WO2019139233A1 - Heterocyclic compound and organic light emitting element using same - Google Patents

Heterocyclic compound and organic light emitting element using same Download PDF

Info

Publication number
WO2019139233A1
WO2019139233A1 PCT/KR2018/013120 KR2018013120W WO2019139233A1 WO 2019139233 A1 WO2019139233 A1 WO 2019139233A1 KR 2018013120 W KR2018013120 W KR 2018013120W WO 2019139233 A1 WO2019139233 A1 WO 2019139233A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
synthesis
group
represented
Prior art date
Application number
PCT/KR2018/013120
Other languages
French (fr)
Korean (ko)
Inventor
하재승
김연환
이성재
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 KR1020180124557A external-priority patent/KR102126884B1/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880048910.3A priority Critical patent/CN110944991B/en
Publication of WO2019139233A1 publication Critical patent/WO2019139233A1/en

Links

Classifications

    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10Organic polymers or oligomers
    • H10K85/111Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • C07D209/82Carbazoles; Hydrogenated carbazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91Dibenzofurans; Hydrogenated dibenzofurans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14Carrier transporting layers
    • H10K50/16Electron transporting layers

Definitions

  • the present invention relates to a heterocyclic compound and an organic light emitting device including 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, and excellent researches on the luminance, driving voltage and response speed.
  • 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 made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present invention relates to a heterocyclic compound compound and an organic light emitting device comprising the same.
  • One of the remaining excluding XI to XI is 3 ⁇ 4, and the remaining excluding the medium to 3 ⁇ 4 are hydrogen, respectively.
  • 3 ⁇ 4 are each independently represented by the following Chemical Formula 2 or 3, and at least one of 3 ⁇ 4 is represented by the following Chemical Formula 2,
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently 0 or N, at least one of 3 ⁇ 4 to 3 ⁇ 4 is ⁇ ,
  • 1 to 14 are each independently, bound; Or substituted or unsubstituted 0 6-60 arylene,
  • 3 to 3 each independently represent a substituted or unsubstituted 0 6 -60 6 _ aryl group; Or a 0 2 -60 heteroaryl group including one or more of 0, ⁇ and substituted or unsubstituted,
  • I, 1 , ..., and 3 are each independently an integer of 0-3.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode according to one embodiment of the present invention, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. .
  • the compound represented by Formula 1 in another embodiment of the present invention, may be grooved with a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
  • 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.
  • *-and 3 ⁇ 4 each mean a bond connected to another substituent.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of 0
  • the "substituent to which two or more substituents are linked” may be a biphenyl group. That is, the biphenyl group may be an aryl group and may be interpreted as a substituent to which two phenyl groups are linked.
  • the carbon number of the carbonyl group is not particularly limited. , It is preferable to have 1 to 40 carbon atoms.
  • the compound may have the following structure, but is not limited thereto. 2019/139233 1 »(: 1 ⁇ 1 ⁇ 2018/013120
  • the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • the compound may have the following structure, but is not limited thereto.
  • the silyl group specifically includes trimethylsilyl group, triethylsilyl group, 1 butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited to this. 2019/139233 1 »(: 1 ⁇ 1 ⁇ 2018/013120
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, 1-butyldimethyl boron group, a triphenyl boron group, a 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. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • the alkyl group has 1 to 6 carbon atoms.
  • alkyl groups are methyl, ethyl, propyl, 11 _ propyl, isopropyl, butyl, I: tert-butyl, isobutyl, La-butyl, t-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, 11 _ Pentyl, isopentyl, neopentyl, horatinpanyl, nuclear chamber, 11 -nuclear chamber, 1 -methylpentyl, 2 -methylpentyl, 4 -methyl-2 -pentyl, 3,3-dimethylbutyl, 2 -ethylbutyl, heptyl, 11-heptyl, 1-methyl haeksil, cyclopentylmethyl, cyclohexyl haektil methyl, octyl, -
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms.
  • 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 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • 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, for example, a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
  • the heterocyclic group is a heterocyclic group including one or more of 0, rain, and the like as a dissimilar element.
  • the carbon number is not particularly limited, it is preferably 2 to 60 carbon atoms.
  • the heterocyclic group 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, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group , Indole group, carbazole group, benzox
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as 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 heterocyclic group.
  • 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.
  • the heteroarylene is a divalent group, the description of the aforementioned heterocyclic group may be applied.
  • 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 heterocyclic ring is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • 3 ⁇ 4 and 3 ⁇ 4 are each independently represented by Formula 2 or 3, And at least one of 3 ⁇ 4 is represented by the following Chemical Formula 2.
  • 3 ⁇ 4 is represented by Formula 2 and ⁇ is represented by Formula 3; And it is represented by the formula (2) and except the case represented by the formula (3).
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-21, depending on the bonding position of 11 and 3 ⁇ 4.
  • Chemical Formulas 1-1 to 1-21 illustrate the case where all the rest except hydrogen, to medium, and 3 ⁇ 4 are hydrogen:
  • Chemical Formula 1 When the compound represented by Chemical Formula 1 is represented by Chemical Formula 1-2, is represented by Chemical Formula 2, and Chemical Formula 3 ⁇ 4 is represented by Chemical Formula 2 or 3.
  • ni may be phenylene.
  • To ⁇ 3 are each independently phenyl unsubstituted or substituted with any one substituent selected from the group consisting of 0 1-4 alkyl, halogen, cyano, and tri ( -4 alkyl) silyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethyl fluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl.
  • at least one of 1 and 2 may be a phenyl group.
  • the compound represented by Formula 1 is any one selected from the number of days doeneungun configured to.
  • an organic light emitting element including the compound represented by Chemical Formula 1 in at least one layer of the organic layer, and the configurations, structures, and the like except for the compound represented by Chemical Formula 1 may be the same as those generally known in the art. have.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting the hole, the hole injection layer, the hole transport layer, or
  • a layer for simultaneously injecting and transporting a hole includes the compound represented by Chemical Formula 1.
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic layer may include an electron transport layer or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).
  • the electron transport layer, the electron injection layer, or the layer for the electron transport and the electron injection at the same time includes the compound represented by the formula (1).
  • the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include 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 layers and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device having 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 show 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.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes 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 device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • PVD physical vapor deposition
  • an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode 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 material 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 to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material 0 2003/012890).
  • the manufacturing method is not limited to this.
  • 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 110, indium zinc oxide 1a0; Combinations of metals and oxides, such as 3 ⁇ 40: hour or 3 ⁇ 2: 3 ⁇ 4 ; 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; ⁇ 1 or Multilayer materials such as Li3 ⁇ 4Ml, but not limited to them.
  • 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, and is produced in the light emitting layer
  • 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.
  • H0M0 highest occupied molecul ar orbital
  • the hole injection material include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but not limited to these.
  • the hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer.
  • a hole transporting material is a material capable of receiving holes from an anode or a hole injection layer and transferring the holes to the light emitting layer. Suitable. Specific examples include arylamine-based organics, conductive polymers, and block copolymers having both conjugated and non-conjugated portions, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the light emitting layer may include a host material and a dopant material.
  • 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 gluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder type. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound is substituted or unsubstituted.
  • a substituent selected from the group consisting of an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex and a platinum complex.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • 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, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, the effect of electron injection from the cathode, the light emitting layer or light emission 2019/139233 1 »(: 1 ⁇ 1 ⁇ 2018/013120
  • generated in the light emitting layer to the hole injection layer, and is excellent in thin film formation ability is preferable .
  • fluorenone anthraquinodimethane, diphenoquinone , thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinatolium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, Tris (2-methyl-8-hydroxyquinolinato) aluminum, Tris (8-hydroxyquinolinato) gallium , bis ( 10 -hydroxybenzo 3 ⁇ 4] qui Nolinato) beryllium, bis (10-hydroxybenzo [biquinolinato] zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( 0- cresol Rato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, etc., are not limited to this.
  • the organic light emitting device may be a front light emitting type, a back light emitting type or a double light emitting 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.
  • Synthesis of 32 62 was prepared by synthesizing in the same manner, except that in the synthesis of Y2, instead of yarn was used.
  • Synthesis of 02 was carried out in the same manner as in Synthesis of Show 2 except that Da was used instead of Sa.
  • Synthesis of Show 3 was carried out in the same manner as in Synthesis of Show 3 except that F 2 was used instead of Show 2.
  • Compound 6 was prepared in the same manner except for using (naphthalene-2-yl) -6-phenyl-1,3,5-triazine.
  • Synthesis of 02 Synthesis of G2 was carried out in the same manner as in Synthesis of Show 2 except that A was used instead of S.
  • Compound 7 was prepared in the same manner except for using (naphthalene-1-yl) -6-phenyl-1,3,5-triazine.
  • Synthesis of 2 was carried out in the same manner as in the synthesis of Show 3, except that ⁇ was used instead of Show 2. 2019/139233 1 »(: 1/10 ⁇ 018/013120 482.40
  • 3-bromo-8-chloroquinoline was replaced by 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2) instead of triphenylene-2-ylboronic acid.
  • Dioxaborolane 2-yl) phenyl) 1,3, 5- Triazine was synthesized in the same manner except that triazine was used to produce a child.
  • Synthesis of 02 was carried out in the same manner as in Example 2 except that Ah was used instead to prepare 02.
  • 11X3 Indium Tin Oxide
  • distilled water was used as the secondary distilled water and filtered by filter ⁇ 11 O 6 0 0. products (D). After washing 0 for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried.
  • Nuclear nitrile nucleated azatriphenylgirene on the 110 transparent electrode thus prepared 111-1) was vacuum-deposited to a thickness of 500 yaw to form a hole injection layer. Thereafter, 1111 (900 kPa), a material for transporting holes, was vacuum deposited, followed by vacuum deposition of # 2 at a film thickness of 50 kPa on the hole transport layer to form a hole control layer. Host # 1 and the dopant 301 compound (25: 1) were vacuum-deposited at the thickness of 300 pieces with the compound light emitting layer. Then, an E ⁇ : m compound (50 kV) was formed as an electron control layer and the compound synthesized in Preparation Example 1 310 sets) was sequentially formed into an electron transport layer. 10 ⁇ m thick Rimium fluoride (Niwa 3 ⁇ 43 ⁇ 4 and Shawyong (10: 1, 150 ⁇ ) was deposited on the electron transport bottle and 1,000 ⁇ thick.
  • Rimium fluoride Niwa 3 ⁇ 43 ⁇ 4
  • An organic light-emitting device was manufactured by depositing aluminum to form a cathode.
  • the deposition rate of the organic material was maintained at 1 flock, the lithium fluoride was 0.2 ⁇ ⁇ %, and the aluminum was maintained at the deposition rate of 3-7 phosphorus. 2019/139233 1 »(1 ⁇ 1 ⁇ 2018/013120
  • Example 3 Except for using the compound 4 instead of compound 2 in the electron transport layer in Example 1 was the same experiment. ⁇ Example 3>
  • Example 8 Except for using the compound 11 instead of compound 2 in the electron transport in Example 1 was the same experiment. ⁇ Example 8>
  • Example 13 Except for using the compound 7 instead of compound 2 in Example 1, and the ratio of the compound 7 and ni £ 1 1: 1 instead of 1: 1 was the same experiment.
  • Example 13 Except for using the compound 7 instead of compound 2 in Example 1, and the ratio of the compound 7 and ni £ 1 1: 1 instead of 1: 1 was the same experiment.
  • Example 13 Except for using the compound 7 instead of compound 2 in Example 1, and the ratio of the compound 7 and ni £ 1 1: 1 instead of 1: 1 was the same experiment. Example 13
  • Example 1 the electron transport certificate was tested in the same manner except that £ 11 was used instead of Compound 2.
  • Example 1 the electron transport layer was tested in the same manner except that £ 2 was used instead of Compound 2. 2019/139233 1 »(: 1 ⁇ 1 ⁇ 2018/013120
  • Example 1 the electron transport layer was tested in the same manner except that £ 12 was used instead of Compound 2, and the ratio of the electron transport layer and 110 was 2: 1 instead of 1: 1.
  • Example 1 the electron transporting layer used £ 2 instead of Compound 2.
  • Example 1 the electron transport layer was used instead of the compound 5 5 5
  • Table 1 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the electron transporting material as in Examples 1 to 14 and Comparative Examples 1 to 6.
  • a glass substrate (corning 7059 glass) coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,000 A was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves.
  • the detergent used was Fischer Co.'s product.
  • Secondly filtered distilled water was used as a product filter. After washing IT0 for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried.
  • nucleonitrile nuxaazatriphenylgirene (hexanitrile hexaazat riphenylphenyl, HI-1) was thermally vacuum deposited to a thickness of 500 A to form a hole injection layer.
  • HT1 (900 A), which is a material for transporting holes, was vacuum deposited thereon, followed by vacuum deposition of HT2 with a film thickness of 50 A on the hole transport layer to form a hole control layer.
  • the host BH1 and the dopant BD1 compound (25: 1) were vacuum deposited to a thickness of 300 A as the compound light emitting layer.
  • Compound 1 (50A) synthesized in Preparation Example 1 was formed as an electron control layer and co-deposited with ETM2 and LiQ (1: 1, 310 A) to form an electron transport layer sequentially.
  • Lithium fluoride (LiF), Mg and Ag (10: 1, 150 A) having a thickness of 10 A was sequentially deposited on the electron transport layer, and a cathode was formed by depositing aluminum having a thickness of 1,000 A, thereby manufacturing an organic light emitting device. .
  • the deposition rate of the organic material was maintained at 1 A / sec
  • the lithium fluoride was maintained at 0.2 A / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 A / sec.
  • Example 17 Except for using Compound 3 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment. ⁇ Example 17>
  • Example 15 The same experiment as in Example 15 except for using the compound 21 instead of compound 1 as the electron control layer.
  • Example 1 the electron control layer was used in place of Compound 1 Compound 6,
  • Example 1 the electron control layer was used in place of Compound 1 Compound 12,
  • Example 1 the electron control layer was used in place of compound 1 compound 17,
  • Example 7 The same experiment was conducted in Example 7, except that £ 13 instead of 1 was used as the electron adjusting layer.
  • Example 9 The same experiment was conducted in Example 7, except that £ 4 instead of 1 was used as the electron adjusting layer. Comparative Example 9
  • Example 7 the electron control layer was tested in the same manner except that 7 was used instead of Compound 1.
  • Example 7 the electron control layer was tested in the same manner except that £ 18 was used instead of Compound 1.
  • Table 2 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the electron transporting material as in Examples 15-30 and Comparative Example 7 11.
  • Compound derivative of formula according to the invention is able to control the electron transport and electron role in an organic electronic device including an organic light emitting element, the element according to the invention represents the efficiency, driving voltage, excellent properties in terms of stability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

