KR102069431B1 - 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

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2017-0025637 filed with the Korea Patent Office on February 27, 2017, the entire contents of which are incorporated herein.

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

Organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

International Patent Application Publication No. 2003-012890

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

The present specification provides a compound represented by the following Formula 1.

[Formula 1]

In Chemical Formula 1,

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

Ar1 is a substituted or unsubstituted two or more heterocyclic group containing two or more N,

R1 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a ring.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to the exemplary embodiment of the present specification may be used in an organic light emitting device to lower the driving voltage of the organic electric device.

In addition, the compound according to one embodiment of the present specification may be used in an organic light emitting device to improve light efficiency.

In addition, the compound according to the exemplary embodiment of the present specification may be used in an organic light emitting device to improve lifespan characteristics of the device by thermal stability of the compound.

1 illustrates an organic light emitting device 10 according to an exemplary embodiment of the present specification.
2 illustrates an organic light emitting device 11 according to another exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

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

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

는 연결되는 부위를 의미한다.In the present specification,

Means a site to be connected.

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Alkyl groups; Cycloalkyl group; Amine groups; Silyl groups; Phosphine oxide groups; Aryl group; And one or two or more substituents selected from the group consisting of a heteroaryl group including one or more of N, O, S, Se, and Si atoms, or two or more substituents among the substituents exemplified above are substituted with a substituent, or any It means that it does not have a substituent.

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

In the present specification, the alkyl group may be linear or branched, carbon number is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30. Specific examples include 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-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 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 60 carbon atoms, more preferably 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, but is not limited thereto.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , and R ₂₀₁ to R ₂₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, or the like, but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C50, and 10-30 are more preferable. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryllenyl group, triphenyl 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.

,

,

,

,

,

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

,

,

,

,

,

Etc., but is not limited thereto.

In the present specification, the heterocyclic group includes one or more of N, O, S, Si, and Se as heteroatoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms. Do. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group (phthalazine), pteridine group (pteridine), pyrido pyrimidine, pyrido pyrazine group (pyrido pyrazine) ), Pyrazino pyrazine, isoquinoline, indole, pyrido indole, innopyrimidine, carbazole, benzoxazole group, benzimidazole group, Benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group and thia Diazolyl group, etc., but is not limited to these.

In the present specification, the heteroaryl group may be selected from examples of the heterocyclic group except that it is aromatic, but is not limited thereto.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl groups can be applied except that they are each divalent.

In the present specification, a heteroarylene group means a divalent group having two bonding positions in a heteroaryl group. The description of the heteroaryl group described above can be applied except that they are each divalent.

In one embodiment of the present specification, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L is a direct bond.

In one embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted Triphenylene group, substituted or unsubstituted naphthylene group, or substituted or unsubstituted fluorenylene group.

In one embodiment of the present specification, L is a phenylene group.

In one embodiment of the present specification, L is a naphthylene group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted two or more heterocyclic groups including two or more N.

, 또는 치환 또는 비치환된

이다. In one embodiment of the present specification, Ar1 is a substituted or unsubstituted quinazoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted phthalazine group, a substituted or unsubstituted pteridine group, a substituted or unsubstituted A substituted pyrido pyrimidine group, a substituted or unsubstituted pyrido pyrazine group, a substituted or unsubstituted pyrazino pyrazine group, a substituted or unsubstituted benzoquinazolin group, a substituted or unsubstituted pyrido indole group, a substituted or Unsubstituted indeno pyrimidine groups, substituted or unsubstituted

Or substituted or unsubstituted

to be.

In one embodiment of the present specification, Ar1 is a quinazoline group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a quinazolin group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a quinoxaline group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a quinoxaline group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a phthalazine group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a phthalazine group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenyl group, a phenanthryl group, a fluorenyl group, or a dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a putridine group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a pteridine group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenyl group, a phenanthryl group, a fluorenyl group, or a dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a pyrido pyrimidine group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present specification, Ar1 is a pyrido pyrimidine group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group. .

In one embodiment of the present specification, Ar1 is a pyrido pyrazine group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present specification, Ar1 is a pyrido pyrazine group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a pyrazino pyrazine group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a pyrazino pyrazine group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a benzoquinazolin group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a benzoquinazolin group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is a pyrido indole group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is a pyrido indole group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group.

