WO2018190682A1 - Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant - Google Patents

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

Info

Publication number
WO2018190682A1
WO2018190682A1 PCT/KR2018/004352 KR2018004352W WO2018190682A1 WO 2018190682 A1 WO2018190682 A1 WO 2018190682A1 KR 2018004352 W KR2018004352 W KR 2018004352W WO 2018190682 A1 WO2018190682 A1 WO 2018190682A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
phenyl
group
light emitting
unsubstituted
Prior art date
Application number
PCT/KR2018/004352
Other languages
English (en)
Korean (ko)
Inventor
홍완표
정민우
윤홍식
차용범
김연환
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180042888A external-priority patent/KR102022691B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880008146.7A priority Critical patent/CN110198933B/zh
Publication of WO2018190682A1 publication Critical patent/WO2018190682A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound compound and a light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • Ri and 3 ⁇ 4 are each independently hydrogen; C 2 -6o heteroaryl group containing a substituted or unsubstituted N; Or - ⁇ ( ⁇ ) ( ⁇ ⁇ 2 ),
  • R 2 to R 5 are each independently hydrogen; C 2 -6o heteroaryl group containing a substituted or unsubstituted N; Or N (Ar 3 ) (Ar 4 );
  • a and Ar 2 are each independently substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted C 7 -60 arylalkyl; Substituted or unsubstituted C 7 -60 alkylaryl; Or substituted or unsubstituted C 2 -60 heteroaryl including one or more of 0, N, and S, wherein at least one of An and Ar 2 includes only one aryl or heteroaryl ring,
  • Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted C 7 -60 arylalkyl; Substituted or unsubstituted C 7 — 60 alkylaryl; Or C 2 -60 heteroaryl including one or more of substituted, substituted or substituted 0, N, and S.
  • the present invention is a first electrode; Crab 2 electrodes provided to face the first electrode And at least one organic material layer provided between the crab first electrode and the crab two electrodes, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1 to provide an organic light emitting device. do.
  • 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 composed 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.
  • an organic electroluminescent element for a display apparatus
  • long life is calculated
  • a device using a compound proposed so far as a hole injection layer or a hole transport layer does not have sufficient electronic durability, and thus, device life is required to be improved.
  • the problem of device life of the organic EL device is that electrons that cannot be recombined when holes and electrons recombine and emit light near the interface between the light emitting layer and the hole transport layer enter the hole transport layer and damage the electrons to the hole transport material. Is to deteriorate.
  • the present invention has been made to solve the above problems, and according to the present invention, an organic EL device having an improved device life can be provided by suppressing the deterioration mechanism of the device caused by electrons entering the hole transport layer.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cyclo.alkyl 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 N, 0, and S
  • 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 can be interpreted as a substituent to which two phenyl groups are linked.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryllenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • a fluorenyl group may be substituted, and two substituents may be substituted with each other.
  • the heteroaryl group is a heteroaryl group containing one or more of 0, N, and S as heterologous elements, and the carbon number is not particularly limited, but the carbon number It is preferable that it is 2-60.
  • heteroaryl 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 and triazole group , Acridil, 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, phenanthrolin group (phenanthrol)
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • 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 and n- pentyl, isopentyl, neopentyl, tert- pentyl, haeksil, n - haeksil, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3_-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2—ethylnuclear, 2-
  • 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 among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the alkyl group described above.
  • the arylene is described above except that it is a divalent group. The description regarding aryl groups may apply.
  • heteroarylene is
  • Ri and 3 ⁇ 4 are each independently hydrogen; C 2 -6o heteroaryl group containing a substituted or unsubstituted N; Or -N (A ri ) (Ar 2 ),
  • R2 to R 5 are each independently hydrogen; C 2 -6o heteroaryl group containing a substituted or unsubstituted N; Or _N (Ar 3 ) (Ar 4 );
  • An and Ar 2 are each independently substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted C 7 -60 arylalkyl; Substituted or unsubstituted C 7 -60 alkylaryl; Or substituted or unsubstituted C 2 -60 heteroaryl including one or more of 0, N, and S, wherein at least one of A and Ar 2 includes only one aryl or heteroaryl ring,
  • Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted C 7 -60 arylalkyl; Substituted or unsubstituted C 7 -60 alkylaryl; Or C 2 -60 heteroaryl including one or more of substituted, unsubstituted 0, N, and S.
  • Chemical Formula 1 preferably, at least one of C 2 -60 heteroaryl including N substituted or unsubstituted; Or -N (A ri ) (Ar 2 ) or R 2 C 2 -60 heteroaryl, wherein at least one of R 5 is substituted or unsubstituted N; Or -N (Ar 3 ) (Ar 4 ).
  • Chemical Formula 1 may be represented by the following Chemical Formula 2 or Chemical Formula 3:
  • Ri to 3 ⁇ 4 are as defined in Formula 1 above.
  • ,, and 3 ⁇ 4 are hydrogen, and one of R 4 is hydrogen, the other is C 2 -60 heteroaryl including substituted or unsubstituted N; Or _N (Ar 3 ) (Ar 4 ). More preferably, one of 3 ⁇ 4 and one is hydrogen and the other is one of:
  • Xi to 3 ⁇ 4 are each independently CH, or N, provided that at least one of 3 ⁇ 4 is N,
  • Ar ' 2 is phenyl, phenyl substituted with trimethylsilyl, phenyl substituted with triphenylsilyl, biphenylyl, dimethylfluorenyl, dibenzofuranyl, (dibenzofuranyl) phenyl, dibenzothiophenyl, or ( Dibenzothiophenyl) phenyl;
  • Ar ' 3 and Ar' 4 are each independently phenyl or biphenylyl
  • Ar ' 5 to Ar' 8 are each independently hydrogen, phenyl, biphenylyl, or carbazolyl,
  • Ar ' 9 is phenyl or biphenylyl.
  • R 2 , R 4 , and 3 ⁇ 4 are hydrogen, any one of 3 ⁇ 4 is hydrogen, and the other is C 2 -60 heteroaryl including substituted or unsubstituted N; Or -N (Ar 3 ) (Ar 4 ). More preferably, one of 3 ⁇ 4 and 3 ⁇ 4 is hydrogen, and the other is any of the following: ⁇ ⁇ ⁇ 3
  • Xi to 3 ⁇ 4 are each independently CH, or N, provided that at least one of 3 ⁇ 4 to 3 ⁇ 4 is N,
  • Ar'2 is phenyl, phenyl substituted with trimethylsilyl, phenyl substituted with triphenylsilyl, biphenylyl, dimethylfluorenyl, dibenzofuranyl, (dibenzofuranyl) phenyl, dibenzothiophenyl, or ( Dibenzothiophenyl) phenyl, provided that at least one of ⁇ ⁇ ⁇ and Ar'2 is phenyl,
  • Ar ' 3 and Ar' 4 are each independently phenyl or biphenylyl
  • Ar ' 5 to Ar' 8 are each independently hydrogen, phenyl, biphenylyl, or carbazolyl,
  • Ar'g is phenyl or biphenylyl.
  • A, Ar 2) Ar 3 , and Ar 4 may be each independently a compound having a structure as follows, but is not limited thereto:
  • Compound represented by the formula (1) is a tertiary amine group through the Grignard or Buchwald-Hartwig reaction based on bromo ⁇ dibenzofuran as a starting material It can manufacture by substitution. 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 crab 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 valuables 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 and the like as an organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes may be represented by Formula 1 above.
  • 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 electron transport and electron injection The simultaneous layer contains 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 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 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 emission 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 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 layer 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. At this time, such as sputtering or e-beam evaporat i on Using a PVD method, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer are formed thereon.
  • the organic material layer comprising a
  • 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 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 and the like, 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 (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the anode material a material having a large work function is generally preferred to facilitate injection of holes into the organic material layer.
  • the positive electrode material is a metal or an alloy thereof such as vanadium, keureum, copper, zinc, gold; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ⁇ 0: A1 or SN0 2 : Combination of metal and oxide, such as Sb; Poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (? £ 0 0, conductive polymers such as polypyrrole and polyaniline, etc., but are not limited thereto.
  • the negative electrode material is generally a material having a small work function to facilitate electron injection into the organic material layer.
  • the hole injection layer is a layer for injecting holes from an electrode, and has a capability of transporting holes to a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect to a light emitting layer or a light emitting material, and is generated in a 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.
  • HOMCXhighest occupied mol ecular orbital 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 include metals such as porphyr in, oligothiophene, aralamine-based organic matter, nucleonitrile-nucleated azatriphenylene-based organic material, and quinacr i done-based organic material, perylene ( peryl ene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • a hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring the holes to the light emitting layer. This is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, 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 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 there are an aromatic amine derivative strylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like.