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

Description

2019/139233 1»(그1^1{2018/013120  2019/139233 1 »(1 ^ 1 {2018/013120
【발명의 명칭】 [Name of invention]
헤테로고리 화합물및 이를이용한유기발광소자 【기술분야】  Heterocyclic compound and organic light emitting device using the same
관련출원 (들)과의 상호인용  Citation with Related Application (s)
본출원은 2018년 1월 9일자한국특허 출원 제 10-2018-0002875호및 2018년 10월 18일자한국특허 출원 제 10-2018-0124557호에 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. 10-2018-0002875 dated January 9, 2018 and Korean Patent Application No. 10-2018-0124557 dated October 18, 2018. All content disclosed in the literature is included as part of this specification.
본 발명은 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한것이다.  The present invention relates to a heterocyclic compound and an organic light emitting device including the same.
【배경기술】 Background Art
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광소자는넓은시야각, 우수한콘트라스트, 빠른응답시간을가지며, 휘도, 구동전압및응답속도특성이 우수하여 많은연구가진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤 (6X^1:011)이 형성되며, 이 엑시톤이 다시 바닥상태로떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로요구되고 있다. 0 2019/139233 1»(:1^1{2018/013120 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, and excellent researches on the luminance, driving voltage and response speed. 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 made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, 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 material layer, and excitons ( 6 X ^ 1: 011) are formed when the injected holes and the electrons meet each other. It will glow when the excitons fall back to the ground. There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices. 0 2019/139233 1 »(: 1 ^ 1 {2018/013120
【발명의 상세한설명】 Detailed Description of the Invention
【기술적 과제】  [Technical problem]
본 발명은 헤테로고리 화합물 화합물 및 이를 포함하는 유기 발광 소자에 관한것이다.  The present invention relates to a heterocyclic compound compound and an organic light emitting device comprising the same.
【기술적 해결방법】 Technical Solution
본 발명의 일 구현예에서는, 하기 화학식 1로 표시되는 화합물을 제공한다:  In one embodiment of the present invention, a compound represented by the following Chemical Formula 1 is provided:
[화학식 1]  [Formula 1]
Figure imgf000003_0001
Figure imgf000003_0001
상기 화학식 1에서,  In Chemical Formula 1,
내지 중어느하나는 이고,  Or any one of
내지 XI중 을제외한나머지에서 어느하나는 ¾이고, 내지 중 및 ¾를제외한나머지는각각, 수소이고  One of the remaining excluding XI to XI is ¾, and the remaining excluding the medium to ¾ are hydrogen, respectively.
및 ¾는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 것이되, 및 ¾중적어도하나는하기 화학식 2으로표시되는것이며,  And ¾ are each independently represented by the following Chemical Formula 2 or 3, and at least one of ¾ is represented by the following Chemical Formula 2,
(단, 3이 화학식 2으로 표시되며 이 화학식 3으로 표시되는 경우; 및九가화학식 2으로표시되며 이 화학식 3으로표시되는경우를제외함) (If 3 is represented by formula (2) represented by the formula (3); And 九 are represented by the formula (2), except when represented by the formula (3).
[화학식 2]  [Formula 2]
Figure imgf000003_0002
Figure imgf000003_0002
[화학식 3]  [Formula 3]
-(1_45 -사3 -(1_ 45 -Yarn 3
상기 화학식 2및 3에서, 2019/139233 1»(:1^1{2018/013120 In Chemical Formulas 2 and 3, 2019/139233 1 »(: 1 ^ 1 {2018/013120
¾ 내지 ¾ 각각 독립적으로 0 또는 N 이되, ¾ 내지 ¾ 중 적어도 하나는 ^이고, ¾ to ¾ are each independently 0 or N, at least one of ¾ to ¾ is ^,
1그내지 14는각각독립적으로, 결합; 또는치환또는비치환된 06-60 아릴렌이고,1 to 14 are each independently, bound; Or substituted or unsubstituted 0 6-60 arylene,
: 내지 3는 각각 독립적으로, 치환 또는 비치환된 06-60 6ᅵ_릴기; 또는 치환 또는 비치환된 0 , 比 및 중 1개 이상을 포함하는 02-60 헤테로아릴기이며, 3 to 3 each independently represent a substituted or unsubstituted 0 6 -60 6 _ aryl group; Or a 0 2 -60 heteroaryl group including one or more of 0, 比 and substituted or unsubstituted,
I, 1, · , 및 3는각각독립적으로, 0내지 3의 정수이다. 또한, 본 발명의 다른 일 구현예에서는, 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2전극; 및 상기 제 1 전극과상기 제 2 전극사이에 구비된 1층 이상의 유기물층을포함하는유기 발광소자이되, 상기 유기물층중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. I, 1 , ..., and 3 are each independently an integer of 0-3. Further, in another embodiment of the present invention, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1.
【발명의 효과】 【Effects of the Invention】
상기 화학식 1로 표시되는 화합물은, 본 발명의 일 구현예에 따라, 유기 발광소자의 유기물층의 재료로사용될 수 있으며, 유기 발광소자에서 효율의 향상, 낮은구동전압및/또는수명 특성을향상시킬수있다.  The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode according to one embodiment of the present invention, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. .
특히, 상기 화학식 1로 표시되는 화합물은, 본 발명의 다른 일 구현예에서, 정공주입, 정공수송, 정공주입 및 수송, 발광, 전자수송, 또는 전자주입 재료로사홈될수있다.  In particular, the compound represented by Formula 1, in another embodiment of the present invention, may be grooved with a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
【도면의 간단한설명】 【Brief Description of Drawings】
도 1은 기판 (1) , 양극 (2) , 발광층 (3), 음극 (4)으로 이루어진 유기 발광소자의 예를도시한것이다.  FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는기판 (1), 양극 (2) , 정공주입층 (5), 정공수송층 (6) , 발광층 (7) , 전자수송층 (8) 및 음극 (4)로이루어진유기 발광소자의 예를도시한것이다. 【발명의 실시를위한최선의 형태】 2019/139233 1»(그1^1{2018/013120 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. [Best Mode for Implementation of the Invention] 2019/139233 1 »(1 ^ 1 {2018/013120
본발명의 구현예들의 이점 및 특징,그리고그것들을달성하는방법은, 상세하게 후술되어 있는 실시예들을 참조하면 명확해질 것이다. 그러나, 본 발명은이하에서 개시되는실시예들에 한정되는것이 아니라서로다른다양한 형태로 구현될 수 있으며, 단지 본 실시예들은 본 발명의 개시가 완전하도록 하고, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자에게 발명의 범주를 완전하게 알려주기 위해 제공되는 것이며, 본 발명은 청구항의 범주에 의해 정의될뿐이다. 이하에서는, 본 발명의 구현예들에 대한 상세한 설명에 앞서 , 본 명세서에서 통용되는표현, 용어 등을정의한다. 이하,본발명의 이해를돕기 위하여 보다상세히 설명한다. Advantages and features of the embodiments of the present invention and how to achieve them will become apparent with reference to the embodiments described below in detail. However, the present invention is not limited to the embodiments disclosed below, but can be embodied in various forms, and the present embodiments are merely to make the disclosure of the present invention complete, and are common in the art to which the present invention pertains. It is provided to inform those skilled in the art to the fullest extent of the invention and the invention is defined only by the scope of the claims. Hereinafter, before the detailed description of the embodiments of the present invention, the expressions, terms, and the like commonly used in the present specification are defined. Hereinafter, the present invention will be described in more detail to help understand the present invention.
4 - 본 명세서에서, * -및 ¾ 는 각각, 다른 치환기에 연결되는 결합을의미한다. 본 명세서에서 ”치환 또는 비치환된” 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기 ; 포스핀옥사이드기 ; 알콕시기 ; 아릴옥시기 ; 알킬티옥시기 ; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기 ; 알케닐기 ; 아릴기 ; 아르알킬기 ; 아르알케닐기 ; 알킬아릴기 ; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는比 0및 £원자중 1개 이상을포함하는헤테로고리기로이루어진군에서 선택된 1개 이상의 치환기로 치환또는비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, ”2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일수도있고, 2개의 페닐기가연결된 치환기로해석될수 있다. 본 명세서에서 카보닐기의 탄소수는특별히 한정되자 않으나, 탄소수 1내지 40인 것이 바람직하다. 구체적으로하기와같은구조의 화합물이 될수 있으나, 이에 한정되는것은아니다. 2019/139233 1»(:1^1{2018/013120
Figure imgf000006_0001
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로치환될수 있다. 구체적으로, 하기 구조식의 화합물이 될수 있으나, 이에 한정되는것은아니다.
4-In this specification, *-and ¾ each mean a bond connected to another substituent. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of 0 and £ atoms, or two or more substituents in the above-described substituents are substituted or unsubstituted. For example, the "substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may be interpreted as a substituent to which two phenyl groups are linked. In this specification, the carbon number of the carbonyl group is not particularly limited. , It is preferable to have 1 to 40 carbon atoms. Specifically, the compound may have the following structure, but is not limited thereto. 2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000006_0001
In the present specification, the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
Figure imgf000006_0002
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될수있으나, 이에 한정되는것은아니다.
Figure imgf000006_0002
In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, the compound may have the following structure, but is not limited thereto.
Figure imgf000006_0003
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기 , 1 부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기 , 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나이에 한정되지 않는다. 2019/139233 1»(:1^1{2018/013120
Figure imgf000006_0003
In the present specification, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, 1 butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited to this. 2019/139233 1 »(: 1 ^ 1 {2018/013120
본 명세서에 있어서 , 붕소기는 구체적으로 트리메틸붕소기 , 트리에틸붕소기, 1;-부틸디메틸붕소기 , 트리페닐붕소기 , 페닐붕소기 등이 있으나이에 한정되지 않는다. 본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가있다. 본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, 11_프로필, 이소프로필, 부틸, I:-부틸, 이소부틸, 라 부틸, -부틸, 1 -메틸-부틸, 1 -에틸-부틸, 펜틸, 11_펜틸, 이소펜틸, 네오펜틸, 호라卜팬틸, 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, 161寸-옥틸, 1 -메틸헵틸,In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, 1-butyldimethyl boron group, a triphenyl boron group, a 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. According to another 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 alkyl groups are methyl, ethyl, propyl, 11 _ propyl, isopropyl, butyl, I: tert-butyl, isobutyl, La-butyl, t-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, 11 _ Pentyl, isopentyl, neopentyl, horatinpanyl, nuclear chamber, 11 -nuclear chamber, 1 -methylpentyl, 2 -methylpentyl, 4 -methyl-2 -pentyl, 3,3-dimethylbutyl, 2 -ethylbutyl, heptyl, 11-heptyl, 1-methyl haeksil, cyclopentylmethyl, cyclohexyl haektil methyl, octyl, - octyl, 1 61寸-octyl, 1-methylheptyl,
2 -에틸핵실, 2 -프로필펜틸, 11-노닐, 2,2 -디메틸헵틸, 1 -에틸-프로필, 1, 1- 디메틸-프로필, 이소핵실, 2 -메틸펜틸, 4 -메틸핵실, 5 -메틸핵실 등이 있으나, 이들에 한정되지 않는다. 본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2내지 6이다. 구체적인 예로는 비닐, 1 -프로페닐, 이소프로페닐, 1 -부테닐, 2 -부테닐, 3 -부테닐, 1 -펜테닐,2-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 is not limited thereto. In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. 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 있으나이들에 2019/139233 1»(:1^1{2018/013120 2 -pentenyl, 3 -pentenyl, 3 -methyl- 1 -butenyl, 1,3-butadienyl, allyl, 1 -phenylvinyl 1- day, 2 -phenylvinyl-1 -day, 2,2 -Diphenylvinyl- 1-yl, 2-phenyl- 2- (naphthyl-l-yl) vinyl-l-yl, 2,2-bis (diphenyl-l-yl) vinyl-l-yl, stilbe But there's a nil group, styrenyl group, 2019/139233 1 »(: 1 ^ 1 {2018/013120
한정되지 않는다. 본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3내지 20이다. 또하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸 , 3 -메틸사이클로펜틸 , 2, 3 -디메틸사이클로펜틸, 사이클로핵실, 3 -메틸사이클로핵실, 4 -메틸사이클로핵실, 2,3- 디메틸사이클로핵실 , 3, 4, 5 -트리메틸사이클로핵실 , 4아61寸_부틸사이클로핵실 , 사이클로헵틸, 사이클로옥틸등이 있으나, 이에 한정되지 않는다. 본명세서에 있어서, 아릴기는특별히 한정되지 않으나탄소수 6내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는것은아니다. 본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로구조를 형성할수 있다. 상기 플루오레닐기가치환되는 경우, It is not limited. 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-trimethyl-bicyclo haeksil, 4 Ah 61寸_ butyl cycloalkyl include but haeksil, cycloheptyl, cyclooctyl, and the like. In the present specification, the aryl group is not particularly limited, but preferably 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, for example, a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
Figure imgf000008_0001
Figure imgf000008_0001
이 될수있다. 다만, 이에 한정되는것은아니다. 2019/139233 1»(:1^1{2018/013120 This can be However, it is not limited to this. 2019/139233 1 »(: 1 ^ 1 {2018/013120
본 명세서에 있어서, 헤테로고리기는 이종 원소로 0, 比 및 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기 , 트리아졸기, 아크리딜기, 피리다진기 , 피라지닐기, 퀴놀리닐기, 퀴나졸린기 , 퀴녹살리닐기, 프탈라지닐기 , 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀린기 , 인돌기, 카바졸기 , 벤조옥사졸기 , 벤조이미다졸기 , 벤조티아졸기 , 벤조카바졸기, 벤조티오펜기 , 디벤조티오펜기 , 벤조퓨라닐기,
Figure imgf000009_0001
In the present specification, the heterocyclic group is a heterocyclic group including one or more of 0, rain, and the like as a dissimilar element. Although the carbon number is not particularly limited, it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group 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, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group,
Figure imgf000009_0001
티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만한정되는것은아니다. 본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는전술한아릴기의 예시와같다. 본명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서 , 아릴텐은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서 , 헤테로아릴렌은 2가기인 것을 제외하고는 전술한헤테로고리기에 관한설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을제외하고는전술한아릴기 또는사이클로알킬기에 관한설명이 적용될수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한헤테로고리기에 관한설명이 적용될 수있다. 화학식 1로표시되는화합물 이하, 본 발명의 일 구현예에서 제공하는, 하기 화학식 1로 표시되는 2019/139233 1»(:1^1{2018/013120 Thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group, but are not limited to these. In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as 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 heterocyclic group. 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. In the present specification, except that the heteroarylene is a divalent group, the description of the aforementioned heterocyclic group may be applied. 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 heterocyclic ring is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding. Compound represented by Formula 1 Hereinafter, provided by one embodiment of the present invention, represented by the following Formula 1 2019/139233 1 »(: 1 ^ 1 {2018/013120
