KR102630968B1 - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light-emitting device including a compound represented by Formula 1 and a compound represented by Formula 2.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of Korean Patent Application No. 10-2019-0099429 filed with the Korea Intellectual Property Office on August 14, 2019, the entire contents of which are incorporated herein by reference.

This specification relates to organic light emitting devices.

Organic light emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then annihilate, emitting light. The organic thin film may be composed of a single layer or multiple layers as needed.

Most of the materials used in organic light-emitting devices are pure organic materials or complexes of organic materials and metals. Depending on the application, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be divided into: Here, organic materials with p-type properties, that is, organic materials that are easily oxidized and have an electrochemically stable state upon oxidation, are mainly used as hole injection materials or hole transport materials. Meanwhile, organic materials with n-type properties, that is, organic materials that are easily reduced and have an electrochemically stable state upon reduction, are mainly used as electron injection materials or electron transport materials. The emitting layer material is preferably a material that has both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, and excitons are formed when holes and electrons recombine in the emitting layer. A material with high luminous efficiency that converts light into light is desirable.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

Korean Patent Publication No. 10-2006-0009932

Described herein are organic light-emitting devices having low driving voltage, high efficiency, or long lifespan characteristics.

One embodiment of this specification is

first electrode;

second electrode;

a light emitting layer provided between the first electrode and the second electrode;

A first organic layer provided between the first electrode and the light emitting layer; and

An organic light-emitting device comprising a second organic material layer provided between the second electrode and the light-emitting layer,

The first organic layer includes a compound represented by the following formula (1),

The second organic material layer provides an organic light-emitting device including a compound represented by the following formula (2).

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or adjacent groups can combine with each other to form a ring,

n is an integer from 1 to 8, and when it is 2 or more, R1 is the same as or different from each other,

[Formula 2]

In Formula 2,

L is a direct bond; Substituted or unsubstituted arylene group; 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,

Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted arylalkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl 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 are each independently hydrogen; heavy hydrogen; Cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylphosphine group; Substituted or unsubstituted phosphine oxide group; 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 a compound represented by Formula 2 in the second organic material layer, thereby providing an organic light emitting device having low driving voltage, high efficiency, and/or long lifespan. provides.

Figure 1 shows an example of an organic light emitting device consisting of 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.
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), and electron transport and injection layer. An example of an organic light emitting device consisting of (8) and a cathode (9) is shown.

Hereinafter, this specification will be described in more detail.

first electrode; second electrode; a light emitting layer provided between the first electrode and the second electrode; A first organic layer provided between the first electrode and the light emitting layer; And an organic light-emitting device comprising a second organic layer provided between the second electrode and the light-emitting layer, wherein the first organic layer includes a compound represented by Formula 1 below, and the second organic layer is represented by Formula 2 below: An organic light emitting device containing a compound is provided.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or adjacent groups can combine with each other to form a ring,

n is an integer from 1 to 8, and when it is 2 or more, R1 is the same as or different from each other,

[Formula 2]

In Formula 2,

L is a direct bond; Substituted or unsubstituted arylene group; 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,

Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted arylalkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl 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 are each independently hydrogen; heavy hydrogen; Cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylphosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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, means a position bonded to a chemical formula or 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; Cyano group; nitro group; imide group; amide group; carbonyl group; ether group; ester group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; alkenyl group; silyl group; boron group; Amine group; Arylphosphine group; Phosphine oxide group; Aryl group; It means that it is substituted with one or two or more substituents selected from the group consisting of heteroaryl groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents. 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; Cyano group; Alkyl group; Cycloalkyl group; silyl group; Aryl group; It means that it is substituted with one or two or more substituents selected from the group consisting of heteroaryl groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; Alkyl group; silyl group; Aryl group; It means that it is substituted with one or two or more substituents selected from the group consisting of heteroaryl groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.

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 this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.

In the present specification, the ester group may be -C(=O)OR ₁₀₅ or -OC(=O)R ₁₀₆ , where R ₁₀₅ and R ₁₀₆ are the same or different from each other, and are each independently hydrogen, substituted or It may be 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; Alkenyl group having 1 to 25 carbon atoms; Aryl group having 6 to 30 carbon atoms; Alternatively, it may be substituted with a heterocyclic group having 2 to 30 carbon atoms. In one embodiment of the present specification, the oxygen is an alkyl group having 1 to 10 carbon atoms; Alkenyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or it is substituted with a heterocyclic group having 2 to 20 carbon atoms.

