KR101639867B1 - Hetero-cyclic 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 including the heterocyclic compound.

Description

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

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

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2013-0079808 filed with the Korean Intellectual Property Office on July 8, 2013, the entire contents of which are incorporated herein by reference.

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.

Korean Patent Publication No. 2007-0003586

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)

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms,

L2 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms,

Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

Ar3 is the following formula (2) or (3)

(2)

(3)

In formulas (2) and (3)

X is S or O,

a is an integer of 0 to 8,

b is an integer of 0 to 7,

When a is 2 or more, R1 is the same as or different from each other,

When b is 2 or more, R2 is the same as or different from each other,

R1 and R2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms, or adjacent groups may be bonded to each other to form a hydrocarbon ring or at least one of N, O and S atoms To form a heterocyclic ring.

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

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

Fig. 1 shows an example of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated.
2 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked FIG.

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

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

In one embodiment of the present specification, L2 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms. In this case, it is possible to prevent the life degradation phenomenon due to the twisting effect of the structure, and by adjusting the conjugation length, it is possible to reflect the inherent optical and / or electronic characteristics of Ar3 or -NAr1Ar2 centered on the naphthalene group do.

는 다른 치환기에 연결되는 부위를 의미한다.In the present specification,

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

In one embodiment of the present invention, the heterocyclic compound is represented by the following general formula (3-1) or (3-2).

[Formula 3-1]

[Formula 3-2]

In Formulas (3-1) and (3-2), X, R2 and b are the same as defined above.

In one embodiment of the present invention, each of L1 and L2 is a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted terphenyl group.

Illustrative examples of such substituents are set forth 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; A hydroxy group; Thiol group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; An aryl group; Arylalkyl groups; An arylalkenyl group; And a heterocyclic group containing at least one of O, N and S as a heteroatom, at least one of which is substituted or unsubstituted with at least one substituent selected from the above-exemplified substituents, It means unsubstituted. For example, the "substituent group to which two or more 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.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, N-octyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 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. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

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

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

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include 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, phenanthrenyl, pyrenyl, perylenyl, tetracenyl, klychenyl, fluorenyl, a fluoranthene group, and the like, but the present invention is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to 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.

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

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

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

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-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 heterocyclic group is a heterocyclic group containing at least one of O, N and S as a heteroatom. 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.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, 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. However, 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 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, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, adjacent groups refer to respective substituents in which R1 and R2 are adjacent to each other when a and b are two or more.

In the present specification, adjacent groups are bonded to each other to form a hydrocarbon ring or a heterocycle containing one or more of N, O and S atoms, when a and b are two or more, each of R1 and R2, Means that a substituent forms a bond to form a 5- to 8-membered hydrocarbon ring or a heterocyclic ring structure.

As used herein, the hydrocarbon ring is a cycloalkyl group; A cycloalkenyl group; Aromatic ring group; Or an aliphatic cyclic group, which may be monocyclic or polycyclic, and includes all rings in which one or more of them are bonded and condensed.

The term "heterocycle" as used herein means that at least one carbon atom of the hydrocarbon ring is substituted with N, O, or S atoms, and may be an aliphatic ring or an aromatic ring, and may be monocyclic or polycyclic.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any of Formula 1-a, 1-b, 1-c, 1-d, 1-e and 1-f.

[Chemical Formula 1-a]

[Chemical Formula 1-b]

[Chemical Formula 1-c]

[Chemical formula 1-d]

[Formula 1-e]

[Chemical Formula 1-f]

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group.

In one embodiment of the present invention, L1 is a substituted or unsubstituted phenylene group.

In one embodiment of the present invention, L1 is a phenylene group.

In one embodiment of the present specification, L2 is a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L2 is a substituted or unsubstituted phenylene group.

In one embodiment of the present invention, L2 is a phenylene group.

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

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

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

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

In one embodiment of the present invention, Ar1 is a naphthyl group.

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

In one embodiment of the present invention, Ar1 is a biphenyl group.

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

In one embodiment of the present invention, Ar1 is a terphenyl group.

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

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

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

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

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

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

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

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

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

In one embodiment of the present specification, Ar3 is the formula (2).

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

In one embodiment of the present specification, Ar3 is the formula (3).

