KR20240078941A - Compound and organic light emitting device comprising same - Google Patents

Abstract

This specification provides a compound represented by Formula 1 and an organic light-emitting device containing the same.

Description

Compound and organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

This specification relates to compounds and organic light-emitting devices containing the same.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.

The development of new materials for organic light-emitting devices as described above continues to be required.

Korean Patent Publication No. 10-2012-119942

In this specification, compounds and organic light-emitting devices containing the same are provided.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted aryl group,

A is a substituted or unsubstituted 2 or more ring condensed aryl group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group,

R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n1 is an integer from 0 to 7, n2 is an integer from 0 to 8, and n3 is an integer from 0 to 4. When n1 to n3 are each 2 or more, two or more substituents in parentheses are the same or different from each other.

In addition, an exemplary embodiment of the present specification includes an anode; cathode; and an organic light emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1.

The compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device. A compound according to at least one embodiment of the present specification can improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.

Figure 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 9 are sequentially stacked.
Figure 2 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( 8) and the cathode 9 are sequentially stacked.

Hereinafter, this specification will be described in more detail.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In this specification, " "refers to a chemical formula or a position bonded to a compound.

Examples of substituents in this specification are described below, but are not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group (-CN); nitro group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; alkenyl group; silyl group; boron group; Amine group; Aryl group; Alternatively, it means that it is substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; amino group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; Alkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

Examples of the above substituents are described below, but are not limited thereto.

In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups 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, etc., but are not limited to these.

In the present specification, the description of the alkyl group described above may be applied, except that the arylalkyl group is substituted with an aryl group.

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n. -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 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, etc., but are not limited to these.

In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the carbon number of the alkynyl group is 2 to 10.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of substituted amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, and diphenylamine. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Ditolylamine group, phenyltolylamine group, diphenylamine group, etc., but are not limited to these.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrene group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is limited thereto. That is not the case.

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. At this time, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

When the fluorenyl group is substituted, , , 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 to this.

In the present specification, the above-described description of the aryl group may be applied to the aryl group among the aryloxy group, arylamine group, and arylsilyl group.

In the present specification, the above-described description of the alkyl group may be applied to the alkyl group among the alkylthioxy group and the alkylsulfoxy group.

In the present specification, the above-mentioned description of the aryl group may be applied to the aryl group among the arylthioxy group and the arylsulfoxy group.

In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. According to one embodiment, the carbon number of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, and dibenzothiophene group. , carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, etc., but is not limited to these.

In the present specification, the description regarding the heterocyclic group described above can be applied, except that the heteroaryl group is aromatic.

In the present specification, the description of the aryl group may be applied, except that the arylene group is divalent.

In the present specification, the description of the heteroaryl group above can be applied, except that the heteroarylene group is divalent.

In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” is a hydrocarbon ring; Or refers to a heterocycle.

The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group.

In the present specification, forming a ring by combining with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by combining with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensation ring thereof. The hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring consisting only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene. It is not limited to this.

In this specification, an 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, etc., but are not limited thereto. In the present specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.

As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, and thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzoyl Examples include, but are not limited to, carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

As used herein, “X% deuterated”, “Deuteration degree X%”, or “Deuterium substitution rate X%” means that

For example, when the structure in question is dibenzofuran, the dibenzofuran is “25% deuterated,” the “deuteration degree of 25%” of the dibenzofuran, or the “deuterium substitution rate of 25%” of the dibenzofuran is as described above. This may mean that two of the eight hydrogens at the replaceable positions of dibenzofuran are substituted or unsubstituted with deuterium.

In the present specification, hydrogen that can be replaced by deuterium in the structure may be substituted with deuterium by more than 0% and less than 100%, more than 0.1% and less than 99.99%, or up to 100%. For example, if the structure in question is dibenzofuran, the dibenzofuran is “25% deuterated,” the “deuteration degree of 25%” of the dibenzofuran, or the “deuterium substitution rate of 25%” of the dibenzofuran is defined as the above. This may mean that 8 of the 8 hydrogens at the replaceable positions of dibenzofuran are substituted with 25% deuterium, or 4 of the 8 hydrogens at the replaceable positions are replaced with 50% deuterium.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

Therefore, when the compound represented by the above-mentioned formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and/or long lifespan characteristics can be obtained.