In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be replaced with hydrogen, a straight-chain, branched-chain, or ring-chain 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.

In the present specification, the silyl group may be represented by the formula -SiY _a Y _b Y _c , where Y _a , Y _b and Y _c are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.

In the present specification, the boron group may be represented by the chemical formula -BY _{dY e} , where Y _d and Y _e are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.

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 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, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, It may be n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

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 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, etc., but are 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 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 this specification, the alkyl groups in the alkylthioxy group and the alkylsulfoxy group are the same as the examples of the alkyl groups described above. Specifically, alkylthioxy groups include methylthioxy group, ethylthioxy group, tert-butylthioxy group, hexylthioxy group, octylthioxy group, etc., and alkylsulfoxy groups include methylsulfoxy group, ethylsulfoxy group, propylsulfoxy group, and butyl group. There is a sulphoxyl group, etc., but it is not limited to this.

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 include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.

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 in the aryloxy group.

In this specification, the aryl group in the arylthioxy group and arylsulfoxy group is the same as the example of the aryl group described above.

In the present specification, the heterocyclic group is a cyclic group containing one or more elements such as N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. 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 may be applied, except that the heteroaryl group is aromatic.

In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” refers to a hydrocarbon ring; Or it means 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, except for the divalent 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.

The description of the aryl group can be applied, except that the arylene group is divalent.

The description of the heteroaryl group can be applied, except that the heteroarylene group is divalent.

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.

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or adjacent groups can combine with each other to form a ring,

n is an integer from 1 to 8, and when n is 2 or more, 2 or more R1s are the same or different from each other.

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 hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 60 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 an exemplary embodiment of the present specification, Ar1 and Ar2 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 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 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, Ar1 and Ar2 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 alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

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 hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

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 hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently an aryl group substituted or unsubstituted by an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents a monocyclic to tetracyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tetracyclic aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents a monocyclic to tricyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tricyclic aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents 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.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents 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.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same 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.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents 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.

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 substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted fluorenyl group.

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 phenyl group substituted or unsubstituted by an alkyl group or an aryl group; Biphenyl group substituted or unsubstituted with an alkyl group or an aryl group; A naphthyl group substituted or unsubstituted by an alkyl group or an aryl group; A phenanthrenyl group substituted or unsubstituted by an alkyl group or an aryl group; Terphenyl group substituted or unsubstituted with an alkyl group or aryl group; Or it is a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

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 phenyl group substituted or unsubstituted by an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrenyl group substituted or unsubstituted with an aryl group; Terphenyl group substituted or unsubstituted with an aryl group; Or it is a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

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 phenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms; A biphenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms; A naphthyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms; A phenanthrenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms; A terphenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms; Or it is 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.

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 phenyl group substituted or unsubstituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; A naphthyl group substituted or unsubstituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; A phenanthrenyl group substituted or unsubstituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; A terphenyl group unsubstituted or substituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; Or it is a fluorenyl group unsubstituted or substituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group.

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 phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A naphthyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A phenanthrenyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A terphenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Or it is a fluorenyl group substituted or unsubstituted with a methyl group.

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 phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; naphthyl group; phenanthrenyl group; Terphenyl group; Or it is a fluorenyl group substituted or unsubstituted with a methyl group.

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 phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; phenanthrenyl group; Terphenyl group; Or it is a dimethyl fluorenyl group.

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 phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Terphenyl group; Or it is a dimethyl fluorenyl group.

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 phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Or it is a terphenyl group.

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 phenyl group substituted or unsubstituted by a phenyl group or a naphthyl group; Biphenyl group; Or it is a terphenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and may each independently be selected from the structures below.

In the above structure, dotted lines indicate binding positions.

In the above structure, R6 is an alkyl group or an aryl group.

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.

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.

In the above structure, R6 is a methyl group or phenyl group.

In the above structure, R6 is a methyl group.

In the above structure, R7 is a substituted or unsubstituted aryl group.

In the above structure, R7 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and may each independently be selected from the structures below.

In the above structure, dotted lines indicate binding positions.

According to an exemplary embodiment of the present specification, Ar1 is expressed as -L101-Ar101, and Ar2 is expressed as -L102-Ar102.

