KR101768312B1 - 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 comprising 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. 10-2014-0058645, filed on May 15, 2014, 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. 2008-0049942

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)

A is an aromatic triple ring structure,

a is an integer of 1 to 8,

When a is 2 or more, two or more R's are the same or different from each other,

R1 to R4 and R are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A 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 allylic amine 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,

R1 to R4 and R are not simultaneously hydrogen.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises the heterocyclic compound do.

Heterocyclic compounds according to embodiments of the present disclosure have suitable energy levels and are 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.

Hereinafter, the present specification will be described in detail.

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

In one embodiment of the present specification, "aromatic ring structure" means that three rings of the same or different aromatic rings are condensed.

In one embodiment of the present invention, A is anthracene.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by Formula 2 or 3 below.

(2)

(3)

In formulas (2) and (3)

R1 to R4 are the same as defined in formula (1)

R5 to R10 are the same as or different from each other, and each independently is the same as defined for R,

R11 to R18 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; A 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 allylic amine 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,

R1 to R18 are not simultaneously hydrogen.

Hereinafter, the substituent will be described in detail.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine 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 aryl group; And a substituted or unsubstituted heterocyclic group, or does not have any substituent (s).

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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,

Quot; refers to a moiety that is connected to another substituent.

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, 2-methylpentyl, 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 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 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 a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

When the fluorenyl group is substituted,

,

,

And

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

In the present specification, the heterocyclic group is a heterocyclic group containing at least one hetero atom such as O, N, S, Se, etc. instead of a carbon atom. 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, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto. The heterocyclic group may be aromatic or aliphatic, and may be monocyclic or polycyclic, but is 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-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and 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, Naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl 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 alkyl group in the alkylthio group and the alkylsulfoxy group is the same as 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 mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In one embodiment of the present specification, at least one of R5 to R18 is the same or different and each independently represents an anthracenyl group substituted or unsubstituted with a substituent selected from the group consisting of an aryl group and a heterocyclic group ; A phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group; A spiroacridine fluorene group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a heterocyclic group; Or a spirofluorene indoloacridine group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In one embodiment of the present specification, a is at least 2, and at least one of 2 or more R is any one of the following substituents.

In the substituent,

X1 to X3 are each N or CR "

R "and Ar 1 to Ar 5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, the substituent is further selected from the group consisting of a halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine 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 aryl group; And a substituted or unsubstituted heterocyclic group.

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

In another embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenyl group.

In one embodiment, Ar1 is a phenyl group.

In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group.

In another embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present invention, Ar2 is a substituted or unsubstituted phenyl group.

In one embodiment, Ar2 is a phenyl group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group.

In another embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar 3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present invention, Ar3 is a substituted or unsubstituted phenyl group.

In one embodiment, Ar3 is a phenyl group.

In one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group.

In another embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar 4 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present invention, Ar4 is a substituted or unsubstituted phenyl group.

In one embodiment, Ar4 is a phenyl group.

In one embodiment of the present specification, Ar5 is a substituted or unsubstituted aryl group.

In another embodiment of the present specification, Ar5 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar5 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar5 is a substituted or unsubstituted phenyl group.

In one embodiment, Ar5 is a phenyl group.

In one embodiment of the present disclosure, X1 is N.

In another embodiment, X2 is N.

In another embodiment, X3 is N.

In one embodiment of the present disclosure,

The

to be.

In one embodiment of the present disclosure,

The

to be.

In another embodiment,

The

to be.

In another embodiment,

The

to be.

In another embodiment,

The

to be.

In one embodiment of the present disclosure, R1 is hydrogen.

In another embodiment, R2 is hydrogen.

In one embodiment of the present disclosure, R3 is hydrogen.

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

In one embodiment of the present invention, R5 in Formula 2 is hydrogen.

In another embodiment, R6 in Formula 2 is hydrogen.

In one embodiment, R7 in Formula 2 is hydrogen.