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted aryl group,

A is a substituted or unsubstituted 2 or more ring condensed aryl group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group,

R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n1 is an integer from 0 to 7, n2 is an integer from 0 to 8, and n3 is an integer from 0 to 4. When n1 to n3 are each 2 or more, two or more substituents in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

The definitions of L1, L2, Ar1, A, R1 to R3 and n1 to n3 are the same as in Formula 1 above.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted biphenylylene group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, A is a substituted or unsubstituted 2 or more rings condensed aryl group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to another exemplary embodiment, A is a substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted fluoranthene group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to another exemplary embodiment, R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, n1 is an integer from 0 to 7, and when n1 is 2 or more, 2 or more R1 are the same or different from each other.

According to an exemplary embodiment of the present specification, n2 is an integer from 0 to 8, and when n2 is 2 or more, 2 or more R2 are the same or different from each other.

According to an exemplary embodiment of the present specification, n3 is an integer from 0 to 8, and when n3 is 2 or more, 2 or more R3 are the same or different from each other.

In one embodiment of the present specification, Formula 1 is represented by any one of the following compounds.

The core structure of the compound represented by Formula 1 according to an exemplary embodiment of the present specification can be manufactured by the same method as the production example described later. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents into the core structure of the above structure.

Additionally, the present specification provides an organic light-emitting device containing the above-mentioned compounds.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In this specification, when a part “includes” a certain element, this means that it may further include other elements rather than excluding other elements, unless specifically stated to the contrary.

The organic light emitting device according to the present specification includes an anode; cathode; And an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes a compound represented by the above-mentioned formula (1).

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes one or more of the organic material layers, a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. It may have a structure that includes However, the structure of the organic light emitting device of the present specification is not limited to this and may include fewer or more organic material layers.

In the organic light emitting device of the present specification, the organic light emitting device includes a light emitting layer, and the light emitting layer may include the compound.

In the organic light emitting device of the present specification, the organic material layer 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 transport layer is a compound represented by the above-mentioned formula 1. It can be included.

In the organic light emitting device of the present specification, the organic material layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by the above-described formula (1).

In one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1.

In one embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and a hole blocking layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer is represented by the above-mentioned formula 1. It may contain compounds.

In one embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound represented by Formula 1.

The organic light emitting device of the present specification may further include one or more organic material layers among a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer. .

In one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The structure of the organic light emitting device of this specification may have the same structure as shown in FIGS. 1 and 2, but is not limited thereto.

Figure 1 illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are sequentially stacked. In this structure, the compound may be included in the light-emitting layer 6.

Figure 2 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( The structure of an organic light emitting device in which 8) and cathode 9 are sequentially stacked is illustrated. In this structure, the compound is included in the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light emitting layer (6), the hole blocking layer (7), or the electron injection and transport layer (8). You can.

In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be provided adjacent to each other. For example, the electron blocking layer and the light emitting layer may be provided in physical contact.

In one embodiment of the present specification, the hole transport layer and the electron blocking layer may be provided adjacent to each other. For example, the hole transport layer and the electron blocking layer may be provided in physical contact with each other.

The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by Chemical Formula 1.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate. Manufactured by depositing an anode, 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 on it. It can be. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic layer may further include 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 a hole injection and transport layer.

The organic light-emitting device of the present specification can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound of Chemical Formula 1 described above.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to ensure smooth hole injection into the organic layer. Specific examples of anode materials 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); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode is an electrode that injects electrons, and the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. The hole injection material is HOMO (highest occupied). It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these.

The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-described compounds or materials known in the art may be used in the electron blocking layer.

The light-emitting 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 that can emit light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

When the light-emitting layer emits red light, the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)). Phosphorescent materials such as iridium), PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these. If the light-emitting 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) can be used as the light-emitting dopant. However, it is not limited to this. When the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer may play a role in facilitating the transport of electrons. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include the above-mentioned compounds or Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.

The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

Hereinafter, in order to explain the present specification in detail, examples will be given in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of this application are provided to more completely explain the present specification to those with average knowledge in the art.

< Manufacturing example >

Preparation Example 1. Synthesis of Compound 1

Compound 2-chloro-4-(2-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (6.50 g, 16.50 mmol), a-1, in a 500 ml round bottom flask under nitrogen atmosphere. (8.60, 18.15 mmol) was completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (1.01g, 0.88 mmol) was added, and heated for 3 hours. It was stirred. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 320 ml of tetrahydrofuran to prepare Compound 1 (5.84 g, 50%).

MS[M+H] ⁺ = 706

*

Preparation Example 2. Synthesis of Compound 2

Compound 2-chloro-4-(2-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazine (6.50 g, 16.50 mmol), and compound in a 500 mL round bottom flask under nitrogen atmosphere. After completely dissolving a-1 (8.03 g, 18.15 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.57 g, 0.49 mmol) was added. After addition, it was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of ethyl acetate to prepare Compound 2 (7.88 g, 68%).

