WO2019078701A1 - Nouveau composé et dispositif électroluminescent organique le comprenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2019078701A1
WO2019078701A1 PCT/KR2018/012505 KR2018012505W WO2019078701A1 WO 2019078701 A1 WO2019078701 A1 WO 2019078701A1 KR 2018012505 W KR2018012505 W KR 2018012505W WO 2019078701 A1 WO2019078701 A1 WO 2019078701A1
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group
substituted
unsubstituted
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layer
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Korean (ko)
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하재승
김연환
홍완표
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주식회사 엘지화학
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Priority to CN201880052237.0A priority Critical patent/CN111051291A/zh
Publication of WO2019078701A1 publication Critical patent/WO2019078701A1/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
    • H10K85/60—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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • H10K50/15—Hole transporting 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device including the same.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the present invention aims to provide a compound having a low driving voltage and a long lifetime.
  • the present invention also provides an organic light emitting device comprising the compound.
  • An embodiment of the present specification can provide a compound represented by the following formula (1).
  • R1 to R4 each independently represent hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group,
  • Ar2 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group,
  • n, m, o and p are each independently an integer of 0 to 3
  • L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,
  • Ar3 and Ar4 represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or are bonded to each other to form a substituted or unsubstituted ring.
  • one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 have.
  • the compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device, thereby improving the efficiency of the organic light emitting device, and improving the driving voltage and lifetime.
  • the compound according to one embodiment of the present invention can be used as a hole injection, a hole transport, an electron transport and an electron injection or a light emitting material.
  • An embodiment of the present invention provides a compound represented by the above formula (1).
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylamine group; An aralkylamine group; An arylamine group; And an arylphosphine group, or a substituted or unsubstituted one in which at least two of the substituents exemplified above are connected to each other.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with 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 group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it 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.
  • 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 a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl 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.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
  • 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.
  • cyclopropyl cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted monocyclic and polycyclic diaryl Amine group.
  • 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 one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples 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 pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a
  • heterocyclic group in the present specification, the explanation on the above-mentioned heterocyclic group can be applied except that the heterocycle is divalent.
  • the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group and the arylamine group can be applied to the description of the aryl group described above.
  • the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group and the alkylamine group can be applied to the alkyl group described above.
  • alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.
  • aryl group described above can be applied except that arylene is a divalent group.
  • &quot forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.
  • an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.
  • examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.
  • an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom.
  • an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom.
  • the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.
  • X 1 to X 6 are each independently CR or N, and R and R 1 to R 4 are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted or unsubstitute
  • R and R1 through R4 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R and R1 through R4 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R and R1 through R4 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R and R1 through R4 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R and R1 through R4 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 5 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
  • R and R1 through R4 are each independently selected from the group consisting of hydrogen; heavy hydrogen; Methyl group; Or a phenyl group.
  • Arl is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group.
  • Ar1 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms; Or a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms.
  • Ar2 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group.
  • Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms; Or a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms.
  • the aryl group is preferably a phenyl group, a naphthalene group, a phenanthrene group, a fluorene group or a spirobifluorene group,
  • the group is a dibenzofurane group, a dibenzothiophene group or a carbazole group.
  • Ar 1 and Ar 2 are independently substituted or unsubstituted arylamine groups, they are represented by the following formula (2).
  • L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,
  • Ar3 and Ar4 represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or are bonded to each other to form a substituted or unsubstituted ring.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.
  • L is any one of the following formulas.
  • Ar3 and Ar4 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, or may be bonded to each other to form a substituted or unsubstituted ring.
  • Ar3 and Ar4 each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, the aryl group may be a phenyl group, a naphthalene group, a phenanthrene group, a fluorene group or a spirobifluorene group, and the heterocyclic group may be a carbazole group, a dibenzofurane group or a dibenzothi Lt; / RTI >
  • the substituted or unsubstituted ring formed by combining Ar3 and Ar4 with each other is any one of the following formulas.
  • R5 to R9 each independently represent a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer of 0 to 9
  • b to e are each independently an integer of 0 to 8.
