KR101780595B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a heterocyclic compound and an organic light emitting device using the heterocyclic compound.

Description

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

This specification claims the benefit of Korean Patent Application No. 10-2013-0116336, filed on September 30, 2013, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present invention relates to heterocyclic compounds and organic light emitting devices containing them.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

Therefore, there is a need in the art to develop new organic materials.

Korean Patent Publication No. 2007-0092667

It is an object of the present invention to provide a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

In one embodiment of the present specification, there is provided a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In formula (1)

X is CRR 'or O,

n is an integer of 0 to 2,

When n is 2, X is the same or different,

R1 to R8, R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, the first electrode; A second electrode facing the first electrode; And an organic layer formed of one or more layers including a light emitting layer provided between the first electrode and the second electrode,

Wherein at least one of the organic material layers comprises a heterocyclic compound represented by the above formula (1).

The heterocyclic compound according to one embodiment of the present specification has an appropriate energy level, and is excellent in electrochemical stability and thermal stability. Thus, the organic light emitting device comprising the compound provides high efficiency and / or high driving stability.

1 to 5 are cross-sectional views illustrating the structure of an organic light emitting device according to an embodiment of the present invention.
6 shows the formula (1) representing the heterocyclic compound of the present specification.

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

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is provided.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; Thiol group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; An aryl group; Arylalkyl groups; An arylalkenyl group; And a heterocyclic group, or that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent to which they are linked. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

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

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

In the present specification, an amide group may be mono- or di-substituted with nitrogen of an amido group with hydrogen, a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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. 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, N-octyl, 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 specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted. In addition, an aryl group in the present specification may mean an aromatic ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a stilbenyl group.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 60 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

,

,

및

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

,

,

And

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

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of O, N, S, Se and Si, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the aryl sulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group, but the present invention is not limited thereto.

In the present specification, the alkyloxy group, the alkyl group in the alkylsulfoxy group, can be applied to the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, But the present invention is not limited thereto.

In the present specification, the substituted or unsubstituted heterocyclic group includes a substituted or unsubstituted aromatic or aliphatic heterocyclic group.

In one embodiment of the present specification, at least one of R6 to R8 is a substituted or unsubstituted aryl group.

When the total molecular weight excluding R6 to R8 is less than 400, the Tg of the substance may be low. In order to improve the low Tg, when at least one of R 6 to R 8 according to one embodiment of the present invention is a substituted or unsubstituted aryl group, the effect of increasing Tg by increasing the molecular weight is effective

In one embodiment of the present disclosure,

when n is 1, X is O or CRR '

When n is 2, (X) _n is CRR'-CRR 'or O-CRR'

when n = 0; n = 2 and (X) _n is CRR'-CRR '; And when n = 2 and (X) _n is O-CRR '

R1 to R5, R and R 'are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R6 to R8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R8, R and R 'are not simultaneously hydrogen,

When n = 1 and X is O,

R1 is a substituted or unsubstituted aryl group,

R2 to R8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

When n = 1 and X is CRR '

R1 to R8, R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

At least one of R2 to R8 is a substituted or unsubstituted aryl group.

In the present state of implementation,

R1 to R5, R and R 'are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R6 to R8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; An amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2 to R8 are not simultaneously hydrogen.

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

In one embodiment of the present disclosure, X is CRR '.

In one embodiment of the present invention, R and R 'are the same or different and are each independently a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R is a methyl group.

In one embodiment of the present specification, R 'is a methyl group.

In one embodiment of the present disclosure, n is one.

In one embodiment of the present disclosure,

At least one of R1 to R8 is - (L) a- (Y) b,

L is a substituted or unsubstituted arylene,

Y is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 1 to 10, b is an integer of 1 to 10,

when a is 2 or more, L is the same or different from each other,

When b is 2 or more, Y is the same or different from each other.

In one embodiment of the present disclosure,

At least one of R6 to R8 is - (L) a- (Y) b.

In one embodiment of the present invention, R 2 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R 2 is a methyl group.

In one embodiment of the present disclosure, R2 is hydrogen.

In one embodiment of the present invention, R 3 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R 3 is a methyl group.

In one embodiment of the present disclosure, R 3 is hydrogen.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted aryl group.

In one embodiment of the present disclosure, R1 is - (L) a- (Y) b,

L is a substituted or unsubstituted arylene,

Y is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 1 to 10, b is an integer of 1 to 10,

when a is 2 or more, L is the same or different from each other,

When b is 2 or more, Y is the same or different from each other.

In one embodiment of the present specification, L is a substituted or unsubstituted arylene having 1 to 3 rings.

In one embodiment of the present disclosure, L is substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; Substituted or unsubstituted terphenylene; A substituted or unsubstituted stilbenyl group; Substituted or unsubstituted naphthylene; Substituted or unsubstituted anthracenylene; Or substituted or unsubstituted fluorenylenes.

In one embodiment of the present disclosure, L is hydrogen; Phenylene; Biphenylene; Terphenylene; A stilbenyl group; Naphthylene; Anthracenylene; Or fluorenylene.

In one embodiment of the present disclosure, Y is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

In one embodiment of the present invention, Y is selected from the group consisting of hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, Substituted or unsubstituted anthryl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted creicenyl groups, substituted Or an unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present invention, Y is selected from the group consisting of hydrogen, phenyl, biphenyl, terphenyl, stilbenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, An norbornyl group, an oleyl group, a triphenylene group or a heterocyclic group.

