WO2022154282A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2022154282A1
WO2022154282A1 PCT/KR2021/019198 KR2021019198W WO2022154282A1 WO 2022154282 A1 WO2022154282 A1 WO 2022154282A1 KR 2021019198 W KR2021019198 W KR 2021019198W WO 2022154282 A1 WO2022154282 A1 WO 2022154282A1
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group
substituted
unsubstituted
layer
compound
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Korean (ko)
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차용범
이성재
홍성길
이형진
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주식회사 엘지화학
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Priority to CN202180076969.5A priority Critical patent/CN116457350A/en
Publication of WO2022154282A1 publication Critical patent/WO2022154282A1/en

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    • H—ELECTRICITY
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    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • 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
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • 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
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    • 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
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    • 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
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    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting diode has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers, if necessary.
  • hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. can be divided into
  • the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
  • an electron injection material or an electron transport material an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used.
  • the light emitting layer material a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed A material with high luminous efficiency that converts it into light when it is formed is preferable.
  • the present specification provides a compound and an organic light emitting device comprising the same.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,
  • b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,
  • r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.
  • an exemplary embodiment of the present specification includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.
  • the driving voltage of the device is lowered, the efficiency of the device is increased, and the lifespan is prolonged.
  • 1 to 3 illustrate an organic light emitting diode according to an exemplary embodiment of the present specification.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,
  • b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,
  • r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.
  • the compound of Formula 1 is characterized in that when the carbon number of the naphthalene group is referred to as follows, carbon 1 is substituted with a carbazole group and carbon 2 is substituted with an amine group.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and two or more When substituted, two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; cyano group (-CN); amine group; alkoxy group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl,
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, such as 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a fluoranthene group, etc.
  • the present invention is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heterocyclic group includes atoms other than carbon and one or more heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, S and P, and the like.
  • the number of carbon atoms is not particularly limited, but preferably has 1 to 50 carbon atoms, further preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • the heterocyclic group may be an aromatic ring, an aliphatic ring, and a ring condensed therewith.
  • heterocyclic group examples include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocar
  • the heteroaryl group is an aromatic ring group containing one or more atoms other than carbon and heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S.
  • the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S.
  • carbon number is not specifically limited, It is preferable that carbon number is 2-60.
  • the heteroaryl group has 2 to 30 carbon atoms. Examples of the heteroaryl group may be selected from the examples of the heterocyclic group.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto.
  • the amine group is -NH 2 ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30.
  • the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group.
  • diphenylamine group diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group and the aryl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the aryl group described above.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 1 to 50 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; or deuterium.
  • R1 and R2 are each hydrogen.
  • a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other.
  • R1 is hydrogen, and a is 4.
  • b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other.
  • R2 is hydrogen
  • b is 4.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; terphenylene group; or a naphthylene group.
  • L3 is a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L3 is a direct bond; phenylene group; or a biphenylene group.
  • L3 is a phenylene group; or a biphenylene group.
  • L3 is a biphenylene group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group, an aryl group, and one or more substituted or unsubstituted aryl groups selected from the group consisting of a heterocycle; Or an alkyl group, an aryl group, and one or more unsubstituted heterocyclic groups selected from the group consisting of heterocyclic groups.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group substituted or unsubstituted with an alkyl group or an aryl group; or a heterocyclic group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; terphenyl group unsubstituted or substituted with an aryl group; a naphthyl group unsubstituted or substituted with an aryl group; a phenanthrene group unsubstituted or substituted with an aryl group; a triphenylene group unsubstituted or substituted with an aryl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; a carbazole group unsubstituted or substituted with an aryl group; a dibenzofuran group unsubstituted or substituted with an aryl group; Or a dibenzothiophene group un
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group or a phenanthrene group; biphenyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a phenyl group or a biphenyl group; phenanthrene group; triphenylene group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; carbazole group; dibenzofuran group; or a dibenzothiophene group.
  • Ar1 and Ar2 are each represented by any one of the following structures.
  • R101 is a substituted or unsubstituted aryl group.
  • Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.
  • R1, R2, L1, L2, Ar1, Ar2, a and b are the same as defined in Formula 1 above.
  • Chemical Formula 1-1 is any one of the following Chemical Formulas 1-1-1 to 1-1-3.
  • R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
  • Chemical Formula 1-2 is any one of the following Chemical Formulas 1-2-1 to 1-2-3.
  • R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
  • Chemical Formula 1-3 is any one of the following Chemical Formulas 1-3-1 to 1-3-3.
  • R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
  • Chemical Formula 1-4 is any one of the following Chemical Formulas 1-4-1 to 1-4-3.
  • R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
  • the compound of Formula 1 may be represented by any one of the following compounds.
  • the compound of Formula 1 of the present specification may have a core structure as shown in the following reaction scheme. Substituents may be combined by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.
  • L1 to L3, r1 to r3, Ar1 and Ar2 are as defined in Formula 1.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.
  • substituents by introducing various substituents into the core structure of the structure as described above, compounds having intrinsic properties of the introduced substituents can be synthesized.
  • a substituent mainly used for a hole injection layer material, a hole transport layer material, an electron blocking layer material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.
  • the organic light emitting device includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound of Formula 1 described above.
  • the organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.
  • the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to produce It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
  • the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing 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.
  • the organic material layers may be formed of the same material or different materials.
  • the organic material layer is a hole injection layer, a hole transport layer, a layer for injecting and transporting holes at the same time, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer for simultaneously injecting and transporting electrons, etc.
  • a multilayer structure comprising two or more may be, but is not limited thereto, and may have a single-layer structure.
  • the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.
  • the organic material layer may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present specification is an organic material layer, a hole injection layer, a hole transport layer, a layer that transports and injects holes at the same time, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and an electron transport and electron injection layer at the same time. It may have a structure including layers and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
  • the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer may include the compound.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound
  • the organic material layer may include an emission layer, and the emission layer may include the compound as a dopant of the emission layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a dopant of the light emitting layer, and may further include a host.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a dopant of the light emitting layer, further includes a fluorescent host or a phosphorescent host, and another organic compound, a metal or a metal compound as a dopant may further include
  • the organic material layer includes an emission layer
  • the emission layer includes the compound as a dopant of the emission layer
  • Ir iridium-based
  • the organic material layer may include an emission layer, and the emission layer may include the compound as a host of the emission layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a host of the light emitting layer, and may further include a dopant.
  • the organic material layer may include an electron blocking layer, and the electron blocking layer may include the compound.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3 , but is not limited thereto.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , a first electrode 2 , a light emitting layer 3 , and a second electrode 4 .
  • FIG. 2 is an organic light emitting device including a substrate 1 , a first electrode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 7 , an electron transport layer 8 , and a second electrode 4 . shows an example of
  • FIG. 3 is a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, a hole blocking layer 10, electron injection and An example of an organic light emitting device connected to the transport layer 11 and the second electrode 4 is shown.
  • the organic light emitting device may have, for example, the following stacked structure in addition to the structure specified in the drawings, but is not limited thereto.
  • the 'electron transport layer/electron injection layer' may be replaced with an electron injection and transport layer.
  • the hole transport layer may have a multilayer structure.
  • it may be composed of a first hole transport layer and a second hole transport layer including different materials.
  • the anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc).
  • metal oxides such as oxide
  • combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb
  • conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer that smoothly injects holes from the anode to the light emitting layer.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • hole injection material metal porphyrine, oligothiophene, arylamine-based compound, hexanitrile hexaazatriphenylene-based compound, quinacridone-based compound, perylene-based compound compound, benzonitrile-based compound, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but is not limited thereto.
  • an arylamine-based compound and a benzonitrile-based compound may be used for the hole injection layer. More specifically, a benzonitrile-based compound substituted with a halogen group and an arylamine-based compound substituted with a carbazole group may be used, but are not limited thereto.
  • the hole injection layer may have a thickness of 1 nm to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.
  • the hole transport layer may serve to facilitate hole transport.
  • the hole transport material a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable.
  • the hole transport material includes, but is not limited to, an arylamine-based compound, a carbazole-based compound, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • a carbazole-based compound substituted with an arylamine group may be used in the hole transport layer, but is not limited thereto.
  • An additional hole buffer layer is provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the above-described compound or a material known in the art may be used for the electron blocking layer.
