KR20190098079A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting device comprising the same. The heterocyclic compound according to an embodiment of the present specification can be used as a material of an organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.

Description

Heterocyclic compound and organic light-emitting device including the same TECHNICAL FIELD

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2018-0017478, filed with the Korea Intellectual Property Office on February 13, 2018, the entire contents of which are incorporated herein.

The present specification relates to a heterocyclic compound and an organic light emitting device formed using the heterocyclic compound.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

US Patent Application Publication No. 2004-0251816

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

According to an exemplary embodiment of the present specification provides a heterocyclic compound represented by the formula (1).

[Formula 1]

In Chemical Formula 1

X is O or S,

A1 and A2 are the same as or different from each other, and each independently substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted Or an unsubstituted dialkylarylsilyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic group. To form a ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle,

L1 and L2 are the same as or different from each other, and each independently a direct bond or an arylene group,

R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,

a is an integer of 0 to 3,

b is 0 or 1,

n is an integer from 0 to 2,

m is an integer from 0 to 4,

a + m≤4

b + n ≦ 2,

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

When m is plural,-(L1-A1) is the same as or different from each other,

When n is plural,-(L2-A2) is the same as or different from each other.

Finally, the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound.

The heterocyclic compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.

More specifically, the compound according to the exemplary embodiment of the present invention has a high electron accepting structure, has a delayed fluorescent property, and can maintain an appropriate deposition temperature when fabricating an organic light emitting device. In addition, it is possible to increase the purity by the sublimation purification method, and does not cause contamination in the deposition film forming apparatus or the organic light emitting device when manufacturing the organic light emitting device.

1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a heterocyclic compound represented by Chemical Formula 1.

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when 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 a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Nitrile group; Halogen group; Boron group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted carbonyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In the present specification, the alkyl group may be linear or branched chain, carbon number 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-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, 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, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention 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, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. 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 so on. 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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. 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 aryl group in the aryloxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the aryl group described above. Specifically, the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-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, 9-phenanthryloxy group, and the like.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), isooxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, 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 including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

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 heteroaryl group described above.

In this specification, arylene is the same as the example of the aryl group mentioned above except that it is bivalent.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following formula (2) and formula (3).

[Formula 2]

[Formula 3]

In Formulas 2 and 3, the definitions of X, A1, A2, L1, L2, R1, R2, a, b, m and n are the same as defined in Formula 1 above,

A11 to A14 are the same as the definitions of A1,

L11 to L14 are the same as the definition of L1,

A21 and A22 are the same as defined in A2,

L21 and L22 are the same as the definitions of L2.

According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the compounds of Formulas 4 to 11.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

In Chemical Formulas 4 and 11, the definition of X is as defined in Chemical Formula 1,

A11 to A14 are the same as the definitions of A1,

L11 to L14 are the same as the definition of L1,

A21 and A22 are the same as defined in A2,

L21 and L22 are the same as the definitions of L2.

According to an exemplary embodiment of the present specification, m + n≥1.

According to an exemplary embodiment of the present specification, the A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted Arylamine group.

According to an exemplary embodiment of the present specification, the A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number It is a heteroaryl group of 3-30, or a substituted or unsubstituted arylamine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently deuterium, nitrile group, halogen group, aryl group, heteroaryl group, silyl group, boron And an aryl group unsubstituted or substituted with a substituent selected from a group, an alkenyl group, a carbonyl group, a phosphine oxide group, and an amine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently represent an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms It is a C6-C30 aryl group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently a methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, pen Substituted or unsubstituted with a methyl group, hexyl group, cyclohexyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, quarterphenyl group, phenanthrene group, anthracene group, pyrene group, triphenylene group, fluorene group, or spirobifluorene group Aryl group having 6 to 30 ring carbon atoms.

