KR20200032658A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of formula 1, and an organic light emitting device including the same. The heterocyclic compound according to an embodiment of the present specification may be used as an ingredient of an organic material layer of the organic light emitting device.

Description

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

The present invention claims the benefit of the filing date of Korean Patent No. 10-2018-0111495, filed with the Korean Patent Office on September 18, 2018, all of which is incorporated herein.

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 that converts 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 and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for such organic light-emitting devices continues to be required.

US Patent Application Publication No. 2004-0251816

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

One embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

Y1 and Y2 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted hetero ring, a substituted or unsubstituted aliphatic ring, or a ring in which two or more of them are condensed,

X is a direct bond or O,

Ar ₁ to Ar ₄ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted arylamine group, or adjacent substituents are connected to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Form,

a is an integer from 1 to 3, and when a is plural, R 1 is the same as or different from each other,

b is an integer of 1 to 8, and when b is plural, R2 is the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided opposite to the first electrode; And an organic material layer provided between one or two or more layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the heterocyclic compound. .

The heterocyclic compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using this, high light emission efficiency and / or high color purity can be obtained in an organic light emitting device.

1 shows an organic light emitting diode according to an exemplary embodiment of the present specification.
2 shows an organic light emitting diode according to an exemplary embodiment of the present specification.

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

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

The heterocyclic compound represented by Formula 1 in the present specification is characterized in that a ring is formed by connecting Y1 and Y2. If Y1 and Y2 are not connected, the ortho-position hydrogens of boron located in Y1 and Y2 cause the structure to be distorted due to the repulsive force between each other. By bundling this part to form a ring, the vibrational energy of the material can be reduced, and the emission of this material mostly occurs at the 0-0 transition, so that the spectrum has a narrower half width. Accordingly, when the heterocyclic compound represented by Chemical Formula 1 is applied to an organic electroluminescent device, a device having high efficiency and high color purity can be obtained.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

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

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

The term "substitution" means that the hydrogen atom bonded to the 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 the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to deuterium; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, the "substituent in which two or more substituents are connected" 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 straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specific examples include methyl groups; Ethyl group; Propyl group; n-propyl group; Isopropyl group; Butyl group; n-butyl group; Isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethyl butyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; Heptyl group; n-heptyl group; 1-methylhexyl group; Cyclopentyl methyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; Isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; Cyclobutyl group; Cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; Cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl group; Cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specifically, a methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; p-methylbenzyloxy group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluorenylamine group and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula —SiRiRjRk, wherein Ri, Rj and Rk are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. 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. More specifically, it is preferable that it has 6 to 20 carbon atoms. Specifically, as the monocyclic aryl group, a phenyl group; Biphenyl group; It may be a terphenyl group, 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 preferably 10 to 30 carbon atoms, and more preferably 10 to 20 carbon atoms. Specifically, a polycyclic aryl group is a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. You can. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline 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 containing 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 simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, X, R ₁ and R ₂ , Ar ₁ to Ar ₄ , a, and b are as defined in Formula 1,

X ₁ to X ₄ are the same as or different from each other, and each independently, a direct bond, O, S or CRaRb,

X ₁ and X ₂ are not a direct bond at the same time, and X ₃ and X ₄ are not a direct bond at the same time,

Ra and Rb are hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, or substituted or unsubstituted aryl It is an amine group.

In one embodiment of the present specification, X is a direct bond or O.

In one embodiment of the present specification, X is a direct bond.

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

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic ring.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently an aromatic ring.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a substituted or unsubstituted heteroring.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently a heterocycle.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently an substituted or unsubstituted aliphatic ring.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently an aliphatic ring.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently an aromatic ring and a heterocycle are fused rings.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and are each independently benzene, naphthalene, dibenzofuran, dibenzothiophene, or fluorene unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted hetero atom having 3 to 30 carbon atoms. It is an aryl group.

In one embodiment of the present specification, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms, or the heteroaryl group having 3 to 30 carbon atoms, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or It is substituted or unsubstituted with one or more substituents selected from the group consisting of substituted or unsubstituted heteroaryl groups.