  • the light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • the light-emitting material includes an 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; Rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compounds
  • compounds of the benzoxazole, benzthiazole and benzimidazole series Poly(p-phenylenevinylene) (PPV)-based polymers
  • spiro compounds polyfluorene
  • Rubrene and the like but are not limited thereto.
  • Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • an anthracene derivative may be used as the host of the emission layer, but is not limited thereto.
  • the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto.
  • a phosphorescent material such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum)
  • Alq 3 tris(8-hydroxyquinolino)aluminum
  • the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA),
  • a fluorescent material such as a pyrene-based compound, a PFO-based polymer, or a PPV-based polymer may be used, but is not limited thereto.
  • a pyrene-based compound may be used as the dopant, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer.
  • the material applied to the hole blocking layer includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a triazine derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.
  • a triazine derivative may be used, but is not limited thereto.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable.
  • the electron transport material includes an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, a hydroxyflavone-metal complex, and the like, but is not limited thereto.
  • the thickness of the electron transport layer may be 1 nm to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be
  • the electron injection layer may serve to facilitate electron injection.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and a thin film A compound excellent in forming ability is preferred.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • the electron transport layer and the electron injection layer may be formed as a single layer.
  • the electron injection and transport layer may be formed by vacuum deposition of the electron injection material and the electron transport material at the same time.
  • the electron injection and transport layer may further include a metal complex.
  • the metal complex include, but are not limited to, an Al complex of 8-hydroxyquinoline (Alq 3 ), LiQ, and a metal complex compound.
  • Alq 3 8-hydroxyquinoline
  • LiQ lithium quinolite
  • LiQ lithium quinolite
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a hole injection layer was formed by thermally vacuum-depositing a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode.
  • a hole transport layer was formed by vacuum-depositing a compound (1150 ⁇ ) represented by the following formula HT1 on the hole injection layer. Then, the compound 1 prepared in Preparation Example 1 to a film thickness of 50 ⁇ on the hole transport layer was vacuum-deposited to form an electron blocking layer.
  • the compound represented by the following formula BH and the compound represented by the following formula BD to a film thickness of 200 ⁇ on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing a compound represented by the following Chemical Formula HB1 to a film thickness of 50 ⁇ on the light emitting layer.
  • the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 310 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 ⁇ /sec, and the deposition rate of aluminum was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 2x10.
  • -7 torr to 5x10 -6 torr an organic light emitting diode was manufactured.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1.
  • An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1.
  • the compounds of EB2, EB3, EB4, EB5, EB6 and EB7 used in Table 1 below are as follows.
  • T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • Example 1 One 4.36 6.70 (0.144, 0.146) 255 Example 2 2 4.47 6.61 (0.146, 0.147) 240 Example 3 3 4.51 6.63 (0.146, 0.145) 245 Example 4 4 4.54 6.74 (0.145, 0.145) 240 Example 5 5 4.45 6.67 (0.146, 0.144) 235 Example 6 6 4.43 6.78 (0.146, 0.145) 245 Example 7 7 4.48 6.59 (0.145, 0.144) 230 Example 8 8 4.51 6.56 (0.145, 0.145) 235 Example 9 9 4.50 6.55 (0.144, 0.144) 240 Comparative Example 1 EB2 5.13 5.83 (0.144, 0.145) 115 Comparative Example 2 EB3 4.71 6.11 (0.145, 0.144) 90 Comparative Example 3 EB4 6.00 5.62 (0.144, 0.145)
  • the organic light emitting device using the compound of the present invention as the electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
  • the organic light emitting device using a compound other than Chemical Formula 1 as the electron blocking layer showed a characteristic that the driving voltage increased and the efficiency and lifespan decreased.
  • a compound having a different substitution position of the carbazole group in naphthalene (EB2), a compound in which naphthalene is further substituted with a substituent other than an amine group and a carbazole group (EB3), a compound having a linker between naphthalene and a carbazole group (EB4 and EB5) and Comparative Examples 1 to 6 to which compounds (EB6 and EB7) having different positions of substitution of amine groups in naphthalene were applied, compared to Examples 1 to 9, showed that the driving voltage was increased, and the efficiency and lifespan were decreased.

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Abstract

The present specification relates to: a compound of chemical formula 1; and an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein the one or more organic layers comprise the compound of chemical formula 1.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light emitting device comprising same
본 출원은 본 출원은 2021년 1월 13일에 한국특허청에 제출된 한국 특허 출원 제10-2021-0004535호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0004535 filed with the Korean Intellectual Property Office on January 13, 2021, the entire contents of which are incorporated herein by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a compound and an organic light emitting device including the same.
유기 발광 소자는 2개의 전극 사이에 유기박막을 배치시킨 구조를 가지고 있다. 이와 같은 구조의 유기 발광 소자에 전압이 인가되면, 2개의 전극으로부터 주입된 전자와 전공이 유기박막에서 결합하여 쌍을 이룬 후 소멸하면서 빛을 발하게 된다. 상기 유기박막은 필요에 따라 단층 또는 다층으로 구성될 수 있다.The organic light emitting diode has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.
유기 발광 소자에서 사용되는 물질로는 순수 유기 물질 또는 유기 물질과 금속이 착물을 이루는 착화합물이 대부분을 차지하고 있으며, 용도에 따라 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등으로 구분될 수 있다. 여기서, 정공주입 물질이나 정공수송 물질로는 p-타입의 성질을 가지는 유기물질, 즉 쉽게 산화가 되고 산화시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 한편, 전자주입 물질이나 전자수송 물질로는 n-타입 성질을 가지는 유기 물질, 즉 쉽게 환원이 되고 환원시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 발광층 물질로는 p-타입 성질과 n-타입 성질을 동시에 가진 물질, 즉 산화와 환원 상태에서 모두 안정한 형태를 갖는 물질이 바람직하며, 정공 및 전자가 발광층에서 재결합하여 생성되는 엑시톤(exciton)이 형성되었을 때 이를 빛으로 전환하는 발광 효율이 높은 물질이 바람직하다.As materials used in organic light emitting devices, pure organic materials or complex compounds in which organic materials and metals are complexed account for most, and depending on the use, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed A material with high luminous efficiency that converts it into light when it is formed is preferable.
유기 발광 소자의 성능, 수명 또는 효율을 향상시키기 위하여, 유기박막의 재료의 개발이 지속적으로 요구되고 있다.In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present specification provides a compound and an organic light emitting device comprising the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2021019198-appb-img-000001
Figure PCTKR2021019198-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a는 1 내지 4의 정수이고, 상기 a가 2 이상인 경우, 2 이상의 R1은 각각 서로 같거나 상이하고,a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,
b는 1 내지 4의 정수이고, 상기 b가 2 이상인 경우, 2 이상의 R2는 각각 서로 같거나 상이하며,b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,
r1 내지 r3는 각각 1 내지 3의 정수이고, r1 내지 r3가 각각 2 이상일 경우 각각의 괄호 안의 구조는 서로 같거나 상이하다.r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.
또한, 본 명세서의 일 실시상태는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, an exemplary embodiment of the present specification includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
본 명세서의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있고, 이를 사용함으로써 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성의 향상이 가능하다.The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.
특히, 본 발명의 화합물을 정공주입층, 정공수송층 또는 전자저지층에 사용하는 경우 소자의 구동전압이 낮아지며, 또한 소자의 효율이 증가하고, 수명이 길어지는 효과를 얻을 수 있다.In particular, when the compound of the present invention is used in the hole injection layer, the hole transport layer or the electron blocking layer, the driving voltage of the device is lowered, the efficiency of the device is increased, and the lifespan is prolonged.
도 1 내지 3은 본 명세서의 일 실시상태에 따른 유기 발광 소자를 도시한 것이다. 1 to 3 illustrate an organic light emitting diode according to an exemplary embodiment of the present specification.
1: 기판1: substrate
2: 제1 전극2: first electrode
3: 발광층3: light emitting layer
4: 제2 전극4: second electrode
5: 정공주입층5: hole injection layer
6: 정공수송층6: hole transport layer
7: 발광층7: light emitting layer
8: 전자수송층8: electron transport layer
9: 전자저지층9: Electronic barrier layer
10: 정공저지층10: hole blocking layer
11: 전자 주입 및 수송층11: Electron injection and transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present specification will be described in more detail.
