KR102134960B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by Chemical 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 represented by Chemical Formula 1 and an organic light emitting device including the same.

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

As a material used in the organic light emitting device, a pure organic material or a complex compound in which an organic material and a metal are complex occupies most, and depending on the use, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. It can be divided into. Here, as a hole injection material or a 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 n-type properties, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction, is mainly used. The light emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both the oxidation and reduction states, and excitons formed by recombination of holes and electrons in the light emitting layer are formed. A material with high luminous efficiency that converts it to light when desired is preferred.

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

Korean Patent Publication No. 10-2006-0051619

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

One embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

One of A and A'is S or O, the other is CR5,

One of B and B'is S or O, the other is CR6,

R1, R2, R5 and R6 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

R3 and R4 are each independently a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a heterocycle.

In addition, an exemplary embodiment of the present specification includes an anode, a cathode, and one or more organic material layers disposed between the anode and the cathode, and one or more layers of the organic material layers include a compound of Formula 1 Provides

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. The compound described herein may be used as a material for a hole injection layer, a hole transport layer, a hole injection layer and a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, or an electron injection layer.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 It is done.
3 to 18 are graphs showing MS spectra according to compound synthesis according to an exemplary embodiment of the present specification.

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

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 means deuterium; Halogen group; Nitrile group; Silyl group; Alkyl groups; Phosphine oxide group; Cycloalkyl 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, 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 at the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as “adjacent” to each other.

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

In the present specification, the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc 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, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.

In the present specification, the boron group may be represented by the formula of -BRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically, but not limited to, dimethyl boron group, diethyl boron group, t-butyl dimethyl boron group, diphenyl boron group, phenyl boron group, and the like.

In the present specification, the amine group is -NH2; Alkylamine groups; N-aryl alkylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine 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, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, and the like, but is not limited thereto.

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 60. According to one embodiment, the alkyl group has 1 to 40 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. Specific examples are methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms. According to an exemplary embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2, 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl 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 60 carbon atoms. According to one embodiment, the carbon number of the aryl group is 6 to 30. 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 to have 10 to 60 carbon atoms. According to one embodiment, the carbon number of the aryl group is 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

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등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

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And

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heteroatom containing at least one of N, O, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, dibenzofuran group, benzofuranyl group, phenanthroline group (phenanthroline) , Thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, and dibenzofuranyl group, but are not limited thereto.

In the present specification, the arylamine group means that at least one aryl group is substituted on the amine group, and the heteroarylamine group means that at least one heteroaryl group is substituted on the amine group.

In one embodiment of the present specification, R1, R2, R5 and R6 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1, R2, R5 and R6 are hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; And a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1, R2, R5 and R6 are hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; And a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1, R2, R5 and R6 are hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms; And a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R1, R2, R5 and R6 are hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1, R2, R5 and R6 are hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroarylamine group having 2 to 20 carbon atoms; And a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In addition, in one embodiment of the present specification, R1 and R2, or R5 and R6 are arylamine groups substituted with at least one selected from the group consisting of the same substituted or unsubstituted aryl group and the substituent represented by the following formula (2) to be.

[Formula 2]

In one embodiment of the present specification, R1 and R2, or R5 and R6 are the same substituted or unsubstituted at least one selected from the group consisting of an aryl group having 6 to 60 carbon atoms and a substituent represented by Formula 2 below It is an arylamine group.

In one embodiment of the present specification, R1 and R2, or R5 and R6 are the same substituted or unsubstituted at least one selected from the group consisting of an aryl group having 6 to 30 carbon atoms and a substituent represented by Formula 2 below It is an arylamine group.

In addition, in one embodiment of the present specification, X is CRR', NR", O, S, Si, or Se.

In one embodiment of the present specification, X is CRR', NR", O or S.

In addition, in one embodiment of the present specification, a is an integer from 0 to 7.

In addition, in one embodiment of the present specification, R7 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or when a is 2 or more, may be bonded to adjacent groups to form a ring.

In one embodiment of the present specification, R7 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or when a is 2 or more, may be bonded to adjacent groups to form a ring.

In one embodiment of the present specification, R7 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or when a is 2 or more, they may be bonded to adjacent groups to form a ring.

In one embodiment of the present specification, R7 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or when a is 2 or more, they may be bonded to adjacent groups to form a ring.

In one embodiment of the present specification, R, R'and R" are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, and R and R'may combine with each other to form a ring.

In addition, in one embodiment of the present specification, R, R'and R" are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, and R and R'may combine with each other to form a ring.

