KR102564940B1 - Heterocyclic compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light emitting device including the same.

Description

Heterocyclic compound and an organic light emitting device including the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted 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. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

Development of new materials for the organic light emitting device as described above has been continuously demanded.

US Patent Application Publication No. 2004-0251816

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

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

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group,

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

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R3 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r3 is an integer from 1 to 4, and when r3 is 2 or more, two or more R3s are the same as or different from each other;

r4 is an integer from 1 to 3, and when r4 is 2 or more, two or more R4s are the same as or different from each other;

2 ≤ r3+ r4 ≤ 6;

r5 is an integer from 1 to 3, and when r5 is 2 or more, two or more R5s are the same as or different from each other;

r6 is an integer from 1 to 4, and when r6 is 2 or more, two or more R6s are the same as or different from each other;

2 ≤ r5 + r6 ≤ 6.

In addition, 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 the one or more organic material layers include the heterocyclic compound.

The heterocyclic compound according to an exemplary embodiment of the present specification may be used in an organic light emitting device to lower a driving voltage of the organic light emitting device and improve light efficiency. In addition, the lifespan characteristics of the small intestine can be improved by the thermal stability of the heterocyclic compound.

1 to 4 illustrate an example of an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification will be described in more detail.

The heterocyclic compound according to an exemplary embodiment of the present specification is a compound including two amine groups and R1 and R2 as substituents in a core in which two indolocarbazoles are condensed, and has structural stability. Therefore, an organic light emitting device including the organic light emitting device has an advantage in driving efficiency, and since the heterocyclic compound has a condensed ring structure, it has a long lifespan. In addition, since R1 and R2 of Chemical Formula 1 include the above substituents, there is an advantage in that the organic light emitting device is easy to handle during the manufacturing process even when the molecular weight increases.

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

In this specification, indicates the connecting part.

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

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; haloalkyl group; silyl group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of heteroaryl groups, is substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or does not have any substituents.

In the present specification, two or more substituents are linked means that the hydrogen of any one substituent is linked to another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected. or can be a substituent of In addition, the three substituents are connected not only by connecting (substituent 1)-(substituent 2)-(substituent 3) in succession, but also by connecting (substituent 2) and (substituent 3) to (substituent 1). include For example, a phenyl group, a naphthyl group and an isopropyl group are connected, , or can be a substituent of The above definition is equally applied to the case where 4 or more substituents are connected.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-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, etc., 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, etc., but are limited thereto It is not.

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.

In the present specification, the haloalkyl group means that at least one halogen group is substituted for the hydrogen of the alkyl group in the definition of the alkyl group.

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is 10-30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

In the present specification, the fluorene group may be substituted, and adjacent groups may bond to each other to form a ring.

When the fluorene group is substituted, , , , , , , and etc., but is not limited thereto.

As used herein, "adjacent" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. can For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the heteroaryl group includes at least one atom or heteroatom other than carbon, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, and an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine group), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene Thioxanthene group and the like, but is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, and the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group, and examples of the heteroaryl group of the heteroarylsilyl group may be applied.

In the present specification, the amine group is selected from the group consisting of -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms 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, and a 9-methyl-anthracenylamine group. , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthreate Nyl fluorenyl amine group, N-biphenyl fluorenyl amine group and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-mentioned alkyl group and heteroaryl group.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched-chain alkyl group. The alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched-chain alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from examples of the aforementioned alkyl groups.

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

In the present specification, the arylene group means that the aryl group has two binding sites, that is, a divalent group. The description of the aryl group described above can be applied except that each is a divalent group.

In the present specification, the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. The above description of the heteroaryl group may be applied except that each is a divalent group.

Hereinafter, the heterocyclic compound represented by Formula 1 will be described in detail.

According to an exemplary embodiment of the present specification, in Formula 1, R3 to R6 are hydrogen.

According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 1-1 below.

[Formula 1-1]

In Formula 1-1,

The definitions of R1, R2, L1, L2 and Ar1 to Ar4 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, in Formula 1, L1 and L2 are direct bonds.

According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 1-2 below.