In one embodiment of the present specification, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms, or the heteroaryl group having 3 to 30 carbon atoms is deuterium; Halogen group; Nitrile group; An alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing any one or more of N, O, and S having 3 to 30 carbon atoms.

In one embodiment of the present specification, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms,

The aryl group having 6 to 30 carbon atoms, or the heteroaryl group having 3 to 30 carbon atoms is deuterium; Halogen group; Nitrile group; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Terbutyl group; Pentyl group; Hexyl group; A silyl group substituted with a methyl group or a phenyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Anthracene group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Triphenylene group; Carbazole; Dibenzofuran group; Dibenzothiophene group; Pyridine group; Pyrimidine group; And one or more substituents selected from the group consisting of triazine groups.

In one embodiment of the present specification, Ar ₁ to Ar ₄ are the same or different from each other, and each independently a methyl group, a terbutyl group, or a phenyl group unsubstituted or substituted with a trimethylsilyl group.

In one embodiment of the present specification, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently a phenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with a terbutyl group, or a phenyl group substituted with a trimethylsilyl group.

In one embodiment of the present specification, R ₂ is hydrogen.

In one embodiment of the present specification, R ₁ is hydrogen.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R ₁ is an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R ₁ is an amine group substituted with an aryl group.

In one embodiment of the present specification, R ₁ is an amine group substituted with an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R ₁ is an amine group substituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthracene group, phenanthrene group, triphenylene group, fluorene group, or pyrene group.

In one embodiment of the present specification, R ₁ is an amine group substituted with a phenyl group.

In one embodiment of the present specification, X ₁ to X ₄ are the same as or different from each other, and each independently a direct bond, O, S, or CRaRb.

In one embodiment of the present specification, X ₁ and X ₃ are a direct bond.

In one embodiment of the present specification, X ₂ and X ₄ are a direct bond.

In one embodiment of the present specification, X ₂ and X ₃ are a direct bond.

In one embodiment of the present specification, X ₁ and X ₄ are a direct bond.

In one embodiment of the present specification, X ₁ and X ₃ are O.

In one embodiment of the present specification, X ₂ and X ₄ are O.

In one embodiment of the present specification, X ₂ and X ₃ are O.

In one embodiment of the present specification, X ₁ and X ₄ are O.

In one embodiment of the present specification, X ₁ and X ₃ are CRaRb.

In one embodiment of the present specification, X ₂ and X ₄ are CRaRb.

In one embodiment of the present specification, X ₂ and X ₃ are CRaRb.

In one embodiment of the present specification, X ₁ and X ₄ are CRaRb.

In one embodiment of the present specification, X ₁ and X ₃ are a direct bond, and X ₂ and X ₄ are O.

In one embodiment of the present specification, X ₁ and X ₃ are a direct bond, and X ₂ and X ₄ are CRaRb.

In one embodiment of the present specification, X ₂ and X ₄ are a direct bond, and X ₁ and X ₃ are O.

In one embodiment of the present specification, X ₂ and X ₄ are a direct bond, and X ₁ and X ₃ are CRaRb.

In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkyl silyl groups; Aryl group; Heteroaryl group; Or an arylamine group.

In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; F; Cl; Br; I; An alkyl group having 1 to 10 carbon atoms; An alkylsilyl group having 1 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms; A heteroaryl group having 3 to 30 carbon atoms; Or an arylamine group having 12 to 60 carbon atoms.

In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; F; Cl; Br; I; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Terbutyl group; A silyl group substituted with a methyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Triazine group; Or an amine group substituted with a phenyl group, biphenyl group, naphthyl group, or terphenyl group.

In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms; A heteroaryl group having 3 to 30 carbon atoms; Or an arylamine group having 12 to 60 carbon atoms.

In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Or a terbutyl group.

In one embodiment of the present specification, Ra and Rb are methyl groups.

In one embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

The organic light emitting device of the present invention comprises a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer may include the aforementioned heterocyclic compound.

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

In FIG. 1, a structure of an organic light emitting device in which the first electrode 2, the organic material layer 3, and the second electrode 4 are sequentially stacked on the substrate 1 is illustrated. The compound of Formula 1 is included in the organic material layer (3).

