KR102134523B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic light emitting device including the same.

Description

A compound and an organic light emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to a compound and an organic light emitting device including the same.

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2017-0179556, filed with the Korean Intellectual Property Office on December 26, 2017, the entire contents of which are incorporated herein.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined and paired in an organic thin film, and then extinguishes and emits light. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound that can itself constitute a light emitting layer may be used, or a compound capable of serving as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material for the organic thin film, a compound capable of performing roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

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

International Patent Application Publication No. 2003-012890

The present specification provides a compound and an organic light emitting device including the same.

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

X is S, O or NAr,

Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or Ar may combine with R2 to form a substituted or unsubstituted ring,

R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted Amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or two adjacent substituents may combine with each other to form a substituted or unsubstituted ring, or be connected by O, S or NRa And

Ra is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 6, and when m is 2 or more, R1 is the same or different from each other, n is an integer from 0 to 7, and when n is 2 or more, R2 is the same or different from each other.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.

The compounds described herein can be used as a material for the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device. In particular, the compounds described herein can be used as a material for an organic layer between electrodes.

More specifically, the compound according to an exemplary embodiment of the present invention has a structure having a high electron-accepting ability, and is excellent in heat resistance, so that it is possible to maintain an appropriate deposition temperature when manufacturing an organic light emitting device. In addition, high purity can be achieved by a sublimation purification method due to a high sublimation temperature, and no contamination is caused in a deposition apparatus or an organic light emitting device for manufacturing an organic light emitting device.

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

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

The present specification provides a compound represented by Chemical Formula 1.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure as described above. In general, it is easy to adjust the energy band gap by introducing a substituent to a core structure having a large energy band gap, but when the core structure has a small energy band gap, it is difficult to adjust the energy band gap largely by introducing a substituent. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.

In addition, by introducing various substituents to the core structure of the structure as described above, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required for each organic material layer can be synthesized. Can.

Accordingly, the present inventors have found that the compound having such a characteristic can realize a reduction in the driving voltage or a longer life when applied to a material for an organic light emitting device, especially a light emitting layer. In addition, it is easy to deposit compared to a material having a small molecular weight and a high sublimation property, and can form a stable interface with an electrode or an adjacent organic material layer.

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

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Nitrile group; Nitro group; Alkyl groups; Cycloalkyl group; Silyl group; Amine group; Aryl group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents of the above-exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 50. Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like. It is not.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups, monoheteroarylamine groups and diheteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, pyrenyl group, perylene group, chrysene group, fluorene group, but is not limited thereto.

), 디하이드로디벤조아제핀기(

)및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. In the present specification, the heterocyclic group includes one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S. have. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophene group, dibenzothiophene group , Benzofuran group, dibenzofuran group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isooxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxy group (

), dihydrodibenzoazepine group (

) And their condensation structure, but are not limited to these.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the meaning of “adjacent groups combine with each other to form a ring” among substituents means a hydrocarbon ring substituted or unsubstituted by bonding with adjacent groups; Or it means forming a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by Chemical Formula 2 below.

[Formula 2]

In Chemical Formula 2,

The definition of X, R1 and m are the same as in Formula 1,

R3 is hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The definition of R4 is the same as the definition of R2 in Chemical Formula 1,

o is an integer from 0 to 4, and when o is 2 or more, R4 is the same as or different from each other.

In one embodiment of the present specification, R3 is hydrogen, a nitrile group, a methyl group, an ethyl group, a propyl group, or a butyl group.

In one embodiment of the present specification, R3 is hydrogen, a nitrile group, a methyl group, or a tert-butyl group.

In one embodiment of the present specification, when the position of R3 is the same as in Chemical Formula 2, the process of preparing the compound is simplified and is easy in the process.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 6.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6,

The definition of X, R1 and m are the same as in Formula 1,

R5 to R7 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted An amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

p is an integer from 0 to 3, and when p is 2 or more, R5 is the same as or different from each other,

q is an integer from 0 to 6, and when q is 2 or more, R6 is the same as or different from each other,

r is an integer from 0 to 8, and when r is 2 or more, R7 is the same as or different from each other.

In one embodiment of the present specification, R5 is as defined for R3 in Chemical Formula 2.

In one embodiment of the present specification, R6 is hydrogen.

In one embodiment of the present specification, R7 is hydrogen or a phenyl group.

In one embodiment of the present specification, r is 2.

In one embodiment of the present specification, Chemical Formula 6 is represented by the following Chemical Formula 6-1.

[Formula 6-1]

In Formula 6-1, the definitions of X, R1, R5, m and p are as in Formula 6.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 7 to 18.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

In the above formulas 7 to 18,

The definition of X, R2, and n is the same as in Formula 1,

Y is CRR', NR", O, or S,

R, R', R" and R10 to R15 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

a and b are integers from 0 to 4,

c is an integer from 0 to 6,

d is an integer from 0 to 8,

e is an integer from 0 to 3,

f is an integer from 0 to 5,

When a to f are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, R10 to R15 are the same as or different from each other, and each independently hydrogen or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R10 to R15 are the same as or different from each other, and each independently hydrogen or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R10 to R12, R14 and R15 are hydrogen.

In one embodiment of the present specification, in Chemical Formula 11, R13 is hydrogen or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, in Chemical Formula 11, R13 is hydrogen or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, in Formula 11, R13 is hydrogen or a phenyl group.

In one embodiment of the present specification, Chemical Formula 11 is represented by Chemical Formula 11-1 below.

[Formula 11-1]

In Formula 11-1, the definitions of X, R2 and n are the same as in Formula 1.

In one embodiment of the present specification, Y is O.

In one embodiment of the present specification, Y is S.

In one embodiment of the present specification, Y is CRR', and R and R'are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group.

In one embodiment of the present specification, Y is CRR', and R and R'are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, Y is CRR', and R and R'are the same or different from each other, and each independently an substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

In one embodiment of the present specification, Y is CRR', and R and R'are methyl groups.

In one embodiment of the present specification, Y is NR" and R" is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Y is NR" and R" is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y is NR" and R" is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, X is O.

In one embodiment of the present specification, X is S.