[Formula 1-2]

In Formula 1-2,

The definitions of R1, R2 and Ar1 to Ar4 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represent a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represent a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 3 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms, unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or an isopropyl group unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other and are a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other and are a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other and are a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other and are a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 3 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other, and are a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other and are a linear or branched chain alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other, and are a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other, and are a straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other, and are a straight-chain or branched-chain alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as each other, and a methyl group unsubstituted or substituted with deuterium; Or an isopropyl group unsubstituted or substituted with heavy hydrogen.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a linear or branched chain alkyl group having 1 to 30 carbon atoms, and carbon atoms A carbon number unsubstituted or substituted with one or more substituents selected from the group consisting of a linear or branched alkylsilyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms 6 to 30 monocyclic or polycyclic aryl groups; Or a straight chain or branched chain alkyl group having 1 to 30 carbon atoms, a linear or branched chain alkylsilyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and a linear or branched chain alkyl group having 1 to 30 carbon atoms. It is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted with one or more substituents selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted with .

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a linear or branched chain alkyl group having 1 to 20 carbon atoms, a carbon number Carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of a linear or branched alkylsilyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms 6 to 20 monocyclic or polycyclic aryl groups; Or a straight chain or branched chain alkyl group having 1 to 20 carbon atoms, a linear or branched chain alkylsilyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, and a linear or branched chain alkyl group having 1 to 20 carbon atoms. It is a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, substituted or unsubstituted with one or more substituents selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted with .

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently represents a halogen group, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and 1 to 30 carbon atoms. A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a 30 linear or branched chain alkylsilyl group, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group unsubstituted or substituted with a linear or branched chain alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A straight chain or branched chain alkyl group having 1 to 30 carbon atoms, a straight chain or branched chain alkylsilyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and a linear or branched chain alkyl group having 1 to 30 carbon atoms a dibenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently represents a halogen group, a cyano group, a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms. A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a 20 linear or branched alkylsilyl group, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with a linear or branched chain alkyl group having 1 to 20 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; terphenyl group; A fluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; A straight chain or branched chain alkyl group having 1 to 20 carbon atoms, a straight chain or branched chain alkylsilyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, and a linear or branched chain alkyl group having 1 to 20 carbon atoms. a dibenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 to Ar4 are the same as or different from each other, and each independently fluorine (fluoro group), cyano group, methyl group, isopropyl group, tert-butyl group, A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclohexyl group, a trimethylsilyl group and a phenyl group; A biphenyl group unsubstituted or substituted with a methyl group or a phenyl group; terphenyl group; A fluorene group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a trimethylsilyl group, and a phenyl group unsubstituted or substituted with a methyl group; or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

In the above compound, Me means a methyl group.

The present specification provides an organic light emitting device including the aforementioned compound.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In this specification, when a part is said to "include" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.

In the present specification, the 'layer' means compatible with 'film' mainly used in the art, and means a coating covering a target area. The size of the 'layer' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of a 'layer' may be the same as the size of an entire device, may correspond to the size of a specific functional region, or may be as small as a single sub-pixel.

In this specification, the meaning that a specific material A is included in the B layer means that i) one or more types of material A are included in one layer B, and ii) the layer B is composed of one or more layers, and the material A is a multi-layer B All of the layers included in one or more layers are included.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means that i) included in one or more of the one or more C layers, ii) included in one or more of the one or more D layers, or iii ) means all of those included in one or more C layers and one or more D layers, respectively.

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 at least one of the organic material layers includes the heterocyclic compound represented by Chemical Formula 1. provides

According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Chemical Formula 1.

According to one embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a dopant material, and the dopant material includes a heterocyclic compound represented by Chemical Formula 1.

An organic light emitting device according to the present specification may include an additional organic material layer in addition to the light emitting layer.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, it 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, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.

An organic light emitting device according to an exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

L21 to L23 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

l21 is an integer from 1 to 3, and when l21 is 2 or more, two or more L21s are the same as or different from each other;

l22 is an integer from 1 to 3, and when l22 is 2 or more, two or more L22s are the same as or different from each other;

l23 is an integer from 1 to 3, and when l23 is 2 or more, two or more L23s are the same as or different from each other,

a is 0 or 1;

According to an exemplary embodiment of the present specification, in Chemical Formula 2, 1% to 100% of substitutable positions are substituted with deuterium.

In this specification, 'deuterated', 'substituted with deuterium', or 'comprising deuterium' means that at least one substitutable H (hydrogen) is replaced with D (deuterium). 'x% deuterated', 'substituted with x% deuterium', or 'comprising x% deuterium' means that deuterium is present at 100 times or more of the natural abundance level of hydrogen at a substitutable position in Formula 2 above. .

In the present specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy ( ¹ H NMR), TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), or GC/MS (Gas Chromatography/Mass Spectrometry).

According to an exemplary embodiment of the present specification, when a is 0, the position of -L23-Ar23 is hydrogen.

According to an exemplary embodiment of the present specification, a is 0.

According to an exemplary embodiment of the present specification, a is 1.