  • R5 to R9 each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms.
  • the compounds of the present invention are any of the following formulas:
  • a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 have.
  • 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 generating layer, a hole transporting layer, a hole buffering layer, a light emitting layer, and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a hole generating layer, a hole transporting layer, a hole buffering layer, or a layer that simultaneously generates and transports holes, and the hole generating layer, the hole transporting layer, the hole blocking layer, At the same time, the layer may contain the compound of formula (1).
  • the organic layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.
  • the organic light emitting device of the present invention may have a laminated structure as described below, but is not particularly limited thereto.
  • the first electrode is an electrode for injecting holes.
  • the material of the first electrode may be a material having a large work function so that injection of holes into the organic material layer can be smoothly performed.
  • Specific examples of the cathode material that can be used in the present invention 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); ZnO: Al or SNO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the hole injection layer may serve to smoothly inject holes from the first electrode into the light emitting layer.
  • the hole injection layer may include the compound of Formula 1.
  • the hole injection layer may be composed of only the compound of Formula 1, but the compound of Formula 1 may be present in a state mixed or doped with other hole injection layer materials known in the art.
  • the compound of Formula 1 may account for 100% of the hole injection layer, but it may be doped at 0.1 to 50% by weight.
  • the compound of formula (1) is excellent in electron acceptance, so that power consumption can be improved and driving voltage can be lowered.
  • the thickness of the hole injection layer may be from 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage that the hole injection characteristics can be prevented from being lowered.
  • the thickness is 150 nm or less, the thickness of the hole injection layer is too thick, There is an advantage that it can be prevented from being raised.
  • a hole injection material known in the art can be used.
  • the hole injection layer material in the group consisting of CuPc (cupper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl- Any one or more selected may be used, but the present invention is not limited thereto.
  • the hole transport layer can play a role of facilitating the transport of holes.
  • the hole transport layer may contain the compound of the above formula (1).
  • the hole transport layer may be composed of only the compound of Formula 1, but the compound of Formula 1 may be present in a state mixed or doped with other hole transport layer materials known in the art.
  • the compound of Formula 1 may account for 100% of the hole transporting layer, but it may be doped at 0.1 to 50% by weight.
  • As the hole transport layer material a hole transport material known in the art can be used.
  • the hole-transporting layer may be formed of NPD (N, N-dinaphthyl-N, N'-diphenylbenzidine), TPD (N, N'- s-TAD, and MTDATA (4,4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) -triphenylamine), but the present invention is not limited thereto.
  • the hole transport layer material it is possible to use, as a hole transport layer material, a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative and a pyrazolone derivative, a phenylene diamine derivative, an arylamine derivative, Stilbene derivatives, silazane derivatives, polysilane-based compounds, aniline-based copolymers, conductive polymeric oligomers (particularly thiophenol oligomers), and the like.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer.
  • the hole buffer layer may include the compound of Formula 1, and may include a hole injecting or transporting material known in the art.
  • the hole blocking layer may be composed of only the compound of Formula 1, but the compound of Formula 1 may be mixed or doped with other host materials.
  • An electron blocking layer may be provided between the hole transporting layer and the light emitting layer, and the compound of Formula 1 or a material known in the art may be used.
  • the light emitting layer may emit red, green, and / or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting layer material may be those known in the art.
  • CBP carboxyphenyl
  • mCP carbazol-9-yl
  • the luminescent dopant may include PIQIR (acac) bis (1-phenylisoquinoline) acetylacetonate iridium, PQIr acac bis (1-phenylquinoline) acetylacetonate iridium, PQIr (tris (1-phenylquinoline) a phosphorescent material such as iridium and PtOEP, or a fluorescent material such as Alq3 (tris (8-hydroxyquinolino) aluminum) may be used.
