WO2021029709A1 - Organic light-emitting device - Google Patents

Organic light-emitting device Download PDF

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WO2021029709A1
WO2021029709A1 PCT/KR2020/010782 KR2020010782W WO2021029709A1 WO 2021029709 A1 WO2021029709 A1 WO 2021029709A1 KR 2020010782 W KR2020010782 W KR 2020010782W WO 2021029709 A1 WO2021029709 A1 WO 2021029709A1
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차용범
허동욱
홍성길
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주식회사 엘지화학
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Priority to CN202080041590.6A priority Critical patent/CN113924666B/en
Publication of WO2021029709A1 publication Critical patent/WO2021029709A1/en

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Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes.
  • a voltage is applied to the organic light emitting device having such a structure, electrons and electrons injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as 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. Meanwhile, 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 upon reduction is mainly used.
  • the light-emitting layer material a material having both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the emission layer are formed.
  • a material having high luminous efficiency that converts it to light when it is formed is preferable.
  • Patent Document 1 Korean Patent Publication No. 10-2006-0009932
  • an organic light-emitting device having a low driving voltage, high efficiency and/or long life characteristics is described.
  • An emission layer provided between the first electrode and the second electrode
  • a first organic material layer provided between the first electrode and the emission layer
  • An organic light emitting device comprising a second organic material layer provided between the second electrode and the light emitting layer,
  • the first organic material layer includes a compound represented by Formula 1 below,
  • the second organic material layer provides an organic light emitting device including a compound represented by Formula 2 below.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
  • At least one of X1 to X3 is N,
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substitute
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the organic light-emitting device of the present invention includes a compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the second organic material layer at the same time, thereby having a low driving voltage, high efficiency and/or long lifespan. Provides.
  • FIG. 1 shows an example of an organic light-emitting device including a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport and injection layer.
  • An example of an organic light-emitting device comprising (8) and a cathode (9) is shown.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
  • At least one of X1 to X3 is N,
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substitute
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • substituted means that the hydrogen atom bonded to the carbon atom of the 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, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Nitro group; Imide group; Amide group; Carbonyl group; Ether group; Ester group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Alkenyl group; Silyl group; Boron group; Amine group; Arylphosphine group; Phosphine oxide group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • a substituent to 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 to which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Silyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • substituted or unsubstituted refers to deuterium; Cyano group; Alkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the oxygen of the ester group is an alkyl group having 1 to 25 carbon atoms; An alkenyl group having 1 to 25 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it may be substituted with a heterocyclic group having 2 to 30 carbon atoms.
  • the oxygen is an alkyl group having 1 to 10 carbon atoms; An alkenyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or it is substituted with a C2-C20 heterocyclic group.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. Does not.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but are not limited thereto.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 20 carbon atoms.
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but 2 to 30; 2 to 20; 2 to 10; Or it is preferably 2 to 5.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of a straight chain or a branched form.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
  • the amine group is -NH 2 , and the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof may be substituted with the amine group.
  • the number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the amine group has 1 to 20 carbon atoms. According to an exemplary embodiment, the amine group has 1 to 10 carbon atoms.
  • substituted amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine Group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Although there are a ditolylamine group, a phenyltolylamine group, a diphenylamine group, etc., it is not limited to these.
  • the alkyl group in the alkylthioxy group and the alkylsulfoxy group is the same as the example of the alkyl group described above.
  • the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
  • the alkyl sulfoxy group is a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, and butyl.
  • sulfoxy groups are not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is limited thereto no.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
  • aryl group in the aryloxy group may be described above with respect to the aryl group.
  • the aryl group in the arylthioxy group and the arylsulfoxy group is the same as the example of the aryl group described above.
  • the heterocyclic group is a cyclic group including one or more of elements such as N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • heterocyclic group examples include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, etc., but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • ring in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group except for the divalent group.
  • the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups;
  • the hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms.
  • the heterocycle refers to a ring containing at least one selected from elements such as N, O, P, S, Si and Se.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • the aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms.
  • Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.
  • the aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms.
  • aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto.
  • the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.
  • the aliphatic heterocycle refers to an aliphatic ring containing at least one heteroatom.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, azocaine , Thiocane, and the like, but are not limited thereto.
  • the aromatic heterocycle means an aromatic ring containing at least one heteroatom.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothi
  • aryl group may be applied except that the arylene group is divalent.
  • heteroarylene group is divalent
  • description of the heteroaryl group may be applied.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tetracyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tetracyclic aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tricyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tricyclic aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; Terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl 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; A naphthyl group unsubstituted or substituted with an aryl group; A phenanthrenyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl 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 having 6 to 14 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; A phenanthrenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; Terphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; Or a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a terphenyl group unsubstituted or substituted with a methyl group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Phenanthrenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Or terphenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each may be independently selected from the following structures.
  • the dotted line indicates the bonding position.
  • R6 is an alkyl group or an aryl group.
  • R6 is an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • R6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • R6 is a methyl group or a phenyl group.
  • R6 is a methyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each may be independently selected from the following structures.
  • the dotted line indicates the bonding position.
  • Ar1 is represented by -L101-Ar101
  • Ar2 is represented by -L102-Ar102.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 60 carbon atoms.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylene group.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or a monocyclic to tetracyclic aryl group unsubstituted or substituted with a monocyclic to tetracyclic aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or a monocyclic to tricyclic aryl group unsubstituted or substituted with a monocyclic to tricyclic aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or an aryl group substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; Terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group;
  • a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a terphenyl group unsubstituted or substituted with a methyl group,
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Naphthyl group; Or a phenanthrenyl group.
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R1 is hydrogen; Or deuterium, or by bonding with adjacent groups to form an aromatic hydrocarbon ring condensed in the carbazole.
  • R1 is hydrogen, or is combined with an adjacent group to form an aromatic hydrocarbon ring condensed in carbazole.
  • R1 is hydrogen, or combines with an adjacent group to form a benzene ring condensed with carbazole.
  • R1 is hydrogen
  • R1 is combined with an adjacent group to form a benzene ring condensed with carbazole.
  • n is an integer of 1 to 8, and when n is 2 or more, two or more R1s are the same as or different from each other.
  • n 1
  • n is 2.
  • n 8.
  • Formula 1 is represented by the following Formula 1-1 or 1-2.
  • Formula 1 is represented by any one of the following Formulas 1-3 to 1-6.
  • G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • g1 is an integer from 1 to 10
  • g2 is an integer from 1 to 8
  • g1 is 2 or more, two or more G1s are the same as or different from each other, and when g2 is 2 or more, two or more G2s are the same or different from each other.
  • G1 and G2 are the same as or different from each other, and hydrogen; Or deuterium.
  • G1 and G2 are hydrogen.
  • g1 is 1.
  • g1 is 10.
  • g2 is 1.
  • g2 is 8.
  • the compound represented by Formula 1 is represented by any one of the following structural formulas.
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
  • At least one of X1 to X3 is N,
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substitute
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group.
  • L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L is a direct bond; Or a substituted or unsubstituted arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C12 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C10 arylene group.
  • L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L is a direct bond; Phenylene group; Or a biphenylene group.
  • L is a direct bond; Or a phenylene group.
  • L may be a direct bond or may be selected from one of the following structural formulas.
  • the dotted line indicates the bonding position.
  • R101 to R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R101 to R103 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R101 to R103 are the same as or different from each other, and each independently a methyl group or a phenyl group.
  • R101 and R102 are the same as or different from each other, and each independently a methyl group or a phenyl group.
  • R103 is a phenyl group.
  • L may be a direct bond or may be selected from one of the following structural formulas.
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13, and at least one of X1 to X3 is N.
  • At least one of X1 to X3 is N.
  • At least two of X1 to X3 are N.
  • X1, X2, and X3 are N.
  • X1 and X2 are N, and X3 is CR13.
  • X1 and X3 are N, and X2 is CR12.
  • X2 and X3 are N, and X1 is CR11.
  • X1 is N
  • X2 is CR12
  • X3 is CR13.
  • X2 is N
  • X1 is CR11
  • X3 is CR13.
  • X3 is N
  • X1 is CR11
  • X2 is CR12.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R11 to R13 are hydrogen; Or deuterium.
  • R11 to R13 are hydrogen.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted C 2 to C 15 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 6-cyclic aryl group; Or a substituted or unsubstituted monocyclic to 6 ring heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 5-cyclic aryl group; Or a substituted or unsubstituted monocyclic to 5-cyclic heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or two of the aforementioned substituents.
  • aryl group unsubstituted or substituted with a group connected above; Or a heteroaryl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected.
  • Ar3 and Ar4 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; Or a cyano group, an alkyl group or an aryl group substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 30 carbon atoms, or an aryl having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. group; Or a cyano group, a C1-C30 alkyl group, or a C2-C30 heteroaryl group unsubstituted or substituted with a C6-C30 aryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms group; Or a cyano group, a C1-C20 alkyl group, or a C2-C20 heteroaryl group unsubstituted or substituted with a C6-C20 aryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms group; Or a cyano group, an alkyl group having 1 to 5 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.
  • Ar3 and Ar4 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 phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or two of the aforementioned substituents.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Triphenylenyl group; Fluorenyl group; Spirobifluorenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group, and the groups may be unsubstituted or substituted with one or more groups from the group consisting of deuterium, halogen group, cyano group, alkylsilyl group, alkyl group and aryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; A biphenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A terphenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A triphenylenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A fluorenyl group
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms;
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group;
  • a biphenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a terphenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a naphthyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Spirobifluorenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group or a naphthyl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group or a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or terphenyl group.
  • Ar3 and Ar4 are the same as or different from each other, and each may be independently selected from the following structures.
  • the structure is unsubstituted or substituted with a cyano group or an alkyl group, and the dotted line indicates a bonding position.
  • the structure is unsubstituted or substituted with a cyano group or a methyl group.
  • R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • R6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R6 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R6 is a methyl group; Or a phenyl group.
  • R7 is a substituted or unsubstituted aryl group.
  • R7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R7 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R7 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
  • R7 is a phenyl group; Or a naphthyl group.
  • any one of Ar3 and Ar4 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 are a substituted or unsubstituted aryl group, and are different from each other.
  • Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-4 below.
  • the compound represented by Formula 2 is represented by any one of the following structural formulas.
  • 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 adjusted by introducing various substituents to the core structure of the above structure.
  • a first organic material layer is formed between the first electrode and the emission layer using the compound of Formula 1
  • a second organic material layer is formed between the second electrode and the emission layer using the compound of Formula 2. Except for this, it can be manufactured by a conventional method and material for manufacturing an organic light emitting device.
  • the compound 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, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light-emitting device of the present invention includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It can have a structure to 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.
  • the organic light-emitting device of the present invention includes a light-emitting layer, the first organic material layer provided between the first electrode and the light-emitting layer is represented by the compound represented by Formula 1, and the second organic material layer provided between the second electrode and the light-emitting layer is represented by formula 2. It includes a compound that becomes.
  • the thickness of the organic material layer including the compound of Formula 1 is 30 ⁇ to 300 ⁇ , preferably 50 ⁇ to 200 ⁇ .
  • the thickness of the organic material layer including the compound of Formula 2 is 30 ⁇ to 200 ⁇ , preferably 50 ⁇ to 100 ⁇ .
  • the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection And the transport layer includes the compound represented by Chemical Formula 1.
  • the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection layer.
  • the transport layer may include a compound represented by Chemical Formula 1.
  • the first organic material layer provided between the first electrode and the emission layer of the organic light emitting device of the present invention includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.
  • the first organic material layer provided between the first electrode and the emission layer of the organic light emitting device of the present invention may be an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 above.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer or the electron injection And the transport layer includes the compound represented by Chemical Formula 1.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention may be an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection layer.
  • the transport layer may include a compound represented by Chemical Formula 1.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 2.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention may be a hole blocking layer, and the hole blocking layer may include the compound represented by Formula 2.
  • the first organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1.
  • the second organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 2.
  • the organic light emitting device of the present invention further comprises at least one organic material layer among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • I can.
  • the first organic material layer is in contact with the emission layer.