According to an exemplary embodiment of the present specification, in Formula 2, R21 to R27 are hydrogen.

According to an exemplary embodiment of the present specification, Formula 2 is represented by Formula 2-1 or 2-2 below.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

The definitions of L21 to L23, l21 to l23 and Ar21 to Ar23 are the same as defined in Chemical Formula 2 above.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, l21 is 1.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, l22 is 1.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, l23 is 1.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, l21 is 2, and two L21s are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, l22 is 2, and two L22s are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Chemical Formula 2, l23 is 2, and two L23s are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, a linear or branched chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, unsubstituted or substituted with heavy hydrogen, a linear or branched chain alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Biphenylylene group; naphthylene group; divalent anthracene; A divalent fluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a divalent carbazole group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenylylene group; naphthylene group; divalent anthracene; A divalent fluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; or a divalent carbazole group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, L21 to L23 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen or a phenyl group; a biphenylylene group; naphthylene group; divalent anthracene; A divalent fluorene group unsubstituted or substituted with a methyl group; or a divalent carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, Ar21 to Ar23 are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, a straight chain or branched chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, Ar21 to Ar23 are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, a straight chain or branched chain alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, the Ar21 to Ar23 are the same as or different from each other, and each independently a methyl group; tert-butyl group; A phenyl group unsubstituted or substituted with heavy hydrogen, a straight or branched chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; biphenyl group; naphthyl group; phenanthrene group; terphenyl group; a fluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A benzofluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; Benzophenanthrene group; benzanthracene group; triphenylene group; Benzochrysen group; Spirobifluorene group; Dibenzofuran group; benzonaphthofuran group; Benzobisbenzofuran group; Dibenzothiophene group; benzonaphthothiophene group; or a carbazole group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, the Ar21 to Ar23 are the same as or different from each other, and each independently a methyl group; tert-butyl group; A phenyl group unsubstituted or substituted with heavy hydrogen, a straight or branched chain alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl group; naphthyl group; phenanthrene group; terphenyl group; a fluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A benzofluorene group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Benzophenanthrene group; benzanthracene group; triphenylene group; Benzochrysen group; Spirobifluorene group; Dibenzofuran group; benzonaphthofuran group; Benzobisbenzofuran group; Dibenzothiophene group; benzonaphthothiophene group; or a carbazole group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 2, the Ar21 to Ar23 are the same as or different from each other, and each independently a methyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a deuterium, methyl group, or phenyl group; biphenyl group; naphthyl group; phenanthrene group; terphenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group; Benzophenanthrene group; benzanthracene group; triphenylene group; Benzochrysen group; Spirobifluorene group; Dibenzofuran group; benzonaphthofuran group; Benzobisbenzofuran group; Dibenzothiophene group; benzonaphthothiophene group; or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Formula 2 is selected from the following compounds.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes a compound represented by Chemical Formula 2.

An organic light emitting device according to an exemplary embodiment of the present specification includes a light emitting layer, wherein the light emitting layer includes the heterocyclic compound represented by Chemical Formula 1 as a dopant of the light emitting layer, and the compound represented by Chemical Formula 2 as a host of the light emitting layer. do.

According to an exemplary embodiment of the present specification, based on 100 parts by weight of the compound represented by Formula 2, the content of the heterocyclic compound represented by Formula 1 is 0.01 part by weight to 30 parts by weight; 0.1 part by weight to 20 parts by weight; or 0.5 parts by weight to 10 parts by weight.

According to one embodiment of the present specification, the light emitting layer may include one more host material in addition to the compound represented by Chemical Formula 2. At this time, the further included host material (mixed host compound) includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives and the like, but are not limited thereto.

The weight ratio of the compound represented by Formula 2 and the mixed host compound is 95:5 to 5:95.

According to an exemplary embodiment of the present specification, the light emitting layer includes one or two or more compounds represented by Chemical Formula 2.

According to an exemplary embodiment of the present specification, the light emitting layer including the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 has a blue color.

An organic light emitting device according to an exemplary embodiment of the present specification includes two or more light emitting layers, and at least one of the two or more light emitting layers includes the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2. The light emitting layer containing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 is blue, and the light emitting layer not containing the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 is known in the art. It may contain a blue, red or green light emitting compound known to.

According to an exemplary embodiment of the present specification, the organic material 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 represented by Chemical Formula 1.

According to one embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer includes the heterocyclic compound represented by Chemical Formula 1.

According to one embodiment of the present specification, the organic material layer includes an electron blocking layer.

According to one embodiment of the present specification, the organic material layer includes a hole blocking layer.