화합물을 상세히 설명한다. 단, 이하에서 상세히 설명되지 않은 치환기 등의 정의는, 전술한내용을참고하면 명확히 이해될 것이다: The compound is described in detail. However, definitions of substituents and the like which are not described in detail below will be clearly understood with reference to the above.
[화학식 1]  [Formula 1]
Figure imgf000010_0001
Figure imgf000010_0001
상기 화학식 1로 표시되는 화합물은, 헤테로 고리 화합물의 일종인 퀴놀린 ½1101比6)을 링커(니此라)로 하여 , 서로 동일하거나 상이한 2 개의 치환기가결합된구조를가지는것이다. The compound represented by the above formula (1), to the type of the heterocyclic compound quinoline ½ 0 1 11比比6) to the linker (Nishi此D), it will have the same or different two substituents are combined structure to each other.
여기서, 서로 동일하거나 상이한 2 개의 치환기는, ¾ 및 ¾로 정의하였다. 구체적으로,
Figure imgf000010_0002
및 ¾는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 것이되,
Figure imgf000010_0003
및 ¾ 중 적어도 하나는 하기 화학식 2으로 표시되는것이다. 단, ¾이화학식 2으로표시되며 人이 화학식 3으로표시되는 경우; 및 가화학식 2으로 표시되며 이 화학식 3으로 표시되는 경우를 제외한다.
Here, two substituents which are the same or different from each other are defined as ¾ and ¾. Specifically,
Figure imgf000010_0002
And ¾ are each independently represented by Formula 2 or 3,
Figure imgf000010_0003
And at least one of ¾ is represented by the following Chemical Formula 2. Provided that ¾ is represented by Formula 2 and 人 is represented by Formula 3; And it is represented by the formula (2) and except the case represented by the formula (3).
[화학식 2]  [Formula 2]
Figure imgf000010_0004
Figure imgf000010_0004
[화학식 3]  [Formula 3]
(匕 4 사3 상기 화학식 1로 표시되는 화합물은, 유기 발광 소자의 유기물 층의 재료로사용될 경우, 퀴놀린을 링커로 도입함으로써 전자끌개능력을 향상시켜 높은 전지·친화도를 가지게 하고 우수한 전자 전달 및 조절 능력을 가질 수 있다. 이에, 상기 화학식 1로표시되는화합물은, 유기 발광소자의 효율향상, 낮은구동전압및/또는수명 특성을향상시키는데 기여할수 있다. 2019/139233 1»(:1^1{2018/013120 ( 3 ) When the compound represented by the formula (1) is used as a material of the organic layer of the organic light emitting device, by introducing quinoline into the linker to improve the electron attracting ability to have a high battery, affinity and excellent electron transfer and Have the ability to regulate. Accordingly, the compound represented by Chemical Formula 1 may contribute to improving efficiency, low driving voltage and / or lifespan of the organic light emitting diode. 2019/139233 1 »(: 1 ^ 1 {2018/013120
구체적으로, 전술한화학식 1로 표시되는 화합물은, 11 및 ¾의 결합 위치에 따라, 하기 화학식 1-1 내지 1-21 중 어느 하나로 표시될 수 있다. 하기 화학식 1-1내지 1-21는각각, 내지 중 및 ¾를제외한나머지가 모두수소인 경우를예시한다: Specifically, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-21, depending on the bonding position of 11 and ¾. Formulas 1-1 to 1-21 illustrate the case where all the rest except hydrogen, to medium, and ¾ are hydrogen:
[화학식 1-1]  [Formula 1-1]
Figure imgf000011_0001
Figure imgf000011_0001
[화학식
Figure imgf000011_0002
[Formula
Figure imgf000011_0002
Figure imgf000011_0003
Figure imgf000011_0003
[화학식 1-7] 2019/139233 1»(:1^1{2018/013120 [Formula 1-7] 2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000012_0001
Figure imgf000012_0001
[화학식 1-14] 2019/139233 1»(:1^1{2018/013120 [Formula 1-14] 2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000013_0001
Figure imgf000013_0001
[화학식 1-21] 2019/139233 1»(:1^1{2018/013120 [Formula 1-21] 2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000014_0001
Figure imgf000014_0001
전술한 화학식 1로 표시되는 화합물이 상기 화학식 1-2로 표시되는 경우, 는상기 화학식 2로표시되고, 상기 화학식 ¾는상기 화학식 2또는 3으로표시된다.  When the compound represented by Chemical Formula 1 is represented by Chemical Formula 1-2, is represented by Chemical Formula 2, and Chemical Formula ¾ is represented by Chemical Formula 2 or 3.
이와독립적으로, 전술한화학식 1로 표시되는 화합물이 상기 화학식 Independently, the compound represented by Formula 1 described above is
1-4 로 표시되는 경우, 는 상기 화학식 2로 표시되고, 상기 화학식 ¾는 상기 화학식 2또는 3으로표시된다. When represented by 1-4, is represented by the formula (2), the formula ¾ is represented by the formula (2) or 3.
또한독립적으로, 전술한화학식 1로 표시되는화합물이 상기 화학식 1-1, 1-3, 및 1-5 내지 1-21로 표시되는 경우, 1' 및 ¾는 각각 독립적으로 상기 화학식 2또는 3으로표시되는 것이되, 1'및 12중 적어도하나는상기 화학식 2으로표시되는것이다. 한편, 이하의 설명은, 상기 화학식 1이 하기 화학식 1-1내지 1-21중 어느 하나로 표시되는지 여부와무관하게 적용되는 것이다. 또한, 이하의 각 설명은 독립적이며, 본 발명의 일 구현예의 구체적인 예시를 제시한 것일 뿐 이하의 설명에 의해본발명의 일구현예가제한되지 않는다. 상기 화학식 2에서, ¾, ¾ 및 ¾ 중 적어도 두 개는 일 수 있다: 구체적으로, ¾, ¾및 ¾가모두 일수있다. 상기 화학식 2 및 3에서, 내지 가 각각 독립적으로 결합 또는 페닐렌일수있다. 구체적으로, 상기 화학식 2에서 니는페닐렌일수 있다. ! 내지 紅3는 각각 독립적으로, 비치환되거나, 또는 01-4 알킬, 할로겐, 시아노, 및 트리( -4알킬)실릴로구성되는군으로부터 선택되는어느 하나의 치환기로 치환된 페닐; 비페닐릴; 터페닐릴; 쿼터페닐릴; 나프틸; 안트라세닐 ; 페난쓰레닐 ; 트리페닐레닐 ; 디메틸플루오레닐 ; 디페닐플루오레닐 ; 디벤조퓨라닐; 또는 디벤조티오페닐일 수 있다. 구체적으로, 12중 적어도하나가페닐기일수있다. \¥0 2019/139233 1»(:1^1{2018/013120 Independently, when the compound represented by Chemical Formula 1 is represented by Chemical Formulas 1-1, 1-3, and 1-5 to 1-21, 1 ′ and ¾ are each independently represented by Chemical Formula 2 or 3 Although it is represented, at least one of 1 'and 1 2 is represented by the formula (2). On the other hand, the following description, regardless of whether the formula 1 is represented by any one of the following formula 1-1 to 1-21. In addition, each of the following descriptions are independent, and merely presented specific examples of one embodiment of the present invention, and one embodiment of the present invention is not limited by the following description. In Formula 2, at least two of ¾, ¾, and ¾ may be: Specifically, ¾, ¾, and ¾ may be all. In Chemical Formulas 2 and 3, to may be each independently a bond or phenylene. Specifically, in Formula 2, ni may be phenylene. ! To 紅3 are each independently phenyl unsubstituted or substituted with any one substituent selected from the group consisting of 0 1-4 alkyl, halogen, cyano, and tri ( -4 alkyl) silyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethyl fluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl. Specifically, at least one of 1 and 2 may be a phenyl group. \ ¥ 0 2019/139233 1 »(: 1 ^ 1 {2018/013120
2!및 ¾중하나는상기 화학식 2으로표시되고, 나머지 하나는상기 화학식 3으로표시될수있다. 2 ! And ¾ may be represented by Formula 2, and the other may be represented by Formula 3.
5 보다구체적인 예를들어, 상기 화학식 1로표시되는화합물은하기로 구성되는군으로부터 선택되는어느하나일수있다. A specific example than 5, the compound represented by Formula 1 is any one selected from the number of days doeneungun configured to.
Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000018_0001
Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000018_0001
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
2019/139233 1»(:1/10公018/013120
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000036_0001
상기 화학식 1로 표시되는 화합물은. 하기 반응식 1과 같은 제조 방법으로제조할수 있다. 상기 제조방법은후술할제조예에서 보다구체화될 2019/139233 1»(:1^1{2018/013120
Figure imgf000036_0001
Compound represented by the formula (1). It can be prepared by the same method as in Scheme 1. The preparation method is more specific in the preparation examples to be described later. 2019/139233 1 »(: 1 ^ 1 {2018/013120
수있다. 상기 화학식 1로표시되는화합물을이용한유기 발광소자 Can be. Organic light emitting device using the compound represented by Formula 1
5 이하, 본 발명의 다른 일 구현예에서 제공하는, 유기 발광 소자를 상세히 설명한다. 이는, 상기 화학식 1로표시되는화합물을유기물층중 1층 이상에 포함하는 유기 발광 소자이며, 상가 화학식 1로 표시되는 화합물을 제외한 나머지 구성, 구조 등은 당 업계에 일반적으로 알려진 것과 동일한 것을적용한것일 있다. 5 or less, provided by another embodiment of the present invention will be described in detail an organic light emitting element. This is an organic light emitting device including the compound represented by Chemical Formula 1 in at least one layer of the organic layer, and the configurations, structures, and the like except for the compound represented by Chemical Formula 1 may be the same as those generally known in the art. have.
10  10
예를 들어, 본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 For example, 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, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
15 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을포함할수있다. 또한, 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을동시에 하는층을포함할수있고, 상기 정공주입층, 정공수송층, 또는 There is 15 . However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting the hole, the hole injection layer, the hole transport layer, or
20 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로표시되는화합물을포함한다. 20 A layer for simultaneously injecting and transporting a hole includes the compound represented by Chemical Formula 1. In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
2525
또한, 상기 유기물 층은 전자수송층, 또는 전자주입층을 포함할 수 있고, 상기 전자수송층, 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을포함한다.  In addition, the organic layer may include an electron transport layer or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).
30 또한, 상기 전자수송층 , 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는층은상기 화학식 1로표시되는화합물을포함한다. 또한, 상기 유기물 층은 발광층 및 전자수송층을 포함하고, 상기 전자수송층은상기 화학식 1로표시되는화합물을포함할수 있다. 또한, 본발명에 따른유기 발광소자는, 기판상에 양극, 1층이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일수 있다. 또한, 본발명에 따른유기 발광소자는기판상에 음극, 1층 이상의 유기물층및 양극이 순차적으로적층된 역방향구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대 , 본 발명의 일실시예에 따른 유기 발광 소자의 구조는도 1및 2에 예시되어 있다. 도 1은 기판 (1) , 양극 (2), 발광층 (3), 음극 (4)으로 이루어진 유기 발광소자의 예를도시한 것이다. 이와같은구조에 있어서, 상기 화학식 1로 표시되는화합물은상기 발광층에 포함될수 있다. 도 2는기판 (1) , 양극 (2), 정공주입층 (5), 정공수송층 (6), 발광층 (7), 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광소자의 예를도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 발광층및 전자수송층중 1층이상에 포함될수 있다. 본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로표시되는화합물을포함하는 것을 제외하고는당 기술분야에 알려져 있는 재료와방법으로 제조될 수 있다. 또한, 상기 유기 발광소자가 복수개의 유기물층을포함하는 경우, 상기 유기물층은동일한물질 또는다른 물질로형성될수있다. 예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제 1 전극, 유기물층 및 제 2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법 (sputter ing)이나 전자빔 증발법 (e-beam evaporat ion)과 같은 PVD(phys i cal Vapor Deposi t ion)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는금속산화물또는 이들의 합금을증착시켜 양극을 형성하고, 2019/139233 1»(:1^1{2018/013120 In addition, the electron transport layer, the electron injection layer, or the layer for the electron transport and the electron injection at the same time includes the compound represented by the formula (1). In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include 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 layers and a cathode are sequentially stacked on a substrate. The organic light emitting device according to the present invention may be an organic light emitting device having 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 device 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. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. 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 device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, metal or conductive metal oxides or alloys thereof on a substrate using a method of physical vapor deposition (PVD), such as sputtering or e-beam evaporat ion, To form an anode, 2019/139233 1 »(: 1 ^ 1 {2018/013120
그위에 정공주입층, 정공수송층, 발광층및 전자수송층을포함하는유기물 층을형성한후, 그위에 음극으로사용할수 있는물질을증착시켜 제조할수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을차례로증착시켜 유기 발광소자를만들수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공증착법 뿐만아니라용액 도포법에 의하여 유기물층으로형성될수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는것은아니다. 이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을차례로 증착시켜 유기 발광 소자를 제조할 수 있다 0 2003/012890) . 다만, 제조방법이 이에 한정되는것은아니다. 일례로, 상기 제 1 전극은 양극이고, 상기 제 2 전극은 음극이거나, 또는상기 제 1전극은음극이고, 상기 제 2전극은양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물 (110), 인듐아연 산화물 (1å0)과 같은 금속 산화물 ; ¾0:시 또는 3炯2 : ¾와 같은 금속과 산화물의 조합 ; 폴리 (3- 메틸티오펜), 폴리[3,4-(에틸렌- 1,2 -디옥시)티오펜] 묘的 , 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인둠, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; 니 ᆻ1 또는 Li¾Ml과같은다층구조물질등이 있으나, 이들에만한정되는것은아니다. 상기 정공주입층은 전극으로부터 정공을주입하는층으로, 정공주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 H0M0(highest occupi ed molecul ar orbi tal )가 양극물질의 일함수와주변 유기물증의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린 (porphyr in), 올리고티오펜, 아릴아민 계열의 유기물, 핵사니트릴핵사아자트리페닐렌 계열의 유기물, 퀴나크리돈 (quinacr idone)계열의 유기물, 페릴렌 (perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만한정 되는것은아니다. 상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을수송받아발광층으로옮겨줄수 있는물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만한정되는것은아니다. 상기 발광물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나인광에 대한양자효율이 좋은물질이 바람직하다. 구체적인 예로 8 - 히드록시-퀴놀린 알루미늄 착물 (Alq3) ; 카르바졸 계열 화합물; 이량체화 스티릴 (dimer ized styryl ) 화합물; BAlq; 10 -히드록시벤조 퀴놀린-금속 화합물 ; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물 ; 폴리 (p- 페닐렌비닐텐) (PPV) 계열의 고분자; 스피로 (spi ro) 화합물; 폴리플루오렌, 루브렌등이 있으나, 이들에만한정되는것은아니다. 2019/139233 1»(:1^1{2018/013120 After forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. 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 material 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 to these. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material 0 2003/012890). However, the manufacturing method is not limited to this. For example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is 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 110, indium zinc oxide 1a0; Combinations of metals and oxides, such as ¾0: hour or 3 炯2: ¾ ; 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; ᆻ 1 or Multilayer materials such as Li¾Ml, but not limited to them. 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, and is produced in the light emitting layer 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. It is preferable that H0M0 (highest occupied molecul ar orbital) of the hole injection material be between the work function of the anode material and the HOMO of the surrounding organic matter. Specific examples of the hole injection material include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but not limited to these. The hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer. A hole transporting material is a material capable of receiving holes from an anode or a hole injection layer and transferring the holes to the light emitting layer. Suitable. Specific examples include arylamine-based organics, conductive polymers, and block copolymers having both conjugated and non-conjugated portions, but are not limited thereto. 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. Concrete examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (p-phenylene vinylene) (PPV) family; Spi ro compounds; Polyfluorene, rubrene, etc., but not limited to these. 2019/139233 1 »(: 1 ^ 1 {2018/013120