본 명세서는 하기 화학식 1의 화합물을 제공한다. The present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2021019198-appb-img-000002
Figure PCTKR2021019198-appb-img-000002
상기 화학식 1에 있어서,In Formula 1,
R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a는 1 내지 4의 정수이고, 상기 a가 2 이상인 경우, 2 이상의 R1은 각각 서로 같거나 상이하고,a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,
b는 1 내지 4의 정수이고, 상기 b가 2 이상인 경우, 2 이상의 R2는 각각 서로 같거나 상이하며,b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,
r1 내지 r3는 각각 1 내지 3의 정수이고, r1 내지 r3가 각각 2 이상일 경우 각각의 괄호 안의 구조는 서로 같거나 상이하다.r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.
상기 화학식 1의 화합물은 나프탈렌기의 탄소 번호를 하기와 같이 지칭할 때, 1번 탄소가 카바졸기로, 2번 탄소가 아민기로 치환된 것이 특징이다.The compound of Formula 1 is characterized in that when the carbon number of the naphthalene group is referred to as follows, carbon 1 is substituted with a carbazole group and carbon 2 is substituted with an amine group.
Figure PCTKR2021019198-appb-img-000003
Figure PCTKR2021019198-appb-img-000003
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included, rather than excluding other components, unless otherwise stated.
이하, 본 명세서의 치환기를 이하에서 상세하게 설명하나, 이에 한정되는 것은 아니다.Hereinafter, the substituents of the present specification will be described in detail below, but the present invention is not limited thereto.
본 명세서에 있어서,
Figure PCTKR2021019198-appb-img-000004
는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,
Figure PCTKR2021019198-appb-img-000004
refers to a site bonded to another substituent or a bonding group.
본 명세서에서 상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.As used herein, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and two or more When substituted, two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기(-CN); 아민기; 알콕시기; 알킬기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 도 있다.As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); amine group; alkoxy group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에 있어서, 할로겐기의 예로는 불소(-F), 염소(-Cl), 브롬(-Br) 또는 요오드(-I)가 있다.In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 60, 예컨대 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, such as 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트렌기, 트리페닐렌기, 피렌기, 페날레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기, 플루오란텐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a fluoranthene group, etc. However, the present invention is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2021019198-appb-img-000005
,
Figure PCTKR2021019198-appb-img-000006
,
Figure PCTKR2021019198-appb-img-000007
및
Figure PCTKR2021019198-appb-img-000008
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2021019198-appb-img-000005
,
Figure PCTKR2021019198-appb-img-000006
,
Figure PCTKR2021019198-appb-img-000007
and
Figure PCTKR2021019198-appb-img-000008
etc. can be However, the present invention is not limited thereto.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, S 및 P 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 50, 나아가 2 내지 30인 것이 바람직하며, 상기 헤테로고리기는 단환식 또는 다환식일 수 있다. 상기 헤테로고리기는 방향족 고리, 지방족 고리 및 이들이 축합된 고리일 수 있다. 상기 헤테로고리기의 예로는 티오펜기, 퓨라닐기, 피롤기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 피리딜기, 바이피리딜기, 피리미딜기, 트리아지닐기, 트리아졸릴기, 아크리딜기, 피리다지닐기, 피라지닐기, 퀴놀릴기, 퀴나졸릴기, 퀴녹살릴기, 프탈라지닐기, 피리도 피리미딜기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀릴기, 인돌릴기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤리닐기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heterocyclic group includes atoms other than carbon and one or more heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, S and P, and the like. The number of carbon atoms is not particularly limited, but preferably has 1 to 50 carbon atoms, further preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group may be an aromatic ring, an aliphatic ring, and a ring condensed therewith. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, A phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 방향족고리기로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로아릴기의 탄소수는 2 내지 30이다. 헤테로아릴기의 예시는 상기 헤테로고리기의 예시 중에서 선택될 수 있다.In the present specification, the heteroaryl group is an aromatic ring group containing one or more atoms other than carbon and heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S. can Although carbon number is not specifically limited, It is preferable that carbon number is 2-60. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of the heteroaryl group may be selected from the examples of the heterocyclic group.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 0 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, N-페닐나프틸아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기, N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 0 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
본 명세서에 있어서, 알킬아민기, N-아릴알킬아민기, N-알킬헤테로아릴아민기 중의 알킬기 및 아릴기는 전술한 알킬기 및 아릴기의 예시와 같다. In the present specification, the alkyl group and the aryl group in the alkylamine group, the N-arylalkylamine group, and the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the aryl group described above.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 1 내지 50의 헤테로고리기이다.In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 1 to 50 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 각각 수소이다.In an exemplary embodiment of the present specification, R1 and R2 are each hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 a는 1 내지 4의 정수이고, 상기 a가 2 이상인 경우, 2 이상의 R1은 각각 서로 같거나 상이하다.In an exemplary embodiment of the present specification, a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R1은 수소이고, 상기 a는 4이다.In an exemplary embodiment of the present specification, R1 is hydrogen, and a is 4.
본 명세서의 일 실시상태에 있어서, 상기 b는 1 내지 4의 정수이고, 상기 b가 2 이상인 경우, 2 이상의 R2는 각각 서로 같거나 상이하다.In the exemplary embodiment of the present specification, b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R2는 수소이고, 상기 b는 4이다.In the exemplary embodiment of the present specification, R2 is hydrogen, and b is 4.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L3는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다.In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 내지 L3는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐레닐렌기; 또는 치환 또는 비치환된 플루오레닐렌기이다.In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기이다.In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐레닐렌기; 또는 치환 또는 비치환된 플루오레닐렌기이다.In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐렌기; 치환 또는 비치환된 터페닐렌기; 또는 치환 또는 비치환된 나프틸렌기이다.In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐렌기; 터페닐렌기; 또는 나프틸렌기이다.In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; terphenylene group; or a naphthylene group.
본 명세서의 일 실시상태에 있어서, 상기 L3은 직접결합; 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 바이페닐렌기이다.In an exemplary embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L3은 직접결합; 페닐렌기; 또는 바이페닐렌기이다.In an exemplary embodiment of the present specification, L3 is a direct bond; phenylene group; or a biphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L3은 페닐렌기; 또는 바이페닐렌기이다.In an exemplary embodiment of the present specification, L3 is a phenylene group; or a biphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L3는 바이페닐렌기이다.In an exemplary embodiment of the present specification, L3 is a biphenylene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 알킬기, 아릴기 및 헤테로고리로 이루어진 군에서 선택되는 하나 이상으로 치환 또는 비치환된 아릴기; 또는 알킬기, 아릴기 및 헤테로고리로 이루어진 군에서 선택되는 하나 이상으로 치환 또는 비치환된 헤테로고리기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group, an aryl group, and one or more substituted or unsubstituted aryl groups selected from the group consisting of a heterocycle; Or an alkyl group, an aryl group, and one or more unsubstituted heterocyclic groups selected from the group consisting of heterocyclic groups.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 헤테로고리기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group substituted or unsubstituted with an alkyl group or an aryl group; or a heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 바이페닐기; 아릴기로 치환 또는 비치환된 터페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난트렌기; 아릴기로 치환 또는 비치환된 트리페닐렌기; 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기; 아릴기로 치환 또는 비치환된 카바졸기; 아릴기로 치환 또는 비치환된 디벤조퓨란기; 또는 아릴기로 치환 또는 비치환된 디벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; terphenyl group unsubstituted or substituted with an aryl group; a naphthyl group unsubstituted or substituted with an aryl group; a phenanthrene group unsubstituted or substituted with an aryl group; a triphenylene group unsubstituted or substituted with an aryl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; a carbazole group unsubstituted or substituted with an aryl group; a dibenzofuran group unsubstituted or substituted with an aryl group; Or a dibenzothiophene group unsubstituted or substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 나프틸기 또는 페난트렌기로 치환 또는 비치환된 페닐기; 바이페닐기; 터페닐기; 페닐기 또는 바이페닐기로 치환 또는 비치환된 나프틸기; 페난트렌기; 트리페닐렌기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 카바졸기; 디벤조퓨란기; 또는 디벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group or a phenanthrene group; biphenyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a phenyl group or a biphenyl group; phenanthrene group; triphenylene group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; carbazole group; dibenzofuran group; or a dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 각각 하기 구조 중 어느 하나로 표시된다.In the exemplary embodiment of the present specification, Ar1 and Ar2 are each represented by any one of the following structures.