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

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

In one embodiment of the present disclosure, L1 is a direct bond; Or a substituted or unsubstituted phenylene group, L 2 is a substituted or unsubstituted phenylene group, Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted terphenyl group.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by the following Formulas 1-a-1 to 1-a-17, 1-b-1 to 1-b-17, Can be represented by any one of 1-c-17, 1-d-1 to 1-d-17, 1-e-1 to 1-e-17 and 1-f-1 to 1-f-17 .

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-a is any one of the following Formulas 1-a-1 to 1-a-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-b is any one of the following Formulas 1-b-1 to 1-b-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-c is any one of the following Formulas 1-c-1 to 1-c-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-d is any one of the following Formulas 1-d-1 to 1-d-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-e is any one of the following Formulas 1-e-1 to 1-e-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-f is any one of the following Formulas 1-f-1 to 1-f-17.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by the following Formulas 2-a-1 to 2-a-17, 2-b-1 to 2-b-17, Can be represented by any one of 2-c-17, 2-d-1 to 2-d-17, 2-e-1 to 2-e-17 and 2-f-1 to 2-f-17 .

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-a is any one of the following Formulas 2-a-1 to 2-a-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-b is any one of the following Formulas 2-b-1 to 2-b-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-c is any one of the following Formulas 2-c-1 to 2-c-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-d is any one of the following Formulas 2-d-1 to 2-d-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-e is any one of the following Formulas 2-e-1 to 2-e-17.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1-f is any one of the following Formulas 2-f-1 to 2-f-17.

 In one embodiment of the present invention, the carbazole derivative represented by the above formula (1) can be prepared by the following production example.

The compound represented by the formula (1) has a structure in which a halogen group on one side and a hydroxyl group on the other side are substituted with naphthalene A3 and L1, and the structure substituted with boronic acid is reacted. After the reaction, 1,1,2,2,3,3,4,4,4- nonafluoro After reacting the butane-1-sulfonyl fluoride _{(C 4 F 10 O 2 S} ) fluoro, L2 is-NAr1Ar2 Or a structure substituted with a borane group.

The heterocyclic compound represented by the general formula (1) as well as the general formulas (1-a) to (1-f) can be prepared by the above-mentioned method by controlling the position where the halogen group and the hydroxyl group or the aldehyde group are substituted.

In the present specification, the heterocyclic compound of formula (1) is used as an organic material layer used in an organic light emitting device by introducing a substituent including an amine group on one side and a heterocycle on the other side of the naphthalene group May have suitable characteristics.

The compound represented by Formula 1 is substituted with Formula 2 or Formula 3. Therefore, the compound represented by the general formula (1) includes a compound represented by the general formula (2) or (3) including a heterocyclic structure, so that it can have an appropriate energy level as a hole injection and / or hole transporting material in an organic light emitting device. In this specification, a compound having an appropriate energy level according to the substituent among the compounds represented by the formula (1) is selected and used in an organic light emitting device, thereby realizing a device having a low driving voltage and high optical efficiency.

In addition, by introducing various substituent groups into the core structure, it is possible to finely control the energy band gap and to improve the characteristics at the interface between the organic materials and to diversify the use of the material.

On the other hand, the compound of formula (1) has a high glass transition temperature (Tg) and is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

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 compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound.

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 layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.

In another embodiment, 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.

In one embodiment of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the 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 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 compound layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound may be included in the light emitting layer.

2 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated In this structure, the compound may be included in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light-emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound 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 benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

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

The electron transporting 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 Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic 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.

≪ Example 1 >

Synthesis Example 1 Preparation of the compound represented by the formula (1-a-1)

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

(39 g, 282 mmol) was dissolved in tetrahydrofuran (THF) (300 mL), and potassium carbonate (K ₂ CO ₃ ) (29 g, 103.5 mmol) Dissolved in water (H ₂ O) (100 ml) and heated to 90 ° 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 purified by column chromatography to obtain the compound of formula 1A (30 g, yield 85%).

MS: [M + H] < + > = 387

(2) Preparation of compound of formula 1B

Formula 1A (18.9g, 48.8mmol) and 1,1,2,2,3,3,4,4,4- nonafluoro as butane-1-sulfonyl fluoride _{(C 4 F 10 O 2 S} ) (10.5 ml and 58.4 mmol) and potassium carbonate (K ₂ CO ₃ ) (20 g, 145 mmol) were dissolved in acetonitrile (300 mL) and heated to 50 ° C. Refluxed for 12 hours, cooled to room temperature and filtered. 1B (30 g, yield 92%) was obtained.