In addition, in one embodiment of the present specification, R, R'and R" are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; And it is any one selected from the group consisting of substituted or unsubstituted aryl group, R and R'may be bonded to each other to form a ring.

In addition, in an exemplary embodiment of the present specification, R, R'and R" are each independently a substituted or unsubstituted alkyl group; And it is any one selected from the group consisting of substituted or unsubstituted aryl group, R and R'may be bonded to each other to form a ring.

In addition, in one embodiment of the present specification, R, R'and R" are each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; And a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and R and R'may combine with each other to form a ring.

In addition, in one embodiment of the present specification, R, R', and R" are each independently substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; And a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and R and R'may combine with each other to form a ring.

In addition, in one embodiment of the present specification, the substituent represented by Chemical Formula 2, the substituent represented by Chemical Formula 2 is any one of the following Chemical Formulas 2-1 to 2-8.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

In Chemical Formulas 2-1 to 2-8,

R” is as defined above,

R8 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

b is an integer from 0 to 4,

c is an integer from 0 to 6,

When b or c is 2 or more, R8 is the same or different, respectively.

In addition, in one embodiment of the present specification, R8 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

In addition, in one embodiment of the present specification, R8 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

In addition, in one embodiment of the present specification, R8 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; And it is any one selected from the group consisting of a substituted or unsubstituted aryl group.

In addition, in one embodiment of the present specification, R8 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted 3 to 20 cycloalkyl group; And it is any one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In addition, in one embodiment of the present specification, R8 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted 3 to 10 cycloalkyl group; And it is any one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In addition, in one embodiment of the present specification, the substituent represented by Chemical Formula 2 is any one of the following structures.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be represented by any one of the following structures 1-1 to 1-72.

In addition, in the above structures 1-1 to 1-72, R1 and R2 may each independently be selected from 2-1 to 2-133 below.

Further, according to an exemplary embodiment of the present specification, R1 and R2 are each independently an arylamine group or a heteroarylamine group, and the aryl group or heteroaryl group of the arylamine group and heteroarylamine group is 2-1 to 2 below. It can be selected from -133.

The compound according to the exemplary embodiment of the present specification may be prepared by a manufacturing method described later.

For example, the compound of Formula 1 may have a core structure as shown in Reaction Scheme 1 below. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

[Scheme 1]

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

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 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.

Further, the organic light emitting device according to the present invention is an organic light emitting device including an anode, a cathode, and one or more organic material layers disposed between the anode and the cathode, wherein at least one layer of the organic material layer comprises the compound do.

The organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described compound.

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

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, 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 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, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include at least one layer of an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron injection and electron transport, and at least one of the layers is represented by Formula 1 Compounds.

In the organic light emitting device of the present invention, the organic material layer may include at least one layer of a hole injection layer, a hole transport layer, and a layer that simultaneously performs hole injection and hole transport, and at least one layer of the layers is represented by Formula 1 Compounds.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1. As an example, the compound represented by Chemical Formula 1 may be included as a dopant in the light emitting layer.

As another example, the organic material layer including the compound represented by Chemical Formula 1 may include a compound represented by Chemical Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.

In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds It may include as a dopant.

As another example, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and can be used with an iridium-based (Ir) dopant. have.

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

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

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, using a variety of polymer materials. Can be prepared in layers.

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); A combination of metal and oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), 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 are multilayer structure materials such as LiF/Al or LiO2/Al, and the like, but are not limited thereto.

The hole-injecting material is a material that can be easily injected holes from the anode at a low voltage, and it is preferable that the high-occupied molecular orbital (HOMO) of the hole-injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic compounds, anthraquinones, and polyaniline-based conductive polymers of a poly compound, and the like, but are not limited thereto.

As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer is suitable for a material having high mobility for holes. 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.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. 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 (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The host material of the light emitting layer includes 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 carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The iridium-based complex used as a dopant in the light emitting layer is as follows, but is not limited thereto.

[Ir(piq)3]　　　　　　　[Btp2Ir(acac)]

[Ir(ppy)3]　　　　　　　　　　[Ir(ppy)2(acac)]

[Ir(mpyp)3]　　　　　　　[F2Irpic]

[(F2ppy)2Ir(tmd)]　　　　　　　　　[Ir(dfppz)3]

　　　

　　　

As the electron transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

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

The compound according to the present invention may also act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like.

Hereinafter, the present application will be described in more detail through examples according to an exemplary embodiment of the present specification, but the scope of the present invention is not limited thereto.