Figure PCTKR2021019198-appb-img-000009
Figure PCTKR2021019198-appb-img-000009
상기 구조들에 있어서, 점선은 결합위치를 의미하고, R101은 치환 또는 비치환된 아릴기이다.In the above structures, the dotted line indicates a bonding position, and R101 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나이다.In the exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.
[화학식 1-1][Formula 1-1]
Figure PCTKR2021019198-appb-img-000010
Figure PCTKR2021019198-appb-img-000010
[화학식 1-2][Formula 1-2]
Figure PCTKR2021019198-appb-img-000011
Figure PCTKR2021019198-appb-img-000011
[화학식 1-3][Formula 1-3]
Figure PCTKR2021019198-appb-img-000012
Figure PCTKR2021019198-appb-img-000012
[화학식 1-4][Formula 1-4]
Figure PCTKR2021019198-appb-img-000013
Figure PCTKR2021019198-appb-img-000013
상기 화학식 1-1 내지 1-4에 있어서,In Formulas 1-1 to 1-4,
R1, R2, L1, L2, Ar1, Ar2, a 및 b는 상기 화학식 1에서의 정의와 같다.R1, R2, L1, L2, Ar1, Ar2, a and b are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1-1은 하기 화학식 1-1-1 내지 1-1-3 중 어느 하나이다.In an exemplary embodiment of the present specification, Chemical Formula 1-1 is any one of the following Chemical Formulas 1-1-1 to 1-1-3.
[화학식 1-1-1][Formula 1-1-1]
Figure PCTKR2021019198-appb-img-000014
Figure PCTKR2021019198-appb-img-000014
[화학식 1-1-2][Formula 1-1-2]
Figure PCTKR2021019198-appb-img-000015
Figure PCTKR2021019198-appb-img-000015
[화학식 1-1-3][Formula 1-1-3]
Figure PCTKR2021019198-appb-img-000016
Figure PCTKR2021019198-appb-img-000016
상기 화학식 1-1-1 내지 1-1-3에 있어서, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a 및 b는 상기 화학식 1에서의 정의와 같다.In Formulas 1-1-1 to 1-1-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1-2는 하기 화학식 1-2-1 내지 1-2-3 중 어느 하나이다.In an exemplary embodiment of the present specification, Chemical Formula 1-2 is any one of the following Chemical Formulas 1-2-1 to 1-2-3.
[화학식 1-2-1][Formula 1-2-1]
Figure PCTKR2021019198-appb-img-000017
Figure PCTKR2021019198-appb-img-000017
[화학식 1-2-2][Formula 1-2-2]
Figure PCTKR2021019198-appb-img-000018
Figure PCTKR2021019198-appb-img-000018
[화학식 1-2-3][Formula 1-2-3]
Figure PCTKR2021019198-appb-img-000019
Figure PCTKR2021019198-appb-img-000019
상기 화학식 1-2-1 내지 1-2-3에 있어서, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a 및 b는 상기 화학식 1에서의 정의와 같다.In Formulas 1-2-1 to 1-2-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1-3은 하기 화학식 1-3-1 내지 1-3-3 중 어느 하나이다.In an exemplary embodiment of the present specification, Chemical Formula 1-3 is any one of the following Chemical Formulas 1-3-1 to 1-3-3.
[화학식 1-3-1][Formula 1-3-1]
Figure PCTKR2021019198-appb-img-000020
Figure PCTKR2021019198-appb-img-000020
[화학식 1-3-2][Formula 1-3-2]
Figure PCTKR2021019198-appb-img-000021
Figure PCTKR2021019198-appb-img-000021
[화학식 1-3-3][Formula 1-3-3]
Figure PCTKR2021019198-appb-img-000022
Figure PCTKR2021019198-appb-img-000022
상기 화학식 1-3-1 내지 1-3-3에 있어서, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a 및 b는 상기 화학식 1에서의 정의와 같다.In Formulas 1-3-1 to 1-3-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1-4는 하기 화학식 1-4-1 내지 1-4-3 중 어느 하나이다.In an exemplary embodiment of the present specification, Chemical Formula 1-4 is any one of the following Chemical Formulas 1-4-1 to 1-4-3.
[화학식 1-4-1][Formula 1-4-1]
Figure PCTKR2021019198-appb-img-000023
Figure PCTKR2021019198-appb-img-000023
[화학식 1-4-2][Formula 1-4-2]
Figure PCTKR2021019198-appb-img-000024
Figure PCTKR2021019198-appb-img-000024
[화학식 1-4-3][Formula 1-4-3]
Figure PCTKR2021019198-appb-img-000025
Figure PCTKR2021019198-appb-img-000025
상기 화학식 1-4-1 내지 1-4-3에 있어서, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a 및 b는 상기 화학식 1에서의 정의와 같다.In Formulas 1-4-1 to 1-4-3, R1, R2, L1, L2, Ar1, Ar2, r1, r2, a, and b are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 하기 화합물 중 어느 하나로 표시될 수 있다.In an exemplary embodiment of the present specification, the compound of Formula 1 may be represented by any one of the following compounds.
Figure PCTKR2021019198-appb-img-000026
Figure PCTKR2021019198-appb-img-000026
Figure PCTKR2021019198-appb-img-000027
Figure PCTKR2021019198-appb-img-000027
Figure PCTKR2021019198-appb-img-000028
Figure PCTKR2021019198-appb-img-000028
Figure PCTKR2021019198-appb-img-000029
Figure PCTKR2021019198-appb-img-000029
Figure PCTKR2021019198-appb-img-000030
Figure PCTKR2021019198-appb-img-000030
Figure PCTKR2021019198-appb-img-000031
Figure PCTKR2021019198-appb-img-000031
Figure PCTKR2021019198-appb-img-000032
Figure PCTKR2021019198-appb-img-000032
본 명세서의 화학식 1의 화합물은 하기 반응식과 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 및 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.The compound of Formula 1 of the present specification may have a core structure as shown in the following reaction scheme. Substituents may be combined by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.
<반응식><reaction formula>
Figure PCTKR2021019198-appb-img-000033
Figure PCTKR2021019198-appb-img-000033
상기 반응식에 있어서, L1 내지 L3, r1 내지 r3, Ar1 및 Ar2는 화학식 1에서 정의한 것과 같다.In the above scheme, L1 to L3, r1 to r3, Ar1 and Ar2 are as defined in Formula 1.
본 명세서에서는 상기와 같이 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 또한, 본 발명에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위도 조절할 수 있다.In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공주입층 물질, 정공수송층 물질, 전자저지층 물질, 발광층 물질 및 전자수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.In addition, by introducing various substituents into the core structure of the structure as described above, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport layer material, an electron blocking layer material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.
또한, 본 명세서에 따른 유기 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 전술한 화학식 1의 화합물을 포함한다.In addition, the organic light emitting device according to the present specification includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound of Formula 1 described above.