In one embodiment of the present invention, Y is selected from the group consisting of hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, Substituted or unsubstituted anthryl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted creicenyl groups, substituted A substituted or unsubstituted thiophene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophene group, or a substituted or unsubstituted heterocycle containing one or more N .

In one embodiment of the present specification, R 1 is an aryl group substituted or unsubstituted with an aryl group; Or an aryl group which is substituted or unsubstituted with a heterocyclic group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted alkyl group; A phenyl group substituted with an aryl group; A naphthyl group substituted with an aryl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted alkyl group; An unsubstituted phenyl group; A phenyl group substituted with a substituted or unsubstituted anthracenyl group; A phenyl group substituted with a substituted or unsubstituted fluorenyl group; A phenyl group substituted with a substituted or unsubstituted pyrenyl group; A phenyl group substituted with a substituted or unsubstituted naphthyl group; A phenyl group substituted with a substituted or unsubstituted terphenyl group; A phenyl group substituted with a substituted or unsubstituted heterocyclic group; A naphthyl group substituted with a substituted or unsubstituted anthracenyl group; A naphthyl group substituted with a substituted or unsubstituted phenyl group; Or a naphthyl group substituted with a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted alkyl group; An unsubstituted phenyl group; A phenyl group substituted with an anthracenyl group; A phenyl group substituted with a fluorenyl group; A phenyl group substituted with a pyrenyl group; A phenyl group substituted with a naphthyl group; A phenyl group substituted with a terphenyl group; A phenyl group substituted with a heterocyclic group; A naphthyl group substituted with an anthracenyl group; A naphthyl group substituted with a phenyl group; Or a naphthyl group substituted with a fluorenyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, a substituted or unsubstituted naphthyl group A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted creicenyl group, Lt; / RTI >

In one embodiment of the present invention, R 1 is a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, or a fluorenyl group to be.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted aryl group having 1 to 3 rings.

In one embodiment of the present invention, R 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted anthracenyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R 1 is an alkyl group; A phenyl group; Naphthyl group; A biphenyl group; Or a terphenyl group.

In one embodiment of the present specification, R 1 is a phenyl group; Naphthyl group; Or an anthracenyl group.

In one embodiment of the present specification, R 1 is a phenyl group; Or a naphthyl group.

In one embodiment of the present specification, R1 is a phenyl group.

In one embodiment of the present specification, R4 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R4 is a methyl group.

In one embodiment of the present disclosure, R4 is hydrogen.

In one embodiment of the present specification, R5 is a substituted or unsubstituted alkyl group.

In one embodiment of the present invention, R5 is a methyl group.

In one embodiment of the present disclosure, R5 is hydrogen.

In one embodiment of the present specification, R 1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R1 is a phenyl group.

In one embodiment of the present invention, R 1 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R 1 is an ethyl group.

In one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R6 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, a substituted or unsubstituted naphthyl group A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted creicenyl group, Lt; / RTI >

In one embodiment of the present invention, R6 is a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, or a fluorenyl group to be.

In one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 1 to 3 rings.

In one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R8 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, a substituted or unsubstituted naphthyl group A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted creicenyl group, Lt; / RTI >

In one embodiment of the present invention, R8 represents a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, or a fluorenyl group to be.

In one embodiment of the present specification, R8 is a substituted or unsubstituted aryl group having 1 to 3 rings.

In one embodiment of the present specification, R8 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R8 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, at least one of R6 to R8 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted aryl group.

In one embodiment of the present disclosure, R7 is - (L) a- (Y) b,

L is a substituted or unsubstituted arylene,

Y is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 1 to 10, b is an integer of 1 to 10,

when a is 2 or more, L is the same or different from each other,

When b is 2 or more, Y is the same or different from each other.

In one embodiment of the present specification, L is a substituted or unsubstituted arylene having 1 to 3 rings.

In one embodiment of the present disclosure, L is substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; Substituted or unsubstituted terphenylene; A substituted or unsubstituted stilbenyl group; Substituted or unsubstituted naphthylene; Substituted or unsubstituted anthracenylene; Or substituted or unsubstituted fluorenylenes.

In one embodiment of the present disclosure, L is selected from the group consisting of phenylene; Biphenylene; Terphenylene; A stilbenyl group; Naphthylene; Anthracenylene; Or fluorenylene.

In one embodiment of the present specification, Y is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

In one embodiment of the present invention, Y is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, a substituted or unsubstituted naphthyl group Substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted chrysenyl groups, substituted or unsubstituted pyranyl groups, substituted or unsubstituted pyrenyl groups, A substituted fluorenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present invention, Y represents a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a crycenyl group, , A triphenylene group or a heterocyclic group.

In one embodiment of the present invention, Y is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, a substituted or unsubstituted naphthyl group Substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted chrysenyl groups, substituted or unsubstituted pyranyl groups, substituted or unsubstituted pyrenyl groups, A substituted or unsubstituted benzenesulfonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophene group, or a substituted or unsubstituted heterocyclic group containing one or more N .