In one embodiment of the present specification, Ar1 is an indeno pyrimidine group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, Ar1 is an indeno pyrimidine group unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group. .

이다.In one embodiment of the present specification, Ar1 is unsubstituted or substituted with an aryl group.

to be.

이다. In an exemplary embodiment of the present specification, Ar1 is unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group

to be.

이다.In one embodiment of the present specification, Ar1 is unsubstituted or substituted with an aryl group.

to be.

이다. In an exemplary embodiment of the present specification, Ar1 is unsubstituted or substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, phenanthryl group, fluorenyl group, or dimethylfluorenyl group

to be.

In one embodiment of the present specification, Ar1 is a quinazoline group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a quinazoline group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a quinoxaline group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a quinoxaline group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a phthalazine group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a phthalazine group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a putridine group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a pteridine group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a pyrido pyrimidine group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a pyrido pyrimidine group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a pyrido pyrazine group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a pyrido pyrazine group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a pyrazino pyrazine group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a pyrazino pyrazine group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a benzoquinazolin group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a benzoquinazolin group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is a pyrido indole group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a pyrido indole group unsubstituted or substituted with a dibenzofuran group.

In one embodiment of the present specification, Ar1 is an indeno pyrimidine group unsubstituted or substituted with a heterocyclic group.

In one embodiment of the present specification, Ar1 is an indeno pyrimidine group unsubstituted or substituted with a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a dibenzofuran group.

이다.In one embodiment of the present specification, Ar1 is unsubstituted or substituted with a heterocyclic group.

to be.

이다.In one embodiment of the present specification, Ar1 is unsubstituted or substituted with a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a dibenzofuran group

to be.

이다.In one embodiment of the present specification, Ar1 is unsubstituted or substituted with a heterocyclic group.

to be.

이다.In one embodiment of the present specification, Ar1 is unsubstituted or substituted with a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a dibenzofuran group

to be.

In one embodiment of the present specification, Ar1 is any one selected from the following structures.

In one embodiment of the present specification, Ar2 to Ar7 are hydrogen; heavy hydrogen; Halogen group; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, r2 is an integer of 1 to 6, r3 is an integer of 1 to 5, r4 is an integer of 1 to 4, r7 is an integer of 1 to 8, the r2 to r4 and When r7 is each 2 or more, two or more Ar2 to Ar4 and Ar7 are the same as or different from each other.

In one embodiment of the present specification, Ar2 to Ar7 are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms.

In one embodiment of the present specification, Ar2 to Ar7 are substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted isopropyl Group or a substituted or unsubstituted tert-butyl group.

In one embodiment of the present specification, Ar5 and Ar6 are each a methyl group.

In one embodiment of the present specification, Ar2 to Ar7 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar2 to Ar7 are substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted Triphenyl group, substituted or unsubstituted naphthyl group, or substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Ar2 is a phenyl group.

In one embodiment of the present specification, Ar2 is a biphenyl group.

In one embodiment of the present specification, Ar2 is a terphenyl group.

In one embodiment of the present specification, Ar2 is a naphthyl group.

In one embodiment of the present specification, Ar2 is a triphenyl group.

In one embodiment of the present specification, Ar2 is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar3 is a phenyl group.

In one embodiment of the present specification, Ar3 is a biphenyl group.

In one embodiment of the present specification, Ar3 is a terphenyl group.

In one embodiment of the present specification, Ar3 is a naphthyl group.

In one embodiment of the present specification, Ar3 is a triphenyl group.

In one embodiment of the present specification, Ar3 is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar4 is a phenyl group.

In one embodiment of the present specification, Ar4 is a biphenyl group.

In one embodiment of the present specification, Ar4 is a terphenyl group.

In one embodiment of the present specification, Ar4 is a naphthyl group.

In one embodiment of the present specification, Ar4 is a triphenyl group.

In one embodiment of the present specification, Ar4 is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar7 is a phenyl group.

In one embodiment of the present specification, Ar7 is a biphenyl group.