According to an exemplary embodiment of the present specification, L101 and L102 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L101 and L102 are the same or different from each other and are each independently directly bonded; Or it is an arylene group.

According to an exemplary embodiment of the present specification, L101 and L102 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 an exemplary embodiment of the present specification, L101 and L102 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.

According to an exemplary embodiment of the present specification, L101 and L102 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 20 carbon atoms.

According to an exemplary embodiment of the present specification, L101 and L102 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to an exemplary embodiment of the present specification, L101 and L102 are the same or different from each other and are each independently directly bonded; phenylene group; Or it is a biphenylene group.

According to an exemplary embodiment of the present specification, L101 and L102 are the same or different from each other and are each independently directly bonded; Or it is a phenylene group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other and are each independently a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently an aryl group substituted or unsubstituted by an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and each independently represents 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.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently an aryl group of 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and each independently represents a monocyclic to tetracyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tetracyclic aryl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same 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.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.

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 a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted fluorenyl group.

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 a phenyl group substituted or unsubstituted by an alkyl group or an aryl group; Biphenyl group substituted or unsubstituted by an alkyl group or an aryl group; A naphthyl group substituted or unsubstituted by an alkyl group or an aryl group; A phenanthrenyl group substituted or unsubstituted by an alkyl group or an aryl group; Terphenyl group substituted or unsubstituted with an alkyl group or aryl group; Or it is a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.

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 a phenyl group substituted or unsubstituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; A naphthyl group substituted or unsubstituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; A phenanthrenyl group substituted or unsubstituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; A terphenyl group unsubstituted or substituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group; Or it is a fluorenyl group unsubstituted or substituted with a methyl group, phenyl group, naphthyl group, or phenanthrenyl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A naphthyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A phenanthrenyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A terphenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Or it is a fluorenyl group substituted or unsubstituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; naphthyl group; phenanthrenyl group; Terphenyl group; Or it is a fluorenyl group substituted or unsubstituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; naphthyl group; phenanthrenyl group; Terphenyl group; Or it is a dimethyl fluorenyl group.

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 a phenyl group; Biphenyl group; Terphenyl group; naphthyl group; phenanthrenyl group; Or it is a fluorenyl group substituted or unsubstituted with a methyl group.

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 a phenyl group; Biphenyl group; Terphenyl group; Or it is a naphthyl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups are combined with each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Alternatively, it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is hydrogen; Or, it is deuterium, or combines with adjacent groups to form an aromatic hydrocarbon ring that is condensed to carbazole.

According to an exemplary embodiment of the present specification, R1 is hydrogen or combines with adjacent groups to form an aromatic hydrocarbon ring that is condensed to carbazole.

According to an exemplary embodiment of the present specification, R1 is hydrogen or combines with adjacent groups to form a benzene ring that is condensed to carbazole.

According to an exemplary embodiment of the present specification, R1 is hydrogen.

According to an exemplary embodiment of the present specification, R1 combines with adjacent groups to form a benzene ring that is condensed to carbazole.

According to an exemplary embodiment of the present specification, n is an integer from 1 to 8, and when n 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, n is 1.

According to an exemplary embodiment of the present specification, n is 2.

According to one embodiment of the present specification, n is 8.

According to an exemplary embodiment of the present specification, in Formula 1, when N of carbazole is connected to the ortho or meta position of the biphenylene group connected to the amine group, the voltage, efficiency, or lifespan characteristics are further increased. .

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, the definitions of Ar1, Ar2, R1, and n are the same as those in Formula 1.

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.

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-3 to 1-6, the definitions of Ar1 and Ar2 are the same as those in Formula 1,

G1 and G2 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; 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,

When g1 is 2 or more, two or more G1's are the same as or different from each other, and when g2 is 2 or more, two or more G2's are the same or different from each other.

According to an exemplary embodiment of the present specification, G1 and G2 are the same or different from each other and are hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, G1 and G2 are hydrogen.

According to an exemplary embodiment of the present specification, g1 is 1.

According to one embodiment of the present specification, g1 is 10.

According to an exemplary embodiment of the present specification, g2 is 1.

According to one embodiment of the present specification, g2 is 8.

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.

Hereinafter, Chemical Formula 2 will be described in detail.