상기 발광층은호스트재료및 도펀트재료를포함할수 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, 클루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란화합물, 피리미딘유도체등이 있으나, 이에 한정되지 않는다. 도펀트재료로는방향족아민유도체, 스트릴아민화합물, 붕소착체, 플루오란텐화합물, 금속착체 등이 있다. 구체적으로방향족아민유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기 , . 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다 . 구체적으로 스티릴아민, 스티릴디아민 , 스티릴트리아민, 스티릴테트라아민등이 있으나, 이에 한정되지 않는다. 또한, 금속착체로는이리듐착체, 백금착체 등이 있으나, 이에 한정되지 않는다. 상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로, 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8 -히드록시퀴놀린의 시 착물; 요1¾를포함한착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등아 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, 각경우알루미늄층또는실버층이 뒤따른다. 상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 2019/139233 1»(:1^1{2018/013120 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 gluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder type. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamino group, and a styrylamine compound is substituted or unsubstituted. A compound in which at least one arylvinyl group is substituted with a substituted arylamine, wherein the aryl group, 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, styryl amine, styryl diamine, styryl triamine, styryl tetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex and a platinum complex. The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable. Specific examples thereof include a complex of 8-hydroxyquinoline; Complexes containing urine 1 ¾ ; 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, each followed by an aluminum or silver layer. The electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, the effect of electron injection from the cathode, the light emitting layer or light emission 2019/139233 1 »(: 1 ^ 1 {2018/013120
재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논 , 안트라퀴노다이메탄, 다이페노퀴논 , 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. 상기 금속 착체 화합물로서는 8 -하이드록시퀴놀리나토 리륨, 비스(8- 하이드록시퀴놀리나토)아연, 비스(8 -하이드록시퀴놀리나토)구리, 비스(8- 하이드록시퀴놀리나토)망간, 트리스(8 -하이드록시퀴놀리나토)알루미늄, 트리스(2 -메틸- 8 -하이드록시퀴놀리나토)알루미늄 , 트리스(8- 하이드록시퀴놀리나토)갈륨, 비스(10 -하이드록시벤조 ¾]퀴놀리나토)베릴륨, 비스(10 -하이드록시벤조[비퀴놀리나토)아연, 비스(2 -메틸- 8- 퀴놀리나토)클로로갈륨, 비스(2 -메틸- 8 -퀴놀리나토)(0 -크레졸라토)갈륨, 비스( 2 -메틸- 8 -퀴놀리나토)( 1 -나프톨라토)알루미늄, 비스( 2 -메틸- 8- 퀴놀리나토)(2 -나프톨라토)갈륨등이 있으나, 이에 한정되지 않는다. 본발명에 따른유기 발광소자는사용되는재료에 따라전면 발광형 , 후면발광형 또는양면 발광형일수있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양전지 또는유기 트랜지스터에 포함될수 있다. 【발명의 실시를위한형태】 The compound which has the outstanding electron injection effect with respect to a material, prevents the movement of the excitons produced | generated in the light emitting layer to the hole injection 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 derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto. Examples of the metal complex compound include 8-hydroxyquinolinatolium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, Tris (2-methyl-8-hydroxyquinolinato) aluminum, Tris (8-hydroxyquinolinato) gallium , bis ( 10 -hydroxybenzo ¾] qui Nolinato) beryllium, bis (10-hydroxybenzo [biquinolinato] zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( 0- cresol Rato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, etc., are not limited to this. Do not. The organic light emitting device according to the present invention may be a front light emitting type, a back light emitting type or a double light emitting 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. [Form for implementation of the invention]
상기 화학식 1로표시되는화합물및 이를포함하는유기 발광소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을예시하기 위한것이며, 본발명의 범위가이들에 의하여 한정되는것이 아님은전술한바와같다. Preparation of the compound represented by 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 intended to illustrate the present invention, and the scope of the present invention is not limited by these as described above.
<제조예 1(화합물 1 21의 합성)> 2019/139233 1»(:1/10公018/013120 <Production Example 1 (Synthesis of Compound 1 21)> 2019/139233 1 »(: 1/10 公 018/013120
(1)화합물 1의 합성 (화학식 1-1) (1) Synthesis of Compound 1 (Formula 1-1)
Figure imgf000043_0001
1) 사 의 합성: 3 -브로모- 2 -히드록시퀴놀린 (30 133.8_01 ) , 트리페닐렌 -2 -일보로닉산 (38.2§, 140.5_01 ) 을 테트라하이드로퓨란 (30(加1 ) 에 첨가한 후 2 포타슘카보네이트 수용액 ( 150미1 )을 첨가하고, 테트라키스트리페닐-포스피노팔라듐 (3.09요, ¾101¾>)를 넣은 후, 10시간 동안 가열교반하였다. 상온으로 온도를 낮추고 반응을 종결한후 포타슘카보네이트 수용액을 제거하여 층분리하였다. 용매 제거 후 흰색의 고체를 에틸아세테이트로재결정하여 상기 01 ( 41.2
Figure imgf000043_0002
수율 83%)을제조하였다.
Figure imgf000043_0001
1) Synthesis: 3-bromo-2-hydroxyquinoline (30 133.8_01 ), triphenylene-2-ylboronic acid (38.2 § , 140.5_01 ) and tetrahydrofuran (30 (加 1) 2 potassium carbonate aqueous solution (150 US1 ) was added, followed by addition of tetrakistriphenyl-phosphinopalladium (3.09 yo, ¾ 101¾>) , followed by heating and stirring for 10 hours. The aqueous solution of potassium carbonate was removed and the layers were separated. After removing the solvent, the white solid was recrystallized from ethyl acetate to obtain 01 (41.2).
Figure imgf000043_0002
Yield 83%) was prepared.
아1\1대]+= 372.44 One to one] + = 372.44
2)쇼2의 합성: (25용, 67.1_01 )에 클로로포름 ( 400 )에 첨가하여 용해시킨 후 상온에서 퍼플루오로푸탄설포닐 플로라이드 (30.41§, 100. &^01 )을천천히 적가하고실온에서 3시간동안교반하였다. 상온에서 물과 此11 0™으로 추출한 후 흰색의 고체를 에틸아세테이트와 핵산으로 재결정하여 상기쇼2 (40.78용, 수율, 93%)을제조하였다. 2) Synthesis of 2 shows: (fluoride perfluoro Fu tanseol sulfonyl flow at room temperature was added and dissolved in chloroform (400), 67.1_ 01 for 25) (dropwise addition of 30.41 §, 100. & ^ 01) slowly, and Stir at room temperature for 3 hours. After extraction with water and 此 11 10 ™ at room temperature, the white solid was recrystallized with ethyl acetate and nucleic acid to prepare Show 2 (for 40.78, yield, 93%).
¾梅[¾1+비+= 654.52 2019/139233 1»(:1^1{2018/013120 ¾ 梅 [¾1 + ratio + = 654.52 2019/139233 1 »(: 1 ^ 1 {2018/013120
3) 쇼3 의 합성: 질소 분위기에서 상기 화합물 쇼2 (30용, 45.8_01), 비스(피나콜라토)다이보론(12.83§, 50.5_01) 및 아세트산칼륨 (13.2§, 137.4 ■01) 을섞고, 디옥산 (300 )룰 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스(디벤질리딘아세톤)팔라듐 (1.00당, 3미011)과 트리사이클로핵실포스핀(0.98 施01%)을 넣고 3시간 동안 가열,교반하였다. 반응 종료 후, 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고, 유기층을 무수황간마그네슘으로 건조하였다 . 감압 증류후테트라하이드로퓨란과에틸아세테이트로재결정하여 상기 쇼3 (18.072, 82%)를제조하였다. 3) Synthesis of 3 shows: The compounds show bis 2 (, for 45.8_01 30), in a nitrogen atmosphere (pinacolato) di boron (12.83 §, 50.5_ 01) and potassium acetate (13.2 §, 137.4 ■ 01) the Mix, add dioxane (300), and heat with stirring. In the state of reflux, bis (dibenzylideneacetone) palladium (per 1.00, 3 rice 01 1) and tricyclonuclear phosphine (0.98 s01 % ) were added thereto, followed by heating and stirring for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, extraction was performed with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was recrystallized from tetrahydrofuran and ethyl acetate to prepare the Show 3 (18.07 2, 82%).
[¾!+}!] += 482.40 [¾! +}!] + = 482.40
4) 화합물 1 의 합성: 쇼3 (2¾, 41.4_01), 2-(3 -클로로페닐)- 4,6- 디페닐- 1,3,5 -트리아진 (14.5요, 42.2_01) 을 테트라하이드로퓨란(300미1) 에 첨가한 후 21 포타슘카보네이트 수용액(150011)을 첨가하고, 테트라키스트리페닐-포스피노팔라듐(0.987요, ¾01%)를 넣은 후, 10시간 동안 가열교반하였다. 상온으로 온도를 낮추고 반응을 종결한후포타슘카보네이트 수용액을 제거하여 층분리하였다. 용매 제거 후 흰색의 고체를 에틸아세테이트로재결정하여 상기
Figure imgf000044_0001
수율 80%)을제조하였다.
4) Synthesis of Compound 1: Shows 3 (2¾, 41.4_ 01), 2- (3-triazine (14.5 I, 01 42.2_) - chlorophenyl) - 4,6-diphenyl-1,3,5 After addition to tetrahydrofuran (300 US1), 21 potassium carbonate aqueous solution (150 011 ) was added, and tetrakistriphenyl-phosphinopalladium (0.987 yo, ¾ 01% ) was added thereto, followed by heating and stirring for 10 hours. . After the temperature was lowered to room temperature and the reaction was terminated, the aqueous solution of potassium carbonate was removed and the layers were separated. After removing the solvent, the white solid was recrystallized from ethyl acetate.
Figure imgf000044_0001
Yield 80%) was prepared.
1내]+= 663.80 (2)화합물 2의 합성 (화학식 1-13) Within 1] + = 663.80 (2) Synthesis of Compound 2 (Formula 1-13)
2019/139233 1»(:1/10公018/013120 2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000045_0001
Figure imgf000045_0001
1)바의 합성: 상기요1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 6 -브로모- 4 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2, 4 -디페닐- 6-1) Synthesis of bar: 6-bromo-4-hydroxyquinoline in place of 3-bromo-2-hydroxyquinoline in the synthesis of I-1, 2,4-di instead of triphenylene-2-ilboronic acid Phenyl-6-
5 (4-(4,4,5, 5 -테트라메틸- 1,3, 2 -디옥사보로레인- 2 -일)페닐) 1,3, 5 -트리아진을 사용한것을제외하고는동일한방법으로합성하여 을제조하였다 5 (4- (4,4,5,5-tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl) synthesis by the same method, except that 1,3,5-triazine is used. Manufactured
3 대]+= 453.52 3 units] + = 453.52
2) 32 의 합성: 상기 요2 의 합성에서 사 대신 을 사용한 것을 제외하고는동일한방법으로합성하여 62을제조하였다  2) Synthesis of 32: 62 was prepared by synthesizing in the same manner, except that in the synthesis of Y2, instead of yarn was used.
10 3 +}{]+= 735.60 10 3 +} {] + = 735.60
3) 63 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 묘2을 사용한 것을 제외하고는동일한방법으로합성하여 63을제조하였다  3) Synthesis of 63: In the synthesis of Show 3, 63 was prepared in the same manner except that seedling 2 was used instead of Show 2.
¾^[¾1태]+= 563.48 ¾ ^ [¾1 state] + = 563.48
4) 화합물 2의 합성: 상기 화합물 1의 합성에서 쇼3대신 83룰, 2- 4) Synthesis of Compound 2: 83-Lule, 2-instead of Show 3, in the synthesis of Compound 1
15 (3 -클로로페닐)- 4,6 -디페닐- 1,3, 5 -트리아진 대신 4-(4 -클로로페닐)- 2,6_ 디페닐피리미딘을사용한것을제외하고는동일한방법으로합성하여 화합물 2 을제조하였다 \¥0 2019/139233 (그1/10公018/013120 Synthesis was carried out in the same manner, except that 4- (4-chlorophenyl) -2,6_diphenylpyrimidine was used instead of 15 (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Compound 2 was prepared \ ¥ 0 2019/139233 (1/10 公 018/013120
[¾! += 743.89 [¾! + = 743.89
Figure imgf000046_0001
Figure imgf000046_0001
1) 01의 합성 : 상기 의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 6 -브로모- 3-히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산대신 [1,1’ -비페닐]_ 4 -일보로닉산을 사용한 것을 제외하고는 동일한 방법으로 합성하여 01 을 제조하였다1) Synthesis of 01: 6-bromo-3-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline in the above synthesis, [1,1′-rather than triphenylene-2-ylboronic acid; Synthesis was carried out in the same manner, except that phenyl] _ 4 -ylboronic acid was used, thereby preparing 01.
1«+비+ :: 298.36 1 «+ rain + :: 298.36
2) 02 의 합성: 상기 쇼2 의 합성에서 사 대신 다을 사용한 것을 제외하고는동일한방법으로합성하여 02을제조하였다  2) Synthesis of 02: Synthesis of 02 was carried out in the same manner as in Synthesis of Show 2 except that Da was used instead of Sa.
¾6[¾}대]+= 580.44 ¾6 [¾}] + = 580.44
3) 03 의 합성: 상기 쇼3 의 합성에서 요2 대신 02을 사용한 것을 제외하고는동일한방법으로합성하여 03을제조하였다  3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 02 was used instead of Yo2.
別 [11+11] += 408.32 11 [11 + 11] + = 408.32
4) 화합물 3의 합성 : 상기 화합물 1의 합성에서 쇼3대신 03를, 2 - 4) Synthesis of Compound 3: In the synthesis of Compound 1, 03 was substituted instead of Show 3,
(3 -클로로페닐)- 4,6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 -클로로페닐)- 4,6- 디페닐- 1,3,5 -트리아진 을사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 3을제조하였다(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the synthesis in the same manner to prepare compound 3
3[1«+비+= 589.71 2019/139233 1»(:1/10公018/013120 3 [1 «+ ratio + = 589.71 2019/139233 1 »(: 1/10 公 018/013120
(4)화합물 4의 합성 (화학식 1-7) (4) Synthesis of Compound 4 (Formula 1-7)
Figure imgf000047_0001
Figure imgf000047_0001
1) 1)1의 합성 : 상기요1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 3 -브로모- 4 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2,4 -디페닐- 6-1) Synthesis of 1) 1: 3 -bromo-4 -hydroxyquinoline instead of 3 -bromo-2 -hydroxyquinoline in the synthesis of I-1, 2,4 instead of triphenylene-2 -ilboronic acid -Diphenyl-6-
(4-(4,4, 5, 5 -테트라메틸- 1,3,2 -디옥사보로레인- 2 -일)페닐) 1,3,5 -트리아진을 사용한것을제외하고는동일한방법으로합성하여 1)1을제조하였다(4- (4,4,5,5-Tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl) Synthesis in the same manner except using 1,3,5-triazine 1) 1 was manufactured
]\1+}{]+= 453.52 ] \ 1 +} {] + = 453.52
2) 02 의 합성: 상기 쇼2 의 합성에서 대신 이을 사용한 것을 제외하고는동일한방법으로합성하여 02을제조하였다  2) Synthesis of 02: Synthesis of 02 was carried out in the same manner, except that Synthesis of Show 2 was used instead.
13[¾1내]+= 735.60 13 [in ¾1] + = 735.60
3) 03 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 2을 사용한 것을 제외하고는동일한방법으로합성하여 03을제조하였다 3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 2 was used instead of Show 2.
아 +비 563.48  Oh + rain 563.48
4) 화합물 4의 합성: 상기 화합물 1의 합성에서 쇼3대신 03를, 2 - 4) Synthesis of Compound 4: In the synthesis of Compound 1, 03 instead of Show 3, 2 −
(3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 4’ -브로모- [1, 1’ -비페닐]- 4 -카보나이트릴을사용한것을제외하고는동일한방법으로합성하여 화합물 4 을제조하였다 The same method except using 4'-bromo- [1,1'-biphenyl] -4-carbonitrile instead of (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 4 was prepared by synthesizing with.
1아1\1+11]+= 614.72 2019/139233 1»(:1/10公018/013120 1 child1 \ 1 + 11] + = 614.72 2019/139233 1 »(: 1/10 公 018/013120
(5)화합물 5의 합성 (화학식 1-14) (5) Synthesis of Compound 5 (Formula 1-14)
Figure imgf000048_0001