According to an exemplary embodiment of the present specification, the organic light emitting device includes one layer or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. contains more

According to one embodiment of the present specification, the organic light emitting device may include a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

According to an exemplary embodiment of the present specification, the two or more organic material layers may be at least two selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and hole injection layer, and an electron blocking layer.

According to one embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.

According to one embodiment of the present specification, the first electrode is an anode or a cathode.

According to one embodiment of the present specification, the second electrode is a cathode or an anode.

According to one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 4 . 1 to 4 illustrate organic light emitting diodes, but are not limited thereto.

1 illustrates a structure of an organic light emitting device in which an anode 102, an emission layer 106, and a cathode 110 are sequentially stacked on a substrate 101. The heterocyclic compound represented by Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 2 may be further included in the light emitting layer.

2 illustrates a structure of an organic light emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. According to an exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 2 may be further included in the light emitting layer. According to another exemplary embodiment, the heterocyclic compound represented by Formula 1 is included in the hole injection layer or the hole transport layer.

3 shows an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, and an electron transport layer 108 on a substrate 101. , the structure of the organic light emitting device in which the electron injection layer 109 and the cathode 110 are sequentially stacked is illustrated. According to an exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 2 may be further included in the light emitting layer. According to another exemplary embodiment, the heterocyclic compound represented by Formula 1 is included in a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

4 shows an anode 102, a hole injection layer 103, a first hole transport layer 104-1, a second hole transport layer 104-2, a light emitting layer 106, an electron injection and transport layer ( 112) and the cathode 110 are sequentially stacked structure of the organic light emitting device is illustrated. According to an exemplary embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 2 may be further included in the light emitting layer.

The organic light emitting device of the present specification may be manufactured with materials and methods known in the art, except that the light emitting layer includes the compound, that is, the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2. there is.

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 a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, depositing a material that can be used as a cathode thereon. In addition to this 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.

In addition, the heterocyclic compound represented by Chemical Formula 1 or the compound represented by Chemical Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, 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, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic material layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The organic light emitting device according to the present specification may include an additional light emitting layer other than the light emitting layer including the heterocyclic compound represented by Chemical Formula 1 and/or the compound represented by Chemical Formula 2 above. The additional light emitting layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, aromatic amine derivatives include pyrene, anthracene, chrysene, and periplanthene having an arylamine group as condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is desirable. Also, a material having excellent thin film forming ability is preferred. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic substances; perylene-based organic materials; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; 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 according to the prior art. In particular, a suitable cathode material is a conventional material having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that receives electrons from an electrode. As the electron injecting material, it is preferable to have an excellent ability to transport electrons, an electron receiving effect from the second electrode, and an excellent electron injecting effect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and 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, etc. , but is not limited thereto.

The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks holes from reaching the light emitting layer, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.

An 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 depending on materials used.

Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in many different forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples detailed below. Examples and comparative examples in the present specification are provided to more completely explain the present specification to those skilled in the art.

<Production Example>

Preparation Example 1: Synthesis of Intermediate 1-1

1,4-dichloro-2,5-diisopropylbenzene (25g, 108.15 mmol) and Fe (1.21g, 21.6 mmol) were dissolved in chloroform (80 ml). Bromine (39.75 g, 248.75 mmol) was added dropwise slowly, and the mixture was stirred at room temperature. After the reaction was completed, bromine was quenched by adding Na ₂ S ₂ O ₃ . The reactants were transferred to a separatory funnel and then extracted. After drying with MgSO ₄ , filtering, concentrating, and purifying by column chromatography, intermediate 1-1 (37.02 g, yield 88%) was obtained.

MS:[M+H] ⁺ = 389

Preparation Example 2: Synthesis of Intermediate 1-2

1-chloro-4-methoxy-9H-carbazole (15 g, 64.74 mmol), bis(pinacolato)diboron (19.73 g, 77.69 mmol), Pd(OAc) ₂ (PCy ₃ ) ₂ (1.02 g, 1.3 mmol) , KOAc (19.06 g, 194.23 mmol) was dissolved in dioxane (220 ml) and stirred under reflux. After the reaction was completed, the mixture was cooled to room temperature, transferred to a separatory funnel, and then extracted. After drying with MgSO ₄ , filtering, concentrating, and purifying with column chromatography, intermediate 1-2 (15.69 g, yield 75%) was obtained.