In one embodiment of the present specification, Ar7 is a terphenyl group.

In one embodiment of the present specification, Ar7 is a naphthyl group.

In one embodiment of the present specification, Ar7 is a triphenyl group.

In one embodiment of the present specification, Ar7 is a dimethylfluorenyl group.

In one embodiment of the present specification, R1 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, R1 to R4 may combine with an adjacent group to form a ring.

In one embodiment of the present specification, R1 and R2 may combine with each other to form a ring.

In one embodiment of the present specification, R2 and R3 may combine with each other to form a ring.

In one embodiment of the present specification, R3 and R4 may combine with each other to form a ring.

In one embodiment of the present specification, R5 to R13 are each hydrogen.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,

The definitions for L, Ar1 and R1 to R13 are the same as those defined in Chemical Formula 1.

In one embodiment of the present specification, R14 is hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

In one embodiment of the present specification, a is an integer of 1 to 4, and when a is 2 or more, two or more R14 are the same as or different from each other.

In one embodiment of the present specification, R14 is hydrogen.

In one embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

Compounds according to one embodiment of the present specification may be prepared by the production method described below. In the following production examples, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change the starting materials, reactants, reaction conditions and the like.

For example, the compound represented by Formula 1 may be prepared in the core structure as shown in the following general formula (1). Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. Substituents may be bonded as in Formula 1, but is not limited thereto.

<Formula 1>

In Formula 1, Ar1 and L are the same as defined in Formula 1.

The compound represented by Chemical Formula 1 may be prepared as described above using a reaction such as Suzuki coupling, Buckwald-Hartwig coupling, but is not limited thereto.

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

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

In this specification, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "includes" a certain component, this means that the component may further include other components, except for the case where there is no description to the contrary.

The organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present specification, the organic light emitting device may have a structure including a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injection layer, an electron blocking layer, a hole blocking layer and the like as an organic material layer. have. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a host of the light emitting layer.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1 as a phosphorescent host or a fluorescent host of the light emitting layer.

In one embodiment of the present specification, the organic material layer includes the compound represented by Chemical Formula 1 as a host of the light emitting layer, and includes another organic compound, a metal, or a metal compound as a dopant.

In one embodiment of the present specification, the organic material layer includes the compound represented by Chemical Formula 1 as a host of the light emitting layer, and includes an iridium complex as a dopant.

According to one embodiment of the present specification, the dopant may be selected from the following structures, but is not limited thereto.

In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer comprises a compound represented by the formula (1).

In one embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes a compound represented by Chemical Formula 1.

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

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further comprises one or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer and an electron blocking layer.

In one embodiment of the present specification, the organic light emitting device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, the organic light emitting device will be exemplified.

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

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

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

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

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

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

In one embodiment of the present specification, the organic material layer may further include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group in addition to the organic material layer including the compound.

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

When the organic material layer including the compound represented by Chemical Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may use those known in the art, for example, a metal or a metal complex. For example, the electron transport layer including the compound represented by Chemical Formula 1 may further include LiQ (Lithium Quinolate).

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having an inverted type 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 of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an exemplary embodiment of the present specification, and may further include another organic material layer.

2, the first electrode 30, the hole injection layer 60, the hole transport layer 70, the electron blocking layer 80, the light emitting layer 40, the electron transport layer 90, and the electron injection layer The structure of the organic light emitting device in which the 100 and the second electrode 50 are sequentially stacked is illustrated. 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

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

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. It can be prepared by forming, and forming 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 the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, but is not limited thereto.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and an anode 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 specification, 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.

As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the anode material that can be used include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2: Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.

