KR101832084B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0009544 filed with the Korean Intellectual Property Office on January 26, 2016, the entire contents of which are incorporated herein by reference.

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

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

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

U.S. Patent Application Publication No. 2004-0251816

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

According to one embodiment of the present invention, there is provided a heterocyclic compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

At least one of X1 to X3 is N, and the others are CH,

L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar 2 and Ar 3 are the same or different and are each independently a substituted or unsubstituted aryl group,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

과 Ar1는 서로 상이하며,remind

And Ar1 are different from each other,

는 화학식 1의 L1에 결합되는 부위이다.remind

Is a moiety bonded to L 1 in formula (1).

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a heterocyclic compound represented by Formula 1, to provide.

The heterocyclic compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device and by using it, it is possible to improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting device.

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

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

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

The heterocyclic compound according to one embodiment of the present invention has a structure in which a substituent is bonded through the linking groups L1 and L2 at positions 1 and 4 of naphthalene. In this case, since the naphthalene has an appropriate twist structure around naphthalene, The electron interactions due to the conjugation between the substituents on both sides are reduced and the independent characteristics of the substituents are maintained and the appropriately maintained conjugation is a structure capable of preventing the lifetime of the organic light emitting device from deteriorating due to excessive electron injection It is possible to improve the efficiency, improve the driving voltage and the life characteristic of the organic light emitting device.

In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

Examples of substituents in the present specification are described below, but are not limited thereto.

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy 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 amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. 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.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 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 an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 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 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is 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 30 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 this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms 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- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine 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, And the like, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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, However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 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 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, no.

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

,

,

,

,

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.

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 other substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention 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. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, There may be mentioned phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazinyl group and dibenzofuranyl group. But is not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.

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

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

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; Or an arylene group.

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; Or a phenylene group.

According to one embodiment of the present invention, in Formula 1, L1 is an arylene group.

According to one embodiment of the present invention, in Formula 1, L1 is a phenylene group.

According to one embodiment of the present invention, in Formula 1, L2 is a direct bond; Or an arylene group.

According to one embodiment of the present invention, in Formula 1, L2 is a direct bond; Or a phenylene group.

According to one embodiment of the present invention, in the general formula (1), Ar2 and Ar3 are the same or different and each independently an arylene group.

According to one embodiment of the present invention, in the general formula (1), Ar2 and Ar3 are the same or different and each independently represent a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different from each other and each independently represent a phenylene group; Biphenyllylene groups; Or a naphthylene group.

According to one embodiment of the present invention, Ar 1 is an aryl group substituted or unsubstituted with an alkyl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar 1 is a substituted or unsubstituted fluorenyl group; A fluoranthenyl group; A triphenylrenyl group; A pyridyl group substituted or unsubstituted with an aryl group; A pyrimidyl group substituted or unsubstituted with an aryl group; A benzimidazolyl group substituted or unsubstituted with an aryl group; A benzotriazolyl group; Or a carbazolyl group.

According to one embodiment of the present invention, Ar 1 is a substituted or unsubstituted fluorenyl group; A fluoranthenyl group; A triphenylrenyl group; A pyridyl group substituted or unsubstituted with a phenyl group; A pyrimidyl group substituted or unsubstituted with a phenyl group; A benzimidazolyl group substituted or unsubstituted with a phenyl group; A benzotriazolyl group; Or a carbazolyl group.

According to one embodiment of the present disclosure, Formula 1 is selected from the following compounds.

According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the above-described heterocyclic compound.

According to one embodiment of the present disclosure, the organic material layer of the organic light emitting device 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, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

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

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

2 shows a structure in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90 and a second electrode 50) are successively laminated on a substrate. 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

According to an embodiment of the present invention, the organic material layer includes an electron injection layer, and the electron injection layer includes a heterocyclic compound represented by the formula (1).

According to one embodiment of the present invention, the organic material layer includes an electron transporting layer, and the electron transporting layer includes a heterocyclic compound represented by the general formula (1).

According to an embodiment of the present invention, the organic material layer includes a layer simultaneously injecting electrons and transporting electrons, and the layer simultaneously injecting and transporting electrons includes a heterocyclic compound represented by the general formula (1).