본 명세서의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 물리 증착 방법(PVD: physical Vapor Deposition)을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 제1 전극을 형성하고, 그 위에 정공주입층, 정공수송층, 발광층 및 전자수송층을 포함하는 유기물층을 형성한 후, 그 위에 제2 전극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 제2 전극 물질부터 유기물층, 제1 전극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 상기 화학식 1로 표시되는 헤테로고리 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to produce It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, 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.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
상기 유기물층은 정공주입층, 정공수송층, 정공 주입과 정공 수송을 동시에 하는층, 전자저지층, 발광층, 전자수송층, 전자주입층 및 전자 주입과 전자 수송을 동시에 하는 층 등에서 2 이상을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer is a hole injection layer, a hole transport layer, a layer for injecting and transporting holes at the same time, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer for simultaneously injecting and transporting electrons, etc. A multilayer structure comprising two or more may be, but is not limited thereto, and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 명세서의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 정공수송 및 정공주입을 동시에 하는 층, 전자저지층, 발광층, 전자수송층, 전자주입층, 및 전자수송 및 전자주입을 동시에 하는 층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기물층을 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present specification is an organic material layer, a hole injection layer, a hole transport layer, a layer that transports and injects holes at the same time, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and an electron transport and electron injection layer at the same time. It may have a structure including layers and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층은 상기 화합물을 포함한다.In an exemplary embodiment of the present specification, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공주입층, 정공수송층 또는 전자저지층을 포함하고, 상기 정공주입층, 정공수송층 또는 전자저지층은 상기 화합물을 포함할 수 있다.In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer may include the compound.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층이 상기 화합물을 포함한다.In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer may include an emission layer, and the emission layer may include the compound as a dopant of the emission layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함하고, 호스트를 더 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, and may further include a host.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 더 포함하며, 다른 유기화합물, 금속 또는 금속화합물을 도펀트로 더 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, further includes a fluorescent host or a phosphorescent host, and another organic compound, a metal or a metal compound as a dopant may further include
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 더 포함하며, 이리듐계(Ir) 도펀트도 함께 사용할 수 있다.In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes the compound as a dopant of the emission layer, further includes a fluorescent host or a phosphorescent host, and an iridium-based (Ir) dopant can also be used. have.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 호스트로서 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer may include an emission layer, and the emission layer may include the compound as a host of the emission layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 호스트로서 포함하고, 도펀트를 더 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a host of the light emitting layer, and may further include a dopant.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자저지층을 포함하고, 상기 전자저지층은 상기 화합물을 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer may include an electron blocking layer, and the electron blocking layer may include the compound.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.
예컨대, 본 명세서의 유기 발광 소자의 구조는 도 1 내지 도 3에 나타난 것과 같은 구조를 가질 수 있으나 이에만 한정되는 것은 아니다.For example, the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3 , but is not limited thereto.
도 1은 기판(1), 제1 전극(2), 발광층(3) 및 제2 전극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting device including a substrate 1 , a first electrode 2 , a light emitting layer 3 , and a second electrode 4 .
도 2는 기판(1), 제1 전극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 제2 전극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.2 is an organic light emitting device including a substrate 1 , a first electrode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 7 , an electron transport layer 8 , and a second electrode 4 . shows an example of
도 3은 기판(1), 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자저지층(9), 발광층(7), 정공저지층(10), 전자 주입 및 수송층(11) 및 제2 전극(4)으로 이어진 유기 발광 소자의 예를 도시한 것이다.3 is a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, a hole blocking layer 10, electron injection and An example of an organic light emitting device connected to the transport layer 11 and the second electrode 4 is shown.
구체적으로, 상기 유기 발광 소자는 상기 도면에 명시된 구조 외에 예컨대 하기와 같은 적층 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.Specifically, the organic light emitting device may have, for example, the following stacked structure in addition to the structure specified in the drawings, but is not limited thereto.
(1) 양극/정공수송층/발광층/음극(1) anode/hole transport layer/light emitting layer/cathode
(2) 양극/정공주입층/정공수송층/발광층/음극(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode
(3) 양극/정공수송층/발광층/전자수송층/음극(3) anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) 양극/정공수송층/발광층/전자수송층/전자주입층/음극(4) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(5) 양극/정공주입층/정공수송층/발광층/전자수송층/음극(5) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(7) 양극/ 정공수송층/전자저지층/발광층/전자수송층/음극(7) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode
(8) 양극/ 정공수송층/전자저지층/발광층/전자수송층/전자주입층/음극(8) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode
(9) 양극/정공주입층/정공수송층/전자저지층/발광층/전자수송층/음극(9) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode
(10) 양극/정공주입층/정공수송층/전자저지층/발광층/전자수송층/전자주입층/음극(10) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode
(11) 양극/정공수송층/발광층/정공저지층/전자수송층/음극(11) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode
(12) 양극/정공수송층/발광층/정공저지층/전자수송층/전자주입층/음극(12) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode
(13) 양극/정공주입층/정공수송층/발광층/정공저지층/전자수송층/음극(13) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode
(14) 양극/정공주입층/정공수송층/발광층/정공저지층/전자수송층/전자주입층/음극(14) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode
(15) 양극/정공주입층/정공수송층/전자저지층/발광층/정공저지층/전자수송 및 전자주입을 동시에 하는 층/음극(15) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / layer that simultaneously transports and injects electrons / cathode
본 명세서의 일 실시상태에 있어서, 상기 '전자수송층/전자주입층'은 전자 주입 및 수송층으로 대체될 수 있다.In the exemplary embodiment of the present specification, the 'electron transport layer/electron injection layer' may be replaced with an electron injection and transport layer.
본 명세서의 일 실시상태에 있어서, 상기 정공수송층은 다층 구조로 이루어질 수 있다. 예컨대, 서로 상이한 물질을 포함하는 제1 정공수송층 및 제2 정공수송층으로 구성될 수 있다.In an exemplary embodiment of the present specification, the hole transport layer may have a multilayer structure. For example, it may be composed of a first hole transport layer and a second hole transport layer including different materials.
상기 양극은 정공을 주입하는 전극으로, 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예컨대, 상기 양극 물질예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO, Indium Tin Oxide), 인듐아연 산화물(IZO, Indium Zinc Oxide)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 및 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. For example, examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc). metal oxides such as oxide); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto. .
상기 음극은 전자를 주입하는 전극으로, 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예컨대, 상기 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. For example, examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
상기 정공주입층은 애노드로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이다. 정공 주입 물질로는 낮은 전압에서 애노드로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 애노드 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 예컨대, 정공 주입 물질로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 화합물, 헥사니트릴헥사아자트리페닐렌 계열의 화합물, 퀴나크리돈(quinacridone) 계열의 화합물, 페릴렌(perylene) 계열의 화합물, 벤조니트릴 계열의 화합물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 정공주입층은 아릴아민 계열의 화합물 및 벤조니트릴계열의 화합물이 사용될 수 있다. 보다 구체적으로, 할로겐기로 치환된 벤조니트릴계 화합물 및 카바졸기로 치환된 아릴아민계 화합물이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 정공주입층의 두께는 1nm 내지 150nm일 수 있다. 상기 정공주입층의 두께가 1nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공주입층의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.The hole injection layer is a layer that smoothly injects holes from the anode to the light emitting layer. The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. For example, as the hole injection material, metal porphyrine, oligothiophene, arylamine-based compound, hexanitrile hexaazatriphenylene-based compound, quinacridone-based compound, perylene-based compound compound, benzonitrile-based compound, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but is not limited thereto. Specifically, for the hole injection layer, an arylamine-based compound and a benzonitrile-based compound may be used. More specifically, a benzonitrile-based compound substituted with a halogen group and an arylamine-based compound substituted with a carbazole group may be used, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송 물질로는 애노드나 정공주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 예컨대, 정공 수송 물질로는 아릴아민 계열의 화합물, 카바졸 계열의 화합물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 정공수송층에는 아릴아민기로 치환된 카바졸계 화합물이 사용될 수 있으나, 이에만 한정되는 것은 아니다.The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable. For example, the hole transport material includes, but is not limited to, an arylamine-based compound, a carbazole-based compound, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. Specifically, a carbazole-based compound substituted with an arylamine group may be used in the hole transport layer, but is not limited thereto.
정공주입층과 정공수송층 사이에 추가로 정공버퍼층이 구비될 있으며, 당 기술분야에 알려져 있는 정공주입 또는 수송 재료를 포함할 수 있다. An additional hole buffer layer is provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
정공수송층과 발광층 사이에 전자저지층이 구비될 수 있다. 상기 전자저지층에는 전술한 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다.An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-described compound or a material known in the art may be used for the electron blocking layer.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 예컨대, 상기 발광 물질로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌; 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. As the light emitting material, a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, the light-emitting material includes an 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; Rubrene and the like, but are not limited thereto.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 예컨대, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 발광층의 호스트로는 안트라센 유도체가 사용될 수 있으나, 이에만 한정되는 것은 아니다.Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. For example, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Specifically, an anthracene derivative may be used as the host of the emission layer, but is not limited thereto.
발광층이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), 피렌계 화합물, PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 도펀트로는 피렌계 화합물이 사용될 수 있으나, 이에만 한정되는 것은 아니다.When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphorescent material such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light-emitting layer emits blue light, the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a pyrene-based compound, a PFO-based polymer, or a PPV-based polymer may be used, but is not limited thereto. Specifically, a pyrene-based compound may be used as the dopant, but is not limited thereto.
