KR20180099539A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, and to an organic light emitting device comprising the same. The compound according to one embodiment of the present specification can lower the driving voltage of an organic electronic device by being used in the organic light emitting device.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic light-

This specification claims the benefit of Korean Patent Application No. 10-2017-0025637 filed on Feb. 27, 2017, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

An organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

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

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

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

Ar 1 is a substituted or unsubstituted, two or more ring heterocyclic group containing 2 or more N,

R1 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a ring.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

The compound according to one embodiment of the present disclosure can be used in an organic light emitting device to lower the driving voltage of the organic electronic device.

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

In addition, the compound according to one embodiment of the present invention is used in an organic light emitting device, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

1 shows an organic light emitting device 10 according to an embodiment of the present invention.
2 shows an organic light emitting element 11 according to another embodiment of the present invention.

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

The present invention provides a compound represented by the above formula (1).

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

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An amine group; Silyl group; Phosphine oxide groups; An aryl group; And a heteroaryl group containing at least one of N, O, S, Se and Si atoms, or wherein at least two of the substituents exemplified above are substituted with a substituent to which they are connected, Quot; means < / RTI >

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, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, and more preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms. Specific examples thereof include 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 are not limited thereto.

In the present specification, the silyl group is a substituent group containing Si and the Si atom is directly connected as a radical and is represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , R ₂₀₁ to R ₂₀₃ are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. 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 50 carbon atoms, and more preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. Preferably 10 to 50 carbon atoms, and more preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.

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

,

,

,

,

,

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

,

,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heteroatom and includes at least one of N, O, S, Si and Se. The number of carbon atoms 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 a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, A pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pteridine group, a pyrido pyrimidine group, a pyrido pyrazine group A pyrazino pyrazine group, an isoquinoline group group, an indole group, a pyrido indole group, a 5H-indeno pyrimidine group, a carbazole group, a benzoxazole group, a benzimidazole group, Benzothiazole group, benzothiazole group, benzothiazole group, benzothiophene group, dibenzothiophene group, benzofurane group, dibenzofurane group, phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, A thiazolyl group, and the like, but are not limited thereto.

In the present specification, the heteroaryl group may be selected from the 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, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

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

In one embodiment of the present disclosure, 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 represents 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 phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenylene group.

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

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

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted two or more ring heterocyclic group containing 2 or more N.

, 또는 치환 또는 비치환된

이다. In one embodiment of the present specification, Ar 1 is a substituted or unsubstituted quinazoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted phthalazine group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted quinazoline group, A substituted or unsubstituted pyridopyrimidine group, a substituted or unsubstituted pyridopyrimidine group, a substituted or unsubstituted pyridopyrimidine group, a substituted or unsubstituted pyrazino pyridine group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted pyridoindole group, An unsubstituted indenopyrimidine group, a substituted or unsubstituted

, Or a substituted or unsubstituted

to be.

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

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

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

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

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

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

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

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

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

In one embodiment of the present invention, Ar1 is a pyridoindole group substituted or unsubstituted 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 an indenopyrimidine group substituted or unsubstituted with an aryl group.

In one embodiment of the present invention, Ar1 is an indenopyrimidine group substituted or unsubstituted 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 .

이다.In one embodiment of the present specification, Ar < 1 > is a substituted or unsubstituted aryl group

to be.

이다. In one embodiment of the present specification, Ar 1 is a substituted or unsubstituted aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, triphenyl, phenanthryl, fluorenyl, or dimethylfluorenyl group

to be.

이다.In one embodiment of the present specification, Ar < 1 > is a substituted or unsubstituted aryl group

to be.

이다. In one embodiment of the present specification, Ar 1 is a substituted or unsubstituted aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, triphenyl, phenanthryl, fluorenyl, or dimethylfluorenyl group

to be.

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

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

In one embodiment of the present specification, Ar 1 is a quinoxaline group substituted or unsubstituted with a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a dibenzofurane group.