According to one embodiment of the present invention, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a heterocyclic compound represented by the general formula (1).

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1) as a host of the light emitting layer.

In one embodiment of the present invention, the organic material layer includes the heterocyclic compound represented by Formula 1 as a host, and may include other organic compound, metal or metal compound as a dopant.

The dopant may be at least one selected from the following compounds, but is not limited thereto.

According to one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following formula 1-A.

[Chemical Formula 1-A]

In the above formula (1-A)

n1 is an integer of 1 or more,

Ar7 is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,

L4 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar8 and Ar9 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group or may be bonded to each other to form a substituted or unsubstituted ring,

When n1 is 2 or more, the structures in parentheses two or more are the same or different from each other.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by the formula 1-A as a dopant in the light emitting layer.

According to one embodiment of the present disclosure, L4 is a direct bond.

According to one embodiment of the present disclosure, n1 is 2.

In one embodiment of the present specification, Ar7 is a divalent pyylene group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group; Or a divalent cyclic group substituted or unsubstituted with a deuterium, a methyl group, an ethyl group or a tert-butyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and are each independently a substituted or unsubstituted aryl group substituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, Lt; / RTI >

According to one embodiment of the present disclosure, Ar8 and Ar9 are aryl groups which are the same or different and are each independently substituted or unsubstituted with a silyl group substituted with an alkyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are aryl groups which are the same or different and are each independently substituted or unsubstituted with trimethylsilyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and each independently a phenyl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and are each independently a biphenyl apparatus substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and each is a terphenyl group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and each independently represent a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and each independently represents a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group, Lt; / RTI >

According to one embodiment of the present invention, Ar8 and Ar9 are the same or different and each independently represents a dibenzofurane group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a trimethylsilyl group, to be.

According to one embodiment of the present disclosure, the above formula (I-A) is selected from the following compounds.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following formula (2-A).

[Chemical Formula 2-A]

In the above formula (2-A)

Ar11 and Ar12 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,

G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.

According to one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 2-A as a host of the light-emitting layer.

According to one embodiment of the present invention, Ar11 and Ar12 are the same or different and each independently a substituted or unsubstituted polycyclic aryl group.

According to one embodiment of the present invention, Ar11 and Ar12 are the same or different and each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

According to one embodiment of the present invention, Ar11 and Ar12 are the same or different and each independently a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, Ar11 and Ar12 are the same or different and each independently a substituted or unsubstituted 1-naphthyl group.

According to one embodiment of the present invention, Ar11 and Ar12 are 1-naphthyl groups.

According to one embodiment of the present invention, G1 to G8 are hydrogen.

According to one embodiment of the present invention, the formula (2-A) is selected from the following compounds.

According to an embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by the formula 1-A as a dopant of the light emitting layer, .

According to an embodiment of the present invention, the organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

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

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

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition 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.

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

According to another embodiment of the present invention, 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, LiO ₂ / Al, and Mg / Ag, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from the electrode as a hole injecting material and a hole injecting effect for injecting holes in the anode as a hole injecting material and an excellent hole injecting effect for a light emitting layer or a light emitting material , The migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also the ability to form thin films 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 electron blocking layer is a layer that prevents electrons injected from the electron injection layer from entering the hole injection layer through the light emission layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The light emitting material of the light emitting layer 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 high 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; Benzoxazole, benzothiazole and benzimidazole compounds; 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 may be 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 heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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 hole blocking layer prevents the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material is suitable. 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 with a low work function followed by an aluminum layer or 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 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.

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

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

Synthesis Example 1 Synthesis of Compound 1

[Compound 1A]

[Compound 1A] [Compound 1B]

[Compound 1B] [Compound 1]

(1) Preparation of Compound 1A

(THF) (300 mL), H (30 mL), potassium carbonate (K ₂ CO ₃ ) (39 g, 282 mmol), trihydrochloric acid ₂ O (100 ml) and heated to 90 < 0 > C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (2.17g, 1.88mmol) was refluxed for 1 hour. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 1A (30 g, yield 71%).

