KR20220107129A - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device including a compound represented by chemical formula 1 and a compound represented by chemical formula 2. The organic light emitting device includes: a first electrode; a second electrode; a light emitting layer provided between the first electrode and the second electrode; a first organic material layer provided between the first electrode and the light emitting layer; and a second organic material layer provided between the second electrode and the light emitting layer. The purpose of the present invention is to provide an organic light emitting device having low driving voltage, high efficiency and/or long lifespan characteristics.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0099432 filed with the Korean Intellectual Property Office on August 14, 2019, the entire contents of which are incorporated herein by reference.

The present specification relates to an organic light emitting device.

The organic light emitting diode has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

Most of the materials used in organic light emitting devices are pure organic materials or complex compounds in which organic materials and metals are complexed. can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed A material with high luminous efficiency that converts it into light when it is formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

Korean Patent Publication No. 10-2006-0009932

An organic light emitting diode having low driving voltage, high efficiency, and/or long lifespan characteristics is described herein.

An exemplary embodiment of the present specification is

a first electrode;

a second electrode;

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

a first organic material 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 material 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 an aryl group unsubstituted or substituted with an alkyl group or an aryl group,

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

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

[Formula 2]

In Formula 2,

L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,

X1 is N; or CR11, and X2 is N; or CR12, and X3 is N; or CR13;

At least one of X1 to X3 is N,

R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

The organic light emitting device of the present invention includes the compound represented by Formula 1 in the first organic layer and the compound represented by Formula 2 in the second organic layer, thereby having a low driving voltage, high efficiency and/or long life. provides

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , an electron blocking layer 5 , a light emitting layer 6 , a hole blocking layer 7 , and a cathode 9 .
2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport and injection layer An example of an organic light emitting device composed of (8) and a cathode (9) is shown.

Hereinafter, the present specification will be described in more detail.

In the present specification, the first electrode; a second electrode; a light emitting layer provided between the first electrode and the second electrode; a first organic material layer provided between the first electrode and the light emitting layer; and a second organic material layer provided between the second electrode and the light emitting layer, wherein the first organic material layer includes a compound represented by the following formula (1), and the second organic material layer is represented by the following formula (2) An organic light emitting device including the compound is provided.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,

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

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

[Formula 2]

In Formula 2,

L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,

X1 is N; or CR11, and X2 is N; or CR12, and X3 is N; or CR13;

At least one of X1 to X3 is N,

R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

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

는 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification,

denotes a position bonded to a chemical formula or compound.

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

The term "substitution" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; nitro group; imid; amide group; carbonyl group; ether group; ester group; hydroxyl group; an alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; alkenyl group; silyl group; boron group; amine group; an aryl phosphine group; phosphine oxide group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and 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; an alkyl group; cycloalkyl group; silyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.

As used herein, the term "substituted or unsubstituted" refers to deuterium; cyano group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.

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

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

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably from 1 to 40 carbon atoms. Specifically, it may be a compound having 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 , wherein R ₁₀₅ and R ₁₀₆ are the same as or different from each other, and each independently hydrogen, substituted or An unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, but is not limited thereto. Specifically, the oxygen of the ester group is an alkyl group having 1 to 25 carbon atoms; an alkenyl group having 1 to 25 carbon atoms; an aryl group having 6 to 30 carbon atoms; Or it may be substituted with a heterocyclic group having 2 to 30 carbon atoms. In an exemplary embodiment of the present specification, the oxygen is an alkyl group having 1 to 10 carbon atoms; an alkenyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 20 carbon atoms.

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

In the present specification, the amide group may be substituted with a nitrogen of the amide group with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but 2 to 30; 2 to 20; 2 to 10; Or 2 to 5 are preferable. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.

The substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized forms.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the amine group is —NH ₂ , and the amine group may be substituted with the aforementioned 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 an exemplary embodiment, the carbon number of the amine group is 1 to 20. According to an exemplary embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, and a diphenylamine group. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, There is a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but is not limited thereto.