In another embodiment of the present specification, R8 in the general formula (2) is an anthracenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group; A phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group; A spiroacridine fluorene group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a heterocyclic group; Or a spirofluorene indoloacridine group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In one embodiment of the present invention, R 8 in Formula 2 is an anthracenyl group substituted or unsubstituted with an aryl group; A phenyl group substituted or unsubstituted with a heterocyclic group; A spiroacridine fluorene group substituted or unsubstituted with an aryl group; Or a spirofluorene indoloacridine group.

In one embodiment of the present invention, R8 in Formula 2 is an anthracenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

 In one embodiment of the present invention, R8 in Formula 2 is an anthracenyl group substituted or unsubstituted with an aryl group.

In one embodiment, R8 in Formula 2 is an anthracenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In another embodiment, R8 in Formula 2 is an anthracenyl group substituted with a phenyl group.

In one embodiment of the present invention, R8 in Formula 2 is a phenyl group which is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In one embodiment of the present invention, R8 in Formula 2 is a phenyl group substituted or unsubstituted with a substituted or unsubstituted heterocyclic group.

In another embodiment of the present specification, R8 in the above formula (2) is a phenyl group substituted or unsubstituted with a heterocyclic group containing at least one substituted or unsubstituted N atom.

In one embodiment of the present invention, R8 in Formula 2 is a phenyl group substituted or unsubstituted with a C2-C20 heterocyclic group containing at least one substituted or unsubstituted N atom.

In one embodiment, R8 in Formula 2 is a phenyl group substituted or unsubstituted with a heterocyclic group having 2 to 20 carbon atoms and containing at least one N atom which is substituted or unsubstituted with an aryl group.

In one embodiment, R8 in Formula 2 is a phenyl group substituted with a triazine group substituted with a phenyl group.

In another embodiment, R8 in Formula 2 is a phenyl group substituted with a carbazole group.

In one embodiment of the present invention, R8 in Formula 2 is a spirocadidine fluorene group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In another embodiment, R 8 in Formula 2 is a spiroacridine fluorene group substituted or unsubstituted with an aryl group.

In another embodiment, R8 in Formula 2 is a spiroacridine fluorene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

 In another embodiment, R 8 in Formula 2 is a spiroacridine fluorene group substituted or unsubstituted with a phenyl group.

In another embodiment, R8 in Formula 2 is 10-phenyl-10H-spiro [acridine-9,9'-fluorene].

In another embodiment of the present invention, R8 in the above formula (2) is a spirofluorene indoloaurcidine group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In another embodiment of the present specification, R8 in Formula 2 is a spiro [fluorene-9,8'-indolo [3,2,1-de] acridine group.

In another embodiment, R11 in Formula 2 is hydrogen.

In another embodiment, R12 in Formula 2 is hydrogen.

In one embodiment of the present specification, R13 in Formula 2 is hydrogen.

In another embodiment, R14 in Formula 2 is hydrogen.

In another embodiment of the present invention, R7 in Formula (3) is an anthracenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group; A phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group; A spiroacridine fluorene group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group and a heterocyclic group; Or a spirofluorene indoloacridine group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In one embodiment of the present invention, R7 in Formula 3 is an anthracenyl group substituted or unsubstituted with an aryl group; A phenyl group substituted or unsubstituted with a heterocyclic group; A spiroacridine fluorene group substituted or unsubstituted with an aryl group; Or a spirofluorene indoloacridine group.

In one embodiment of the present invention, R7 in Formula 3 is an anthracenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

 In one embodiment of the present invention, R7 in Formula 3 is an anthracenyl group substituted or unsubstituted with an aryl group.

In one embodiment, R7 in Formula 3 is an anthracenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In another embodiment, R7 in Formula 3 is an anthracenyl group substituted with a phenyl group.

In one embodiment of the present invention, R7 in Formula 3 is a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In one embodiment of the present invention, R7 in Formula 3 is a phenyl group substituted or unsubstituted with a substituted or unsubstituted heterocyclic group.