According to an exemplary embodiment of the present specification, the A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, the substituted or unsubstituted An aryl group having 6 to 30 carbon atoms is a phenyl group; Naphthyl group; Biphenyl group; Terphenyl group; Quarter-phenyl group; Phenanthrene group; Anthracene groups; Pyrene group; Triphenylene group; Fluorene group; And spirobifluorene groups, but is not limited thereto.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently a nitrile group, a halogen group, an alkyl group, an aryl group, a heteroaryl group, a silyl group, and boron And a heteroaryl group unsubstituted or substituted with a substituent selected from a group, an alkenyl group, a carbonyl group, a phosphine oxide group, and an amine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently a nitrile group, a halogen group, an alkyl group, an aryl group, a heteroaryl group, a silyl group, and boron And a heteroaryl group having 3 to 30 carbon atoms containing at least one of N, O, and S unsubstituted or substituted with a substituent selected from a group, an alkenyl group, a carbonyl group, a phosphine oxide group, and an amine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms Monocyclic or polycyclic heteroaryl group containing one or more of N, O, and S,

The monocyclic or polycyclic heteroaryl group may be a pyrrole group, a pyridine group, a pyrimidine group, a triadine group, a carbazole group, an imidazole group, a pyrrole group, a quinazol group, a quinoline group, a furan group, a benzofuran group, a dibenzofuran group, a benzo It may be selected from naphthofuran group, thiophene group, benzothiophene group, dibenzothiophene group, and benzonaphthothiophene group, but is not limited thereto.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The carbazole group, dibenzofuran group, or dibenzothiophene group may be substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently deuterium, nitrile group, halogen group, aryl group, heteroaryl group, silyl group, boron And an arylamine group unsubstituted or substituted with a substituent selected from a group, an alkenyl group, a carbonyl group, a phosphine oxide group, and an amine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently substituted or unsubstituted with a deuterium, nitrile group, halogen group, aryl group, or heteroaryl group Arylamine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently substituted with an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms or It is an unsubstituted arylamine group.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently a monocyclic aryl group having 6 to 30 carbon atoms, and a polycyclic aryl group having 6 to 30 carbon atoms. , An arylamine group unsubstituted or substituted with a monocyclic heteroaryl group having 6 to 30 carbon atoms or a polycyclic heteroaryl group having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A1, A2, A11 to A14, A21 and A22 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, terbutyl group, or carbazole group; Naphthyl group; Carbazole groups unsubstituted or substituted with a phenyl group or a terbutyl group; Dibenzofuran group; Dibenzothiophene group; Diphenyl fluorene group; Dimethyl fluorene group; Spirobifluorene; Or a diphenylamine group.

According to an exemplary embodiment of the present specification, L1, L2, L11 to L14, L21 and L22 are the same as or different from each other, and each independently a direct bond, or an arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1, L2, L11 to L14, L21 and L22 are the same as or different from each other, and each independently a divalent phenyl group, a divalent biphenylene group, a divalent terphenylene group, a divalent pephenyl It is a nanthrene group, a bivalent anthracene group, or a bivalent triphenylene group.

According to an exemplary embodiment of the present specification, L1, L2, L11 to L14, L21 and L22 are the same as or different from each other, and each independently a direct bond or a phenylene group.

According to an exemplary embodiment of the present specification, m is 1, n is 0.

According to an exemplary embodiment of the present specification, m is 2, n is 0.

According to an exemplary embodiment of the present specification, m is 4, n is 0.

According to an exemplary embodiment of the present specification, n is 1, m is 0.

According to an exemplary embodiment of the present specification, n is 2, m is 0.

According to yet an embodiment of the present disclosure, the heterocyclic compound of Formula 1 may be represented by any one selected from the following structural formula.

In addition, the organic light emitting device according to the present invention comprises a first electrode; A second electrode provided to face the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described 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 injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like 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 material layers. In addition, the organic material layer may include one or more layers of an electron transport layer, an electron injection layer, and a layer for simultaneously transporting and transporting electrons, and one or more of the layers may include the compound.

The organic material layer including the heterocyclic compound of Formula 1 may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in 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 is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, a light emitting layer 4, and a second electrode 5 are sequentially stacked on a substrate 1.

2, the first electrode 2, the hole injection layer 6, the hole transport layer 7, the electron blocking layer 8, the light emitting layer 4, the hole blocking layer 9, the electron injection and transport layer 10, and The structure of the organic light emitting element in which the second electrode 5 is sequentially stacked is illustrated. Preferably, the heterocyclic compound of Formula 1 is included in the emission layer.

