[go: up one dir, main page]

WO2019139233A1 - Composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Composé hétérocyclique et élément électroluminescent organique l'utilisant 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
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2018/013120
Other languages
English (en)
Korean (ko)
Inventor
하재승
김연환
이성재
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
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/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201880048910.3A priority Critical patent/CN110944991B/zh
Publication of WO2019139233A1 publication Critical patent/WO2019139233A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic 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
    • C07D251/14—Heterocyclic 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
    • C07D251/24—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic 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
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

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

La présente invention concerne un nouveau composé hétérocyclique et un élément électroluminescent organique l'utilisant.
PCT/KR2018/013120 2018-01-09 2018-10-31 Composé hétérocyclique et élément électroluminescent organique l'utilisant Ceased WO2019139233A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880048910.3A CN110944991B (zh) 2018-01-09 2018-10-31 杂环化合物及包含其的有机发光器件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2018-0002875 2018-01-09
KR20180002875 2018-01-09
KR10-2018-0124557 2018-10-18
KR1020180124557A KR102126884B1 (ko) 2018-01-09 2018-10-18 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

Publications (1)

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

Family

ID=67218654

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/013120 Ceased WO2019139233A1 (fr) 2018-01-09 2018-10-31 Composé hétérocyclique et élément électroluminescent organique l'utilisant

Country Status (1)

Country Link
WO (1) WO2019139233A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021109853A (ja) * 2020-01-10 2021-08-02 東ソー株式会社 トリアジン化合物、及び有機電界発光素子用材料
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 (ko) * 2012-05-16 2013-11-26 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20150135070A (ko) * 2014-05-22 2015-12-02 제일모직주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR20170036943A (ko) * 2015-09-24 2017-04-04 엘지디스플레이 주식회사 유기전계발광소자
KR20170064379A (ko) * 2015-12-01 2017-06-09 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
EP3263570A1 (fr) * 2016-06-30 2018-01-03 LG Display Co., Ltd. Composé organique et diode électroluminescente et dispositif d'affichage électroluminescent organique le comprenant

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 (ko) * 2012-05-16 2013-11-26 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR20150135070A (ko) * 2014-05-22 2015-12-02 제일모직주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR20170036943A (ko) * 2015-09-24 2017-04-04 엘지디스플레이 주식회사 유기전계발광소자
KR20170064379A (ko) * 2015-12-01 2017-06-09 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
EP3263570A1 (fr) * 2016-06-30 2018-01-03 LG Display Co., Ltd. Composé organique et diode électroluminescente et dispositif d'affichage électroluminescent organique le comprenant

Cited By (4)

* 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
JP2021109853A (ja) * 2020-01-10 2021-08-02 東ソー株式会社 トリアジン化合物、及び有機電界発光素子用材料
JP7547728B2 (ja) 2020-01-10 2024-09-10 東ソー株式会社 トリアジン化合物、及び有機電界発光素子用材料

Similar Documents

Publication Publication Date Title
CN112673004B (zh) 新的化合物和包含其的有机发光器件
CN114163421B (zh) 新的杂环化合物和包含其的有机发光器件
WO2019117440A1 (fr) Diode luminescente organique
EP3862350B1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
KR102123015B1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102392663B1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102225488B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102126884B1 (ko) 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
TWI845932B (zh) 有機發光元件
WO2019208991A1 (fr) Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
KR20210001936A (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
WO2018216887A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
EP3730488A1 (fr) Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant
KR101959511B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
EP4266390B1 (fr) Dispositif électroluminescent organique
KR20240094080A (ko) 신규한 화합물 및 이를 포함한 유기 발광 소자
KR20200078156A (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
JP7680140B2 (ja) 新規な化合物およびこれを利用した有機発光素子
JP7707508B2 (ja) 有機発光素子
KR20200088772A (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR20200057651A (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR20200057648A (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2019139233A1 (fr) Composé hétérocyclique et élément électroluminescent organique l'utilisant
KR102264792B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102121433B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자

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