In one embodiment of the present invention, R7 is an aryl group substituted or unsubstituted with an aryl group; Or an aryl group which is substituted or unsubstituted with a heterocyclic group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; A phenyl group substituted with an aryl group; A naphthyl group substituted with an aryl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; An unsubstituted phenyl group; A phenyl group substituted with a substituted or unsubstituted anthracenyl group; A phenyl group substituted with a substituted or unsubstituted fluorenyl group; A phenyl group substituted with a substituted or unsubstituted pyrenyl group; A phenyl group substituted with a substituted or unsubstituted naphthyl group; A phenyl group substituted with a substituted or unsubstituted terphenyl group; A phenyl group substituted with a substituted or unsubstituted phenanthryl group; A phenyl group substituted with a substituted or unsubstituted heterocyclic group; A naphthyl group substituted with a substituted or unsubstituted anthracenyl group; A naphthyl group substituted with a substituted or unsubstituted phenyl group; Or a naphthyl group substituted with a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; An unsubstituted phenyl group; A phenyl group substituted with an anthracenyl group; A phenyl group substituted with a fluorenyl group; A phenyl group substituted with a pyrenyl group; A phenyl group substituted with a naphthyl group; A phenyl group substituted with a terphenyl group; A phenyl group substituted with a phenanthryl group; A phenyl group substituted with a heterocyclic group; A naphthyl group substituted with an anthracenyl group; A naphthyl group substituted with a phenyl group; Or a naphthyl group substituted with a fluorenyl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; A phenyl group substituted with an aryl group; A naphthyl group substituted with an aryl group; A phenyl group substituted with a heterocyclic group; Or a naphthyl group substituted with a heterocyclic group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; An unsubstituted phenyl group; A phenyl group substituted with a substituted or unsubstituted anthracenyl group; A phenyl group substituted or unsubstituted with a substituted or unsubstituted fluorenyl group; A phenyl group substituted or unsubstituted with a substituted or unsubstituted pyrenyl group; A phenyl group substituted or unsubstituted with a substituted or unsubstituted naphthyl group; A phenyl group substituted or unsubstituted with a substituted or unsubstituted terphenyl group; A phenyl group substituted with a substituted or unsubstituted phenanthryl group; A naphthyl group substituted with a substituted or unsubstituted anthracenyl group; A naphthyl group substituted with a substituted or unsubstituted phenyl group; Or a naphthyl group substituted or unsubstituted with a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; An unsubstituted phenyl group; A phenyl group substituted with an anthracenyl group; A phenyl group substituted or unsubstituted with a fluorenyl group; A phenyl group substituted or unsubstituted with a pyrenyl group; A phenyl group substituted or unsubstituted with a naphthyl group; A phenyl group substituted or unsubstituted with a terphenyl group; A naphthyl group substituted with a substituted or unsubstituted anthracenyl group; A naphthyl group substituted with a phenyl group; Or a naphthyl group substituted or unsubstituted with a fluorenyl group.

In one embodiment of the present specification, R7 is an anthracenyl group substituted or unsubstituted with a substituted or unsubstituted biphenyl group; An anthracenyl group substituted or unsubstituted with a substituted or unsubstituted phenyl group; Or a phenyl group substituted or unsubstituted with a substituted or unsubstituted phenanthryl group.

In one embodiment of the present specification, R7 is an anthracenyl group substituted or unsubstituted with an aryl group; Or a phenyl group substituted or unsubstituted with an aryl group.

In one embodiment of the present invention, R7 is an anthracenyl group substituted or unsubstituted with a biphenyl group; Anthracenyl group substituted or unsubstituted with a phenyl group; Or a phenyl group substituted or unsubstituted with a phenanthryl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilbenyl group, a substituted or unsubstituted naphthyl group A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted creicenyl group, Lt; / RTI >

In one embodiment of the present disclosure, R7 is a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, or a fluorenyl group to be.

In one embodiment of the present specification, R7 is a substituted or unsubstituted aryl group having 1 to 3 rings.

In one embodiment of the present specification, R7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R7 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted anthracenyl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

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

In one embodiment of the present specification, R7 is an alkyl group; A phenyl group; Naphthyl group; A biphenyl group; Or a terphenyl group.

In one embodiment of the present specification, R7 is a phenyl group; Naphthyl group; Or an anthracenyl group.

In one embodiment of the present specification, R7 is a phenyl group; Or a naphthyl group.

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

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

In one embodiment of the present specification, R7 is a phenyl group substituted with a phenanthryl group.

In one embodiment of the present specification, R7 is a substituted or unsubstituted anthracenyl group.

In one embodiment of the present specification, R7 is an anthracenyl group substituted with a biphenyl group.

In one embodiment of the present invention, the heterocyclic compound represented by the formula (1) is represented by any one of the following formulas 1-1 to 1-102.

In one embodiment of the present disclosure, a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes, wherein the hole injecting layer, the hole transporting layer, or the layer simultaneously injecting holes and transporting holes, ≪ / RTI >

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, And the above heterocyclic compound.

The heterocyclic compound according to one embodiment of the present invention has a planar structure characteristic superior to that of the heterocyclic compound substituted with an aryl group as shown in FIG. This planarity improves the overlapping effect of molecules, which improves the electron mobility and thus enables a low-voltage device. When used in an electron transporting layer, an electron injecting layer, or a layer which simultaneously transports electrons and injects electrons, the electron mobility is improved and the low voltage characteristics are excellent.

In one embodiment of the present invention, the electron transporting layer, the electron injection layer, or the layer which simultaneously transports electrons and electron injection contains only the heterocyclic compound.

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and electrons injects the heterocyclic compound as a p-type host and includes an n-type dopant as a dopant.

In one embodiment of the present disclosure, the n-type dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound, or a combination thereof.