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

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

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

In one embodiment of the present specification, Ar1 is a carbazolyl group, a carbazolyl group substituted with a phenyl group, a dibenzothiophene group, or a substituted or unsubstituted pyridinyl group with a dibenzofurane group.

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

In one embodiment of the present specification, Ar1 is a carbazolyl group, a carbazolyl group substituted with a phenyl group, a dibenzothiophen group, or a pyridopyrimidine group substituted or unsubstituted with a dibenzofurane group.

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

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

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

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

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

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

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

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

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

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

이다.In one embodiment of the present specification, Ar < 1 > is a substituted or unsubstituted heterocyclic group

to be.

이다.In one embodiment of the present specification, Ar 1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a substituted or unsubstituted dibenzofurane group

to be.

이다.In one embodiment of the present specification, Ar < 1 > is a substituted or unsubstituted heterocyclic group

to be.

이다.In one embodiment of the present specification, Ar 1 is a carbazole group, a carbazole group substituted with a phenyl group, a dibenzothiophene group, or a substituted or unsubstituted dibenzofurane 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 disclosure, Ar2 to Ar7 are independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

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

In one embodiment of the present specification, Ar 2 to Ar 7 are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms.

In one embodiment of the present invention, Ar 2 to Ar 7 are selected from the group consisting of a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted isopropyl Or a substituted or unsubstituted tert-butyl group.

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

In one embodiment of the present specification, Ar 2 to Ar 7 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

In one embodiment of the present invention, Ar 2 to Ar 7 are selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, A triphenyl group, a substituted or unsubstituted naphthyl group, or a 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 disclosure, R 1 to R 13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R 1 to R 4 may combine with adjacent groups to form a ring.

In one embodiment of the present specification, R 1 and R 2 may combine with each other to form a ring.

In one embodiment of the present disclosure, R 2 and R 3 may combine with each other to form a ring.

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

In one embodiment of the present disclosure, R5 through R13 are each hydrogen.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

L, Ar 1 and R 1 to R 13 are the same as defined in the above formula (1).

In one embodiment of the present disclosure, R14 is selected from the group consisting of hydrogen; heavy hydrogen; A 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; Or a substituted or unsubstituted heterocyclic 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 R < 14 > s are the same or different from each other.

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

In one embodiment of the present invention, the formula (1) is any one selected from the following compounds.

The compound according to one embodiment of the present specification can be produced by a production method described below. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

For example, the compound represented by Formula 1 may have a core structure as shown in Formula 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art. A substituent may be bonded as shown in the following general formula (1), but is not limited thereto.

≪ General Formula 1 &

In the general formula (1), Ar1 and L are the same as defined in the general formula (1).

The compound represented by the above formula (1) can be prepared as described above using Suzuki coupling, Buckwald-Hartwig coupling or the like, but is not limited thereto.

The present invention also provides an organic light emitting device comprising the above-described compound.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is understood that it may include other components as well, without departing from the other components unless specifically stated otherwise.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic light emitting device in this specification, an 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 injecting layer, an electron blocking 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 invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).

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

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

In one embodiment of the present invention, the organic material layer contains the compound represented by the formula (1) as a host in the light emitting layer, and includes another organic compound, metal or metal compound as a dopant.

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

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

In one embodiment of the present invention, 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 represented by the above formula (1).

In one embodiment of the present invention, the organic 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 the above formula (1).

In one embodiment of the present invention, 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 the above formula (1).

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, A light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and an electron blocking layer.

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

Hereinafter, the organic light emitting device will be described.

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

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

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

In addition, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

In one embodiment of the present invention, the organic material layer includes two or more layers of the hole transporting layer, and at least one of the two or more hole transporting layers includes the above compound. Specifically, in one embodiment of the present invention, the compound may be contained in one of the two or more hole transporting layers, and may be included in each of the two or more hole transporting layers.