In the present specification, the alkyl group in the alkylthioxy group and the alkylsulfoxy group is the same as the example of the alkyl group described above. Specifically, the alkyl thiooxy group includes methyl thiooxy group, ethyl thiooxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thiooxy group, etc., and the alkyl sulfoxy group includes methyl sulfoxy group, ethyl sulfoxy group, propyl sulfoxy group, There is a sulfoxy group, but is not limited thereto.

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 an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto not.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the aryloxy group.

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

In the present specification, the heterocyclic group is a cyclic group including at least one of elements such as N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.

In the present specification, the description of the above-mentioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.

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

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof. The hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. The heterocycle means a ring including at least one selected from elements such as N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, the aliphatic hydrocarbon ring refers to a ring made of only carbon and hydrogen atoms as a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, However, the present invention is not limited thereto.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, paraazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazaindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but is not limited thereto.

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

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

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment 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, 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 an aryl group unsubstituted or substituted with an alkyl group or an aryl group,

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

n is an integer of 1 to 8, and when n is 2 or more, two or more R1s are the same as 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 each independently represents an aryl group unsubstituted or substituted 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 each independently represent an alkyl group or a monocyclic to 4cyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to 4cyclic aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as 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 as 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 as or different from each other, and are each independently an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted 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 that is unsubstituted or substituted 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 as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted 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 as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms that is 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 each independently a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; a biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; a naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; a phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; a terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; a naphthyl group unsubstituted or substituted with an aryl group; a phenanthrenyl group unsubstituted or substituted with an aryl group; terphenyl group unsubstituted or substituted with an aryl group; or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; a biphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; a naphthyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; a phenanthrenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; a terphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; or a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; a phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; a terphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group; or a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; biphenyl group; naphthyl group; phenanthrenyl group; terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; biphenyl group; phenanthrenyl group; terphenyl group; or a dimethyl fluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; biphenyl group; terphenyl group; or a dimethyl fluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; biphenyl group; or a terphenyl group.

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

In the above structure, the dotted line indicates the bonding position.

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 a phenyl group.

In the above structure, R6 is a methyl group.

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

In the above structure, the dotted line indicates the bonding position.

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

According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; or an arylene group.

According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; phenylene group; or a biphenylene group.

According to an exemplary embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently represents an aryl group unsubstituted or substituted 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 each independently represents an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted 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 as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted 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, Ar101 and Ar102 are the same as or different from each other, and each independently represent an alkyl group or a monocyclic to 4cyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to 4cyclic aryl group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently represent 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 as or different from each other, and each independently represent 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 each independently a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; a biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; a naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; a phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; a terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.

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

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

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

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

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted C6-C30 aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted C2-C30 ring.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 20 alkyl group; Or a substituted or unsubstituted C6-C20 aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring.

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

According to an exemplary embodiment of the present specification, R1 is hydrogen, or an aromatic hydrocarbon ring condensed with carbazole by combining with an adjacent group.

According to an exemplary embodiment of the present specification, R1 is hydrogen, or a benzene ring condensed with carbazole by combining with an adjacent group.

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

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

According to an exemplary embodiment of the present specification, n is an integer of 1 to 8, and when n is 2 or more, two or more R1s are the same 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 an exemplary 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 position 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, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, Ar1, Ar2, R1 and n have the same definitions as in Formula 1 above.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical 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, Ar1 and Ar2 have the same definitions as in Formula 1,

G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

g1 is an integer from 1 to 10,

g2 is an integer from 1 to 8,

When g1 is 2 or more, two or more G1s are the same or different from each other, and when g2 is 2 or more, two or more G2s are the same or different from each other.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, 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 an exemplary embodiment of the present specification, g1 is 10.

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

According to an exemplary 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, Formula 2 will be described in detail.

[Formula 2]

In Formula 2,

L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,

X1 is N; or CR11, and X2 is N; or CR12, and X3 is N; or CR13;

At least one of X1 to X3 is N,

R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; a 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; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; or a substituted or unsubstituted heteroarylene group.

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

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

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

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

According to an exemplary embodiment of the present specification, L may be a direct bond, or may be selected from any one of the following structural formulas.

