WO2019078443A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2019078443A1
WO2019078443A1 PCT/KR2018/006423 KR2018006423W WO2019078443A1 WO 2019078443 A1 WO2019078443 A1 WO 2019078443A1 KR 2018006423 W KR2018006423 W KR 2018006423W WO 2019078443 A1 WO2019078443 A1 WO 2019078443A1
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Prior art keywords
oav
czl7900
8lozam
6ϊοζ
compound
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PCT/KR2018/006423
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English (en)
Korean (ko)
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하재승
김연환
이성재
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주식회사 엘지화학
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Priority claimed from KR1020180062161A external-priority patent/KR102109789B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880018312.1A priority Critical patent/CN110494430B/zh
Publication of WO2019078443A1 publication Critical patent/WO2019078443A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • 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. 10-2000-0051826
  • the present invention relates to a novel amine compound and an organic light emitting device comprising the same.
  • the present invention is a.
  • a, c, d and e are an integer of 0 to 3
  • b is an integer of 0 to 2
  • X 1 or 2
  • R 1 to R 4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 60 alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ( 60 thioalkyl, substituted or unsubstituted C 3 - 60 cycloalkyl, substituted or Unsubstituted C 6 -60 aryl, or tri (d-60 alkyl) silyl,
  • R are each independently represented by the following formula
  • An and Ar 2 are each C independently represents a substituted or unsubstituted 6-60 aryl; Or substituted or unsubstituted C 2 -C 60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O, and S.
  • the present invention also provides a display device comprising: a first electrode; A second electrode facing the first electrode; And at least one organic material layer sandwiched between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.
  • the compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of 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.
  • FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is good.
  • the present invention provides a compound represented by the above formula (1).
  • substituted or unsubstituted &quot refers to a substituent selected from the group consisting of deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, An aryloxy group, an aryloxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, An arylamine group, an arylphosphine group, or a heterocyclic group containing at least one of N, O and S atoms, or may be substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms, or may be substituted or unsubstituted with at least one substituent selected
  • 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. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • a silyl group is a silyl group.
  • Specific examples include 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 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- Pentyl, neopentyl, tert-pentyl, n-butyl, 1-methylpentyl, 2-methylpentyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, 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 preferably has 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. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, , 4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
  • 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to the monocyclic state, the number of carbon atoms of the aryl group is 6 to 20. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like.
  • 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 and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, And the like.
  • the present invention is not limited thereto.
  • 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 furan group, a pyrrolyl 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 pyridazinyl group, an isoquinoline group, an indole group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, A benzofuranyl group, a phenanthroline group, an isoxazolyl group, an isoxazolyl
  • 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 heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.
  • 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 hydrocarbon ring is not a monovalent hydrocarbon ring, and the hydrocarbon ring is not a monovalent hydrocarbon ring, Can be applied.
  • 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.
  • Formula 1 is represented by Formula 1-1, 1-2, or 1-3 according to the bonding position of Formula 2, respectively.
  • the silver is selected from the group consisting of a single bond, phenylene biphenyl diyl, terphenyl diyl, quaterphenyl diyl, naphthalenediyl anthracenediyl, phenanthrenediyl, triphenylene diyl, pyrandiyl, dimethylfluorenediyl, methylphenylfluorenediyl, di Phenylfluorenediyl, dibenzofuranediyl, dibenzothiophenediyl, carbazolyl, or 9-phenyl-9H-carbazolyl.
  • L1 is a single bond, or phenylene.
  • L < 2 > and L < 3 &gt are each independently selected from the group consisting of a single bond, phenylene, biphenyl diyl, terphenyl diyl, quaterphenyl diyl, naphthalenediyl, anthracenediyl, phenanthrenyl, triphenylene diyl, Phenyl-9H-carbazolyl, fluorenylidene, methylphenylfluorenediyl, diphenylfluorenediyl, spirofluorenediyl, dibenzofuranediyl, dibenzothiophenediyl, carbazolyl, or 9-phenyl-9H-carbazolyl.
