험예 1내지 3 2019/209031 1»（：1^1{2019/004969 In the above process, the deposition rate of organic material was maintained at 0.4 ~ 0.7, aluminum was maintained at a deposition rate of 2 ᅀ / 3, and the vacuum degree during deposition was maintained at 1 X 10 one 7 ~ 5 X 10 8 ^ . Experimental Examples 2 to 9 and Comparative Experimental Examples 1 to 3 2019/209031 1 »（： 1 ^ 1 {2019/004969
상기 실시예 1에서 제조된 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는， 상기 실험예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Experiment 1, except that the compound shown in Table 1 was used instead of the compound 1 prepared in Example 1.
다만， 하기 표 1의 CE1 CE12 및 CE3 화합물은 하기와 같다.  However, the CE1 CE12 and CE3 compounds of the following Table 1 are as follows.
Figure imgf000035_0001
상기 실험예 및 비교실험예의 유기 발광 소자를 10—/0112의 전류 밀도에서 전압과 효율을 측정하였고， 50 八: #의 전류 밀도에서 수명을 측정하고, 그 결과를 하기 표 1에 나타내었다. 이때， 1그95는 초기 휘도 대비 95%가 되는 시간을 의미한다.
Figure imgf000035_0001
The organic light emitting diodes of the Experimental Example and the Comparative Experimental Example were measured voltage and efficiency at a current density of 10— / 011 2 , and lifespan was measured at a current density of 50 八: #, and the results are shown in Table 1 below. At this time, 1 95 means the time to be 95% of the initial luminance.
【표 1】 Table 1
Figure imgf000035_0002
2019/209031 1»（：1^1{2019/004969
Figure imgf000035_0002
2019/209031 1 »（： 1 ^ 1 {2019/004969
Figure imgf000036_0001
Figure imgf000036_0001
상기 표 1을 참고하면， 본 발명의 화합물을 발광층 물질로 사용한 실험예는， 비교실험예에 비하여， 전압이 현저히 낮고， 효율 및 수명이 우수한 특성을 나타내는 것을 확인했다. 구체적으로, 실시예 1 내지 9에서 제조된 화합물 1 내지 9는， 다이벤조퓨란치환기의 2번과 4번 위치가 페닐로 치환됨에 따라， 이를 유기 발광 소자의 호스트로 사용하는 경우, 유기 발광 소자의 전자안정성이 우수한 것으로 예측된다. Referring to Table 1, the experimental example using the compound of the present invention as a light emitting layer material, it was confirmed that compared to the comparative example, the voltage is significantly lower, and the efficiency and life is excellent. Specifically, Compounds 1 to 9 prepared in Examples 1 to 9, as positions 2 and 4 of the dibenzofuran substituent are substituted with phenyl, and when used as a host of the organic light emitting device, It is expected that the electron stability is excellent.
【부호의 설명】 [Explanation of code]
1： 기판 2： 양극  1 ： Substrate 2 ： Anode
3： 발광층 4： 음극  3: light emitting layer 4: cathode
5 : 정공주입층 6： 정공수송층  5: hole injection layer 6: hole transport layer
7 : 전자저지층 8： 전자수송층  7: electronic blocking layer 8: electron transport layer
9： 전자주입층  9: electron injection layer

Claims

2019/209031 1»（：1^1{2019/004969 【청구범위】 【청구항 11 하기 화학식 1로 표시되는 화합물: 2019/209031 1 »（： 1 ^ 1 {2019/004969 【claims】 【claim 11】 Compound represented by the following formula 1:
[화학식 1]  [Formula 1]
Figure imgf000037_0001
Figure imgf000037_0001
상기 화학식 1에서, In Chemical Formula 1,
은 0또는 £이고，  Is 0 or £,
쇼 은 치환된 06-60 아릴; 또는 치환 또는 비치환된 0 , 比 및 £로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상을 포함하는 01-60 헤테로아릴이고, Show is substituted 0 6-60 aryl; Or 0 1 -60 heteroaryl including one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, 比 and £,
은 단일 결합 ; 치환 또는 비치환된 06-60 아릴텐 ; 또는 치환 또는 비치환된 0 , 및 £로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상을 포함하는 01-60 헤테로아릴텐이고， Is a single bond; Substituted or unsubstituted 0 6 -60 arylten; Or 0 1 -60 heteroarylten containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, and £,
¾ 내지 ¾는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로 ; 아미노 ; 치환 또는 비치환된 -60 알킬 ; 치환 또는 비치환된 01-60 할로알킬 ; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 01-60 할로알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 02-60 알케닐 ; 치환 또는 비치환된 06-60 아릴 ; 치환 또는 비치환된 06-60 아릴옥시 ; 또는 치환 또는 비치환된 凡 0 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 01-60 헤테로아릴이고， ¾ to ¾ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted- 60 alkyl; Substituted or unsubstituted 0 1-60 haloalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 01-60 haloalkoxy; Substituted or unsubstituted 0 3-60 cycloalkyl; Substituted or unsubstituted 0 2 -60 alkenyl; Substituted or unsubstituted 0 6-60 aryl; Substituted or unsubstituted 0 6-60 aryloxy; Or 0 1-60 heteroaryl which contains one or more heteroatoms selected from the group consisting of substituted or unsubstituted 凡 0 and
111 내지 은 각각 독립적으로， 1 내지 5의 정수이다.  111 to are each independently an integer of 1 to 5.