In the above structure, the dotted line indicates the bonding position.

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

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

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 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, 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 any one of the following structural formulas.

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

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 each independently hydrogen; heavy hydrogen; a 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 each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or 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 each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 6 to C 20 aryl group; 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, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted 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 each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 6 to C 20 aryl group; 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 as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 6 to C 15 aryl group; Or 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 each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 6 to C 10 aryl group; Or 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 each independently a substituted or unsubstituted monocyclic to 6cyclic aryl group; or a substituted or unsubstituted monocyclic 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 each independently a substituted or unsubstituted monocyclic to 5cyclic aryl group; or a substituted or unsubstituted monocyclic 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 each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group; or a substituted or unsubstituted monocyclic to 4-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 each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; or a substituted or unsubstituted monocyclic to tricyclic heteroaryl 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 one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or 2 of the aforementioned substituents an aryl group unsubstituted or substituted with a group to which more than one is connected; or a heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or a group to which two or more of the aforementioned substituents are connected.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; or a heteroaryl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl 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 a cyano group, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. energy; or a heteroaryl group having 2 to 30 carbon atoms which is unsubstituted or substituted with a cyano group, 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, Ar3 and Ar4 are the same or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms energy; or a heteroaryl group having 2 to 20 carbon atoms which is unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms. energy; or a heteroaryl group having 2 to 20 carbon atoms which is unsubstituted or substituted with a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

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

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or 2 of the aforementioned substituents a phenyl group unsubstituted or substituted with a group to which more than one is connected; a biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or a group connected to two or more of the above substituents; a terphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a naphthyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a phenanthrenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a triphenylenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a fluorenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a spirobifluorenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a dibenzofuran group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; a dibenzothiophene group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected to two or more of the above-mentioned substituents; or a carbazole group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group connected with two or more of the above-mentioned substituents.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylenyl group; fluorenyl group; spirobifluorenyl group; dibenzofuran group; dibenzothiophene group; or a carbazole group, and the groups may be unsubstituted or substituted with one or more groups from the group consisting of deuterium, a halogen group, a cyano group, an alkylsilyl group, an alkyl group and an aryl 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 a phenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a biphenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a terphenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a naphthyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a phenanthrenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a triphenylenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a fluorenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a spirobifluorenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a carbazole group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; a dibenzofuran group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; or a dibenzothiophene group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl 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 a phenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a terphenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a phenanthrenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a triphenylenyl group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; spirobifluorenyl group; a carbazole group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; dibenzofuran group; or a dibenzothiophene group.

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

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

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

The structure is unsubstituted or substituted with a cyano group or an alkyl group, and the dotted line indicates a bonding position.

The structure is unsubstituted or substituted with a cyano group or a methyl group.

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 C1-C30 alkyl group or a substituted or unsubstituted C6-C30 aryl group.

In the above structure, R6 is a substituted or unsubstituted C1-C20 alkyl group or a substituted or unsubstituted C6-C20 aryl group.

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

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

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, Chemical Formula 2 is represented by any one of the following Chemical 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, definitions of L, Ar3, Ar4, and X1 to X3 are the same as in Formula 2 above.

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

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 controlled by introducing various substituents into the core structure of the above structure.

In the organic light emitting device of the present invention, a first organic material layer is formed between the first electrode and the light emitting layer using the compound of Formula 1, and a second organic material layer is formed between the second electrode and the light emitting layer using the compound of Formula 2 Except that, it may be manufactured by a conventional method and material for manufacturing an organic light emitting device.

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

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. can have a structure that However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

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

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

According to an example, the thickness of the organic material layer including the compound of Formula 2 is 30 Å to 200 Å, preferably 50 Å to 100 Å.

According to an example, the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, the hole transport layer or the hole injection layer. and the transport layer includes a compound represented by Formula 1 above.

According to an example, the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer or the hole injection layer. and the transport layer may include a compound represented by Formula 1 above.

According to an example, the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

According to an example, the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention may be an electron blocking layer, and the electron blocking layer may include the compound represented by Formula 1 above.

According to an 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 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 an 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. and the transport layer may include a compound represented by Formula 1 above.