[Formula 2]

In Formula 2,

L is a direct bond; Substituted or unsubstituted arylene group; 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,

Ar3 and Ar4 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted arylalkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl 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 are each independently hydrogen; heavy hydrogen; Cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylphosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, L is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or it is a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; phenylene group; Or it is a biphenylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; Or it is a phenylene group.

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.

In the above structure, dotted lines indicate binding positions.

In the above structure, R101 to R103 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R101 to R103 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, R101 and R102 are the same or different from each other and are each independently a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, R103 is a phenyl group.

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.

In the above structural formula, the dotted line indicates the binding position.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted arylalkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently 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 an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently 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, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to hexacyclic aryl group; Or it is a substituted or unsubstituted mono- to 6-ring heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to pentacyclic aryl group; Or it is a substituted or unsubstituted mono- to 5-ring heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or it is a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; Or it is a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or two of the above-mentioned substituents. Aryl group substituted or unsubstituted with more than two groups linked; Or, it is a heteroaryl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or a group in which two or more of the above-mentioned substituents are linked.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently an aryl group substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkylsilyl group, an alkyl group, or an aryl group; Or it is a heteroaryl group substituted or unsubstituted with deuterium, halogen group, cyano group, alkylsilyl group, alkyl group, or aryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a phenyl group; Biphenyl group; Terphenyl group; naphthyl group; phenanthrenyl group; Triphenylenyl group; fluorenyl group; Dibenzofuran group; or a dibenzothiophene group, and the groups may be substituted or unsubstituted with one or more groups from the group consisting of deuterium, halogen group, cyano group, alkylsilyl group, alkyl group, and aryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or two of the above-mentioned substituents. A phenyl group substituted or unsubstituted with more than one group linked; A biphenyl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or a group in which two or more of the above-mentioned substituents are linked; A terphenyl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or a group in which two or more of the above-mentioned substituents are linked; A naphthyl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group and aryl group, or a group in which two or more of the above-mentioned substituents are linked; A phenanthrenyl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group and aryl group, or a group in which two or more of the above-mentioned substituents are linked; A triphenylenyl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or a group in which two or more of the above-mentioned substituents are linked; A fluorenyl group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group and aryl group, or a group in which two or more of the above-mentioned substituents are linked; A dibenzofuran group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or a group in which two or more of the above-mentioned substituents are linked; Or it is a dibenzothiophene group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or a group in which two or more of the above-mentioned substituents are linked.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently one or more groups selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, and aryl group, or two of the above-mentioned substituents. A phenyl group substituted or unsubstituted with two or more groups linked together; Biphenyl group substituted or unsubstituted with deuterium or cyano group; Terphenyl group; Naphthyl group substituted or unsubstituted with an aryl group; phenanthrenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; Dibenzofuran group; Or it is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and each independently represents deuterium, fluoro group (-F), cyano group, silyl group, methyl group, t-butyl group, phenyl group, naphthyl group, and A phenyl group substituted or unsubstituted with one or more groups selected from the group consisting of a phenanthrenyl group or a group in which two or more of the above-mentioned substituents are connected; Biphenyl group substituted or unsubstituted with a cyano group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrenyl group; Triphenylenyl group; Fluorenyl group substituted or unsubstituted with a methyl group; Dibenzofuran group; Or it is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently selected from deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenene. A phenyl group substituted or unsubstituted with a trenyl group; Biphenyl group substituted or unsubstituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group; Terphenyl group substituted or unsubstituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group; Naphthyl group substituted or unsubstituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group; Phenanthrenyl group substituted or unsubstituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group; A triphenylenyl group unsubstituted or substituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group; A fluorenyl group unsubstituted or substituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group; Dibenzofuran group substituted or unsubstituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group and phenanthrenyl group; or a dibenzothiophene group unsubstituted or substituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, and phenanthrenyl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, or phenene. A phenyl group substituted or unsubstituted with a trenyl group; A biphenyl group unsubstituted or substituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, or phenanthrenyl group; Terphenyl group substituted or unsubstituted with deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, or phenanthrenyl group; A naphthyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A phenanthrenyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; A triphenylenyl group substituted or unsubstituted with a phenyl group, naphthyl group, or phenanthrenyl group; dimethyl fluorenyl group; Dibenzofuran group; Or it is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents deuterium, fluoro group (-F), cyano group, trimethylsilyl group, t-butyl group, phenyl group, naphthyl group, or phenene. A phenyl group substituted or unsubstituted with a trenyl group; Biphenyl group substituted or unsubstituted with a cyano group; Terphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; phenanthrenyl group; Triphenylenyl group; dimethyl fluorenyl group; Dibenzofuran group; Or it is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by a naphthyl group; Biphenyl group; Or it is a terphenyl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by a naphthyl group; Or it is a terphenyl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and may each independently be selected from the following structures.