MS:[M+H] ⁺ = 323

Preparation Example 3: Synthesis of Intermediate 1-3

Intermediate 1-1 (3.52g, 10 mmol), Intermediate 1-2 (6g, 18 mmol), Pd(PPh3)4 (0.35 g, 0.3 mmol), K ₂ CO ₃ (7.7 g, 55.7 mmol) was tetrahydro It was dissolved in furan (30 ml) and H ₂ O (10 ml) and stirred while refluxing. After the reaction was completed, the mixture was cooled to room temperature, transferred to a separatory funnel, and then extracted. After drying with MgSO ₄ , filtering, concentrating, and purifying with column chromatography, intermediate 1-3 (3.83 g, yield 68%) was obtained.

MS:[M+H] ⁺ =622

Preparation Example 4: Synthesis of intermediates 1-4

Intermediate 1-3 (12.6 g, 20.3 mmol), Pd(Pt-Bu ₃ ) ₂ (1.04 g, 2.0 mmol), and NaOt-Bu (3.9 g, 40.5 mmol) were dissolved in toluene (70 ml) and stirred under reflux. . After the reaction was completed, the mixture was cooled to room temperature, transferred to a separatory funnel, and then extracted. After drying with MgSO ₄ , filtering, concentrating, and purifying with column chromatography, intermediate 1-4 (6.56 g, yield 59%) was obtained.

MS:[M+H] ⁺ = 549

Preparation Example 5: Synthesis of intermediates 1-5

After dissolving Intermediate 1-4 (6.6 g, 12 mmol) in dichloromethane (40 ml), BBr ₃ (6.02 g, 24.1 mmol) was added and refluxed for 8 hours. When the reaction was completed, after cooling to room temperature, water was added, and the precipitate formed was filtered. The solid was washed with ethanol to obtain intermediate 1-5 (5.14 g, yield 82%).

MS:[M+H] ⁺ = 520

Preparation Example 6: Synthesis of intermediates 1-6

Intermediate 1-5 (5.14 g, 9.9 mmol) and K2CO3 (10.23 g, 74.0 mmol) were dissolved in dimethylformamide (DMF) (20 mL). After that, NfF (7.46 g, 24.7 mmol) was added. It was stirred for 2 hours at room temperature. When the reaction was completed, the reactant was transferred to a separatory funnel and then extracted. After drying with MgSO ₄ , filtering, concentrating, and purifying by column chromatography, intermediate 1-6 (9.32 g, yield 87%) was obtained.

MS:[M+H] ⁺ = 1084

Preparation Example 7: Synthesis of Compound 1

Intermediate 1-6 (12.6 g, 11.6 mmol), diphenylamine (4.03 g, 23.8 mmol), Pd(Pt-Bu ₃ ) ₂ (0.24 g, 0.5 mmol), NaOt-Bu (6.86 g, 71.4 mmol) It was dissolved in toluene (40 ml) and stirred while refluxing. When the reaction was completed, after cooling to room temperature, H ₂ O was added. The solid was filtered and washed with ethanol. Compound 1 (6.98 g, yield 73%) was obtained.

MS:[M+H] ⁺ = 823

Preparation Example 8: Synthesis of Compound 2

Compound 2 was obtained in the same manner as in Preparation Example 7 of Compound 1, except that bis(4-(tert-butyl)phenyl)amine was used instead of diphenylamine.

MS:[M+H] ⁺ = 823

Preparation Example 9: Synthesis of Compound 3

Compound 3 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 7, except that 2-fluoro-N-phenylaniline was used instead of diphenylamine.

MS:[M+H] ⁺ = 1155

Preparation Example 10: Synthesis of Compound 4

Compound 3 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 7, except that 2-fluoro-N-phenylaniline was used instead of diphenylamine.

MS:[M+H] ⁺ = 859

Preparation Example 11: Synthesis of Intermediate 5-1

1,4-dibromo-2,5-dichlorobenzene (52 g, 170.61 mmol) and AlCl ₃ (45.5 g, 341.2 mmol) were added, and 2-chloropropane-d ₇ (29.2 g, 341.2 mmol) was added slowly. it was added After raising the temperature from 0 ° C to room temperature, when the reaction was completed, it was lowered to 0 ° C and quenched with H ₂ O. After adding chloroform and stirring, the reactant was transferred to a separatory funnel and extracted. After drying with MgSO ₄ , filtering, concentrating, and purifying with column chromatography, intermediate 5-1 (62.95 g, yield 92%) was obtained.

MS:[M+H] ⁺ = 401

Preparation Example 12: Synthesis of Intermediate 5-2

5-2 was obtained in the same manner as in the preparation method of Intermediate 1-3 in Preparation Example 3, except that Intermediate 5-1 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 633

Preparation Example 13: Synthesis of Intermediate 5-3

Intermediate 5-3 was obtained in the same manner as in Preparation Example 4 of Intermediate 1-4, except that Intermediate 5-2 was used instead of Intermediate 1-3.