1 and 2 illustrate an organic light emitting diode and are not limited thereto.

In the description of the present invention, the organic light emitting device includes a structure in which a first electrode / light emitting layer / second electrode is sequentially stacked.

In the description of the present invention, the organic light emitting device includes a structure in which a first electrode / hole transport layer / electron suppression layer / light emitting layer / second electrode is sequentially stacked.

In the specification of the present invention, the organic light emitting device includes a structure in which a first electrode / hole injection layer / hole transport layer / light emitting layer / second electrode is sequentially stacked.

In the description of the present invention, the organic light emitting device includes a structure in which the first electrode / hole injection layer / hole transport layer / light emitting layer / electron injection and transport layer / second electrode are sequentially stacked.

In the specification of the present invention, the organic light emitting device includes a structure in which the first electrode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / electron injection and transport layer / second electrode are sequentially stacked.

In the specification of the present invention, the organic light emitting device includes a structure in which the first electrode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / hole suppression layer / electron injection and transport layer / second electrode are sequentially stacked.

In an exemplary embodiment of the present invention, the organic light emitting device may include a light emitting layer, and the light emitting layer may include a heterocyclic compound of Chemical Formula 1.

In one embodiment of the present invention, the organic light emitting device comprises a heterocyclic compound of Formula 1 in the light emitting layer as a dopant of the light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes an organic compound in the light emitting layer as a host of the light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes a heterocyclic compound in the light emitting layer as a host of the light emitting layer.

In an exemplary embodiment of the present invention, the organic light emitting device includes an N-containing heterocyclic compound as a host of the light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes a carbazole compound in the light emitting layer as a host of the light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes a carbazole compound in the light emitting layer as a host of the light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes a host and a dopant in a weight ratio of 90:10 to 10:90 in the light emitting layer.

In an exemplary embodiment of the present invention, the organic light emitting diode includes a host and a dopant in a light emitting layer in a weight ratio of 80:20 to 50:50.

In an exemplary embodiment of the present invention, the organic light emitting device includes a host and a dopant in a weight ratio of 80:20 to 60:40 in the light emitting layer.

In an exemplary embodiment of the present invention, the organic light emitting device includes an electron injection layer, an electron transport layer, or a hole blocking layer, and the heterocyclic compound of Formula 1 is added to the electron injection layer, the electron transport layer, or the hole blocking layer. It may include.

In one embodiment of the present invention, the organic light emitting device comprises a hole injection layer, a hole transport layer, or an electron blocking layer, the hole injection layer, a hole transport layer, or an electron blocking layer in the heterocyclic compound of Formula 1 It may include.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. To form an anode and to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an organic material layer containing a heterocyclic compound of the formula (1), and then used as a cathode thereon It can be prepared by depositing. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode 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), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; 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 containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include heterocyclic compounds, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, an anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

The electron injection layer is a layer that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer for preventing the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.

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

According to an exemplary embodiment of the present specification, the compound of Formula 1 may be prepared according to the following reaction scheme, but is not limited thereto. In the following schemes, the type and number of substituents can synthesize various kinds of intermediates as those skilled in the art appropriately select known starting materials. Reaction type and reaction conditions may be used those known in the art.

Proper combination of the formulas described in the examples herein and the intermediates based on common technical knowledge can produce all of the compounds of Formula 1 described herein.

< Production Example >

The compound represented by Chemical Formula 1 may be prepared from a process of forming a ring by introducing various types of benzene into benzene substituted with a halide as follows. After introducing cyanide, compounds were synthesized by finally introducing carbazole, heteroaryl, and aryl.

Production Example  1-1: Synthesis of Compound 1-A

30 g (217.5 mmol) of (2-hydroxyphenyl) boronic acid, 217.5 mmol of 1,3,5-tribromo-2,4,6-trifluorobenzene, 200 mL of tetrahydrofuran and 100 mL of water were mixed and 60 ° C. Heated to. Potassium carbonate (652.5 mmol) and tetrakistriphenylphosphinepalladium (1 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 74.7 g of Compound 1-A (yield 90%).