  • the meaning of contact means that no other organic material layer exists between the light emitting layer and the first organic material layer.
  • the second organic material layer is in contact with the emission layer.
  • the meaning of contact means that no other organic material layer exists between the light emitting layer and the second organic material layer.
  • the organic material layer may include an electron blocking layer, and a material known in the art may be used for the electron blocking layer.
  • 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 organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9 are sequentially stacked.
  • the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the electron blocking layer 5, the light emitting layer 6, or the hole blocking layer 7.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport and injection layer.
  • the structure of an organic light-emitting device in which (8) and a cathode (9) are sequentially stacked is illustrated.
  • the compound represented by Formula 1 and the compound represented by Formula 2 are the hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), and hole blocking. It may be included in the layer 7 or the electron transport and injection layer 8.
  • the organic light-emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate.
  • PVD physical vapor deposition
  • an anode formed by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc. It may not have a single layer structure.
  • the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the anode material.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of receiving holes from the anode at a low voltage, and is a high occupied HOMO (highest occupied material) of the hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it.
  • the hole transport layer may serve to facilitate transport of holes.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a hole buffer layer may be additionally 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 emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • the light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding 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.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; 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 compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission dopants include 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), but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light emitting dopant is a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA),
  • a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the above-described compound or a material known in the art may be used for the hole blocking layer.
  • the electron transport layer may serve to facilitate transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage that can be.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for 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 compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the organic light emitting device may further include at least one hole blocking layer in addition to the hole blocking layer.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following compound [HI-1] and the following compound [HI-2] were thermally vacuum deposited to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) to form a hole injection layer.
  • [BH-1] and [BD-1] were vacuum-deposited at a weight ratio of 40:1 with a film thickness of 200 ⁇ to form a light emitting layer.
  • a hole blocking layer was formed by vacuum depositing the following compound [HB-1] with a film thickness of 50 ⁇ on the emission layer.
  • the compound [ET-1] and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 2,000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 2 ⁇ 10 ⁇ Maintaining 7 ⁇ 5 ⁇ 10 -6 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • the organic light emitting devices of Experimental Examples 1-1 to 1-12 basically exhibit characteristics of low voltage, high efficiency, and long life.
  • the compounds of Formula 1 have high efficiency
  • the compounds of Formula 2 It has the characteristics of long life.
  • the devices of Experimental Examples 1-1 to 1-12 showed a result that the luminous efficiency was increased by up to about 25% and the life was increased by up to about 150% compared to the comparative example.

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Abstract

The present specification provides an organic light-emitting device comprising a compound represented by chemical formula 1 and a compound represented by chemical formula 2.

Description

유기 발광 소자Organic light emitting element
본 출원은 2019년 8월 14일에 한국특허청에 제출된 한국 특허 출원 제10-2019-0099432호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0099432 filed with the Korean Intellectual Property Office on August 14, 2019, the entire contents of which are incorporated herein.
본 명세서는 유기 발광 소자에 관한 것이다.The present specification relates to an organic light emitting device.
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 device 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 electrons injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as 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 산화 시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 한편, 전자주입 물질이나 전자수송 물질로는 n-타입 성질을 가지는 유기 물질, 즉 쉽게 환원이 되고 환원 시에 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.Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as 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. Meanwhile, 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 upon reduction is mainly used. As the light-emitting layer material, a material having both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the emission layer are formed. A material having high luminous efficiency that converts it to 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, life, or efficiency of an organic light-emitting device, development of a material for an organic thin film is continuously required.
[선행기술문헌][Prior technical literature]
(특허문헌 1) 한국 특허 공개문헌 제10-2006-0009932호(Patent Document 1) Korean Patent Publication No. 10-2006-0009932
본 명세서에는 낮은 구동전압, 고효율 및/또는 장수명 특성을 갖는 유기 발광 소자가 기재된다.In the present specification, an organic light-emitting device having a low driving voltage, high efficiency and/or long life characteristics is described.
본 명세서의 일 실시상태는An exemplary embodiment of the present specification
제1 전극;A first electrode;
제2 전극;A second electrode;
상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층;An emission layer provided between the first electrode and the second electrode;
상기 제1 전극과 상기 발광층 사이에 구비된 제1 유기물층; 및A first organic material layer provided between the first electrode and the emission layer; And
상기 제2 전극과 상기 발광층 사이에 구비된 제2 유기물층을 포함하는 유기 발광 소자로서,An organic light emitting device comprising a second organic material layer provided between the second electrode and the light emitting layer,
상기 제1 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고,The first organic material layer includes a compound represented by Formula 1 below,
상기 제2 유기물층은 하기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.The second organic material layer provides an organic light emitting device including a compound represented by Formula 2 below.
[화학식 1][Formula 1]
Figure PCTKR2020010782-appb-I000001
Figure PCTKR2020010782-appb-I000001
상기 화학식 1에 있어서,In Formula 1,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기이고,Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
n은 1 내지 8의 정수이고, n이 2 이상인 경우 2 이상의 R1은 서로 동일하거나 상이하고,n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
[화학식 2][Formula 2]
Figure PCTKR2020010782-appb-I000002
Figure PCTKR2020010782-appb-I000002
상기 화학식 2에 있어서,In Formula 2,
L은 직접 결합; 치환 또는 비치환된 아릴렌기; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 2가의 알콕시기; 치환 또는 비치환된 2가의 알케닐기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
X1은 N; 또는 CR11이고, X2는 N; 또는 CR12이며, X3는 N; 또는 CR13이며,X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
X1 내지 X3 중 적어도 하나는 N이고,At least one of X1 to X3 is N,
R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 발명의 유기 발광 소자는 제1 유기물층에 화학식 1로 표시되는 화합물을 포함하고, 제2 유기물층에 화학식 2로 표시되는 화합물을 동시에 포함함으로써, 낮은 구동전압, 고효율 및/또는 장수명을 갖는 유기 발광 소자를 제공한다.The organic light-emitting device of the present invention includes a compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the second organic material layer at the same time, thereby having a low driving voltage, high efficiency and/or long lifespan. Provides.
도 1은 기판(1), 양극(2), 전자차단층(5), 발광층(6), 정공차단층(7) 및 음극(9)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light-emitting device including a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9.
도 2는 기판 (1), 양극(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송 및 주입층(8) 및 음극(9)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport and injection layer. An example of an organic light-emitting device comprising (8) and a cathode (9) is shown.
[부호의 설명][Explanation of code]
1: 기판1: substrate
2: 양극2: anode
3: 정공주입층3: hole injection layer
4: 정공수송층4: hole transport layer
5: 전자차단층5: electron blocking layer
6: 발광층6: light emitting layer
7: 정공차단층7: hole blocking layer
8: 전자수송 및 주입층8: electron transport and injection layer
9: 음극9: cathode
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present specification will be described in more detail.
본 명세서에서는 제1 전극; 제2 전극; 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 상기 제1 전극과 상기 발광층 사이에 구비된 제1 유기물층; 및 상기 제2 전극과 상기 발광층 사이에 구비된 제2 유기물층을 포함하는 유기 발광 소자로서, 상기 제1 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고, 상기 제2 유기물층은 하기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.In the present specification, the first electrode; A second electrode; An emission layer provided between the first electrode and the second electrode; A first organic material layer provided between the first electrode and the emission layer; And a second organic material layer provided between the second electrode and the emission layer, wherein the first organic material layer includes a compound represented by Formula 1 below, and the second organic material layer is represented by Formula 2 below. It provides an organic light-emitting device comprising a compound.
[화학식 1][Formula 1]
Figure PCTKR2020010782-appb-I000003
Figure PCTKR2020010782-appb-I000003
상기 화학식 1에 있어서,In Formula 1,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기이고,Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
n은 1 내지 8의 정수이고, n이 2 이상인 경우 2 이상의 R1은 서로 동일하거나 상이하고,n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
[화학식 2][Formula 2]
Figure PCTKR2020010782-appb-I000004
Figure PCTKR2020010782-appb-I000004
상기 화학식 2에 있어서,In Formula 2,
L은 직접 결합; 치환 또는 비치환된 아릴렌기; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 2가의 알콕시기; 치환 또는 비치환된 2가의 알케닐기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
X1은 N; 또는 CR11이고, X2는 N; 또는 CR12이며, X3는 N; 또는 CR13이며,X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
X1 내지 X3 중 적어도 하나는 N이고,At least one of X1 to X3 is N,
R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서에 있어서, 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.
본 명세서에 있어서, 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 the case where the member is in contact with the other member, but also the case where another member exists between the two members.
본 명세서에 있어서,
Figure PCTKR2020010782-appb-I000005
는 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification,
Figure PCTKR2020010782-appb-I000005
Means a position bonded to a chemical formula or compound.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituent in the present specification are described below, but are not limited thereto.
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.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the 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, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 이미드기; 아미드기; 카르보닐기; 에테르기; 에스테르기; 히드록시기; 알킬기; 시클로알킬기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 알케닐기; 실릴기; 붕소기; 아민기; 아릴포스핀기; 포스핀옥사이드기; 아릴기; 및 헤테로아릴기로 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 있다. In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Imide group; Amide group; Carbonyl group; Ether group; Ester group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Alkenyl group; Silyl group; Boron group; Amine group; Arylphosphine group; Phosphine oxide group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to 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 to which two phenyl groups are connected.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 알킬기; 시클로알킬기; 실릴기; 아릴기; 및 헤테로아릴기로 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.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Silyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 시아노기; 알킬기; 아릴기; 및 헤테로아릴기로 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.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Cyano group; Alkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.
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 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
Figure PCTKR2020010782-appb-I000006
Figure PCTKR2020010782-appb-I000006
본 명세서에 있어서, 에스테르기는 -C(=O)OR105, 또는 -OC(=O)R106 이 될 수 있으며, 상기 R105 및 R106는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 시클로알킬기, 또는 치환 또는 비치환된 아릴기이나, 이에 한정되는 것은 아니다. 구체적으로, 에스테르기의 산소가 탄소수 1 내지 25의 알킬기; 탄소수 1 내지 25의 알케닐기; 탄소수 6 내지 30의 아릴기; 또는 탄소수 2 내지 30의 헤테로고리기로 치환될 수 있다. 본 명세서의 일 실시상태에 있어서, 상기 산소가 탄소수 1 내지 10의 알킬기; 탄소수 1 내지 10의 알케닐기; 탄소수 6 내지 20의 아릴기; 또는 탄소수 2 내지 20의 헤테로고리기로 치환된다.In the present specification, the ester group may be -C(=O)OR 105 , or -OC(=O)R 106 , and R 105 and R 106 are the same as or different from each other, and each independently hydrogen, substituted or An unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, but is not limited thereto. Specifically, the oxygen of the ester group is an alkyl group having 1 to 25 carbon atoms; An alkenyl group having 1 to 25 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it may be substituted with a heterocyclic group having 2 to 30 carbon atoms. In the exemplary embodiment of the present specification, the oxygen is an alkyl group having 1 to 10 carbon atoms; An alkenyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or it is substituted with a C2-C20 heterocyclic group.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다. In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
Figure PCTKR2020010782-appb-I000007
Figure PCTKR2020010782-appb-I000007
본 명세서에 있어서, 아미드기는 아미드기의 질소가 수소, 탄소수 1 내지 30의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
Figure PCTKR2020010782-appb-I000008
Figure PCTKR2020010782-appb-I000008
본 명세서에 있어서, 실릴기는 -SiYaYbYc의 화학식으로 표시될 수 있고, 상기 Ya, Yb 및 Yc는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. Does not.
본 명세서에 있어서, 붕소기는 -BYdYe의 화학식으로 표시될 수 있고, 상기 Yd 및 Ye는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, 펜틸기, n-펜틸기, 헥실기, n-헥실기, 헵틸기, n-헵틸기, 옥틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, i-프로필옥시, 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 linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, i-propyloxy, 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 are not limited thereto.