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 hetero ring-containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds and the like, and heterocyclic containing compounds include dibenzofuran derivatives, ladder type furan compounds, Pyrimidine derivatives, and the like, but is not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene and the like having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamine group. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

In the present specification, when the compound represented by Chemical Formula 1 is included in an organic material layer other than the light emitting layer, or when an additional light emitting layer is provided, the light emitting material of the light emitting layer is transported and bonded with holes and electrons from the hole transporting layer and the electron transporting layer, respectively. As a material capable of emitting light in the visible ray region, a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxyquinoline aluminum complex (Alq 3); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene; And rubrene and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. The hole injection material preferably has the ability to transport holes, and thus has a hole injection effect at the anode and an excellent hole injection effect to the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent the excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferable. In addition, 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 organic metals such as metal porphyrin, oligothiophene, and arylamine; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organics; Perylene-based organic material; Polythiophene-based conductive polymers such as anthraquinone, polyaniline, and the like, 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 the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is preferably a material having high mobility to holes. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the cathode to be transferred to the light emitting layer, and a material having high mobility to electrons is preferable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; 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 in accordance with the prior art. In particular, suitable cathode materials have a low work function and are conventional materials followed by aluminum or silver layers. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, each followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. It is preferable that the electron injection material has excellent ability to transport electrons, and has an electron injection effect from the cathode, and an electron injection effect excellent with respect to the light emitting layer or the light emitting material. In addition, a material which prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like, and derivatives thereof, Metal complex compounds, nitrogen-containing five-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 and bis (8-hydroxyquinolinato) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h ] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The electron blocking layer is a layer that can prevent the holes injected from the hole injection layer to pass through the light emitting layer to the electron injection layer to improve the life and efficiency of the device. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.

The hole blocking layer is a layer that blocks the reaching of the cathode of 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, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 may act on a principle similar to that applied to an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the compound.

Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

< Production Example >

< Production Example  1. Preparation of Chemical Formulas A-1 to A-4>

(1) Preparation of Chemical Formula A-1

300.0 g (1.00 eq) of 4-bromoindolo [3,2,1-jk] carbazole, 172.04 g (1.1 eq) of ((2-nitrophenyl) boronic acid) and 10.82 g (0.01 eq) of Pd (PPh ₃ ) ₄ It dissolved in 5.0 L of tetrahydrofuran (THF), and stirred. Thereafter, 258.98 g (2.0 eq) of K ₂ CO ₃ was dissolved in 1.5 L of water, followed by stirring under reflux. After the reaction was completed after 2 hours, the organic layer was separated, and the solvent was removed under reduced pressure. The product was completely dissolved in CHCl ₃ and washed with water. The solution was concentrated under reduced pressure about 50% and ethanol was added to drop crystals and filtered. Thereafter, the residue was purified using column chromatography to obtain 288.61 g (yield 85%) of compound B-1. MS [M + H] ⁺ = 363

288.61 g (1.0 eq) of the compound 1-1 was dissolved in 1 L of triethyl phosphite (P (OEt) ₃ ) and refluxed to stir. After the reaction was completed after 3 hours, the reaction mixture was vacuum reduced to remove about 50% of the solvent, and then cooled to room temperature and filtered. After completely dissolved in ethyl acetate and washed with water, the solution was concentrated under reduced pressure about 70%, cooled to room temperature and filtered to obtain 184.18 g (Yield 70%) of Compound A-1. MS [M + H] ⁺ = 331

(2) Preparation of Chemical Formula A-2

Except for using (2-nitronaphthalen-1-yl) boronic acid instead of (2-nitrophenyl) boronic acid, the compound A-2 was obtained by the same method as the method of preparing the formula (A-1).

(3) Preparation of Chemical Formula A-3

Except that (3-nitronaphthalen-2-yl) boronic acid was used instead of (2-nitrophenyl) boronic acid, the compound A-3 was obtained by the same method as the method of preparing Formula A-1.

(4) Preparation of Formula A-4

Except for using (1-nitronaphthalen-2-yl) boronic acid instead of (2-nitrophenyl) boronic acid, the compound A-4 was obtained in the same manner as the method of preparing the formula (A-1).