MS[M+H] ⁺ = 706

Preparation Example 3. Synthesis of Compound 3

Compound 2-chloro-4-(2-(phenanthren-9-yl)phenyl)-6-phenyl-1,3,5-triazine (6.50 g, 16.50 mmol), and compound in a 500 mL round bottom flask under nitrogen atmosphere. After completely dissolving a-2 (9.51 g, 18.15 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.57 g, 0.49 mmol) was added. After addition, it was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 320 mL of tetrahydrofuran to prepare Compound 3 (8.11 g, 65%).

MS[M+H] ⁺ = 756

Preparation Example 4. Synthesis of Compound 4

Compound 2-chloro-4-(2-(fluoranthen-3-yl)phenyl)-6-phenyl-1,3,5-triazine (6.50 g, 15.63 mmol), and compound in a 500 mL round bottom flask under nitrogen atmosphere. After completely dissolving a-1 (9.01 g, 17.19 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added. After addition, it was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 mL of tetrahydrofuran to prepare Compound 4 (7.55 g, 62%).

MS[M+H] ⁺ = 780

Preparation Example 5. Synthesis of Compound 5

Compound 2-chloro-4-phenyl-6-(2-(triphenylen-2-yl)phenyl)-1,3,5-triazine (6.50 g, 14.67 mmol), and compound in a 500 mL round bottom flask under nitrogen atmosphere. After completely dissolving a-2 (8.46 g, 16.14 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.51 g, 0.44 mmol) was added. After addition, it was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of tetrahydrofuran to prepare Compound 5 (7.32 g, 62%).

MS[M+H] ⁺ = 807

Preparation Example 6. Synthesis of Compound 6

Compound 2-chloro-4-(2-(phenanthren-3-yl)phenyl)-6-phenyl-1,3,5-triazine (6.50 g, 14.67 mmol), and compound in a 500 mL round bottom flask under nitrogen atmosphere. After completely dissolving a-3 (7.65 g, 16.14 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.51 g, 0.44 mmol) was added. After addition, it was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 330 mL of ethyl acetate to prepare Compound 6 (6.81 g, 61%).

MS[M+H] ⁺ = 756

Preparation Example 7. Synthesis of Compound 7

Compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(2-(naphthalen-1-yl)phenyl)-1,3,5 in a 500 ml round bottom flask under nitrogen atmosphere. -triazine (6.50 g, 15.59 mmol) and a-1 (8.13 g, 17.15 mmol) were completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, and tetrakis-(triphenylphosphine)palladium was added. (0.54 g, 0.47 mmol) was added and heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to prepare Compound 7 (5.47 g, 45%).

MS[M+H] ⁺ = 782

Preparation Example 8. Synthesis of Compound 8

Compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(2-(naphthalen-2-yl)phenyl)-1,3,5 in a 500 ml round bottom flask under nitrogen atmosphere. -triazine (6.50 g, 15.59 mmol) and a-2 (8.13 g, 17.15 mmol) were completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, and tetrakis-(triphenylphosphine)palladium was added. (0.54 g, 0.47 mmol) was added and heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 330 ml of ethyl acetate to prepare Compound 8 (6.34 g, 52%).

MS[M+H] ⁺ = 782

Preparation Example 9. Synthesis of Compound 9

Compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(2-(phenanthren-9-yl)phenyl)-1,3, in a 500 mL round bottom flask under nitrogen atmosphere. 5-triazine (6.50 g, 13.89 mmol) and compound a-3 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(tri Phenylphosphine)palladium (0.48 g, 0.42 mmol) was added and heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare Compound 9 (7.22 g, 62%).

MS[M+H] ⁺ = 833

Preparation Example 10. Synthesis of Compound 10

Compound 2-chloro-4-(2-(dibenzo[b,d]furan-2-yl)phenyl)-6-(naphthalen-1-yl)-1,3,5 in a 500 mL round bottom flask under nitrogen atmosphere. -triazine (6.50 g, 15.12 mmol) and compound a-1 (7.88 g, 16.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenyl Phosphine) palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 340 mL of ethyl acetate to prepare Compound 10 (6.88 g, 57%).