MS [M + H] &lt; + &gt; = 381

Production Example  1-2: Synthesis of Compound 1-B

50 g (130.9 mmol) of 1-A, 262 mmol of potassium carbonate and 300 mL of DM were mixed, heated to 60 ° C for 1 hour, and stirred for 1 hour in a reflux state. After the reaction, the reaction solution returned to room temperature was counterprecipitated with water to obtain a solid, and then recrystallized twice with TF and ethanol to give 38.8 g of compound 1-B (yield 82%).

MS [M + H] &lt; + &gt; = 361

Production Example  1-3: Synthesis of Compound 1-C

35 g (96.7 mmol) of 1-B, 386 mmol of cupper cyanide and 300 mL of DM were mixed and stirred at 100 ° C. for 4 hours. The reaction solution returned to room temperature after the reaction was counterprecipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to give 18.7 g of Compound 1-C (yield 76%).

MS [M + H] + = 255

Production Example  1-4: Synthesis of Compound 1-D

15-g (59 mmol) of 1-C, 59 mmol of 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole, 118 mmol of potassium carbonate and 100 mL of DM were mixed and stirred at 80 ° C for 1 hour. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to obtain Compound 1-D 28g (84% yield).

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

Production Example  1-5: Synthesis of Compound 1

15 g (59 mmol) of 1-C, 118 mmol of 9-H-carbazole, 236 mmol of potassium carbonate and 100 mL of DMMP were mixed and stirred at 100 ° C. for 2 hours. The reaction solution returned to room temperature after the reaction was counterprecipitated with water to obtain a solid, and then recrystallized twice with TF and ethanol to give 26.2 g of compound 1 (yield 81%).

MS [M + H] &lt; + &gt; = 549

Production Example  1-6: Synthesis of Compound 2

15 g (26.5 mmol) of 1-D, 26.5 mmol of 9-H-carbazole, 118 mmol of potassium carbonate, and 100 mL of DMMP were mixed and stirred at 100 ° C. for 1 hour. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to obtain 15.7 g of compound 2 (yield 83%).

MS [M + H] &lt; + &gt; = 714

Production Example  2-1: Synthesis of Compound 2-A

37.6 g (217.5 mmol) of 2-bromophenol, 217.5 mmol (perfluorophenyl) boronic acid, 200 mL of tetrahydrofuran and 100 mL of water were mixed and heated to 60 ° C. Potassium carbonate (652.5 mmol) and tetrakistriphenylphosphinepalladium (1 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice with chloroform and hexane to give 51.5 g of compound 2-A (yield 91%).

MS [M + H] &lt; + &gt; = 261

Production Example  2-2: Synthesis of Compound 2-B

34 g (130.9 mmol) of 1-A and 300 mL of DM were mixed and stirred for 1 hour after adding 130.9 mmol of NBS at 0 ° C. After the reaction, the reaction solution was counterprecipitated in aqueous sodium thiosulphate solution to obtain a solid, and then recrystallized twice with TF and hexane to give 48.1 g of the compound 2-B (yield 88%).

MS [M + H] &lt; + &gt; = 416

Production Example  2-3: Synthesis of Compound 2-C

40 g (95.7 mmol) of 2-B, 192 mmol of potassium carbonate and 300 mL of DM were mixed, heated to 60 ° C for 1 hour, and stirred for 1 hour in a reflux state. The reaction solution returned to room temperature after the reaction was counterprecipitated with water to obtain a solid, and then recrystallized twice with TF and ethanol to give 30.8 g of compound 2-C (yield 81%).

MS [M + H] &lt; + &gt; = 396

Production Example  2-4: Synthesis of Compound 2-D

2-C 25g (62.8mmol), cupper cyanide 125.6mmol, DMF 200mL were mixed, and it stirred at 100 degreeC for 4 hours. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to obtain 13.3 g of compound 2-D (yield 73%).

MS [M + H] &lt; + &gt; = 291

Production Example  2-5: Synthesis of Compound 3

2-D 12g (41.3mmol), 9-H-carbazole 165.4mmol, potassium carbonate 330.8mmol, DMF 100mL were mixed, and it stirred at 100 degreeC for 2 hours. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to give 28 g of compound 3 (yield 77%).