In another embodiment of the present invention, R7 in Formula 3 is a phenyl group substituted or unsubstituted with a heterocyclic group containing at least one substituted or unsubstituted N atom.

In one embodiment of the present invention, R7 in Formula 3 is a phenyl group substituted or unsubstituted with a C2-C20 heterocyclic group containing at least one substituted or unsubstituted N atom.

In one embodiment, R7 in Formula 3 is a phenyl group substituted or unsubstituted with a heterocyclic group having 2 to 20 carbon atoms and containing at least one N atom which is substituted or unsubstituted with an aryl group.

In one embodiment, R7 in Formula 3 is a phenyl group substituted with a triazine group substituted with a phenyl group.

In another embodiment, R7 in Formula 3 is a phenyl group substituted with a carbazole group.

In one embodiment of the present invention, R7 in Formula 3 is a spiroacridine fluorene group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In another embodiment, R7 in Formula 3 is a spiroacridine fluorene group substituted or unsubstituted with an aryl group.

In another embodiment, R7 in Formula 3 is a spiroacridine fluorene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

 In another embodiment, R7 in Formula 3 is a spiroacridine fluorene group substituted or unsubstituted with a phenyl group.

In another embodiment, R7 in Formula 3 is 10-phenyl-10H-spiro [acridine-9,9'-fluorene].

In another embodiment of the present disclosure, R7 in Formula 3 is a spirofluorene indoloacridine group substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heterocyclic group.

In another embodiment of the present specification, R7 in Formula 3 is a spiro [fluorene-9,8'-indolo [3,2,1-de] acridine group.

In one embodiment of the present specification, R7 in Formula 3 is hydrogen.

In one embodiment of the present specification, R9 in Formula 3 is hydrogen.

In another embodiment, R10 in Formula 3 is hydrogen.

In one embodiment of the present specification, R15 in Formula 3 is hydrogen.

In one embodiment of the present specification, R16 in Formula 3 is hydrogen.

In another embodiment, R17 in Formula 3 is hydrogen.

In another embodiment, R18 in Formula 3 is hydrogen.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 2-1 to 2-12.

In another embodiment, the heterocyclic compound represented by the formula (1) is represented by any of the following formulas (3-1) to (3-12).

The compound represented by the above formula (1) can be produced based on the following production example.

In one embodiment of the present specification, the heterocyclic compound represented by Formula 1 may be prepared by reacting a halogen-substituted benzimidazoiuoquinolinone group with R 2 substituted with a boronic acid or a boron ester. Those skilled in the art can change the R and / or R 1 to R 4 of the substituent as necessary to produce the heterocyclic compounds represented by the general formulas (2-1) to (2-12) and (3-1) to (3-12) Thus, a heterocyclic compound represented by the formula (1) having desired physical properties can be prepared.

The present invention also provides an organic light emitting device comprising the heterocyclic compound represented by Formula 1.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic material layer including a light emitting layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound, to provide.

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 of the present invention 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 one embodiment of the present invention, the organic material layer includes a hole transport layer, a hole injection layer, or a layer simultaneously injecting holes and transporting holes,

The hole transporting layer, the hole injecting layer, or the layer that simultaneously injects holes and transports holes includes the heterocyclic compound.

In another embodiment, the light emitting layer comprises the heterocyclic compound.

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transport and electron injection,

The electron transporting layer, the electron injecting layer, or the layer that simultaneously transports electrons and injects electrons includes the above heterocyclic compound.

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 organic material layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic compound layer including the heterocyclic compound.

In one embodiment of the present invention, the organic compound layer containing the heterocyclic compound includes the heterocyclic compound as a host and includes another organic compound, metal or metal compound as a dopant.

In one embodiment of the present invention, the organic layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.

In one embodiment of the present invention, the organic material layer is a hole injection layer, a hole transport layer. An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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

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

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

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 compound of Formula 1 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 addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the 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 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.

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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 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.