In addition, in the embodiment of the present specification, when the compound is contained in each of the two or more hole transporting layers, the materials other than the above compounds may be the same or different.

In one embodiment of the present invention, the organic material layer may further include a hole injecting layer or a hole transporting layer containing a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic compound layer containing the compound.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

When the organic compound layer containing the compound represented by Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. For example, the electron transport layer containing the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).

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

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates a structure of an organic light emitting diode 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 embodiment of the present invention, and may further include another organic layer.

2 shows a structure in which a first electrode 30, a hole injecting layer 60, a hole transporting layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transporting layer 90, 100 and a second electrode 50 are sequentially laminated on a transparent substrate 100. In this case, 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound, i.e., the compound represented by the above formula (1).

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

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the organic material layer, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, 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 a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the positive electrode 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), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO2 / Al, but the present invention is not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, examples of aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and peripherrhene having an arylamine group. The styrylamine compound is a compound in which substituted or unsubstituted arylamine is substituted with at least one aryl vinyl group, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group, The substituent is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complexes include iridium complexes, platinum complexes, and the like, but are not limited thereto.

In the present specification, when the compound represented by Chemical Formula 1 is contained in an organic material layer other than the light emitting layer, or a further light emitting layer is provided, the light emitting material of the light emitting layer may be formed by transporting holes and electrons from the hole transporting layer and the electron transporting layer, As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. It is preferable that the hole injecting material has a hole injecting effect in the anode and an excellent hole injecting effect in the light emitting layer or the light emitting material due to its ability to transport holes. Further, a material having excellent ability to prevent migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Further, a material having excellent thin film forming ability is preferable. It is also preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials; Hexanitrile hexaazatriphenylene based organic materials; Organic materials of quinacridone series; Perylene organic materials; And polythiophene-based conductive polymers such as anthraquinone and polyaniline, but the present invention is not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emission 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 and having high mobility to holes is preferable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but the present invention is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emission layer. As the electron transporting material, a material capable of injecting electrons from the cathode well and transferring the electrons to the light emitting layer is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material, as used according to the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, which are in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injecting material preferably has an excellent ability to transport electrons, has an electron injecting effect from the cathode, and has an excellent electron injecting effect with respect to the emitting layer or the light emitting material. Further, it is preferable that the exciton generated in the light emitting layer is prevented from moving to the hole injection layer, and the material having the excellent film forming ability is excellent. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, pre-phenylidenemethane, Metal complex compounds and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h ] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) , But is not limited thereto.

The electron blocking layer is a layer that can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, thereby improving the lifetime and efficiency of the device. A known material can be used without limitation, and it can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer that simultaneously performs hole injection and hole transport.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

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

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

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

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Manufacturing example >

< Manufacturing example  1. Preparation of Formulas A-1 to A-4 &gt;

(1) Preparation of the compound of formula A-1

4-bromoindolo [3,2,1-jk] carbazole 300.0 g (1.00 eq), ((2-nitrophenyl) boronic acid) 172.04 g (1.1 eq) and Pd (PPh _{3) 4} to 10.82 g (0.01 eq) in anhydrous Was 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, which was then refluxed and stirred. After 2 hours, when the reaction was completed, the organic layer was separated, and the solvent was removed by decompression. The product was completely dissolved in CHCl ₃ and washed with water. The solution was concentrated under reduced pressure to about 50%, ethanol was added thereto, and crystals were dropped and filtered. Thereafter, purification was carried out using column chromatography to obtain 288.61 g (yield: 85%) of the compound B-1. MS [M + H] &lt; ⁺ &gt; = 363

288.61 g (1.0 eq) of Compound 1-1 was dissolved in 1 L of triethylphosphite (P (OEt) ₃ ), refluxed and stirred. After 3 hours, the reaction was terminated by vacuum decompression to remove about 50% of the solvent, which was then cooled to room temperature and filtered. After completely dissolved in ethyl acetate and washed with water, the solution was concentrated under reduced pressure to about 70%, cooled to room temperature, and filtered to obtain 184.18 g (yield 70%) of Compound A-1. MS [M + H] &lt; ⁺ &gt; = 331

(2) Preparation of compound of formula A-2

Compound A-2 was obtained in the same manner as in the preparation of Compound A-1 except that (2-nitronaphthalen-1-yl) boronic acid was used instead of 2-nitrophenyl boronic acid.