본 명세서에 있어서, 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 2 내지 30; 2 내지 20; 2 내지 10; 또는 2 내지 5인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but 2 to 30; 2 to 20; 2 to 10; Or it is preferably 2 to 5. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 기재된 알킬기, 알콕시기 및 그 외 알킬기 부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다.Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of a straight chain or a branched form.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 아민기는 -NH2이며, 상기 아민기에는 전술한 알킬기, 아릴기, 헤테로고리기, 알케닐기, 시클로알킬기 및 이들의 조합 등이 치환될 수 있다. 상기 치환된 아민기의 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 일 실시상태에 따르면, 상기 아민기의 탄소수는 1 내지 20이다. 일 실시상태에 따르면, 상기 아민기의 탄소수는 1 내지 10이다. 치환된 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 9,9-디메틸플루오레닐페닐아민기, 피리딜페닐아민기, 디페닐아민기, 페닐피리딜아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 디벤조퓨라닐페닐아민기, 9-메틸안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 디페닐아민기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 , and the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof may be substituted with the amine group. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the amine group has 1 to 20 carbon atoms. According to an exemplary embodiment, the amine group has 1 to 10 carbon atoms. Specific examples of the substituted amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine Group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Although there are a ditolylamine group, a phenyltolylamine group, a diphenylamine group, etc., it is not limited to these.
본 명세서에 있어서, 알킬티옥시기 및 알킬술폭시기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert－부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메틸술폭시기, 에틸술폭시기, 프로필술폭시기, 부틸술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group in the alkylthioxy group and the alkylsulfoxy group is the same as the example of the alkyl group described above. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group is a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, and butyl. There are sulfoxy groups, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기, 쿼터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기, 트리페닐레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is limited thereto no.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2020010782-appb-I000009
,
Figure PCTKR2020010782-appb-I000010
등의 스피로플루오레닐기,
Figure PCTKR2020010782-appb-I000011
(9,9-디메틸플루오레닐기), 및
Figure PCTKR2020010782-appb-I000012
(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2020010782-appb-I000009
,
Figure PCTKR2020010782-appb-I000010
Spirofluorenyl groups such as,
Figure PCTKR2020010782-appb-I000011
(9,9-dimethylfluorenyl group), and
Figure PCTKR2020010782-appb-I000012
It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
본 명세서에 있어서, 아릴옥시기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aryloxy group may be described above with respect to the aryl group.
본 명세서에 있어서, 아릴티옥시기 및 아릴술폭시기 중의 아릴기는 전술한 아릴기의 예시와 같다.In the present specification, the aryl group in the arylthioxy group and the arylsulfoxy group is the same as the example of the aryl group described above.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, P, S, Si 및 Se 등의 원소 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로고리기의 예로는 예로는 피리딘기, 피롤기, 피리미딘기, 퀴놀린기, 피리다지닐기, 퓨란기, 티오펜기, 이미다졸기, 피라졸기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 벤조카바졸기, 나프토벤조퓨란기, 벤조나프토티오펜기, 인데노카바졸기, 트리아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a cyclic group including one or more of elements such as N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, etc., but are not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, 인접한 기와 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 탄화수소 고리; 또는 헤테로 고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.
상기 탄화수소 고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 2가기인 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.The hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group except for the divalent group.
본 명세서에 있어서, 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 지방족 헤테로고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 이들의 축합고리를 형성하는 것을 의미한다. 상기 탄화수소고리는 탄소와 수소 원자로만 이루어진 고리를 의미한다. 상기 헤테로고리는 N, O, P, S, Si 및 Se 등의 원소 중에서 선택된 1 이상으로 포함하는 고리를 의미한다. 본 명세서에 있어서, 상기 지방족 탄화수소고리, 방향족 탄화수소고리, 지방족 헤테로고리 및 방향족 헤테로고리는 단환 또는 다환일 수 있다.In the present specification, the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these. The hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The heterocycle refers to a ring containing at least one selected from elements such as N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
본 명세서에 있어서, 지방족 탄화수소고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미한다. 지방족 탄화수소고리의 예로는 시클로프로판, 시클로부탄, 시클로부텐, 시클로펜탄, 시클로펜텐, 시클로헥산, 시클로헥센, 1,4-시클로헥사디엔, 시클로헵탄, 시클로헵텐, 시클로옥탄, 시클로옥텐 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.
본 명세서에 있어서, 방향족 탄화수소고리란 탄소와 수소 원자로만 이루어진 방향족의 고리를 의미한다. 방향족 탄화수소고리의 예로는 벤젠, 나프탈렌, 안트라센, 페난트렌, 페릴렌, 플루오란텐, 트리페닐렌, 페날렌, 파이렌, 테트라센, 크라이센, 펜타센, 플루오렌, 인덴, 아세나프틸렌, 벤조플루오렌, 스피로플루오렌 등이 있으나, 이에 한정되지 않는다. 본 명세서에 있어서, 방향족 탄화수소고리는 아릴기와 동일한 의미로 해석될 수 있다.In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic heterocycle refers to an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, azocaine , Thiocane, and the like, but are not limited thereto.
본 명세서에 있어서, 방향족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 방향족 고리를 의미한다. 방향족 헤테로고리의 예로는, 피리딘, 피롤, 피리미딘, 피리다진, 퓨란, 티오펜, 이미다졸, 파라졸, 옥사졸, 이소옥사졸, 티아졸, 이소티아졸, 트리아졸, 옥사디아졸, 티아디아졸, 디티아졸, 테트라졸, 피란, 티오피란, 디아진, 옥사진, 티아진, 다이옥신, 트리아진, 테트라진, 이소퀴놀린, 퀴놀린, 퀴논, 퀴나졸린, 퀴녹살린, 나프티리딘, 아크리딘, 페난트리딘, 디아자나프탈렌, 드리아자인덴, 인돌, 인돌리진, 벤조티아졸, 벤조옥사졸, 벤조이미다졸, 벤조티오펜, 벤조퓨란, 디벤조티오펜, 디벤조퓨란, 카바졸, 벤조카바졸, 디벤조카바졸, 페나진, 이미다조피리딘, 페녹사진, 인돌로카바졸, 인데노카바졸 등이 있으나, 이에 한정되지 않는다.In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.
상기 아릴렌기는 2가인 것을 제외하고는 상기 아릴기에 대한 설명이 적용될 수 있다.The description of the aryl group may be applied except that the arylene group is divalent.
상기 헤테로아릴렌기는 2가인 것을 제외하고는 상기 헤테로아릴기에 대한 설명이 적용될 수 있다.Except that the heteroarylene group is divalent, the description of the heteroaryl group may be applied.
이하 본 발명의 바람직한 실시상태를 상세히 설명한다. 그러나 본 발명의 실시상태는 여러 가지 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 설명하는 실시상태들에 한정되지는 않는다.Hereinafter, a preferred embodiment of the present invention will be described in detail. However, exemplary embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the exemplary embodiments described below.
이하, 화학식 1에 대하여 상세히 설명한다.Hereinafter, Formula 1 will be described in detail.
[화학식 1][Formula 1]
Figure PCTKR2020010782-appb-I000013
Figure PCTKR2020010782-appb-I000013
상기 화학식 1에 있어서,In Formula 1,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기이고,Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
n은 1 내지 8의 정수이고, n이 2 이상인 경우 2 이상의 R1은 서로 동일하거나 상이하다.n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기이다.According to 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 unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 단환 내지 4환의 아릴기로 치환 또는 비치환된 단환 내지 4환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tetracyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tetracyclic aryl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 단환 내지 3환의 아릴기로 치환 또는 비치환된 단환 내지 3환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tricyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tricyclic aryl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 단환 내지 2환의 아릴기로 치환 또는 비치환된 단환 내지 2환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 60의 알킬기 또는 탄소수 6 내지 60의 아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 10의 알킬기 또는 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 페닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 바이페닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 나프틸기; 알킬기 또는 아릴기로 치환 또는 비치환된 페난트레닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 터페닐기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기이다.According to 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 alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; Terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 아릴기로 치환 또는 비치환된 페닐기; 아릴기로 치환 또는 비치환된 바이페닐기; 아릴기로 치환 또는 비치환된 나프틸기; 아릴기로 치환 또는 비치환된 페난트레닐기; 아릴기로 치환 또는 비치환된 터페닐기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기이다.According to 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; A naphthyl group unsubstituted or substituted with an aryl group; A phenanthrenyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 바이페닐기; 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 나프틸기; 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 페난트레닐기; 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 터페닐기; 또는 탄소수 1 내지 10의 알킬기 또는 탄소수 6 내지 14의 아릴기로 치환 또는 비치환된 플루오레닐기이다.According to 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 having 6 to 14 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; A phenanthrenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; Terphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; Or a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 바이페닐기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 나프틸기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페난트레닐기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 터페닐기; 또는 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 플루오레닐기이다.According to 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 methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 바이페닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페난트레닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 터페닐기; 또는 메틸기로 치환 또는 비치환된 플루오레닐기이다.According to 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 phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 나프틸기; 페난트레닐기; 터페닐기; 또는 메틸기로 치환 또는 비치환된 플루오레닐기이다.According to 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 phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 페난트레닐기; 터페닐기; 또는 디메틸 플루오레닐기이다.According to 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 phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Phenanthrenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 터페닐기; 또는 디메틸 플루오레닐기이다.According to 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 phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 또는 터페닐기이다.According to 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 phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Or terphenyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조 중에서 선택될 수 있다.According to the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each may be independently selected from the following structures.
Figure PCTKR2020010782-appb-I000014
Figure PCTKR2020010782-appb-I000014
상기 구조에 있어서, 점선은 결합 위치를 나타낸다.In the above structure, the dotted line indicates the bonding position.
상기 구조에서, R6은 알킬기 또는 아릴기이다.In the above structure, R6 is an alkyl group or an aryl group.
상기 구조에서, R6은 탄소수 1 내지 30의 알킬기 또는 탄소수 6 내지 30의 아릴기이다.In the above structure, R6 is an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
상기 구조에서, R6은 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기이다.In the above structure, R6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
상기 구조에서, R6은 메틸기 또는 페닐기이다.In the above structure, R6 is a methyl group or a phenyl group.
상기 구조에서, R6은 메틸기이다.In the above structure, R6 is a methyl group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조 중에서 선택될 수 있다.According to the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each may be independently selected from the following structures.
Figure PCTKR2020010782-appb-I000015
Figure PCTKR2020010782-appb-I000015
상기 구조에 있어서, 점선은 결합 위치를 나타낸다.In the above structure, the dotted line indicates the bonding position.
본 명세서의 일 실시상태에 따르면, Ar1은 -L101-Ar101로 표시되고, Ar2는 -L102-Ar102로 표시된다.According to an exemplary embodiment of the present specification, Ar1 is represented by -L101-Ar101, and Ar2 is represented by -L102-Ar102.
본 명세서의 일 실시상태에 따르면, L101 및 L102는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 아릴렌기이다.According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group.
본 명세서의 일 실시상태에 따르면, L101 및 L102는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 탄소수 6 내지 60의 아릴렌기이다.According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, L101 및 L102는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 탄소수 6 내지 30의 아릴렌기이다.According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, L101 및 L102는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이다.According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, L101 및 L102는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 또는 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylene group.
본 명세서의 일 실시상태에 따르면, L101 및 L102는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌기이다.According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 60의 알킬기 또는 탄소수 6 내지 60의 아릴기로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 단환 내지 4환의 아릴기로 치환 또는 비치환된 단환 내지 4환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or a monocyclic to tetracyclic aryl group unsubstituted or substituted with a monocyclic to tetracyclic aryl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 단환 내지 3환의 아릴기로 치환 또는 비치환된 단환 내지 3환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or a monocyclic to tricyclic aryl group unsubstituted or substituted with a monocyclic to tricyclic aryl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 단환 내지 2환의 아릴기로 치환 또는 비치환된 단환 내지 2환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 페닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 바이페닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 나프틸기; 알킬기 또는 아릴기로 치환 또는 비치환된 페난트레닐기; 알킬기 또는 아릴기로 치환 또는 비치환된 터페닐기; 또는 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or an aryl group substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; Terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 바이페닐기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 나프틸기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페난트레닐기; 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 터페닐기; 또는 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 바이페닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페난트레닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 터페닐기; 또는 메틸기로 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 나프틸기; 페난트레닐기; 터페닐기; 또는 메틸기로 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 나프틸기; 페난트레닐기; 터페닐기; 또는 디메틸 플루오레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 바이페닐기; 터페닐기; 나프틸기; 페난트레닐기; 또는 메틸기로 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
본 명세서의 일 실시상태에 따르면, Ar101 및 Ar102는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 나프틸기; 또는 페난트레닐기이다.According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Naphthyl group; Or a phenanthrenyl group.