In one embodiment of the present specification, X is NAr, and Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 36 carbon atoms, and Ar is It may combine with adjacent groups to form a substituted or unsubstituted ring. The group adjacent to Ar is R2 in Formula 1, R4 in Formula 2, R5 or R6 in Formulas 3 to 5, R5 or R7 in Formulas 6, and R2 in Formulas 7 to 18.

In one embodiment of the present specification, Ar is a phenyl group unsubstituted or substituted with an alkyl group; Or a naphthyl group, and may combine with an adjacent group to form a ring substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, Ar is a phenyl group unsubstituted or substituted with a methyl group; Or a naphthyl group, and may combine with an adjacent group to form a ring substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 20 below.

[Formula 20]

In Chemical Formula 20, R1, and m are as defined in Chemical Formula 1,

R21 and R22 are the same as the definition of R2 in Chemical Formula 1,

n1 is an integer from 0 to 3, n2 is an integer from 0 to 7,

When n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or It is an unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or It is an unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, ethyl group, propyl group, butyl group, diphenylamine group unsubstituted or substituted with an alkyl group, Dihydrodibenzoazepine group, phenoxazine group, phenyl group unsubstituted or substituted with nitrile group, naphthyl group, trimethylsilyl group, carbazole group, or fluorenyl group unsubstituted or substituted with alkyl group, or two adjacent substituents are bonded to each other To form a substituted or unsubstituted ring, or may be linked by O, S or NRa, wherein Ra is a phenyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, tert-butyl group, methyl group; Ethyl group; Propyl group; Or a substituted or unsubstituted diphenylamine group substituted with a butyl group, a dihydrodibenzoazepine group, a phenoxazine group, a phenyl group substituted with a nitrile group, a naphthyl group, a trimethylsilyl group, a carbazole group, or a methyl group It may be a fluorenyl group, or two adjacent substituents may combine with each other to form a substituted or unsubstituted ring, or may be connected by O, S or NRa, and Ra is a phenyl group.

In one embodiment of the present specification, when R1 and R2 are connected by O, S or NRa, Formula 1 may be represented by any one of the following Formulas 21 to 23.

[Formula 21]

[Formula 22]

[Formula 23]

In Chemical Formulas 21 to 23, X and Ra are the same as those in Chemical Formula 1,

R23 and R24 are as defined for R1 and R2 in Formula 1,

n3 is an integer from 0 to 6, n4 is an integer from 0 to 5,

When n3 and n4 are 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R23 and R24 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or It is an unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R23 and R24 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, ethyl group, propyl group, butyl group, diphenylamine group unsubstituted or substituted with an alkyl group, Dihydrodibenzoazepine group, phenoxazine group, phenyl group unsubstituted or substituted with nitrile group, naphthyl group, trimethylsilyl group, carbazole group, or fluorenyl group unsubstituted or substituted with alkyl group, or two adjacent substituents are bonded to each other To form a substituted or unsubstituted ring.

In one embodiment of the present specification, R23 and R24 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, ethyl group, propyl group, tert-butyl group, methyl group; Ethyl group; Propyl group; Or a substituted or unsubstituted diphenylamine group, dihydrodibenzoazepine group, phenoxazine group, nitrile group-substituted phenyl group, naphthyl group, trimethylsilyl group, carbazole group, or methyl group The fluorenyl group or two adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, when the R1 and R2 are connected by O, S or NRa, Formula 1 may be represented by any one of the following Formulas 21-1, 22-2 and 23-1.

[Formula 21-1]

[Formula 22-1]

[Formula 23-1]

In Chemical Formulas 21-1, 22-1 and 23-1,

R21, R22, and R24 are as defined for R1 and R2 in Formula 1,

n1 is an integer from 0 to 3, n2 and n4 are integers from 0 to 5,

When n1, n2 and n4 are 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R21, R22, and R24 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, It is a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R21, R22, and R24 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, ethyl group, propyl group, butyl group, diphenylamine unsubstituted or substituted with an alkyl group A phenyl group unsubstituted or substituted with a group, a dihydrodibenzoazepine group, a phenoxazine group, or a nitrile group, a fluorenyl group unsubstituted or substituted with a naphthyl group, a trimethylsilyl group, a carbazole group, or an alkyl group, or two adjacent substituent groups They combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R21, R22, and R24 are the same as or different from each other, and each independently hydrogen, nitrile group, methyl group, ethyl group, propyl group, tert-butyl group, methyl group; Ethyl group; Propyl group; Or a substituted or unsubstituted diphenylamine group, dihydrodibenzoazepine group, phenoxazine group, nitrile group-substituted phenyl group, naphthyl group, trimethylsilyl group, carbazole group, or methyl group The fluorenyl group or two adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is selected from the following structural formulas.

In addition, the present specification provides an organic light emitting device comprising the above-described compound.

In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

When a member is referred to as being “on” another member in the present specification, this includes not only the case where one member is in contact with the other member but also another member between the two members.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless specifically stated otherwise.

The organic material layer of the organic light emitting device of the present application 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, as a typical example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer is a blue light emitting layer.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer is a green light emitting layer.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound as a dopant.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound and a host compound.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound and the host compound in a weight ratio of 1: 1 to 1: 99.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound and the host compound in a weight ratio of 1: 1 to 1: 50.

In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound and two different host compounds.

As described above, when two different types of hosts are used as the host of the light emitting layer, the life and efficiency of the device are improved.

In one embodiment of the present application, any one of the two different host compounds is an auxiliary dopant or sensitizer.

At this time, the auxiliary dopant (assistant dopant), or a compound acting as a sensitizer (sensitizer) receives holes and electrons from the host to form excitons, and the generated excitons are fluorescent dopants It will serve as a delivery.

In a typical organic light emitting device, the number of excitons generated in singlet and triplet is generated at a ratio of 25:75 (single term: triplet), and fluorescent emission, phosphorescence emission, and thermal activation delayed fluorescence depending on the light emission type according to exciton movement It can be divided into luminescence. In the case of the phosphorescence emission, it means that the exciton of the triplet excited state moves to the ground state and emits light, and in the case of the fluorescent emission, the exciton of the singlet excited state is the ground state ( It means that it moves to the ground state and emits light, and the thermally activated delayed fluorescence emission reverses the transition from the triplet excited state to the singlet excited state, and the singlet excited state. It means that the exciton moves to the ground state and causes fluorescence emission.

