KR102214594B1 - 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.

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0116942 filed with the Korean Intellectual Property Office on October 1, 2018, the entire contents of which are incorporated herein.

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it 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. In the structure of such an 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 excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

US Patent Application Publication No. 2004-0251816

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

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

[Formula 1]

In Formula 1,

X ₁ to X ₃ are the same as or different from each other, and each independently CH or N,

2 or more of X ₁ to X ₃ are N,

Y is O or S,

R is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

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

L ₁ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar ₁ and Ar 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,

n is an integer of 0 to 8, and when n is plural, R is the same as or different from each other.

In addition, an exemplary embodiment of the present specification, the 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 of the organic material layers includes the heterocyclic compound.

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

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

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

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

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; 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 heteroaryl group substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, the "substituent to 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 heteroaryl group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

In the present specification, the halogen group includes a fluorine group, a bromo group, a chloro group, and an iodo group.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. Specific examples include methyl group; 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-ethylbutyl 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; Cyclopentylmethyl 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 are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but it 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 are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 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; It may be a p-methylbenzyloxy group and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; N-phenylnaphthylamine 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-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but are not limited thereto.

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

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

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

In the present specification, the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc 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; Vinyldimethylsilyl group; Propyldimethylsilyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but are 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 it is preferably 6 to 30 carbon atoms. More specifically, it is preferably 6 to 20 carbon atoms. Specifically, the monocyclic aryl group is a phenyl group; Biphenyl group; It may be a terphenyl group or 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 preferred that it has 10 to 30 carbon atoms, and more specifically, it is preferred that it has 10 to 20 carbon atoms. Specifically, the polycyclic aryl group includes a naphthyl group; Anthracene group; Phenanthrene group; Triphenylene group; Pyren group; Phenalene group; Perylene group; Cryen group; It may be a fluorene group, but is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an 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, or a substituted or unsubstituted diarylamine 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 may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms and heteroatoms other than carbon, and specifically, the heteroatom 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, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a 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, an acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazin group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group (phenanthridine), phenanthroline group (phenanthroline), isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxathiine group, phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorenxanthene group and spirofluorene Thioxanthene groups, and the like, but are not limited thereto.

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 the examples of the heteroaryl group described above.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.

[Formula 2]

[Formula 3]

In Formulas 2 and 3, R, Z, X ₁ to X ₃ , Ar ₁ , Ar _2, L ₁ and n are as defined in Formula 1.

In the exemplary embodiment of the present specification, X ₁ to X ₃ are N.

In the exemplary embodiment of the present specification, X ₁ and X ₃ are N, and X ₂ is CH.

In the exemplary embodiment of the present specification, X ₁ and X ₂ are N, and X ₃ is CH.

In the exemplary embodiment of the present specification, X ₂ and X ₃ are N, and X ₁ is CH.

In the exemplary embodiment of the present specification, Y is O.

In the exemplary embodiment of the present specification, Y is S.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification; R is hydrogen; heavy hydrogen; Nitrile group; Halogen group; Alkyl group; Alkoxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group unsubstituted or substituted with an alkyl group; Or an alkyl group or a heteroaryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R is hydrogen.

In the exemplary embodiment of the present specification, Ar ₁ and Ar 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 containing 1 to 3 heteroatoms selected from the group consisting of N, O, and S.

In the exemplary embodiment of the present specification, Ar ₁ and Ar ₂ 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 containing 1 to 3 heteroatoms selected from the group consisting of N, O and S.

In the exemplary embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Pyren group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Triazine group; Benzocarbazole group; Quinazoline; Quinoline group; Or benzimidazole,

The phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Pyren group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Triazine group; Benzocarbazole group; Quinazoline; Quinoline group; Or the benzimidazole group is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Pyren group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Triazine group; Benzocarbazole group; Quinazoline; Quinoline group; Or benzimidazole,

The phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Pyren group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Triazine group; Benzocarbazole group; Quinazoline; Quinoline group; Or the benzimidazole group is a methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; And it is unsubstituted or substituted with one or more substituents selected from a carbazole group.

In the exemplary embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A dibenzofuran group unsubstituted or substituted with an aryl group; A dibenzothiophene group unsubstituted or substituted with an aryl group; Or a carbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A dibenzofuran group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A dibenzothiophene group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a carbazole group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, L ₁ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In the exemplary embodiment of the present specification, L ₁ is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroarylene group.