According to an 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 an 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 a hole blocking layer, and the hole blocking layer may include the compound represented by Formula 2 above.

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

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

The organic light emitting device of the present invention may further include an organic material layer of at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. can

According to an example, the first organic material layer is in contact with the light emitting layer. Here, the contact means that another organic material layer does not exist between the light emitting layer and the first organic material layer.

According to an example, the second organic material layer is in contact with the light emitting layer. Here, the contact means that another organic material layer does not exist 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 a material known in the art may be used for the electron blocking layer.

In the exemplary 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 diode may have, for example, a stacked structure as follows, 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 a structure as shown in FIGS. 1 and 2 , but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9 are sequentially stacked . In such a structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the electron blocking layer 5 , the light emitting layer 6 or the hole blocking layer 7 .

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

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, 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 is formed thereon, and then a material that can be used as a cathode is deposited thereon can be In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material 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 multilayer structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports electrons, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc. and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

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 compound or a material known in the art may be used for the electron blocking layer.

The light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light-emitting layer emits blue light, the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the above-described compound or a material known in the art may be used for the hole blocking layer.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

In one embodiment of the present specification, the organic light emitting device may further include one or more hole blocking layers in addition to the hole blocking layer.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

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

Preparations 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,N-bis(4-bromophenyl)-[1,1'-biphenyl]-4-amine (6.74 g, 12.23 mmol), (2-(9H-) in a 500 ml round bottom flask under nitrogen atmosphere Carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (4.04g, 14.07 mmol) was completely dissolved in 240 ml of tetrahydrofuran and 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.42 g, 0.37 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 240 ml of ethyl acetate to prepare compound 1-1 (6.11 g, 70%).

MS[M+H] ⁺ = 715

Preparation Example 2: Preparation of compound 1-2

Compound 4'-bromo-N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (8.45 g, 22.06 mmol) in a 500 ml round bottom flask under nitrogen atmosphere , (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (5.06 g, 17.64 mmol) in 240 ml of tetrahydrofuran After complete dissolution, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.53 g, 0.46 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of ethyl acetate to prepare Compound 1-2 (7.16 g, 63%).

MS[M+H] ⁺ = 739

Preparation Example 3: Preparation of compound 1-3

Compound N-(3-bromophenyl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine (9.12 g, 20.31 mmol) in a 500 ml round bottom flask under nitrogen atmosphere , (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl)phenyl)boronic acid) (6.70 g, 23.36 mmol) in 240 ml of tetrahydrofuran After complete dissolution, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.70 g, 0.61 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 ml of ethyl acetate to prepare compound 1-3 (8.44 g, 63%).

MS[M+H] ⁺ = 663

Preparation Example 4: Preparation of compound 2-1

Compound A (10.87 g, 23.74 mmol), 2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl in a 500ml round bottom flask under nitrogen atmosphere -1,3,5-triazine (2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) (8.65, 20.64mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.72g, 0.62mmol) was added, and then heated for 5 hours. stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310 ml of tetrahydrofuran to prepare compound 2-1 (13.45 g, 79%).

MS[M+H] ⁺ = 716

Preparation Example 5: Preparation of compound 2-2

Compound B (12.25g, 36.75mmol), 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine ( 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine) (9.14, 23.26mmol) was completely dissolved in 280ml of tetrahydrofuran and 2M aqueous potassium carbonate solution (140 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.81 g, 0.70 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 ml of acetonitrile to prepare compound 2-2 (8.95 g, 60%).

MS[M+H] ⁺ = 690

Preparation Example 6: Preparation of compound 2-3

Compound C (11.41 g, 24.92 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid ((4- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid) (7.65g, 21.67mmol) was completely dissolved in 260ml of tetrahydrofuran, and 2M aqueous potassium carbonate solution (130ml) was added. , tetrakis- (triphenylphosphine) palladium (0.75 g, 0.65 mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 ml of tetrahydrofuran to prepare compound 2-3 (7.17 g, 52%).