MS:[M+H] ⁺ = 560

Preparation Example 14: Synthesis of Intermediate 5-4

Intermediate 5-4 was obtained in the same manner as in the preparation method of Intermediate 1-5 in Preparation Example 5, except that Intermediate 5-3 was used instead of Intermediate 1-4.

MS:[M+H] ⁺ = 532

Preparation Example 15: Synthesis of Intermediate 5-5

Intermediate 5-5 was obtained in the same manner as in the preparation method of Intermediate 1-6 of Preparation Example 6, except that Intermediate 5-4 was used instead of Intermediate 1-5.

MS:[M+H] ⁺ = 1096

Preparation Example 16: Synthesis of Compound 5

Compound 5 was prepared in the same manner as in Preparation Example 7, except that Intermediate 5-5 was used instead of Intermediate 1-6 and 4-isopropyl-N-phenylaniline was used instead of diphenylamine. got

MS:[M+H] ⁺ = 921

Preparation Example 17: Synthesis of Compound 6

Compound 6 was prepared in the same manner as in Preparation Example 7 for preparing compound 1, except that Intermediate 5-5 was used instead of Intermediate 1-6 and 3-(phenylamino)benzonitrile was used instead of diphenylamine. got it

MS:[M+H] ⁺ = 887

Preparation Example 18: Synthesis of Intermediate 7-1

Except for using 1,4-dichloro-2,5-dimethylbenzene instead of 1,4-dichloro-2,5-diisopropylbenzene, the same method as in the preparation of intermediate 1-1 in Preparation Example 1 was used. Intermediate 7-1 was obtained.

MS:[M+H] ⁺ = 332

Preparation Example 18: Synthesis of Intermediate 7-2

Intermediate 7-2 was obtained in the same manner as in Preparation Example 3 of Intermediate 1-3, except that Intermediate 7-1 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 565

Preparation Example 19: Synthesis of Intermediate 7-3

Intermediate 7-3 was obtained in the same manner as in Preparation Example 4 of Intermediate 1-4, except that Intermediate 7-2 was used instead of Intermediate 1-3.

MS:[M+H] ⁺ = 492

Preparation Example 20: Synthesis of Intermediate 7-4

Intermediate 7-4 was obtained in the same manner as in the preparation method of Intermediate 1-5 in Preparation Example 5, except that Intermediate 7-3 was used instead of Intermediate 1-4.

MS:[M+H] ⁺ = 464

Preparation Example 21: Synthesis of Intermediate 7-5

Intermediate 7-5 was obtained in the same manner as in the preparation method of Intermediate 1-6 of Preparation Example 6, except that Intermediate 7-4 was used instead of Intermediate 1-5.

MS:[M+H] ⁺ = 1028

Preparation Example 22: Synthesis of Compound 7

Compound 1 of Preparation Example 7 except that Intermediate 7-5 was used instead of Intermediate 1-6 and 4-isopropyl-N-(4-(trimethylsilyl)phenyl)aniline was used instead of diphenylamine. Compound 7 was obtained in the same manner as in the preparation method.

MS:[M+H] ⁺ = 995

Preparation Example 23: Synthesis of Compound 8

Preparation of Compound 1 of Preparation Example 7, except that Intermediate 7-5 was used instead of Intermediate 1-6 and N-phenyldibenzo[b,d]thiophen-2-amine was used instead of diphenylamine. Compound 8 was obtained in the same manner as the method.

MS:[M+H] ⁺ = 995

Preparation Example 24: Synthesis of Intermediate 9-1

Intermediate 9-1 was obtained in the same manner as in Preparation Example 11 of Intermediate 5-1, except that chloromethane-d ₃ was used instead of 2-chloropropane-d ₇ .

MS:[M+H] ⁺ = 338

Preparation Example 25: Synthesis of Intermediate 9-2

Intermediate 9-2 was obtained in the same manner as in Preparation Example 3 of Intermediate 1-3, except that Intermediate 9-1 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 571

Preparation Example 26: Synthesis of Intermediate 9-3

Intermediate 9-3 was obtained in the same manner as in Preparation Example 4 of Intermediate 1-4, except that Intermediate 9-2 was used instead of Intermediate 1-3.