< Production Example  2. Preparation of Compounds 1-1 to 1-12>

(1) Preparation of Compound 1-1

Compound A-1 10.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 9.68 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of xylene and refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then purified by column chromatography to obtain 12.38 g of a compound 1-1 (yield 70%). MS [M + H] ⁺ = 585

(2) Preparation of Compound 1-2

Compound A-1 10.0 g (1.0 eq), 2- (4-bromonaphthalen-1-yl) -4-phenylquinazoline 13.69 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 13.8 g (yield 69%) of compound 1-2. MS [M + H] ⁺ = 661

(3) Preparation of Compound 1-3

Compound A-1 10.0 g (1.0 eq), 3- (2-chloroquinazolin-4-yl) -9-phenyl-9H-carbazole 13.51 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 15.03 g of a compound 1-3 (yield 73%). MS [M + H] ⁺ = 700

(4) Preparation of Compound 1-4

Compound A-1 10.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) benzofuro [3,2-d] pyrimidine 11.01 g (1.1 eq), Pd (t-Bu₃P)₂ 0.07 g (0.005 eq) and K₃PO₄ 12.85 g (2.0 eq) was added to 300 mL of Xylene, and the mixture was refluxed and stirred. After the reaction was completed after 5 hours, the reaction mixture was cooled to room temperature and then removed by depressurizing Xylene. CHCl₃Completely dissolved in the mixture, washed with water, and then depressurized to remove the solvent, which was purified by column chromatography to obtain 13.23 g (yield 70%) of Compound 1-4. MS [M + H]⁺625

(5) Preparation of Compound 1-5

Compound A-1 10.0 g (1.0 eq), 2-chloro-4- (dibenzo [b, d] furan-3-yl) -5,5-dimethyl-5H-indeno [1,2-d] pyrimidine 13.21 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 15.26 g (yield 73%) of compound 1-5. MS [M + H] ⁺ = 691

(6) Preparation of Compound 1-6

Compound A-1 10.0 g (1.0 eq), 2-chloro-4- (9-phenyl-9H-carbazol-2-yl) benzo [4,5] thieno [3,2-d] pyrimidine 15.38 g (1.1 eq ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was removed under reduced pressure, which was then purified by column chromatography to obtain 15.56 g of a compound 1-6 (yield 68%). MS [M + H] ⁺ = 756

(7) Preparation of Compound 1-7

Compound A-1 10.0 g (1.0 eq), 3-chloro-1-phenylbenzo [f] quinazoline 9.68 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 11.86 g (yield 67%) of compound 1-7. MS [M + H] ⁺ = 585

(8) Preparation of Compound 1-8

Compound A-1 10.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) benzo [h] quinazoline 11.34 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was purified by column chromatography to obtain 13.44 g (yield 70%) of compound 1-8. MS [M + H] ⁺ = 635

(9) Preparation of Compound 1-9

Compound A-1 10.0 g (1.0 eq), 6-([1,1'-biphenyl] -4-yl) -2-chloro-4-phenylquinazoline 13.08 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 14.76 g (yield 71%) of compound 1-9. MS [M + H] ⁺ = 687

(10) Preparation of Compound 1-10

Compound A-1 10.0 g (1.0 eq), 2- (4-bromonaphthalen-1-yl) -3- (naphthalen-2-yl) -6-phenylquinoxaline 17.89 g (1.1 eq), Pd (t-Bu ₃ P ) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 14.96 g (yield 68%) of compound 1-10. MS [M + H] ⁺ = 727

(11) Preparation of Compound 1-11

Compound A-1 10.0 g (1.0 eq), 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -7-phenylquinazoline 14.41 g (1.1 eq), Pd (t-Bu ₃ P ) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 14.96 g (yield 68%) of compound 1-11. MS [M + H] ⁺ = 727

(12) Preparation of Compound 1-12

Compound A-1 10.0 g (1.0 eq), 2-chloro-3- (9,9-dimethyl-9H-fluoren-2-yl) quinoxaline 11.88 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was purified by column chromatography to obtain 13.59 g (yield 69%) of compound 1-12. MS [M + H] ⁺ = 651

< Production Example  3. Preparation of Compounds 2-1 to 2-8>

(1) Preparation of Compound 2-1

Compound A-2 10.0 g (1.0 eq2-chloro-4- (dibenzo [b, d] thiophen-4-yl) benzofuro [3,2-d] pyrimidine 11.18 g (1.1 eq), Pd (t-Bu ₃ P ) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was purified by column chromatography to obtain 13.25 g (yield 69%) of compound 2-1. MS [M + H] ⁺ = 731