1) 의 합성: 상기 쇼1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 7 -브로모- 4 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 4,6-디페닐-2_
Figure imgf000048_0001
1) Synthesis: 7-bromo-4-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline and 4,6-diphenyl instead of triphenylene-2-ylboronic acid in the synthesis of Show 1 -2_
(4-(4, 4,5, 5 -테트라메틸- 1 , 3, 2 -디옥사보로레인- 2 -일 )페닐)피리미딘을 사용한 것을제외하고는동일한방법으로합성하여 을제조하였다 Except for using (4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-2-yl) phenyl) pyrimidine, the synthesis was carried out in the same manner to prepare.
¾[引; ¾!+¾+= 452.53 ¾ [引; ¾! + ¾ + = 452.53
2) 묘2 의 합성: 상기 쇼2 의 합성에서 사 대신 을 사용한 것을 제외하고는동일한방법으로합성하여 £2을제조하였다  2) Synthesis of Grave 2: In the synthesis of Show 2, £ 2 was produced in the same way, except that instead of 4 was used.
¾犯[¾!+}!] += 734.61 ¾ 犯 [¾! +}!] + = 734.61
3) 묘3 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 표2을 사용한 것을 제외하고는동일한방법으로합성하여 £3을제조하였다  3) Synthesis of Mystery 3: Synthesis of £ 3 was made in the same manner, except that Table 2 was used instead of Show2 in the synthesis of Show3.
¾犯[!«+}!] += 562.49 ¾ 犯 [! «+}!] + = 562.49
4) 화합물 5의 합성: 상기 화합물 1의 합성에서 요3대신 £3를 , 2- (3 -클로로페닐)- 4 ,6 -디페닐- 1,3 ,5 -트리아진 대신 2-(4 -클로로페닐)- 4,6- 디페닐- 1,3, 5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 5을제조하였다 4) Synthesis of Compound 5: £ 3 instead of 3 in the synthesis of Compound 1, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the synthesis of the compound 5 in the same manner
¾1 ¾«1]+= 743.89 ¾1 ¾ «1] + = 743.89
(6)화합물 6의 합성 (화학식 1-15) (6) Synthesis of Compound 6 (Formula 1-15)
Figure imgf000049_0001
Figure imgf000049_0001
1) 1 의 합성 : 상기 /\1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 8 -브로모- 4 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 (4-1) Synthesis of 1: Instead of 3-bromo-2-hydroxyquinoline in the synthesis of / \ 1, 8-bromo-4-hydroxyquinoline was substituted for triphenylene-2-ylboronic acid (4-
(디벤조 [ 利푸란- 4 -일)페닐)보로닉산을 사용한 것을 제외하고는 동일한 방법으로합성하여
Figure imgf000049_0002
제조하였다
Synthesis was carried out in the same manner, except that (dibenzo [lipuran-4-yl) phenyl) boronic acid was used.
Figure imgf000049_0002
Manufactured
[¾!+!!] += 388.44 2)
Figure imgf000049_0003
의 합성: 상기 쇼2 의 합성에서 사 대신 比을 사용한 것을 제외하고는동일한방법으로합성하여 묘2을제조하였다 2019/139233 1»(:1/10公018/013120 +비 670.52
[¾! + !!] + = 388.44 2)
Figure imgf000049_0003
Synthesis of Seed 2 was prepared in the same manner as in Exhibit 2, except that instead of 4 was used. 2019/139233 1 »(: 1/10 公 018/013120 + rain 670.52
3)
Figure imgf000050_0001
의 합성: 상기 쇼3 의 합성에서 쇼2 대신 F2을 사용한 것을 제외하고는동일한방법으로합성하여 3을제조하였다
3)
Figure imgf000050_0001
Synthesis of: Synthesis of Show 3 was carried out in the same manner as in Synthesis of Show 3 except that F 2 was used instead of Show 2.
¾13¾+11]+= 498.40 ¾13¾ + 11] + = 498.40
4) 화합물 6의 합성 : 상기 화합물 1의 합성에서 쇼3대신 3룰, 2 - 4) Synthesis of Compound 6: In the synthesis of Compound 1, 3 rule instead of Show 3, 2-
(3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 -클로로페닐)- 4-(3-chlorophenyl) -4,6-diphenyl- 1,2- (4-chlorophenyl) instead of 1,3,5-triazine
(나프탈렌 -2 -일)- 6 -페닐- 1,3 ,5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로합성하여 화합물 6을제조하였다 Compound 6 was prepared in the same manner except for using (naphthalene-2-yl) -6-phenyl-1,3,5-triazine.
¾13 +비+= 729.86 ¾13 + ratio + = 729.86
Figure imgf000050_0002
Figure imgf000050_0002
1)아의 합성 : 상기요1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 7 -브로모- 8 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 (4-(애_카바졸_ 9 -일)페닐)보로닉산을 사용한 것을 제외하고는 동일한 방법으로 합성하여 따 을제조하였다 1) Synthesis of A: In the synthesis of I-1, 7-bromo-8-hydroxyquinoline is substituted for 3-bromo-2-hydroxyquinoline, and triphenylene-2-ilboronic acid is used instead of (4- Carbazol _ 9 -yl) phenyl) Boronic acid was synthesized in the same manner, except that it was prepared.
¾^[¾!+비+= 387.45 2019/139233 1»(:1^1{2018/013120 ¾ ^ [¾! + Ratio + = 387.45 2019/139233 1 »(: 1 ^ 1 {2018/013120
2) 02 의 합성: 상기 쇼2 의 합성에서 사 대신 아을 사용한 것을 제외하고는동일한방법으로합성하여 G2을제조하였다2) Synthesis of 02: Synthesis of G2 was carried out in the same manner as in Synthesis of Show 2 except that A was used instead of S.
3[1\1내]+= 669.53 3 [in 1 \ 1] + = 669.53
3) 03 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 02을 사용한 것을 제외하고는동일한방법으로합성하여 03을제조하였다  3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 02 was used instead of Show 2.
¾6[¾1+비+= 497.42 ¾6 [¾1 + ratio + = 497.42
4) 화합물 7의 합성 : 상기 화합물 1의 합성에서 쇼3대신 3를, 2 - 4) Synthesis of Compound 7: 3, instead of show 3 in the synthesis of Compound 1, 2 −
(3 -클로로페닐)- 4,6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 -클로로페닐)- 4-(3-chlorophenyl) -4,6-diphenyl 2-, 4-chlorophenyl instead of 1,3,5-triazine
(나프탈렌 -1 -일)- 6 -페닐- 1,3, 5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로합성하여 화합물 7을제조하였다Compound 7 was prepared in the same manner except for using (naphthalene-1-yl) -6-phenyl-1,3,5-triazine.
3[¾1+비+= 728.87 3 [¾1 + ratio + = 728.87
(8)화할물 8의 합성 (화학식 1-18(8) Synthesis of Compound 8 (Formula 1-1 8 )
2019/139233 1»(:1/10公018/013120 2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000052_0001
Figure imgf000052_0001
1) 의 합성:상기 의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 8 -브로모- 5 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 4’ -(4, 4,5,5- 테트라메틸- 1,3, 2 -디옥사보로레인- 2 -일)- [1,1’ -디페닐]- 4 -카보니트릴을 사용한것을제외하고는동일한방법으로합성하여 을제조하였다  1) Synthesis: 8-bromo-5-hydroxyquinoline in place of 3-bromo-2-hydroxyquinoline in the synthesis of 4 '-(4, 4, instead of triphenylene-2-ylboronic acid 5,5-Tetramethyl-l, 3,2-dioxabolorane-2-yl)-[1,1'-diphenyl] -4-carbonitrile was synthesized in the same manner, except that it was prepared.
1마¾1+비+= 323.37 1 Ma ¾1 + ratio + = 323.37
2) 112 의 합성: 상기 쇼2 의 합성에서 사 대신 따을 사용한 것을 제외하고는동일한방법으로합성하여 112을제조하였다  2) Synthesis of 112: In the synthesis of Show 2, 112 was synthesized in the same manner except for using Ta instead of Sa.
1아¾1+}1]+ :: 605.45 1 child¾1 +} 1] + :: 605.45
3) 113 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 112을 사용한 것을 제외하고는동일한방법으로합성하여 을제조하였다 3) Synthesis of 113: In the synthesis of Show 3, 112 was used instead of Show 2. Except for the synthesis in the same way to manufacture
[¾!+¾+= 433.33 [¾! + ¾ + = 433.33
4) 화합물 8의 합성 : 상기 화합물 1의 합성에서 쇼3대신 113를, 2 - (3 -클로로페닐)- 4, 6 -디페닐- 1,3 ,5 -트리아잔 대신 2,4 -디페닐- 6-(4-(4,4,5,5_ 테트라메틸- 1,3,2 -디옥사보로레인- 2 -일)페닐) 1,3,5 -트리아진 을 사용한 것을 제외하고는동일한방법으로합성하여 화합물 8제조하였다 4) Synthesis of Compound 8: In the synthesis of Compound 1, 113 instead of Show 3 and 2,4-diphenyl instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazane. -6- (4- (4,4,5,5_tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl) 1,3,5-triazine in the same manner except Compound 8 was prepared by synthesis.
아 +비 614.72  Oh + rain 614.72
Figure imgf000053_0001
Figure imgf000053_0001
1)11 의 합성: 상기 사 의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 2 -클로로- 6 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산대신 9-(4-(4 -페닐- 6- (4-(4,4,5,5 -테트라메틸- l,3,2-디옥사보로레인-2-일)페닐)l,3,5-트리아진-2- 일)페닐)抑-카바졸을사용한것을제외하고는동일한방법으로합성하여 II을 제조하였다 2019/139233 1»(:1^1{2018/013120 아¾1+비+= 618.71 1) Synthesis of 11: In the synthesis of the above compound, 2-chloro-6-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline, and 9- (4- (4) instead of triphenylene-2-ylboronic acid. -Phenyl-6- (4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-2-yl) phenyl) l, 3,5-triazin-2-yl) II was prepared in the same manner except for using phenyl) 페닐 -carbazole. 2019/139233 1 »(: 1 ^ 1 {2018/013120 A¾1 + ratio + = 618.71
2) 12 의 합성: 상기 쇼2 의 합성에서 쇼1 대신 I I을 사용한 것을 제외하고는동일한방법으로합성하여 12을제조하였다  2) Synthesis of 12: In the synthesis of Show 2, 12 was prepared by synthesizing in the same manner except that I I was used instead of Show 1.
¾保[¾1내]+= 900.79 ¾ 保 [in ¾1] + = 900.79
3) 화합물 9의 합성 : 상기 화합물 1의 합성에서 쇼3대신 13를, 2- (3 -클로로페닐)- 4,6 -디페닐- 1,3,5 -트리아진 대신 페닐보로닉산을 사용한 것을 제외하고는동일한방법으로합성하여 화합물 9제조하였다  3) Synthesis of Compound 9: In the synthesis of Compound 1, 13 was used instead of Show 3, and phenylboronic acid instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Compound 9 was prepared in the same manner except for preparing compound 9
1 1\1+¾+= 678.81 1 1 \ 1 + ¾ + = 678.81
(10)화합물 10의 합성 (화학식 1-6) (10) Synthesis of Compound 10 (Formula 1-6)
Figure imgf000054_0001
Figure imgf000054_0001
1) II의 합성: 상기 쇼1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 8 -클로로- 2 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2,4 -디페닐- 6- (4-(4, 4, 5,5 -테트라메틸- 1, 3,2 -디옥사보로레인- 2 -일)페닐) 1,3,5 -트리아진을 사용한것을제외하고는동일한방법으로합성하여 II을제조하였다 1) Synthesis of II: In the synthesis of Show 1, 8-chloro-2-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline, and 2,4-diphenyl instead of triphenylene-2-ylboronic acid 6- (4- (4, 4, 5,5-Tetramethyl-l, 3,2-dioxabolorane-2-yl) phenyl) except for using 1,3,5-triazine Was synthesized to prepare II.
13 내]+= 453.52 Within 13] + = 453.52
2) 12 의 합성: 상기 요2 의 합성에서 대신 을 사용한 것을 2019/139233 1»(:1/10公018/013120 제외하고는동일한방법으로합성하여 12을제조하였다 2) Synthesis of 12: using instead of in the synthesis of 2019/139233 1 »(: 1/10 公 018/013120 Except for 1/10
¾!£ [¾!+}!] += 735.60 ¾! £ [¾! +}!] + = 735.60
3) ]3 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 犯을 사용한 것을 제외하고는동일한방법으로합성하여 13을제조하였다  3) Synthesis of] 3 Synthesis of 13 was carried out in the same manner as in Synthesis of Show 3, except that 犯 was used instead of Show 2.
¾13¾+11]+= 563.48 ¾13¾ + 11] + = 563.48
10) 화합물 10 의 합성 : 상기 화합물 1의 합성에서 쇼3 대신 13룰, 2-(3 -클로로페닐)- 4,6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 -클로로페닐)- 4,6- 디페닐- 1,3, 5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 10제조하였다. 10) Synthesis of Compound 10: In the synthesis of Compound 1, 13 (L) instead of Show 3, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-chloro) Phenyl) -4,6-diphenyl-1,3,5-triazine was synthesized in the same manner to prepare compound 10.
3[¾1+비+= 744.87 3 [¾1 + ratio + = 744.87
(11)화합물 11의 합성 (화학식 1-2) (11) Synthesis of Compound 11 (Formula 1-2)
Figure imgf000055_0001
2019/139233 1»(:1/10公018/013120
Figure imgf000055_0001
2019/139233 1 »(: 1/10 公 018/013120
1) XI의 합성: 상기요1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신1) Synthesis of XI: Instead of 3-bromo-2-hydroxyquinoline in the synthesis of I-1
2 -클로로- 4 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2-([1.1’ - 비페닐]- 3 -일)- 4 -페닐- 6-( 4 , 4 , 5, 5 -테트라메틸- 1, 3, 2 -디옥사보로레인- 2 -일)_ 1,3, 5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 을 제조하였다2- (chloro-)-hydroxyquinoline was replaced with 2-([1.1'-biphenyl] -3-yl)-4-phenyl-6- (4, 4, 5, instead of triphenylene-2-ylboronic acid. 5-tetramethyl-1,3,2-dioxabolorane-2-yl) _ 1,3,5-triazine was synthesized in the same manner except that
3 대]+= 529.62 3 units] + = 529.62
2) 의 합성: 상기 쇼2 의 합성에서 대신 1(1을 사용한 것을 제외하고는동일한방법으로합성하여 1(2을제조하였다  2) Synthesis: In the synthesis of Show 2, 1 (2) was prepared by synthesizing in the same manner except that 1 (1) was used instead.
13_]+= 811.69 13_] + = 811.69
3) 화합물 11의 합성 : 상기 화합물 1의 합성에서쇼3대신또2를, 2- (3 -클로로페닐)- 4, 6 -디페닐- 1, 3, 5 -트리아진 대신 비페닐- 4 -보로닉산을 사용한 것을제외하고는동일한방법으로합성하여 화합물 11제조하였다  3) Synthesis of Compound 11: In the synthesis of Compound 1, biphenyl-4 instead of show 3 instead of 2-, 3- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. A compound 11 was prepared by the same method except for using boronic acid.
¾ 3[¾1대]+= 665.81 ¾ 3 [¾1] + = 665.81
(12)화합물 12의 합성 (화학식 1-3) (12) Synthesis of Compound 12 (Formula 1-3)
Figure imgf000056_0001
Figure imgf000056_0001
1) 1그의 합성: 상기 의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 2 -클로로- 5 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2,4 -디페닐- 6- (3-4, 4, 5 , 5 -테트라메틸- 1 , 3 , 2 -디옥사보로레인- 2 -일)페닐)- 1 , 3 , 5 -트리아진을 사용한것을제외하고는동일한방법으로합성하여 1그을제조하였다 1) 1 Synthesis: 2-Chloro-5-hydroxyquinoline in place of 3-bromo-2-hydroxyquinoline in the above synthesis, 2,4-diphenyl-6 in place of triphenylene-2-ylboronic acid -(3-4, 4, 5, 5--tetramethyl-l, 3,2-dioxabolorane-2-yl) phenyl)-1,3,5-triazine Except for the use, it was synthesized in the same way and manufactured.
1 ¾1+11]+= 453.52 1 ¾1 + 11] + = 453.52
2) 12 의 합성: 상기 쇼2 의 합성에서 사 대신 1그을 사용한 것을 제외하고는동일한방법으로합성하여 1^2을제조하였다  2) Synthesis of 12: In the synthesis of Show 2, 1 ^ 2 was prepared by synthesizing in the same manner except that 1 instead of 4 was used.
¾6[¾1+11]+= 735.60 ¾6 [¾1 + 11] + = 735.60
3) 화합물 12의 합성 : 상기 화합물 1의 합성에서요3대신 12를, 2 - 3) Synthesis of Compound 12 In the synthesis of Compound 1, 12 instead of 3, 2 −
(3 -클로로페닐)- 4,6 -디페닐- 1,3,5 -트리아진 대신 . 3-(班!-카바졸- 9- 일)페닐)보로닉산을사용한것을제외하고는동일한방법으로합성하여 화합물 12를제조하였다 (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead . Compound 12 was prepared in the same manner except for using 3- (VII! -Carbazol-9-yl) phenyl) boronic acid, to prepare Compound 12.
¾1와1\«{]+= 678.81 ¾1 and 1 \ «{] + = 678.81
Figure imgf000057_0001
1) 의 합성: 상기 사의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신
Figure imgf000057_0001
1) Synthesis: Instead of 3-bromo-2-hydroxyquinoline in the synthesis of the above
2 -브로모- 7 -클로로퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 (4’ -시아노-2 -bromo-7 -chloroquinoline instead of triphenylene-2-ylboronic acid (4'-cyano-
[1,1’ -비페닐]- 4 -일)보로닉산을 사용한 것을 제외하고는 동일한 방법으로 Except that [1,1′-biphenyl] -4-yl) boronic acid was used.
Figure imgf000057_0002
2019/139233 1»(:1/10公018/013120
Figure imgf000057_0002
2019/139233 1 »(: 1/10 公 018/013120
3) 화합물 13의 합성 : 상기 화합물 1의 합성에서쇼3대신 ¾12를 , 2- (3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 -클로로페닐)- 4,6- 디페닐- 1,3, 5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 13를제조하였다 3) Synthesis of Compound 13: In the synthesis of Compound 1, ¾12 instead of Show 3 was substituted with 2- (4-chloro instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Phenyl) -4,6-diphenyl-1,3,5-triazine was synthesized in the same manner to prepare compound 13