The structure is substituted or unsubstituted with deuterium, halogen group, cyano group, alkylsilyl group, or alkyl group, and the dotted line indicates the bonding position.

The above structure is substituted or provided with deuterium, fluoro group (-F), cyano group, trimethylsilyl group or t-butyl group.

In the above structure, R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

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.

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.

In the above structure, R6 is a methyl group; Or it is a phenyl group.

In the above structure, R7 is a substituted or unsubstituted aryl group.

In the above structure, R7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the above structure, R7 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the above structure, R7 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In the above structure, R7 is a phenyl group; Or it is a naphthyl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and may each independently be selected from the following structures.

The structure is substituted or unsubstituted with deuterium, halogen group, cyano group, alkylsilyl group or alkyl group, the dotted line indicates the bonding position, and the definition of R6 is as described above.

According to an exemplary embodiment of the present specification, one of Ar3 and Ar4 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are substituted or unsubstituted aryl groups and are different from each other.

According to an exemplary embodiment of the present specification, X1 is N; or CR11, and X2 is N; or CR12, and X3 is N; or CR13, and at least one of X1 to X3 is N.

According to an exemplary embodiment of the present specification, at least one of X1 to X3 is N.

According to an exemplary embodiment of the present specification, at least two of X1 to X3 are N.

According to an exemplary embodiment of the present specification, X1, X2, and X3 are N.

According to an exemplary embodiment of the present specification, X1 and X2 are N, and X3 is CR13.

According to an exemplary embodiment of the present specification, X1 and X3 are N, and X2 is CR12.

According to an exemplary embodiment of the present specification, X2 and X3 are N, and X1 is CR11.

According to an exemplary embodiment of the present specification, X1 is N, X2 is CR12, and X3 is CR13.

According to an exemplary embodiment of the present specification, X2 is N, X1 is CR11, and X3 is CR13.

According to an exemplary embodiment of the present specification, X3 is N, X1 is CR11, and X2 is CR12.

According to an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; 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, R11 to R13 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R11 to R13 are hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, R11 to R13 are hydrogen.

According to an exemplary embodiment of the present specification, Formula 2 is represented by any one of the following Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

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.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is represented by any of the following structural formulas.

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 into the core structure of the above structure.

The organic light-emitting device of the present invention forms a first organic layer between the first electrode and the light-emitting layer using the compound of Formula 1 described above, and forms a second organic layer between the second electrode and the light-emitting layer using the compound of Formula 2. Except for this, it can be manufactured using conventional organic light emitting device manufacturing methods and materials.

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 organic material layer of the organic light emitting device of the present invention 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 layers 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 that does. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.

The organic light-emitting device of the present invention includes a light-emitting layer, the first organic layer provided between the first electrode and the light-emitting layer contains a compound represented by Formula 1, and the second organic layer provided between the second electrode and the light-emitting layer contains a compound represented by Formula 2. Includes compounds that are

According to one example, the thickness of the organic material layer containing the compound of Formula 1 is 30Å to 300Å, and preferably 50Å to 200Å.

According to one example, the thickness of the organic material layer containing the compound of Formula 2 is 30Å to 500Å, preferably 50Å to 400Å.

According to one 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 layer And the transport layer includes a compound represented by Formula 1 above.

According to one 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, the hole transport layer, or the hole injection layer may be a hole injection layer, a hole transport layer, or a hole injection and transport layer. And the transport layer may include a compound represented by Formula 1 above.

According to one 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 an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1.

According to one 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 is an electron blocking layer, and the electron blocking layer may include the compound represented by Formula 1 above.

According to one example, the second organic layer provided between the second electrode and the light-emitting 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 layer And the transport layer includes a compound represented by Formula 1 above.

According to one example, the second organic material layer provided between the second electrode and the light-emitting 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 may be an electron injection layer, an electron transport layer, or an electron injection and transport layer. And the transport layer may include a compound represented by Formula 1 above.

