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WO2018135798A1 - Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant Download PDF

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Publication number
WO2018135798A1
WO2018135798A1 PCT/KR2018/000486 KR2018000486W WO2018135798A1 WO 2018135798 A1 WO2018135798 A1 WO 2018135798A1 KR 2018000486 W KR2018000486 W KR 2018000486W WO 2018135798 A1 WO2018135798 A1 WO 2018135798A1
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group
light emitting
layer
compound
substituted
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PCT/KR2018/000486
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English (en)
Korean (ko)
Inventor
허동욱
이동훈
허정오
장분재
한미연
정민우
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주식회사 엘지화학
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Priority claimed from KR1020180001717A external-priority patent/KR102003351B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880004727.3A priority Critical patent/CN110023306B/zh
Priority to US16/341,884 priority patent/US11228001B2/en
Priority to EP18741013.9A priority patent/EP3527564B1/fr
Priority to JP2019521771A priority patent/JP6801162B2/ja
Publication of WO2018135798A1 publication Critical patent/WO2018135798A1/fr

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    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants

Definitions

  • 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 research 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.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • X 4 are each independently N or CH
  • Li and L 2 are each independently a single bond; Or a substituted or unsubstituted C 6 - 60 arylene; Substituted or unsubstituted C 2 -60 heteroarylene comprising one or more of N, 0 and S,
  • Ri and 3 ⁇ 4 are each independently substituted or unsubstituted C 6 -60 aryl; Or substituted or unsubstituted C 2 -60 heteroaryl comprising one or more of N, 0 and S,
  • Each R 3 is independently C 6 -60 aryl, substituted with one or two cyano, n is an integer of 1 or 2.
  • the present invention is a first electrode; A crab 2 electrode provided to face the first electrode; And an organic light emitting device comprising one or more organic material layers provided between the first electrode and the second electrode. One or more layers of the organic material layers provide an organic light emitting device including the compound of the present invention described above.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compound represented by Chemical Formula 1 may be used as 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. As shown in FIG.
  • 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.
  • the present invention provides a compound represented by the following formula (1).
  • 3 ⁇ 4 and 3 ⁇ 4 are each independently N or -CH
  • Li and L 2 are each independently a single bond; Or a substituted or unsubstituted C 6 - 60 arylene; Substituted or unsubstituted C 2 -60 heteroarylene comprising one or more of N, 0 and S,
  • Ri and 3 ⁇ 4 are each independently substituted or unsubstituted C 6 -60 aryl; Or substituted or unsubstituted C 2 -60 heteroaryl comprising one or more of N, 0 and S,
  • 3 ⁇ 4 is each independently C 6 -60 aryl substituted with one or two cyano, n is an integer of 1 or 2.
  • substituted or unsubstituted is deuterium; Halogen group nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group phosphine oxide group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group alkyl sulfoxy group; Aryl sulfoxy group; Threading; Boron group; An alkyl group; Cycloalkyl group alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group Aralkyl amine group; 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 N, 0 and S atoms, or two or
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group is an aryl group It may also be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40.
  • a compound of the following structure
  • the oxygen of 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.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t_butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine bromide 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. According to another exemplary embodiment, the alkyl group has carbon number of . 1 to 6.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1_methyl-butyl, 1-ethyl-butyl, pentyl, n—pentyl, isopentyl, neopentyl, ter t -pentyl, nuclear chamber, ⁇ -nuclear chamber, 1—methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2 ⁇ ethyl Butyl, heptyl, ⁇ -heptyl, 1-methylnuclear, cyclopentylmethyl, cyclonuxylmethyl octyl, ⁇ -octyl, tert-octyl, 1-methylheptyl 2-ethylnuclear,
  • 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-pentenyl, 3-pentenyl, 3-methyl- 1- Butenyl 1, 3-butadienyl, allyl, 1-phenylvinyl-1 uni day, 2-phenylvinyl -1-yl, 2, 2-diphenylvinyl -1-yl, 2 uniphenyl—2— (naph Yl-1-yl) vinyl-1-yl 2, 2-bis (diphenyl ⁇ 1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited to these.
  • 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. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • a polorerenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted
  • the heterocyclic group is a heterocyclic group containing one or more of 0, ⁇ , Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group , Aridyl, pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl, isoquinoline Group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group.
  • Dibenzothiophene group benzofuranyl group, phenanthroline group (phenanthrol ine), thiazolyl group, isoxoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofura
  • a nil group etc. it is not limited to these.
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group of the aralkyl group 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 of the above-described aryl group except that arylene is a divalent group Can be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the 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.
  • Formula 1 preferably, at least two or more of 3 ⁇ 4, 3 ⁇ 4 and X 4 may be N. The rest is CH. That is, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1—1 to 1-3.
  • L1 and L 2 are each independently a single bond, Or ⁇ .
  • 3 ⁇ 4 and 3 ⁇ 4 may each be any one selected from the group consisting of:
  • 3 ⁇ 4 is each independently phenyl substituted with 1 or 2 cyano, biphenylyl substituted with 1 or 2 cyano, terphenylyl substituted with 1 or 2 cyano, or 1 or It may be any one selected from dimethylfloorenyl substituted with two cyano.
  • the compound represented by the formula (1) is any one selected from the group consisting of:
  • the compound represented by Formula 1 may be prepared by the following Scheme 1, Scheme 2, Scheme 3, and Scheme 4 in a sequential manner.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • the present invention comprises a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a 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 charge, an electron transport layer, an electron injection layer and the like 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 injection layer, the hole transport layer, or a layer for simultaneously injecting and transporting the hole is represented by the formula (1) It includes a compound represented.
  • 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 a layer for simultaneously injecting and transporting electrons includes a compound represented by the formula (1).
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability.
  • electron injection and electron transport of the compound represented by the formula (1) When used in the organic layer that can be done simultaneously, n-type dopants used in the art can be used in combination.
  • the organic material layer may include a light emitting layer and an electron transport layer