본 명세서의 일 실시상태에 따르면, R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.[0366] According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소 고리를 형성한다.[0366] According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, R1은 수소; 또는 중수소이거나, 인접한 기와 서로 결합하여 카바졸에 축합되는 방향족 탄화수소 고리를 형성한다.[0366] According to an exemplary embodiment of the present specification, R1 is hydrogen; Or deuterium, or by bonding with adjacent groups to form an aromatic hydrocarbon ring condensed in the carbazole.
본 명세서의 일 실시상태에 따르면, R1은 수소이거나, 인접한 기와 서로 결합하여 카바졸에 축합되는 방향족 탄화수소 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen, or is combined with an adjacent group to form an aromatic hydrocarbon ring condensed in carbazole.
본 명세서의 일 실시상태에 따르면, R1은 수소이거나, 인접한 기와 서로 결합하여 카바졸에 축합되는 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen, or combines with an adjacent group to form a benzene ring condensed with carbazole.
본 명세서의 일 실시상태에 따르면, R1은 수소이다.According to an exemplary embodiment of the present specification, R1 is hydrogen.
본 명세서의 일 실시상태에 따르면, R1은 인접한 기와 서로 결합하여 카바졸에 축합되는 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is combined with an adjacent group to form a benzene ring condensed with carbazole.
본 명세서의 일 실시상태에 따르면, n은 1 내지 8의 정수이고, n이 2 이상인 경우 2 이상의 R1은 서로 동일하거나 상이하다.According to an exemplary embodiment of the present specification, n is an integer of 1 to 8, and when n is 2 or more, two or more R1s are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, n은 1이다.According to an exemplary embodiment of the present specification, n is 1.
본 명세서의 일 실시상태에 따르면, n은 2이다.According to an exemplary embodiment of the present specification, n is 2.
본 명세서의 일 실시상태에 따르면, n은 8이다.According to an exemplary embodiment of the present specification, n is 8.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, 아민기에 연결된 바이페닐렌기의 ortho 위치 또는 meta 위치에 카바졸의 N이 연결되는 경우, 전압, 효율 또는 수명 특성이 더욱 증가하는 결과를 나타낸다.According to an exemplary embodiment of the present specification, in Formula 1, when N of carbazole is connected to the ortho position or meta position of the biphenylene group connected to the amine group, voltage, efficiency, or lifespan characteristics are further increased. .
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1 or 1-2.
[화학식 1-1][Formula 1-1]
Figure PCTKR2020010782-appb-I000016
Figure PCTKR2020010782-appb-I000016
[화학식 1-2][Formula 1-2]
Figure PCTKR2020010782-appb-I000017
Figure PCTKR2020010782-appb-I000017
상기 화학식 1-1 및 1-2에 있어서, Ar1, Ar2, R1 및 n의 정의는 상기 화학식 1에서의 정의와 같다.In Formulas 1-1 and 1-2, the definitions of Ar1, Ar2, R1 and n are the same as those in Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-3 내지 1-6 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-3 to 1-6.
[화학식 1-3][Formula 1-3]
Figure PCTKR2020010782-appb-I000018
Figure PCTKR2020010782-appb-I000018
[화학식 1-4][Formula 1-4]
Figure PCTKR2020010782-appb-I000019
Figure PCTKR2020010782-appb-I000019
[화학식 1-5][Formula 1-5]
Figure PCTKR2020010782-appb-I000020
Figure PCTKR2020010782-appb-I000020
[화학식 1-6][Formula 1-6]
Figure PCTKR2020010782-appb-I000021
Figure PCTKR2020010782-appb-I000021
상기 화학식 1-3 내지 1-6에 있어서, Ar1 및 Ar2의 정의는 상기 화학식 1에서의 정의와 같고,In Formulas 1-3 to 1-6, the definitions of Ar1 and Ar2 are the same as those in Formula 1,
G1 및 G2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
g1은 1 내지 10의 정수이고,g1 is an integer from 1 to 10,
g2는 1 내지 8의 정수이고,g2 is an integer from 1 to 8,
g1이 2 이상인 경우, 2 이상의 G1은 서로 동일하거나 상이하고, g2가 2 이상인 경우, 2 이상의 G2는 서로 동일하거나 상이하다.When g1 is 2 or more, two or more G1s are the same as or different from each other, and when g2 is 2 or more, two or more G2s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, G1 및 G2는 서로 동일하거나 상이하고, 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, G1 및 G2는 수소이다.According to an exemplary embodiment of the present specification, G1 and G2 are hydrogen.
본 명세서의 일 실시상태에 따르면, g1은 1이다.According to an exemplary embodiment of the present specification, g1 is 1.
본 명세서의 일 실시상태에 따르면, g1은 10이다.According to an exemplary embodiment of the present specification, g1 is 10.
본 명세서의 일 실시상태에 따르면, g2는 1이다.According to an exemplary embodiment of the present specification, g2 is 1.
본 명세서의 일 실시상태에 따르면, g2는 8이다.According to an exemplary embodiment of the present specification, g2 is 8.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 하기 구조식 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by any one of the following structural formulas.
Figure PCTKR2020010782-appb-I000022
Figure PCTKR2020010782-appb-I000022
Figure PCTKR2020010782-appb-I000023
Figure PCTKR2020010782-appb-I000023
Figure PCTKR2020010782-appb-I000024
Figure PCTKR2020010782-appb-I000024
Figure PCTKR2020010782-appb-I000025
Figure PCTKR2020010782-appb-I000025
Figure PCTKR2020010782-appb-I000026
Figure PCTKR2020010782-appb-I000026
이하, 화학식 2에 대하여 상세히 설명한다.Hereinafter, Formula 2 will be described in detail.
[화학식 2][Formula 2]
Figure PCTKR2020010782-appb-I000027
Figure PCTKR2020010782-appb-I000027
상기 화학식 2에 있어서,In Formula 2,
L은 직접 결합; 치환 또는 비치환된 아릴렌기; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 2가의 알콕시기; 치환 또는 비치환된 2가의 알케닐기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
X1은 N; 또는 CR11이고, X2는 N; 또는 CR12이며, X3는 N; 또는 CR13이며,X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
X1 내지 X3 중 적어도 하나는 N이고,At least one of X1 to X3 is N,
R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 치환 또는 비치환된 아릴렌기; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 2가의 알콕시기; 치환 또는 비치환된 2가의 알케닐기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 치환 또는 비치환된 탄소수 6 내지 12의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C12 arylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 치환 또는 비치환된 탄소수 6 내지 10의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6 to C10 arylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 페닐렌기; 또는 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Phenylene group; Or a biphenylene group.
본 명세서의 일 실시상태에 따르면, L은 직접 결합; 또는 페닐렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; Or a phenylene group.
본 명세서의 일 실시상태에 따르면, L은 직접결합이거나, 하기 구조식 중 어느 하나로 선택될 수 있다.According to an exemplary embodiment of the present specification, L may be a direct bond or may be selected from one of the following structural formulas.
Figure PCTKR2020010782-appb-I000028
Figure PCTKR2020010782-appb-I000028
상기 구조에 있어서, 점선은 결합 위치를 나타낸다.In the above structure, the dotted line indicates the bonding position.
상기 구조에서, R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In the above structure, R101 to R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 따르면, R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 메틸기 또는 페닐기이다.According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently a methyl group or a phenyl group.
본 명세서의 일 실시상태에 따르면, R101 및 R102는 서로 같거나 상이하고, 각각 독립적으로 메틸기 또는 페닐기이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a methyl group or a phenyl group.
본 명세서의 일 실시상태에 따르면, R103은 페닐기이다.According to an exemplary embodiment of the present specification, R103 is a phenyl group.
본 명세서의 일 실시상태에 따르면, L은 직접결합이거나, 하기 구조식 중 어느 하나로 선택될 수 있다.According to an exemplary embodiment of the present specification, L may be a direct bond or may be selected from one of the following structural formulas.
Figure PCTKR2020010782-appb-I000029
Figure PCTKR2020010782-appb-I000029
상기 구조식에서, 점선은 결합 위치를 나타낸다.In the above structural formula, the dotted line indicates the bonding position.
본 명세서의 일 실시상태에 따르면, X1은 N; 또는 CR11이고, X2는 N; 또는 CR12이며, X3는 N; 또는 CR13이며, X1 내지 X3 중 적어도 하나는 N이다.According to an exemplary embodiment of the present specification, X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13, and at least one of X1 to X3 is N.
본 명세서의 일 실시상태에 따르면, X1 내지 X3 중 적어도 하나는 N이다.According to an exemplary embodiment of the present specification, at least one of X1 to X3 is N.
본 명세서의 일 실시상태에 따르면, X1 내지 X3 중 적어도 2개는 N이다.According to an exemplary embodiment of the present specification, at least two of X1 to X3 are N.
본 명세서의 일 실시상태에 따르면, X1, X2 및 X3는 N이다.According to an exemplary embodiment of the present specification, X1, X2, and X3 are N.
본 명세서의 일 실시상태에 따르면, X1 및 X2는 N이고, X3는 CR13이다.According to an exemplary embodiment of the present specification, X1 and X2 are N, and X3 is CR13.
본 명세서의 일 실시상태에 따르면, X1 및 X3은 N이고, X2는 CR12이다.According to an exemplary embodiment of the present specification, X1 and X3 are N, and X2 is CR12.
본 명세서의 일 실시상태에 따르면, X2 및 X3는 N이고, X1은 CR11이다.According to an exemplary embodiment of the present specification, X2 and X3 are N, and X1 is CR11.
본 명세서의 일 실시상태에 따르면, X1은 N이고, X2는 CR12이고, X3는 CR13이다.According to an exemplary embodiment of the present specification, X1 is N, X2 is CR12, and X3 is CR13.
본 명세서의 일 실시상태에 따르면, X2는 N이고, X1은 CR11이고, X3는 CR13이다.According to an exemplary embodiment of the present specification, X2 is N, X1 is CR11, and X3 is CR13.
본 명세서의 일 실시상태에 따르면, X3는 N이고, X1은 CR11이고, X2는 CR12이다.According to an exemplary embodiment of the present specification, X3 is N, X1 is CR11, and X2 is CR12.