According to the exemplary embodiment of the present specification, the triplet energy level of the compound serving as the auxiliary dopant or the sensitizer is 2.1 eV or more, and preferably 2.1 eV or more and 3.0 eV Hereinafter, it may be 2.2 eV or more and 3.0 eV or less, 2.4 eV or more and 2.9 eV or less. When the triplet energy level of the compound represented by Chemical Formula 1 satisfies the above range, electron injection is facilitated and the exciton formation rate is increased, so that the luminous efficiency is increased.

According to an exemplary embodiment of the present specification, the difference between the singlet energy level and the triplet energy level of the compound serving as the auxiliary dopant, or sensitizer is 0 eV or more 0.3 eV or less, preferably 0 eV or more and 0.2 eV or less. When the difference between the singlet energy level and the triplet energy level of the compound serving as the auxiliary dopant or sensitizer satisfies the above range, the exciton generated in the triplet The rate and speed of movement to the singlet increases due to the reverse interphase transition (RISC), so that the time for the exciton to stay in the triplet decreases, thereby increasing the efficiency and lifetime of the organic light emitting device.

In the present specification, triplet energy can be measured using a spectral instrument capable of measuring fluorescence and phosphorescence, and in the case of measurement conditions, in a cryogenic state using liquefied nitrogen, toluene or thiF is used as a solvent to a concentration of 10 ^-6 M Prepare a solution and irradiate a light source of an absorption wavelength band of a substance to the solution, except for the singlet emission from the emitted spectrum, and analyze the spectrum emitted from the triplet to confirm. When the electrons from the light source reverse, the time for the electrons to stay in the triplet is much longer than the time in the singlet, so it is possible to separate the two components in the cryogenic state.

In the present specification, the singlet energy is measured using a fluorescent device, and the light source is irradiated at room temperature, unlike the triplet energy measurement method described above.

In one embodiment of the present specification, a compound that is not an auxiliary dopant among the host compounds may be selected from the following structural formula, but is not limited thereto.

In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.

In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound.

In one embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound.

In one embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or the electron injection and transport layer includes the compound.

In one embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer contains the compound.

In one embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. It includes two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers contains the compound.

In an exemplary embodiment of the present application, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.

In one embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers contains the compound. Specifically, in one embodiment of the present specification, the compound may be included in one layer of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.

In addition, in one embodiment of the present application, when the compound is included in each of the two or more electron transport layers, other materials except the compound may be the same or different from each other.

In one embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

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

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 3.

2 is an organic light emitting device in which the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, the electron transport layer 7 and the cathode 4 are sequentially stacked. The structure is illustrated. In such a structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

3 shows the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 8, the light emitting layer 3, the electron injection and transport layer 9 and the cathode 4 An example of an organic light emitting device sequentially stacked is illustrated. In this structure, the compound may be included in the light emitting layer 3, but is not limited thereto.

In such a structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

The organic light emitting device of the present application may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.

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

For example, the organic light emitting device of the present application can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And, after forming a hole injection layer, a hole transport layer, an organic material layer including a light emitting layer and an electron transport layer, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to such a method, an organic light emitting device may be made by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode 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 metal and oxide 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 material is preferably a material having a small work function to facilitate electron injection into an organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is 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 porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole is transported to the light emitting layer by transporting holes from the anode or the hole injection layer, and the mobility of holes is large. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include compounds, dibenzofuran derivatives, and ladder-type furan compounds. , Pyrimidine derivatives, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, 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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that prevents the cathode from reaching the hole, 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 are not limited thereto.

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

The preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited by them.

<Production Example>

The method for preparing the material of the present invention started from synthesis of an intermediate in which halide was introduced using substituted or unsubstituted aniline as follows. Asymmetrically, an amine or carbazole was introduced to one halide through an amination, and an aryl group was introduced to the other halide through a Suzuki reaction, and then the amino group (-NH ₂ ) was replaced with bromide (-Br) through a Sandmeyer reaction. . Thereafter, boron was finally introduced using butyllithium and tribromoborane. Compounds of the specific examples were synthesized through the following reaction using aniline introduced with various substituents in addition to the aniline types shown in Preparation Example 1-1.

Manufacturing example 1-1: Synthesis of Compound 1-A

[Scheme 1-1]

The compound 2-iodoaniline (30 g, 0.14 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, and then bromine (21.9 g, 0.14 mol) was added at 0°C and stirred for 2 hours. After extracting the organic layer with 300 mL of 1 mL sodium cysulfate solution, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 1-A (38.8 g, yield: 95%).

MS[M+H] ⁺ = 297

Manufacturing example 1-2: Synthesis of Compound 1-B

[Scheme 1-2]

The compound 2-iodo-4-methyl-aniline (32.6 g, 0.14 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, and then bromine (21.9 g, 0.14 mol) was added at 0°C and stirred for 2 hours. After extracting the organic layer with 300 mL of 1 mL of sodium cysulfate solution, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 1-B (40.2 g, yield: 92%).

MS[M+H] ⁺ = 311

Manufacturing example 1-3: Synthesis of Compound 1-C

[Scheme 1-3]

The compound 2-iodo-4-methyl(D ₃ )aniline (33 g, 0.14 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, and then bromine (21.9 g, 0.14 mol) was added at 0° C. and stirred for 2 hours. Did. After extracting the organic layer with 300 mL of 1 mL sodium sodium sulfate solution, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 1-C (41.9 g, yield: 95%).

MS[M+H] ⁺ = 314

Manufacturing example 1-4: Synthesis of Compound 1-D

[Scheme 1-4]

The compound 2-iodo-4-chloroaniline (35.5 g, 0.14 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, and then bromine (21.9 g, 0.14 mol) was added at 0° C. and stirred for 2 hours. After extracting the organic layer with 300 mL of 1 mL of sodium cysulfate solution, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 1-D (43.7 g, yield: 94%).