MS: [M + H] < ⁺ > = 452

(2) Preparation of Compound 1B

The compound 1A (22 g, 48.8 mmol), C ₄ F ₁₀ O ₂ S (10.5 ml, 58.4 mmol) and potassium carbonate (K ₂ CO ₃ ) (20 g, 145 mmol) were dissolved in acetonitrile Respectively. Refluxed for 12 hours, cooled to room temperature and filtered. Compound 1B (30 g, yield 84%) was obtained.

MS: [M + H] < ⁺ > = 734

(3) Preparation of Compound 1

Compound 1B (16g, 21.8mmol) and diphenyl-pyridine-boronic acid (10.4g, 24mmol) and potassium carbonate _{(K 2 CO 3) (9g} , 65.2mmol) of tetrahydrofuran (THF) (300mL), H 2 O ( 100 ml) and heated to 90 [deg.] C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.5g, 0.43mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 1 (11 g, yield 68%).

MS: [M + H] < ⁺ > = 741

Synthesis Example 2 Preparation of Compound 2

[Compound 1B] [Compound 2]

Compound (2) (20 g, yield 78%) was prepared in the same manner except that pyridine phenylboronic acid (4.8 g, 24 mmol) was used in place of diphenylpyridineboronic acid in the preparation of Compound (3) ).

MS: [M + H] < ⁺ > = 589

SYNTHESIS EXAMPLE 3 Preparation of Compound 3

[Compound 1B] [Compound 3]

Except that carbazole phenylboronic acid (6.9 g, 24 mmol) was used in place of diphenylpyridine boronic acid in the preparation of Compound (3) of Synthesis Example 1 (3) (12 g, yield 82 %).

MS: [M + H] < ⁺ > = 676

Synthesis Example 4 Preparation of Compound 4

[Compound 1B] [Compound 4]

Except that fluoranthenboronic acid (5.9 g, 24 mmol) was used in place of diphenylpyridineboronic acid in the preparation of Compound (3) of Synthesis Example 1 (3) to obtain Compound 4 (10 g, yield 72 %).

MS: [M + H] < ⁺ > = 635

SYNTHESIS EXAMPLE 5 Preparation of Compound 5

[Compound 1B] [Compound 5]

(3) Compound 1 of Synthesis Example 1 was prepared in the same manner except that compound diphenylpyrimidine boronic acid (8.4 g, 24 mmol) was used instead of compound diphenylpyridine boronic acid to give Compound 5 ( 13 g, yield: 81%).

MS: [M + H] < ⁺ > = 741

≪ Synthesis Example 6 > Preparation of Compound 6

[Compound 2B] [Compound 6]

Compound 6 (9 g, yield 65%) was obtained by the same method as Compound 4B except that Compound 2B (5.9 g, 24 mmol) was used instead of Compound 1B in Synthesis Example 4.

MS: [M + H] < ⁺ > = 634

Synthesis Example 7 Preparation of Compound 7

[Compound 1B] [Compound 7]

Compound (7) (12 g, yield: 82%) was prepared in the same manner as in the preparation of Compound (3) of Synthesis Example 1, except that metaphenyltriphenylboronic acid (8.4 g, 24 mmol) was used instead of diphenylpyridineboronic acid 75%).

MS: [M + H] < ⁺ > = 737

SYNTHESIS EXAMPLE 8 Preparation of Compound 8

[Compound 3B] [Compound 8]

(1) Preparation of Compound 8

Compound 8 (10 g, yield 68%) was obtained by the same method as Compound 3B except that Compound 3B (6.9 g, 24 mmol) was used instead of Compound 1B in Synthesis Example 3.

MS: [M + H] < ⁺ > = 676

Synthesis Example 9 Synthesis of Compound 9

[Compound 4B] [Compound 9]

Compound 4B (18 g, 23 mmol) was used instead of compound 1B and compound 4-pyridinephenylboronic acid (5.0 g, 25.2 mmol) was used in place of compound 2-pyridine phenylpyridineboronic acid in the preparation of Compound 2 of Synthesis Example 2 (9.5 g, yield 65%) was obtained.