(2) Preparation of Compound 2-2

Compound A-2 10.0 g (1.0 eq2-chloro-5,5-dimethyl-4- (9-phenyl-9H-carbazol-2-yl) -5H-indeno [1,2-d] pyrimidine 13.64 g (1.1 eq ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was distilled off under reduced pressure, which was then purified by column chromatography to obtain 15.87 g of a compound 2-2 (yield 74%). MS [M + H] ⁺ = 816

(3) Preparation of Compound 2-3

Compound A-2 10.0 g (1.0 eq), 2-chloro-4- (dibenzo [b, d] furan-4-yl) benzo [4,5] thieno [3,2-d] pyrimidine 11.18 g (1.1 eq ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and removed under reduced pressure again to purify the solvent, which was purified by column chromatography to obtain 13.44 g of a compound 2-3 (yield 70%). MS [M + H] ⁺ = 731

(4) Preparation of Compound 2-4

Compound A-2 10.0 g (1.0 eq), 3-chloro-1- (dibenzo [b, d] furan-3-yl) benzo [f] quinazoline 11.01 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. Completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was purified by column chromatography to obtain 13.90 g (yield 73%) of Compound 2-4. MS [M + H] ⁺ = 725

(5) Preparation of Compound 2-5

Compound A-2 10.0 g (1.0 eq), 3- (4-chlorophenyl) -2-phenylpyrido [2,3-b] pyrazine 9.18 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was removed under reduced pressure, which was then purified by column chromatography to obtain 12.53 g (yield 72%) of compound 2-5. MS [M + H] ⁺ = 662

(6) Preparation of Compound 2-6

Compound A-2 10.0 g (1.0 eq), 2-chloro-4-phenylpteridine 7.07 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq ) Was added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 11.25 g (yield 73%) of compound 2-6. MS [M + H] ⁺ = 587

(7) Preparation of Compound 2-7

Compound A-2 10.0 g (1.0 eq), 4- (4-bromophenyl) -2- (naphthalen-2-yl) -7-phenylquinazoline 14.09 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 14.68 g (yield 71%) of compound 2-7. MS [M + H] ⁺ = 787

(8) Preparation of Compound 2-8

Compound A-2 10.0 g (1.0 eq), 4-chloro-2- (naphthalen-2-yl) -7-phenylpteridine 10.66 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 13.67 g (yield 73%) of Compound 2-8. MS [M + H] ⁺ = 713

< Production Example  4. Preparation of Compounds 3-1 to 3-7>

(1) Preparation of Compound 3-1

Compound A-3 10.0 g (1.0 eq), 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) quinazoline 10.31 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 13.26 g (yield 72%) of compound 3-1. MS [M + H] ⁺ = 701

(2) Preparation of Compound 3-2

Compound A-3 10.0 g (1.0 eq), 2-chloro-4- (9-phenyl-9H-carbazol-2-yl) benzofuro [3,2-d] pyrimidine 12.89 g (1.1 eq), Pd (t- Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was purified by column chromatography to obtain 14.53 g (yield 70%) of compound 3-2. MS [M + H] ⁺ = 790

(3) Preparation of Compound 3-3

Compound A-3 10.0 g (1.0 eq), 4-([1,1'-biphenyl] -4-yl) -2-chloro-5,5-dimethyl-5H-indeno [1,2-d] pyrimidine 11.07 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was distilled off under reduced pressure, which was purified by column chromatography to obtain 12.80 g of a compound 3-3 (yield 67%). MS [M + H] ⁺ = 727

(4) Preparation of Compound 3-4

Compound A-3 10.0 g (1.0 eq), 2- (4-bromonaphthalen-1-yl) -4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine 13.51 g (1.1 eq), Pd (t -Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was distilled off under reduced pressure, which was purified by column chromatography to obtain 15.52 g (yield 77%) of compound 3-4. MS [M + H] ⁺ = 767

(5) Preparation of Compound 3-5

Compound A-3 10.0 g (1.0 eq), 4-chloro-2- (naphthalen-2-yl) pyrido [3,2-d] pyrimidine 8.73 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq)? 12.85 g (2.0 eq) of K ₃ PO ₄ was added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 11.52 g (yield 69%) of compound 3-5. MS [M + H] ⁺ = 636