(3) Preparation of compound of formula A-3

Compound A-3 was obtained in the same manner as in the preparation of Compound A-1 except that (3-nitronaphthalen-2-yl) boronic acid was used instead of 2-nitrophenyl boronic acid.

(4) Preparation of compound of formula A-4

Compound A-4 was obtained in the same manner as in the preparation of Compound A-1 except that (1-nitronaphthalen-2-yl) boronic acid was used instead of 2-nitrophenyl boronic acid.

< Manufacturing example  2. Preparation of compounds 1-1 to 1-12 &gt;

(1) Production 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were added to 300 mL of xylene and the mixture was refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The product was purified by column chromatography to obtain 12.38 g (yield 70%) of Compound 1-1. MS [M + H] &lt; ⁺ &gt; = 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) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 13.8 g (yield 69%) of Compound 1-2. MS [M + H] &lt; ⁺ &gt; = 661

(3) Preparation of Compound 1-3

13.51 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1.0 eq), 3- (2-chloroquinazolin-4-yl) 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. This was purified by column chromatography to obtain 15.03 g (yield 73%) of Compound 1-3. MS [M + H] &lt; ⁺ &gt; = 700

(4) Preparation of compounds 1-4

11.01 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1 eq), 10.0 g (1.0 eq) of compound A- 1, 2-chloro-4- (naphthalen- 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again decompressed to remove the solvent. This was purified by column chromatography to obtain 13.23 g (yield 70%) of Compound 1-4. MS [M + H] &lt; ⁺ &gt; = 625

(5) Preparation of compounds 1-5

Dibenzo [b, d] furan-3-yl) -5,5-dimethyl-5H-indeno [1,2-d] pyrimidine A mixture of 10.0 g (1.0 eq) of Compound A- (1.1 eq), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were added to 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 15.26 g (yield 73%) of Compound 1-5. MS [M + H] &lt; ⁺ &gt; = 691

(6) Preparation of compound 1-6

Compound A-1 15.08 g (1.1 eq) of 10.0 g (1.0 eq) of 2-chloro-4- (9-phenyl-9H- carbazol- 2- yl) benzo [4,5] thieno [3,2- ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The solution was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 15.56 g (yield: 68%) of Compound 1-6. MS [M + H] &lt; ⁺ &gt; = 756

(7) Production 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 11.86 g (yield 67%) of Compound 1-7. MS [M + H] &lt; ⁺ &gt; = 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ and washed with water. The reaction solution was further reduced in pressure to remove the solvent and purified by column chromatography to obtain 13.44 g (yield 70%) of Compound 1-8. MS [M + H] &lt; ⁺ &gt; = 635

(9) Preparation of compound 1-9

13.08 g (1.1 eq) of Pd (t-Bu ₃ P), 10.08 g (1.0 eq) of Compound A-1, 6,11- ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The solution was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 14.76 g (yield: 71%) of Compound 1-9. MS [M + H] &lt; ⁺ &gt; = 687

(10) Preparation of compounds 1-10

17.89 g (1.1 eq) of Pd (t-Bu ₃ P (1 eq)), 10.0 g (1.0 eq) of compound A-1, 2- (4-bromonaphthalen- ) ₂ 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The residue was purified by column chromatography to obtain 14.96 g (yield: 68%) of Compound 1-10. MS [M + H] &lt; ⁺ &gt; = 727