MS:[M+H] ⁺ = 498

Preparation Example 27: Synthesis of Intermediate 9-4

Intermediate 9-4 was obtained in the same manner as in the preparation method of Intermediate 1-5 in Preparation Example 5, except that Intermediate 9-3 was used instead of Intermediate 1-4.

MS:[M+H] ⁺ = 470

Preparation Example 28: Synthesis of Intermediate 9-5

Intermediate 9-5 was obtained in the same manner as in the preparation method of Intermediate 1-6 of Preparation Example 6, except that Intermediate 9-4 was used instead of Intermediate 1-5.

MS:[M+H] ⁺ = 1034

Preparation Example 29: Synthesis of Compound 9

The compound of Preparation Example 7 except that Intermediate 9-5 was used instead of Intermediate 1-6 and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine was used instead of diphenylamine. Compound 9 was obtained in the same manner as in Preparation 1.

MS:[M+H] ⁺ = 1005

Preparation Example 30: Synthesis of Compound 10

Intermediate 9-5 was used instead of Intermediate 1-6, and 6-cyclohexyl-N-phenyldibenzo[b,d]furan-4-amine was used instead of diphenylamine. Compound 10 was obtained in the same manner as in Compound 1.

MS:[M+H] ⁺ = 1117

Experimental Example 1-1

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. Detergent was a Fischer Co. product, and distilled water was a Millipore Co. product. Secondary filtered distilled water was used as the filter of the product. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvent, and dried.

A hole injection layer was formed by thermally vacuum depositing the compound HAT to a thickness of 50 Å on the prepared ITO transparent electrode. 1000 Å of the compound HT-A was vacuum-deposited thereon as a first hole transport layer, and 100 Å of the compound HT-B was subsequently deposited as a second hole transport layer. A light emitting layer having a thickness of 200 Å was formed by vacuum deposition of BH-1 as a host and Compound 1 as a dopant in a weight ratio of 98:2.

Then, as an electron injection and transport layer, 300 Å of the following compound ET-A and the following compound Liq were deposited in a 1: 1 ratio, on which 150 Å thick silver (Ag) 10% by weight doped magnesium (Mg) and 1,000 An organic light emitting device was manufactured by depositing Å-thick aluminum to form a cathode.

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

Experimental Examples 1-2 to 1-10

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following compounds 2 to 10 were used instead of the compound 1 as the dopant of the light emitting layer.

Comparative Example 1-1

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound D-1 was used instead of Compound 1 as the dopant of the light emitting layer.

Comparative Example 1-2

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound D-2 was used instead of Compound 1 as a dopant of the light emitting layer.

Experimental Examples 2-1 to 2-10

Organic light emitting devices were manufactured in the same manner as in Experimental Examples 1-1 to 1-10, except that the BH-2 was used instead of the BH-1 as the host of the light emitting layer.

Comparative Examples 2-1 and 2-2

In Comparative Examples 2-1 and 2-2, organic light emitting devices were manufactured in the same manner except that the BH-2 was used instead of the BH-1 as the host of the light emitting layer.

Experimental Examples 1-1 to 1-10, Comparative Examples 1-1 and 1-2 in Table 1, and Experimental Examples 2-1 to 2-10 and Comparative Examples 2-1 and 2- in Table 2 below. The measurement results of driving voltage, luminous efficiency, color coordinates and lifetime of the organic light emitting device of Fig. 2 are shown.

Specifically, the driving voltage, luminous efficiency, and color coordinates (CIEy) were measured at a current density of 10 mA/cm ² , and the time (LT95) to reach 95% of the initial luminance was measured at a current density of 20 mA/cm ² .

host dopant 10 mA/cm ² 20 mA/cm ² Driving voltage (V) Efficiency (cd/A) CIEy Lifetime (hr) Experimental Example 1-1 BH-1 compound 1 4.0 6.4 0.099 210 Experimental Example 1-2 BH-1 compound 2 4.1 6.3 0.098 210 Experimental Example 1-3 BH-1 compound 3 4.2 6.2 0.099 214 Experimental Example 1-4 BH-1 compound 4 4.3 6.0 0.098 216 Experimental Example 1-5 BH-1 compound 5 4.1 6.6 0.099 209 Experimental Example 1-6 BH-1 compound 6 4.2 6.3 0.097 219 Experimental Example 1-7 BH-1 compound 7 3.9 6.5 0.098 211 Experimental Example 1-8 BH-1 compound 8 4.3 6.6 0.098 206 Experimental Example 1-9 BH-1 compound 9 3.9 6.3 0.097 216 Experimental Example 1-10 BH-1 compound 10 4.4 6.4 0.100 208 Comparative Example 1-1 BH-1 D-1 4.4 5.1 0.098 172 Comparative Example 1-2 BH-1 D-2 4.3 5.4 0.096 170