(6) Preparation of Compound 3-6

Compound A-3 10.0 g (1.0 eq), 2- (4-bromophenyl) -4,6-diphenylpyrido [2,3-d] pyrimidine 12.67 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 11.83 g (yield 61%) of compound 3-6. MS [M + H] ⁺ = 738

(7) Preparation of Compound 3-7

Compound A-3 10.0 g (1.0 eq), 2- (3-chloro-6-phenylquinoxalin-2-yl) -9-phenyl-9H-carbazole 13.93 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 14.54 g (yield 67%) of compound 3-7. MS [M + H] ⁺ = 826

< Production Example  5. Preparation of Compounds 4-1 to 4-8>

(1) Preparation of Compound 4-1

Compound A-4 10.0 g (1.0 eq), 4-chloro-2-phenylquinazoline 6.95 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 11.06 g (yield 72%) of compound 4-1. MS [M + H] ⁺ = 585

(2) Preparation of Compound 4-2

Compound A-4 10.0 g (1.0 eq), 2- (4-bromonaphthalen-1-yl) -3- (naphthalen-2-yl) quinoxaline 13.33 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was removed under reduced pressure, which was purified by column chromatography to obtain compound 4-2 14 g (yield 70%). MS [M + H] ⁺ = 761

(3) Preparation of Compound 4-3

Compound A-4 10.0 g (1.0 eq), 2- (4-bromophenyl) -3-phenylpyrido [2,3-b] pyrazine 10.47 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then purified by column chromatography to obtain 11.83 g (yield 68%) of compound 4-3. MS [M + H] ⁺ = 662

(4) Preparation of Compound 4-4

Compound A-4 10.0 g (1.0 eq), 2-chloro-3-phenylpyrazino [2,3-b] pyrazine 7.00 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 11.10 g (yield 72%) of compound 4-4. MS [M + H] ⁺ = 587

(5) Preparation of Compound 4-5

Compound A-4 10.0 g (1.0 eq), 3- (4-bromophenyl) -2,7-diphenylpyrido [2,3-b] pyrazine 12.67 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and NaOtBu 5.82 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was removed under reduced pressure, which was purified by column chromatography to obtain 13.38 g (69%) of compound 4-5. MS [M + H] ⁺ = 738

(6) Preparation of Compound 4-6

Compound A-4 10.0 g (1.0 eq), 3-chloro-1- (dibenzo [b, d] thiophen-4-yl) benzo [f] quinazoline 11.47 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was purified by column chromatography to obtain 13.63 g (yield 70%) of compound 4-6. MS [M + H] ⁺ = 741

(7) Preparation of Compound 4-7

Compound A-4 10.0 g (1.0 eq), 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine 8.58 g (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ , washed with water, and again depressurized to remove the solvent, which was purified by column chromatography to obtain 10.94 g (yield 65%) of compound 4-7. MS [M + H] ⁺ = 641

(8) Preparation of Compound 4-8

Compound A-4 10.0 g (1.0 eq), 2-chloro-4- (dibenzo [b, d] furan-3-yl) benzo [4,5] thieno [3,2-d] pyrimidine 11.18 g (1.1 eq ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) and K ₃ PO ₄ 12.85 g (2.0 eq) were added to 300 mL of Xylene, and the mixture was refluxed and stirred. After 5 hours, when the reaction was completed, the mixture was cooled to room temperature and then removed by depressurizing Xylene. It was completely dissolved in CHCl ₃ and washed with water, and the solvent was removed under reduced pressure again, which was purified by column chromatography to obtain 11.71 g (yield 61%) of compound 4-8. MS [M + H] ⁺ = 731

< Example >

< Example  1>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After washing ITO for 30 minutes, ultrasonic washing was repeated 10 minutes with distilled water twice. After the distilled water wash, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The following hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited to a thickness of 150 kPa on the prepared ITO transparent electrode to form a thin film.

Subsequently, the following compound HT-1 was deposited to a thickness of 1,150 GPa on the thin film to form a hole transport layer, and the compound of the following compound EB-1 was deposited to a thickness of 100 GPa thereon to form an electron blocking layer.