  • 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.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and 1 or 2 in the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group. The substituent selected above is 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 is a material that can inject electrons well from the cathode and move 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 a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, In each case it is followed by a layer of aluminum or silver.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, metal Complex compounds and nitrogen-containing 5-membered ring derivatives include, but are not limited to.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, 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 [h] Quinolinato) beryllium, bis (1-hydroxybenzo ' [h] quinolinato) zinc, bis (2-methyl-8 -quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium, etc.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • 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 organic layer was extracted with aqueous ammonium chloride solution and ethyl acetate, dried over magnesium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography using ethyl acetate and n -nucleic acid as a developing solvent. After vacuum drying, the target intermediate A was obtained as lO.lg (yield: 73.6%).
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was put in distilled water in which a detergent was dissolved and washed with ultrasonic waves.
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Mi 1 lipore Co. was used as distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning 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 HAT compound was deposited on the ⁇ transparent electrode thus prepared, and an acceptor film having a thickness of 5 nm was formed. On the acceptor film, By depositing, a first hole transport layer having a thickness of 100 nm was formed. Subsequent to the film formation of the crab 1 hole transport layer, Compound 1 prepared in advance was deposited to form a second hole transport layer having a thickness of 20 nm. On the hole transport layer, the following CBP compound and the following Ir (ppy) 3 compound were co-deposited at a thickness of 40 nm to obtain a phosphorescent layer. The concentration of Ir (ppy) 3 was 10 mass%.
  • the following ET1 compound was deposited on the phosphorescent layer to form an electron transport layer having a thickness of 20 nm.
  • Lithium fluoride (LiF) having a thickness of 1 ⁇ and a metal having a thickness of 80 nm were sequentially formed on the electron transporter.
  • A1 was sequentially stacked to form an electron injection layer and a cathode, thereby manufacturing an organic light emitting device.
  • LiF as an electron injection layer was formed at a film formation rate of lA / min.
  • the organic light-emitting device was manufactured in the same manner as in Experiment 1, except that Compound 1 was used instead of Compound 1 to form the C. 2 hole transport layer.
  • the lifetime (T80) means the time required for the luminance to be reduced to 80% from the initial luminance (5000 nit) after driving the organic light emitting diode.
  • the organic light emitting device manufactured using the compound according to the present invention as a hole transporting material has excellent performance in terms of driving voltage, luminous efficiency, and lifetime compared to the organic light emitting devices of Comparative Experiments 1 to 3. It can be seen that.
  • Experimental Example 5
  • a glass substrate (corning 7059 glass) coated with ⁇ (indium tin oxide) to a thickness of 1000 A was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Fischer Co. was used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After washing the ITO for 30 minutes, Repeated twice with distilled water, ultrasonic cleaning was performed for 10 minutes. After washing the distilled water, ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried. The following HAT compound was thermally vacuum deposited to a thickness of 500 A on the prepared IT0 transparent electrode to form a hole injection layer.
  • the following HT 2 compound was vacuum deposited to a thickness of 400 A to form a hole transport layer.
  • the following HI compound and the following D1 compound were vacuum-deposited at the thickness of 300 A by the increase ratio of 9: 1, and the light emitting layer was formed.
  • the previously prepared compound 5 and LiQ (Lithium Quinolate) were vacuum deposited to a thickness of 350 A in a weight ratio of 1: 1 to form an electron injection and transport layer on the emission layer.
  • An organic light emitting device was manufactured by sequentially depositing aluminum having a thickness of 12 A and lithium fluoride (LiF) at a thickness of 12 A on the electron injection and transport layer to form a cathode.
  • the organic light emitting device was manufactured by the same method as Experimental Example 5, except that compound 6 was used instead of compound 5 to form an electron injection and transport layer. Comparative Experiments 4 and 5
  • the driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm 2 , and 20 mA / cm 2 .
  • the lifetime (T95) was measured at the current density, and the results are shown in Table 2 below. At this time, the life (T95) means the time required to decrease to 95% of the initial luminance at a current density of 20 mA / cm 2 .

