WO2019004614A1 - 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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WO2019004614A1
WO2019004614A1 PCT/KR2018/006168 KR2018006168W WO2019004614A1 WO 2019004614 A1 WO2019004614 A1 WO 2019004614A1 KR 2018006168 W KR2018006168 W KR 2018006168W WO 2019004614 A1 WO2019004614 A1 WO 2019004614A1
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group
compound
formula
layer
light emitting
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차용범
허정오
김연환
전상영
이성재
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주식회사 엘지화학
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Priority claimed from KR1020180059816A external-priority patent/KR102051625B1/ko
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Priority to CN201880021113.6A priority Critical patent/CN110520427B/zh
Publication of WO2019004614A1 publication Critical patent/WO2019004614A1/fr

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    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/20—Spiro-condensed systems
    • 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
    • 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
    • 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
    • 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
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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 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 brightness, 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 in order to improve the efficiency and stability of the organic light emitting device.
  • the organic material layer may include 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. 10-2013- 073537
  • the present invention relates to a novel heterocyclic compound compound and a light emitting device including the same.
  • the present invention provides a compound represented by the following formula (1).
  • 3 &gt is O, S or NR <
  • RTI ID 0.0 &gt
  • R3 &lt / RTI &gt
  • RTI ID 0.0 &gt
  • R3 &lt / RTI &gt
  • RTI ID 0.0 &gt
  • R3 &lt / RTI &gt
  • R ' is hydrogen or a substituted or unsubstituted d-60 alkyl
  • An and Ar 2 are each independently a substituted or unsubstituted C 6 - 60 is a heteroaryl-aryl, or 60 N, a substituted or unsubstituted C comprising one or more of 0, and S 5.
  • the present invention also provides a display device comprising: a first electrode; A second electrode disposed opposite to the first electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is a layer of the above- An organic light-emitting device comprising the compound.
  • the compound represented by the general formula (1) can improve the efficiency, the low driving voltage and / or the lifetime characteristics in the organic light emitting device.
  • the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, 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.
  • the present invention provides a compound represented by the following formula (1).
  • Xi 0, S or N
  • X 2, and 3 ⁇ 4 are each independently N or CR ', and only at least one of which is N,
  • R ' is hydrogen or substituted or unsubstituted alkyl
  • a and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl or a substituted or unsubstituted C 5 -C 60 heteroaryl containing at least one of N, O and S.
  • &quot means a bond connected to another substituent.
  • the substituent to which at least two substituents are connected &quot may be an aryl group, and 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,
  • the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group.
  • 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.
  • the compound may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.
  • 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.
  • 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 number of carbon atoms in the alkyl group is. Lt; / RTI > Another According to the 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 a methyl group, an ethyl group, a propyl group, a n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl tert- Pentyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, n-heptyl, 2-ethylhexyl, 1-methylhexylcyclopentylmethyl, cyclohectylmethyl, octyl, n-octyl, tert-octyl, But are not limited to, ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucleosyl,
  • the alkenyl group may be straight-chain or branched, and the number of carbon
  • 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. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl- 1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl and styrenyl groups.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • 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 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.
  • Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group fluorenyl group and the like.
  • the fluorenyl group may be substituted, and two substituents
  • the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and 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 furane group, a furyl 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, A pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrimidinyl group, a pyrazinopyrany
  • 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.
  • the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.
  • the description of the above-mentioned heterocyclic group can be applied to the heteroaryl among the ' heteroarylamines.
  • the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
  • the description of the aryl groups described above may be applied, except that the arylene is a bivalent.
  • 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 ring may be applied, except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
  • the compound represented by the formula (1) may be a compound represented by any one of the following formulas (1-1) to (1-4).
  • the compound of Formula 1-1 may be any of compounds represented by the following Formulas 1-la to 1-lc.
  • the compound of formula 1-2 is represented by the following formula 1- b. < / RTI >
  • the compound of Formula 1-3 may be any one of the compounds represented by the following Formulas 1- 3a to 1-c.
  • the compound of Formula 1-4 may be a compound represented by the following Formula 1-4a or 1-.
  • a and Ar 2 are each independently selected from the group consisting of
  • the compound represented by the formula (1) can be prepared by the same method as in the following reaction formula (1).
  • the above production method can be more specific in the production example to be described later.
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • 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 layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1, to provide.
  • 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, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And a compound to be displayed.
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
  • the organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1).
  • the electron transporting layer, the electron injecting layer, or the layer which simultaneously injects electrons and transports electrons includes the compound represented by the above formula (1).
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability and has a deep HOMO level of 6.0 eV or more, a high triple energy (ET), and a hole stability.
  • the organic material layer includes a light emitting layer and an electron transporting layer
  • the electron transporting layer may contain a compound represented by the above formula (1).
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, 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.
  • 2 shows an example of an organic light emitting element comprising 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 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 can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
  • 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 organic layer and a second electrode on a substrate.
  • a metal oxide or a metal oxide having conductivity or an alloy thereof may be formed on the substrate using a PVDCphys i cal Vapor Deposition method such as a sputtering method or an e-beam evaporation method To form an anode, and an organic material including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer And then depositing a material which can be used as a cathode thereon.
  • 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 includes 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).
  • 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 conducted to the organic material layer.
  • the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ⁇ 0: ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; There are conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene, polypyrrole and polyaniline, The present invention is not limited thereto.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but the present invention is 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 highest occupied molecular orbital (H0M0) of the hole injecting material be between the work function of the anode material and H0M0 of the surrounding organic layer.
  • the hole injecting material include organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) 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 light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material.
  • a hole transport material Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • 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 compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one 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. Do. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a 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, And has an electron injecting effect from the cathode, an excellent electron injecting effect on the light emitting layer or the light emitting material, preventing migration of the excitons generated in the light emitting layer to the hole injecting layer, .
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like But is not limited thereto.
  • 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 including the compound represented by Formula 1 will be described in detail below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. ≪ Preparation of Intermediate Compound &
  • the compound P-6 (20.0 g, 38.1 mmol) and 2-bromospiro [indole [3,2,1-de] acridine-2, (Aq. K 2 CO 3 ) ((aq. K 2 CO 3 )) was prepared by dispersing 180 ml of tetrahydrofuran in a mixture of tetrahydrofuran and tetrahydrofuran (17.32 g, 34.64 ⁇ ol) 57.2ml, was added to 114.3 ⁇ ol), insert tetrakis triphenyl phosphino palladium [Pd (PPh 3) 4] (1.2g, 3mol%) was refluxed with stirring for 6 hours.
  • I T0 (indium tin oxide) thin film coated with thickness of ⁇ and ⁇ was placed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water which was filtered with a filter of a product manufactured by Mi 11 ipore Co.
  • 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.
  • Hexa nitrile hexaazatri phenyl ene (HAT) of the following chemical formula was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 150 A to form a hole injection layer.
  • an electron blocking layer was formed on the hole transporting layer by vacuum evaporation to a film thickness of 100 A by the following method.
  • BH and BD were vacuum deposited on the electron blocking layer to a thickness of 200 A at an increasing ratio of 25: 1 to form a light emitting layer.
  • the compound [HB 1] was vacuum deposited on the hole transporting layer to a thickness of 50 A on the light emitting layer to form a hole blocking layer.
  • compound ET 1 and compound LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 310 A.
  • the cathode was formed by depositing lithium fluoride (LiF) and aluminum in thickness of 12 ⁇ thick and ⁇ thickness sequentially on the electron injection and transport layer.
  • An organic light emitting device was fabricated in the same manner as in Comparative Experimental Example 1, except that ET 2 and ET 3 were used in place of ET 1 in Comparative Experimental Example 1, as shown in Table 1.
  • T95 means the time required for the luminance to decrease from the initial luminance (1600 nits) to 93 ⁇ 4.
  • Comparative Experimental Example 1-1 instead of using BH and BD as the light emitting layer, the following compounds GH 1 and GD were vacuum deposited at a weight ratio of 20: 1 to a film thickness of 350 A to form a light emitting layer.
  • An organic light emitting device was fabricated in the same manner as in Comparative Experiment Example 2, except that the following GH 2 to GH 4 compounds were used instead of GH 1 in Comparative Experiment Example 2 as shown in Table 1 below.
  • T95 means the time required for the luminance to decrease from the initial luminance (6000 n t) to 95%.
  • the organic light emitting device manufactured using the compound of the present invention as a green light emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.
  • substrate 2 anode