MS[M+H] ⁺ = 332

In addition to the above compounds, various kinds of intermediates included in the specific examples were synthesized through the bromination reaction of 2-iodoaniline in which a substituent corresponding to the substance of the present invention was introduced.

Manufacturing example 2-1: Synthesis of Compound 2-A

[Scheme 2-1]

Di(naphthalen-2-yl)amine (32.3 g, 0.12 mol) was completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium terbutoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphine palladium (5.5 g) , 4.8 mmol) and refluxed for 1 hour and stirred. During the reflux, compound 1-A (35.7 g, 0.12 mol) was dissolved in 120 mL of toluene and slowly dropped to stir and refluxed for 2 hours to stir. After the reaction was completed, the organic layer was extracted with water, and the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 2-A (43.2 g, yield: 82%).

MS[M+H] ⁺ = 439

Manufacturing example 2-2: Synthesis of Compound 2-B

[Scheme 2-2]

Di(naphthalen-2-yl)amine (32.3 g, 0.12 mol) was completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium terbutoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphine palladium (5.5 g) , 4.8 mmol) and refluxed for 1 hour and stirred. During the reflux, compound 1-B (37.4 g, 0.12 mol) was dissolved in 120 mL of toluene and slowly dropped to stir and refluxed for 2 hours to stir. After the reaction was completed, the organic layer was extracted with water, and then the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 2-B (43.5 g, yield: 80%).

MS[M+H] ⁺ = 453

Manufacturing example 2-3: Synthesis of Compound 2-C

[Scheme 2-3]

Di(naphthalen-2-yl)amine (32.3 g, 0.12 mol) was completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium terbutoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphine palladium (5.5 g) , 4.8 mmol) and refluxed for 1 hour and stirred. During the reflux, compound 1-C (37.8 g, 0.12 mol) was dissolved in 120 mL of toluene and slowly dropped to stir and refluxed for 2 hours to stir. After the reaction was completed, the organic layer was extracted with water, and the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 2-C (45.4 g, yield: 83%).

MS[M+H] ⁺ = 456

Manufacturing example 2-4: Synthesis of Compound 2-D

[Scheme 2-4]

Di(naphthalen-2-yl)amine (32.3 g, 0.12 mol) was completely dissolved in 240 mL of toluene in a nitrogen atmosphere, followed by sodium terbutoxide (23.1 g, 0.24 mol), tetrakistriphenylphosphine palladium (5.5 g) , 4.8 mmol) and refluxed for 1 hour and stirred. During the reflux, compound 1-D (39.9 g, 0.12 mol) was dissolved in 120 mL of toluene, and then slowly dropped and stirred by refluxing for 2 hours. After the reaction was completed, the organic layer was extracted with water, and then the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 2-D (46.1 g, yield: 81%).

MS[M+H] ⁺ = 473

In addition to the above compound, an amine in which a substituent corresponding to the substance of the present invention is introduced is reacted with the compound of Preparation Examples 1-1 to 1-4 (aniline corresponding to the specific example of the present invention produced through a bromination reaction) Through the synthesis of various types of intermediates included in the specific examples. Some of the intermediates synthesized in the same manner as the above reaction are as follows.

Manufacturing example 3-1: Synthesis of Compound 3-A

[Scheme 3-1]

After completely dissolving the compound 2-A (39.5 g, 0.09 mol) in 300 mL of tetrahydrofuran in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10M) was added and 1-naphthylboronic acid (17.2 g, 0.10 mol) was added. Did. Tetrakistriphenylphosphine palladium (2.1g, 1.8mmol) was added and refluxed for 3 hours and stirred. After the reaction was completed, after removing the water layer, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 3-A (39.4 g, yield: 90%).

MS[M+H] ⁺ = 487

Manufacturing example 3-2: Synthesis of Compound 3-B

[Scheme 3-2]

After completely dissolving the compound 2-B (40.8 g, 0.09 mol) in 300 mL of tetrahydrofuran in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10M) was added and 1-naphthylboronic acid (17.2 g, 0.10 mol) was added. Did. Tetrakistriphenylphosphine palladium (2.1 g, 1.8 mmol) was added and stirred by refluxing for 3 hours. After the reaction was completed, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 3-B (41.4 g, yield: 92%).

MS[M+H] ⁺ = 501

Manufacturing example 3-3: Synthesis of Compound 3-C

[Scheme 3-3]

After completely dissolving the compound 2-C (41.1 g, 0.09 mol) in 300 mL of tetrahydrofuran in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10M) was added, and 1-naphthylboronic acid (17.2 g, 0.10 mol) was added. Did. Tetrakistriphenylphosphine palladium (2.1 g, 1.8 mmol) was added and stirred by refluxing for 3 hours. After the reaction was completed, after removing the water layer, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 3-C (40.8 g, yield: 90%).

MS[M+H] ⁺ = 504

Manufacturing example 3-4: Synthesis of Compound 3-D

[Scheme 3-4]

After completely dissolving the compound 2-D (42.6 g, 0.09 mol) in 300 mL of tetrahydrofuran in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10 M) was added, and 1-naphthylboronic acid (17.2 g, 0.10 mol) was added. Did. Tetrakistriphenylphosphine palladium (2.1g, 1.8mmol) was added and refluxed for 3 hours and stirred. After the reaction was completed, after removing the water layer, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 3-D (42.7 g, yield: 91%).

MS[M+H] ⁺ = 521

In addition to the above compounds, aryl boronic acid in which substituents corresponding to the substances of the present invention are introduced are included in specific examples through the Suzuki reaction with the compounds of Preparation Examples 1-1 to 1-4 and Preparation Examples 2-1 to 2-3. Various types of intermediates were synthesized. Some of the intermediates synthesized in the same manner as the above reaction are as follows.

Manufacturing example 4-1: Synthesis of Compound 4-A

[Scheme 4-1]

In a nitrogen atmosphere, 0.7 L of acetonitrile was added to the compound 3-A (34.1 g, 0.07 mol), and 15 mL of 12M hydrochloric acid was added at 0°C. Sodium nitrite (6.9 g, 0.10 mol) was added at 0° C., then stirred for 10 minutes, and copper bromide (II) (22.3 g, 0.10 mol) was added and heated to 50° C. After heating for 1 hour, it was back-precipitated in 1.5 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform/hexane) to prepare compound 4-A (28.9 g, yield: 75%).