host dopant 10 mA/cm ² 20 mA/cm ² Driving voltage (V) Efficiency (cd/A) CIEy Lifetime (hr) Experimental example 2-1 BH-2 compound 1 4.1 6.6 0.098 215 Experimental Example 2-2 BH-2 compound 2 4.1 6.5 0.099 217 Experimental example 2-3 BH-2 compound 3 4.0 6.4 0.098 225 Experimental example 2-4 BH-2 compound 4 4.2 6.2 0.098 236 Experimental example 2-5 BH-2 compound 5 4.3 6.8 0.097 222 Experimental example 2-6 BH-2 compound 6 4.3 6.5 0.098 219 Experimental example 2-7 BH-2 compound 7 4.1 6.6 0.099 226 Experimental example 2-8 BH-2 compound 8 4.1 6.7 0.097 231 Experimental example 2-9 BH-2 compound 9 3.7 6.5 0.097 235 Experimental Example 2-10 BH-2 compound 10 4.3 6.3 0.100 227 Comparative Example 2-1 BH-2 D-1 4.3 5.4 0.099 192 Comparative Example 2-2 BH-2 D-2 4.2 5.6 0.098 189

From Tables 1 and 2, the organic light emitting devices of Experimental Examples 1-1 to 1-10 and 2-1 to 2-10 are Comparative Examples 1-1 and 1-2 in which R1 and R2 of Formula 1 are hydrogen or a phenyl group; It was confirmed that the efficiency and lifetime were superior to those of the organic light emitting devices 2-1 and 2-2. Specifically, the heterocyclic compound of Formula 1 of the present specification is structurally stable, and the stability of the compound due to heat increases due to the substituent. Therefore, when applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage and long lifespan characteristics can be obtained.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and implementations are possible within the scope of the claims and the detailed description of the invention, and this also belongs to the scope of the invention. .

101: substrate
102 anode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: light emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: cathode
104-1: first hole transport layer
104-2: second hole transport layer
112: electron injection and transport layer

Claims (13)

A heterocyclic compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
R1 and R2 are the same as or different from each other, and are each independently a straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium,
L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R3 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r3 is an integer from 1 to 4, and when r3 is 2 or more, two or more R3s are the same as or different from each other;
r4 is an integer from 1 to 3, and when r4 is 2 or more, two or more R4s are the same as or different from each other;
2 ≤ r3+ r4 ≤ 6;
r5 is an integer from 1 to 3, and when r5 is 2 or more, two or more R5s are the same as or different from each other;
r6 is an integer from 1 to 4, and when r6 is 2 or more, two or more R6s are the same as or different from each other;
2 ≤ r5 + r6 ≤ 6. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1:
[Formula 1-1]

In Formula 1-1,
The definitions of R1, R2, L1, L2 and Ar1 to Ar4 are the same as defined in Formula 1 above. delete The heterocyclic compound according to claim 1, wherein L1 and L2 are direct bonds. The method according to claim 1, wherein Ar1 to Ar4 are the same as or different from each other, and each independently represents a deuterium, a halogen group, a cyano group, a straight or branched chain alkyl group having 1 to 30 carbon atoms, or a straight chain or branched chain alkyl group having 1 to 30 carbon atoms. A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a silyl group, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms ; Or a straight chain or branched chain alkyl group having 1 to 30 carbon atoms, a linear or branched chain alkylsilyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and a linear or branched chain alkyl group having 1 to 30 carbon atoms. A heterocyclic compound which is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted with . The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is 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 more organic material layers provided between the first electrode and the second electrode,
An organic light emitting device in which at least one layer of the organic material layer includes the heterocyclic compound according to any one of claims 1, 2, and 4 to 6. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, the light emitting layer includes a dopant material, and the dopant material is the heterocyclic compound. The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound and a compound represented by Formula 2 below:
[Formula 2]

In Formula 2,
L21 to L23 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
l21 is an integer from 1 to 3, and when l21 is 2 or more, two or more L21s are the same as or different from each other;
l22 is an integer from 1 to 3, and when l22 is 2 or more, two or more L22s are the same as or different from each other;
l23 is an integer from 1 to 3, and when l23 is 2 or more, two or more L23s are the same as or different from each other,
a is 0 or 1; The organic light emitting device of claim 7 , wherein the organic material 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. The organic light emitting device of claim 7, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the heterocyclic compound. The method according to claim 7, wherein the organic material layer further comprises one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. light emitting element.