전자수송층과 발광층 사이에 정공저지층이 구비될 수 있다. 상기 정공저지층은 정공의 캐소드 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 예컨대, 상기 정공저지층에 적용되는 물질로는 옥사디아졸 유도체나 트리아졸 유도체, 트리아진 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 트리아진 유도체가 사용될 수 있으나, 이에만 한정되는 것은 아니다.A hole blocking layer may be provided between the electron transport layer and the light emitting layer. The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. For example, the material applied to the hole blocking layer includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a triazine derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like. Specifically, a triazine derivative may be used, but is not limited thereto.
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 할 수 있다. 전자 수송 물질로는 캐소드로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 예컨대, 상기 전자 수송 물질로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1nm 내지 50nm일 수 있다. 전자수송층의 두께가 1nm 이상이면, 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자수송층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. For example, the electron transport material includes an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, a hydroxyflavone-metal complex, and the like, but is not limited thereto. The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 캐소드로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층으로의 이동을 방지하고, 박막형성능력이 우수한 화합물이 바람직하다. 예컨대, 상기 전자 주입 물질로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 트리아진, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체; 금속 착체 화합물; 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다.The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and a thin film A compound excellent in forming ability is preferred. For example, as the electron injection material, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane , anthrone, and their derivatives; metal complex compounds; and nitrogen-containing 5-membered ring derivatives, but is not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.
상기 전자수송층 및 전자주입층은 단층으로 형성될 수 있다. 예컨대, 전자 주입 물질과 전자 수송 물질을 동시에 진공증착하여 전자주입 및 수송층을 형성할 수 있다. 상기 전자주입 및 수송층은 금속 착체를 더 포함할 수 있다. 상기 금속 착체의 예로는 8-히드록시퀴놀린의 Al 착물(Alq3), LiQ, 금속 착체 화합물 등이 있으나, 이에만 한정되지 않는다. 예컨대, 상기 전자 주입 및 수송층은 트리아진 유도체와 리튬퀴놀라이트(LiQ)가 사용될 수 있으나, 이에만 한정되는 것은 아니다The electron transport layer and the electron injection layer may be formed as a single layer. For example, the electron injection and transport layer may be formed by vacuum deposition of the electron injection material and the electron transport material at the same time. The electron injection and transport layer may further include a metal complex. Examples of the metal complex include, but are not limited to, an Al complex of 8-hydroxyquinoline (Alq 3 ), LiQ, and a metal complex compound. For example, a triazine derivative and lithium quinolite (LiQ) may be used for the electron injection and transport layer, but the present invention is not limited thereto.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실험예를 들어 상세하기 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러가지 다른 형태로 변형될 수 있으며, 본 출원의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 출원의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, an experimental example will be described in detail to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those of ordinary skill in the art.
<< 제조예production example >>
제조예production example 1. One.
Figure PCTKR2021019198-appb-img-000034
Figure PCTKR2021019198-appb-img-000034
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-4-클로로페닐)나프탈렌-1-일)-9H-카바졸(9-(2-(4-chlorophenyl)naphthalen-1-yl)-9H-carbazole)(7.44 g, 18.42 mmol) 및 화합물 a1(8.04 g, 20.26 mmol)을 자일렌(Xylene) 270 mL에 완전히 녹인 후 소듐 터트-부톡사이드(Sodium tert-butoxide, NaOtBu)(2.65 g, 27.62 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀)팔라듐(0)(Bis(tri-tert-butylphosphine) palladium(0))(0.19 g, 0.37 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터(filter)하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 화합물 1(8.95 g, 수율: 64%)을 제조하였다.Compound 9-(2-4-chlorophenyl)naphthalen-1-yl)-9H-carbazole(9-(2-(4-chlorophenyl)naphthalen-1-yl)-9H in a 500 mL round bottom flask under nitrogen atmosphere -carbazole) (7.44 g, 18.42 mmol) and compound a1 (8.04 g, 20.26 mmol) were completely dissolved in 270 mL of xylene, and then sodium tert-butoxide (NaOtBu) (2.65 g, 27.62) mmol), and bis(tri- tert -butylphosphine)palladium(0)(Bis(tri- tert -butylphosphine)palladium(0))(0.19 g, 0.37 mmol) was added, followed by heating and stirring for 5 hours. . After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare compound 1 (8.95 g, yield: 64%).
MS[M+H]+= 765MS[M+H] + = 765
제조예production example 2. 2.
Figure PCTKR2021019198-appb-img-000035
Figure PCTKR2021019198-appb-img-000035
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-4-클로로페닐)나프탈렌-1-일)-9H-카바졸(9-(2-(4-chlorophenyl)naphthalen-1-yl)-9H-carbazole)(7.66 g, 18.96 mmol) 및 화합물 a2(8.78 g, 20.86 mmol)를 자일렌 270 mL에 완전히 녹인 후 NaOtBu(2.73 g, 28.44 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.19 g, 0.38 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 화합물 2(10.27 g, 수율: 69%)를 제조하였다.Compound 9-(2-4-chlorophenyl)naphthalen-1-yl)-9H-carbazole(9-(2-(4-chlorophenyl)naphthalen-1-yl)-9H in a 500 mL round bottom flask under nitrogen atmosphere -carbazole) (7.66 g, 18.96 mmol) and compound a2 (8.78 g, 20.86 mmol) were completely dissolved in 270 mL of xylene, NaOtBu (2.73 g, 28.44 mmol) was added, and Bis(tri- tert -butylphosphine) palladium After (0) (0.19 g, 0.38 mmol) was added, the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare compound 2 (10.27 g, yield: 69%).
MS[M+H]+= 789MS[M+H] + = 789
제조예production example 3. 3.
Figure PCTKR2021019198-appb-img-000036
Figure PCTKR2021019198-appb-img-000036
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-(3-클로로페닐)나프탈렌-1-일)-9H-카바졸(9-(2-(3-chlorophenyl)naphthalen-1-yl)-9H-carbazole)(8.11 g, 20.07 mmol) 및 화합물 a3(7.97 g, 22.08 mmol)을 자일렌 250 mL에 완전히 녹인 후 NaOtBu(2.89g, 30.11 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.21 g, 0.40 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 280 mL으로 재결정하여 화합물 3(8.91 g, 수율: 61%)을 제조하였다.Compound 9-(2-(3-chlorophenyl)naphthalen-1-yl)-9H-carbazole(9-(2-(3-chlorophenyl)naphthalen-1-yl)- in a 500 mL round bottom flask under nitrogen atmosphere 9H-carbazole) (8.11 g, 20.07 mmol) and compound a3 (7.97 g, 22.08 mmol) were completely dissolved in 250 mL of xylene, and NaOtBu (2.89 g, 30.11 mmol) was added thereto, followed by Bis(tri- tert -butylphosphine). After adding palladium (0) (0.21 g, 0.40 mmol), the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 280 mL of ethyl acetate to prepare compound 3 (8.91 g, yield: 61%).
MS[M+H]+= 729MS[M+H] + = 729
제조예production example 4. 4.
Figure PCTKR2021019198-appb-img-000037
Figure PCTKR2021019198-appb-img-000037
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-4-클로로페닐)나프탈렌-1-일)-9H-카바졸(9-(2-(4-chlorophenyl)naphthalen-1-yl)-9H-carbazole)(8.33 g, 20.62 mmol) 및 화합물 a4(9.32 g, 22.68 mmol)를 자일렌 280 mL에 완전히 녹인 후 NaOtBu(2.97 g, 30.93 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.21 g, 0.41 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 4(11.06 g, 수율: 69%)를 제조하였다.Compound 9-(2-4-chlorophenyl)naphthalen-1-yl)-9H-carbazole(9-(2-(4-chlorophenyl)naphthalen-1-yl)-9H in a 500 mL round bottom flask under nitrogen atmosphere -carbazole) (8.33 g, 20.62 mmol) and compound a4 (9.32 g, 22.68 mmol) were completely dissolved in 280 mL of xylene, NaOtBu (2.97 g, 30.93 mmol) was added thereto, and Bis(tri- tert -butylphosphine) palladium (0) (0.21 g, 0.41 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 4 (11.06 g, yield: 69%).
MS[M+H]+= 779MS[M+H] + = 779
제조예production example 5. 5.