< Manufacturing example 1> Compound A to H of synthesis

1-1) Synthesis of Compound A

3-bromofuran (22.5) dissolved in 2.5 M n-butyllithium (61.3 mL, 153.3 mmol) in anhydrous diethyl ether (50 ml) at -78 °C, and in anhydrous diethyl ether (25 ml). g, 153.3 mmol) was slowly added dropwise, followed by stirring for 3 hours. Furan-3-carbaldehyde (14.7 g, 153.3 mmol) was slowly added at -78 °C and stirred for 30 minutes, then isothermized to room temperature and stirred for 30 minutes. After cooling again to -23°C, 2.5 M of n-butyllithium (122.6 mL, 306.6 mmol) was added dropwise, followed by stirring again for 2 hours, isotherm to room temperature, and stirring for 30 minutes. Iodine (116.7 g, 459.9 mmol) was dissolved in ether, slowly added dropwise and stirred for 24 hours. The pH was adjusted to 6 using a 1N aqueous hydrochloric acid solution and an aqueous sodium sulfite solution, extracted with ether (100 mL), and the extracted organic layer was concentrated under reduced pressure. The concentrated mixture was purified by column chromatography (silica gel; ethyl acetate/hexane=1/9 (v:v)) to obtain compound A (25 g, 36.4 %).

1-2) Synthesis of Compound B

Compound A (23.2 g, 55.8 mmol) prepared in 1-1) was dissolved in chloroform (50 mL) and pyridinium chlorochromate (PCC, 18 g, 83.7 mmol) was added, followed by stirring at room temperature for 12 hours. Did. Then, the mixture was concentrated under reduced pressure, and the concentrated mixture was purified by column chromatography (silica gel; ethyl acetate/hexane=1/8 (v:v)) to obtain compound B (18.5 g, 80%).

1-3) Synthesis of Compound C

Compound B (7.7 g, 20.6 mmol) prepared in 1-2) was dissolved in anhydrous dimethylformimide (DMF, 50 mL) and stirred, followed by copper powder (Cu powder, 3.92 g, 61.8 mmol) at a time. It was added and refluxed for 24 hours. The refluxed mixture was cooled to room temperature, filtered, and distilled water (10 ml) was added, followed by extraction with ether (20 ml). The extracted organic layer was concentrated under reduced pressure, and the concentrated mixture was purified by column chromatography (silica gel; ethyl acetate/hexane=1/9 (v:v)) to obtain compound C (3 g, 76.6 %).

1-4) Synthesis of Compound D

After dissolving Compound C (2.53 g, 15.8 mmol) and potassium hydroxide (3.02 g, 53.8 mmol) prepared in 1-3) in triethylene glycol (200 mL), 80% hydrazine hydrate (18.2 mL) ) Was added and heated to 180° C. and stirred for 24 hours. Then, cooled to room temperature, filtered, and then distilled water (30 mL) was added. The mixture was extracted with ether (100 mL), and the extracted organic layer was concentrated under reduced pressure. The concentrated mixture was purified by column chromatography (silica gel; ethyl acetate/hexane=1/20 (v:v)) to obtain compound D (1.31 g, 56.7 %).

1-5) Synthesis of Compound E

Compound E was synthesized in the same manner as 1-1) above using 3-bromothiophene and thiophene-3-carbaldehyde.

1-6) Synthesis of Compound F

Compound F was synthesized in the same manner as in 1-2) using Compound E prepared in 1-5).

1-7) Synthesis of Compound G

Compound G was synthesized in the same manner as in 1-3) using Compound F prepared in 1-6).

1-8) Synthesis of Compound H

Compound H was synthesized in the same manner as 1-4) using compound G prepared in 1-7).

< Manufacturing example 2> Synthesis of Compounds I to AB

2-1) Synthesis of Compound I

Compound D (10.0 g, 68.4 mmol), 4-bromopyridine (27.0 g, 171 mmol) and sodium sulfate butoxide (32.9 g, 342 mmol) were dissolved in toluene (300 mL) and refluxed. Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2; 766 mg, 0.684 mmol) and tricyclohexylphosphine (PCy3; 383 mg, 1.37 mmol) were dissolved in 30 mL of toluene and stirred for 30 minutes. Input. After refluxing for 24 hours, the mixture was added with distilled water (100 mL), extracted with methylene chloride (MC, 300 mL), and the extracted organic layer was concentrated under reduced pressure. The concentrated mixture was purified by column chromatography to obtain compound I (16.6 g, 81%).