MS: [M + H] < + > = 667

(3) Preparation of formula (1-a-1)

(THF) (300 mL), water (H ₂ O), potassium carbonate (K ₂ CO ₃ ) (9 g, 65.2 mmol), diphenylpyridine boronic acid (6.9 g, 24 mmol) ₂ O) (100 ml) and heated to 90 ° 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 purified by column chromatography to obtain the compound of formula (1-a-1) (10 g, yield 78%).

MS: [M + H] < + > = 612

Synthesis Example 2 Synthesis of the compound represented by the formula (1-a-4)

(1) Preparation of formula (1-a-4)

Except that the compound of the formula 1C (14.6 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 to obtain the compound of the formula 1-a-4 (10 g, Yield: 75%).

MS: [M + H] < + > = 613

Synthesis Example 3 Preparation of a compound represented by the formula (1-a-5)

(1) Preparation of formula (1-a-5)

Except that the compound of the formula 1D (14.9 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 to obtain the compound of the formula 1-a-5 (11 g, Yield: 80%).

MS: [M + H] < + > = 629

Synthesis Example 4 Preparation of a compound represented by the formula (1-a-6)

(1) Preparation of formula (1-a-6)

A-6 (9 g, 21.8 mmol) was prepared in the same manner as in the preparation of the compound of the formula 1-a-6 of the above Synthesis Example 1 except that the compound of the formula 1E (14.6 g, 21.8 mmol) Yield: 68%).

MS: [M + H] < + > = 613

≪ Synthesis Example 5 > Preparation of the compound represented by the formula (1-a-7)

(1) Preparation of formula (1-a-7)

Except that the compound of the formula 1F (14.9 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 in Synthesis Example 1 to obtain the compound of the formula 1-a-7 (9 g, Yield: 66%).

MS: [M + H] < + > = 629

≪ Synthesis Example 6 > Preparation of the compound represented by the formula (1-b-1)

(1) Preparation of formula (1-b-1)

Except that the compound of the formula 1G (14.9 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 to obtain the compound of the formula 1-b-1 (10 g, Yield: 75%).

MS: [M + H] < + > = 612

≪ Synthesis Example 7 > Preparation of the compound represented by the formula (1-c-1)

(1) Preparation of formula (1-c-1)

1-c-1 (8 g, 21.8 mmol) was prepared in the same manner as in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 except that the compound of the formula 1H (14.9 g, 21.8 mmol) Yield: 60%).

MS: [M + H] < + > = 612

Synthesis Example 8 Synthesis of Compound Represented by Formula (1-d-1)

(1) Preparation of formula (1-d-1)

1-d-1 (9 g, 21.8 mmol) was prepared in the same manner as in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 except that the compound of the formula 1I (14.9 g, 21.8 mmol) Yield: 68%).

MS: [M + H] < + > = 612

Synthesis Example 9 Synthesis of the compound represented by the formula (1-e-1)

(1) Preparation of formula (1-e-1)

Except that the compound of the formula 1J (14.9 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 in Synthesis Example 1 to obtain the compound of the formula 1-e-1 (12 g, Yield: 90%).

MS: [M + H] < + > = 612

Synthesis Example 10 Synthesis of Compound Represented by Formula (1-d-7)

(1) Preparation of formula (1-d-7)

Except that the compound of the formula 1K (14.9 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 to obtain the compound of the formula 1-d-7 (9 g, Yield: 66%).

MS: [M + H] < + > = 629

Synthesis Example 10 Synthesis of Compound Represented by Formula (1-d-6)

(1) Preparation of formula (1-d-6)

Except that the compound of the formula 1L (14.9 g, 21.8 mmol) was used instead of the compound of the formula 1B in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 to obtain the compound of the formula 1-d-6 (10 g, Yield: 73%).

MS: [M + H] < + > = 629

Synthesis Example 12 Synthesis of the compound represented by the formula (2-a-8)

(1) Preparation of formula (2A)

(45 g, 103.5 mmol), potassium carbonate (K ₂ CO ₃ ) (39 g, 282 mmol), 7-bromo-2-naphthol (21 g, 94.1 mmol), tetrahydrofuran Dissolved in water (H ₂ O) (100 ml) and heated to 90 ° 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 the compound of formula 2A (40 g, yield 79%).