The dopant material includes an organic compound, a metal, or a metal compound.

Examples of the organic compound as the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, and a fluoranthene compound. 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. As the metal or metal compound, a common metal or metal compound can be used. Specifically, metal complexes can be used. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material 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. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, 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.

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

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

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

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

< Manufacturing example  1> Preparation of Formula 3-1

[Compound 1-A] [Compound 1-B] [Formula 3-1]

After completely dissolving the compound 1-A (11.6 g, 28.9 mmol) and 1-B (12.4 g, 28.9 mmol) in tetrahydrofuran (100 ml), 2M aqueous potassium carbonate solution (50 ml) Phosphino palladium (335 mg, 0.29 mmol) was added and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was suspended. The filtered yellow solid was washed once with tetrahydrofuran and once with ethanol to prepare the compound of Formula 3-1 (15.0 g, yield 80.3%).

MS [M + H] &lt; ⁺ &gt; = 598

< Manufacturing example  2> Preparation of Formula 2-1

[Compound 1-C] [Compound 1-B] [Formula 2-1]

The compound of Formula 2-1 was prepared in the same manner as the compound of Formula 3-1 except that 1-C was used instead of the compound 1-A.

MS [M + H] &lt; ⁺ &gt; = 598

< Manufacturing example  3> Preparation of Formula 3-2

[Compound 1-A] [Compound 1-D] [Formula 3-2]

The compound of Formula 3-2 was prepared in the same manner as the compound of Formula 3-1 except that 1-D was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 673

< Manufacturing example  4> Preparation of 3-3

[Compound 1-A] [Compound 1-E] [Formula 3-3]

The compound of Formula 3-3 was prepared in the same manner as the compound of Formula 3-1 except that 1-E was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 673

< Manufacturing example  5> Preparation of 3-4

[Compound 1-A] [Compound 1-F] [Formula 3-4]

The compound of Formula 3-4 was prepared in the same manner as the compound of Formula 3-1 except that 1-F was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 673

< Manufacturing example  6> Preparation of Formula 2-2

[Compound 1-C] [Compound 1-D] [Formula 2-2]

The compound of Formula 2-2 was prepared in the same manner as in the preparation of the compound of Formula 3-1 except that 1-C was used instead of the compound 1-A and 1-D was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 673

< Manufacturing example  7> Preparation of Formulas 2-3

[Compound 1-C] [Compound 1-E] [Formula 2-3]

The compound of Formula 2-3 was prepared in the same manner as in the preparation of Formula 3-1 except that 1-C was used instead of Compound 1-A and 1-E was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 673

< Manufacturing example  8> Preparation of 2-4

[Compound 1-C] [Compound 1-F] [Formula 2-4]

The compound of Formula 2-4 was prepared in the same manner as in the preparation of Compound 3-1 except that 1-C was used instead of Compound 1-A and 1-F was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 673

< Manufacturing example  9> Preparation of Formulas 3-5

[Compound 1-A] [Compound 1-G] [Formula 3-5]

The compound of Formula 3-5 was prepared in the same manner as the compound of Formula 3-1 except that 1-G was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 675

< Manufacturing example  10> Preparation of Formulas 3-6

[Compound 1-A] [Compound 1-H] [Formula 3-6]

The compound of Formula 3-6 was prepared in the same manner as the compound of Formula 3-1 except that 1-H was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 675

< Manufacturing example  11> Preparation of Formulas 3-7

[Compound 1-A] [Compound 1-I] [Formula 3-7]

The compound of Formula 3-7 was prepared in the same manner as the compound of Formula 3-1 except that 1-I was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 675

< Manufacturing example  12> Preparation of Formula 2-5

[Compound 1-C] [Compound 1-G] [Formula 2-5]

The compound of Formula 2-5 was prepared in the same manner as in the preparation of the compound of Formula 3-1 except that 1-C was used instead of the compound 1-A and 1-G was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 675

< Manufacturing example  13> Preparation of Formulas 2-6

[Compound 1-C] [Compound 1-H] [Formula 2-6]