In one embodiment of the present disclosure, the n- type dopant is Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li ₂ O , CsF, or one or more selected from the group consisting of the following compounds.

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In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound.

In one embodiment of the present invention, the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant.

The heterocyclic compound according to one embodiment of the present invention is superior in planar structure characteristics to the heterocyclic compound substituted with an aryl group. This planarity improves the overlapping effect of molecules, which improves the electron mobility and thus enables a low-voltage device. Due to the improved electron mobility, the n-type characteristics in the bipolar host can be improved when used in the light emitting layer.

In one embodiment of the present invention, the phosphorescent dopant compound is represented by the following general formula (4).

[Chemical Formula 4]

In Formula 4,

M ₁ is Ir or Os,

L ₁₀ , L ₁₁ and L ₁₂ are the same or different and independently of each other are any one of the following structures,

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And

d ', f', g ', h', j, j ', and q', p, q, q ', r, s, t, u', v ', w', x ', a, b', c ' k is an integer of 0 to 4,

each of r ', s', t', u, v, w, x, y, y 'and e'

b, e, h, i, k 'and 1 are integers of 0 to 3,

c and g 'each represent an integer of 0 to 2,

f 'is an integer of 0 to 5,

z is an integer of 0 to 8,

R ₁₀ to R ₆₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted C ₂ -C ₁₀ alkylsilyl group; A substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C ₁ ~ C _10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; A substituted or unsubstituted C ₁ to C ₁₀ alkoxy group; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or adjacent groups form a condensed ring of a monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic ring.

In one embodiment of the present invention, the phosphorescent dopant compound represented by Formula 4 is any one of the following compounds.

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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, the organic light emitting device in this specification may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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.

 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 according to the present invention is illustrated in FIGS.

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

2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 shows a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

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 includes the compound of the present invention, i.e., the heterocyclic compound.

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, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and 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.

In addition, the heterocyclic compound may be formed into an organic material 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 one embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.

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

The substrate can be selected in consideration of optical properties and physical properties as required. For example, the substrate is preferably transparent. The substrate may be of a rigid material, but may also be of a flexible material such as plastic.

In addition to glass and quartz, the material of the substrate may be selected from the group consisting of polyethyleneterephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (acrylonitrile butadiene styrene copolymer), TAC (triacetyl cellulose) and PAR (polyarylate), but are not limited thereto.

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 LiO ₂ / Al, but are not limited thereto.

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 cathode material that can be used in the present invention 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); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. The hole injecting material preferably has a highest occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic material, phthalocyanine derivative, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, Perylene-based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are 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 derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; 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, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, 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 injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

In one embodiment of the present invention, the organic light emitting diode may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The heterocyclic compound represented by Formula 1 or Formula 2 and the organic light emitting device including the same will be described in detail below. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

The compound of formula (1) may be prepared based on the preparation examples described below.

<Preparation Example 1> Preparation of [Chemical Formula 1-1]

[Compound A- 1]  Produce

2-amino-3-nitrophenol (30 g, 195 mmol) was dissolved in 500 mL of DMF solution and 80 g of K ₂ CO ₃ was added. After raising the temperature to 100 ° C, 1,2-dibromoethane (36.6 g, 195 mmol) was slowly added dropwise and stirred for 4 hours. After cooling filtration, DMF was distilled, dissolved in 200 mL of EA, and worked up with water (H ₂ O). After the EA layer was extracted, 50 g of MgSO _{4 was} added and stirred, followed by filtration and distillation. The product was purified by column chromatography to obtain [Compound A-1] (16.8 g, yield 48%).

MS: [M + H] &lt; + &gt; = 181

[Compound A- 2]  Produce

After dissolving [Compound A-1] (16.8 g, 93.3 mmol) and 4-bromobenzaldehyde (19.0 g, 103 mmol) in 300 mL of ethanol, 19 g of Na ₂ S ₂ O ₅ was dissolved in 50 mL of water After the addition, the mixture was refluxed for 6 hours. After cooling, 500 mL of water was added and the precipitated solid was filtered. The filtered solid was purified by column chromatography to obtain [Compound A-2] (19.7 g, yield 67%).

MS: [M + H] &lt; + &gt; = 315

[Chemical Formula 1- 1]  Produce

(10-phenylanthracen-9-yl) boronic acid (9.9 g, 33.3 mmol) and THF (100 mL) were charged did. 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.7 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give 10.99 g (yield: 71%) of [Formula 1-1].

MS: [M + H] &lt; + &gt; = 489

<Preparation Example 2> Preparation of [Chemical Formula 1-2]

(10 - ([1,1'-biphenyl] -4-yl) anthracene-9-yl) boronic acid (10 g, 31.7 mmol) biphenyl] -4-yl) anthracen-9-yl) boronic acid (12.5 g, 33.3 mmol) and THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.7 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered and dried to give [Formula 1-2] (13.8, yield 77%).

MS: [M + H] &lt; + &gt; = 565

<Preparation Example 3> Preparation of [Chemical Formula 1-5]

(9,10-diphenylanthracen-2-yl) boronic acid (12.5 g, 33.3 mmol) [Compound A-2] (10 g, 31.7 mmol) , And THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.7 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give [Formula 1-5] (12.5 g, yield 70%).