In FIG. 2, the first electrode 2 on the substrate 1, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the electron transport layer 9, the electron injection layer ( 10) and the structure of the organic light emitting device in which the second electrodes 4 are sequentially stacked is illustrated. The compound of Formula 1 may be included in the hole transport layer 6, the light emitting layer 8, or the electron transport layer 9. Preferably it can be included in the light emitting layer.

2 illustrates an organic light emitting device, and is not limited thereto. Between the hole injection layer 5 and the hole transport layer 6, between the electron blocking layer 7 and the light emitting layer 8, the light emitting layer 8 and electrons An additional organic material layer may be further included between the transport layer 9 and between the electron transport layer 9 and the electron injection layer 10.

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

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound of Formula 1 above.

In one embodiment of the present invention, the light emitting layer may include a plurality of hosts and a plurality of dopants.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 99: 1 to 70:30.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 99: 1 to 80:20.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 99: 1 to 90:10.

In one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Chemical Formula 1 as a dopant.

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

In an exemplary embodiment of the present invention, the light emitting layer includes an aromatic compound as a host.

In one embodiment of the present invention, the light-emitting layer includes an anthracene-based compound as a host.

In one embodiment of the present invention, the light emitting layer includes a compound represented by the following formula (A) as a host.

[Formula A]

In Chemical Formula A,

XX ₁ and XX ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

XX ₃ is hydrogen, deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, substituted or unsubstituted Heteroaryl group, or substituted or unsubstituted arylamine group,

c is an integer from 0 to 8, and when c is 2 or more, XX3 is the same or different from each other.

In one embodiment of the present invention, XX ₁ and XX ₂ are the same as or different from each other, and each independently an substituted or unsubstituted aryl group.

In one embodiment of the present invention, XX1 and XX2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present invention, XX ₁ and XX ₂ are the same or different from each other, and each independently an aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted with an aryl group.

In one embodiment of the present invention, XX ₁ and XX ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted It is a substituted anthracene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted pyrene group.

In one embodiment of the present invention, XX ₁ and XX ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, XX ₁ and XX ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present invention, XX ₁ and XX ₂ are the same as or different from each other, and each independently a biphenyl group or a naphthyl group.

In one embodiment of the present invention, XX ₃ is hydrogen.

In an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer comprises the heterocyclic compound of Formula 1 It can contain.

In an exemplary embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer comprises the heterocyclic compound of Formula 1 It can contain.

In one embodiment of the present invention, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by Chemical Formula 1.

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

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

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, to have a metal or conductive metal oxide on the substrate or alloys thereof To form an anode, and then form a hole injection layer, a hole transport layer, an organic layer including a light emitting layer, an electron transport layer, and an organic material layer including a heterocyclic compound of Formula 1, and then a material that can be used as a cathode It can be prepared by depositing. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The positive electrode material is usually a material having a large work function 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), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF / Al or LiO2 / Al, but is not limited thereto.

As the hole injection material, a hole injection material can be well injected from the anode at a low voltage, and it is preferable that the hole injection material has a high occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic compounds, anthraquinones, and polyaniline-based conductive polymers of a poly compound, and the like, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable as a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

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.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using the heterocyclic compound.

The present specification also provides a method for manufacturing an organic light emitting device formed using the heterocyclic compound.

Examples of the dopant material include aromatic heterocyclic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic heterocyclic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. As a compound in which at least one arylvinyl group is substituted in the substituted arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

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

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the 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 and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that prevents the cathode from reaching the cathode, 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 complex, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

The following Synthesis Examples and Examples are intended to aid the understanding of those skilled in the art and are not limited thereto. The following synthetic examples are for representative compounds of the present invention, but different starting materials and intermediate materials can be used to obtain compounds having various substituents and substitution positions. Through this, it is possible to prepare all compounds of the present invention.