The compound of Formula 2-6 was prepared in the same manner as in the preparation of the compound of Formula 3-1 except that 1-C was used instead of the compound 1-A and 1-H was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 675

< Manufacturing example  14> Preparation of 2-7

[Compound 1-C] [Compound 1-I] [Formula 2-7]

The compound of Formula 2-7 was prepared in the same manner as in the preparation of Formula 3-1 except that 1-C was used instead of Compound 1-A and 1-I was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 675

< Manufacturing example  15> Preparation of Formulas 3-8

[Compound 1-A] [Compound 1-J] [Formula 3-8]

The compound of Formula 3-8 was prepared in the same manner as the compound of Formula 3-1 except that 1-J was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 511

< Manufacturing example  16> Preparation of Formulas 3-9

[Compound 1-A] [Compound 1-K] [Formula 3-9]

The compound of Formula 3-9 was prepared in the same manner as the compound of Formula 3-1 except that 1-K was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 511

< Manufacturing example  17> Preparation of Formulas 3-10

[Compound 1-A] [Compound 1-L] [Formula 3-10]

The compound of Formula 3-10 was prepared in the same manner as the compound of Formula 3-1 except that 1-L was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 511

< Manufacturing example  18> Preparation of 2-8

[Compound 1-C] [Compound 1-J] [Formula 2-8]

The compound of Formula 2-8 was prepared in the same manner as in the preparation of the compound of Formula 3-1 except that 1-C was used instead of the compound 1-A and 1-J was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 511

< Manufacturing example  19> Preparation of 2-9

[Compound 1-C] [Compound 1-K] [Formula 2-9]

The compound of Formula 2-9 was prepared in the same manner as the compound of Formula 3-1 except that 1-C was used instead of the compound 1-A and 1-K was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 511

< Manufacturing example  20> Preparation of 2-10

[Compound 1-C] [Compound 1-L] [Formula 2-10]

Compound No. 2-10 was prepared in the same manner as in the preparation of Compound No. 3-1 except that 1-C was used instead of Compound 1-A and 1-L was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 511

< Manufacturing example  21> Preparation of Formulas 3-11

[Compound 1-A] [Compound 1-M] [Formula 3-11]

The compound of Formula 3-11 was prepared in the same manner as the compound of Formula 3-1 except that 1-M was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 577

< Manufacturing example  22> Preparation of Formulas 3-12

[Compound 1-A] [Compound 1-N] [Formula 3-12]

The compound of Formula 3-12 was prepared in the same manner as the compound of Formula 3-1 except that 1-N was used instead of the compound 1-B.

MS [M + H] &lt; ⁺ &gt; = 577

< Manufacturing example  23> Preparation of Formulas 2-11

[Compound 1-C] [Compound 1-M] [Formula 2-11]

The compound of Formula 2-11 was prepared in the same manner as in the preparation of Compound 3-1 except that 1-C was used instead of Compound 1-A and 1-M was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 577

< Manufacturing example  24> Preparation of Formulas 2-12

[Compound 1-C] [Compound 1-N] [Formula 2-12]

The compound of Formula 2-12 was prepared by the same method as that for preparing Compound 3-1 except that 1-C was used instead of Compound 1-A and 1-N was used instead of 1-B. Respectively.

MS [M + H] &lt; ⁺ &gt; = 577

< OLED  Device fabrication evaluation>

Comparative Example  One)

[Hexanitrile hexaazatriphenylene] [NPB]

 [H1] [D1]

[E1] [E2]

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a product of Fischer Co. was used as a detergent, and distilled water, which was secondly filtered by a filter manufactured by 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. The substrate was subjected to thermal vacuum deposition of hexanitrile hexaazatriphenylene (HAT) of the above formula for 5 minutes using oxygen plasma to form a hole injection layer.