MS: [M + H] < ⁺ > = 638

Synthesis Example 10 Preparation of Compound 10

[Compound 5B] [Compound 10]

(1) Preparation of Compound 10

(3) Compound 1 of Synthesis Example 1 was used instead of Compound 1B, compound 8B (18 g, 22.2 mmol) was used instead of compound 1B, and compound fluorenephenylboronic acid (7.7 g, 24.5 mmol) was used instead of compound diphenylpyridine boronic acid (11 g, yield 66%).

MS: [M + H] < ⁺ > = 753

≪ Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1000 Å was immersed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. HT1 (400 Å), which is a hole transporting material, was vacuum deposited on the hole transporting layer, and a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. Compound 1 prepared in Synthesis Example 1 and LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode. Thereby preparing an organic light emitting device.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 < ^-6 > torr, thereby fabricating an organic light emitting device.

[Hexanitrile hexaazatriphenylene] [LiQ]

[HT1]

[H1]

 [D1]

≪ Example 2 >

The same experiment was conducted except that Compound 2 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

≪ Example 3 >

The same experiment was conducted except that Compound 3 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

<Example 4>

The same experiment was conducted except that Compound 4 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

&Lt; Example 5 >

The same experiment was conducted except that Compound 5 was used instead of Compound 1 as the electron injection and transport layer in Example 1 above.

&Lt; Example 6 >

The same experiment was conducted except that Compound 6 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

&Lt; Example 7 >

The same experiment was conducted except that Compound 7 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

&Lt; Example 8 >

The same experiment was conducted except that Compound 8 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

&Lt; Example 9 >

The same experiment was carried out except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1 above.

&Lt; Example 10 >

The same experiment was conducted except that Compound 10 was used instead of Compound 1 as the electron injecting and transporting layer in Example 1 above.

&Lt; Comparative Example 1 &

The same experiment was carried out except that the compound of ET1 was used in place of Compound 1 as the electron injecting and transporting layer in Experimental Example 1 above.

[ET1]

&Lt; Comparative Example 2 &

The same experiment was conducted except that the compound of ET2 was used in place of the compound 1 as the electron injecting and transporting layer in Experimental Example 1 above.

[ET2]

&Lt; Comparative Example 3 &

The same experiment was conducted except that the compound of ET3 was used in place of the compound 1 as the electron injecting and transporting layer in Experimental Example 1 above.

[ET3]

&Lt; Comparative Example 4 &

In the same manner as in Experimental Example 1, except that the compound of ET4 was used in place of the compound 1 as the electron injecting and transporting layer.

[ET4]

&Lt; Comparative Example 5 &

The same experiment was conducted except that the compound of ET5 was used in place of the compound 1 as the electron injecting and transporting layer in Experimental Example 1 above.

[ET5]

&Lt; Comparative Example 6 >

In the same manner as in Experimental Example 1, except that the compound of ET6 was used in place of Compound 1 as the electron injecting and transporting layer.

[ET6]

Table 1 shows the results of experiments of the organic light emitting devices manufactured using the compounds as the electron injection and transport layer materials as in Examples 1 to 10 and Comparative Examples 1 to 6.

Experimental Example
10 mA / cm 2 compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) Example 1 Compound 1 3.91 5.47 (0.137, 0.124) Example 2 Compound 2 3.89 5.41 (0.139, 0.124) Example 3 Compound 3 3.88 5.52 (0.138, 0.126) Example 4 Compound 4 3.90 5.35 (0.138, 0.128) Example 5 Compound 5 3.75 5.24 (0.137, 0.162) Example 6 Compound 6 3.84 5.30 (0.137, 0.124) Example 7 Compound 7 3.88 5.64 (0.137, 0.162) Example 8 Compound 8 3.81 5.55 (0.137, 0.162) Example 9 Compound 9 3.99 5.28 (0.137, 0.162) Example 10 Compound 10 3.81 5.47 (0.137, 0.162) Comparative Example 1 ET1 4.00 5.01 (0.140, 0.129) Comparative Example 2 ET2 4.01 5.03 (0.140, 0.129) Comparative Example 3 ET3 4.01 4.99 (0.139, 0.129) Comparative Example 4 ET4 4.55 4.3 (0.137, 0.162) Comparative Example 5 ET5 4.07 4.87 (0.137, 0.125) Comparative Example 6 ET6 4.05 4.62 (0.137, 0.124)

In Table 1, the organic light emitting device manufactured using the heterocyclic compound represented by Formula 1 according to one embodiment of the present invention has lower driving voltage and higher efficiency than the organic light emitting devices of Comparative Examples 1 to 6 It can be seen that it is excellent.