MS: [M + H] < + > = 539

(2) Preparation of Formula 2B

Formula 2A (26.3g, 48.8mmol) and a 1,1,2,2,3,3,4,4,4- nonafluoro-butane-1-sulfonyl fluoride _{(C 4 F 10 O 2 S} ) (10.5 ml and 58.4 mmol) and potassium carbonate (K ₂ CO ₃ ) (20 g, 145 mmol) were dissolved in acetonitrile (300 mL) and heated to 50 ° C. Refluxed for 12 hours, cooled to room temperature and filtered. 1B (40 g, yield 95%) was obtained.

MS: [M + H] < + > = 821

(3) Preparation of formula (2-a-8)

(9.2g, 47.8mmol), carbazole (10g, 47.8mmol), sodium tetrabutoxide (NaOtBu) (9.2g, 95.6mmol) and xylene (500ml) were mixed and heated to 160 ° C. Pd (pt-Bu ₃ ) ₂ (732 mg, 1.43 mmol) was added thereto, followed by refluxing for 4 hours. After cooling to room temperature, purification was carried out by column chromatography. After drying, the compound of Formula 2-a-8 (25 g, 76%) was obtained.

MS: [M + H] < + > = 688

Synthesis Example 13 Synthesis of the compound represented by the formula (2-e-8)

(1) Preparation of formula (2-e-8)

E-8 (27 g, 47.8 mmol) was prepared in the same manner as in the preparation of the compound of the formula 2-a-8 of the above Synthesis Example 11 except that the compound of the formula 2C (39.2 g, 47.8 mmol) Yield: 85%).

MS: [M + H] < + > = 688

Synthesis Example 14 Synthesis of the compound represented by the formula (2-d-13)

(1) Preparation of formula (2-d-13)

D-13 (29 g, 47.8 mmol) was prepared in the same manner as in the preparation of the compound of the formula 1-a-1 of the above Synthesis Example 1 except that the compound of the formula 2D (39.2 g, 47.8 mmol) Yield: 86%).

MS: [M + H] < + > = 705

≪ 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. A host (H1) and a dopant D1 compound were vacuum-deposited to a thickness of 300 Å as a light emitting layer after vacuum evaporation of the hole transporting material (1) -a-1 (400 Å) synthesized in the above Preparation Example 1. The E1 compound (300 ANGSTROM) was then thermally vacuum deposited sequentially by electron injecting and transporting layers. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium fluoride was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

≪ Example 2 >

The same experiment was carried out as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-a-4 instead of the compound represented by the formula 1-a-1.

≪ Example 3 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-a-5 instead of the compound represented by the formula 1-a-1.

<Example 4>

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-a-6 instead of the compound represented by the formula 1-a-1.

&Lt; Example 5 >

The same experiment was carried out as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-a-7 instead of the compound represented by the formula 1-a-1.

&Lt; Example 6 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-b-1 instead of the compound represented by the formula 1-a-1.

&Lt; Example 7 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound of Formula 1-c-1 instead of the compound of Formula 1-a-1 synthesized in Production Example 1.

&Lt; Example 8 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-d-1 instead of the compound represented by the formula 1-a-1.

&Lt; Example 9 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 1-e-1 instead of the compound represented by the formula 1-a-1.

&Lt; Example 10 >

The same experiment was carried out as in Example 1 except that the hole transport layer was replaced by the compound of Formula 1-d-7 instead of the compound of Formula 1-a-1 synthesized in Preparation Example 1.

&Lt; Example 11 >

The same experiment was carried out as in Example 1 except that the hole transport layer was replaced by the compound of Formula 1-d-6 instead of the compound of Formula 1-a-1 synthesized in Production Example 1. [

&Lt; Example 12 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 2-a-8 instead of the compound represented by the formula 1-a-1.

&Lt; Example 13 >

The same experiment was conducted as in Example 1 except that the hole transport layer was replaced with the compound represented by the formula 2-d-13 instead of the compound represented by the formula 1-a-1.