MS[M+H] ⁺ = 550

Manufacturing example 4-2: Synthesis of Compound 4-B

[Scheme 4-2]

In a nitrogen atmosphere, 0.7 L of acetonitrile was added to the compound 3-B (35 g, 0.07 mol), and 15 mL of 12M hydrochloric acid was added at 0°C. Sodium nitrite (6.9 g, 0.10 mol) was added at 0° C., then stirred for 10 minutes, and copper bromide (II) (22.3 g, 0.10 mol) was added and heated to 50° C. After heating for 1 hour, it was back-precipitated in 1.5 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform/hexane) to prepare compound 4-B (30.4 g, yield: 77%).

MS[M+H] ⁺ = 564

Manufacturing example 4-3: Synthesis of Compound 4-C

[Scheme 4-3]

In a nitrogen atmosphere, 0.7 L of acetonitrile was added to the compound 3-C (35.2 g, 0.07 mol), and 15 mL of 12M hydrochloric acid was added at 0°C. Sodium nitrite (6.9 g, 0.10 mol) was added at 0° C., then stirred for 10 minutes, and copper bromide (II) (22.3 g, 0.10 mol) was added and heated to 50° C. After heating for 1 hour, it was back-precipitated in 1.5 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform/hexane) to prepare compound 4-C (30.2 g, yield: 76%).

MS[M+H] ⁺ = 567

Manufacturing example 4-4: Synthesis of Compound 4-D

[Scheme 4-4]

In a nitrogen atmosphere, 0.7 L of acetonitrile was added to the compound 3-D (36.5 g, 0.07 mol), and 15 mL of 12M hydrochloric acid was added at 0°C. Sodium nitrite (6.9 g, 0.10 mol) was added at 0° C., then stirred for 10 minutes, and copper bromide (II) (22.3 g, 0.10 mol) was added and heated to 50° C. After heating for 1 hour, it was back-precipitated in 1.5 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform/hexane) to prepare compound 4-D (30.7 g, yield: 75%).

MS[M+H] ⁺ = 584

Manufacturing example 5-1: Synthesis of Compound 1

[Scheme 5-1]

In a nitrogen atmosphere, 200 ml of toluene was added to the compound 4-A (27.5 g, 0.05 mol) and 20 mL of 2.5M n-butyllithium was added at -78°C. After stirring at -78°C for 2 hours, tribromoborane (25.0g, 0.1mol) was added at -78°C and stirred for 30 minutes. After raising the temperature to room temperature and stirring for 30 minutes, the mixture is stirred at 50°C for 1 hour. After cooling to 0° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform/hexane) to obtain Compound 1 (15.1 g, yield: 63%). It was prepared.

MS[M+H] ⁺ = 480

Manufacturing example 5-2: Synthesis of Compound 15

[Scheme 5-2]

In nitrogen atmosphere, 200 ml of toluene was added to the compound 4-B (28.2 g, 0.05 mol) and 20 mL of 2.5M n-butyllithium was added at -78°C. After stirring at -78°C for 2 hours, tribromoborane (25.0g, 0.1mol) was added at -78°C and stirred for 30 minutes. After raising the temperature to room temperature and stirring for 30 minutes, the mixture is stirred at 50°C for 1 hour. After cooling to 0° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform/hexane) to obtain the compound 15 (16.0 g, yield: 65%). It was prepared.

MS[M+H] ⁺ = 494

Manufacturing example 5-3: Synthesis of Compound 82

[Scheme 5-3]

200 ml of toluene was added to the starting compound (29 g, 0.05 mol) synthesized by the above synthesis method in a nitrogen atmosphere, and 20 mL of 2.5M n-butyllithium was added at -78°C. After stirring at -78°C for 2 hours, tribromoborane (25.0g, 0.1mol) was added at -78°C and stirred for 30 minutes. After raising the temperature to room temperature and stirring for 30 minutes, the mixture is stirred at 50°C for 1 hour. After cooling to 0° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform/hexane) to give the compound 82 (18.1 g, yield: 62%). It was prepared.

MS[M+H] ⁺ = 583

Manufacturing example 5-4: Synthesis of Compound 5-D

[Scheme 5-4]

In a nitrogen atmosphere, 200 ml of toluene was added to the compound 4-D (29.2 g, 0.05 mol) and 20 mL of 2.5M n-butyllithium was added at -78°C. After stirring at -78°C for 2 hours, tribromoborane (25.0g, 0.1mol) was added at -78°C and stirred for 30 minutes. After raising the temperature to room temperature and stirring for 30 minutes, the mixture is stirred at 50°C for 1 hour. After cooling to 0° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. Diisopropylethylamine (6.5 g, 0.05 ml) was further added at room temperature, and then the solvent was completely distilled and purified by column chromatography (chloroform/hexane) to give the compound 5-D (17.0 g, yield: 66%). ) Was prepared.

MS[M+H] ⁺ = 514

30 ml of toluene was added to the starting material compound (5.3 g, 0.01 mol) synthesized through the above synthesis process in a nitrogen atmosphere, and diphenylamine (1.7 g, 0.01 mol) and sodium terbutoxide (1.9 g, 0.02 mol) were added. Did. Tetrakistriphenylphosphine palladium (58mg, 0.05mmol) was added and refluxed and stirred for 2 hours. After extracting the organic layer with water, the solvent was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 83 (6.1 g, yield: 93%).

MS[M+H] ⁺ = 659

Manufacturing example 6-2: Synthesis of Compound 6-D

[Scheme 6-2]

140 ml of 1,4-dioxane was added to the starting compound (20.6 g, 0.04 mol) synthesized through the above synthesis process in a nitrogen atmosphere, and potassium acetate (7.9 g, 0.08 mol) and bis-pinacolactodiboron (10.2 g, 0.04 mol). Further, palladium acetate (90mg, 0.4mmol) was added and refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with water, and then the solvent was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 6-D (22.5 g, yield: 93%).