According to one example, the second organic material layer provided between the second electrode and the light-emitting layer of the organic light-emitting device of the present invention includes a hole blocking layer, and the hole blocking layer includes the compound represented by Formula 2 above.

According to one example, the second organic material layer provided between the second electrode and the light-emitting layer of the organic light-emitting device of the present invention is a hole blocking layer, and the hole blocking layer may include the compound represented by Formula 2 above.

In another embodiment, the first organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1.

In another embodiment, the second organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 2.

The organic light emitting device of the present invention may further include one or more organic material layers 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. You can.

According to one example, the first organic material layer is in contact with the light emitting layer. Here, contact means that no other organic material layer exists between the light-emitting layer and the first organic material layer.

According to one example, the second organic material layer is in contact with the light emitting layer. Here, contact means that no other organic material layer exists between the light emitting layer and the second organic material layer.

In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and materials known in the art may be used as the electron blocking layer.

According to one example, the second organic material layer is in contact with the hole blocking layer. Here, contact means that no other organic material layer exists between the hole blocking layer and the second organic material layer.

In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

The organic light emitting device may have, for example, a stacked structure as shown below, but is not limited thereto.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode

(15) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(18) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule

(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) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport and injection layer/cathode

The structure of the organic light emitting device of the present invention 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, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, and a cathode 9 are sequentially stacked. . In this 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.

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), and electron transport and injection layer. The structure of an organic light emitting device in which (8) and the cathode (9) are sequentially stacked is illustrated. In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 are the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light emitting layer (6), and the hole blocking layer. It may be included in layer 7 or electron transport and injection layer 8.

For example, the organic light emitting device according to the present invention deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. 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 thereon. 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 transport and injection layer.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs electron injection and electron transport, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is limited thereto. It may not be a single layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.

The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to facilitate 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 preferably a material with a low 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 multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

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. HOMO (highest occupied) of the hole injection material 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 thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.

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 additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

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 capable of emitting 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 heterocycle-containing 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, 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)iridium). ), phosphorescent materials such as 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. If 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 inject 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 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 in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.

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 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.

Preparation Examples A to C: Preparation of intermediates A to C

Intermediates A to C were prepared through the same process as above.

Preparation Example 1: Preparation of Compound 1-1

Compound N-(4-bromophenyl)-N-(4-(naphthalen-1-yl)phenyl)-[1,1':4',1''-terphenyl in a 500 ml round bottom flask under nitrogen atmosphere. ]-4-amine (N-(4-bromophenyl)-N-(4-(naphthalen-1-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine) ( 12.32 g, 20.50 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (6.47g, 22.55 mmol) After completely dissolving in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis-(triphenylphosphine)palladium (0.42 g, 0.37 mmol) was added, and the mixture 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 350 ml of ethyl acetate to prepare Compound 1-1 (11.29 g, 72%).

MS[M+H] ⁺ = 765

Preparation Example 2: Preparation of Compound 1-2

Compound 4-bromo-N,N-bis(4-(naphthalen-2-yl)phenyl)aniline (4-bromo-N,N-bis(4-(naphthalen-2)) was added to a 500 ml round bottom flask in a nitrogen atmosphere. -yl)phenyl)aniline) (11.09 g, 19.25 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (6.08 g, 21.18 mmol) was completely dissolved in 240 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58 mmol) was added, and then 3 It was heated and stirred for an hour. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare Compound 1-2 (8.88 g, 62%).

MS[M+H] ⁺ = 739

Preparation Example 3: Preparation of Compound 1-3

Compound N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1':3',1'' in a 500 ml round bottom flask under nitrogen atmosphere. -terphenyl]-4'-amine (N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1':3',1''-terphenyl] -4'-amine) (10.55g, 19.11 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) ( 6.03g, 21.02 mmol) was completely dissolved in 240 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.66g, 0.57 mmol) was added and incubated for 4 hours. It was heated and stirred for a while. 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 ethyl acetate to prepare Compound 1-3 (9.07 g, 66%).

MS[M+H] ⁺ = 715

Preparation Example 4: Preparation of Compound 2-1

Compound A (11.71 g, 25.56 mmol), 2-([1,1':2',1''-terphenyl]-4-yl)-4-chloro-6-phenyl, in a 500 ml round bottom flask under nitrogen atmosphere. -1,3,5-triazine (2-([1,1':2',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) (9.76, 23.24mmol) was completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.81g, 0.70mmol) was added, and heated for 7 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 260 ml of tetrahydrofuran to prepare Compound 2-1 (10.02 g, 60%).