MS: [M + H] &lt; + &gt; = 565

<Preparation Example 4> Preparation of [Chemical Formula 1-6]

[Compound B- 1]  Produce

2-amino-5-bromo-3-nitrophenol (40 g, 172 mmol, Journal of Medicinal Chemistry, 2008, vol. 51, # 17 p. 5243 5263 Reference) was dissolved in 400 mL of DMF solution, and 71 g of K ₂ CO ₃ was added thereto. After raising the temperature to 100 ° C, 1,2-dibromoethane (32.3 g, 172 mmol) was slowly added dropwise and stirred for 5 hours. After cooling filtration, DMF was distilled, dissolved in 200 mL of EA, and worked up with water (H ₂ O). After extracting the EA layer, 40 g of MgSO _{4 was} added and stirred, followed by filtration and distillation. Purification by column chromatography gave [Compound B-1] (22.3, yield 55%).

MS: [M + H] &lt; + &gt; = 260

[Compound B- 2]  Produce

After dissolving [Compound B-1] (22.3 g, 86 mmol) and 4-bromobenzaldehyde (17.5 g, 94.7 mmol) in 300 mL of ethanol, 19 g of Na ₂ S ₂ O ₅ was dissolved in 50 mL of water After the addition, the mixture was stirred for 6 hours and refluxed. After cooling, 500 mL of water was added and the precipitated solid was filtered. The filtered solid was purified by column chromatography to obtain [Compound B-2] (20.3 g, yield 60%).

MS: [M + H] &lt; + &gt; = 395

Preparation of [Formula 1-6]

(10 - ([1,1'-biphenyl] -4-yl) anthracene-9-yl) boronic acid (15 g, 38.1 mmol) biphenyl] -4-yl) anthracen-9-yl) boronic acid (15.0 g, .0 mmol) and THF (100 mL). 16 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.9 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give [Formula 1-6] (14.0 g, yield 75%).

MS: [M + H] &lt; + &gt; = 489

PREPARATION EXAMPLE 5 Preparation of [Formula 1-9]

[Compound A-2] (10 g, 31.7 mmol) and (9,9-diphenyl-9H-fluoren- 2-yl) boronic acid ) (12.1 g, 33.3 mmol) and THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.7 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give [Formula 1-9] (10.5 g, yield 66%).

MS: [M + H] &lt; + &gt; = 553

PREPARATION EXAMPLE 6 Preparation of [Formula 1-12]

[Compound A-2] (20 g, 63.4 mmol) and 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolen-2-yl) naphthalene -bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalene (12.0 g, 31.7 mmol) and 100 mL of THF. ₂₆ g of K ₂ CO ₃ was dissolved in 50 mL of water and added. It was added a catalytic Pd (PPh _{3) 4} 1.4g was stirred and refluxed for 6 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give 14.8 g (yield 78%) of [Formula 1-12].

MS: [M + H] &lt; + &gt; = 597

PREPARATION EXAMPLE 7 Preparation of [Formula 1-15]

[Compound A-2] (10 g, 31.7 mmol) and 2,4-diphenyl-6- (4- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolene (2,4-diphenyl-6- (4- (7- (4,4,5,5-tetramethyl-1, 2-yl) phenyl) -1,3,5-triazine (17.8 g, 31.7 mmol) and 150 mL of THF were charged. 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.7 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 8 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give 14.4 g (yield 68%) of [Formula 1-15].

MS: [M + H] &lt; + &gt; = 670

PREPARATION EXAMPLE 8 Preparation of [Formula 1-18]

Preparation of [Compound A-3]

Bromo-2-naphthaldehyde (28.7 g, 122 mmol) was dissolved in 300 mL of ethanol, and a solution of Na ₂ S ₂ O ₅ was dissolved in 50 mL of water, and the mixture was refluxed with stirring for 6 hours. After cooling, 500 mL of water was added and the precipitated solid was filtered. The filtered solid was purified by column chromatography to obtain [Compound A-3] (22.3 g, yield 55%).

MS: [M + H] &lt; + &gt; = 366

(9,10-diphenylanthracen-2-yl) boronic acid (12.5 g, 33.3 mmol) was added to a solution of the compound [A- ), And THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. After 0.7 g of the catalyst Pd (PPh ₃ ) ₄ was added, the mixture was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered and dried to give [Formula 1-18] (12.3 g, yield 60%).

MS: [M + H] &lt; + &gt; = 615

PREPARATION EXAMPLE 9 Preparation of [Formula 1-21]

Preparation of [Compound A-4] and [Compound A-5]

The compound [A-4] and [Compound A-5] were separately purified by a column chromatography purification method.

[Compound A-4] (11.2 g, MS: [M + H] &lt; + &gt; = 209)

[Compound A-5] (9.0 g, MS: [M + H] &lt; + &gt; = 209)

Preparation of [Compound A-6]

[Compound A-4] was prepared in the same manner as in [Compound A-2].

MS: [M + H] &lt; + &gt; = 344

Preparation of [Compound A-7]

[Compound A-5] was prepared in the same manner as in [Compound A-2].

MS: [M + H] &lt; + &gt; = 344

Preparation of [Formula 1-21]

(10 g, 29.1 mmol) and (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid ) (10.6 g, 30.6 mmol) and THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 ml of water and then added. It was added a catalytic Pd (PPh _{3) 4} 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered and dried to give 10.6 g (yield, 64%) of [Formula 1-21].