2-2) Synthesis of Compound J

Compound J was synthesized in the same manner as in 2-1) above using compound H.

2-3) Synthesis of Compound K

A solution in which compound I (2 g, 6.66 mmol) was dissolved in 100 mL of chloroform and bromine (2.2 g, 13.98 mmol) in 50 mL of chloroform was slowly added. And stirred at room temperature for 12 hours. Methanol was added to the reaction solution, and the precipitated solid was filtered to obtain compound K (2.6 g, 85%).

2-4) Synthesis of Compound L

Compound L was synthesized by the same method as 2-3) using Compound J.

2-5) Synthesis of Compound M

Compound M was obtained by the same method as 2-1) above, except that 5-bromopyrimidine was used instead of 4-bromopyridine.

2-6) Synthesis of Compound N

Compound N was synthesized in the same manner as in 2-5) above using compound H.

2-7) Synthesis of Compound O and P

Compounds O and P were synthesized in the same manner as in 2-3) using compounds M and N, respectively.

2-8) Synthesis of Compound Q

9-(2-Bromophenyl)carbazole (15 g, 46.5 mmol) was dissolved in tetrahydrofuran (THF, 200 mL) and cooled to -78 °C. To the solution, 2.5 M of n-butyllithium (16.8 mL, 41.9 mmol) was slowly added dropwise, followed by stirring for 1 hour. Compound C (5.70 g, 35.6 mmol) was added to the solution, stirred for 1 hour, and isothermized to room temperature and stirred for 2 hours. After neutralizing with 1N ammonium chloride solution (300 mL), the organic layer was concentrated under reduced pressure by extraction with chloroform (300 mL). The concentrated mixture was recrystallized from toluene and hexane to obtain compound Q (12.5 g, 87%).

2-9) Synthesis of Compound R

Compound R was synthesized using the same method as 2-8) above.

2-10) Synthesis of Compound S

Compound Q (10 g, 24.8 mmol) was dissolved in acetic acid (100 mL) and sulfuric acid (2 mL) was added. The solution was stirred at reflux for 2 hours and toluene (300 mL) was added. Neutralized with saturated sodium carbonate solution, the organic layer was separated and concentrated under reduced pressure. The concentrated mixture was recrystallized from toluene and hexane to obtain compound S (9.27 g, 97%).

2-11) Synthesis of Compound T

Compound T was synthesized in the same manner as in 2-10) using Compound R.

2-12) Synthesis of Compounds U and V

Compounds U and V were synthesized in the same manner as in 2-3) using compounds S and T, respectively.

2-13) Synthesis of Compound W

Compound W was obtained by the same method as 2-8 above, except that 10-(2-bromophenyl)phenoxazin was used instead of 9-(2-bromophenyl)carbazole.

2-14) Synthesis of Compound X

Compound X was synthesized in the same manner as in 2-13) using Compound G.

2-15) Synthesis of Compounds Y and Z

Compounds Y and Z were synthesized in the same manner as 2-10) above using compounds W and X, respectively.

2-16) Synthesis of Compounds AA and AB

Compounds AA and AB were synthesized in the same manner as in 2-3) using compounds Y and Z, respectively.

<Production Example 3> Synthesis of Synthesis Examples 1 to 16

3-1) Synthesis of Synthesis Example 1

Dehydrate compound K (2.75 g, 6.0 mmol), N-(naphthalen-2-yl)dibenzofuran-2-amine (5.57 g, 18 mmol) and sodium tertiary butoxide (tBuONa, 1.45 g, 15 mmol) It was dissolved in xylene (30 mL), and bis(tritteroxymethoxyphosphine)palladium (30 mg, 0.06 mmol) was added, followed by reflux stirring for 6 hours. After cooling to room temperature, water was added and extracted with toluene (200 mL). Dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by column chromatography to give compound 1 (4.5 g, 82%). ([M+] = 915)

3 is a graph showing the MS spectrum of Compound 1 above.

3-2) Synthesis of Synthesis Example 2

Compound 2 was synthesized in the same manner as 3-1) above using compound K and 6-(tertiarybutyl)-N-(4-(tertiarybutyl)phenyl)dibenzofuran-4-amine. ([M+] = 1039)

4 is a graph showing the MS spectrum of Compound 2.

3-3) Synthesis of Synthesis Example 3

Compound 3 was synthesized in the same manner as in 3-1) above using compound K and N-(4-isopropylphenyl)benzene-d5-amine. ([M+] = 729)

5 is a graph showing the MS spectrum of Compound 3.