In the exemplary embodiment of the present specification, L ₁ is a direct bond, a phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent naphthyl group; Divalent anthracene group; Divalent phenanthrene group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Divalent carbazole group; A divalent pyridine group; Divalent pyrimidine group; Or a divalent triazine group.

In the exemplary embodiment of the present specification, L ₁ is a direct bond.

In the exemplary embodiment of the present specification, L ₁ is a phenylene group.

In the exemplary embodiment of the present specification, Z is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 3 to C 30 heteroaryl group.

In the exemplary embodiment of the present specification, Z is 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 including any one or more heteroatoms of N, O, or S.

In the exemplary embodiment of the present specification, Z is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted fluorene group.

In the exemplary embodiment of the present specification; Z is a phenyl group; Biphenyl group; Terphenyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Or a triazine group,

The phenyl group; Biphenyl group; Terphenyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Or the triazine group is substituted or unsubstituted with a C1-C10 alkyl group, a C6-C30 aryl group, or a C3-C30 heteroaryl group.

In the exemplary embodiment of the present specification, Z is a phenyl group; Biphenyl group; Terphenyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Or a triazine group,

The phenyl group; Biphenyl group; Terphenyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Pyridine group; Pyrimidine group; Or the triazine group is methyl group, ethyl group, propyl group, isopropyl group, terbutyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracene group, phenanthrene group, dibenzofuran group, dibenzothiophene group , A carbazole group, a pyridine group, a pyrimidine group, and a triazine group substituted or unsubstituted with any one or more.

In the exemplary embodiment of the present specification, Z is a phenyl group or a phenyl group unsubstituted or substituted with a methyl group; A biphenyl group unsubstituted or substituted with a phenyl group or a methyl group; A terphenyl group unsubstituted or substituted with a phenyl group or a methyl group; A phenanthrene group unsubstituted or substituted with a phenyl group or a methyl group; A triphenylene group unsubstituted or substituted with a phenyl group or a methyl group; A dibenzofuran group unsubstituted or substituted with a phenyl group or a methyl group; A dibenzothiophene group unsubstituted or substituted with a phenyl group or a methyl group; A carbazole group unsubstituted or substituted with a phenyl group or a methyl group; Or a fluorene group unsubstituted or substituted with a phenyl group or a methyl group.

In the exemplary embodiment of the present specification, Z is a phenyl group; Biphenyl group; Terphenyl group; Phenanthrene group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; A carbazole group unsubstituted or substituted with a phenyl group; Or a fluorene group unsubstituted or substituted with a methyl group.

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

The present specification provides an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1.

The organic light-emitting device of the present specification includes 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 of the organic material layers may include the aforementioned heterocyclic compound.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer 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 a smaller number of organic layers.

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.

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

1 illustrates an organic light-emitting device and is not limited thereto.

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

2 illustrates an organic light emitting device, but is not limited thereto, and an additional organic material layer is further added between the light emitting layer 5 and the second electrode 4 and/or between the light emitting layer 5 and the first electrode 2 Can include.

The additional organic material layer may include at least one layer from a layer selected from a hole injection layer, a hole transport layer, a hole injection and hole transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. have.

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.

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound of Formula 1 above.

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

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound of Formula 1 as a host.

In the exemplary embodiment of the present specification, the emission layer may further include one or more additional hosts other than the heterocyclic compound of Formula 1 above. The additional host may be a conventional known host, but is not limited thereto.

In the exemplary embodiment of the present specification, the emission layer includes the heterocyclic compound of Formula 1 and an additional host in a weight ratio of 99:1 to 1:99. Specifically, it is included in a weight ratio of 70:30 to 30:70, more specifically 40:60.

In an exemplary embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound of Formula 1 as a green host.

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 Can include.

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, the electron transport layer, or the electron injection and transport layer comprises the heterocyclic compound of Formula 1 Can include.

In an exemplary embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound of Formula 1 above.

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 of the organic material layers is formed using the heterocyclic compound.

The present specification also provides a method of manufacturing an organic light-emitting device formed by using the heterocyclic compound of Formula 1 above.