MS[M+H] ⁺ = 640

Preparation Example 7: Preparation of compound 2-4

In Preparation Example 4, 2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2- ([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) instead of 2-([1,1'-biphenyl ]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1 ,3,5-triazine) was synthesized in the same manner except that it was used.

MS[M+H] ⁺ = 640

Comparative Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound [HI-1] and the following compound [HI-2] were thermally vacuum deposited to a thickness of 100 Å in a ratio of 98:2 (molar ratio) to form a hole injection layer.

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

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

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

A hole blocking layer was formed by vacuum-depositing the following compound [HB-1] to a thickness of 50 Å on the light emitting layer.

Then, on the hole blocking layer, compound [ET-1] and the following compound LiQ (Lithium Quinolate) were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to 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 material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10 ^- By maintaining ⁷ to 5×10 ^-6 torr, an organic light emitting device was manufactured.

Experimental Example 1-1 to Experimental Example 1-12

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

Comparative Examples 2 to 17

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 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 devices prepared in the Experimental Examples and Comparative Examples, the driving voltage, luminous efficiency and color coordinates were measured, and compared to the initial luminance at a current density of 10 mA/cm ² 95 The time to % (T95) was measured. The results are shown in Table 1 below. T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(electron blocking layer) compound
(hole blocking layer) Voltage
(V
@10mA
/cm ² ) efficiency
(cd/A
@10mA
/cm ² ) color coordinates
(x,y) T95
(hr) Comparative Example 1 EB-1 HB-1 5.09 5.90 (0.144, 0.045) 235 Experimental Example 1-1 1-1 2-1 3.55 6.72 (0.144, 0.046) 350 Experimental Example 1-2 1-1 2-2 3.56 6.63 (0.145, 0.047) 345 Experimental Example 1-3 1-1 2-3 3.57 6.74 (0.144, 0.046) 355 Experimental Example 1-4 1-1 2-4 3.53 6.77 (0.145, 0.046) 370 Experimental Example 1-5 1-2 2-1 3.61 6.72 (0.145, 0.047) 335 Experimental Example 1-6 1-2 2-2 3.62 6.65 (0.144, 0.046) 340 Experimental Example 1-7 1-2 2-3 3.63 6.67 (0.146, 0.045) 335 Experimental Example 1-8 1-2 2-4 3.59 6.75 (0.146, 0.046) 355 Experimental Example 1-9 1-3 2-1 3.74 6.78 (0.145, 0.045) 330 Experimental Example 1-10 1-3 2-2 3.78 6.71 (0.144, 0.046) 345 Experimental Example 1-11 1-3 2-3 3.79 6.66 (0.145, 0.047) 330 Experimental Example 1-12 1-2 2-4 3.71 6.80 (0.145, 0.046) 350 Comparative Example 2 1-1 HB-1 4.35 6.38 (0.144, 0.045) 260 Comparative Example 3 1-2 HB-1 4.31 6.37 (0.145, 0.046) 275 Comparative Example 4 1-3 HB-1 4.33 6.35 (0.145, 0.045) 240 Comparative Example 5 1-1 HB-2 4.57 6.21 (0.144, 0.046) 260 Comparative Example 6 EB-1 2-1 4.31 6.00 (0.144, 0.047) 320 Comparative Example 7 EB-1 2-2 4.32 6.06 (0.146, 0.046) 315 Comparative Example 8 EB-1 2-3 4.35 6.04 (0.145, 0.045) 325 Comparative Example 9 EB-1 2-4 4.29 6.08 (0.145, 0.046) 335 Comparative Example 10 EB-3 2-1 4.13 6.11 (0.145, 0.047) 290 Comparative Example 11 EB-3 2-2 4.14 6.17 (0.147, 0.046) 285 Comparative Example 12 EB-3 2-3 4.17 6.15 (0.146, 0.045) 295 Comparative Example 13 EB-4 2-1 4.12 6.13 (0.145, 0.046) 270 Comparative Example 14 EB-4 2-2 4.15 6.16 (0.147, 0.046) 265 Comparative Example 15 EB-4 2-3 4.18 6.14 (0.146, 0.045) 275 Comparative Example 16 EB-2 HB-1 4.76 6.07 (0.145, 0.045) 175 Comparative Example 17 EB-1 HB-2 4.78 5.43 (0.146, 0.045) 150