(NPB) (700 Å), hexanitrile hexaazatriphenylene (HAT) (50 Å), and the like were added to the hole injection layer, and 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, H1 and D1 were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 with a thickness of 200 ANGSTROM to form a light emitting layer. An electron transport layer was formed on the light-emitting layer to a thickness of 100 ANGSTROM. E1 and E2 were vacuum deposited on the electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 200 ANGSTROM.

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 15 Å and a thickness of 2000 Å on the electron injection and transport 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.

Example  One)

The same experiment as in Comparative Example 1 was carried out except that the compound of Formula 3-1 was used instead of H1 of the light emitting layer in Comparative Example 1).

Example  2)

In the same manner as in Comparative Example 1 except that NPB (600 Å) / compound of Formula 3-3 (100 Å) was laminated instead of hole transport NPB (700 Å) in contact with the light emitting layer in the above Comparative Example 1.

Example  3)

In the same manner as in Comparative Example 1 except that NPB (600 ANGSTROM) / compound of Formula 3-5 (100 ANGSTROM) was laminated instead of the hole transport layer NPB (700 ANGSTROM) in contact with the light emitting layer in the above Comparative Example 1.

Example  4)

The procedure of Comparative Example 1 was repeated except that NPB (600 ANGSTROM) / compound of Formula 3-9 (100 ANGSTROM) was laminated instead of the hole transport layer NPB (700 ANGSTROM) in contact with the light emitting layer in Comparative Example 1.

Example  5)

The same experiment as in Comparative Example 1 was carried out except that the compound of Formula 2-10 was used in place of the electron injection and electron transport layer E1 in Comparative Example 1 above.

The driving voltage and the luminous efficiency of the organic light emitting device manufactured in Examples 1 to 5 and Comparative Example 1 were measured at a current density of 10 mA / cm ^2. The results are shown in Table 1 below.

Experimental Example
10mA / ㎠ The Voltage (V) Current efficiency (cd / A) Comparative Example 1 Ref. 4.2 4.5 Example 1 3-1 4.2 4.6 Example 2 3-3 4.5 4.8 Example 3 3-5 4.4 4.7 Example 4 3-9 4.6 4.8 Example 5 2-10 4.0 4.5

From the results of Table 1, it can be confirmed that the heterocyclic compound represented by Chemical Formula 1 according to one embodiment of the present invention can be used as a material of an organic material layer of an organic electronic device including an organic light emitting device.

Also, it can be seen from the above Examples and Comparative Examples that the organic light emitting device including the heterocyclic compound according to one embodiment of the present invention has low driving voltage and high efficiency characteristics.

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

Claims (12)

A heterocyclic compound represented by the following formula (2) or (3):
(2)

(3)

In formulas (2) and (3)
R1 to R4 are hydrogen,
At least one of R5 to R18 is an anthracenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; A phenyl group substituted or unsubstituted with an aryl group and substituted with a heterocyclic group having 2 to 20 carbon atoms and containing at least one N atom; A spiroacridine fluorene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Or a spirofluorene indoloacridine group, and the remainder is hydrogen. delete delete delete The method according to claim 1,
The heterocyclic compound represented by the formula (2) is represented by any one of the following formulas (2-1) to (2-12)

. The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 3 is represented by any one of the following Formulas 3-1 to 3-24:

. A first electrode; A second electrode facing the first electrode; And at least one organic layer including a light emitting layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises the heterocyclic compound according to any one of claims 1, 5 and 6. The method of claim 7,
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 that simultaneously transports electrons and injects electrons comprises the heterocyclic compound. The method of claim 7,
Wherein the light emitting layer comprises the heterocyclic compound. The method of claim 7,
Wherein the organic material layer includes a hole blocking layer,
Wherein the hole blocking layer comprises the heterocyclic compound. The method of claim 7,
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously injecting holes and transporting holes,
Wherein the hole transport layer, the hole injection layer, or the layer that simultaneously injects holes and transports the hole transport layer includes the heterocyclic compound. The method of claim 7,
Wherein the organic material layer is a hole injection layer, a hole transport layer. An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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