Figure PCTKR2021019198-appb-img-000038
Figure PCTKR2021019198-appb-img-000038
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-4'-클로로-[1,1'-비페닐]-4-일)나프탈렌-1-일)-9H-카바졸(9-(2-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole)(8.05 g, 16.77 mmol) 및 화합물 a5(5.44 g, 18.45 mmol)를 자일렌 250 mL에 완전히 녹인 후 NaOtBu(2.42 g, 25.16 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.17 g, 0.34 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 화합물 5(8.82 g, 수율: 71%)를 제조하였다.Compound 9-(2-4'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole (9-(2) in a 500 mL round bottom flask under nitrogen atmosphere -(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole) (8.05 g, 16.77 mmol) and compound a5 (5.44 g, 18.45 mmol) with xyl After completely dissolving in 250 mL of Rennes, NaOtBu (2.42 g, 25.16 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0) (0.17 g, 0.34 mmol) was added, and the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare compound 5 (8.82 g, yield: 71%).
MS[M+H]+= 739MS[M+H] + = 739
제조예production example 6. 6.
Figure PCTKR2021019198-appb-img-000039
Figure PCTKR2021019198-appb-img-000039
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-(3'-클로로-[1,1'-비페닐]-3-일)나프탈렌-1-일)-9H-카바졸(9-(2-(3'-chloro-[1,1'-biphenyl]-3-yl)naphthalen-1-yl)-9H-carbazole)(8.56 g, 17.83 mmol) 및 화합물 a6(6.30 g, 19.62 mmol)을 자일렌 240 mL에 완전히 녹인 후 NaOtBu(2.57 g, 26.75 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.18 g, 0.36 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 290 mL으로 재결정하여 화합물 6(9.22 g, 수율: 68%)를 제조하였다.Compound 9-(2-(3'-chloro-[1,1'-biphenyl]-3-yl)naphthalen-1-yl)-9H-carbazole (9-( 2-(3'-chloro-[1,1'-biphenyl]-3-yl)naphthalen-1-yl)-9H-carbazole) (8.56 g, 17.83 mmol) and compound a6 (6.30 g, 19.62 mmol) After completely dissolving in 240 mL of xylene, NaOtBu (2.57 g, 26.75 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.18 g, 0.36 mmol) was added thereto, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 290 mL of ethyl acetate to prepare compound 6 (9.22 g, yield: 68%).
MS[M+H]+= 765MS[M+H] + = 765
제조예production example 7. 7.
Figure PCTKR2021019198-appb-img-000040
Figure PCTKR2021019198-appb-img-000040
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-(2'-클로로-[1,1'-비페닐]-2-일)나프탈렌-1-일)-9H-카바졸(9-(2-(2'-chloro-[1,1'-biphenyl]-2-yl)naphthalen-1-yl)-9H-carbazole)(9.26 g, 19.29 mmol) 및 화합물 a7(7.32 g, 21.22 mmol)을 자일렌 280 mL에 완전히 녹인 후 NaOtBu(2.78 g, 28.94 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.39 mmol)을 넣은 후 6시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 화합물 7(7.65 g, 수율: 50%)를 제조하였다.Compound 9-(2-(2'-chloro-[1,1'-biphenyl]-2-yl)naphthalen-1-yl)-9H-carbazole (9-( 2-(2'-chloro-[1,1'-biphenyl]-2-yl)naphthalen-1-yl)-9H-carbazole) (9.26 g, 19.29 mmol) and compound a7 (7.32 g, 21.22 mmol) After completely dissolving in 280 mL of xylene, NaOtBu (2.78 g, 28.94 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.20 g, 0.39 mmol) was added thereto, followed by heating and stirring for 6 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate to prepare compound 7 (7.65 g, yield: 50%).
MS[M+H]+= 789MS[M+H] + = 789
제조예production example 8. 8.
Figure PCTKR2021019198-appb-img-000041
Figure PCTKR2021019198-appb-img-000041
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-(3'-클로로-[1,1'-비페닐]-4-일)나프탈렌-1-일)-9H-카바졸(9-(2-(3'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole)(8.88 g, 18.50 mmol) 및 화합물 a8(6.49 g, 20.35 mmol)을 자일렌 250 mL에 완전히 녹인 후 NaOtBu(2.67 g, 27.75 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.19 g, 0.37 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 8(9.77 g, 수율: 78%)를 제조하였다.Compound 9-(2-(3'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole (9-( 2-(3'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole) (8.88 g, 18.50 mmol) and compound a8 (6.49 g, 20.35 mmol) After completely dissolving in 250 mL of xylene, NaOtBu (2.67 g, 27.75 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0)(0.19 g, 0.37 mmol) was added, and the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 8 (9.77 g, yield: 78%).
MS[M+H]+= 763MS[M+H] + = 763
제조예production example 9. 9.
Figure PCTKR2021019198-appb-img-000042
Figure PCTKR2021019198-appb-img-000042
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(2-(2'-클로로-[1,1'-비페닐]-4-일)나프탈렌-1-일)-9H-카바졸(9-(2-(2'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole)(8.37 g, 17.44 mmol) 및 화합물 a9(7.71 g, 19.18 mmol)을 자일렌 250 mL에 완전히 녹인 후 NaOtBu(2.51 g, 26.16 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.18 g, 0.35 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터하여 base를 제거한 후 자일렌을 감압농축 시키고 테트라하이드로퓨란 250 mL으로 재결정하여 화합물 9(8.53 g, 수율: 58%)를 제조하였다.Compound 9-(2-(2'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole (9-( 2-(2'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)-9H-carbazole) (8.37 g, 17.44 mmol) and compound a9 (7.71 g, 19.18 mmol) After completely dissolving in 250 mL of xylene, NaOtBu (2.51 g, 26.16 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0) (0.18 g, 0.35 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 250 mL of tetrahydrofuran to prepare compound 9 (8.53 g, yield: 58%).
MS[M+H]+= 846MS[M+H] + = 846
실시예Example 1. One.
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 양극인 ITO 투명 전극 위에 하기 화합물 HI1 및 하기 화합물 HI2의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식 HT1으로 표시되는 화합물(1150Å)을 진공 증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 50Å으로 제조예 1에서 제조한 화합물 1을 진공 증착하여 전자저지층을 형성하였다. 이어서, 상기 전자저지층 위에 막 두께 200Å으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 막 두께 50Å으로 하기 화학식 HB1으로 표시되는 화합물을 진공 증착하여 정공저지층을 형성하였다. 이어서, 상기 정공저지층 위에 하기 화학식 ET1으로 표시되는 화합물과 하기 화학식 LiQ로 표시되는 화합물을 1:1의 중량비로 진공증착하여 310Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å 두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. A hole injection layer was formed by thermally vacuum-depositing a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode. A hole transport layer was formed by vacuum-depositing a compound (1150 Å) represented by the following formula HT1 on the hole injection layer. Then, the compound 1 prepared in Preparation Example 1 to a film thickness of 50 Å on the hole transport layer was vacuum-deposited to form an electron blocking layer. Then, the compound represented by the following formula BH and the compound represented by the following formula BD to a film thickness of 200 Å on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing a compound represented by the following Chemical Formula HB1 to a film thickness of 50 Å on the light emitting layer. Then, on the hole blocking layer, the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
Figure PCTKR2021019198-appb-img-000043
Figure PCTKR2021019198-appb-img-000043
상기의 과정에서 유기물의 증착속도는 0.4Å/sec 내지 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2x10-7 torr 내지 5x10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2x10. By maintaining -7 torr to 5x10 -6 torr, an organic light emitting diode was manufactured.
실시예Example 2 내지 9. 2 to 9.
상기 실시예 1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1.
비교예comparative example 1 내지 6. 1 to 6.
상기 실시예 1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 EB2, EB3, EB4, EB5, EB6 및 EB7의 화합물은 하기와 같다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1. The compounds of EB2, EB3, EB4, EB5, EB6 and EB7 used in Table 1 below are as follows.