MS[M+H] ⁺ = 716

Preparation Example 5: Preparation of Compound 2-2

Compound B (10.95 g, 23.90 mmol), 2-chloro-4-(3-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine ( 2-chloro-4-(3-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine) (8.56, 21.73mmol) was completely dissolved in 280ml of tetrahydrofuran and then dissolved in 2M potassium carbonate solution. (140ml) was added, tetrakis-(triphenylphosphine)palladium (0.81g, 0.70mmol) was added, and the mixture 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 290 ml of acetonitrile to prepare Compound 2-2 (7.96 g, 53%).

MS[M+H] ⁺ = 690

Preparation Example 6: Preparation of Compound 2-3

Compound C (12.26 g, 26.76 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2-(3-bromophenyl) in a 500 ml round bottom flask under nitrogen atmosphere. )-4,6-diphenyl-1,3,5-triazine) (9.44g, 24.33mmol) was completely dissolved in 260ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (130ml) was added, and tetrakis-(triphenylphos) Pin) Palladium (0.84g, 0.73mmol) 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 260 ml of tetrahydrofuran to prepare Compound 2-3 (8.36 g, 54%).

MS[M+H] ⁺ = 640

Comparative Example 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 prepared in this way, compounds of the following formula [HI-1] and the following formula [HI-2] were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer.

The following compound [HT-1] (1150 Å), a material that transports holes, was vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, the following compound [EB-1] (150 Å) was vacuum deposited on the hole transport layer to a film thickness of 50 Å to form an electron blocking layer.

Next, [BH-1] and [BD-1] as shown below were vacuum deposited on the electron blocking layer to a film thickness of 200 Å at a weight ratio of 40:1 to form a light emitting layer.

The compound [HB-1] was vacuum deposited on the light emitting layer to a film thickness of 50 Å to form a hole blocking layer.

Next, compound [ET-1] and the compound LiQ (Lithium Quinolate) 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 300 Å.

A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 2,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic materials 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 2×10 ^- An organic light emitting device was manufactured by maintaining ⁷ to 5×10 ^-6 torr.

Experimental Example 1-1 to Experimental Example 1-9

An organic light-emitting device was manufactured in the same manner as Comparative Example 1, except that the compounds listed in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.

Comparative Examples 2 to 14

An organic light-emitting device was manufactured in the same manner as Comparative Example 1, except that the compounds listed in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.

When a current of 10 mA/cm ² was applied to the organic light-emitting device manufactured in the above experimental and comparative examples, the driving voltage, luminous efficiency, and color coordinates were measured, and at a current density of 10 mA/cm ² , the initial luminance was 95% compared to the initial luminance. The time to reach % (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%.

compound
(electron blocking layer) compound
(Electron injection and transport layer) Voltage
(V
@10mA
/cm ² ) efficiency
(cd/A
@10mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Comparative Example 1 EB-1 ET-1 5.11 5.90 (0.147, 0.045) 265 Experimental Example 1-1 1-1 2-1 3.55 6.72 (0.144, 0.046) 380 Experimental Example 1-2 1-1 2-2 3.56 6.63 (0.145, 0.047) 375 Experimental Example 1-3 1-1 2-3 3.57 6.74 (0.146, 0.045) 385 Experimental Example 1-4 1-2 2-1 3.61 6.72 (0.145, 0.046) 365 Experimental Example 1-5 1-2 2-2 3.62 6.65 (0.145, 0.045) 370 Experimental Example 1-6 1-2 2-3 3.63 6.67 (0.144, 0.047) 365 Experimental Example 1-7 1-3 2-1 3.74 6.78 (0.146, 0.046) 360 Experimental Example 1-8 1-3 2-2 3.78 6.71 (0.145, 0.045) 375 Experimental Example 1-9 1-3 2-3 3.79 6.66 (0.145, 0.047) 360 Comparative Example 2 1-1 ET-1 4.35 6.38 (0.144, 0.045) 290 Comparative Example 3 1-2 ET-1 4.31 6.37 (0.145, 0.046) 305 Comparative Example 4 1-3 ET-1 4.33 6.35 (0.145, 0.045) 270 Comparative Example 5 1-1 ET-2 4.57 6.21 (0.146, 0.046) 290 Comparative Example 6 1-1 ET-3 4.19 6.41 (0.146, 0.047) 310 Comparative Example 7 1-2 ET-3 4.17 6.40 (0.145, 0.045) 325 Comparative Example 8 1-3 ET-3 4.18 6.43 (0.146, 0.046) 290 Comparative Example 9 EB-1 2-1 4.31 6.00 (0.144, 0.047) 350 Comparative Example 10 EB-1 2-2 4.32 6.06 (0.146, 0.046) 345 Comparative Example 11 EB-1 2-3 4.35 6.04 (0.145, 0.045) 355 Comparative Example 12 EB-2 ET-1 4.76 6.07 (0.145, 0.046) 205 Comparative Example 13 EB-1 ET-2 4.78 5.43 (0.147, 0.045) 180 Comparative Example 14 EB-2 ET-3 4.67 6.12 (0.145, 0.046) 220