본 명세서의 일 실시상태에 따르면, R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
본 명세서의 일 실시상태에 따르면, R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
본 명세서의 일 실시상태에 따르면, R11 내지 R13은 수소; 또는 중수소이다.[0343] According to an exemplary embodiment of the present specification, R11 to R13 are hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, R11 내지 R13은 수소이다.According to an exemplary embodiment of the present specification, R11 to R13 are hydrogen.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 15의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 15의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted C 2 to C 15 heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 10의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 10의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 6환의 아릴기; 또는 치환 또는 비치환된 단환 내지 6환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 6-cyclic aryl group; Or a substituted or unsubstituted monocyclic to 6 ring heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 5환의 아릴기; 또는 치환 또는 비치환된 단환 내지 5환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 5-cyclic aryl group; Or a substituted or unsubstituted monocyclic to 5-cyclic heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 단환 내지 4환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 3환의 아릴기; 또는 치환 또는 비치환된 단환 내지 3환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 아릴기; 또는 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or two of the aforementioned substituents. An aryl group unsubstituted or substituted with a group connected above; Or a heteroaryl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; Or a cyano group, an alkyl group or an aryl group substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 탄소수 1 내지 30의 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 시아노기, 탄소수 1 내지 30의 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 30 carbon atoms, or an aryl having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. group; Or a cyano group, a C1-C30 alkyl group, or a C2-C30 heteroaryl group unsubstituted or substituted with a C6-C30 aryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 2 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms group; Or a cyano group, a C1-C20 alkyl group, or a C2-C20 heteroaryl group unsubstituted or substituted with a C6-C20 aryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 탄소수 1 내지 5의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 시아노기, 탄소수 1 내지 5의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 2 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms group; Or a cyano group, an alkyl group having 1 to 5 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 스피로바이플루오레닐기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 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 phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 페닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 바이페닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 터페닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 나프틸기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 페난트레닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 트리페닐레닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 플루오레닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 스피로바이플루오레닐기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 디벤조퓨란기; 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 디벤조티오펜기; 또는 중수소, 할로겐기, 시아노기, 실릴기, 알킬기 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 전술한 치환기 중 2 이상이 연결된 기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or two of the aforementioned substituents. A phenyl group unsubstituted or substituted with a group connected above; A biphenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A terphenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A naphthyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A phenanthrenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A triphenylenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A fluorenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A spirobifluorenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A dibenzofuran group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; A dibenzothiophene group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected; Or a carbazole group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 바이페닐기; 터페닐기; 나프틸기; 페난트레닐기; 트리페닐레닐기; 플루오레닐기; 스피로바이플루오레닐기; 디벤조퓨란기; 디벤조티오펜기; 또는 카바졸기이고, 상기 기들은 중수소, 할로겐기, 시아노기, 알킬실릴기, 알킬기 및 아릴기로 이루어진 군에서 1 이상의 기로 치환 또는 비치환될 수 있다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Triphenylenyl group; Fluorenyl group; Spirobifluorenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group, and the groups may be unsubstituted or substituted with one or more groups from the group consisting of deuterium, halogen group, cyano group, alkylsilyl group, alkyl group and aryl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 페닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 바이페닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 터페닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 나프틸기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 페난트레닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 트리페닐레닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 플루오레닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 스피로비플루오레닐기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 카바졸기; 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 디벤조퓨란기; 또는 시아노기, 알킬기 또는 아릴기로 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; A biphenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A terphenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A triphenylenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A fluorenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A spirobifluorenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A carbazole group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; Dibenzofuran group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; Or a cyano group, an alkyl group or an aryl group substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 페닐기; 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 바이페닐기; 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 터페닐기; 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 나프틸기; 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 페난트레닐기; 시아노기, 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 트리페닐레닐기; 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 플루오레닐기; 스피로바이플루오레닐기; 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 카바졸기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; A terphenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; A phenanthrenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; A triphenylenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; A fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Spirobifluorenyl group; A carbazole group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Dibenzofuran group; Or a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 바이페닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 터페닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 나프틸기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페난트레닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 트리페닐레닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 플루오레닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 스피로바이플루오레닐기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 디벤조퓨란기; 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 디벤조티오펜기; 또는 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A triphenylenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A fluorenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A spirobifluorenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A dibenzofuran group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A dibenzothiophene group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; Or a cyano group, a methyl group, a phenyl group, a naphthyl group, or a carbazole group unsubstituted or substituted with a phenanthrenyl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시아노기, 메틸기, 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 바이페닐기; 터페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 페난트레닐기; 트리페닐레닐기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 스피로바이플루오레닐기; 디벤조퓨란기; 디벤조티오펜기; 또는 페닐기 또는 나프틸기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Spirobifluorenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group or a naphthyl group.
본 명세서의 일 실시상태에 따르면, Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기 또는 나프틸기로 치환 또는 비치환된 페닐기; 바이페닐기; 또는 터페닐기이다.According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group or a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or terphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조 중에서 선택될 수 있다.According to the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each may be independently selected from the following structures.
Figure PCTKR2020010782-appb-I000030
Figure PCTKR2020010782-appb-I000030
상기 구조는 시아노기 또는 알킬기로 치환 또는 비치환되고, 점선은 결합 위치를 나타낸다.The structure is unsubstituted or substituted with a cyano group or an alkyl group, and the dotted line indicates a bonding position.
상기 구조는 시아노기 또는 메틸기로 치환 또는 비치환된다.The structure is unsubstituted or substituted with a cyano group or a methyl group.
상기 구조에서, R6은 치환 또는 비치환된 알킬기 또는 치환 또는 비치환된 아릴기이다.In the above structure, R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
상기 구조에서, R6은 치환 또는 비치환된 탄소수 1 내지 30의 알킬기 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the above structure, R6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
상기 구조에서, R6은 치환 또는 비치환된 탄소수 1 내지 20의 알킬기 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the above structure, R6 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
상기 구조에서, R6은 메틸기; 또는 페닐기이다.In the above structure, R6 is a methyl group; Or a phenyl group.
상기 구조에서, R7은 치환 또는 비치환된 아릴기이다.In the above structure, R7 is a substituted or unsubstituted aryl group.
상기 구조에서, R7은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In the above structure, R7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
상기 구조에서, R7은 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In the above structure, R7 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
상기 구조에서, R7은 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 나프틸기이다.In the above structure, R7 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
상기 구조에서, R7은 페닐기; 또는 나프틸기이다.In the above structure, R7 is a phenyl group; Or a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar3 및 Ar4 중 어느 하나는 치환 또는 비치환된 아릴기이고, 다른 하나는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, any one of Ar3 and Ar4 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar3 및 Ar4 는 치환 또는 비치환된 아릴기이고, 서로 상이하다.According to the exemplary embodiment of the present specification, Ar3 and Ar4 are a substituted or unsubstituted aryl group, and are different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2는 하기 화학식 2-1 내지 2-4 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-4 below.
[화학식 2-1][Formula 2-1]
Figure PCTKR2020010782-appb-I000031
Figure PCTKR2020010782-appb-I000031
[화학식 2-2][Formula 2-2]
Figure PCTKR2020010782-appb-I000032
Figure PCTKR2020010782-appb-I000032
[화학식 2-3][Formula 2-3]
Figure PCTKR2020010782-appb-I000033
Figure PCTKR2020010782-appb-I000033
[화학식 2-4][Formula 2-4]
Figure PCTKR2020010782-appb-I000034
Figure PCTKR2020010782-appb-I000034
상기 화학식 2-1 내지 2-4에 있어서, L, Ar3, Ar4 및 X1 내지 X3의 정의는 상기 화학식 2에서의 정의와 같다.In Formulas 2-1 to 2-4, the definitions of L, Ar3, Ar4, and X1 to X3 are the same as those in Formula 2.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2로 표시되는 화합물은 하기 구조식 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is represented by any one of the following structural formulas.
Figure PCTKR2020010782-appb-I000035
Figure PCTKR2020010782-appb-I000035
Figure PCTKR2020010782-appb-I000036
Figure PCTKR2020010782-appb-I000036
Figure PCTKR2020010782-appb-I000037
Figure PCTKR2020010782-appb-I000037
Figure PCTKR2020010782-appb-I000038
Figure PCTKR2020010782-appb-I000038
Figure PCTKR2020010782-appb-I000039
Figure PCTKR2020010782-appb-I000039
Figure PCTKR2020010782-appb-I000040
Figure PCTKR2020010782-appb-I000040
Figure PCTKR2020010782-appb-I000041
Figure PCTKR2020010782-appb-I000041
Figure PCTKR2020010782-appb-I000042
Figure PCTKR2020010782-appb-I000042
Figure PCTKR2020010782-appb-I000043
Figure PCTKR2020010782-appb-I000043
Figure PCTKR2020010782-appb-I000044
Figure PCTKR2020010782-appb-I000044
Figure PCTKR2020010782-appb-I000045
Figure PCTKR2020010782-appb-I000045
Figure PCTKR2020010782-appb-I000046
Figure PCTKR2020010782-appb-I000046
Figure PCTKR2020010782-appb-I000047
Figure PCTKR2020010782-appb-I000047
Figure PCTKR2020010782-appb-I000048
Figure PCTKR2020010782-appb-I000048
Figure PCTKR2020010782-appb-I000049
Figure PCTKR2020010782-appb-I000049
Figure PCTKR2020010782-appb-I000050
Figure PCTKR2020010782-appb-I000050
Figure PCTKR2020010782-appb-I000051
Figure PCTKR2020010782-appb-I000051
Figure PCTKR2020010782-appb-I000052
Figure PCTKR2020010782-appb-I000052
본 발명에서는 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 invention, 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 adjusted by introducing various substituents to the core structure of the above structure.
본 발명의 유기 발광 소자는 전술한 화학식 1의 화합물을 이용하여 제1 전극과 발광층 사이에 제1 유기물층을 형성하고, 화학식 2의 화합물을 이용하여 제2 전극과 발광층 사이에 제2 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.In the organic light emitting device of the present invention, a first organic material layer is formed between the first electrode and the emission layer using the compound of Formula 1, and a second organic material layer is formed between the second electrode and the emission layer using the compound of Formula 2. Except for this, it can be manufactured by a conventional method and material for manufacturing an organic light emitting device.
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 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, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공수송층, 정공주입층, 전자차단층 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 전자수송 및 주입층 중 1층 이상을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It can have a structure to 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 발명의 유기 발광 소자는 발광층을 포함하고, 제1 전극과 발광층 사이에 구비된 제1 유기물층은 화학식 1로 표시되는 화합물을, 제2 전극과 발광층 사이에 구비된 제2 유기물층은 화학식 2로 표시되는 화합물을 포함한다. The organic light-emitting device of the present invention includes a light-emitting layer, the first organic material layer provided between the first electrode and the light-emitting layer is represented by the compound represented by Formula 1, and the second organic material layer provided between the second electrode and the light-emitting layer is represented by formula 2. It includes a compound that becomes.
일 예에 따르면, 상기 화학식 1의 화합물을 포함하는 유기물층의 두께는 30Å 내지 300Å이고, 바람직하게는 50Å 내지 200Å이다.According to an example, the thickness of the organic material layer including the compound of Formula 1 is 30 Å to 300 Å, preferably 50 Å to 200 Å.
일 예에 따르면, 상기 화학식 2의 화합물을 포함하는 유기물층의 두께는 30Å 내지 200Å이고, 바람직하게는 50Å 내지 100Å이다.According to an example, the thickness of the organic material layer including the compound of Formula 2 is 30 Å to 200 Å, preferably 50 Å to 100 Å.
일 예에 따르면, 본 발명의 유기 발광 소자의 제1 전극과 발광층 사이에 구비되는 제1 유기물층은 정공주입층, 정공수송층 또는 정공주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층 또는 정공주입 및 수송층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an example, the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection And the transport layer includes the compound represented by Chemical Formula 1.
일 예에 따르면, 본 발명의 유기 발광 소자의 제1 전극과 발광층 사이에 구비되는 제1 유기물층은 정공주입층, 정공수송층 또는 정공주입 및 수송층일 수 있고, 상기 정공주입층, 정공수송층 또는 정공주입 및 수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to an example, the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection layer. And the transport layer may include a compound represented by Chemical Formula 1.
일 예에 따르면, 본 발명의 유기 발광 소자의 제1 전극과 발광층 사이에 구비되는 제1 유기물층은 전자차단층을 포함하고, 상기 전자차단층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an example, the first organic material layer provided between the first electrode and the emission layer of the organic light emitting device of the present invention includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.
일 예에 따르면, 본 발명의 유기 발광 소자의 제1 전극과 발광층 사이에 구비되는 제1 유기물층은 전자차단층으로, 상기 전자차단층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to an example, the first organic material layer provided between the first electrode and the emission layer of the organic light emitting device of the present invention may be an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 above.
일 예에 따르면, 본 발명의 유기 발광 소자의 제2 전극과 발광층 사이에 구비되는 제2 유기물층은 전자주입층, 전자수송층 또는 전자주입 및 수송층을 포함하고, 상기 전자주입층, 전자수송층 또는 전자주입 및 수송층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an example, the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer or the electron injection And the transport layer includes the compound represented by Chemical Formula 1.
일 예에 따르면, 본 발명의 유기 발광 소자의 제2 전극과 발광층 사이에 구비되는 제2 유기물층은 전자주입층, 전자수송층 또는 전자주입 및 수송층일 수 있고, 상기 전자주입층, 전자수송층 또는 전자주입 및 수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to an example, the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention may be an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection layer. And the transport layer may include a compound represented by Chemical Formula 1.
일 예에 따르면, 본 발명의 유기 발광 소자의 제2 전극과 발광층 사이에 구비되는 제2 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화학식 2로 표시되는 화합물을 포함한다.According to an example, the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 2.