[ Synthetic example ]

Synthetic example  1: Synthesis of Intermediate A

Step 1) Synthesis of Intermediate A-1

After dissolving 3,5-dibromophenol (20.0g, 79.4mmol) in 300 mL of tetrahydrofuran (THF) under nitrogen condition, add n-butyllithium 2.5M in hexane (47.6ml, 119.1mmol), and at -78 ℃. After stirring for 1 hour, ethyl 3-bromo-5-hydroxybenzoate (21.4 g, 87.3 mmol) was added together with a small amount of solvent. After raising to room temperature after 10 hours, NH ₄ Cl aqueous solution was added, and the reaction solution was transferred to a separatory funnel and extracted with ethyl acetate. The extract was dried over MgSO ₄ , concentrated, and the sample was purified by silica gel column chromatography to obtain 15.7 g of Intermediate A-1. (Yield 53%, MS [M + H] + = 372)

Step 2) Synthesis of Intermediate A

Under nitrogen condition, intermediate A-1 (20.0 g, 53.8 mmol) was dissolved in 160 ml of THF and 160 ml of DMF, and the temperature was lowered to -40 ° C. Then, 2-chloroethan-1-ol (5.4 ml, 80.6 mmol) was added thereto, and 1.0M in THF (80.6 ml, 80.6 mmol) of potassium terbutoxide was slowly added dropwise. After 2 hours, the mixture was raised to room temperature, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , concentrated, and the sample was purified by silica gel column chromatography to obtain 20.8 g of Intermediate A. (Yield 93%, MS [M + H] + = 368)

Synthetic example  2: Synthesis of Intermediate B

Step 1) Synthesis of Intermediate B-1

Bis (3-bromo-4,5-dihydroxyphenyl) methanone (20.0g, 49.5mmol), (4-chloro-2-fluorophenyl) boronic acid (9.1g, 52.0mmol) in 400 ml of THF Dissolve and dissolve potassium carbonate (27.4g, 198.0mmol) in 200ml of water. Tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.5mmol) was added thereto, and the mixture was stirred for 8 hours under argon atmosphere reflux conditions. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with ethyl acetate. The extract was dried over MgSO ₄ , concentrated, and the sample was purified by silica gel column chromatography to obtain 18.7 g of intermediate B-1. (Yield 75%, MS [M + H] + = 503)

Step 2) Synthesis of Intermediate B-2

300 ml of N-methyl-2-pyrrolidone (NMP) was added to intermediate B-1 (20.0 g, 39.7 mmol) and potassium carbonate (12.6 g, 91.4 mmol) and stirred at 120 ° C overnight. After the reaction was completed, after cooling to room temperature, 200 ml of water was gradually added dropwise to the reaction solution. Thereafter, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain 15.8 g of intermediate B-2. (Yield 86%, MS [M + H] + = 463)

Step 3) Synthesis of Intermediate B

Under nitrogen condition, intermediate B-2 (20.0 g, 43.2 mmol) was dissolved in 160 ml of THF and 160 ml of DMF, and the temperature was lowered to -40 ° C. Then, 2-chloroethan-1-ol (4.3 ml, 64.8 mmol) was added thereto, and 1.0M in THF (64.8 ml, 64.8 mmol) of potassium terbutoxide was slowly added dropwise thereto. After 2 hours, the mixture was raised to room temperature, and extracted with water and ethyl acetate. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to obtain 20.4 g of intermediate B. (Yield 93%, MS [M + H] + = 507)

Synthetic example  3: Synthesis of Compound 1

Step 1) Synthesis of Compound 1-1

Intermediate A (20.0g, 48.1mmol), bis (4- (terbutyl) phenyl) amine (28.4g, 100.9mmol) was dissolved in 450ml of toluene and sodium terbutoxide (9.2g, 96.1mol), bis (tri-ter After adding butylphosphine) palladium (0) (1.0g, 1.9mmol), the mixture was stirred under argon atmosphere reflux for 6 hours. After the reaction was completed, after cooling to room temperature, water was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried over MgSO ₄ , concentrated, and the sample was purified by silica gel column chromatography to obtain 16.9 g of Compound 1-1. (Yield 43%, MS [M + H] + = 817)

Step 2) Synthesis of Compound 1-2

Compound 1-1 (20.0 g, 24.5 mmol), 2-bromo-1,3-difluorobenzene (5.2 g, 26.9 mmol) and potassium carbonate (4.1 g, 29.4 mmol) were added with 300 ml of NMP at 120 ° C. Stir overnight. After the reaction was completed, after cooling to room temperature, 200 ml of water was gradually added dropwise to the reaction solution. Thereafter, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain 20.4 g of Compound 1-2. (Yield 86%, MS [M + H] + = 970)