(11) Preparation of Compound 1-11

14.41 g (1.1 eq) of Pd (t-Bu ₃ P (1 eq)), 10.0 g (1.0 eq) of compound A-1, 2-chloro-4- ) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 14.96 g (yield 68%) of Compound 1-11. MS [M + H] &lt; ⁺ &gt; = 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 13.59 g (yield 69%) of Compound 1-12. MS [M + H] &lt; ⁺ &gt; = 651

< Manufacturing example  3. Preparation of compounds 2-1 to 2-8 &gt;

(1) Production of Compound 2-1

A solution of 11.18 g (1.1 eq) of Pd (t-Bu ₃ P (1 eq)) was added to 10.0 g (1.0 eq2-chloro-4- (dibenzo [b, d] thiophen- ) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ and washed with water. The reaction solution was further reduced in pressure to remove the solvent and purified by column chromatography to obtain 13.25 g (yield 69%) of Compound 2-1. MS [M + H] &lt; ⁺ &gt; = 731

(2) Preparation of Compound 2-2

A solution of 10.0 g (1.0 eq. 2-chloro-5,5-dimethyl-4- (9-phenyl-9H-carbazol-2-yl) -5H- indeno [1,2- d] pyrimidine 13.64 g ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 15.87 g (yield 74%) of Compound 2-2. MS [M + H] &lt; ⁺ &gt; = 816

(3) Preparation of Compound 2-3

4-yl) benzo [4,5] thieno [3,2-d] pyrimidine 11.18 g (1.1 eq) of Compound A-2 (1.0 eq), 2-chloro-4- ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 13.44 g (yield 70%) of Compound 2-3. MS [M + H] &lt; ⁺ &gt; = 731

(4) Preparation of compound 2-4

11.01 g (1.1 eq) of Pd (t-Bu ₃ P), 10.0 g (1.0 eq) of 3-chloro-1- (dibenzo [b, d] furan- ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 13.90 g (yield 73%) of Compound 2-4. MS [M + H] &lt; ⁺ &gt; = 725

(5) Preparation of compound 2-5

A mixture of 10.0 g (1.0 eq) of compound A-2, 9.18 g (1.1 eq) of 3- (4-chlorophenyl) -2-phenylpyrido [₃P)₂ 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and the xylene was removed by decompression. CHCl3₃And the solvent was removed under reduced pressure. The solvent was then removed and purified by column chromatography to obtain 12.53 g (yield 72%) of Compound 2-5. MS [M + H] &lt;⁺= 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, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 11.25 g (yield 73%) of Compound 2-6. MS [M + H] &lt; ⁺ &gt; = 587

(7) Preparation of compound 2-7

14.09 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1.0 eq), 4- (4-bromophenyl) -2- (naphthalen- 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was removed again under reduced pressure, and the residue was purified by column chromatography to obtain 14.68 g (yield 71%) of Compound 2-7. MS [M + H] &lt; ⁺ &gt; = 787

(8) Production 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 13.67 g (yield 73%) of Compound 2-8. MS [M + H] &lt; ⁺ &gt; = 713

< Manufacturing 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The product was purified by column chromatography to obtain 13.26 g (yield 72%) of Compound 3-1. MS [M + H] &lt; ⁺ &gt; = 701

(2) Preparation of compound 3-2

12.89 g (1.1 eq) of Pd (t-butoxycarbonyl) benzofuro [3,2-d] pyrimidine, 10.0 g (1.0 eq) of Compound A- This is ₃ P) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 14.53 g (yield 70%) of Compound 3-2. MS [M + H] &lt; ⁺ &gt; = 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The residue was purified by column chromatography to obtain 12.80 g (yield 67%) of Compound 3-3. MS [M + H] &lt; ⁺ &gt; = 727

(4) Preparation of compound 3-4

13.51 g (1.1 eq) of Pd (t), 10.0 g (1.0 eq) of 2- (4-bromonaphthalen- 1 -yl) -4-phenylbenzo [4,5] thieno [3,2- -Bu ₃ P) ₂ 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 15.52 g (yield: 77%) of 3-4. MS [M + H] &lt; ⁺ &gt; = 767