일 예에 따르면, 본 발명의 유기 발광 소자의 제2 전극과 발광층 사이에 구비되는 제2 유기물층은 정공차단층으로, 상기 정공차단층은 상기 화학식 2로 표시되는 화합물을 포함할 수 있다.According to an example, the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention may be a hole blocking layer, and the hole blocking layer may include the compound represented by Formula 2.
또 하나의 실시상태에 있어서, 상기 제1 유기물층은 화학식 1로 표시되는 화합물 외에 다른 유기화합물, 금속 또는 금속화합물을 더 포함할 수 있다.In another exemplary embodiment, the first organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1.
또 하나의 실시상태에 있어서, 상기 제2 유기물층은 화학식 2로 표시되는 화합물 외에 다른 유기화합물, 금속 또는 금속화합물을 더 포함할 수 있다.In another exemplary embodiment, the second organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 2.
본 발명의 유기 발광 소자는 정공수송층, 정공주입층, 전자차단층, 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 정공수송 및 주입층 중 1 층 이상의 유기물층을 더 포함할 수 있다.The organic light emitting device of the present invention further comprises at least one organic material layer among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. I can.
일 예에 따르면, 상기 제1 유기물층은 발광층과 접해 있다. 여기서 접한다는 의미는 발광층과 제1 유기물층 사이에 다른 유기물층이 존재하지 않는 것이다.According to an example, the first organic material layer is in contact with the emission layer. Here, the meaning of contact means that no other organic material layer exists between the light emitting layer and the first organic material layer.
일 예에 따르면, 상기 제2 유기물층은 발광층과 접해 있다. 여기서 접한다는 의미는 발광층과 제2 유기물층 사이에 다른 유기물층이 존재하지 않는 것이다.According to an example, the second organic material layer is in contact with the emission layer. Here, the meaning of contact means that no other organic material layer exists between the light emitting layer and the second organic material layer.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자차단층을 포함할 수 있으며, 상기 전자차단층은 당 기술분야에 알려져 있는 재료가 사용될 수 있다.In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and a material known in the art may be used for the electron blocking layer.
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.
상기 유기 발광 소자는 예컨대 하기와 같은 적층 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
(1) 양극/정공수송층/발광층/음극(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode
(2) 양극/정공주입층/정공수송층/발광층/음극(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode
(3) 양극/정공주입층/정공버퍼층/정공수송층/발광층/음극(3) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Anode
(4) 양극/정공수송층/발광층/전자수송층/음극(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode
(5) 양극/정공수송층/발광층/전자수송층/전자주입층/음극(5) Anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/음극(6) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode
(7) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(8) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/음극(8) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Electron transport layer/Anode
(9) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /음극(9) Anode/Hole injection layer/Hole buffer layer/Hole transport layer/Light emitting layer/Electron transport layer/Electron injection layer/Anode
(10) 양극/ 정공수송층/전자차단층/발광층/전자수송층/음극(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(11) 양극/ 정공수송층/전자차단층/발광층/전자수송층/전자주입층/음극(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) 양극/정공주입층/정공수송층/전자차단층/발광층/전자수송층/음극(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(13) 양극/정공주입층/정공수송층/전자차단층/발광층/전자수송층/전자주입 층/음극(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) 양극/정공수송층/발광층/정공차단층/전자수송층/음극(14) Anode/Hole Transport Layer/Light-Emitting Layer/Hole Blocking Layer/Electron Transport Layer/Anode
(15) 양극/정공수송층/발광층/정공차단층/전자수송층/전자주입층/음극(15) Anode/Hole transport layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode
(16) 양극/정공주입층/정공수송층/발광층/정공차단층/전자수송층/음극(16) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode
(17) 양극/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입 층/음극(17) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode
(18) 양극/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입 층/음극/캡슐(18) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule
(19) 양극/정공주입층/제1 정공수송층/제2 정공수송층/발광층/정공차단층/전자수송층/전자주입 층/음극/캡슐(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule
(20) 양극/정공주입층/정공수송층/전자차단층/발광층/정공차단층/전자수송 및 주입층/음극(20) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport and injection layer/cathode
본 발명의 유기 발광 소자의 구조는 도 1 및 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
도 1에는 기판(1), 양극(2), 전자차단층(5), 발광층(6), 정공차단층(7) 및 음극(9)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물은 상기 전자차단층(5), 발광층(6) 또는 정공차단층(7)에 포함될 수 있다.FIG. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9 are sequentially stacked. . In such a structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the electron blocking layer 5, the light emitting layer 6, or the hole blocking layer 7.
도 2에는 기판 (1), 양극(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송 및 주입층(8) 및 음극(9)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물은 상기 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7) 또는 전자수송 및 주입층(8)에 포함될 수 있다.2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport and injection layer. The structure of an organic light-emitting device in which (8) and a cathode (9) are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 and the compound represented by Formula 2 are the hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), and hole blocking. It may be included in the layer 7 or the electron transport and injection layer 8.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 발광층, 전자차단층, 전자수송층 및 전자주입층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. Deposited to form an anode, formed by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. Can be. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공수송층, 정공주입층, 전자차단층, 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 정공수송 및 주입층 중 1 층 이상을 더 포함할 수 있다.The organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
상기 유기물층은 정공주입층, 정공수송층, 전자주입 및 전자수송을 동시에 하는층, 전자차단층, 발광층 및 전자수송층, 전자주입층, 전자수송 및 주입층 등을 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 may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc. It may not have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
상기 양극은 정공을 주입하는 전극으로, 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 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; 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 a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the anode material. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극은 전자를 주입하는 전극으로, 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 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 usually a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 정공주입층은 양극으로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이며, 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 정공주입층의 두께는 1 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 상승되는것을 방지할 수 있는 이점이 있다.The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and the hole injection material is a material capable of receiving holes from the anode at a low voltage, and is a high occupied HOMO (highest occupied material) of the hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it.
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer may serve to facilitate transport of holes. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
정공주입층과 정공수송층 사이에 추가로 정공버퍼층이 구비될 있으며, 당 기술분야에 알려져 있는 정공주입 또는 수송재료를 포함할 수 있다. A hole buffer layer may be additionally 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 전자차단층이 구비될 수 있다. 상기 전자차단층에는 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 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 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 emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding 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. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 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, 이에 한정되지 않는다.Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are 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, 이에만 한정된 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.When the emission layer emits red light, the emission dopants include 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), but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (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 is a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
전자수송층과 발광층 사이에 정공차단층이 구비될 수 있으며, 상기 정공차단층에는 전술한 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다.A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the above-described compound or a material known in the art may be used for the hole blocking layer.
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 할 수 있다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1 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 transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage that can be.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 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 injection of electrons. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for 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 compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are 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 lithium 8-hydroxyquinolinato, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
본 명세서의 일 실시상태에 있어서, 유기 발광 소자는 상기 정공차단층 외에 1층 이상의 정공차단층을 추가로 포함할 수 있다.In the exemplary embodiment of the present specification, the organic light emitting device may further include at least one hole blocking layer in addition to the hole blocking layer.
상기 정공차단층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are 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 bottom emission type, or a double-sided emission type depending on the material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 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, in order to explain the present specification in detail, it will be described in detail with reference to examples. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present application is not construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely describe the present specification to those of ordinary skill in the art.
제조예 A 내지 C: 중간체 A 내지 C의 제조Preparation Examples A to C: Preparation of Intermediates A to C
Figure PCTKR2020010782-appb-I000053
Figure PCTKR2020010782-appb-I000053
Figure PCTKR2020010782-appb-I000054
Figure PCTKR2020010782-appb-I000054
상기와 같은 과정을 통하여 중간체 A 내지 C를 제조하였다.Intermediates A to C were prepared through the same process as above.
제조예 1: 화합물 1-1의 제조Preparation Example 1: Preparation of compound 1-1
Figure PCTKR2020010782-appb-I000055
Figure PCTKR2020010782-appb-I000055
질소 분위기에서 500 ml 둥근 바닥 플라스크에 화합물 N,N-비스(4-브로모페닐)-[1,1'-비페닐]-4-아민(6.74 g, 12.23 mmol), (2-(9H-카바졸-9-일)페닐)보론산 ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (4.04g, 14.07 mmol)을 테트라하이드로퓨란 240 ml에 완전히 녹인 후 2M 탄산칼륨수용액(120 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.42g, 0.37 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 240 ml로 재결정하여 화합물 1-1(6.11g, 70%)를 제조하였다.Compound N,N-bis(4-bromophenyl)-[1,1'-biphenyl]-4-amine (6.74 g, 12.23 mmol), (2-(9H-) in a 500 ml round bottom flask in a nitrogen atmosphere Carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (4.04g, 14.07 mmol) was completely dissolved in 240 ml of tetrahydrofuran and then 2M potassium carbonate aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine)palladium (0.42g, 0.37 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to prepare compound 1-1 (6.11 g, 70%).
MS[M+H]+= 715MS[M+H] + = 715
제조예 2: 화합물 1-2의 제조Preparation Example 2: Preparation of compound 1-2
Figure PCTKR2020010782-appb-I000056
Figure PCTKR2020010782-appb-I000056
질소 분위기에서 500 ml 둥근 바닥 플라스크에 화합물 4'-브로모-N-(4-브로모페닐)-N-페닐-[1,1'-비페닐]-4-아민(8.45 g, 22.06 mmol), (2-(9H-카바졸-9-일)페닐)보론산 ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (5.06 g, 17.64 mmol)을 테트라하이드로퓨란 240 ml에 완전히 녹인 후 2M 탄산칼륨수용액(120 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.53 g, 0.46 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 250 ml로 재결정하여 화합물 1-2 (7.16 g, 63%)를 제조하였다.Compound 4'-bromo-N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (8.45 g, 22.06 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere , (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (5.06 g, 17.64 mmol) in 240 ml of tetrahydrofuran After completely dissolved, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis-(triphenylphosphine) palladium (0.53 g, 0.46 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare compound 1-2 (7.16 g, 63%).
MS[M+H]+= 739MS[M+H] + = 739
제조예 3: 화합물 1-3의 제조Preparation Example 3: Preparation of compound 1-3
Figure PCTKR2020010782-appb-I000057
Figure PCTKR2020010782-appb-I000057
질소 분위기에서 500 ml 둥근 바닥 플라스크에 화합물 N-(3-브로모페닐)-N-(4-브로모페닐)-[1,1'-비페닐]-4-아민(9.12g, 20.31 mmol), (2-(9H-카바졸-9-일)페닐)보론산 ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (6.70g, 23.36 mmol)을 테트라하이드로퓨란 240 ml에 완전히 녹인 후 2M 탄산칼륨수용액(120 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.70g, 0.61 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 210 ml로 재결정하여 화합물 1-3 (8.44 g, 63%)를 제조하였다.Compound N-(3-bromophenyl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine (9.12 g, 20.31 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere , (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (6.70g, 23.36 mmol) in 240 ml of tetrahydrofuran After completely dissolved, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis-(triphenylphosphine) palladium (0.70g, 0.61 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to prepare compound 1-3 (8.44 g, 63%).
MS[M+H]+= 663MS[M+H] + = 663
제조예 4: 화합물 2-1의 제조Preparation Example 4: Preparation of compound 2-1
Figure PCTKR2020010782-appb-I000058
Figure PCTKR2020010782-appb-I000058
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 A (10.87g, 23.74mmol), 2-([1,1':4',1''-터페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 (2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) (8.65, 20.64mmol)을 테트라하이드로퓨란 240ml에 완전히 녹인 후 2M 탄산칼륨수용액(120ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.72g, 0.62mmol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 310ml로 재결정하여 화합물 2-1 (13.45g, 79%)를 제조하였다.Compound A (10.87g, 23.74mmol), 2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl in a 500 ml round bottom flask in a nitrogen atmosphere -1,3,5-triazine (2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) (8.65, 20.64mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.72g, 0.62mmol) was added, and then heated for 5 hours. Stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 ml of tetrahydrofuran to prepare compound 2-1 (13.45g, 79%).