Step 3) Synthesis of Compound 1-3

Compound 1-2 (20.0 g, 20.6 mmol) was dissolved in 350 ml of THF, and then 80 ml of 6N HCl was slowly added. After 7 hours under reflux, the reaction was cooled to room temperature. The resulting solid was filtered, washed excessively with water and hexane, and dried through nitrogen to obtain 17.4 g of Compound 1-3. (Yield 91%, MS [M + H] + = 926)

Step 4) Synthesis of Compound 1-4

After dissolving compound 1-3 (20.0g, 21.6mmol) in 300 mL of THF under nitrogen condition, add n-butyllithium 2.5M in hexane (13.0ml, 32.4mmol) and stir at -78 ℃ for 1 hour, and then 2-bromo -1,1'-biphenyl (5.5g, 23.8mmol) was added with a small amount of solvent. After raising to room temperature after 10 hours, NH ₄ Cl aqueous solution was added, and the reaction solution was transferred to a separatory funnel and extracted with ethyl acetate. The extract was dried over MgSO ₄ , concentrated, and the sample was purified by silica gel column chromatography to obtain 12.4 g of Compound 1-4. (Yield 53%, MS [M + H] + = 1080)

Step 5) Synthesis of Compound 1-5

Compound 1-4 (20.0 g, 18.5 mmol) was added to 240 ml of acetic acid and 0.4 ml of concentrated sulfuric acid was slowly added dropwise while stirring. After raising the temperature and reacting at 50 ° C. for 4 hours, 120 ml of water was added to filter the resulting solid rule. After further washing with water and hexane, nitrogen drying was performed to obtain 17.2 g of Compound 1-5. (Yield 86%, MS [M + H] + = 1082)

Step 6) Synthesis of Compound 1

Compound 1-5 (20.0 g, 18.5 mmol) was dissolved in 400 ml of terbutylbenzene and cooled to 0 ° C. Under nitrogen atmosphere, 1.7 M of terbutyl lithium in pentane (16.3 ml, 27.7 mmol) was added and stirred at 60 ° C. for 2 hours. After that, the reaction was cooled to 0 ° C again, boron tribromide (2.7ml, 27.7mmol) was added, and the mixture was stirred at room temperature for 0.5 hour. The reaction was again cooled to 0 ° C, N, N-diisopropylethylamine (4.8ml, 27.7mmol) was added, followed by stirring at 60 ° C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and extracted with a separatory funnel using ethyl acetate and water. The extract was dried, concentrated with MgSO ₄ and the sample was purified by silica gel column chromatography, and 2.0 g of Compound 1 was obtained through a sublimation tablet. (Yield 11%, MS [M + H] + = 991)

Synthesis Example 4: Synthesis of Compound 2

In Synthesis Example 3, the compound was synthesized in the same production method as in Compound 1, except that bis (4- (terbutyl) phenyl) amine was changed to N-phenyl-4- (trimethylsilyl) aniline and used. 2 was obtained. (MS [M + H] ⁺ = 911)

Synthesis Example 5: Synthesis of Compound 3

In Synthesis Example 3, Compound 3 was obtained by synthesizing in the same production method as in Compound 1, except that Intermediate A was changed to Intermediate B and used. (MS [M + H] ⁺ = 1171)

[ Example ]

Example  One

ITO (Indium Tin Oxide) was coated with a thin film coated with a thickness of 1,400Å in distilled water dissolved in detergent and washed with ultrasonic waves. At this time, Decon ™ CON705 manufactured by Fisher Co. was used as a detergent, and distilled water filtered second by a 0.22 μm sterilizing filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed for 10 minutes each with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, the following HI-A and LG-101 were sequentially thermal vacuum deposited to a thickness of 650 Pa and 50 Pa, respectively, to form a hole injection layer. The following HT-A was vacuum-deposited to a thickness of 600 MPa as a hole transport layer, and the following HT-B was thermally vacuum-deposited to a thickness of 50 MPa as an electron blocking layer. Subsequently, BH-A and Compound 1 were vacuum-deposited to a thickness of 200 Pa in a weight ratio of 96: 4 as a light emitting layer. Subsequently, a compound represented by ET and Liq as an electron transport layer was thermally vacuum-deposited to a thickness of 360 Pa at a weight ratio of 1: 1, and then a compound represented by Liq was vacuum-deposited to a thickness of 5 Pa to form an electron injection layer. On the electron injection layer, magnesium and silver were sequentially deposited at a weight ratio of 10: 1 to a thickness of 220 Å and aluminum to a thickness of 1000 형성 to form a cathode, thereby producing an organic light emitting device.