&Lt; Comparative Example 1 &

The same experiment was carried out as in Example 1 except that HT1 was used instead of the compound 1-a-1 synthesized in the Production Example as the hole transport layer.

&Lt; Comparative Example 2 &

The same experiment was conducted as in Example 1 except that NPB was used instead of the compound represented by Formula 1-a-1, which was synthesized in the Production Example as a hole transport layer.

Table 1 shows the results of the organic light emitting device manufactured using the respective compounds as the hole transporting layer materials as in Examples 1 to 13 and Comparative Examples 1 to 2.

Experimental Example
10 mA / cm 2 Hole transport material Voltage
(V) Current efficiency
(cd / A) Example 1 1-a-1 6.10 7.05 Example 2 1-a-4 6.01 7.05 Example 3 1-a-5 6.02 7.02 Example 4 Formula 1-a-6 6.05 6.88 Example 5 1-a-7 6.01 7.01 Example 6 1-b-1 6.15 6.95 Example 7 1-c-1 6.18 6.89 Example 8 1-d-1 6.10 7.06 Example 9 1-e-1 6.10 7.10 Example 10 1-d-7 6.01 6.55 Example 11 1-d-6 6.10 6.68 Example 12 2-a-8 6.21 6.20 Example 13 2-d-13 6.20 6.99 Comparative Example 1 HT1 6.25 5.98 Comparative Example 2 NPB 6.21 5.87

As can be seen from Table 1, in the case of the organic light emitting device manufactured using the heterocyclic compound according to one embodiment of the present invention as the hole transport layer material, the efficiency, the driving voltage, the stability And exhibits excellent properties in terms of surface area.

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

Claims (15)

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

In formula (1)
L1 is a direct bond; Or an arylene group,
L2 is an arylene group,
Ar1 and Ar2 are the same or different and are each independently a phenyl group; Biphenyl group; Naphthyl group; Or a terphenyl group,
Ar3 is the following formula (2) or (3)
(2)

(3)

In formulas (2) and (3)
X is S or O,
a is an integer of 0 to 8,
b is an integer of 0 to 7,
R1 and R2 are hydrogen. The method according to claim 1,
Wherein the formula 3 is a heterocyclic compound represented by the following formula 3-1 or 3-2:
[Formula 3-1]

[Formula 3-2]

In Formulas (3-1) and (3-2)
X, R2 and b are the same as defined in claim 1. The method according to claim 1,
Lt; 2 &gt; is a phenylene group. delete The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following formulas 1-a, 1-b, 1-c, 1-d, 1-e,
[Chemical Formula 1-a]

[Chemical Formula 1-b]

[Chemical Formula 1-c]

[Chemical formula 1-d]

[Formula 1-e]

[Chemical Formula 1-f]

In the general formulas 1-a, 1-b, 1-c, 1-d, 1-e and 1-f,
L1, L2, Ar1, Ar2 and Ar3 are the same as defined in claim 1. The method according to claim 1,
L1 is a direct bond; Or a phenylene group,
L2 is a phenylene group,
Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; Biphenyl group; Naphthyl group; Or a terphenyl group. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by the following formulas 1-a-1 to 1-a-17, 1-b-1 to 1-b-17, 1-c-1 to 1-c- a heterocyclic compound represented by any one of the following formulas: d-1 to 1-d-17, 1-e-1 to 1-e-17 and 1-f-

. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is represented by the following formulas 2-a-1 to 2-a-17, 2-b-1 to 2-b-17, 2-c-1 to 2- a heterocyclic compound represented by any one of the following formulas: d-1 to 2-d-17, 2-e-1 to 2-e-17 and 2-f-

. 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 is a heterocyclic compound according to any one of claims 1 to 3 and 5 to 8, And an organic light emitting layer. The method of claim 9,
Wherein the organic material layer includes a hole injection layer or a hole transport layer,
Wherein the hole injection layer or the hole transport layer comprises the heterocyclic compound. The method of claim 9,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the heterocyclic compound as a host of the light emitting layer. The method of claim 9,
Wherein the organic material layer includes an electron transport layer or an electron injection layer,
Wherein the electron transport layer or the electron injection layer comprises the heterocyclic compound. The method of claim 9,
Wherein the organic material layer further comprises 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 containing the heterocyclic compound. The method of claim 9,
Wherein 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. The method of claim 9,
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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