Figure PCTKR2021019198-appb-img-000044
Figure PCTKR2021019198-appb-img-000044
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물
(전자저지층)compound
(Electronic blocking layer) 		전압
(V@10mA
/cm2)Voltage
(V@10mA
/cm 2 ) 		효율
(cd/A@10mA
/cm2)efficiency
(cd/A@10mA
/cm 2 ) 		색좌표
(x,y)color coordinates
(x,y) 		T95
(hr)T95
(hr)
실시예 1Example 1 1One 4.364.36 6.706.70 (0.144, 0.146)(0.144, 0.146) 255255
실시예 2Example 2 22 4.474.47 6.616.61 (0.146, 0.147)(0.146, 0.147) 240240
실시예 3Example 3 33 4.514.51 6.636.63 (0.146, 0.145)(0.146, 0.145) 245245
실시예 4Example 4 44 4.544.54 6.746.74 (0.145, 0.145)(0.145, 0.145) 240240
실시예 5Example 5 55 4.454.45 6.676.67 (0.146, 0.144)(0.146, 0.144) 235235
실시예 6Example 6 66 4.434.43 6.786.78 (0.146, 0.145)(0.146, 0.145) 245245
실시예 7Example 7 77 4.484.48 6.596.59 (0.145, 0.144)(0.145, 0.144) 230230
실시예 8Example 8 88 4.514.51 6.566.56 (0.145, 0.145)(0.145, 0.145) 235235
실시예 9Example 9 99 4.504.50 6.556.55 (0.144, 0.144)(0.144, 0.144) 240240
비교예 1Comparative Example 1 EB2EB2 5.135.13 5.835.83 (0.144, 0.145)(0.144, 0.145) 115115
비교예 2Comparative Example 2 EB3EB3 4.714.71 6.116.11 (0.145, 0.144)(0.145, 0.144) 9090
비교예 3Comparative Example 3 EB4EB4 6.006.00 5.625.62 (0.144, 0.145)(0.144, 0.145) 8585
비교예 4Comparative Example 4 EB5EB5 5.075.07 5.705.70 (0.145, 0.145)(0.145, 0.145) 7070
비교예 5Comparative Example 5 EB6EB6 5.185.18 5.815.81 (0.145, 0.144)(0.145, 0.144) 105105
비교예 6Comparative Example 6 EB7EB7 5.295.29 5.835.83 (0.144, 0.147)(0.144, 0.147) 120120
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 전자저지층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다.As shown in Table 1, the organic light emitting device using the compound of the present invention as the electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
반면에, 화학식 1이 아닌 화합물을 전자저지층으로 사용한 유기 발광 소자는 구동 전압이 상승하고, 효율 및 수명이 저하되는 특성을 보였다.On the other hand, the organic light emitting device using a compound other than Chemical Formula 1 as the electron blocking layer showed a characteristic that the driving voltage increased and the efficiency and lifespan decreased.
구체적으로, 나프탈렌에서 카바졸기의 치환 위치가 다른 화합물(EB2), 나프탈렌이 아민기 및 카바졸기 외에 다른 치환기로 더 치환된 화합물(EB3), 나프탈렌과 카바졸기 사이에 링커가 구비된 화합물(EB4 및 EB5) 및 나프탈렌에서 아민기의 치환 위치가 다른 화합물(EB6 및 EB7)을 적용한 비교예 1 내지 6은 실시예 1 내지 9에 비하여 구동전압이 상승하고, 효율 및 수명이 저하되는 특성을 보였다.Specifically, a compound having a different substitution position of the carbazole group in naphthalene (EB2), a compound in which naphthalene is further substituted with a substituent other than an amine group and a carbazole group (EB3), a compound having a linker between naphthalene and a carbazole group (EB4 and EB5) and Comparative Examples 1 to 6 to which compounds (EB6 and EB7) having different positions of substitution of amine groups in naphthalene were applied, compared to Examples 1 to 9, showed that the driving voltage was increased, and the efficiency and lifespan were decreased.
이상을 통해 본 발명의 바람직한 실시예(전자저지층)에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although the preferred embodiment (electronic blocking layer) of the present invention has been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and the detailed description of the invention, and this belongs to the scope of the invention.

Claims (7)

  1. 하기 화학식 1의 화합물:A compound of formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2021019198-appb-img-000045
    Figure PCTKR2021019198-appb-img-000045
    상기 화학식 1에 있어서,In Formula 1,
    R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이며,L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    a는 1 내지 4의 정수이고, 상기 a가 2 이상인 경우, 2 이상의 R1은 각각 서로 같거나 상이하고,a is an integer of 1 to 4, and when a is 2 or more, R1 of 2 or more are the same as or different from each other,
    b는 1 내지 4의 정수이고, 상기 b가 2 이상인 경우, 2 이상의 R2는 각각 서로 같거나 상이하며,b is an integer of 1 to 4, and when b is 2 or more, R2 or more are the same as or different from each other,
    r1 내지 r3는 각각 1 내지 3의 정수이고, r1 내지 r3가 각각 2 이상일 경우 각각의 괄호 안의 구조는 서로 같거나 상이하다.r1 to r3 are each an integer of 1 to 3, and when r1 to r3 are each 2 or more, the structures in parentheses are the same as or different from each other.
  2. 청구항 1에 있어서, The method according to claim 1,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐렌기; 치환 또는 비치환된 터페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 페난트레닐렌기; 치환 또는 비치환된 트리페닐레닐렌기; 또는 치환 또는 비치환된 플루오레닐렌기인 것인 화합물.L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; or a substituted or unsubstituted fluorenylene group.
  3. 청구항 1에 있어서, The method according to claim 1,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기인 것인 화합물.Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
  4. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나인 것인 화합물:Formula 1 is a compound of any one of Formulas 1-1 to 1-4:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2021019198-appb-img-000046
    Figure PCTKR2021019198-appb-img-000046
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2021019198-appb-img-000047
    Figure PCTKR2021019198-appb-img-000047
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2021019198-appb-img-000048
    Figure PCTKR2021019198-appb-img-000048
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2021019198-appb-img-000049
    Figure PCTKR2021019198-appb-img-000049
    상기 화학식 1-1 내지 1-4에 있어서,In Formulas 1-1 to 1-4,
    R1, R2, L1, L2, Ar1, Ar2, r1, r2, a 및 b는 상기 화학식 1에서의 정의와 같다.R1, R2, L1, L2, Ar1, Ar2, r1, r2, a and b are the same as defined in Formula 1 above.
  5. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 1은 하기 화합물 중 어느 하나인 것인 화합물: The compound of Formula 1 is any one of the following compounds:
    Figure PCTKR2021019198-appb-img-000050
    Figure PCTKR2021019198-appb-img-000050
    Figure PCTKR2021019198-appb-img-000051
    Figure PCTKR2021019198-appb-img-000051
    Figure PCTKR2021019198-appb-img-000052
    Figure PCTKR2021019198-appb-img-000052
    Figure PCTKR2021019198-appb-img-000053
    Figure PCTKR2021019198-appb-img-000053
    Figure PCTKR2021019198-appb-img-000054
    Figure PCTKR2021019198-appb-img-000054
    Figure PCTKR2021019198-appb-img-000055
    Figure PCTKR2021019198-appb-img-000055
    Figure PCTKR2021019198-appb-img-000056
    Figure PCTKR2021019198-appb-img-000056
  6. 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 5 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 5. light emitting element.
  7. 청구항 6에 있어서, 상기 유기물층은 정공주입층, 정공수송층 또는 전자저지층을 포함하고, 상기 정공주입층, 정공수송층 또는 전자저지층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 6 , wherein the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer includes the compound.
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KR20150006374A (en) * 2013-07-08 2015-01-16 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
KR20160091198A (en) * 2015-01-23 2016-08-02 삼성에스디아이 주식회사 Organic optoelectric device and display device
KR20170036641A (en) * 2015-09-24 2017-04-03 주식회사 엘지화학 Compound and organic electronic device comprising the same
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CN113045481A (en) * 2019-12-27 2021-06-29 合肥鼎材科技有限公司 Compound, application thereof and organic electroluminescent device comprising compound

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KR20160091198A (en) * 2015-01-23 2016-08-02 삼성에스디아이 주식회사 Organic optoelectric device and display device
KR20170036641A (en) * 2015-09-24 2017-04-03 주식회사 엘지화학 Compound and organic electronic device comprising the same
WO2020220942A1 (en) * 2019-04-30 2020-11-05 北京鼎材科技有限公司 Compound, organic electroluminescent device containing same, and application thereof
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