MS[M+H]+= 716MS[M+H] + = 716
제조예 5: 화합물 2-2의 제조Preparation Example 5: Preparation of compound 2-2
Figure PCTKR2020010782-appb-I000059
Figure PCTKR2020010782-appb-I000059
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 B (12.25g, 36.75mmol), 2-클로로-4-(4-(나프탈렌-1-일)페닐)-6-페닐-1,3,5-트리아진 (2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine) (9.14, 23.26mmol)을 테트라하이드로퓨란 280ml에 완전히 녹인 후 2M 탄산칼륨수용액(140ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.81g, 0.70mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세토니트릴 290ml로 재결정하여 화합물 2-2 (8.95g, 60%)를 제조하였다.Compound B (12.25g, 36.75mmol), 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine ( 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine) (9.14, 23.26mmol) was completely dissolved in 280 ml of tetrahydrofuran and then 2M potassium carbonate aqueous solution (140ml) was added, tetrakis-(triphenylphosphine)palladium (0.81g, 0.70mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 ml of acetonitrile to prepare compound 2-2 (8.95g, 60%).
MS[M+H]+= 690MS[M+H] + = 690
제조예 6: 화합물 2-3의 제조Preparation Example 6: Preparation of compound 2-3
Figure PCTKR2020010782-appb-I000060
Figure PCTKR2020010782-appb-I000060
질소 분위기에서 500ml 둥근 바닥 플라스크에 화합물 C (11.41g, 24.92mmol), (4-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)보론산 ((4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid) (7.65g, 21.67mmol)을 테트라하이드로퓨란 260ml에 완전히 녹인 후 2M 탄산칼륨수용액(130ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.75g, 0.65mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 230ml로 재결정하여 화합물 2-3 (7.17g, 52%)를 제조하였다.Compound C (11.41g, 24.92mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid ((4- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid) (7.65g, 21.67mmol) was completely dissolved in 260ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (130ml) was added. , Tetrakis-(triphenylphosphine)palladium (0.75g, 0.65mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of tetrahydrofuran to prepare compound 2-3 (7.17 g, 52%).
MS[M+H]+= 640MS[M+H] + = 640
제조예 7: 화합물 2-4의 제조Preparation Example 7: Preparation of compound 2-4
Figure PCTKR2020010782-appb-I000061
Figure PCTKR2020010782-appb-I000061
상기 제조예 4에서, 2-([1,1':4',1''-터페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 (2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) 대신 2-([1,1'-바이페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진 (2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine)를 사용한 것을 제외하고는, 동일한 방법으로 합성하였다.In Preparation Example 4, 2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2- 2-([1,1'-biphenyl instead of ([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) ]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1 ,3,5-triazine) was synthesized in the same manner, except that it was used.
MS[M+H]+= 640MS[M+H] + = 640
비교예 1Comparative Example 1
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 a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then 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 ITO 투명 전극 위에 하기 화합물 [HI-1] 및 하기 화합물 [HI-2]를 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다.On the thus prepared ITO transparent electrode, the following compound [HI-1] and the following compound [HI-2] were thermally vacuum deposited to a thickness of 100 Å in a ratio of 98:2 (molar ratio) to form a hole injection layer.
상기 정공주입층 위에 정공을 수송하는 물질인 하기 화합물 [HT-1] (1150Å)를 진공 증착하여 정공수송층을 형성하였다.The following compound [HT-1] (1150Å), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.
이어서, 상기 정공수송층 위에 막 두께 50Å으로 하기 화합물 [EB-1] (150Å)를 진공 증착하여 전자차단층을 형성하였다.Subsequently, the following compound [EB-1] (150Å) with a film thickness of 50Å was vacuum deposited on the hole transport layer to form an electron blocking layer.
이어서, 상기 전자차단층 위에 막 두께 200Å으로 아래와 같은 [BH-1]와 [BD-1]를 40:1의 중량비로 진공증착하여 발광층을 형성하였다.Subsequently, on the electron blocking layer, [BH-1] and [BD-1] were vacuum-deposited at a weight ratio of 40:1 with a film thickness of 200 Å to form a light emitting layer.
상기 발광층 위에 막 두께 50Å으로 하기 화합물 [HB-1]를 진공 증착하여 정공차단층을 형성하였다.A hole blocking layer was formed by vacuum depositing the following compound [HB-1] with a film thickness of 50 Å on the emission layer.
이어서, 상기 정공차단층 위에 화합물 [ET-1]과 하기 화합물 LiQ(Lithium Quinolate)를 1:1의 중량비로 진공증착하여 300Å의 두께로 전자주입 및 수송층을 형성하였다.Subsequently, the compound [ET-1] and the following compound LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300Å.
상기 전자주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 2,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다.Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 2,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 ~ 5×10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2×10 − Maintaining 7 ~ 5 × 10 -6 torr, an organic light emitting device was manufactured.
Figure PCTKR2020010782-appb-I000062
Figure PCTKR2020010782-appb-I000062
실험예 1-1 내지 실험예 1-12Experimental Example 1-1 to Experimental Example 1-12
비교예 1의 화합물 [EB-1] 및 [HB-1] 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.
Figure PCTKR2020010782-appb-I000063
Figure PCTKR2020010782-appb-I000063
비교예 2 내지 비교예 17Comparative Examples 2 to 17
비교예 1의 화합물 [EB-1] 및 [HB-1] 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.
상기 실험예 및 비교예에서 제조한 유기 발광 소자에 10 mA/cm2의 전류를 인가하였을 때, 구동 전압, 발광 효율 및 색 좌표를 측정하였고, 10 mA/cm2의 전류밀도에서 초기 휘도 대비 95%가 되는 시간(T95)을 측정하였다. 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When a current of 10 mA/cm 2 was applied to the organic light emitting device prepared in the above Experimental Examples and Comparative Examples, the driving voltage, luminous efficiency and color coordinates were measured, and 95 compared to the initial luminance at a current density of 10 mA/cm 2 . The time to become% (T95) was measured. The results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물(전자차단층)Compound (electron blocking layer) 화합물(정공차단층)Compound (hole 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 coordinate (x,y) T95(hr)T95(hr)
비교예 1Comparative Example 1 EB-1EB-1 HB-1HB-1 5.095.09 5.905.90 (0.144, 0.045)(0.144, 0.045) 235235
실험예 1-1Experimental Example 1-1 1-11-1 2-12-1 3.553.55 6.726.72 (0.144, 0.046)(0.144, 0.046) 350350
실험예 1-2Experimental Example 1-2 1-11-1 2-22-2 3.563.56 6.636.63 (0.145, 0.047)(0.145, 0.047) 345345
실험예 1-3Experimental Example 1-3 1-11-1 2-32-3 3.573.57 6.746.74 (0.144, 0.046)(0.144, 0.046) 355355
실험예 1-4Experimental Example 1-4 1-11-1 2-42-4 3.533.53 6.776.77 (0.145, 0.046)(0.145, 0.046) 370370
실험예 1-5Experimental Example 1-5 1-21-2 2-12-1 3.613.61 6.726.72 (0.145, 0.047)(0.145, 0.047) 335335
실험예 1-6Experimental Example 1-6 1-21-2 2-22-2 3.623.62 6.656.65 (0.144, 0.046)(0.144, 0.046) 340340
실험예 1-7Experimental Example 1-7 1-21-2 2-32-3 3.633.63 6.676.67 (0.146, 0.045)(0.146, 0.045) 335335
실험예 1-8Experimental Example 1-8 1-21-2 2-42-4 3.593.59 6.756.75 (0.146, 0.046)(0.146, 0.046) 355355
실험예 1-9Experimental Example 1-9 1-31-3 2-12-1 3.743.74 6.786.78 (0.145, 0.045)(0.145, 0.045) 330330
실험예 1-10Experimental Example 1-10 1-31-3 2-22-2 3.783.78 6.716.71 (0.144, 0.046)(0.144, 0.046) 345345
실험예 1-11Experimental Example 1-11 1-31-3 2-32-3 3.793.79 6.666.66 (0.145, 0.047)(0.145, 0.047) 330330
실험예 1-12Experimental Example 1-12 1-21-2 2-42-4 3.713.71 6.806.80 (0.145, 0.046)(0.145, 0.046) 350350
비교예 2Comparative Example 2 1-11-1 HB-1HB-1 4.354.35 6.386.38 (0.144, 0.045)(0.144, 0.045) 260260
비교예 3Comparative Example 3 1-21-2 HB-1HB-1 4.314.31 6.376.37 (0.145, 0.046)(0.145, 0.046) 275275
비교예 4Comparative Example 4 1-31-3 HB-1HB-1 4.334.33 6.356.35 (0.145, 0.045)(0.145, 0.045) 240240
비교예 5Comparative Example 5 1-11-1 HB-2HB-2 4.574.57 6.216.21 (0.144, 0.046)(0.144, 0.046) 260260
비교예 6Comparative Example 6 EB-1EB-1 2-12-1 4.314.31 6.006.00 (0.144, 0.047)(0.144, 0.047) 320320
비교예 7Comparative Example 7 EB-1EB-1 2-22-2 4.324.32 6.066.06 (0.146, 0.046)(0.146, 0.046) 315315
비교예 8Comparative Example 8 EB-1EB-1 2-32-3 4.354.35 6.046.04 (0.145, 0.045)(0.145, 0.045) 325325
비교예 9Comparative Example 9 EB-1EB-1 2-42-4 4.294.29 6.086.08 (0.145, 0.046)(0.145, 0.046) 335335
비교예 10Comparative Example 10 EB-3EB-3 2-12-1 4.134.13 6.116.11 (0.145, 0.047)(0.145, 0.047) 290290
비교예 11Comparative Example 11 EB-3EB-3 2-22-2 4.144.14 6.176.17 (0.147, 0.046)(0.147, 0.046) 285285
비교예 12Comparative Example 12 EB-3EB-3 2-32-3 4.174.17 6.156.15 (0.146, 0.045)(0.146, 0.045) 295295
비교예 13Comparative Example 13 EB-4EB-4 2-12-1 4.124.12 6.136.13 (0.145, 0.046)(0.145, 0.046) 270270
비교예 14Comparative Example 14 EB-4EB-4 2-22-2 4.154.15 6.166.16 (0.147, 0.046)(0.147, 0.046) 265265
비교예 15Comparative Example 15 EB-4EB-4 2-32-3 4.184.18 6.146.14 (0.146, 0.045)(0.146, 0.045) 275275
비교예 16Comparative Example 16 EB-2EB-2 HB-1HB-1 4.764.76 6.076.07 (0.145, 0.045)(0.145, 0.045) 175175
비교예 17Comparative Example 17 EB-1EB-1 HB-2HB-2 4.784.78 5.435.43 (0.146, 0.045)(0.146, 0.045) 150150
상기 표 1에 나타난 바와 같이, 실험예 1-1 내지 1-12는, 본 발명 화학식 1의 화합물과 화학식 2의 화합물을 각각 전자차단층 및 정공차단층에 사용한 것으로, 화학식 1 및 화학식 2로 표시되는 화합물을 함께 적용한 소자의 특성을 나타낸다.As shown in Table 1, in Experimental Examples 1-1 to 1-12, the compound of Formula 1 and the compound of Formula 2 were used in the electron blocking layer and the hole blocking layer, respectively, and represented by Formulas 1 and 2 It shows the characteristics of the device in which the compound is applied together.
비교예 2 내지 15은 비교예 1에서 화학식 1의 화합물을 EB-1 대신 사용하거나, 또는 화학식 2의 화합물을 HB-1 대신 사용한 것으로, 화학식 1로 표시되는 화합물만을 사용하거나, 화학식 2로 표시되는 화합물만을 사용한 소자의 특성을 나타낸다.In Comparative Examples 2 to 15, the compound of Formula 1 was used instead of EB-1 in Comparative Example 1, or the compound of Formula 2 was used instead of HB-1, and only the compound represented by Formula 1 was used, or the compound represented by Formula 2 The characteristics of the device using only the compound are shown.