MS[M+H] ⁺ = 606

Manufacturing example 6-3: Synthesis of Compound 70

[Scheme 6-3]

After completely dissolving in 30 mL of tetrahydrofuran in compound 6-D (18.2 g, 0.03 mol) in nitrogen atmosphere, 10 mL of potassium carbonate aqueous solution (10M) was added and bromobenzene (4.8 g, 0.03 mol) was added. Tetrakistriphenylphosphine palladium (0.35 g, 0.3 mmol) was added and stirred by refluxing for 3 hours. After the reaction was completed, after removing the water layer, the organic layer was completely distilled and purified by column chromatography (chloroform/hexane) to prepare the compound 70 (15.8 g, yield: 95%).

MS[M+H] ⁺ = 556

In addition to the above compounds, compounds of Examples 1 to 45 and 47 to 96 were synthesized through the same process as the above reaction using a compound in which a substituent corresponding to the substance of the present invention was introduced.

< Example >

In this example, an organic photoluminescent device was manufactured by including the compound of Formula 1 according to an exemplary embodiment of the present specification in a light emitting layer, and characteristics were evaluated.

In this experimental example, the host material (m-CBP) having a triplet value of 2.5 eV or more, and E _{ST (} difference between singlet energy and triplet energy) with a compound of Formula 1 according to an exemplary embodiment of the present specification is 0.2 A green organic photoluminescence device was manufactured by including a Sensitizer (4CzIPN) having a TADF (delayed fluorescence) property of less than eV in a light emitting layer, and characteristics were evaluated.

<Comparative Example 1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator. On the prepared ITO transparent electrode, each thin film was laminated with a vacuum degree of 5.0 Х 10-4 으로 by vacuum deposition. First, on ITO, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum-deposited to a thickness of 500 Pa to form a hole injection layer.

A hole transport layer is formed by vacuum-depositing the following compound 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300 kPa), which is a material for transporting holes on the hole injection layer. Did.

The following compound N-([1,1'-bisphenyl]-4-yl)-N-(4-(11-([1,1'-biphenyl]-4-yl) having a film thickness of 100 mm 2 on the hole transport layer )-11H-benzo[a]carbazole-5-yl)phenyl)-[1,1'-biphenyl]-4-amine (EB1) (100 kPa) was vacuum deposited to form an electron blocking layer.

Subsequently, a light emitting layer was formed by vacuum-depositing m-CBP, 4CzIPN, and GD1 as shown below at a weight ratio of 68:30:2 with a film thickness of 300 mm 2 over the electron blocking layer.

A compound ET1 and a compound LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 on the light emitting layer to form an electron injection and transport layer with a thickness of 300 MPa. On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 2,000 순차적 were sequentially deposited to form a negative electrode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- An} organic light emitting device was manufactured by maintaining ⁷ to 5 x 10 ^-6 torr.

Experimental Example 1-1 to 1-81

An organic light emitting diode was manufactured according to the same method as Comparative Example 1-1 except for using the compound of Table 1 below instead of the compound GD1 in Experimental Example 1.

Comparative example 1-2

An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound of GD2 below was used instead of compound GD1 in Comparative Example 1-1.

When current was applied to the organic light emitting devices manufactured by Experimental Examples 1-1 to 1-81 and Comparative Examples 1-1 and 1-2, the results of measuring voltage, efficiency, and emission wavelength are shown in Table 1 below. .