(5) Preparation of compound 3-5

8.73 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1 eq), 10.0 g (1.0 eq) of compound A-3, 4-chloro-2- (naphthalen- 0.07 g (0.005 eq)? 12.85 g (2.0 eq) of K ₃ PO ₄ was added to 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again decompressed to remove the solvent. This was purified by column chromatography to obtain 11.52 g (yield 69%) of Compound 3-5. MS [M + H] &lt; ⁺ &gt; = 636

(6) Preparation of compound 3-6

12.67 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1.0 eq), 2- (4-bromophenyl) -4,6-diphenylpyrido [ 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was removed again under reduced pressure, and the residue was purified by column chromatography to obtain 11.83 g (yield: 61%) of Compound 3-6. MS [M + H] &lt; ⁺ &gt; = 738

(7) Preparation of compound 3-7

13.93 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1 eq), 10.0 g (1.0 eq) of Compound A-3, 2- (3-chloro-6-phenylquinoxalin- 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. This was purified by column chromatography to obtain 14.54 g (yield 67%) of Compound 3-7. MS [M + H] &lt; ⁺ &gt; = 826

< Manufacturing example  5. Preparation of compounds 4-1 to 4-8 &gt;

(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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was removed again under reduced pressure, and the residue was purified by column chromatography to obtain 11.06 g (yield 72%) of Compound 4-1. MS [M + H] &lt; ⁺ &gt; = 585

(2) Preparation of compound 4-2

13.33 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (0.1 eq), 2- (4-bromonaphthalen- 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 14 g (yield 70%) of Compound 4-2. MS [M + H] &lt; ⁺ &gt; = 761

(3) Preparation of compound 4-3

10.47 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (1.0 eq), 2- (4-bromophenyl) -3-phenylpyrido [ 0.07 g (0.005 eq) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 11.83 g (yield: 68%) of compound 4-3. MS [M + H] &lt; ⁺ &gt; = 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) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was removed again under reduced pressure, and the residue was purified by column chromatography to obtain 11.10 g (yield 72%) of Compound 4-4. MS [M + H] &lt; ⁺ &gt; = 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) of NaOtBu and 5.82 g (2.0 eq) of NaOtBu were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 13.38 g (yield 69%) of Compound 4-5. MS [M + H] &lt; ⁺ &gt; = 738

(6) Preparation of compound 4-6

11.47 g (1.1 eq) of Pd (t-Bu ₃ P), 10.0 g (1.0 eq) of 3-chloro-1- (dibenzo [b, d] thiophen- ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again decompressed to remove the solvent. The residue was purified by column chromatography to obtain 13.63 g (yield 70%) of Compound 4-6. MS [M + H] &lt; ⁺ &gt; = 741

(7) Preparation of compound 4-7

8.58 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (10 eq), 2-chloro-4-phenylbenzo [4,5] thieno [ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The residue was purified by column chromatography to obtain 10.94 g (yield: 65%) of Compound 4-7. MS [M + H] &lt; ⁺ &gt; = 641

(8) Preparation of compound 4-8

3-yl) benzo [4,5] thieno [3,2-d] pyrimidine A mixture of 10.0 g (1.0 eq) of Compound A-4, 11.18 g (1.1 eq) of 2-chloro-4- (dibenzo [b, ), Pd (t-Bu ₃ P) ₂ 0.07 g (0.005 eq) of K ₃ PO _{4 and} 12.85 g (2.0 eq) of K ₃ PO ₄ were placed in 300 mL of xylene, refluxed and stirred. After 5 hours, the reaction mixture was cooled to room temperature, and then xylene was removed by decompression. The residue was completely dissolved in CHCl ₃ and washed with water. The solvent was then removed under reduced pressure, and the residue was purified by column chromatography to obtain 11.71 g (yield: 61%) of compound 4-8. MS [M + H] &lt; ⁺ &gt; = 731

< Example >

< Example  1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

A hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on the ITO transparent electrode thus prepared to form a thin film.