3-4) Synthesis of Synthesis Example 4

Compound 4 was synthesized in the same manner as in 3-1) using compound L and N-(4-isopropylphenyl)dibenzothiophen-1-amine. ([M+] = 963)

6 is a graph showing the MS spectrum of the compound 4.

3-5) Synthesis of Synthesis Example 5

Compound 5 was synthesized in the same manner as 3-1) above using compound L and N-([1,1'-biphenyl]4-yl)-9,9'-dimethylfluoren-2-amine. ([M+] = 1051)

7 is a graph showing the MS spectrum of the compound 5.

3-6) Synthesis of Synthesis Example 6

Compound 6 was synthesized in the same manner as 3-1) above using compound O and N-(4-tertarybutylphenyl)benzene-d5-amine. ([M+] = 759)

8 is a graph showing the MS spectrum of Compound 6.

3-7) Synthesis of Synthesis Example 7

Compound 7 was synthesized in the same manner as 3-1) above using compound O and N-(o-tolyl)-[1,1'-biphenyl]-4-amine. ([M+] = 817)

9 is a graph showing the MS spectrum of Compound 7.

3-8) Synthesis of Synthesis Example 8

Compound 8 was synthesized in the same manner as in 3-1) above using compound P and diphenylamine. ([M+] = 669)

10 is a graph showing the MS spectrum of Compound 8.

3-9) Synthesis of Synthesis Example 9

Compound 9 was synthesized in the same manner as 3-1) above using compound P and 9-phenyl-N-(phenyl-d5)-9H-carbazole-2-amine. ([M+] = 1009)

11 is a graph showing the MS spectrum of the compound 9.

3-10) Synthesis of Synthesis Example 10

Compound 10 was synthesized in the same manner as in 3-1) using compound U and di([1,1'-biphenyl]-2-yl)amine. ([M+] = 1024)

12 is a graph showing the MS spectrum of Compound 10.

3-11) Synthesis of Synthesis Example 11

Compound 11 was synthesized in the same manner as 3-1) above using compound U and 4-(naphthalen-2-ylamino)benzonitrile. ([M+] = 870)

13 is a graph showing the MS spectrum of Compound 11 above.

3-12) Synthesis of Synthesis Example 12

Compound 12 was synthesized in the same manner as in 3-1) above using compound U and 2-methyl-N-phenylaniline. ([M+] = 748)

14 is a graph showing the MS spectrum of Compound 12.

3-13) Synthesis of Synthesis Example 13

Compound 13 was synthesized in the same manner as 3-1) above using compound V and N-(6-fluoronaphthalen-2-yl)dibenzothiophen-1-amine. ([M+] = 1100)

15 is a graph showing the MS spectrum of Compound 13.

3-14) Synthesis of Synthesis Example 14

Compound 14 was synthesized in the same manner as 3-1) above using compound V and N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine. ([M+] = 996)

16 is a graph showing the MS spectrum of the compound 14.

3-15) Synthesis of Synthesis Example 15

Compound 15 was synthesized in the same manner as 3-1) above using compound AA and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. ([M+] = 968)

17 is a graph showing the MS spectrum of Compound 15.

3-16) Synthesis of Synthesis Example 16

Compound 16 was synthesized in the same manner as 3-1) above using compound AB and N-(naphthalen-1-yl)fluoranthen-3-amine. ([M+] = 1116)

18 is a graph showing the MS spectrum of Compound 16.

<Production Example 4> Preparation of Comparative Examples and Examples

4-1) Preparation of Comparative Example 1

A glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,500 에 was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as 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 then transported 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.

(HAT)

(HAT)

A hole transport layer is vacuum-deposited by depositing 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 kPa) of the following formula, which is a material for transporting holes on the hole injection layer. Formed.

(NPB)

(NPB)

Subsequently, 9-(naphthalen-1-yl)-10-(naphthalen-2-yl)anthracene (BH1) of the following formula was vacuum deposited on the hole transport layer to a thickness of 300 MPa to form a light emitting layer.

(BH)

(BH)

4% by weight of the following compound N4,N9-bis(dibenzofuran-4-yl)-N4,N9-di-m-tolylpyrene-4,9-diamine (BD1) was used as a blue light emitting dopant while depositing the light emitting layer. Did.

(BD1)

(BD1)

An electron injection and transport layer was formed by vacuum-depositing Alq3 (aluminum tris(8-hydroxyquinoline)) of the following formula on the light emitting layer to a thickness of 200 Pa.