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

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

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. A material that can be used as a cathode after forming an anode by depositing a hole injection layer, a hole transport layer, a light emitting layer, an organic material layer including an electron transport layer, and an organic material layer including the heterocyclic compound of Formula 1 thereon. Can be prepared by depositing. 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.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

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

As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, 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 Formula 1 above. The additional light emitting layer may comprise a host material and a dopant material. Host materials include condensed or non-condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, There are pyrimidine derivatives, but are not limited thereto. The dopant material includes an aromatic heterocyclic compound, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic heterocyclic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted. A compound in which at least one arylvinyl group is substituted on the cyclic arylamine, and one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron 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 conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. A known material may be used without limitation, and may 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 prevents holes from reaching the electron injection layer through 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, etc., but are not limited thereto.

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

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The manufacturing method of the heterocyclic compound of Formula 1 and the manufacturing of an organic light emitting device using them will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

In the above reaction scheme, various kinds of intermediates can be synthesized according to the type and number of substituents appropriately selecting a known starting material by a person skilled in the art. As for the reaction type and reaction conditions, those known in the art may be used.

Manufacturing Example 1

Preparation Example 1-1: Synthesis of Intermediate A3

1) Preparation of Intermediate A1

After dissolving dibenzothiophen-4-ol (50 g, 0.25 mol) in DMF 550 ml in a round bottom flask in a nitrogen atmosphere, NBS (44.9 g, 0.25 mol) was added five times at 0°C, and then at room temperature. The mixture was stirred for 3 hours. Thereafter, the solution was decompressed, dissolved in ethyl acetate, washed with water, and the organic layer was separated and reduced pressure to remove all the solvent. This was used for column chromatography to obtain an intermediate A1 (52.6 g, yield 76%, MS:[M+H] ⁺ = 279).

2) Preparation of intermediate A2

Intermediate A1 (52.6 g, 189 mmol) and (3-chloro-2-fluorophenyl) boronic acid (36.3 g, 208 mmol) were dissolved in 700 mL of tetrahydrofuran. Potassium carbonate 2 M solution (200 mL), bis (tri- t -butylphosphine) palladium (0) (0.97 g, 1.9 mmol) was added and refluxed for 1.5 hours. After the reaction was completed, the mixture was cooled to room temperature, the water layer was separated and removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure and recrystallized using chloroform and ethanol to obtain an intermediate A2. (49.2 g, 79% yield; MS:[M+H] ⁺ =329)

3) Preparation of intermediate A3

Intermediate A2 (49.2 g, 150.0 mmol) and calcium carbonate (62.3 g, 450.0 mmol) were dissolved in 300 mL of N-methyl-2-pyrrolidone, followed by heating and stirring for 2.5 hours. Reduce the temperature to room temperature and filter by reverse precipitation in water. After completely dissolved in dichloromentane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain intermediate A3. (36.2 g, yield 78%; MS:[M+H] ⁺ =309)

Preparation Example 1-2: Synthesis of Intermediate B3

1) Preparation of intermediate B1

The intermediate B1 was prepared in the same manner as the method for preparing the intermediate A1, except that dibenzofuran-4-ol was used instead of dibenzothiophen-4-ol (50.6 g, yield 71%, MS: [M +H] ⁺ = 263).

2) Preparation of intermediate B2

The intermediate B2 was prepared in the same manner as the method of preparing the intermediate A2, except that intermediate B1 was used instead of the intermediate A1 (47.1 g, yield 78%, MS:[M+H] ⁺ = 313).

3) Preparation of intermediate B3

The intermediate B3 was prepared in the same manner as the method of preparing the intermediate A3, except that intermediate B2 was used instead of the intermediate A2 (32.9 g, yield 75%, MS:[M+H] ⁺ = 293).

Preparation Example 2-1: Synthesis of Intermediate A5

1) Preparation of intermediate A4

After dissolving the intermediate A3 (8.0 g, 25.9 mmol), 9H-carbazole (4.5 g, 27.2 mmol) and cesium carbonate (16.9 g, 51.8 mmol) in 160 mL of xylene, bis(dibenzylideneacetone)palladium (0.45 g, 0.80 mmol) and xantfos (0.45 g, 0.80 mmol) were added, followed by heating and stirring for 10 hours. The temperature was lowered to room temperature, filtered to remove remaining salt, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using a mixed solution of chloroform and ethyl acetate, and dried to prepare the intermediate A4 (9.3 g, yield 82%, MS:[M+H] ⁺ = 440).