Figure imgf000058_0001
Figure imgf000058_0001
1) 의 합성 : 상기 사의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 3 -브로모- 5 -클로로퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2-([1,1’ - 비페닐]- 4 -일)- 4 -페닐- 6-(4-(4, 4 , 5, 5 -테트라메틸- 1, 3, 2 -디옥사보로레인- 2- 일)페닐)- 1,3, 5 -트리아진을사용한것을제외하고는동일한방법으로합성하여 을제조하였다 1) Synthesis: 3-bromo-5-chloroquinoline in place of 3-bromo-2-hydroxyquinoline in the synthesis of the above compound, 2-([1,1'-) in place of triphenylene-2-ylboronic acid Biphenyl]-4-yl)-4-phenyl-6- (4- (4, 4, 5, 5--tetramethyl- 1, 3, 2- dioxaborolane- 2-yl) phenyl) -1, Except for the use of 3,5-triazines, they were synthesized in the same manner to produce.
MS[M+H]+= 390.88 MS [M + H] + = 390.88
2) 2 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 附을 사용한 것을 제외하고는동일한방법으로합성하여 2를제조하였다 2019/139233 1»(:1/10公018/013120
Figure imgf000059_0001
482.40
2) Synthesis of 2: Synthesis of 2 was carried out in the same manner as in the synthesis of Show 3, except that 附 was used instead of Show 2. 2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000059_0001
482.40
3)화합물 14의 합성 : 상기 화합물 1의 합성에서쇼3대신 N2룰, 2 - (3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2 -브로모트리페닐텐을사용한 것을제외하고는동일한방법으로합성하여 화합물 14를제조하였다  3) Synthesis of Compound 14: In the synthesis of Compound 1, 2-bromotriphenyl instead of N 2 rule, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of Show 3 Compound 14 was prepared in the same manner, except that ten was used.
Figure imgf000059_0002
Figure imgf000059_0002
상기 화합물 1 의 합성에서 쇼3 대신 3 -브로모- 7 -퀴놀린을, 2-(3- 클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2,4-디페닐-6-(3-4,4,5,5_ 테트라메틸- 1,3,2 -디옥사보로레인- 2 -일)페닐)- 1,3,5 -트리아진을 사용한 것을 제외하고는동일한방법으로합성하여 화합물 15를제조하였다  In the synthesis of Compound 1, 3-bromo-7-quinoline is substituted for show 3, and 2,4-diphenyl is substituted for 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. -6- (3-4,4,5,5_tetramethyl-1,3,2-dioxabolorane-2-yl) phenyl)-1,3,5-triazines in the same manner except Compound 15 was prepared by synthesis.
13 +비+ 744.87 (16)화합물 16의 합성 (화학식 1-11) 13 + ratio + 744.87 (16) Synthesis of Compound 16 (Formula 1-11)
Figure imgf000060_0001
Figure imgf000060_0001
1) 01의 합성 1) Synthesis of 01
상기 사 의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 3 -브로모- 8- 클로로퀴놀린을, 트라페닐렌 -2 -일보로닉산 대신 (4-(나프탈렌 -1- 일)페닐)보로닉산을사용한 것을 제외하고는동일한 방법으로 합성하여 01을 제조하였다  In the synthesis of the above, 3-bromo-8-chloroquinoline instead of 3-bromo-2-hydroxyquinoline and (4- (naphthalen-1-yl) phenyl) borotrane instead of traphenylene-2-ylboronic acid 01 was prepared by synthesizing in the same manner except for using nic acid.
1마¾1+비+= 366.86 1 Ma ¾1 + Ratio + = 366.86
2) 02의 합성  2) Synthesis of 02
상기 요3 의 합성에서 요2 대신 01을 사용한 것을 제외하고는 동일한 방법으로합성하여 02를제조하였다 Synthesis of 02 was carried out in the same manner, except that 01 was used instead of 2- in the synthesis of Ya-3.
아 +비 458.37  Oh + rain 458.37
3)화합물 16의 합성 : 상기 화합물 1의 합성에서쇼3대신 02를, 2 - 3) Synthesis of Compound 16: In place of Show 3 in the synthesis of Compound 1, 02, 2-
(3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2-(4 -클로로페닐)- 4,6- 디페닐- 1 ,3, 5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 16를제조하였다 (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Compound 16 was prepared by the same method except in the same manner.
¾^[¾1대]+= 739.89 ¾ ^ [¾1] + = 739.89
(17)화합물 17의 합성 (화학식 1-12) 2019/139233 1»(:1/10公018/013120 (17) Synthesis of Compound 17 (Formula 1-12) 2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000061_0001
Figure imgf000061_0001
3 -브로모- 8 -클로로퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2, 4 -디페닐- 6-(4- (4,4, 5, 5 -테트라메틸- 1,3,2 -디옥사보로레인- 2 -일)페닐) 1,3, 5 -트리아진을 사용한것을제외하고는동일한방법으로합성하여아을제조하였다3-bromo-8-chloroquinoline was replaced by 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2) instead of triphenylene-2-ylboronic acid. Dioxaborolane 2-yl) phenyl) 1,3, 5- Triazine was synthesized in the same manner except that triazine was used to produce a child.
+비 471.96  + R 471.96
2) ?2 의 합성: 상기 ^3 의 합성에서 쇼2 대신 라을 사용한 것을 제외하고는동일한방법으로합성하여 2를제조하였다 2) Synthesis of? 2: In the synthesis of ^ 3, 2 was synthesized in the same manner except that Ra was used instead of Show 2.
3[¾1내]+= 563.48 3 [in 1⁄3] + = 563.48
3) 화합물 17의 합성 : 상기 화합물 1의 합성에서쇼3대신 2룰, 2 - 3) Synthesis of Compound 17: In the synthesis of Compound 1, 2ruL, 2-instead of Show 3
(3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 4-(4 -클로로페닐)- 2,6- 디페닐피리미딘을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 17를제조하였다 Synthesis in the same manner, except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine was used instead of (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Compound 17 was prepared
財 []¾+¾+= 743.89 財 [] ¾ + ¾ + = 743.89
(18)화합물 18의 합성 (화학식 1-16) 2019/139233 1»(:1/10公018/013120 (18) Synthesis of Compound 18 (Formula 1-16) 2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000062_0001
Figure imgf000062_0001
1) ¾1의 합성 : 상기 쇼1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 5 -클로로- 6 -히드록시퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2, 4 -디페닐- 6- (3-4,4,5, 5 -테트라메틸- 1,3,2 -디옥사보로레인- 2 -일)페닐)- 1,3, 5 -트리아진을 사용한것을제외하고는동일한방법으로합성하여아을제조하였다1) Synthesis of ¾1: 5 -Chloro-6-hydroxyquinoline instead of 3-bromo-2-hydroxyquinoline in the synthesis of Show 1, 2,4-diphenyl instead of triphenylene-2-ylboronic acid 6- (3-4,4,5,5-Tetramethyl-l, 3,2-dioxabolorane-2-yl) phenyl)-except for using 1,3,5-triazine Synthesized with
3¾+비+= 453.52 3¾ + ratio + = 453.52
2) 02 의 합성: 상기 요2 의 합성에서 대신 아을 사용한 것을 제외하고는동일한방법으로합성하여 02를제조하였다 2) Synthesis of 02: Synthesis of 02 was carried out in the same manner as in Example 2 except that Ah was used instead to prepare 02.
3¾대]+= 735.60 3¾ units] + = 735.60
3) 03 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 02을 사용한 것을 제외하고는동일한방법으로합성하여 03을제조하였다  3) Synthesis of 03: Synthesis of 03 was carried out in the same manner as in Synthesis of Show 3, except that 02 was used instead of Show 2.
¾保[¾!+¾+= 563.48 ¾ 保 [¾! + ¾ + = 563.48
3) 화합물 18의 합성 :상기 화합물 1의 합성에서쇼3대신 03를 , 2- (3 -클로로페닐)- 4 ,6 -디페닐- 1,3, 5 -트리아진 대신 3 -브로모비페닐을 사용한 것을제외하고는동일한방법으로합성하여 화합물 18을제조하였다 2019/139233 1»(:1/10公018/013120 3) Synthesis of Compound 18: In the synthesis of Compound 1, 03 instead of Show 3, 3- (bromobiphenyl) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the use, compounds 18 were prepared in the same manner. 2019/139233 1 »(: 1/10 公 018/013120
MS[M+H]+= 589.71 MS [M + H] + = 589.71
(19)화합물 19의 합성 (화학식 1-17) (19) Synthesis of Compound 19 (Formula 1-17)
Figure imgf000063_0001
Figure imgf000063_0001
1)財의 합성 : 상가쇼1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 5 -브로모- 7 -히드록시퀴놀린을, 트리페닐렌 -2 -알보로닉산 대신 4,6-디페닐-2_ (3-(4, 4,5, 5 -테트라메틸- 1, 3 , 2 -디옥사보로레인- 2 -일 )페닐)피리미딘을 사용한 것을제외하고는동일한방법으로합성하여 을제조하였다1) Synthesis: 5 -bromo-7 -hydroxyquinoline instead of 3 -bromo-2 -hydroxyquinoline in the synthesis of Sangasho 1, 4,6-di instead of triphenylene-2 -alboronic acid Except for using phenyl-2_ (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) phenyl) pyrimidine, the synthesis was carried out in the same manner to prepare.
3[¾1+비+= 452.52 3 [¾1 + ratio + = 452.52
2) 1?2 의 합성: 상기 쇼2 의 합성에서 사 대신 을 사용한 것을 제외하고는동일한방법으로합성하여묘2를제조하였다  2) Synthesis of 1 ~ 2: In the synthesis of Show 2, seedling 2 was prepared by synthesizing in the same manner except that instead of yarn was used.
[¾!+¾+= 734.61 () 2019/139233 1»(그1/10公018/013120 (¾! + ¾ + = 734.61 () 2019/139233 1 »(1/10 公 018/013120
3) 요3 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 묘2을 사용한 것을 제외하고는동일한방법으로합성하여묘3를제조하였다 3) Synthesis of Key 3: In the synthesis of Show 3, seedling 3 was prepared in the same manner except that seedling 2 was used instead of show 2.
¾^[¾1+¾+= 562.49 ¾ ^ [¾1 + ¾ + = 562.49
4) 화합물 19의 합성 : 상기 화합물 1의 합성에서쇼3대신묘3를, 2- (3 -클로로페닐)- 4,6 -디페닐- 1,3, 5 -트리아진 대신 2-(2 -클로로페닐)- 4,6- 디페닐- 1,3,5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 19을제조하였다 4) Synthesis of Compound 19: In the synthesis of Compound 1, Compound 3 instead of Show 3 was substituted with 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. Chlorophenyl) -4,6-diphenyl-1,3,5-triazine was synthesized in the same manner to prepare Compound 19.
3¾+비+= 743.89 3¾ + ratio + = 743.89
(20)화합물 20의 합성 (화학식 1-19) (20) Synthesis of Compound 20 (Formula 1-19)
Figure imgf000064_0001
Figure imgf000064_0001
1) 의 합성 : 상기 쇼1의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 6 -브로모- 7 -클로로퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2, 4 -디페닐- 6-(4- (4,4,5,5 -테트라메틸- 1,3,2 -디옥사보로레인- 2 -일)페닐)피리미딘을사용한 것을 제외하고는동일한방법으로합성하여 을제조하였다 2019/139233 1»(:1/10公018/013120 1) Synthesis: 6-bromo-7-chloroquinoline instead of 3-bromo-2-hydroxyquinoline in the synthesis of Show 1, 2,4-diphenyl- instead of triphenylene-2-ylboronic acid Synthesis was carried out in the same manner, except that 6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) phenyl) pyrimidine was used to prepare. 2019/139233 1 »(: 1/10 公 018/013120
1아1\1+비+= 470.97 1 child 1 + 1 ratio + = 470.97
2) 松 의 합성: 상기 쇼3의 합성에서 쇼2 대신 을 사용한 것을 제외하고는동일한방법으로합성하여 役을제조하였다 2) Synthesis of 松: In the synthesis of Show 3, except that Show 2 was used instead, it was synthesized in the same manner to prepare 役.
+비 562.49  + R 562.49
3)화합물 20의 합성 : 상기 화합물 1의 합성에서 요3대신 2를 , 2- 3) Synthesis of Compound 20: In the synthesis of Compound 1, 2 instead of 3, 2-
(3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2-(3 -클로로페닐)- 4,6- 디페닐- 1,3 ,5 -트리아진을 사용한 것을 제외하고는 동일한 방법으로 합성하여 화합물 20를제조하였다(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for the synthesis in the same manner to prepare Compound 20
3[¾1대]+= 743.89 3 [¾1] + = 743.89
Figure imgf000065_0001
Figure imgf000065_0001
1) II의 합성 : 상기 의 합성에서 3 -브로모- 2 -히드록시퀴놀린 대신 6 -브로모- 8 -클로로퀴놀린을, 트리페닐렌 -2 -일보로닉산 대신 2-([1,1’ - 비페닐]- 4 -일)- 4 -페닐- 6-(4-(4,4,5,5 -테트라메틸- 1,3,2 -디옥사보로레인- 2- 일)페닐- 1,3,5 -트리아진을사용한 것을 제외하고는 동일한 방법으로 합성하여 II을제조하였다 1) Synthesis of II: In the above synthesis, 6-bromo-8-chloroquinoline instead of 3-bromo-2-hydroxyquinoline and 2-([1,1 '] instead of triphenylene-2-ylboronic acid. -Biphenyl] -4 -yl) -4 -phenyl- 6- (4- (4,4,5,5 -tetramethyl- 1,3,2 -dioxaborolane-2 -yl) phenyl- 1, II was prepared by the same method except that 3,5-triazine was used.
MS[M+H]+= 548.06 MS [M + H] + = 548.06
2) 72 의 합성: 상기 쇼3 의 합성에서 쇼2 대신 끄을 사용한 것을 2019/139233 1»(:1^1{2018/013120 2) Synthesis of 72: In the above Synthesis of Show 3, it was used instead of Show 2 2019/139233 1 »(: 1 ^ 1 {2018/013120
제외하고는동일한방법으로합성하여 12를제조하였다12 were manufactured in the same way except for the synthesis.
301+1!]+= 639.58 301 + 1!] + = 639.58
3)화합물 21의 합성 : 상기 화합물 1의 합성에서쇼3대신 12룰, 2 - (3 -클로로페닐)- 4, 6 -디페닐- 1,3, 5 -트리아진 대신 2 -브로모트리페닐렌을사용한 것을제외하고는동일한방법으로합성하여 화합물 21를제조하였다  3) Synthesis of Compound 21: In the synthesis of Compound 1, 2-bromotriphenyl instead of 12 rule, 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of show 3 Compound 21 was prepared in the same manner except for the use of len.
¾¾[¾1대]+= 739.89 ¾¾ [¾1] + = 739.89
<실시예 1> <Example 1>
11X3(인듐 주석 산화물)가 1,000ᅀ 두께로 박막 코팅된 유리 기판((:01' 11용 7059 크 을, 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 3(土라 ¾ .의 제품을사용하였으며, 증류수는附11 아6 00. 제품의 필터( 라)로 2차 걸러진 증류수를 사용하였다. 0를 30분간 세척한후, 증류수로 2회 반복하여 초음파세척을 10분간진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고건조시켰다. 11X3 (Indium Tin Oxide) thin film is a glass substrate coated with ((1,000 ᅀ thickness: Put 01 7059 11 For greater, it was dissolved in distilled water, a dispersant and washed with ultrasonic waves. Detergent was used as the 3 (土la ¾. Of product, distilled water was used as the secondary distilled water and filtered by filter附11 O 6 0 0. products (D). After washing 0 for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried.
이렇게 준비된 110 투명 전극 위에 핵사니트릴 핵사아자트리페닐기렌
Figure imgf000066_0001
111-1)를 500요의 두께로열 진공증착하여 정공주입층을형성하였다. 그위에 정공을수송하는 물질인 1111 (900ᅀ)을 진공증착한 후 이어서 상기 정공 수송층 위에 } 2 을 막두께 50ᅀ으로 진공증착하여 정공조절층을 형성하였다. 화합물 발광층으로 호스트볘1과 도판트 301 화합물(25: 1) 을 300入의 두께로 진공 증착하였다. 그 다음에 E^:m 화합물(50ᅀ)을 전자조절층으로 형성시키고 제조예 1 에서 합성한화합물
Figure imgf000066_0002
310入)로공증착시켜 전자수송층으로순차적으로 형성하였다. 상기 전자 수송증 위에 순차적으로 10요 두께의 리꼼 플루오라이드(니 와 ¾¾와 쇼용 (10: 1, 150入) 증착하고 1,000ᅀ 두께의
Nuclear nitrile nucleated azatriphenylgirene on the 110 transparent electrode thus prepared
Figure imgf000066_0001
111-1) was vacuum-deposited to a thickness of 500 yaw to form a hole injection layer. Thereafter, 1111 (900 kPa), a material for transporting holes, was vacuum deposited, followed by vacuum deposition of # 2 at a film thickness of 50 kPa on the hole transport layer to form a hole control layer. Host # 1 and the dopant 301 compound (25: 1) were vacuum-deposited at the thickness of 300 pieces with the compound light emitting layer. Then, an E ^: m compound (50 kV) was formed as an electron control layer and the compound synthesized in Preparation Example 1
Figure imgf000066_0002
310 sets) was sequentially formed into an electron transport layer. 10 μm thick Rimium fluoride (Niwa ¾¾ and Shawyong (10: 1, 150 入) was deposited on the electron transport bottle and 1,000 ᅀ thick.
_ 알루미늄을증착하여 음극을형성하여 , 유기 발광소자를제조하였다. An organic light-emitting device was manufactured by depositing aluminum to form a cathode.
상기의 과정에서 유기물의 증착속도는 1 떼를 유지하였고, 리륨플루라이드는 0.2 入八%, 알루미늄은 3 ~ 7 人八 의 증착속도를 유지하였다.
Figure imgf000067_0001
2019/139233 1»(그1^1{2018/013120
In the above process, the deposition rate of the organic material was maintained at 1 flock, the lithium fluoride was 0.2 入 八%, and the aluminum was maintained at the deposition rate of 3-7 phosphorus.
