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WO2019013509A1 - Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant - Google Patents

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

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Publication number
WO2019013509A1
WO2019013509A1 PCT/KR2018/007756 KR2018007756W WO2019013509A1 WO 2019013509 A1 WO2019013509 A1 WO 2019013509A1 KR 2018007756 W KR2018007756 W KR 2018007756W WO 2019013509 A1 WO2019013509 A1 WO 2019013509A1
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group
layer
compound
light emitting
organic
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English (en)
Korean (ko)
Inventor
서상덕
홍성길
김성소
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020180078986A external-priority patent/KR102020029B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201880025969.0A priority Critical patent/CN110546143B/zh
Publication of WO2019013509A1 publication Critical patent/WO2019013509A1/fr
Anticipated expiration legal-status Critical
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research is proceeding.
  • 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 material layer may have a multilayer structure composed of different materials.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, have.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound and an organic device containing the same.
  • X is O or S
  • Ri to < RTI ID 0.0 > 3 < / RTI > are each fused with a * in the formula 2 to form a fused ring,
  • L is a bond; Substituted or unsubstituted C 6 - 60 arylene; Or a substituted or unsubstituted C 2 - 60 heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,
  • the present invention also provides a plasma display panel comprising: a first electrode; A second electrode opposing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 do.
  • the compound represented by the formula (1) can be used as a material for an organic material layer of an organic light emitting device, and can improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting device.
  • the compound represented by the above-described formula (1) can be used as a hole injecting, hole transporting, hole injecting and transporting, luminescence, electron transporting, or electron injecting material.
  • Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • Fig. 2 is a cross-sectional view of a light emitting device according to the present invention, which includes a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, (7), an electron transport layer (8), and a cathode (4).
  • ⁇ or ⁇ * means a bond connected to another substituent, and a single bond means a case where no separate atom exists in a portion represented by L.
  • substituted or unsubstituted A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected
  • the substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.
  • the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an ester group oxygen in a straight-chain, branched-chain 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.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilylpropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine d-
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- n-pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, N-heptyl, n-heptyl, 1-methylnucleyl, cyclopentylmethylcyclohexylmethyl, octyl, n-octyl, tert-octyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like.
  • the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms.
  • the cycloalkyl group has 3 to 20 carbon atoms.
  • the number of carbon atoms of the cycloalkyl group is 3 to 6.
  • the aryl group is not particularly limited, but is preferably a carbon number of 6 or less, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may form a bond spiro structure. Wherein said fluorenyl group is substituted
  • the heterometallic group includes heteroatoms of 0, N, Si and S
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include a thiophene group, a furan group, a pyridine group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , An acridyl group pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrimidinyl group, a pyrazinopyrazinyl group, , Indole group, carbazole group, benzooxazole group benzo
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.
  • an alkyl group, an alkylaryl group, and an alkyl group in the alkylamine group are the same as the examples of the alkyl group described above.
  • the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heteroaryl groups.
  • the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
  • the description of the aryl group described above can be applied except that arylene is a divalent group.
  • the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.
  • the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other.
  • the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
  • the present invention also provides a compound represented by the above formula (1).
  • X is 0 or S.
  • two adjacent ones are bonded to each other with * in the above formula (2) to form a fused ring, and the remainder is hydrogen.
  • the two adjacent functional groups of the above-mentioned Chemical Formulas 1 to 3 means a functional group substituted on each of two carbon atoms forming a chemical bond in the above Chemical Formula 1, for example, 3 ⁇ 4 and 3 ⁇ 4).
  • a fused ring is formed by bonding with * in the above formula (2), or R 2 and R 3 in the above formula May be combined with * in the formula (2) to form a fused ring.
  • the remaining two functional groups not forming a bond with the * in Formula 2 may be hydrogen after bonding adjacent two of 3 ⁇ 4 and R 3 to each other with * in Formula 2 to form a fused ring. That is, the compound may be represented by the following formula 1-1 or 1-2:
  • X, 4 and 3 ⁇ 4 are as defined in the above formula (1). Meanwhile, adjacent two of R 1 to R 3 of the formula (1) may bond with * in the formula (2) to form a fused ring, and at the same time, one of the 3 ⁇ 4 and 3 ⁇ 4 of the formula (1) .
  • L may be bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene, and more specific examples may be a bond or phenylene.
  • phenylene may be any one selected from the group consisting of
  • each Z is independently N or CH, provided that at least one of Z may be N.
  • a and Ar 2 are each independently a substituted or unsubstituted C 6 -60 aryl; Or a substituted or unsubstituted C 2 -C 60 heteroaryl containing one or more heteroatoms selected from the group consisting of O, N, Si and S; More specifically, for example, A and Ar 2 may each independently be phenyl, biphenyl, terphenyl, dimethylfluorenyl, naphthyl, pyridinyl, dibenzofuranyl, or dibenzothiophenyl .
  • the compound may be any one selected from the group consisting of the following compounds: // : / O 9sz-z-00 8 SSM > d 60S206SZAV
  • the present invention provides a liquid crystal display comprising: a first electrode; A second electrode disposed opposite to the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1, 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 injecting layer, a hole transporting layer emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
  • the organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes.