  • a and Ar 2 are each independently phenyl, biphenylyl, terphenyl reel, quarter-biphenylyl, naphthyl, phenanthryl waste carbonyl, dimethyl-fluorenyl, dibenzofuran fluorenyl, spiro fluorenyl. Dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenyl-9H-carbazolyl. Representative examples of the compound represented by the above formula (1) are as follows: II
  • CZl7900 / 8lOZaM / X3d ⁇ »8ZD ⁇ 0 / 6 ⁇ OAV Can be prepared by the same production method as in the above-mentioned formula (1), and the compounds represented by the other formulas (1-2) and (1-3) can also be applied.
  • the above Reaction Scheme 1 is an amine substitution reaction, which is a reaction to produce the compound represented by Formula 1-1 by counterion of the compound represented by Formula 1-a and the compound represented by Formula 1-b.
  • the reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reaction for the amine-substituted reaction can be varied as is known in the art.
  • X is halogen (more preferably bromo, or chloro).
  • 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 facing 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 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, 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 hole injecting and transporting hole, 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 compound according to the present invention can be used as a diskette of a light emitting layer.
  • 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 transports electrons and injects electrons includes the compound represented by the above formula (1).
  • the organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general 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.
  • the compound represented by Formula 1 shows an example of an organic light emitting element 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 injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting 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 layer may be formed of the same material or another material.
  • the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate.
  • a PVD (Physical Vapor Deposition) method such as a sputtering method or an e-beam evaporation method is used to deposit a metal or a conductive metal oxide or an alloy thereof A hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a substance usable as a cathode is deposited 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 refers to spin coating, dip coating, doctor blading, inkjet printing screen printing, spraying, coating, and the like, but is not limited thereto.
  • a method of forming an organic material layer from a cathode material The organic light emitting device can be manufactured by sequentially depositing the material (WO 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the second electrode is a cathode
  • 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; Poly (3 ⁇ methylthiophene), poly [3, 4- (ethylene-1, 2-dioxy) thiophene KPEDOT), but a conductive polymer such as a polyester and blood and polyaniline, but are not limited thereto eu
  • 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 Li / 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. It is preferable that the HOMO concentration of the hole injecting material is 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 material, A quinacridone-based organic material, a perylene-based organic material, an anthraquinone, a polyaniline-based material, and a polythiophene-based conductive polymer. It is not.
  • 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 containing 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, 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 derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherane having an arylamino group.
  • styrylamine compound include substituted or unsubstituted A compound in which at least one aryl vinyl group is substituted with an arylamine, 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 metal complexes include iridium complexes and platinum complexes, but are not limited thereto.
  • 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.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10- (2-methyl-8-quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium (0-cresolato) gallium, bis But are not limited thereto.
  • the organic light emitting device according to the present invention 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 compound Al-2 (30 g, 65.5 mg ol) was added to 2M sodium hydroxide solution and stabilized at 0 ° C. Then, hydrogen peroxide (25 ml, 131.18 mmol) was added with stirring to complete the reaction. After completion of the reaction, water was added thereto, stirred for 30 minutes, and then cooled to room temperature to prepare the compound Al-3 (18.28 g, yield 80%).
  • the compound B-1-4 was prepared by separating into a column.
  • Compound B-1 was prepared in the same manner as in the production of Compound B-1, except that 1, 4-dichloro-2,3-difluorobenzene was used in place of 4-bromo-1,2-difluorobenzene. 1-6.
  • Compound A1 was obtained in the same manner as in the production of Compound B-1-1, except that Compound A-1-3 was used in place of Compound A-3, 4-dihydroxy-9H-fluoren- .
  • Compound A1 was prepared in the same manner as in the preparation of Compound B-1-2, except that Compound A-1-3 was used instead of 3, 4-dihydroxy-9H-fluoren-9-one.
  • Compound B-1-3 was prepared in the same manner as Compound B-1 except that Compound A-1 was replaced with Compound A-1 in place of 3, 4-dihydroxy-9H-
  • Compound A4 was prepared in the same manner as in the preparation of Compound B-1-4, except that Compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.
  • Compound A5 was prepared in the same manner as in the preparation of Compound B-1-5, except that Compound A-1-3 was used instead of Compound A-3, 4-dihydroxy-9H-fluorene-9-.
  • Compound A6 was synthesized in the same manner as in the preparation of Compound B-1-6, except that Compound A-1-3 was used in place of Compound A- 1-3, 4-dihydroxy-9H-fluoren- .
  • Compound B2 was prepared in the same manner as in the preparation of B1.
  • Compound B3 was prepared in the same manner as in the preparation of B1.