Example  2, Example  3, Comparative example  1 and Comparative example  2

The organic light emitting device of Example 2, Example 3, Comparative Example 1 and Comparative Example 2 was used in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead as dopant materials in Example 1. Each was produced.

By applying a current to the organic light-emitting device prepared in Examples 1 to 3 and Comparative Examples 1 to 2, voltage, efficiency, and lifetime (T95) were measured and the results are shown in Table 1 below.

Here, the voltage and efficiency were measured by applying a current density of 10mA / cm ² , and the FWHM (half width) was obtained from the spectrum measured at this time. T95 means the time from the initial density of 20 mA / cm ² until the initial luminance decreases to 95%.

Dopant @ 10mA / cm ² @ 20mA / cm ² V QE FWHM (nm) LT95 Example 1 Compound 1 3.73 7.71 35 125 Example 2 Compound 2 3.71 7.76 38 120 Example 3 Compound 3 3.65 7.82 37 127 Comparative Example 1 BD-A 3.70 7.68 47 81 Comparative Example 2 BD-B 3.99 7.43 54 120

The boron compound such as BD-A applied to Comparative Example 1 has a narrow half width compared to a dopant such as BD-B, and thus has an advantage of obtaining high color purity when applied to an organic electroluminescent device. On the other hand, BD-A has a disadvantage in that the life of the device is lower than that of BD-B due to the unstable structure in which the structure is distorted due to the repulsive force by two hydrogen atoms at the ortho position of boron.

In the compound of Formula 1 of the present invention, instead of hydrogen atoms coming to the substituents at the carbon atoms at the ortho position of boron, they are connected to each other to form a ring, thereby reducing the repulsive force to increase the stability of the material. In addition, the vibration energy is reduced due to the formed ring, and the emission spectrum is also narrowed.

Therefore, when applied as a dopant of an organic light emitting device, it exhibits a high lifespan while maintaining the characteristics of a narrow half width.

1: Substrate
2: first electrode
3: organic layer
4: Second electrode
5: hole injection layer
6: hole transport layer
7: Electronic blocking layer
8: emitting layer
9: electron transport layer
10: electron injection layer

Claims (8)

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

In Chemical Formula 1,
Y1 and Y2 are the same as or different from each other, and each independently, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted hetero ring, a substituted or unsubstituted aliphatic ring, or a ring in which two or more of them are condensed,
X is a direct bond or O,
Ar ₁ to Ar ₄ are the same as or different from each other, and each independently, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group , A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted arylamine group, or a substituted or unsubstituted hydrocarbon ring connected by adjacent substituents, or a substituted or unsubstituted heteroring To form,
a is an integer from 1 to 3, and when a is plural, R 1 is the same as or different from each other,
b is an integer of 1 to 8, and when b is plural, R2 is the same as or different from each other. In claim 1, wherein Formula 1 is a heterocyclic compound represented by any one of the following Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, X, R ₁ and R ₂ , Ar ₁ to Ar ₄ , a, and b are as defined in Formula 1,
X ₁ to X ₄ are the same as or different from each other, and each independently, a direct bond, O, S or CRaRb,
X ₁ and X ₂ are not direct bonds at the same time, X ₃ and X ₄ are not direct bonds at the same time,
Ra and Rb are hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, or substituted or unsubstituted aryl It is an amine group. In claim 1, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. Heterocyclic compound. In claim 1, wherein X is a heterocyclic compound that is a direct bond. The method according to claim 1, wherein Formula 1 is a heterocyclic compound that is any one selected from the following compounds:

A first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the heterocyclic compound of claim 1. Phosphorus organic light emitting device. The method according to claim 6, The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising a host and a dopant in a mass ratio of 99: 1 to 80:20. The method according to claim 6, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising the heterocyclic compound as a dopant.

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