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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un élément électroluminescent organique l'utilisant.
PCT/KR2018/006168 2017-06-30 2018-05-30 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2019004614A1 (fr)

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KR1020180059816A KR102051625B1 (ko) 2017-06-30 2018-05-25 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR10-2018-0059816 2018-05-25

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CN109928960A (zh) * 2019-03-27 2019-06-25 华南理工大学 一种非芳香胺类高激子利用率小分子材料及应用

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KR20170057856A (ko) * 2015-11-17 2017-05-25 주식회사 엘지화학 스피로형 화합물 및 이를 포함하는 유기 발광 소자
KR20170057855A (ko) * 2015-11-17 2017-05-25 주식회사 엘지화학 스피로형 화합물 및 이를 포함하는 유기 발광 소자

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KR20170057856A (ko) * 2015-11-17 2017-05-25 주식회사 엘지화학 스피로형 화합물 및 이를 포함하는 유기 발광 소자
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CN109928960A (zh) * 2019-03-27 2019-06-25 华南理工大学 一种非芳香胺类高激子利用率小分子材料及应用
CN109928960B (zh) * 2019-03-27 2022-05-24 华南理工大学 一种非芳香胺类高激子利用率小分子材料及应用
CN109928945A (zh) * 2019-04-11 2019-06-25 西安欧得光电材料有限公司 一种1-溴二苯并呋喃及其合成方法
CN109928945B (zh) * 2019-04-11 2022-11-04 西安欧得光电材料有限公司 一种1-溴二苯并呋喃及其合成方法

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