MS: [M + H] &lt; + &gt; = 567

PREPARATION EXAMPLE 10 Preparation of [Formula 1-44]

[Compound A-7] (10 g, 29.1 mmol) and 2- (4- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolen- 2- (4- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2- yl) phenyl) -1,10-phenanthroline (15.6 g, 30.6 mmol) and 150 mL of THF. 15 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. It was added a catalytic Pd (PPh _{3) 4} 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give 8.5 g (yield: 45%) of [Formula 1-44].

MS: [M + H] &lt; + &gt; = 645

PREPARATION EXAMPLE 11 Preparation of [Formula 1-76]

After dissolving 1-amino-2-methyl-2-propanol (17.3 g, 134.0 mmol) in tetrahydrofuran, carbazole diimidazole (25.2 g, 155.4 mmol) And the mixture was heated at 80 DEG C for 12 hours under a nitrogen atmosphere and stirred. After the reaction was completed, the mixture was cooled to room temperature and extracted with brine and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to obtain Compound B-2 (16.0 g, yield 92%).

MS: [M + H] &lt; + &gt; = 130

Preparation of [Compound B-2]

2-fluoronitrobenzene (14 ml) and cesium carbonate (40 g) were placed, and the mixture was heated with stirring at 95 ° C for 2 hours to obtain a compound [B-1] (16.0 g, 123 mmol) . After the reaction was completed, the reaction mixture was cooled to room temperature, and ethyl acetate and brine were added thereto. The organic layer was washed twice with brine and water, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to obtain a dark brown oil. The product was subjected to column chromatography using a tetrahydrofuran / hexane (1/3) solution to obtain [Compound B-2] (18.5 g, yield 60%).

MS: [M + H] &lt; + &gt; = 251

Synthesis of [Compound B-3]

[Compound B-2] (18.5 g, 73.7 mmol) was dispersed in ethanol (500 ml). A 5% aqueous solution of sodium hydroxide (260 ml) was added thereto and the mixture was refluxed for 3 hours. After the reaction was completed, the reaction solution was decompressed to remove ethanol by about 1/5. Water (200 ml) was added to the precipitated solid, which was filtered under reduced pressure, washed with water, and dried under reduced pressure to obtain [Compound B-3] (15.4 g, yield 93.0%).

MS: [M + H] &lt; + &gt; = 225

Synthesis of [Compound B-4]

[Compound B-3] (15.4 g, 68.4 mmol) was dispersed in 85% phosphoric acid (200 ml). After stirring at room temperature for 12 hours, the mixture is poured into 1 L of water. The red precipitate was filtered with water and dried under reduced pressure to obtain [Compound B-4] (14.2 g, yield 85%).

MS: [M + H] &lt; + &gt; = 207

Synthesis of [Compound B-5]

After dissolving [Compound B-4] (14.2 g, 68.6 mmol) in ethanol (20 ml), 10% Pd-C (0.82 g, 7.7 mmol) was added to disperse and the mixture was cooled to 0 ° C. Hydrazine monohydrate (19 ml) was slowly added dropwise thereto. The mixture was heated to 50 &lt; 0 &gt; C for 30 minutes. The reaction mixture was cooled to room temperature, filtered through ethanol, and the filtrate was distilled under reduced pressure to obtain [Compound B-5] (10.3 g, yield 85.0%).

[Compound A-4] (11.2 g, MS: [M + H] &lt; + &gt; = 209)

[Compound A-5] (9.0 g, MS: [M + H] &lt; + &gt; = 209)

Preparation of [Compound A-6]

[Compound A-4] was prepared in the same manner as in [Compound A-2].

MS: [M + H] &lt; + &gt; = 344

Preparation of [Compound A-7]

[Compound A-5] was prepared in the same manner as in [Compound A-2].

MS: [M + H] &lt; + &gt; = 344

Preparation of [Formula 1-21]

(10 g, 29.1 mmol) and (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid ) (10.6 g, 30.6 mmol) and THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 ml of water and then added. It was added a catalytic Pd (PPh _{3) 4} 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered and dried to give 10.6 g (yield, 64%) of [Formula 1-21].

MS: [M + H] &lt; + &gt; = 567

PREPARATION EXAMPLE 10 Preparation of [Formula 1-44]

[Compound A-7] (10 g, 29.1 mmol) and 2- (4- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolen- 2- (4- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2- yl) phenyl) -1,10-phenanthroline (15.6 g, 30.6 mmol) and 150 mL of THF. 15 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. It was added a catalytic Pd (PPh _{3) 4} 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give 8.5 g (yield: 45%) of [Formula 1-44].

MS: [M + H] &lt; + &gt; = 645

PREPARATION EXAMPLE 11 Preparation of [Formula 1-76]

After dissolving 1-amino-2-methyl-2-propanol (17.3 g, 134.0 mmol) in tetrahydrofuran, carbazole diimidazole (25.2 g, 155.4 mmol) And the mixture was heated at 80 DEG C for 12 hours under a nitrogen atmosphere and stirred. After the reaction was completed, the mixture was cooled to room temperature and extracted with brine and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to obtain Compound B-2 (16.0 g, yield 92%).

MS: [M + H] &lt; + &gt; = 130

Preparation of [Compound B-2]

2-fluoronitrobenzene (14 ml) and cesium carbonate (40 g) were placed, and the mixture was heated with stirring at 95 ° C for 2 hours to obtain a compound [B-1] (16.0 g, 123 mmol) . After the reaction was completed, the reaction mixture was cooled to room temperature, and ethyl acetate and brine were added thereto. The organic layer was washed twice with brine and water, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to obtain a dark brown oil. The product was subjected to column chromatography using a tetrahydrofuran / hexane (1/3) solution to obtain [Compound B-2] (18.5 g, yield 60%).