MS [M + H] &lt; + &gt; = 879

Production Example  2-6: Synthesis of Compound 4

2-D 12g (41.3mmol), 3,6-dimethyl-9-H-carbazole 165.4mmol, potassium carbonate 330.8mmol, DMF 100mL were mixed, and it stirred at 100 degreeC for 2 hours. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to obtain 30.7 g of compound 4 (yield 75%).

MS [M + H] &lt; + &gt; = 991

Production Example  3-1: Synthesis of Compound 3-A

33.5 g (217.5 mmol) of (2-mercamptophenyl) boronic acid, 217.5 mmol of 1,3,5-tribromo-2,4,6-trifluorobenzene, 200 mL of tetrahydrofuran and 100 mL of water were mixed and 60 Heated to ° C. Potassium carbonate (652.5 mmol) and tetrakistriphenylphosphinepalladium (1 mmol) were added and the mixture was stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then recrystallized twice from chloroform and hexane to give 77 g of compound 3-A (yield 89%).

MS [M + H] &lt; + &gt; = 396

Production Example  3-2: Synthesis of Compound 3-B

52 g (130.9 mmol) of 3-A, 262 mmol of potassium carbonate and 300 mL of DM were mixed, heated to 60 ° C. for 1 hour, and stirred for 1 hour under reflux. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to give 39.6 g of compound 3-B (yield 80%).

MS [M + H] &lt; + &gt; = 376

Production Example  3-3: Synthesis of Compound 3-C

36.5 g (96.7 mmol) of 3-B, 386 mmol of cupper cyanide and 300 mL of DM were mixed and stirred at 100 ° C. for 4 hours. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to give 19.8 g of compound 3-C (yield 76%).

MS [M + H] &lt; + &gt; = 271

Production Example  3-4: Synthesis of Compound 3-D

3-C 15.9g (59mmol), 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole 59mmol, potassium carbonate 118mmol, DMF 100mL were mixed and stirred at 80 ° C for 1 hour. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to obtain 27.8 g of compound 3-D (yield 81%).

MS [M + H] &lt; + &gt; = 583

Production Example  3-5: Synthesis of Compound 5

3-C 15.9g (59mmol), 9-H-carbazole 118mmol, potassium carbonate 236mmol, DMF 100mL were mixed and stirred at 100 ° C for 2 hours. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to obtain 27.6 g of compound 5 (yield 83%).

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

Production Example  3-6: Synthesis of Compound 6

3-D 15.4g (26.5mmol), 9-H-carbazole 26.5mmol, potassium carbonate 118mmol, DMF 100mL were mixed, and it stirred at 100 degreeC for 1 hour. After the reaction, the reaction solution returned to room temperature was reversely precipitated in water to obtain a solid, and then recrystallized twice with TF and ethanol to give 15.6 g of compound 6 (yield 81%).

MS [M + H] &lt; + &gt; = 730

Using the same reaction scheme as described above, various kinds of substituents were introduced to synthesize materials of the exemplary embodiments.

< Example >

In the present embodiment, the compound represented by Formula 1 according to the exemplary embodiment of the present specification is included in a light emitting layer with a host material (m-CBP) having a triplet value of 2.5 eV or more, to manufacture an organic light emitting device, and characteristics Evaluated.

[ Comparative example  One]

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. Each thin film was deposited on the ITO transparent electrode thus prepared at a vacuum degree of 5.0 Х 10 ^-4 Pa by vacuum deposition. First, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited to a thickness of 500 kPa on ITO to form a hole injection layer.

Compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 Pa), which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. It was.

The compound N-([1,1'-bisphenyl] -4-yl) -N- (4- (11-([1,1'-biphenyl] -4-yl) having a film thickness of 100 kPa on the hole transport layer ) -11H-benzo [a] carbazole-5-yl) phenyl)-[1,1'-biphenyl] -4-amine (EB1) (100 Pa) was vacuum deposited to form an electron blocking layer.

Subsequently, the following m-CBP and the compound 4CzIPN were vacuum-deposited at a weight ratio of 70:30 on the electron blocking layer with a film thickness of 300 Pa to form a light emitting layer.