  • 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 material 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 of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2. the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2. .
  • FIG. 1 shows a substrate 1 and an anode.
  • the example of the organic light emitting element which consists of the light emitting layer 3 and the cathode 4 is shown.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer.
  • FIG. 2 illustrates a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, and a light emitting layer. (7), an electron transport layer (8), and an example of an organic light emitting element consisting of a cathode (4).
  • the compound represented by the formula (1) is the hole injection layer, hole transport layer, light emitting layer And it may be included in one or more layers of 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.
  • 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 Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, coating, etc., but is not limited thereto.
  • 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 (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode, the second .
  • the electrode is a cathode, or the first electrode is a cathode, and 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, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, rhythm oxide, rhodium tin oxide (IT0), indium zinc oxide (IZ0); A combination of a metal such as ⁇ 0: ⁇ 1 or SN0 2 : Sb and an ' oxide; Conductive polymers such as poly (3-methylthiophene), poly [3,4— (ethylene-1,2-dioxy) thio3 ⁇ 4], 00 poly), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, Metals such as aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. It is preferable that H0M0 (highest occupied molecu ar arbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.
  • the hole injection material examples include metal porphyr (in), oligothiophene, arylamine-based organics, hexanitrile nucleated azatriphenylene-based organics, quinacr i done-based organics, and perylene ( perylene) . .
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport layer is a material that can transport holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material. This large material is suitable.
  • the light emitting material has a hole and electron from the hole number, songcheung and the electron transport layer each as a transport material which may be a visible light by combining received, a high quantum efficiency for fluorescence and the phosphor is preferred.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and the arylamino compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the above-described arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group ' and an arylamino group are substituted or unsubstituted. .
  • 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 a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do.
  • 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, kale, ytterbium and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode, the electrons Compound which has the ability to transport, the electron injection effect from a cathode, the electron injection effect with respect to a light emitting layer or a light emitting material, prevents the movement of the excitons produced
  • they include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like .
  • 8'hydroxyquinolinato lithium as the metal complex compound.
  • the present invention is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the production of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
  • Example KE1 is only for illustrating the present invention, and the scope of the present invention is not limited thereto.
  • a compound represented by Chemical Formula E2-P2 was prepared by the same method as E1-P2 of Example 1, except that each starting material was performed in the same manner as in the above Scheme.
  • a compound represented by Chemical Formula E3-P1 was prepared by the same method as E1-P1 of Example 1, except that each starting material was performed in the same manner as in the above Scheme.
  • a compound represented by Chemical Formula E5 was prepared in the same manner as in Example E1 except that each starting material was performed in the same manner as in the above Scheme.
  • a compound represented by Chemical Formula E12 was prepared in the same manner as in Example 1, except that each starting material was used in the same manner as described above. MS [M + H] + -653
  • a compound represented by Chemical Formula E19 was prepared by the same method as E1 of Example 1, except that each starting material was performed in the same manner as in the above Scheme.
  • a compound represented by Chemical Formula E21 was prepared by the same method as E1 in Example 1, except that each starting material was performed in the same manner as in the above scheme.
  • a compound represented by Chemical Formula E22 was prepared by the same method as E1 in Example 1, except that each starting material was performed in the same manner as in the above Scheme.
  • a glass substrate coated with a thin film having a thickness of 1000 A (IT0 (indi um t in oxi de)) was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned.
  • IT0 in um t in oxi de
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly with a filter of Mi 1 1 ipore Co. as a distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following HI-A compound was thermally vacuum deposited to a thickness of 600 A on the prepared IT0 transparent electrode to form a hole injection layer.
  • the following HAT compound 50 A and the following HT—A compound 600 A were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the light emitting layer was formed by vacuum depositing the following BH compound and BD compound at a weight ratio of 25: 1 on the hole transport layer with a film thickness of 20 nm.
  • Compound (E1) of Example 1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 350 A.
  • Lithium fluoride (LiF) and aluminum at a thickness of 1000 A were sequentially deposited on the electron injection and transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at a deposition rate of 2 A / sec.
  • the organic light emitting device was manufactured by maintaining 7 to 5 X ⁇ 5 torr.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compounds (E2 to E22) of Examples 2 to 22 instead of the compound (E1) of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound (ET—A to ET—K) instead of the compound (El) of Example 1.
  • the driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in the above Experimental Example and Comparative Experimental Example were measured at a current density of 10 mA / cm 2 , and the time of 90% of the initial luminance at a current density of 20 mA / cm 2 ( T90) was measured. The results are shown in Tables 1 and 2 below.
  • the compound represented by Formula 1 according to the present invention can be used in the organic material layer capable of simultaneous electron injection and electron transport of the organic light emitting device.
  • the compound of Formula 1 according to the present invention is dibenzofuran (or dibenzothiophene) in triazine (or pyrimidine) and Driving voltage, efficiency and lifespan of organic light emitting diodes compared to compounds substituted with heteroaryl groups other than that of Formula 1 It was confirmed that it is remarkably excellent in terms of.
  • the compound of Formula 1 according to the present invention is remarkably superior in terms of driving voltage, efficiency and lifespan of an organic light emitting device as compared to a compound in which only triazine (or pyrimidine) is substituted for dibenzofuran (or dibenzothiophene).
  • dibenzofuran or dibenzo thiophene
  • the organic light emitting device is significantly superior in terms of driving voltage, efficiency and lifetime.
  • Substrate 2 Anode