(Alq3)

(Alq3)

On the electron injection and transport layer, lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 2,000 위에 were sequentially deposited to form a cathode.

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 the aluminum was maintained at a deposition rate of 2 Å/sec, and the vacuum degree during deposition was 2×10. -7~5×10-8 torr was maintained.

The performance of the device manufactured as above was measured.

4-2) Preparation of Comparative Examples 2 to 3

Blue emitting layer dopant material, instead of BD1, N2,N2,N6,N6-tetrakis(4-tertiarybutylphenyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']difuran -2,6-diamine (BD2) or N2,N2,N6,N6-tetraphenylspiro[cyclopenta[2,1-b:3,4-b']dithiophene-4,9'-fluorene]- The device performance was measured in the same manner as in Comparative Example 1, except that 2,6-diamine (BD3) was used, respectively.

(BD3) (BD2)

4-3) Preparation of Examples 1 to 16

The device performance was measured in the same manner as in Comparative Example 1, except that compounds 1 to 12 were used instead of BD1 as a blue light emitting layer dopant material.

Table 1 shows the results of experiments of the organic light emitting devices manufactured by using each compound as a blue dopant material at a current density of 20 mA/cm ² as in Comparative Examples 1 to 3 and Examples 1 to 12.

Experimental Example Dopant material Voltage (V) Efficiency (Cd/A) Color coordinate CIE_y Lifetime T97% (hours) Comparative Example 1 BD1 5.29 5.75 0.046 110 Comparative Example 2 BD2 5.21 5.72 0.052 101 Comparative Example 3 BD3 5.12 5.48 0.049 76 Example 1 Synthesis Example 1 5.14 6.58 0.052 141 Example 2 Synthesis Example 2 5.10 6.81 0.050 135 Example 3 Synthesis Example 3 5.14 6.51 0.051 152 Example 4 Synthesis Example 4 5.08 6.89 0.048 92 Example 5 Synthesis Example 5 5.11 6.70 0.050 99 Example 6 Synthesis Example 6 5.08 6.73 0.049 149 Example 7 Synthesis Example 7 5.09 6.76 0.049 140 Example 8 Synthesis Example 8 5.11 6.03 0.053 82 Example 9 Synthesis Example 9 5.12 6.58 0.053 93 Example 10 Synthesis Example 10 5.13 6.83 0.046 147 Example 11 Synthesis Example 11 5.09 6.65 0.047 139 Example 12 Synthesis Example 12 5.11 6.40 0.048 140 Example 13 Synthesis Example 13 5.08 6.79 0.048 97 Example 14 Synthesis Example 14 5.10 6.79 0.049 89 Example 15 Synthesis Example 15 5.09 6.71 0.051 145 Example 16 Synthesis Example 16 5.08 6.89 0.052 103

As can be seen from the above table, it can be seen that the compound according to the present specification exhibits excellent device characteristics.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer

Claims (8)

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

In Chemical Formula 1,
One of A and A'is S or O, the other is CR5,
One of B and B'is S or O, the other is CR6,
R1 and R2 are each independently a substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heteroarylamine group,
R5 and R6 are hydrogen,
R3 and R4 are each independently a substituted or unsubstituted heterocyclic group, or may combine with each other to form a heterocycle containing N. The method according to claim 1,
R1 and R2 are arylamine groups substituted with at least one selected from the group consisting of aryl groups which are identically substituted or unsubstituted and substituents represented by the following formula (2),
[Formula 2]

X is CRR', NR”, O, S or Se,
a is an integer from 0 to 7,
When a is 2 or more, R7 is the same or different from each other,
R7 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or when a is 2 or more, may be mutually bonded to an adjacent group to form a substituted or unsubstituted ring,
R, R'and R" are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.
R and R'may combine with each other to form a ring. The method according to claim 2,
The substituent represented by Formula 2 is any one of the following Formulas 2-1 to 2-8:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

[Formula 2-8]

In Chemical Formulas 2-1 to 2-8,
R” is as defined in claim 2,
R8 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.
b is an integer from 0 to 4,
c is an integer from 0 to 6,
When b or c is 2 or more, R8 is the same or different, respectively. The method according to claim 2,
The substituent represented by Formula 2 is any one of the following structures:

. An organic light emitting device comprising an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, and at least one layer of the organic layer includes a compound according to any one of claims 1 to 4. The method according to claim 5,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer is an organic light emitting device comprising the compound of Formula 1. The method according to claim 5,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of Formula 1. The method according to claim 5,
The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound of formula (1).

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