  • PIQIR acac bis (1-phenylisoquinoline) acetylacetonate iridium
  • PQIr acac bis (1-phenylquinoline) acetylacetonate iridium PQIr (tris (1-phenylquinoline) a phosphorescent material such as iridium and PtOEP, or a fluorescent material such as Alq3 (tris (8-hydroxyquinolino) aluminum)
  • a fluorescent substance such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or Alq3 (tris (8-hydroxyquinolino) aluminum) may be used as the luminescent dopant
  • Ir (ppy) 3 fac tris (2-phenylpyridine) iridium
  • Alq3 tris (8-hydroxyquinolino) aluminum
  • the light emitting dopant may be a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, a spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene ), A PFO-based polymer, and a PPV-based polymer may be used, but the present invention is not limited thereto.
  • a hole blocking layer may be provided between the electron transporting layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer can play a role in facilitating the transport of electrons.
  • Materials known in the art such as Alq3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq can be used.
  • the thickness of the electron transporting layer may be 1 to 50 nm.
  • the thickness of the electron transporting layer is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered.
  • the thickness is 50 nm or less, the thickness of the electron transporting layer is too thick to increase the driving voltage There is an advantage that it can be prevented.
  • the electron injection layer may serve to smoothly inject electrons.
  • Alq3 tris (8-hydroxyquinolino) aluminum
  • PBD polydimethyl methacrylate
  • TAZ tris (8-hydroxyquinolino
  • spiro-PBD BAlq or SAlq.
  • Metal compounds include metal halides, and storage can be used, for example, can be used LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2, MgF 2, CaF 2, SrF 2, BaF 2 and RaF 2 and the like.
  • the thickness of the electron injection layer may be 1 to 50 nm. If the thickness of the electron injection layer is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from being degraded. If the thickness is 50 nm or less, the thickness of the electron injection layer is too thick, There is an advantage that it can be prevented from being raised.
  • the second electrode is an electron injection electrode, and may be a material having a small work function to facilitate injection of electrons 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 are not limited thereto.
  • the organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).
  • the organic layers may be formed of the same material or different materials.
  • the organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of Formula 1, that is, the compound represented by Formula 1.
  • the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material 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
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode
  • an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon depositing a material usable 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 of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode may be an anode and the second electrode may be a cathode.
  • the first electrode may be a cathode and the second electrode may be a cathode.
  • the hole injecting material is a layer for injecting holes from the electrode.
  • the hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material.
  • a compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable.
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the 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.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • 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.
  • Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • Specific examples of the 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 examples 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex examples include iridium complex, platinum complex, and the like, but are not limited thereto.
  • the electron transporting material 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. Is suitable. Specific examples include an Al 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.
  • an example of 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.
  • Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- 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 according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • Compound A3 was synthesized by the same method except for using 4-bromofluorene instead of 2-bromofluorene in the synthesis of A1 above
  • Compound A6 was synthesized by the same method except for using 5-methylnaphthalene instead of 1-naphthol in the synthesis of A2 above
  • Compound A7 was synthesized by the same method except for using 7-methylnaphthalene instead of 1-naphthol in the synthesis of A3 above
  • 2-M potassium carbonate aqueous solution (100 ml) was added to 4-bromo-1-naphthol (20 g, 89.6 mmol) and phenylboronic Triphenylphosphino palladium (2.07 g, 2 mol%) was added thereto, followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate aqueous solution was removed to separate layers. After removing the solvent, the white solid was recrystallized from ethyl acetate and hexane to obtain the above compound a-1 (17.76 g, yield 90%).