  • Compound B4 was prepared in the same manner as in the preparation of compound B1, except that B? 1? 4 was used instead of compound B-1-1.
  • Compound B5 was prepared in the same manner as in the preparation of Compound B1, except that B-1-5 was used instead of Compound B-1-1.
  • compound A3 was used, and instead of ([1,1'-diphenyl] -2-yl) -9,9-dimethyl- Fluorene-2-amine was used in place of the compound 3, to thereby prepare the compound 3.
  • Compound 9 was prepared in the same manner as in the preparation of Compound 1, except that Compound B1 was used instead of Compound A1.
  • Compound C1 was used instead of Compound A1 in the preparation of Compound 1, and N-phenyl- [1,1'-biphenyl] -2-amine (Compound , Compound 15 was prepared in the same manner as Compound 1 was prepared.
  • the ⁇ (indium tin oxide) is 1,000 A glass substrate (corning 7059 glass) kotang thin film to a thickness, into a dispersing agent dissolved in distilled water and washed with ultrasonic waves.
  • the detergent was a product of Fischer Co., Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. ITO was washed for 30 minutes and then ultrasonically washed for 2 minutes with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
  • the following HAT compound was thermally vacuum deposited to a thickness of 500 A on the thus prepared " t " transparent electrode to form a hole injection layer.
  • the compound K900A prepared above which is a material for transporting holes, was vacuum-deposited on the hole transport layer, and then the HT2 compound was vacuum-deposited to a film thickness of 50 A on the hole transport layer to form a hole control layer.
  • the following HI compound (host) and the following D1 compound (dopant) were vacuum deposited on the hole-transporting layer at a weight ratio of 25: 1 to form a 300 A thick light emitting layer.
  • Lithium fluoride (LiF) 12 A thick and aluminum 2,000 A thick were sequentially deposited on the electron transport layer to form a cathode
  • HT1, HT3 and HT4 are as follows.
  • the lifetime is defined as the time required for the luminance to decrease to 95% when the initial luminance is set to 100%.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was immersed in distilled water dissolved in a dispersant and washed with ultrasonic waves.
  • the detergent was a product of Fischer Co.
  • the distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used.
  • the following HAT compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer.
  • the following compound (900A), which is a material for transporting holes, was vacuum-deposited on the hole transport layer, and then the compound 1 prepared above was vacuum-deposited to a film thickness of 50 A on the hole transport layer to form a hole control layer.
  • the following HI compound (host) and the following D1 compound (dopant) were vacuum deposited on the hole-transporting layer at a weight ratio of 25: 1 to form a 300 A thick light emitting layer.
  • Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2,000 A were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.
  • the lifetime is defined as the time required for the luminance to decrease to 95% when the initial luminance is set to 100%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2018/006423 2017-10-19 2018-06-05 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2019078443A1 (fr)

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KR10-2017-0135923 2017-10-19
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KR10-2018-0062161 2018-05-30
KR1020180062161A KR102109789B1 (ko) 2017-10-19 2018-05-30 신규한 화합물 및 이를 이용한 유기발광 소자

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WO2021120838A1 (fr) * 2019-12-19 2021-06-24 陕西莱特光电材料股份有限公司 Composé organique, dispositif électronique et appareil électronique
CN111004207A (zh) * 2019-12-19 2020-04-14 陕西莱特光电材料股份有限公司 有机化合物、电子器件及电子装置
CN112010866A (zh) * 2020-09-07 2020-12-01 京东方科技集团股份有限公司 二恶英类化合物及其制备方法和应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140015226A (ko) * 2013-12-19 2014-02-06 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20150117130A (ko) * 2014-04-09 2015-10-19 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2016131521A1 (fr) * 2015-02-16 2016-08-25 Merck Patent Gmbh Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques
KR20170026813A (ko) * 2015-08-28 2017-03-09 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20170076117A (ko) * 2015-12-24 2017-07-04 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140015226A (ko) * 2013-12-19 2014-02-06 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20150117130A (ko) * 2014-04-09 2015-10-19 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2016131521A1 (fr) * 2015-02-16 2016-08-25 Merck Patent Gmbh Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques
KR20170026813A (ko) * 2015-08-28 2017-03-09 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR20170076117A (ko) * 2015-12-24 2017-07-04 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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