MS: [M + H] &lt; + &gt; = 251

Synthesis of [Compound B-3]

[Compound B-2] (18.5 g, 73.7 mmol) was dispersed in ethanol (500 ml). A 5% aqueous solution of sodium hydroxide (260 ml) was added thereto and the mixture was refluxed for 3 hours. After the reaction was completed, the reaction solution was decompressed to remove ethanol by about 1/5. Water (200 ml) was added to the precipitated solid, which was filtered under reduced pressure, washed with water, and dried under reduced pressure to obtain [Compound B-3] (15.4 g, yield 93.0%).

MS: [M + H] &lt; + &gt; = 225

Synthesis of [Compound B-4]

[Compound B-3] (15.4 g, 68.4 mmol) was dispersed in 85% phosphoric acid (200 ml). After stirring at room temperature for 12 hours, the mixture is poured into 1 L of water. The red precipitate was filtered with water and dried under reduced pressure to obtain [Compound B-4] (14.2 g, yield 85%).

MS: [M + H] &lt; + &gt; = 207

Synthesis of [Compound B-5]

After dissolving [Compound B-4] (14.2 g, 68.6 mmol) in ethanol (20 ml), 10% Pd-C (0.82 g, 7.7 mmol) was added to disperse and the mixture was cooled to 0 ° C. Hydrazine monohydrate (19 ml) was slowly added dropwise thereto. The mixture was heated to 50 &lt; 0 &gt; C for 30 minutes. The reaction mixture was cooled to room temperature, filtered through ethanol, and the filtrate was distilled under reduced pressure to obtain [Compound B-5] (10.3 g, yield 85.0%).

MS: [M + H] &lt; + &gt; = 177

Synthesis of [Compound B-6]

[Compound B-5] (10.3 g, 58.2 mmol) and 4-bromobenzaldehyde (14.0 g, 75.6 mmol) were refluxed in ethyl acetate (100 ml) for 1 hour. Ethyl acetate was removed under reduced pressure, and the residue was dissolved in chloroform (200 ml). To this was added 2,3-dichloro-5,6-dicyano -1,4-benzoquinone, DDQ) (18.9 g, 83.2 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was distilled under reduced pressure, and the resulting black solid was subjected to column chromatography with a tetrahydrofuran / hexane (1/3) solution to obtain [Compound B-6] (13.9 g, yield 70.0%).

MS: [M + H] &lt; + &gt; = 342

Preparation of [Formula 1-76]

(10 g, 29.3 mmol) and (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid ) (10.6 g, 30.6 mmol) and THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 ml of water and then added. It was added a catalytic Pd (PPh _{3) 4} 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give [Formula 1-76] (12.3 g, yield 74%).

MS: [M + H] &lt; + &gt; = 565

PREPARATION EXAMPLE 12 Preparation of [Formula 1-84]

[Compound B-6] (10 g, 29.3 mmol) and 9,9'-spiro [fluorene] -2-ylboronic acid (11.0 g, 30.6 mmol) and THF (100 mL). 13 g of K ₂ CO ₃ was dissolved in 50 mL of water and added. It was added a catalytic Pd (PPh _{3) 4} 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give [Formula 1-84] (12.2 g, yield 72%).

MS: [M + H] &lt; + &gt; = 577

PREPARATION EXAMPLE 13 Preparation of [Formula 1-87]

[Compound B-6] (21.6 g, 63.4 mmol) and 2,6-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolen- 6-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalene (12.0 g, 31.7 mmol) and THF (100 mL). K ₂ CO ₃ Was dissolved in 50 mL of water and added. It was added a catalytic Pd (PPh _{3) 4} 1.4g was stirred and refluxed for 6 hours. After cooling to room temperature, the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give [Formula 1-87] (12.9 g, yield 63%).

MS: [M + H] &lt; + &gt; = 649

<Examples>

<Experimental Example 1-1>

A glass substrate coated with ITO (indium tin oxide) having a thickness of 500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer.

4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (1,000 Å) of the above formula was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the following BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 10: 1 to a thickness of 230 ANGSTROM to form a light emitting layer.

[Compound 1-1] was vacuum deposited on the light emitting layer to a thickness of 350 Å to form an electron injection and transport layer.

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 15 Å and a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr to produce an organic light emitting device.

<Experimental Example 1-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that [Compound 1-5] was used in place of [Compound 1-1] in Experimental Example 1-1.

<Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that [Compound 1-9] was used instead of [Compound 1-1] in Experimental Example 1-1.

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that [Compound 1-15] was used instead of [Compound 1-1] in Experimental Example 1-1.

<Experimental Example 1-5>

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1 except that [Compound 1-21] was used instead of [Compound 1-1] in Experimental Example 1-1.

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that [Compound 1-44] was used in place of [Compound 1-1] in Experimental Example 1-1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that [Compound 1-79] was used instead of [Compound 1-1] in Experimental Example 1-1.

<Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that [Compound 1-87] was used in place of [Compound 1-1] in Experimental Example 1-1.

&Lt; Comparative Example 1 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that the compound of the following formula (ET-A) was used instead of [Compound (1)

When current (10 mA / cm ² ) was applied to the organic light-emitting device manufactured by Experimental Examples 1-1 to 1-8 and Comparative Example 1, the results shown in Table 1 were obtained.