As shown in Table 1, in Experimental Examples 1-1 to 1-12, the compound of Formula 1 and the compound of Formula 2 of the present invention were used for the electron blocking layer and the hole blocking layer, respectively, and are represented by Formulas 1 and 2 In Comparative Examples 2 to 15, the compound of Formula 1 in Comparative Example 1 is used instead of EB-1, or the compound of Formula 2 is used instead of HB-1, which is represented by Formula 1 The organic light emitting devices of Comparative Examples 1-1 to 1-12 compared to Comparative Examples 1 to 17 basically exhibit characteristics of low voltage, high efficiency, and long lifespan. In particular, the compounds of Formula 1 have characteristics of high efficiency, and compounds of Formula 2 have characteristics of long life.

Specifically, the devices of Experimental Examples 1-1 to 1-12 exhibited a maximum increase in luminous efficiency of about 25% and a lifespan of about 150%, as compared to Comparative Examples.

Through this, when the compound of Formula 1 of the present invention is used as an electron blocking layer material and the compound of Formula 2 of the present invention is combined as a hole blocking layer, it is possible to have high efficiency characteristics while maintaining the long life characteristics of the organic light emitting device. that can be checked

Although preferred embodiments of the present invention (combination of electron blocking compound and hole blocking compound) have been described above, the present invention is not limited thereto, and various modifications are made within the scope of the claims and detailed description of the invention. It is possible to implement it and this also falls within the scope of the invention.

1: substrate
2: Anode
3: hole injection layer
4: hole transport layer
5: Electron blocking layer
6: light emitting layer
7: hole blocking layer
8: electron transport and injection layer
9: Cathode

Claims (13)

a first electrode;
a second electrode;
a light emitting layer provided between the first electrode and the second electrode;
a first organic material 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 material layer includes a compound represented by the following formula (1),
The second organic material layer is 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 an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
n is an integer of 1 to 8, and when n is 2 or more, R1 of 2 or more are the same as or different from each other,
[Formula 2]

In Formula 2,
L is a direct bond; a substituted or unsubstituted arylene group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkoxy group; a substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
X1 is N; or CR11, and X2 is N; or CR12, and X3 is N; or CR13;
At least one of X1 to X3 is N,
R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The method according to claim 1,
Wherein Chemical Formula 1 is an organic light emitting device represented by the following Chemical Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, Ar1, Ar2, R1 and n have the same definitions as in Formula 1 above. The method according to claim 1,
Formula 2 is an organic light emitting device represented by any one of 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, definitions of L, Ar3, Ar4, and X1 to X3 are the same as in Formula 2 above. The method according to claim 1,
Formula 1 is an organic light emitting device represented by any one of 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, Ar1 and Ar2 have the same definitions as in Formula 1,
G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
g1 is an integer from 1 to 10,
g2 is an integer from 1 to 8,
When g1 is 2 or more, two or more G1s are the same or different from each other, and when g2 is 2 or more, two or more G2s are the same or different from each other. The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; a terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; or a fluorenyl group unsubstituted or substituted with a methyl group. The method according to claim 1,
L is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group. The organic light emitting diode of claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

. The method according to 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 comprises a hole injection layer, a hole transport layer or a hole injection and transport layer, the hole injection layer, the hole transport layer or the hole injection and transport layer is a compound represented by the formula (1) organic light emitting device. The method according to claim 1, wherein the second organic material layer comprises an electron injection layer, an electron transport layer or an electron injection and transport layer, wherein the electron injection layer, the electron transport layer or the electron injection and transport layer comprises a compound represented by the formula (2) organic light emitting device. The method according to claim 1,
The first organic material layer may include an electron blocking layer, and the electron blocking layer will include the compound represented by Formula 1 above. The method according to claim 1,
The second organic material layer may include a hole blocking layer, and the hole blocking layer will include the compound represented by Formula 2 above. The method according to claim 1,
The organic light emitting device further comprises an organic material layer of at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. organic light emitting device.

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