Subsequently, the compound 1-1 as a host and the compound of Dp-7 as a dopant were vacuum deposited to a thickness of 300 kPa to form a light emitting layer. At this time, 3% by weight of Dp-7 was used based on the total weight of the compounds 1-1 and Dp-7.

After the compound HB-1 was deposited to a thickness of 50 GPa on the emission layer to form a hole blocking layer, the compound ET-1 was deposited to a thickness of 310 GPa to form an electron transport layer.

12 전자 of lithium fluoride (LiF) and 1,000 Å of aluminum were sequentially deposited on the electron transport layer to form a cathode.

Was maintained at a vapor deposition rate of 0.4 to 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 10 2 X ^{- The} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁶ torr.

< Example  2 to Example  12>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-2 to Compound 1-12 were used instead of Compound 1-1 in Example 1.

< Example  13 to Example  20>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-1 to Compound 2-8 was used instead of Compound 1-1 in Example 1.

< Example  21 to Example  27>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3-1 to Compound 3-7 was used instead of Compound 1-1 in Example 1.

< Example  28 to Example  35>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4-1 to Compound 4-8 was used instead of Compound 1-1 in Example 1.

< Comparative example  1 to Comparative example  16>

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following H-1 to H-16 instead of the compound 1-1 in Example 1.

The organic light emitting diodes manufactured according to Examples 1 to 35 and Comparative Examples 1 to 16 measured driving voltage and luminous efficiency at a current density of 10 mA / cm ² , and compared to initial luminance at a current density of 20 mA / cm ² . The time to become% (T98) was measured. In addition, the emission color was measured at 5,000 nit brightness. The results are shown in Table 1 below.

TABLE 1

As shown in Table 1, in the case of an organic light emitting device manufactured by using the compound represented by Formula 1 of the present specification as a light emitting layer, compared to Comparative Examples 1 to 16, excellent characteristics in light efficiency, driving voltage and / or stability It can be seen that represents. In particular, Examples 1 to 35 using the compound represented by the formula (1) of the present specification, it can be seen that the life characteristics improved more than two times, compared to Comparative Examples 1 to 16.

Specifically, when Ar 1 of Formula 1 of the present specification is a bicyclic or more heterocyclic group containing 2 or more of N, lower driving than in the case of an aryl group as in Comparative Example 1, Comparative Example 5, Comparative Example 9 and Comparative Example 13 It can be seen that it has the characteristics of voltage, high light efficiency and long life. In addition, in the case of a monocyclic heterocyclic group as in Comparative Examples 2 to 4, Comparative Examples 6 to 8, Comparative Examples 10 to 12, and Comparative Examples 14 to 16, Ar 1 in Formula 1 of the present specification includes two or more N rings. In the case of the heterocyclic group, the driving voltage and the light efficiency characteristics are similar, but it can be seen that the service life characteristics are remarkably inferior.

Although the preferred embodiments of the present specification have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention. Belongs to.

10, 11: organic light emitting element
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer

Claims (10)

A compound represented by any one of the following formulas (2) to (4):
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,
L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R1 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R14 is hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a is an integer from 1 to 4,
when a is 2 or more, two or more R14 are each the same as or different from each other,
Ar1 is any one selected from the following structures,

In the above structure,
Ar ₂ to Ar ₇ are the same as or different from each other, and each independently hydrogen; Alkyl groups; An aryl group unsubstituted or substituted with an alkyl group; Or a heterocyclic group unsubstituted or substituted with an aryl group,
r ₂ is an integer of 1 to 5,
r ₃ is an integer of 1 to 4,
r ₄ is an integer of 1 to 3,
r7 is an integer of 1 to 7,
When r ₂ to r ₄ and r ₇ are each 2 or more, two or more Ar ₂ to Ar ₄ and Ar ₇ are the same as or different from each other. delete delete The compound of claim 1, wherein Formulas 2 to 4 are any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to claim 1 or 4. The organic light emitting diode of claim 5, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The organic light emitting device of claim 5, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The organic light emitting device of claim 5, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the compound. The organic light emitting device of claim 5, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound. The method according to claim 5, wherein the organic light emitting device further comprises one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer. Phosphorescent organic light-emitting device.

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