비교예 1 내지 17 대비 실험예 1-1 내지 1-12의 유기 발광 소자는 기본적으로 저전압, 고효율 및 장수명의 특성을 나타내며, 특히 화학식 1의 화합물들은 고효율의 특성을 가지고 있고, 화학식 2의 화합물들은 장수명의 특성을 가지고 있다.Compared to Comparative Examples 1 to 17, the organic light emitting devices of Experimental Examples 1-1 to 1-12 basically exhibit characteristics of low voltage, high efficiency, and long life. In particular, the compounds of Formula 1 have high efficiency, and the compounds of Formula 2 It has the characteristics of long life.
구체적으로, 실험예 1-1 내지 1-12의 소자는 비교예에 비하여, 발광 효율은 최대 약 25% 정도 높아지며, 수명은 최대 약 150% 정도 증가한 결과를 나타내었다.Specifically, the devices of Experimental Examples 1-1 to 1-12 showed a result that the luminous efficiency was increased by up to about 25% and the life was increased by up to about 150% compared to the comparative example.
이를 통하여, 본 발명의 화학식 1의 화합물을 전자차단층 재료로 사용하고 본 발명의 화학식 2의 화합물을 정공차단층으로 조합할 경우, 유기 발광 소자의 장수명 특성을 유지하면서 고효율 특성을 가지는 것이 가능하다는 것을 확인할 수 있다.Through this, when the compound of Formula 1 of the present invention is used as an electron blocking layer material and the compound of Formula 2 of the present invention is combined as a hole blocking layer, it is possible to have high efficiency characteristics while maintaining the long life characteristics of the organic light emitting device. Can be confirmed.
이상을 통해 본 발명의 바람직한 실시예(전자차단층 화합물과 정공차단층 화합물의 조합)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 of the present invention (a combination of an electron blocking layer compound and a hole blocking layer compound) has been described above, the present invention is not limited thereto, but various modifications within the scope of the claims and the detailed description of the invention It is possible to do so, and this also belongs to the scope of the invention.

Claims (13)

  1. 제1 전극;A first electrode;
    제2 전극;A second electrode;
    상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층;An emission layer provided between the first electrode and the second electrode;
    상기 제1 전극과 상기 발광층 사이에 구비된 제1 유기물층; 및A first organic material layer provided between the first electrode and the emission layer; And
    상기 제2 전극과 상기 발광층 사이에 구비된 제2 유기물층을 포함하는 유기 발광 소자로서,An organic light emitting device comprising a second organic material layer provided between the second electrode and the light emitting layer,
    상기 제1 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고,The first organic material layer includes a compound represented by Formula 1 below,
    상기 제2 유기물층은 하기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자:The second organic material layer is an organic light emitting device including a compound represented by the following formula (2):
    [화학식 1][Formula 1]
    Figure PCTKR2020010782-appb-I000064
    Figure PCTKR2020010782-appb-I000064
    상기 화학식 1에 있어서,In Formula 1,
    Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 알킬기 또는 아릴기로 치환 또는 비치환된 아릴기이고,Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
    R1은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
    n은 1 내지 8의 정수이고, n이 2 이상인 경우 2 이상의 R1은 서로 동일하거나 상이하고,n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
    [화학식 2][Formula 2]
    Figure PCTKR2020010782-appb-I000065
    Figure PCTKR2020010782-appb-I000065
    상기 화학식 2에 있어서,In Formula 2,
    L은 직접 결합; 치환 또는 비치환된 아릴렌기; 치환 또는 비치환된 알킬렌기; 치환 또는 비치환된 2가의 알콕시기; 치환 또는 비치환된 2가의 알케닐기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
    X1은 N; 또는 CR11이고, X2는 N; 또는 CR12이며, X3는 N; 또는 CR13이며,X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
    X1 내지 X3 중 적어도 하나는 N이고,At least one of X1 to X3 is N,
    R11 내지 R13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    Ar3 및 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  2. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시되는 것인 유기 발광 소자:Formula 1 is an organic light-emitting device represented by Formula 1-1 or 1-2:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2020010782-appb-I000066
    Figure PCTKR2020010782-appb-I000066
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2020010782-appb-I000067
    Figure PCTKR2020010782-appb-I000067
    상기 화학식 1-1 및 1-2에 있어서, Ar1, Ar2, R1 및 n의 정의는 상기 화학식 1에서의 정의와 같다.In Formulas 1-1 and 1-2, the definitions of Ar1, Ar2, R1 and n are the same as those in Formula 1.
  3. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 2는 하기 화학식 2-1 내지 2-4 중 어느 하나로 표시되는 것인 유기 발광 소자: Formula 2 is an organic light-emitting device represented by any one of the following Formulas 2-1 to 2-4:
    [화학식 2-1][Formula 2-1]
    Figure PCTKR2020010782-appb-I000068
    Figure PCTKR2020010782-appb-I000068
    [화학식 2-2][Formula 2-2]
    Figure PCTKR2020010782-appb-I000069
    Figure PCTKR2020010782-appb-I000069
    [화학식 2-3][Formula 2-3]
    Figure PCTKR2020010782-appb-I000070
    Figure PCTKR2020010782-appb-I000070
    [화학식 2-4][Formula 2-4]
    Figure PCTKR2020010782-appb-I000071
    Figure PCTKR2020010782-appb-I000071
    상기 화학식 2-1 내지 2-4에 있어서, L, Ar3, Ar4 및 X1 내지 X3의 정의는 상기 화학식 2에서의 정의와 같다.In Formulas 2-1 to 2-4, the definitions of L, Ar3, Ar4, and X1 to X3 are the same as those in Formula 2.
  4. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1은 하기 화학식 1-3 내지 1-6 중 어느 하나로 표시되는 것인 유기 발광 소자:Formula 1 is an organic light-emitting device represented by any one of the following Formulas 1-3 to 1-6:
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2020010782-appb-I000072
    Figure PCTKR2020010782-appb-I000072
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2020010782-appb-I000073
    Figure PCTKR2020010782-appb-I000073
    [화학식 1-5][Formula 1-5]
    Figure PCTKR2020010782-appb-I000074
    Figure PCTKR2020010782-appb-I000074
    [화학식 1-6][Formula 1-6]
    Figure PCTKR2020010782-appb-I000075
    Figure PCTKR2020010782-appb-I000075
    상기 화학식 1-3 내지 1-6에 있어서, Ar1 및 Ar2의 정의는 상기 화학식 1에서의 정의와 같고,In Formulas 1-3 to 1-6, the definitions of Ar1 and Ar2 are the same as those in Formula 1,
    G1 및 G2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
    g1은 1 내지 10의 정수이고,g1 is an integer from 1 to 10,
    g2는 1 내지 8의 정수이고,g2 is an integer from 1 to 8,
    g1이 2 이상인 경우, 2 이상의 G1은 서로 동일하거나 상이하고, g2가 2 이상인 경우, 2 이상의 G2는 서로 동일하거나 상이하다.When g1 is 2 or more, two or more G1s are the same as or different from each other, and when g2 is 2 or more, two or more G2s are the same or different from each other.
  5. 청구항 1에 있어서, The method according to claim 1,
    상기 Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 바이페닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 나프틸기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 페난트레닐기; 페닐기, 나프틸기 또는 페난트레닐기로 치환 또는 비치환된 터페닐기; 또는 메틸기로 치환 또는 비치환된 플루오레닐기인 것인 유기 발광 소자.Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or an organic light emitting device that is a fluorenyl group unsubstituted or substituted with a methyl group.
  6. 청구항 1에 있어서,The method according to claim 1,
    상기 L은 직접 결합; 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 바이페닐렌기인 것인 유기 발광 소자.L is a direct bond; A substituted or unsubstituted phenylene group; Or an organic light-emitting device that is a substituted or unsubstituted biphenylene group.
  7. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중 어느 하나로 표시되는 것인 유기 발광 소자:The organic light-emitting device of claim 1, wherein Formula 1 is represented by any one of the following compounds:
    Figure PCTKR2020010782-appb-I000076
    Figure PCTKR2020010782-appb-I000076
    Figure PCTKR2020010782-appb-I000077
    Figure PCTKR2020010782-appb-I000077
    Figure PCTKR2020010782-appb-I000078
    Figure PCTKR2020010782-appb-I000078
    Figure PCTKR2020010782-appb-I000079
    Figure PCTKR2020010782-appb-I000079
    Figure PCTKR2020010782-appb-I000080
    .
    Figure PCTKR2020010782-appb-I000080
    .
  8. 청구항 1에 있어서,The method according to claim 1,
    상기 화학식 2는 하기 화합물 중 어느 하나로 표시되는 것인 유기 발광 소자:Formula 2 is an organic light-emitting device represented by any one of the following compounds:
    Figure PCTKR2020010782-appb-I000081
    Figure PCTKR2020010782-appb-I000081
    Figure PCTKR2020010782-appb-I000082
    Figure PCTKR2020010782-appb-I000082
    Figure PCTKR2020010782-appb-I000083
    Figure PCTKR2020010782-appb-I000083
    Figure PCTKR2020010782-appb-I000084
    Figure PCTKR2020010782-appb-I000084
    Figure PCTKR2020010782-appb-I000085
    Figure PCTKR2020010782-appb-I000085
    Figure PCTKR2020010782-appb-I000086
    Figure PCTKR2020010782-appb-I000086
    Figure PCTKR2020010782-appb-I000087
    Figure PCTKR2020010782-appb-I000087
    Figure PCTKR2020010782-appb-I000088
    Figure PCTKR2020010782-appb-I000088
    Figure PCTKR2020010782-appb-I000089
    Figure PCTKR2020010782-appb-I000089
    Figure PCTKR2020010782-appb-I000090
    Figure PCTKR2020010782-appb-I000090
    Figure PCTKR2020010782-appb-I000091
    Figure PCTKR2020010782-appb-I000091
    Figure PCTKR2020010782-appb-I000092
    Figure PCTKR2020010782-appb-I000092
    Figure PCTKR2020010782-appb-I000093
    Figure PCTKR2020010782-appb-I000093
    Figure PCTKR2020010782-appb-I000094
    Figure PCTKR2020010782-appb-I000094
    Figure PCTKR2020010782-appb-I000095
    Figure PCTKR2020010782-appb-I000095
    Figure PCTKR2020010782-appb-I000096
    Figure PCTKR2020010782-appb-I000096
    Figure PCTKR2020010782-appb-I000097
    Figure PCTKR2020010782-appb-I000097
    Figure PCTKR2020010782-appb-I000098
    .
    Figure PCTKR2020010782-appb-I000098
    .
  9. 청구항 1에 있어서, 상기 제1 유기물층은 정공주입층, 정공수송층 또는 정공주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층 또는 정공주입 및 수송층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The method according to claim 1, wherein the first organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer comprises a compound represented by Formula 1 Organic light emitting device.
  10. 청구항 1에 있어서, 상기 제2 유기물층은 전자주입층, 전자수송층 또는 전자주입 및 수송층을 포함하고, 상기 전자주입층, 전자수송층 또는 전자주입 및 수송층은 상기 화학식 2로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The method according to claim 1, wherein the second organic material layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises a compound represented by Formula 2 Organic light emitting device.
  11. 청구항 1에 있어서, The method according to claim 1,
    상기 제1 유기물층은 전자차단층을 포함하고, 상기 전자차단층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 것인 유기 발광 소자.The first organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.
  12. 청구항 1에 있어서,The method according to claim 1,
    상기 제2 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화학식 2로 표시되는 화합물을 포함하는 것인 것인 유기 발광 소자.The second organic material layer includes a hole blocking layer, and the hole blocking layer is an organic light-emitting device including the compound represented by Formula 2.
  13. 청구항 1에 있어서,The method according to claim 1,
    상기 유기 발광 소자는 정공수송층, 정공주입층, 전자차단층, 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 정공수송 및 주입층 중 1 층 이상의 유기물층을 더 포함하는 것인 유기 발광 소자.The organic light emitting device further comprises at least one organic material layer among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. Organic light emitting device.
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Publication number Priority date Publication date Assignee Title
CN113461672A (en) * 2021-05-13 2021-10-01 上海和辉光电股份有限公司 Polycyclic aromatic hydrocarbon compound and application thereof
WO2024122799A1 (en) * 2022-12-09 2024-06-13 주식회사 엘지화학 Compound and organic light-emitting element comprising same

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CN113924666A (en) 2022-01-11

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