  • B2 was synthesized by the same method except that 3-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid in the synthesis of B1
  • B3 was synthesized by the same method except for using 2-chlorophenylboronic acid instead of 4-chlorophenylboronic acid in the synthesis of B1
  • C1 was synthesized by the same method except that A2 was used instead of A1 in the synthesis of B1
  • C2 was synthesized in the same manner as in the synthesis of C1 except that 2-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid
  • C3 was synthesized by the same method except that A2 was used instead of A1 in the synthesis of B4
  • D1 was synthesized by the same method except that A3 was used instead of A1 in the synthesis of B1
  • D2 was synthesized by the same method except that 3-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid in the synthesis of D1
  • D3 was synthesized by the same method except for using 2-chlorophenylboronic acid instead of 4-chlorophenylboronic acid in the synthesis of D1
  • D4 was synthesized by the same method except that A3 was used instead of A1 in the synthesis of B4
  • E1 was synthesized in the same manner as in the synthesis of B1 except that 3'-chloro [1,1'-biphenyl] -3-ylboronic acid was used instead of 4-chlorophenylboronic acid
  • F1 was synthesized by the same method except that A7 was used instead of A1 in the synthesis of B1
  • F2 was synthesized by the same method except that A8 was used instead of A1 in the synthesis of B3 above
  • Biphenyl] -4-yl) amine 22.04, 68.58 mmol
  • sodium-t-butoxide 9.69 g, 100.8 mmol
  • [bis (tri-t-butylphosphine)] palladium 687 mg, 2 mmol%) was added.
  • b-1 26.49 g, 85% was prepared by recrystallization using tetrahydrofuran and ethyl acetate.
  • D-2 was prepared by the same method except for using d-1 instead of b-1 in the synthesis of b-2
  • Bromo-2-chloro-6-fluorobenzene (47.83 g, 228.3 mmol) was added to tetrahydrofuran (200 ml) and 2M potassium carbonate aqueous solution (Tri (t-butylphosphine) palladium (554 mg, 0.5 mol%) was added thereto, and the mixture was heated with stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate aqueous solution was removed to separate layers. After removal of the solvent, the white solid was recrystallized from hexane and ethanol to give the above compound e-1 (36.3 g, yield 75%).
  • e-1 (30 g, 134.7 mmol) was added to DMF (200 ml) and dissolved. NBS (24.22 g, 136.0 mmol) was slowly added dropwise at 0 ° C and the mixture was stirred at room temperature for 3 hours. After extraction with water and ethyl acetate at room temperature, the white solid was recrystallized from hexane and ethanol to give the above compound e-2 (34.52 g, yield, 85%).
  • e-2 (25 g, 82.9 mmol) was added to DMF (200 ml), potassium carbonate (17.18 g, 124.3 mmol) was added and the mixture was heated to reflux and stirred for 2 hours. After completion of the reaction, the reaction mixture was extracted with water and ethyl acetate, and the white solid was recrystallized from hexane and ethanol to obtain the above compound e-3 (16.3 g, yield, 87%).
  • Compound B4-1 was prepared by synthesizing B3-1 in the same manner except that B4 was used instead of B3 and 4-bromo-N-phenylamine was used instead of 3-bromo-N-phenylamine
  • Compound C3-1 was synthesized in the same manner as B3-1 except that C3 was used instead of B3 and 4-bromo-N-phenylamine was used instead of 3-bromo-N-phenylamine
  • Compound 12 was synthesized in the same manner as Compound 10, except that 5'-bromo-1,1 ': 3', 1'-terphenyl was used instead of 2-bromodibenzofuran
  • Compound 14 was prepared by the same method except that B4-2 was used instead of B4-1 and 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromodibenzofuran in the synthesis of Compound 10 And
  • Compound 18 was synthesized in the same manner as Compound 10, except that C3-1 was used instead of B4-1 and 9-bromophenanthrene was used instead of 2-bromodibenzofuran
  • the compound 18 was synthesized in the same manner as in the synthesis of the compound 18, except that 4-bromo-9,9-diphenyl-9H-fluorene was used instead of 9-bromophenanthrene
  • Compound 21 was synthesized in the same manner as in the synthesis of Compound 18, except that 2-bromo-9,9-diphenyl-9H-fluorene was used instead of 9-bromophenanthrene.
  • Compound A3 was used instead of A1 in the synthesis of B1, but instead of 4-chlorophenylboronic acid, 9-phenyl-9H-carbazol-2-yl) boronic acid was used to synthesize Compound 26 .
  • E2 was used instead of E1 in the synthesis of Compound 30, and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine was used in place of di [(1,1'- biphenyl] , The compound 31 was prepared.