Figure imgf000067_0001
2019/139233 1 »(1 ^ 1 {2018/013120
<실시예 2> <Example 2>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 4 를 사용한것을제외하고는동일하게실험하였다. <실시예 3>  Except for using the compound 4 instead of compound 2 in the electron transport layer in Example 1 was the same experiment. <Example 3>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 5 를 사용한것을제외하고는동일하게 실험하였다.  Except for using Compound 5 instead of Compound 2 as the electron transport layer in Example 1 was the same experiment.
<실시예 4> <Example 4>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 7 를 사용한것을제외하고는동일하게 실험하였다.  Except for using the compound 7 instead of compound 2 as the electron transport layer in Example 1 was the same experiment.
<실시예 5> Example 5
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 8 를 사용한것을제외하고 동일하게 실험하였다.  Except for using compound 8 instead of compound 2 as the electron transport layer in Example 1 was the same experiment.
<실시예 6> <Example 6>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 10 를 사용한것을제외하고는동일하게실험하였다.  Except for using the compound 10 instead of compound 2 in the Example 1 electron transport layer was the same experiment.
<실시예 7> <Example 7>
상기 실시예 1에서 전자 수송증으로 화합물 2 대신 화합물 11 를 사용한것을제외하고는동일하게실험하였다. <실시예 8>  Except for using the compound 11 instead of compound 2 in the electron transport in Example 1 was the same experiment. <Example 8>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 13 를 사용한것을제외하고는동일하게 실험하였다.  Except for using the compound 13 instead of compound 2 in the electron transport layer in Example 1 and was the same experiment.
<실시예 9> Example 9
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 15 를 사용한것을제외하고는동일하게실험하였다. 2019/139233 1»(:1^1{2018/013120 Except for using Compound 15 instead of Compound 2 as the electron transport layer in Example 1 was the same experiment. 2019/139233 1 »(: 1 ^ 1 {2018/013120
<실시에 10> <Embodiment 10>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 19 를 사용한것을제외하고는동일하게 실험하였다.  Except for using Compound 19 instead of Compound 2 in the electron transport layer in Example 1 and was the same experiment.
<실시예 11> <Example 11>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 20 를 사용한것을제외하고는동일하게 실험하였다. <실시예 12>  Except for using Compound 20 instead of Compound 2 in the electron transport layer in Example 1 and was the same experiment. <Example 12>
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 7 를 사용하고, 화합물 7 과 니£1 와의 비율을 1: 1 대신 2: 1 로 사용한 것을 제외하고는동일하게실험하였다. <실시예 13>  Except for using the compound 7 instead of compound 2 in Example 1, and the ratio of the compound 7 and ni £ 1 1: 1 instead of 1: 1 was the same experiment. Example 13
상기 실시예 1에서 전자 수송층으로 화합물 2 대신 화합물 13 를 사용하고, 화합물 13 과 110 와의 비율을 1: 1 대신 1:2 로 사용한 것을 제외하고는동일하게실험하였다.  Except for using compound 13 instead of compound 2 in Example 1, and the ratio of the compound 13 and 110 and 1: 1 instead of 1: 1 was the same experiment.
<실시예 14> <Example 14>
상기 실시예 1에서 전자 수송증으로 화합물 2 대신 화합물 20 를 사용하고, 화합물 20 과 니요 와의 비율을 1: 1 대신 2: 1 로 사용한 것을 제외하고는동일하게실험하였다. <비교예 1>  Except for using compound 20 instead of compound 2 in Example 1, and the ratio of compound 20 and niyo was 2: 1 instead of 1: 1 was the same experiment. Comparative Example 1
상기 실시예 1에서 전자수송증을화합물 2 대신 £11을사용한것을 제외하고는동일하게실험하였다.  In Example 1, the electron transport certificate was tested in the same manner except that £ 11 was used instead of Compound 2.
<비교예 2> Comparative Example 2
상기 실시예 1에서 전자수송층을화합물 2대신 £ 2을사용한것을 제외하고는동일하게실험하였다. 2019/139233 1»(:1^1{2018/013120 In Example 1, the electron transport layer was tested in the same manner except that £ 2 was used instead of Compound 2. 2019/139233 1 »(: 1 ^ 1 {2018/013120
<비교예 3> <Comparative Example 3>
상기 실시예 1에서 전자 수송층을 화합물 2 대신 £12 를 사용하고, 전자 수송층과 110 의 비율을 1: 1 대신 2: 1 로 사용한 것을 제외하고는 동일하게실험하였다.  In Example 1, the electron transport layer was tested in the same manner except that £ 12 was used instead of Compound 2, and the ratio of the electron transport layer and 110 was 2: 1 instead of 1: 1.
<비: 5己^! 4> <Rain: 5 己 ^! 4>
상기 실시예 1에서 전자 수송층을 화합물 2 대신 £ 2 를 사용하고,
Figure imgf000070_0001
In Example 1, the electron transporting layer used £ 2 instead of Compound 2.
Figure imgf000070_0001
동일하게실험하였다.  The same experiment was carried out.
<비교예 5> <Comparative Example 5>
상기 실시예 1에서 전자수송층을화합물 2대신 하기 5 5를사용한  In Example 1, the electron transport layer was used instead of the compound 5 5 5
Figure imgf000070_0002
Figure imgf000070_0002
牌6 2019/139233 1»(:1^1{2018/013120 牌 6 2019/139233 1 »(: 1 ^ 1 {2018/013120
<실험예 1> Experimental Example 1
상기 실시예 1 ~ 14 및 비교예 1 ~ 6 과 같이 각각의 화합물을 전자 수송층 물질로 사용하여 제조한 유기 발광 소자를 실험한 결과를 표 1 에 나타내었다.  Table 1 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the electron transporting material as in Examples 1 to 14 and Comparative Examples 1 to 6.
[표 1] TABLE 1
Figure imgf000071_0001
실시예 15 ñ
Figure imgf000071_0001
Example 15
IT0 (인듐 주석 산화물)가 1,000 A 두께로 박막 코팅된 유리 기판 (corning 7059 glass)을, 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fi scher Co.의 제품을사용하였으며, 증류수는 Mi l l ipore Co. 제품의 필터 (Fi lter)로 2차 걸러진 증류수를 사용하였다. IT0를 30분간 세척한후, 증류수로 2회 반복하여 초음파세척을 10분간진행하였다. 증류수 세척이 끝난후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고건조시켰다.  A glass substrate (corning 7059 glass) coated with a thin film of ITO (Indium Tin Oxide) having a thickness of 1,000 A was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. The detergent used was Fischer Co.'s product. Secondly filtered distilled water was used as a product filter. After washing IT0 for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol, and dried.
이렇게 준비된 IT0 투명 전극 위에 핵사니트릴 핵사아자트리페닐기렌 (hexani tr i le hexaazat r i phenyl ene , HI-1)를 500A의 두께로열 진공증착하여 정공주입층을형성하였다. 그위에 정공을수송하는 물질인 HT1 (900 A )을 진공증착한 후 이어서 상기 정공 수송층 위에 HT2 을 막두께 50 A으로 진공증착하여 정공조절층을 형성하였다. 화합물 발광층으로 호스트 BH1과 도판트 BD1 화합물 (25: 1) 을 300A의 두께로 진공 증착하였다. 그 다음에 제조예 1 에서 합성한 화합물 1 (50A)을 전자조절층으로 형성시키고 ETM2 와 LiQ (1: 1, 310 A)로 공증착시켜 전자수송층으로 순차적으로 형성하였다. 상기 전자수송층위에 순차적으로 10 A 두께의 리튬 플루오라이드 (LiF)와 Mg와 Ag (10: 1, 150 A) 증착하고 1,000A 두께의 알루미늄을증착하여 음극을형성하여, 유기 발광소자를제조하였다.  On the thus prepared IT0 transparent electrode, nucleonitrile nuxaazatriphenylgirene (hexanitrile hexaazat riphenylphenyl, HI-1) was thermally vacuum deposited to a thickness of 500 A to form a hole injection layer. HT1 (900 A), which is a material for transporting holes, was vacuum deposited thereon, followed by vacuum deposition of HT2 with a film thickness of 50 A on the hole transport layer to form a hole control layer. The host BH1 and the dopant BD1 compound (25: 1) were vacuum deposited to a thickness of 300 A as the compound light emitting layer. Then, Compound 1 (50A) synthesized in Preparation Example 1 was formed as an electron control layer and co-deposited with ETM2 and LiQ (1: 1, 310 A) to form an electron transport layer sequentially. Lithium fluoride (LiF), Mg and Ag (10: 1, 150 A) having a thickness of 10 A was sequentially deposited on the electron transport layer, and a cathode was formed by depositing aluminum having a thickness of 1,000 A, thereby manufacturing an organic light emitting device. .
상기의 과정에서 유기물의 증착속도는 1 A/sec를 유지하였고, 리륨플루라이드는 0.2 A/sec, 알루미늄은 3 ~ 7 A/sec의 증착속도를 유지하였다. In the above process, the deposition rate of the organic material was maintained at 1 A / sec, the lithium fluoride was maintained at 0.2 A / sec, and the aluminum was maintained at a deposition rate of 3 to 7 A / sec.
Figure imgf000073_0001
2019/139233 1»(:1^1{2018/013120
Figure imgf000073_0001
2019/139233 1 »(: 1 ^ 1 {2018/013120
<실시예 1於 <Example 1 '
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 3 을 사용한것을제외하고는동일하게실험하였다. <실시예 17>  Except for using Compound 3 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment. <Example 17>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 6 을 사용한것을제외하고는동일하게실험하였다.  Except for using the compound 6 instead of compound 1 in the electron control layer in Example 15 was the same experiment.
<실시예 18> <Example 18>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 7 을 사용한것을제외하고는동일하게실험하였다.  Except for using compound 7 instead of compound 1 in the electron control layer in Example 15 and was the same experiment.
<실시예 19> <Example 19>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 9 을 사용한것을제외하고는동일하게실험하였다.  Except for using the compound 9 instead of compound 1 as the electron control layer in Example 15 was the same experiment.
<실시예 20> <Example 20>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 10을 사용한것을제외하고는동일하게 실험하였다.  Except for using the compound 10 instead of compound 1 as the electron control layer in Example 15 was the same experiment.
<실시예 21> <Example 21>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 11을 사용한것을제외하고는동일하게 실험하였다. <실시예 22>  Except for using compound 11 instead of compound 1 in the electron control layer in Example 15 and was the same experiment. <Example 22>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 12를 사용한것을제외하고는동일하게 실험하였다.  Except for using Compound 12 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.
<실시예 23> <Example 23>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 14를 사용한것을제외하고는동일하게실험하였다. 2019/139233 1»(:1^1{2018/013120 Except for using Compound 14 instead of Compound 1 as the electron control layer in Example 15 was the same experiment. 2019/139233 1 »(: 1 ^ 1 {2018/013120
<실시예 24> <Example 24>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 16 을 사용한것을제외하고는동일하게 실험하였다.  Except for using Compound 16 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.
<실시예 25> <Example 25>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 17 을 사용한것을제외하고는동일하게 실험하였다.  Except for using Compound 17 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.
10 <실시예 26> 10 <Example 26>
상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 18 을 사용한것을제외하고는동일하게 실험하였다.  Except for using Compound 18 instead of Compound 1 as the electron control layer in Example 15 and was the same experiment.
<실시예 27> Example 27
15 상기 실시예 15 에서 전자 조절층으로 화합물 1 대신 화합물 21 을 사용한것을제외하고는동일하게 실험하였다. 15 The same experiment as in Example 15 except for using the compound 21 instead of compound 1 as the electron control layer.
<실시예 28> <Example 28>
상기 실시예 1에서 전자조절층을화합물 1대신 화합물 6을사용하고,
Figure imgf000075_0001
In Example 1, the electron control layer was used in place of Compound 1 Compound 6,
Figure imgf000075_0001
제외하고는동일하게실험하였다.  Except for the same experiment.
<실시예 29> <Example 29>
상기 실시예 1에서 전자조절층을화합물 1대신 화합물 12을사용하고,
Figure imgf000075_0002
In Example 1, the electron control layer was used in place of Compound 1 Compound 12,
Figure imgf000075_0002
제외하고는동일하게실험하였다.  Except for the same experiment.
<실시예 30> <Example 30>
상기 실시예 1에서 전자조절층을화합물 1대신 화합물 17을사용하고,
Figure imgf000075_0003
In Example 1, the electron control layer was used in place of compound 1 compound 17,
Figure imgf000075_0003
제외하고는동일하게실험하였다. 2019/139233 1»(:1^1{2018/013120 Except for the same experiment. 2019/139233 1 »(: 1 ^ 1 {2018/013120
<비교예 7> Comparative Example 7
상기 실시예 7에서 전자조절층으로화합물 1대신 £13을사용한것을 제외하고는동일하게실험하였다.  The same experiment was conducted in Example 7, except that £ 13 instead of 1 was used as the electron adjusting layer.
<비교예 8> <Comparative Example 8>
상기 실시예 7에서 전자조절층으로화합물 1대신 £ 4을사용한것을 제외하고는동일하게실험하였다. <비교예 9>  The same experiment was conducted in Example 7, except that £ 4 instead of 1 was used as the electron adjusting layer. Comparative Example 9
상기 실시예 7에서 전자 조절층으로 화합물 1 대신 £ 4을 사용하고, 전자 수송층과 느山 의 비율을 1: 1 대신 2: 1 로 사용한 것을 제외하고는 동일하게 실험하였다. <비교예 10>  Except for using compound 4 in Example 7 instead of compound 1 in Example 7, and the ratio of the electron transport layer and Nesan 2: 1 instead of 1: 1 was the same experiment. Comparative Example 10
상기 실시예 7에서 전자 조절층으로 화합물 1 대신 묘13을 사용하고, 전자 수송층과 니0 의 비율을 1: 1 대신 1:2 로 사용한 것을 제외하고는 동일하게실험하였다. <비교예 11>  Except for using the compound 13 in Example 7 instead of compound 1 in Example 7, and the same experiment except that the ratio of the electron transport layer and the ni 0 in 1: 2 instead of 1: 1. Comparative Example 11
상기 실시예 7에서 전자조절층을화합물 1 대신 7를사용한것을 제외하고는동일하게실험하였다.  In Example 7, the electron control layer was tested in the same manner except that 7 was used instead of Compound 1.
Figure imgf000076_0001
Figure imgf000076_0001
牌7 2019/139233 1»(:1^1{2018/013120 牌 7 2019/139233 1 »(: 1 ^ 1 {2018/013120
<비교예 12> Comparative Example 12
상기 실시예 7에서 전자조절층을화합물 1 대신 £18를사용한것을 제외하고는동일하게실험하였다.  In Example 7, the electron control layer was tested in the same manner except that £ 18 was used instead of Compound 1.
Figure imgf000077_0001
Figure imgf000077_0001
<실험예 2>  Experimental Example 2
상기 실시예 15 - 30및 비교예 7 11과같이 각각의 화합물을 전자 수송층 물질로 사용하여 제조한 유기 발광 소자를 실험한 결과를 표 2 에 나타내었다.  Table 2 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the electron transporting material as in Examples 15-30 and Comparative Example 7 11.
[표 2] TABLE 2
Figure imgf000077_0002
2019/139233 1»(:1^1{2018/013120
Figure imgf000077_0002
2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000078_0001
Figure imgf000078_0001
본 발명에 따른 화학식의 화합물 유도체는 유기 발광 소자를 비롯한 유기 전자소자에서 전자수송및 전자조절 역할을할수 있으며, 본발명에 따른소자는효율, 구동전압, 안정성 면에서 우수한특성을나타낸다. Compound derivative of formula according to the invention, is able to control the electron transport and electron role in an organic electronic device including an organic light emitting element, the element according to the invention represents the efficiency, driving voltage, excellent properties in terms of stability.
【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: 발광층 8: 전자수송층  7: light emitting layer 8: electron transport layer