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

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

The following compound HB-1 was deposited on the light emitting layer to a thickness of 50 Å to form a hole blocking layer. Then, the following compound ET-1 was deposited to a thickness of 310 Å to form an electron transporting layer.

Lithium fluoride (LiF) 12 Å thick and aluminum 1,000 Å thick 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 ^{- 7} to 5 X 10 &lt; ^-6 &gt; torr to obtain an organic light emitting device.

< Example  2 to Example  12>

An organic light emitting device was fabricated 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 - Example  20>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compounds 2-1 to 2-8 were used instead of the compound 1-1 in Example 1.

< Example  21 - Example  27>

An organic luminescent device was fabricated in the same manner as in Example 1 except that the compound 3-1 to the compound 3-7 were used instead of the compound 1-1 in Example 1.

< Example  28 - Example  35>

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 4-1 to the compound 4-8 were used instead of the compound 1-1 in Example 1.

< Comparative Example  1 to Comparative Example  16>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the following H-1 to H-16 were used instead of the compound 1-1 in Example 1.

The Examples 1 to 35 and Comparative Examples 1 to were the organic light emitting device produced by the 16 measurement of driving voltage and luminous efficiency at a current density of 10 mA / cm ^2, the initial luminance compared to 98 at a current density of 20mA / cm ² % (T98) was measured. Further, the luminescent color was measured at a luminance of 5,000 nit. The results are shown in Table 1 below.

[Table 1]

As shown in Table 1, the organic light emitting device manufactured using the compound represented by Formula 1 of the present invention as the light emitting layer exhibited excellent characteristics in terms of light efficiency, driving voltage, and / or stability as compared with Comparative Examples 1 to 16 . &Lt; / RTI &gt; In particular, it can be seen that in Examples 1 to 35 using the compound represented by Chemical Formula 1 of the present invention, the lifetime characteristics were improved to twice or more as compared with Comparative Examples 1 to 16.

Specifically, when Ar1 of formula (1) of the present invention is two or more ring heterocyclic groups containing two or more N atoms, as compared with the case of aryl groups as in Comparative Example 1, Comparative Example 5, Comparative Example 9 and Comparative Example 13, Voltage, high light efficiency, and long life. Further, in the case of the 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, Ar1 in the formula (1) , The driving voltage and the light efficiency characteristics are similar to each other, but the lifetime characteristics are remarkably inferior.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

10, 11: Organic light emitting device
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 the following formula (1):
[Chemical Formula 1]

In Formula 1,
L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar 1 is a substituted or unsubstituted, two or more ring heterocyclic group containing 2 or more N,
R1 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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; Or a substituted or unsubstituted heterocyclic group,
The R1 to R4 may combine with adjacent groups to form a ring. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (2) to (4)
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
L, Ar 1 and R 1 to R 13 are the same as defined in Formula 1,
R14 is hydrogen; heavy hydrogen; A 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; Or a substituted or unsubstituted heterocyclic group,
a is an integer of 1 to 4,
When a is 2 or more, two or more R &lt; 14 &gt; s are the same or different from each other. 2. The compound according to claim 1, wherein Ar is any one selected from the following structures:

In the above structure,
Ar2 to Ar7 represent hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
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,
When r2 to r4 and r7 are each 2 or more, two or more of Ar2 to Ar4 and Ar7 are the same or different from each other. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 4. The organic light- Light emitting element. The organic light emitting device according to claim 5, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. [6] The organic light emitting device according to claim 5, wherein the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The organic light emitting device according to 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 comprises the compound. The organic light emitting device according to 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 comprises the compound. [Claim 6] The organic electroluminescent device of claim 5, wherein the organic light emitting device comprises a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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