MS[M+H] ⁺ = 796

Preparation Example 11. Synthesis of Compound 11

Compound 2-chloro-4-(2-(dibenzo[b,d]thiophen-3-yl)phenyl)-6-(naphthalen-2-yl)-1,3,5 in a 500 mL round bottom flask under nitrogen atmosphere. -triazine (6.50 g, 14.54 mmol) and compound a-2 (7.58 g, 16.01 mmol) were completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenyl Phosphine) palladium (0.50 g, 0.44 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 mL of tetrahydrofuran to prepare Compound 11 (7.37 g, 62%).

MS[M+H] ⁺ = 813

<Experimental example>

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

On the ITO transparent electrode, which is the anode prepared in this way, the compounds of the following compound HI1 and the following compound HI2 were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by the following chemical formula HT1 on the hole injection layer. Subsequently, the compound of EB1 was vacuum deposited with a film thickness of 50 Å on the hole transport layer to form an electron blocking layer. Subsequently, a compound represented by the following formula BH and a compound represented by the following formula BD were vacuum deposited on the electron blocking layer at a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer. Compound 1 synthesized in Preparation Example 1 was vacuum deposited on the light emitting layer with a film thickness of 50 Å to form a hole blocking layer. Next, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic matter was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ An organic light emitting device was manufactured by maintaining 5×10 ^-6 torr.

Example 1-2 to Example 1-11

An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1.

Comparative Examples 1-1 to 1-6

An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1. The compounds HB1, HB2, HB3, HB4, HB5 and HB6 used in Table 1 below are as follows.

When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinate, and lifespan were measured, and 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%.

compound
(hole blocking layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1-1 Compound 1 4.59 6.37 (0.146, 0.046) 250 Example 1-2 compound 2 4.54 6.44 (0.145, 0.045) 285 Example 1-3 Compound 3 4.52 6.23 (0.146, 0.046) 255 Example 1-4 Compound 4 4.56 6.25 (0.146, 0.045) 280 Examples 1-5 Compound 5 4.57 6.29 (0.145, 0.045) 285 Example 1-6 Compound 6 4.58 6.28 (0.146, 0.045) 255 Example 1-7 Compound 7 4.58 6.21 (0.145, 0.047) 250 Examples 1-8 Compound 8 4.59 6.24 (0.145, 0.045) 285 Example 1-9 Compound 9 4.53 6.23 (0.147, 0.046) 250 Examples 1-10 Compound 10 4.63 6.14 (0.145, 0.046) 275 Example 1-11 Compound 11 4.62 6.17 (0.145, 0.046) 275 Comparative Example 1-1 HB1 4.81 5.73 (0.145, 0.045) 120 Comparative Example 1-2 HB2 4.88 5.64 (0.145, 0.045) 105 Comparative Example 1-3 HB3 4.93 5.82 (0.145, 0.045) 160 Comparative Example 1-4 HB4 4.84 5.71 (0.145, 0.045) 60 Comparative Example 1-5 HB5 4.86 5.68 (0.145, 0.45) 35 Comparative Example 1-6 HB6 4.92 5.89 (0.145, 0.045) 145

As shown in Table 1, the organic light-emitting device using the compound of the present invention with a triazine substituent linked to the spiro[fluorene-9,9'-thioxanthene] core as a hole blocking layer has the efficiency, driving voltage, and It showed excellent characteristics in terms of stability.

Although the preferred embodiment (hole blocking layer) of the present invention has been described above, the present invention is not limited thereto and can be implemented with various modifications within the scope of the claims and the detailed description of the invention. It belongs to the category of invention.

1: substrate
2: Anode
3: Hole injection layer
4: Hole transport layer
5: Electronic blocking layer
6: Light-emitting layer
7: Hole blocking layer
8: Electron injection and transport layer
9: cathode

Claims (10)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
L1 and L2 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted aryl group,
A is a substituted or unsubstituted 2 or more ring condensed aryl group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group,
R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
n1 is an integer from 0 to 7, n2 is an integer from 0 to 8, and n3 is an integer from 0 to 4. When n1 to n3 are each 2 or more, two or more substituents in parentheses are the same or different from each other. In claim 1,
Formula 1 is a compound represented by any one of the following formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
The definitions of L1, L2, Ar1, A, R1 to R3 and n1 to n3 are the same as in Formula 1 above. In claim 1,
L1 and L2 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms. The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. anode; cathode; And an organic light-emitting device comprising one or more organic material layers provided between the anode and the cathode, wherein one or more layers of the organic material layers include the compound according to any one of claims 1 to 4. In claim 5,
An organic light-emitting device wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound. In claim 5,
The organic material layer 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 transport layer includes the compound. In claim 5,
An organic light emitting device wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound. In claim 5,
The organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer includes the compound. In claim 5,
An organic light emitting device wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.