Claims

2019/139233 1»(:1^1{2018/013120  2019/139233 1 »(: 1 ^ 1 {2018/013120
【청구의 범위】 [Range of request]
【청구항 11  [Claim 11
하기 화학식 1로표시되는화합물: Compound represented by the following formula ( 1 ):
[화학식 1]  [Formula 1]
Figure imgf000079_0001
Figure imgf000079_0001
상기 화학식 1에서,  In Chemical Formula 1,
¥1내지 '1중어느하나는 ¾이고,¥ 1 to '1 of which is ¾,
1내지 71을제외한나머지에서 어느하나는 2이고, 내지 7중 ¾및 2를제외한나머지는각각,수소이고 1 to 7 in all but one of which one is 2, and to 7, each of which except the ¾ and 2, the hydrogen
및 ¾는 각각 독립적으로 하기 화학식 2 또는 3으로 표시되는 것이되, 및 ¾중적어도하나는하기 화학식 2으로표시되는것이며,  And ¾ are each independently represented by the following Chemical Formula 2 or 3, and at least one of ¾ is represented by the following Chemical Formula 2,
(단, 九이 화학식 2으로 표시되며 이 화학식 3으로 표시되는 경우; 및 가화학식 2으로표시되며 이 화학식 3으로표시되는경우를제외함) [화학식 到  (Wherein 九 is represented by the formula (2) and represented by the formula (3); And (2) except for the case represented by Formula (2) and represented by Formula (3).
Figure imgf000079_0002
이되, ¾내지 ¾중 적어도 하나는
Figure imgf000079_0002
At least one of ¾ to ¾
내지 는 각각 독립적으로, 결합; 또는 치환또는 비치환된 06-60 아릴텐이고, 2019/139233 1»(:1^1{2018/013120 Or each independently, a bond; Or substituted or unsubstituted 0 6-60 arylten , 2019/139233 1 »(: 1 ^ 1 {2018/013120
쇼 내지 3는 각각 독립적으로, 치환 또는 비치환된 06-60 아릴기; 또는 치환 또는 비치환된 0, 比 및 £ 중 1개 이상을 포함하는 02-60 헤테로아릴기이며, Show to 3 each independently represent a substituted or unsubstituted 0 6-60 aryl group; Or a 0 2-60 heteroaryl group containing one or more of 0, 比 and £ substituted or unsubstituted,
I),
Figure imgf000080_0001
I·, 및 3는각각독립적으로, 0내지 3의 정수이다.
I) ,
Figure imgf000080_0001
I, and 3 are each independently an integer of 0 to 3.
【청구항 2] [Claim 2]
제 1항에 있어서,  The method of claim 1,
상기 화학식 1이 하기 화학식 1-1내지 1-21중어느하나로표시되는 것인, Formula 1 is represented by any one of the following formula 1-1 to 1-21,
화합물:  compound:
[화학식 1-1]  [Formula 1-1]
Figure imgf000080_0002
2019/139233 1»(:1^1{2018/013120
Figure imgf000080_0002
2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000081_0001
Figure imgf000081_0001
[화학식 1-13] 2019/139233 1»(:1^1{2018/013120 [Formula 1-13] 2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000082_0001
Figure imgf000082_0001
[화학식 1-20] 2019/139233 1»(:1^1{2018/013120
Figure imgf000083_0001
[Formula 1-20] 2019/139233 1 »(: 1 ^ 1 {2018/013120
Figure imgf000083_0001
[화학식 1-21]
Figure imgf000083_0002
[Formula 1-21]
Figure imgf000083_0002
상기 화학식 1-2에서,  In Chemical Formula 1-2,
¾는 상기 화학식 2로 표시되고, 상기 화학식 ¾는 상기 화학식 2 또는 3으로표시되며,  ¾ is represented by Formula 2, wherein ¾ is represented by Formula 2 or 3,
상기 화학식 1-4에서,  In Chemical Formula 1-4,
는 상기 화학식 2로 표시되고, 상기 화학식 ¾는 상기 화학식 2 또는 3으로표시되며,  Is represented by Formula 2, wherein Formula ¾ is represented by Formula 2 or 3,
상기 화학식 1-1, 1-3, 및 1-5내지 1-21에서 ,  In Chemical Formulas 1-1, 1-3, and 1-5 to 1-21,
1' 및 ¾는 각각 독립적으로 상기 화학식 2 또는 3으로 표시되는 것이되, 및 ¾중적어도하나는상기 화학식 2으로표시되는것이다.  1 ′ and ¾ are each independently represented by Formula 2 or 3, and at least one of ¾ is represented by Formula 2.
【청구항 3】 [Claim 3]
제 1항에 있어서,  The method of claim 1,
¾, ¾및 ¾중적어도두개는 N인,  At least two of ¾, ¾, and ¾ are N,
화합물.  compound.
【청구항 4】 [Claim 4]
제 1항에 있어서,  The method of claim 1,
내지 가각각독립적으로결합또는페닐렌인,  To each independently a bond or phenylene,
화합물.  compound.
【청구항 5] [Claim 5]
제 1항에 있어서, The method of claim 1,
! 내지 3는 각각 독립적으로, 비치환되거나, 또는 01-4 알킬, 2019/139233 1»(:1^1{2018/013120 ! To 3 are each independently unsubstituted or 0 1-4 alkyl, 2019/139233 1 »(: 1 ^ 1 {2018/013120
할로겐, 시아노, 및 트라( -4알킬)실릴로구성되는군으로부터 선택되는어느 하나의 치환기로 치환된 페닐; 비페닐릴; 터페닐릴; 쿼터페닐릴; 나프틸; 안트라세닐 ; 페난쓰레닐 ; 트리페닐레닐 ; 디메틸플루오레닐 ; 디페닐플루오레닐 ; 디벤조퓨라닐 ; 또는디벤조티오페닐인, Phenyl substituted with any one substituent selected from the group consisting of halogen, cyano, and tra ( -4 alkyl) silyl; Biphenylyl; Terphenylyl; Quarterphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethyl fluorenyl; Diphenylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl;
화합물.  compound.
【청구항 6】 [Claim 6]
제 5항에 있어서, The method of claim 5,
!및 2중적어도하나가페닐기인, The! And two popularly least one group,
화합물.  compound.
【청구항 7] [Claim 7]
제 1항에 있어서,  The method of claim 1,
및 ¾중하나는상기 화학식 2으로표시되고, 나머지 하나는상기 화학식 3으로표시되는것인,  And one of ¾ is represented by Formula 2, and the other is represented by Formula 3,
화합물.  compound.
【청구항 8] [Claim 8]
제 1항에 있어서,  The method of claim 1,
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는어느하나인,  The compound represented by Formula 1 is any one selected from the group consisting of
화합물: compound:
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000090_0001
Figure imgf000091_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000090_0001
Figure imgf000091_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
2019/139233 1»(:1/10公018/013120
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
2019/139233 1 »(: 1/10 公 018/013120
Figure imgf000105_0001
Figure imgf000105_0001
【청구항 9] [Claim 9]
제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및상기 제 1 2019/139233 1»(:1/10公018/013120 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자이되, 상기 유기물층 중 1층 이상이 제 1항 내지 제 8항 중 어느 하나의 항에 따른화합물을포함하는것인유기 발광소자. A first electrode; A second electrode provided to face the first electrode; And the first 2019/139233 1 »(: 1/10 公 018/013120 An organic light-emitting device comprising at least one organic layer provided between an electrode and the second electrode, wherein at least one of the organic layers is one of claims 1 to 8 An organic light emitting device comprising the compound according to any one of claims.
PCT/KR2018/013120 2018-01-09 2018-10-31 Heterocyclic compound and organic light emitting element using same WO2019139233A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880048910.3A CN110944991B (en) 2018-01-09 2018-10-31 Heterocyclic compound and organic light emitting device including the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2018-0002875 2018-01-09
KR20180002875 2018-01-09
KR1020180124557A KR102126884B1 (en) 2018-01-09 2018-10-18 Hetero-cyclic compound and organic light emitting device comprising the same
KR10-2018-0124557 2018-10-18

Publications (1)

Publication Number Publication Date
WO2019139233A1 true WO2019139233A1 (en) 2019-07-18

Family

ID=67218654

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/013120 WO2019139233A1 (en) 2018-01-09 2018-10-31 Heterocyclic compound and organic light emitting element using same

Country Status (1)

Country Link
WO (1) WO2019139233A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210296593A1 (en) * 2018-10-02 2021-09-23 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120286249A1 (en) * 2011-05-13 2012-11-15 Jae-Yong Lee Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus including the device
KR20130128322A (en) * 2012-05-16 2013-11-26 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same
KR20150135070A (en) * 2014-05-22 2015-12-02 제일모직주식회사 Organic compound and composition and organic optoelectric device and display device
KR20170036943A (en) * 2015-09-24 2017-04-04 엘지디스플레이 주식회사 Organic Light Emitting Diode Device
KR20170064379A (en) * 2015-12-01 2017-06-09 희성소재 (주) Hetero-cyclic compound and organic light emitting device using the same
EP3263570A1 (en) * 2016-06-30 2018-01-03 LG Display Co., Ltd. Organic compound, and organic light emitting diode and organic light emitting display device including the same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120286249A1 (en) * 2011-05-13 2012-11-15 Jae-Yong Lee Condensed-cyclic compound, organic light-emitting device comprising the same, and flat panel display apparatus including the device
KR20130128322A (en) * 2012-05-16 2013-11-26 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same
KR20150135070A (en) * 2014-05-22 2015-12-02 제일모직주식회사 Organic compound and composition and organic optoelectric device and display device
KR20170036943A (en) * 2015-09-24 2017-04-04 엘지디스플레이 주식회사 Organic Light Emitting Diode Device
KR20170064379A (en) * 2015-12-01 2017-06-09 희성소재 (주) Hetero-cyclic compound and organic light emitting device using the same
EP3263570A1 (en) * 2016-06-30 2018-01-03 LG Display Co., Ltd. Organic compound, and organic light emitting diode and organic light emitting display device including the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210296593A1 (en) * 2018-10-02 2021-09-23 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same
US12004421B2 (en) * 2018-10-02 2024-06-04 Lg Chem, Ltd. Compound and organic light emitting device comprising the same

Similar Documents

Publication Publication Date Title
KR20200063053A (en) Novel compound and organic light emitting device comprising the same
WO2019117440A1 (en) Organic light-emitting diode
KR102123015B1 (en) Novel compound and organic light emitting device comprising the same
KR20200026080A (en) Novel compound and organic light emitting device comprising the same
KR102225488B1 (en) Novel compound and organic light emitting device comprising the same
EP3862350B1 (en) Novel compound and organic light emitting device using same
KR102392663B1 (en) Novel compound and organic light emitting device comprising the same
KR102126884B1 (en) Hetero-cyclic compound and organic light emitting device comprising the same
CN112789747A (en) Organic light emitting device
WO2018216887A1 (en) Novel compound and organic light-emitting device using same
WO2019208991A1 (en) Novel heterocyclic compound and organic light emitting device using same
EP3730488A1 (en) Novel heterocyclic compound and organic light emitting device using same
KR101959511B1 (en) Novel hetero-cyclic compound and organic light emitting device comprising the same
KR20200057648A (en) Novel compound and organic light emitting device comprising the same
KR20200078156A (en) Novel compound and organic light emitting device comprising the same
KR102264792B1 (en) Novel compound and organic light emitting device comprising the same
KR20210001936A (en) Novel compound and organic light emitting device comprising the same
KR102121433B1 (en) Novel compound and organic light emitting device comprising the same
KR20200088772A (en) Novel compound and organic light emitting device comprising the same
KR102032954B1 (en) Novel hetero-cyclic compound and organic light emitting device comprising the same
TW201726633A (en) Compound and organic light emitting device comprising the same
JP2024501230A (en) organic light emitting device
JP2024504058A (en) organic light emitting device
WO2019139233A1 (en) Heterocyclic compound and organic light emitting element using same
CN113166125A (en) Novel compound and organic light emitting device using the same

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18900490

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18900490

Country of ref document: EP

Kind code of ref document: A1