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un dispositif électroluminescent organique l'utilisant.
PCT/KR2018/004352 2017-04-13 2018-04-13 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant WO2018190682A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880008146.7A CN110198933B (zh) 2017-04-13 2018-04-13 新型杂环化合物及利用其的有机发光元件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20170048046 2017-04-13
KR10-2017-0048046 2017-04-13
KR10-2018-0042888 2018-04-12
KR1020180042888A KR102022691B1 (ko) 2017-04-13 2018-04-12 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

Publications (1)

Publication Number Publication Date
WO2018190682A1 true WO2018190682A1 (fr) 2018-10-18

Family

ID=63792697

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/004352 WO2018190682A1 (fr) 2017-04-13 2018-04-13 Nouveau composé hétérocyclique et dispositif électroluminescent organique l'utilisant

Country Status (1)

Country Link
WO (1) WO2018190682A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021033731A1 (fr) * 2019-08-19 2021-02-25 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1095972A (ja) * 1996-08-02 1998-04-14 Mitsui Petrochem Ind Ltd 有機電界発光素子
JP2004091350A (ja) * 2002-08-30 2004-03-25 Canon Inc モノアミノフルオレン化合物およびそれを使用した有機発光素子
KR20110069077A (ko) * 2008-10-17 2011-06-22 미쓰이 가가쿠 가부시키가이샤 방향족 아민 유도체, 및 그것들을 이용한 유기 일렉트로루미네센스 소자
KR20150038193A (ko) * 2012-07-23 2015-04-08 메르크 파텐트 게엠베하 2-디아릴아미노플루오렌의 유도체 및 이를 함유하는 유기 전자 화합물

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1095972A (ja) * 1996-08-02 1998-04-14 Mitsui Petrochem Ind Ltd 有機電界発光素子
JP2004091350A (ja) * 2002-08-30 2004-03-25 Canon Inc モノアミノフルオレン化合物およびそれを使用した有機発光素子
KR20110069077A (ko) * 2008-10-17 2011-06-22 미쓰이 가가쿠 가부시키가이샤 방향족 아민 유도체, 및 그것들을 이용한 유기 일렉트로루미네센스 소자
KR20150038193A (ko) * 2012-07-23 2015-04-08 메르크 파텐트 게엠베하 2-디아릴아미노플루오렌의 유도체 및 이를 함유하는 유기 전자 화합물

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
WU, C. ET AL.: "A New Multifunctional Fluorenyl Carbazole Hybrid for High Performance Deep Blue Fluorescence, Orange Phosphorescent Host and Fluorescence/phosphorescence White OLEDs", DYES AND PIGMENTS, vol. 97, no. 2, May 2013 (2013-05-01), pages 273 - 277, XP028980340, Retrieved from the Internet <URL:https://doi.org/10.1016/j.dyepig.2012.12.028> *
ZHAO, Z. ET AL.: "Construction of Efficient Solid Emitters with Conventional and AIE Luminogens for Blue Organic Light-emitting Diodes", JOURNAL OF MATERIALS CHEMISTRY, vol. 21, no. 29, 2011, pages 10949 - 10956, XP055559216, Retrieved from the Internet <URL:DOI:10.1039/c1jm10221d> *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021033731A1 (fr) * 2019-08-19 2021-02-25 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

Similar Documents

Publication Publication Date Title
KR101913926B1 (ko) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR101953175B1 (ko) 함질소 다환 화합물 및 이를 이용하는 유기 발광 소자
JP6673544B2 (ja) ヘテロ環化合物およびこれを含む有機発光素子
KR101978453B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR101755093B1 (ko) 신규한 화합물 및 이를 포함하는 유기발광소자
KR20180068869A (ko) 유기 발광 소자
KR20200063053A (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
CN110944991B (zh) 杂环化合物及包含其的有机发光器件
CN110546143A (zh) 新型杂环化合物及包含其的有机发光器件
WO2018155826A1 (fr) Nouveau composé et élément électroluminescent organique l&#39;utilisant
KR101994448B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20200052236A (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102003366B1 (ko) 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20170035344A (ko) 신규 화합물 및 이를 포함하는 유기 발광 소자
CN110800122A (zh) 有机电致发光器件
WO2018225943A1 (fr) Nouveau composé et élément électroluminescent organique l&#39;utilisant
KR102288990B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2018139767A9 (fr) Nouveau composé à base d&#39;amine et dispositif électroluminescent organique l&#39;utilisant
CN112334472A (zh) 新型化合物及包含其的有机发光器件
CN112703192A (zh) 新型化合物及包含其的有机发光器件
WO2019054633A1 (fr) Nouveau composé hétérocylique et dispositif électroluminescent organique utilisant celui-ci
KR20190025512A (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR20180104579A (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR101757557B1 (ko) 다환 화합물 및 이를 이용한 유기 전계 발광 소자
KR102022691B1 (ko) 신규한 헤테로 고리 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: 18783784

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: 18783784

Country of ref document: EP

Kind code of ref document: A1