As shown in Table 1, Examples 1-1 to 1-9 use the compounds of Formula 1 and Formula 2 of the present invention in the electron blocking layer and electron transport layer, respectively, and the compounds represented by Formula 1 and Formula 2 Shows the characteristics of devices applied together. Comparative Examples 2 to 11 are those in which 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 the compound represented by Formula 1 The characteristics of a device using only or using only the compound represented by Formula 2 are shown.

Compared to Comparative Examples 1 to 14, the organic light emitting devices of Experimental Examples 1-1 to 1-9 basically exhibit the characteristics of low voltage, high efficiency, and long lifespan. In particular, the compounds of Formula 1 have the characteristics of high efficiency, and the compounds of Formula 2 have the characteristics of high efficiency. It has the characteristic of long life.

Specifically, the devices of Experimental Examples 1-1 to 1-9 showed that the luminous efficiency was increased by up to about 25% and the lifespan was increased by up to about 115% compared to the comparative example.

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 an electron transport layer, it is possible to have high efficiency characteristics while maintaining the long life characteristics of the organic light emitting device. You can check it.

Although the preferred embodiment of the present invention (combination of the electron blocking layer compound and the electron injection and transport layer compound) has been described above, the present invention is not limited thereto and can be modified in various ways within the scope of the claims and detailed description of the invention. It is possible to implement it by modifying it, and this also falls within the scope of the 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 transport and injection layer
9: cathode

Claims (14)

first electrode;
second electrode;
a light emitting layer provided between the first electrode and the second electrode;
A first organic layer provided between the first electrode and the light emitting layer; and
An organic light-emitting device comprising a second organic material layer provided between the second electrode and the light-emitting layer,
The first organic layer includes a compound represented by the following formula 1-2,
The second organic material layer is an organic light-emitting device comprising a compound represented by the following formula (2):
[Formula 1-2]

In Formula 1-2,
Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R1 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring,
n is an integer from 1 to 8, and when n is 2 or more, 2 or more R1 are the same or different from each other,
[Formula 2]

In Formula 2,
L is a direct bond; Substituted or unsubstituted arylene group; 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,
Ar3 and Ar4 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted arylalkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl 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 are each independently hydrogen; heavy hydrogen; Cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylphosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. delete In claim 1,
Formula 2 is an organic light-emitting device represented by any one of the following formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

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. delete In claim 1,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted terphenyl group; Or an organic light-emitting device that is a substituted or unsubstituted fluorenyl group. In claim 1,
wherein L is a direct bond; Substituted or unsubstituted phenylene group; Or an organic light-emitting device that is a substituted or unsubstituted biphenylene group. In claim 1,
Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group substituted or unsubstituted by an alkyl group or an aryl group. The organic light-emitting device according to claim 1, wherein Formula 1-2 is represented by any one of the following compounds:



. In claim 1,
Formula 2 is an organic light-emitting device represented by any one of the following compounds:













. The method according to claim 1, wherein the first 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 a compound represented by Formula 1-2. An organic light emitting device. The method according to claim 1, wherein the second 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 a compound represented by Formula 2. Organic light emitting device. In claim 1,
An organic light-emitting device wherein the first organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Chemical Formula 1-2. In claim 1,
The second organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 2. In claim 1,
The organic light emitting device further includes one or more organic material layers 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.