Compound HB1 was vacuum deposited on the light emitting layer at a film thickness of 100 Pa to form a hole blocking layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 Å. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited sequentially to have a thickness of 12 kW to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at the deposition rate of 0.3 은 / sec, aluminum was 2 Å / sec, the vacuum degree during deposition is 2 ⅹ 10 ^-7 An organic light emitting device was manufactured by maintaining ˜5 × 10 ⁻⁶ torr.

Experimental Examples 1 to 6

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound of Table 1 instead of the compound 4CzIPN in Comparative Example 1.

[Comparative Examples 2 and 3]

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound of T1 to T2 instead of the compound 4CzIPN in Comparative Example 1.

When the current was applied to the organic light emitting diodes produced by Experimental Examples 1 to 6 and Comparative Examples 1 to 3, the results of the following [Table 1] were obtained.

division compound
(Light emitting layer) Voltage
(V @ 10mA / cm ² ) efficiency
(cd / A @ 10mA / cm ² ) Color coordinates
(x, y) Comparative Example 1 4CzIPN 4.4 16 (0.33, 0.62) Experimental Example 1 Compound 1 4.0 23 (0.34, 0.64) Experimental Example 2 Compound 2 4.1 22 (0.33, 0.65) Experimental Example 3 Compound 3 4.1 23 (0.33, 0.66) Experimental Example 4 Compound 4 4.0 23 (0.33, 0.65) Experimental Example 5 Compound 5 3.9 22 (0.32, 0.64) Experimental Example 6 Compound 6 3.9 23 (0.33, 0.64) Comparative Example 2 T1 4.8 One (0.21, 0.25) Comparative Example 3 T2 4.7 2 (0.27, 0.28)

As shown in Table 1, the devices of Experimental Examples 1 to 6 using the compound having the structure of Formula 1 as a core have lower voltages and higher efficiency than devices using 4CzIPN. Comparative Example 2 Comparing the device of the present invention with the device of Comparative Example 3 and the position of the carbazole in which the nitrile group is substituted, it can be seen that the structure of the embodiments of the present application is improved both in terms of voltage and efficiency.

As shown in Table 1, the compound according to the present invention was confirmed that the excellent light emitting ability and high color purity can be applied to the delayed fluorescent organic light emitting device.

1: substrate
2: first electrode
3: organic material layer
4: light emitting layer
5: second electrode
6: hole injection layer
7: hole transport layer
8: electronic jersey
9: hole blocking layer
10: electron injection and transport layer

Claims (9)

Heterocyclic compounds represented by the formula (1):
[Formula 1]

In Chemical Formula 1
X is O or S,
A1 and A2 are the same as or different from each other, and each independently substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted Or an unsubstituted dialkylarylsilyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic group. To form a ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle,
L1 and L2 are the same as or different from each other, and each independently a direct bond or an arylene group,
R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
a is an integer of 0 to 3,
b is 0 or 1,
n is an integer from 0 to 2,
m is an integer from 0 to 4,
a + m≤4
b + n ≦ 2,
When a is plural, R1 is the same as or different from each other,
When m is plural,-(L1-A1) is the same as or different from each other,
When n is plural,-(L2-A2) is the same as or different from each other. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 2 and 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3, the definitions of X, A1, A2, L1, L2, R1, R2, a, b, m and n are the same as defined in Formula 1 above,
A11 to A14 are the same as the definition of A1,
L11 to L14 are as defined in the above L1,
A21 and A22 are as defined in A2 above,
L21 and L22 are the same as the definition of L2. The method according to claim 1, wherein A1 and A2 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or substituted or unsubstituted Heterocyclic compound which is a substituted arylamine group. The heterocyclic compound according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond or an arylene group having 6 to 30 carbon atoms. The heterocyclic compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound according to any one of claims 1 to 5. Phosphorescent organic light-emitting device. The organic light emitting device of claim 6, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound. The organic light emitting device of claim 6, wherein the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the heterocyclic compound. The organic light emitting device of claim 6, wherein the organic material layer includes an electron injection layer, an electron transport layer, or a hole blocking layer, and the electron injection layer, an electron transport layer, or a hole blocking layer includes the heterocyclic compound.

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