In particular, the heterocyclic compound represented by the formula (1) according to one embodiment of the present invention has a structure in which substituent groups are bonded through the linking groups L1 and L2 at positions 1 and 4 of naphthalene, Or naphthalene, which has an appropriate twist structure than the compound bonded at positions 2 and 7 of naphthalene, so that the electronic interaction due to the conjugation between both substituents around naphthalene is reduced and the independent characteristics of the substituents are maintained The conjugation which is suitably maintained can improve the efficiency in the organic light emitting device, improve the driving voltage and the lifetime of the organic light emitting device, and so on, by the structure characteristic that can prevent the lifetime of the organic light emitting device from deteriorating due to excessive electron injection.

과 Ar1이 서로 동일한 화합물로 제조된 비교예 5 및 6의 유기 발광 소자 보다 치환기 사이의 컨쥬게이션에 의한 전자적 상호작용이 작아져 치환기들의 독립적인 특성이 유지되므로, 낮은 구동 전압 및 전류 효율이 우수하다.In addition, the organic light emitting device manufactured using the heterocyclic compound represented by Formula 1 according to one embodiment of the present invention has the structure of Formula 1

And Ar1 of the organic EL device of Comparative Examples 5 and 6, which are made of the same compound, the electron interactions due to the conjugation between the substituents are reduced and the independent characteristics of the substituents are maintained, so that the low driving voltage and current efficiency are excellent .

10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron transport layer
90: electron injection layer

Claims (16)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
At least one of X1 to X3 is N, and the others are CH,
L1 is an arylene group,
L2 is a direct bond; Or an arylene group,
Ar2 and Ar3 are the same or different and each independently an aryl group,
Ar 1 is an aryl group substituted or unsubstituted with an alkyl group; Or a monocyclic or polycyclic heteroaryl group substituted or unsubstituted with an aryl group,
When L2 is a direct bond, Ar1 is an aryl group substituted or unsubstituted with an alkyl group; Or a polycyclic heteroaryl group substituted or unsubstituted with an aryl group,
remind

And Ar1 are different from each other,
remind

Is a moiety bonded to L 1 in formula (1). delete delete [2] The compound according to claim 1, wherein Ar2 and Ar3 are the same or different from each other and are each independently a phenyl group; A biphenyl group; Or a naphthyl group. delete 2. The heterocyclic compound according to claim 1, wherein the formula 1 is selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises the heterocyclic compound of any one of claims 1, 4 and 6 Organic light emitting device. 8. The organic electroluminescent device according to claim 7, wherein the organic material layer comprises an electron injection layer, an electron transport layer, or a layer simultaneously injecting and transporting electrons, wherein the electron injection layer, the electron transport layer, And an organic light emitting layer. [Claim 7] The organic light emitting device of claim 7, wherein the organic layer includes a hole blocking layer, and the hole blocking layer comprises the heterocyclic compound. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer. [7] The organic light emitting device of claim 7, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula
[Chemical Formula 1-A]

In the above formula (1-A)
L4 is a direct bond,
Ar7 is a divalent pyrene group,
Ar8 and Ar9 are the same or different and each independently represents an aryl group which is substituted or unsubstituted with a silyl group substituted with an alkyl group,
n1 is 2,
When n1 is 2, the structures in parentheses of 2 are the same or different from each other. delete The method of claim 7,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises a compound represented by the following Formula 2-A:
[Chemical Formula 2-A]

In the above formula (2-A)
Ar11 and Ar12 are 1-naphthyl groups,
G1 to G8 are hydrogen. delete The method of claim 12,
Wherein the light emitting layer comprises a compound represented by the following Formula 2-A:
[Chemical Formula 2-A]

In the above formula (2-A)
Ar11 and Ar12 are 1-naphthyl groups,
G1 to G8 are hydrogen.

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