division compound
(Light emitting layer) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Luminous wavelength
(nm) Comparative Example 1-1 Compound GD1 4.86 4.73 524 Experimental Example 1-1 Compound 1 3.85 18.6 535 Experimental Example 1-2 Compound 2 3.92 18.7 531 Experimental Example 1-3 Compound 3 3.91 18.3 537 Experimental Example 1-4 Compound 4 3.89 18.5 532 Experimental Example 1-5 Compound 5 3.91 18.3 530 Experimental Example 1-6 Compound 6 3.91 18.8 533 Experimental Example 1-7 Compound 7 3.96 18.1 537 Experimental Example 1-8 Compound 8 3.89 18.5 540 Experimental Example 1-9 Compound 9 3.88 18.6 538 Experimental Example 1-10 Compound 10 3.90 18.9 537 Experimental Example 1-11 Compound 11 3.87 18.8 539 Experimental Example 1-12 Compound 12 3.90 18.7 535 Experimental Example 1-13 Compound 13 3.88 18.3 536 Experimental Example 1-14 Compound 14 3.90 18.7 533 Experimental Example 1-15 Compound 15 3.92 18.8 531 Experimental Example 1-16 Compound 16 3.91 18.1 534 Experimental Example 1-17 Compound 17 3.93 18.1 533 Experimental Example 1-18 Compound 18 3.94 18.5 537 Experimental Example 1-19 Compound 19 3.90 18.7 538 Experimental Example 1-20 Compound 20 3.91 18.3 539 Experimental Example 1-21 Compound 21 3.91 18.7 540 Experimental Example 1-22 Compound 22 3.94 18.2 538 Experimental Example 1-23 Compound 23 3.96 18.1 537 Experimental Example 1-24 Compound 24 3.97 18.0 537 Experimental Example 1-25 Compound 25 3.97 18.4 538 Experimental Example 1-26 Compound 26 3.88 18.1 535 Experimental Example 1-27 Compound 27 3.88 18.4 539 Experimental Example 1-28 Compound 28 3.89 18.3 532 Experimental Example 1-29 Compound 29 3.89 18.1 534 Experimental Example 1-30 Compound 30 3.87 18.2 535 Experimental Example 1-31 Compound 31 3.88 18.1 532 Experimental Example 1-32 Compound 32 3.85 18.5 536 Experimental Example 1-33 Compound 33 3.84 18.4 547 Experimental Example 1-34 Compound 34 3.85 18.3 542 Experimental Example 1-35 Compound 35 3.91 18.3 545 Experimental Example 1-36 Compound 36 3.92 18.1 544 Experimental Example 1-37 Compound 37 3.93 18.1 544 Experimental Example 1-38 Compound 38 3.94 18.2 528 Experimental Example 1-39 Compound 39 3.91 18.1 527 Experimental Example 1-40 Compound 40 3.92 18.2 526 Experimental Example 1-41 Compound 41 3.90 18.5 520 Experimental Example 1-42 Compound 42 3.88 18.6 529 Experimental Example 1-43 Compound 50 3.91 18.0 532 Experimental Example 1-44 Compound 51 3.92 18.4 534 Experimental Example 1-45 Compound 52 3.94 18.3 537 Experimental Example 1-46 Compound 53 3.91 18.1 540 Experimental Example 1-47 Compound 54 3.88 18.2 540 Experimental Example 1-48 Compound 55 3.89 18.6 537 Experimental Example 1-49 Compound 56 3.90 18.7 538 Experimental Example 1-50 Compound 57 3.91 18.7 538 Experimental Example 1-51 Compound 58 3.91 18.3 536 Experimental Example 1-52 Compound 59 3.92 18.2 535 Experimental Example 1-53 Compound 60 3.94 18.1 531 Experimental Example 1-54 Compound 61 3.90 18.1 533 Experimental Example 1-55 Compound 62 3.89 18.4 539 Experimental Example 1-56 Compound 63 3.89 18.4 538 Experimental Example 1-57 Compound 64 3.88 18.6 539 Experimental Example 1-58 Compound 65 3.88 18.1 540 Experimental Example 1-59 Compound 66 3.90 18.2 531 Experimental Example 1-60 Compound 67 3.91 18.1 532 Experimental Example 1-61 Compound 68 3.92 18.1 538 Experimental Example 1-62 Compound 69 3.91 18.3 539 Experimental Example 1-63 Compound 70 3.89 18.4 540 Experimental Example 1-64 Compound 71 3.88 18.7 538 Experimental Example 1-65 Compound 72 3.91 18.6 542 Experimental Example 1-66 Compound 73 3.92 18.5 533 Experimental Example 1-67 Compound 74 3.89 18.5 535 Experimental Example 1-68 Compound 75 3.92 18.0 538 Experimental Example 1-69 Compound 76 3.90 18.1 537 Experimental Example 1-70 Compound 77 3.88 18.2 531 Experimental Example 1-71 Compound 78 3.91 18.3 538 Experimental Example 1-72 Compound 79 3.94 18.1 537 Experimental Example 1-73 Compound 80 3.92 18.1 536 Experimental Example 1-74 Compound 81 3.89 18.3 538 Experimental Example 1-75 Compound 82 3.89 18.4 539 Experimental Example 1-76 Compound 83 3.90 18.6 540 Experimental Example 1-77 Compound 84 3.92 18.4 535 Experimental Example 1-78 Compound 85 3.91 18.1 534 Experimental Example 1-79 Compound 86 3.90 18.1 538 Experimental Example 1-80 Compound 87 3.91 18.3 537 Experimental Example 1-81 Compound 88 3.90 18.0 535 Comparative Example 1-2 Compound GD2 4.41 13.5 501

As shown in Table 1, all of the devices of Experimental Examples 1-1 to 1-81 using a compound having the structure of Formula 1 as a core have a lower voltage and a higher efficiency than devices using the compound GD1 in Comparative Example 1-1. I got this ascending result.

In addition, when comparing with the device of Comparative Example 1-2, it was found that the structure of Formula 1 in an asymmetrical form improved both in terms of voltage and efficiency.

As shown in the results of Table 1, it was confirmed that the compound according to the present invention has excellent luminescence ability and is capable of tuning the emission wavelength, thereby realizing an organic light emitting device having high color purity.

<Experimental Example 2>

In this experimental example, a blue organic photoluminescence device was manufactured by including a host material (BH) in a light emitting layer together with Formula 1 according to an exemplary embodiment of the present specification, and properties were evaluated.

<Comparative Example 2-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator. On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum-deposited to a thickness of 500 Pa to form a hole injection layer.

A hole transport layer is formed by vacuum-depositing the following compound 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300 kPa), which is a material for transporting holes on the hole injection layer. Did.

The following compound N-([1,1'-bisphenyl]-4-yl)-N-(4-(11-([1,1'-biphenyl]-4-yl) having a film thickness of 100 mm 2 on the hole transport layer )-11H-benzo[a]carbazole-5-yl)phenyl)-[1,1'-biphenyl]-4-amine (EB1) (100 kPa) was vacuum deposited to form an electron blocking layer.

Subsequently, a light emitting layer was formed by vacuum-depositing the following BH and BD at a weight ratio of 25:1 with a film thickness of 300 MPa on the electron blocking layer.

On the light emitting layer, the compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300 Pa. On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 2,000 순차적 were sequentially deposited to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å/sec and aluminum at 2 Å/sec, and the vacuum degree during deposition was 2 진공10 ^-7. Maintaining ~ 5 ⅹ10 ^-6 torr, an organic light emitting device was manufactured.

< Experimental Example 2-1 to 2-15>

An organic light-emitting device was manufactured in the same manner as in Comparative Example 2-1, except that the compound of Table 2 below was used instead of the compound BD in Comparative Example 2-1.

< Comparative example 2-2>

An organic light emitting device was manufactured in the same manner as in Comparative Example 2-1, except that the following Compound BD-1 was used instead of Compound BD in Comparative Example 2-1.