[Table 1]

From the results of Table 1, it can be seen that the novel compound according to the present invention can be used as a material for an organic material layer of an organic electronic device including an organic light emitting device, and an organic electronic device including the organic light emitting device using the same, It can be seen that it exhibits excellent characteristics. In particular, the novel compounds according to the present invention have excellent thermal stability, deep HOMO levels and hole stability, thus exhibiting excellent properties. When used in the electron transporting layer, the electron injection layer, or the layer which simultaneously transports electrons and injects electrons, the electron mobility is improved and the low voltage characteristics are excellent.

<Experimental Example 2-1>

Hexanitrile hexaazatriphenylene (HAT) of the above formula was thermally vacuum deposited to a thickness of 100 Å on the ITO transparent electrode prepared in Experimental Example 1-1 to form a hole injection layer.

(NPB) (700 angstroms), hexanitrile hexaazatriphenylene (HAT) (50 angstroms) were sequentially deposited on the hole injection layer by using the above-mentioned 4,4'-bis [N- (1-naphthyl) ) And 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (700 Å) were successively vacuum deposited thereon to form a hole transport layer.

Subsequently, the following BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 200 ANGSTROM to form a light emitting layer.

Compound [1-2] and LiQ (Lithium Quinalate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å.

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 15 Å and a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr to produce an organic light emitting device.

<Experimental Example 2-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that [Compound 1-6] was used instead of [Compound 1-2] in Experimental Example 2-1.

<Experimental Example 2-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that [Compound 1-18] was used instead of [Compound 1-2] in Experimental Example 2-1.

<Experimental Example 2-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that [Compound 1-84] was used instead of [Compound 1-2] in Experimental Example 2-1.

<Experimental Example 2-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that [Compound 1-102] was used instead of [Compound 1-2] in Experimental Example 2-1.

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the compound of the following formula (ET-A) was used instead of [Compound 1-2] in the Experimental Example 2-1.

When current (10 mA / cm ² ) was applied to the organic light-emitting devices fabricated by Experimental Examples 2-1 to 2-5 and Comparative Example 2, the results shown in Table 2 were obtained.

[Table 2]

From the results of Table 2, it can be seen that the novel compound according to the present invention can be used as a material for an organic material layer of an organic electronic device including an organic light emitting device, and an organic electronic device including the organic light emitting device using the same, It can be seen that it exhibits excellent characteristics. In particular, the novel compounds according to the present invention have excellent thermal stability, deep HOMO levels and hole stability, thus exhibiting excellent properties. It can be used purely in organic electronic devices including organic light emitting devices, or mixed with n-type dopants such as LiQ. The novel compounds according to the present invention improve the efficiency and improve the stability of the device by the thermal stability of the compound.

1: substrate
2: anode
3: Hole injection layer
4: hole transport layer
5: light emitting layer
6: electron transport layer
7: cathode

Claims (15)

A first electrode; A second electrode facing the first electrode; And an organic layer formed of one or more layers including a light emitting layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises a heterocyclic compound represented by the following Formula 1:
[Chemical Formula 1]

In formula (1)
X is CRR '
n is an integer of 1,
R and R 'are a substituted or unsubstituted alkyl group,
R1 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R2 to R5 are each independently hydrogen,
R6 to R8 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,
R 2 to R 8 are not simultaneously hydrogen. The organic light-emitting device according to claim 1, wherein at least one of R6 to R8 is a substituted or unsubstituted aryl group. The method according to claim 1,
And at least one of R2 to R8 is a substituted or unsubstituted aryl group. delete The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-73 to 1-95.

delete The method according to claim 1,
Wherein the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transport and electron injection,
Wherein the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and electron injects comprises the heterocyclic compound. The method according to claim 1,
Wherein the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes,
Wherein the hole injecting layer, the hole transporting layer, or the layer simultaneously injecting the hole and transporting the hole include the heterocyclic compound. The method of claim 7,
The electron transporting layer; An electron injection layer; Or an electron transporting and electron injecting layer simultaneously contains the heterocyclic compound as a p-type host and includes an n-type dopant as a dopant. The method of claim 9,
Wherein the n-type dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound or a combination thereof. The method of claim 9,
The n- type dopant group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li 2 O, CsF , or the following compounds Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

,

,

,

,

,

,

,

,

,

,

The method according to claim 1,
Wherein the light emitting layer comprises the heterocyclic compound. The method according to claim 1,
Wherein the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant. 14. The method of claim 13,
Wherein the phosphorescent dopant compound is represented by the following Formula 4:
[Chemical Formula 4]

In Formula 4,
M ₁ is Ir or Os,
L ₁₀ , L ₁₁ and L ₁₂ are the same or different and independently of each other are any one of the following structures,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

And

d ', f', g ', h', j, j ', and q', p, q, q ', r, s, t, u', v ', w', x ', a, b', c ' k is an integer of 0 to 4,
each of r ', s', t', u, v, w, x, y, y 'and e'
b, e, h, i, k 'and 1 are integers of 0 to 3,
c and g 'each represent an integer of 0 to 2,
f 'is an integer of 0 to 5,
z is an integer of 0 to 8,
R ₁₀ to R ₆₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C ₂ ~ _10; A substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C _1-10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; A substituted or unsubstituted C ₁ to C ₁₀ alkoxy group; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or adjacent groups form a condensed ring of a monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic ring. 15. The method of claim 14,
Wherein the phosphorescent dopant compound represented by Formula 4 is any one of the following compounds.

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