【청구항 2] [Claim 2]
제 1항에 있어서, 2019/209031 1»（：1^1{2019/004969
Figure imgf000038_0002
The method of claim 1, 2019/209031 1 »（： 1 ^ 1 {2019/004969
Figure imgf000038_0002
Figure imgf000038_0001
Figure imgf000038_0001
상기에서 ,  Above
¾ 내지 ¾은 각각 독립적으로， 또는 0?’ 3이되 , ¾ 내지 ¾ 중 2개 이상은 이고， ¾ to ¾ are each independently or 0? ' 3 , at least two of ¾ to ¾ are
^2 및 3은 각각 독립적으로, 0 , 3 또는 ■’ 이고， ^ 2 and 3 are each independently 0, 3 or ■ ’
2 내지 5는 각각 독립적으로 , 치환 또는 비치환된 06-60 아릴 ; 또는 치환 또는 비치환된 0 , 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상을 포함하는 01-60 헤테로아릴이고, 2 to 5 each independently represent a substituted or unsubstituted 0 6-60 aryl; Or substituted or unsubstituted 0, and 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of
요’ 는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노 ; 치환 또는 비치환된 01-60 알킬 ; 치환 또는 비치환된 01-60 할로알킬 ; 치환 또는 비치환된 01-60 알콕시 ; 치환 또는 비치환된 01-60 할로알콕시 ; 치환 또는 비치환된 03-60 사이클로알킬 ; 치환 또는 비치환된 02-60 알케닐 ; 치환 또는 비치환된 06-60 아릴 ; 치환 또는 비치환된 06-60 아릴옥시 ; 또는 치환 또는 비치환된 0 및 £로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 01-60 헤테로아릴이고 , Each yaw is independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0 1 -60 haloalkyl; Substituted or unsubstituted 01-60 alkoxy; Substituted or unsubstituted 01-60 haloalkoxy; Substituted or unsubstituted 0 3 -60 cycloalkyl; Substituted or unsubstituted 0 2 -60 alkenyl; Substituted or unsubstituted 0 6 -60 aryl; Substituted or unsubstituted 0 6 -60 aryloxy; Or 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0 and £,
114 내지 1111은 각각 독립적으로， 1 내지 5의 정수이다. 2019/209031 1»（：1^1{2019/004969 114 to 1111 are each independently an integer of 1 to 5; 2019/209031 1 »（： 1 ^ 1 {2019/004969
【청구항 3] [Claim 3]
제 1항에 있어서,  The method of claim 1,
쇼 은 하기로 구성되는 군으로부터 선택되는 어느 하나인，  The show is any one selected from the group consisting of
Figure imgf000039_0001
상기에서， 2019/209031 1»（：1^1{2019/004969 2 및 5 에 대한설명은 제 2항에서 정의한 바와 같다.
Figure imgf000039_0001
Above 2019/209031 1 »（： 1 ^ 1 {2019/004969 The description of 2 and 5 is as defined in paragraph 2.
【청구항 4] [Claim 4]
제 1항에 있어서,  The method of claim 1,
느은 단일 결합， 또는 하기로 구성되는 군으로부터 선택되는 어느 하나인， 화합물:  Which is a single bond or any one selected from the group consisting of:
Figure imgf000040_0001
Figure imgf000040_0001
【청구항 5] [Claim 5]
제 1항에 있어서，  The method of claim 1,
¾ 내지 ¾은 각각 독립적으로, 수소; 중수소; 시아노; 또는 치환 또는 비치환된 01-10 알킬인， 화합물 .  ¾ to ¾ are each independently hydrogen; heavy hydrogen; Cyano; Or substituted or unsubstituted 01-10 alkyl.
【청구항 6】 [Claim 6]
제 1항에 있어서，  The method of claim 1,
상기 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인， 화합물: The compound is any one selected from the group consisting of the following compounds:
Figure imgf000041_0001
Figure imgf000041_0001
40 40
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000047_0001
 2019/209031 1»（：1^1{2019/004969  2019/209031 1 »（： 1 ^ 1 {2019/004969
【청구항 7] [Claim 7]
제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물 층 중 1층 이상은 제 1항 내지 제 6항 중 어느 하나의 항에 따른 화합물을 포함하는 것인， 유기 발광소자.  A first electrode; A second electrode provided to face the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers is a compound according to any one of claims 1 to 6. That comprises a, organic light emitting device.
【청구항 8] [Claim 8]
제 7항에 있어서,  The method of claim 7, wherein
상기 화합물을 포함하는 유기물 층은 정공주입층， 정공수송층, 전자저지층, 발광층， 전자수송층， 또는 전자주입층인， 유기 발광소자.  The organic material layer comprising the compound is a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, or an electron injection layer, an organic light emitting device.
【청구항 9】 [Claim 9]
제 7항에 있어서，  The method of claim 7,
상기 발광층은 2종 이상의 호스트를 포함하고, 상기 호스트 중 하나가 상기 화합물인, 유기 발광소자.  The light emitting layer includes two or more types of hosts, and one of the hosts is the compound.
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