Table 2 shows the results of measuring voltage, efficiency, and emission wavelength when current was applied to the organic light emitting devices manufactured by Experimental Examples 2-1 to 2-14 and Comparative Examples 2-1 and Comparative Example 2-2. Shown.

division compound
Emitting layer Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Luminous wavelength
(nm) Comparative Example 2-1 Compound BD 4.75 3.73 460 Experimental Example 2-1 Compound 43 3.90 8.1 450 Experimental Example 2-2 Compound 44 3.92 8.2 451 Experimental Example 2-3 Compound 45 3.91 8.1 452 Experimental Example 2-4 Compound 47 3.90 8.1 450 Experimental Example 2-5 Compound 48 3.89 8.3 451 Experimental Example 2-6 Compound 49 3.88 8.1 453 Experimental Example 2-7 Compound 89 3.80 8.5 455 Experimental Example 2-8 Compound 90 3.81 8.7 454 Experimental Example 2-9 Compound 91 3.85 8.3 456 Experimental Example 2-10 Compound 92 3.80 8.7 455 Experimental Example 2-11 Compound 93 3.80 8.3 457 Experimental Example 2-12 Compound 94 3.84 8.9 455 Experimental Example 2-13 Compound 95 3.87 8.2 454 Experimental Example 2-14 Compound 96 3.88 8.5 455 Comparative Example 2-2 Compound BD-1 4.35 5.5 465

As shown in Table 2, all of the devices of Experimental Examples 2-1 to 2-14 using a compound having the structure of Formula 1 as a core have a lower voltage and efficiency than the devices using the compound BD material in Comparative Example 2-1. I got this ascending result.

In addition, when comparing with the device of Comparative Example 2-2, it was found that the structure of Formula 1 in an asymmetrical form improved both in terms of voltage and efficiency.

As shown in the results of Table 2, it was confirmed that the compound according to the present invention has excellent luminescence ability and is capable of tuning the emission wavelength, thereby realizing an organic light emitting device having high color purity.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: Electronic blocking layer
9: electron injection and transport layer

Claims (12)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X is S, O or NAr,
The Ar is a substituted or unsubstituted aryl group, or the Ar may combine with R2 to form a substituted or unsubstituted indole ring,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group; Two adjacent substituents are bonded to each other to form a substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Substituted or unsubstituted indene ring; Substituted or unsubstituted cyclopentene goric; Substituted or unsubstituted indole rings; Substituted or unsubstituted benzofuran ring; To form a substituted or unsubstituted benzothiophene ring, or can be linked by O, S, or NRa,
Ra is a substituted or unsubstituted aryl group,
m is an integer from 0 to 6, when m is 2 or more, R1 is the same or different from each other, n is an integer from 0 to 7, and when n is 2 or more, R2 is the same or different from each other,
The "substituted or unsubstituted" is substituted with 1 or 2 or more substituents selected from the group consisting of deuterium, nitrile group, alkyl group, silyl group, amine group, and aryl group, or two or more of the substituents exemplified above are connected. Means The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by Formula 2:
[Formula 2]

In Formula 2, X, R1 and m are the same as in Formula 1,
R3 is hydrogen; heavy hydrogen; Nitrile group; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group,
The definition of R4 is the same as that of R2 in Formula 1,
o is an integer from 0 to 4, and when o is 2 or more, R4 is the same as or different from each other,
The "substituted or unsubstituted" is substituted with 1 or 2 or more substituents selected from the group consisting of deuterium, nitrile group, alkyl group, silyl group, amine group, and aryl group, or two or more of the substituents exemplified above are connected. Means The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following Formulas 3 to 6:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6,
The definition of X, R1 and m are the same as in Formula 1,
R5 to R7 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, or substituted or unsubstituted aryl Ki,
p is an integer from 0 to 3, and when p is 2 or more, R5 is the same as or different from each other,
q is an integer from 0 to 6, and when q is 2 or more, R6 is the same as or different from each other,
r is an integer from 0 to 8, and when r is 2 or more, R7 is the same as or different from each other,
The "substituted or unsubstituted" is substituted with 1 or 2 or more substituents selected from the group consisting of deuterium, nitrile group, alkyl group, silyl group, amine group, and aryl group, or two or more of the substituents exemplified above are connected. Means The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following Formulas 7 to 18:
[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

In the above formulas 7 to 18,
The definition of X, R2, and n is the same as in Formula 1,
Y is CRR', NR", O, or S,
R, R', R" and R10 to R15 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group , Or a substituted or unsubstituted aryl group,
a and b are integers from 0 to 4,
c is an integer from 0 to 6,
d is an integer from 0 to 8,
e is an integer from 0 to 3,
f is an integer from 0 to 5,
When a to f are 2 or more, the substituents in parentheses are the same as or different from each other,
The "substituted or unsubstituted" is substituted with 1 or 2 or more substituents selected from the group consisting of deuterium, nitrile group, alkyl group, silyl group, amine group, and aryl group, or two or more of the substituents exemplified above are connected. Means The method according to claim 1, wherein Formula 1 is a compound represented by Formula 20:
[Formula 20]

In Chemical Formula 20, R1, and m are as defined in Chemical Formula 1,
R21 and R22 are the same as the definition of R2 in Chemical Formula 1,
n1 is an integer from 0 to 3, n2 is an integer from 0 to 7,
When n1 and n2 are each 2 or more, the substituents in parentheses are the same or different from each other. The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 21 to 23:
[Formula 21]

[Formula 22]

[Formula 23]

In Chemical Formulas 21 to 23, X and Ra are the same as those in Chemical Formula 1,
R23 and R24 are as defined for R1 and R2 in Formula 1,
n3 is an integer from 0 to 6, n4 is an integer from 0 to 5,
When n3 and n4 are 2 or more, the substituents in parentheses are the same or different from each other. The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently hydrogen; Nitrile group; Methyl group; Butyl group; A diphenylamine group unsubstituted or substituted with an alkyl group; A phenyl group unsubstituted or substituted with a nitrile group; Naphthyl group; Trimethylsilyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group; Two adjacent substituents are bonded to each other to form a substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Substituted or unsubstituted indene ring; A substituted or unsubstituted cyclopentene ring; Substituted or unsubstituted indole rings; Substituted or unsubstituted benzofuran ring; Or to form a substituted or unsubstituted benzothiophene ring,
The "substituted or unsubstituted" is substituted with 1 or 2 or more substituents selected from the group consisting of deuterium, nitrile group, alkyl group, silyl group, amine group, and aryl group, or two or more of the substituents exemplified above are connected. A compound that means that. The method according to claim 1, wherein the compound represented by Formula 1 is selected from the following structural formula:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 8. device. The organic light emitting device of claim 9, wherein the organic material layer includes a light emitting layer, and the light emitting layer contains the compound. The organic light emitting device of claim 9, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or the electron injection and transport layer contains the compound. The method according to claim 9, The organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer comprises the compound.

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