WO2019108033A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2019108033A1
WO2019108033A1 PCT/KR2018/015125 KR2018015125W WO2019108033A1 WO 2019108033 A1 WO2019108033 A1 WO 2019108033A1 KR 2018015125 W KR2018015125 W KR 2018015125W WO 2019108033 A1 WO2019108033 A1 WO 2019108033A1
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group
substituted
unsubstituted
compound
layer
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PCT/KR2018/015125
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English (en)
French (fr)
Korean (ko)
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하재승
김연환
윤주용
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주식회사 엘지화학
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Priority to CN201880035812.6A priority Critical patent/CN110740998B/zh
Publication of WO2019108033A1 publication Critical patent/WO2019108033A1/ko

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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
    • H10K85/649—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • 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]
    • H10K50/11—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]
    • H10K50/14—Carrier 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
    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a 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).
  • X1 and X2 are each independently O or S,
  • R1 to R3 each independently represent hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a and b are each independently an integer of 0 to 4,
  • c is an integer of 1 to 4,
  • At least one of R < 3 > is represented by the following formula (2)
  • L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n is an integer of 0 to 3
  • Adjacent groups among Ar1, Ar2 and L may combine with each other to form a 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 injecting or hole transporting material.
  • An embodiment of the present invention provides a compound represented by the above formula (1).
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; Cyano; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy 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 silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or
  • 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 may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different and each independently hydrogen; heavy hydrogen; halogen; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • Specific examples include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
  • 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.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.
  • the amine group is -NH 2 ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
  • the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group can be applied to the alkyl group described above.
  • Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group.
  • the alkylsulfoxy group include a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
  • 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
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
  • the "ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
  • the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
  • the hetero ring includes one or more non-carbon atoms and hetero atoms.
  • the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the examples of the heterocyclic group except that the heterocyclic group is not monovalent.
  • 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.
  • the aromatic hydrocarbon ring is a divalent group.
  • 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 and X 2 are each independently 0 or S.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted silyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
  • Ar1 and Ar2 each independently represent a fluorene group substituted with at least one of a phenyl group and a methyl group, an alkyl group substituted or unsubstituted with at least one aryl group, a naphthylene group, a carbazole group, A dibenzofurane group, a dibenzothiophene group, or a phenyl group substituted or unsubstituted with a spirobifluorene group; A biphenyl group substituted or unsubstituted with a silyl group or a carbazole group substituted or unsubstituted with at least one of an alkyl group, a phenyl group, an aryl group or alkyl, substituted or unsubstituted with an aryl group; A terphenyl group substituted or unsubstituted with a phenyl group; A naphthalene group substituted or unsubstituted with a
  • n when n is 0, it is a direct bond.
  • n 2 or more
  • the substituents in parentheses are the same or different from each other.
  • L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
  • L is any one of the following formulas.
  • A1 to A3 each independently represent a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a1 to a3 each represent an integer of 0 to 3
  • the ring formed by bonding adjacent groups of Ar1, Ar2 and L to each other is any one of the following formulas.
  • R5 to R16 each independently represent a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • d is an integer of 0 to 9
  • e to h are each independently an integer of 0 to 8
  • i is an integer of 0 to 3
  • j is an integer of 0 to 6
  • the formula (1) may be represented by any of the following formulas (3) to (6).
  • R1, R2, R3, X1, X2, a and b are as described above.
  • 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 injecting layer may include the compound of Formula 1 above.
  • 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 the formula (1) is a derivative having an indenofluorene structure, and has excellent electron-accepting ability, so that power consumption can be improved and the driving voltage can be lowered.
  • the thickness of the hole injection layer may be 1 to 150 nm.
  • 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. If 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. For example, 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.
  • hole transporting materials hole transporting materials 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 hole injection or transport materials 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 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 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 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 the 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 B2 was synthesized in the same manner as in the synthesis of B1 except that 1-bromo-2,3-difluorobenzene was used instead of 4-bromo-1,2-difluorobenzene.
  • Compound B3 was synthesized in the same manner as in the synthesis of B1 except that 1,2-dichloro-4,5-difluorobenzene was used instead of 4-bromo-1,2-difluorobenzene.
  • Compound B4 was synthesized in the same manner as in the synthesis of B1 except that 1,4-dichloro-2,3-difluorobenzene was used instead of 4-bromo-1,2-difluorobenzene.
  • Compound C2 was synthesized in the same manner except that 3-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid in the synthesis of C1.
  • Compound C3 was synthesized in the same manner except that 2-chlorophenylboronic acid was used in place of 4-chlorophenylboronic acid in the synthesis of C1.
  • Compound C6 was synthesized by the same method except that B2 was used in place of B1 in the synthesis of C4.
  • Compound D2 was synthesized in the same manner as in the synthesis of C1 except that C6 was used instead of B1 and 8-bromo-1-chlorobenzo [b, d] furan was used instead of 4-chlorophenylboronic acid.
  • Compound 5 was prepared by the same method except that B2 was used in place of B1 in the synthesis of Compound 3 above.
  • Compound 10 was prepared by the same method except for using C4 instead of B1 and E2 instead of 4-chlorophenylboronic acid in the synthesis of C1.
  • 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) were vacuum deposited to a thickness of 300 ⁇ as a compound light emitting layer.
  • an E1 compound (300 ⁇ ) was deposited in a 1: 1 ratio with LiQ, followed by thermal vacuum deposition with electron injection and transport layers.
  • 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 experiments of the organic light emitting devices manufactured using the respective compounds as the hole transporting layer materials as in Examples 1 to 7 and Comparative Examples 1 to 4.
  • 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 900 ⁇
  • Compound 1 synthesized in Production Example 3 was vacuum deposited on the hole transport layer to a film thickness of 50 ⁇ to form a hole control layer.
  • a host H1 and a dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 ⁇ as a compound light emitting layer.
  • an E1 compound 300 ANGSTROM
  • 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.
  • Example 8 The same experiment was carried out as in Example 8 except that Compound 5 was used instead of Compound 1 as the hole-adjusting layer.
  • Example 8 HT3 was used instead of HT1 as the hole transport layer, and HT5 was used in place of the compound 1 as the hole control layer.
  • Table 2 shows the results of the organic light emitting device manufactured using the respective compounds as the hole control layer materials as in Examples 8 to 17 and Comparative Examples 5 to 8.
  • Example 20 mA / cm 2 Hole transport layer The hole- Voltage (V) (@ 20 mA / cm 2 ) Cd / A (@ 20 mA / cm 2 ) The color coordinates (x, y) Life (T95, h) (@ 20 mA / cm 2 )
  • Example 8 HT1 Compound 1 3.33 6.89 (0.135, 0.138) 52.0
  • Example 9 HT1 Compound 3 3.52 6.79 (0.134, 0.138) 48.0
  • Example 10 HT1 Compound 5 3.44 6.67 (0.134, 0.138) 46.8
  • Example 11 HT1 Compound 6 3.45 6.58 (0.137, 0.134) 47.1
  • Example 12 HT1 Compound 7 3.52 6.87 (0.138, 0.138) 42.5
  • Example 13 HT1 Compound 8 3.38 6.82 (0.135, 0.139) 46.5
  • Example 14 HT1 Compound 9 3.39 6.81 (0.135, 0.138) 49.7
  • Example 15 HT1 Compound 10 3.
  • 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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