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un élément électroluminescent organique le comprenant.
PCT/KR2018/000486 2017-01-20 2018-01-10 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2018135798A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201880004727.3A CN110023306B (zh) 2017-01-20 2018-01-10 新的杂环化合物和包含其的有机发光器件
US16/341,884 US11228001B2 (en) 2017-01-20 2018-01-10 Hetero-cyclic compound and organic light emitting device comprising the same
EP18741013.9A EP3527564B1 (fr) 2017-01-20 2018-01-10 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant
JP2019521771A JP6801162B2 (ja) 2017-01-20 2018-01-10 新規なヘテロ環式化合物およびこれを利用した有機発光素子

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KR20170009884 2017-01-20
KR10-2017-0009884 2017-01-20
KR10-2018-0001717 2018-01-05
KR1020180001717A KR102003351B1 (ko) 2017-01-20 2018-01-05 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109134443A (zh) * 2018-09-12 2019-01-04 陕西莱特光电材料股份有限公司 一种新型有机电致发光层材料及其制备方法与应用
JP2020507575A (ja) * 2017-04-13 2020-03-12 エルジー・ケム・リミテッド 新規なヘテロ環式化合物およびこれを含む有機発光素子
WO2020111663A1 (fr) * 2018-11-26 2020-06-04 두산솔루스 주식회사 Composé organique et dispositif électroluminescent organique l'utilisant

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000051826A (ko) 1999-01-27 2000-08-16 성재갑 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
KR20150076129A (ko) * 2013-12-26 2015-07-06 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
US20150336937A1 (en) * 2014-05-21 2015-11-26 Samsung Electronics Co., Ltd. Carbazole compound and organic light emitting device incuding the same
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
WO2016129672A1 (fr) * 2015-02-13 2016-08-18 コニカミノルタ株式会社 Dérivé hétérocyclique aromatique et élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage utilisant le dérivé hétérocyclique aromatique
KR20160112111A (ko) * 2015-03-18 2016-09-28 에스에프씨 주식회사 유기발광소자용 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000051826A (ko) 1999-01-27 2000-08-16 성재갑 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
KR20150076129A (ko) * 2013-12-26 2015-07-06 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
US20150336937A1 (en) * 2014-05-21 2015-11-26 Samsung Electronics Co., Ltd. Carbazole compound and organic light emitting device incuding the same
WO2016129672A1 (fr) * 2015-02-13 2016-08-18 コニカミノルタ株式会社 Dérivé hétérocyclique aromatique et élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage utilisant le dérivé hétérocyclique aromatique
KR20160112111A (ko) * 2015-03-18 2016-09-28 에스에프씨 주식회사 유기발광소자용 화합물 및 이를 포함하는 유기 발광 소자

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020507575A (ja) * 2017-04-13 2020-03-12 エルジー・ケム・リミテッド 新規なヘテロ環式化合物およびこれを含む有機発光素子
US11081655B2 (en) 2017-04-13 2021-08-03 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device using the same
CN109134443A (zh) * 2018-09-12 2019-01-04 陕西莱特光电材料股份有限公司 一种新型有机电致发光层材料及其制备方法与应用
WO2020111663A1 (fr) * 2018-11-26 2020-06-04 두산솔루스 주식회사 Composé organique et dispositif électroluminescent organique l'utilisant

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