  • the hole injecting layer, the hole transporting layer, May be included.
  • the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).
  • the electron transport layer, the electron injection layer, or the layer that simultaneously transports electrons and injects electrons may include the electron transport layer, the electron injection layer, or the layer that performs electron transport and electron injection simultaneously.
  • the organic material layer may include a light emitting layer and an electron transporting layer
  • the electron transporting layer may include a compound represented by the general formula (1).
  • the compound represented by Formula 1 may be included in at least one of the electron blocking layer and the hole blocking layer.
  • the electron blocking layer and the hole blocking layer may be organic layers adjacent to the light emitting layer, respectively.
  • the compound represented by Formula 1 may be included in the light emitting layer, the electron transporting layer, or the hole blocking layer.
  • 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 hole injecting layer and the hole transporting layer between the first electrode and the light emitting layer, and the electron transporting layer and the electron injecting layer between the light emitting layer and the second electrode are further And the like.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which an anode, one or more organic compound layers and an anode are sequentially stacked on a substrate.
  • FIGS. Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • Fig. 2 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, (7), an electron transport layer (8), and a cathode (4).
  • the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art except that one or more of the organic layers include a compound represented by the above formula (1).
  • the organic light emitting diode when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic bug, and a second electrode on a substrate.
  • a metal oxide or a metal oxide having an electrical conductivity or an alloy thereof may be formed on the substrate by a PVDC photovapor deposition (PVD) method such as sputtering or electron beam evaporation Forming an anode, depositing an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon.
  • PVD PVDC photovapor deposition
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is a cathode.
  • the anode material a material having a large work function is preferably used so that hole injection can be smoothly performed with the organic material layer.
  • the positive electrode material include metals such as vanadium chrome, copper, zinc, and gold; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ⁇ 0: ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, It is not.
  • the negative electrode material it is preferable that the negative electrode material is a material having a small workability to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lyrium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable.
  • the HOMO highest occupied molecular orbital of the hole injecting material is preferably between the work function of the anode material and H0M0 of the surrounding organic layer.
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, nuclear nitrile-tetra-phenylene-based organic materials, quinacridone-based organic materials, perylene perylene based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the luminescent material.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. This large material is suitable. Specific examples thereof include, but are not limited to, arylamine-based organic substances, conductive polymers, and block-conjugated polymers having a conjugated portion and a non-conjugated portion together.
  • the light emitting material is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • the light emitting layer may include a host material and a dopant material as described above.
  • the host material may further include a condensed aromatic ring derivative or a heterocyclic compound in addition to the compound represented by the formula (1).
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds and fluoranthene compounds.
  • heterocycle-containing compounds include carbazole derivatives, dibenzofurane derivatives L-ladder furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivative examples include a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • styrylamine compound examples include substituted or unsubstituted At least one arylbis Wherein the substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Suitable. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; And hydroxyflavone-metal complexes, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to 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, in each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to the hole injection layer and is excellent in the thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) , Tris (8-hydroxyquinolinato) aluminum, tri (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxyquinolinato) (2-methyl-8-quinolinato) gallium, bis (2-methyl-8-quinolinato) Methyl-8-quinolinato) (1-naphthalato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium and the like.
  • the organic light emitting device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • the preparation of the compound represented by Formula 1 and the organic light emitting device comprising 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 thereto.
  • the glass substrate coated with ITO (Indium Tin Oxide) thin film of 1, 400A thickness was washed with ultrasonic wave in distilled water containing detergent.
  • ITO Indium Tin Oxide
  • Fischer Co. was used as a detergent
  • distilled water which was filtered by a filter of a product manufactured by Millipore Co., Ltd.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after using an oxygen plasma cleaning the substrate vacuum 5 minutes, it was transported to the substrate by depositing machine.
  • HT-A [P-D0PANT]
  • HT-B was thermally vacuum deposited on the HT-B to a thickness of 450 A as an electron blocking layer.
  • ET-A Next, ET-B and Liq were thermally vacuum deposited at a ratio of 2: 1 to a thickness of 250A as an electron transporting and injecting layer, followed by vacuum evaporation of LiF and magnesium at a ratio of 1: Respectively.
  • the organic light emitting devices of Examples 2 to 7 and Comparative Examples 1 to 4 were fabricated by the same method as in Example 1 except that the first host material was changed as shown in Table 1 .
  • the voltage, the efficiency, and the lifetime (T95) were measured by applying a current to the organic light emitting devices manufactured in Examples 1 to 7 and Comparative Examples 1 to 4, and the results are shown in Table 1 below. At this time,
  • T95 means the time until the initial luminance decreases to 95% at a current density of 20mA / cm 2.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2018/007756 2017-07-10 2018-07-09 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant Ceased WO2019013509A1 (fr)

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CN201880025969.0A CN110546143B (zh) 2017-07-10 2018-07-09 新型杂环化合物及包含其的有机发光器件

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