  • Compound 32 was prepared by the same method as Compound 26 except that B4 was used instead of A3 and b-2 was used in place of (9-phenyl-9H-carbazol-2-yl) boronic acid.
  • Compound 33 was prepared by the same method except for using c-2 in place of b-2 in the synthesis of the compound 32.
  • Compound 33 was prepared by the same method except for using d-3 in place of b-2 in the synthesis of the compound 32.
  • Compound 42 was synthesized in the same manner as Compound 35 except that F1 was used instead of B3-2 and diphenylamine was used instead of 2-bromodibenzothiophene.
  • Compound 44 was synthesized in the same manner as Compound 39 except that A9 was used instead of F1-1 and diphenylamine was used instead of 4-bromo-9,9-diphenyl-9H-fluorene.
  • Compound 45 was synthesized by the same method except that A9 was used instead of A6 in the synthesis of the compound 41.
  • Compound A9 was synthesized in the same manner as Compound 41 except that 9-phenyl-9H-carbazol-3-yl) boronic acid was used in place of diphenylamine to prepare Compound 46.
  • the compound 41 was synthesized in the same manner as in the synthesis of the compound 41 except that A9 was used instead of A6, and (4- (9H-carbazol-9-yl) phenyl) boronic acid was used instead of diphenylamine.
  • Compound A9 was synthesized in the same manner as Compound 41 except that 4- (9H-carbazol-9-yl) phenyl) boronic acid was used instead of diphenylamine.
  • Compound 48 was prepared.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 ⁇ was immersed in distilled water containing a dispersing agent 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. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 ⁇ to form a hole injection layer.
  • a host H1 and a dopant D1 compound (25: 1, weight ratio) were vacuum deposited as a compound luminescent layer to a thickness of 300 ⁇ .
  • an E1 compound 300 ANGSTROM was sequentially vacuum-deposited by electron injection and transport layer.
  • Lithium fluoride (LiF) having a thickness of 12 ⁇ and aluminum having a thickness of 2,000 ⁇ were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the deposition rate of lithium fluoride was 0.2 ⁇ / sec
  • the deposition rate of aluminum was 3 to 7 ⁇ / sec.
  • Table 1 shows the results of the organic light emitting device manufactured by using each compound as a hole transporting layer material as in Examples 1 to 10 and Comparative Examples 1 to 3.
  • Comparative Example 1 is a benzidine type material.
  • characteristics such as low voltage and high efficiency are exhibited as described above by bringing about chemical stability and triplet energy increase with a cured structure by using a xanthene structure which is more structurally more structurally than the xanthan type Comparative Example 2 .
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 ⁇ was immersed in distilled water containing a dispersing agent 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. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 ⁇ to form a hole injection layer.
  • HT1 300 ANGSTROM
  • Compound 3 synthesized in Preparation Example 7 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form a hole control layer.
  • a host H1 and a dopant D1 compound (25: 1, weight ratio) were vacuum deposited as a compound luminescent layer to a thickness of 300 ⁇ .
  • an E1 compound (300 ANGSTROM) was sequentially vacuum-deposited by electron injection and transport layer.
  • Lithium fluoride (LiF) having a thickness of 12 ⁇ and aluminum having a thickness of 2,000 ⁇ were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the deposition rate of lithium fluoride was 0.2 ⁇ / sec
  • the deposition rate of aluminum was 3 to 7 ⁇ / sec.
  • the compound represented by the chemical formula according to the present invention can function as a hole transporting and hole controlling in an organic electronic device including an organic light emitting device, and the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and stability.

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2018/012505 2017-10-20 2018-10-22 Nouveau composé et dispositif électroluminescent organique le comprenant WO2019078701A1 (fr)

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WO2023162947A1 (fr) * 2022-02-25 2023-08-31 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique

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CN112409315B (zh) * 2020-11-12 2023-03-28 广东工业大学 一种含有螺芴功能基团的二胺单体及其制备方法、低介电常数的聚酰亚胺
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