2) Preparation of Intermediate A5

After dissolving the intermediate A4 (9.3 g, 21.2 mmol) in tetrahydrofuran (200 mL), lowering the temperature to -78°C and slowly adding 2.5 M tert-butyllithium (t-BuLi) (8.6 mL, 21.4 mmol) Added. After stirring at the same temperature for 1 hour, triisopropylborate (7.3 mL, 31.8 mmol) was added, and the mixture was stirred for 7 hours while gradually raising the temperature to room temperature. 2N aqueous hydrochloric acid solution (200 mL) was added to the reaction mixture, followed by stirring at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ethyl ether, and dried in vacuo to prepare intermediate A5. (9.5 g, yield 93%; MS:[M+H] ⁺ =484)

Preparation Example 2-2: Synthesis of Intermediate A7

1) Preparation of intermediate A6

In a nitrogen atmosphere, the intermediate A3 (20.0 g, 65 mmol) and phenylboronic acid (8.7 g, 71 mmol) were dissolved in 350 mL of dioxene, and then tribasic potassium (41.2 g, 194 mmol) was added to 100 mL of water. Dissolved in and added, bis(tri- t -butylphosphine)palladium(0) (0.33 g, 0.6 mmol) was added, followed by heating and stirring for 9 hours. After lowering the temperature to room temperature, the water layer was separated and removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using tetrahydrofuran, and dried to prepare an intermediate A6 (19.1 g, yield 84%, MS:[M+) H] ⁺ = 351)

2) Preparation of intermediate A7

The intermediate A7 was prepared in the same manner as the method for preparing the intermediate A5, except that the intermediate A6 was used instead of the intermediate A4 (19.5 g, yield 91%, MS:[M+H] ⁺ = 395).

Preparation Example 2-3: Synthesis of Intermediate A9

1) Preparation of intermediate A8

The intermediate A8 was prepared in the same manner as the method of preparing the intermediate A6, except that [1,1'-biphenyl]-4-ylboronic acid was used instead of the phenylboronic acid (11.7 g, yield 85%, MS:[M+H] ⁺ = 427).

2) Preparation of intermediate A9

The intermediate A9 was prepared in the same manner as the method of preparing the intermediate A7, except that the intermediate A8 was used instead of the intermediate A6 (11.9 g, yield 92%, MS:[M+H] ⁺ = 471).

Preparation Example 2-4: Synthesis of Intermediate A11

1) Preparation of intermediate A10

The intermediate A10 was prepared in the same manner as the method of preparing the intermediate A6, except that dibenzofuran-3-ylboronic acid was used instead of the phenylboronic acid (12.0 g, yield 84%, MS: [M+H ] ⁺ = 441).

2) Preparation of intermediate A11

The intermediate A11 was prepared in the same manner as the method of preparing the intermediate A7, except that intermediate A10 was used instead of the intermediate A6 (12.1 g, yield 92%, MS:[M+H] ⁺ = 485).

Preparation Example 2-5: Synthesis of Intermediate A13

1) Preparation of intermediate A12

The intermediate A12 was prepared in the same manner as the method of preparing the intermediate A6, except that dibenzothiophen-4-ylboronic acid was used instead of the phenylboronic acid (12.3 g, yield 83%, MS: [M+ H] ⁺ = 457).

2) Preparation of intermediate A13

The intermediate A13 was prepared in the same manner as the method of preparing the intermediate A7, except that the intermediate A12 was used instead of the intermediate A6 (11.9 g, yield 88%, MS: [M+H] ⁺ = 501).

Preparation Example 2-6: Synthesis of Intermediate A15

1) Preparation of Intermediate A14

The intermediate A14 was prepared in the same manner as the method of preparing the intermediate A6, except that (9-phenyl-9H-carbazol-2yl) boronic acid was used instead of the phenylboronic acid (9.9 g, yield 85%) , MS:[M+H] ⁺ = 516).

2) Preparation of Intermediate A15

The intermediate A15 was prepared in the same manner as the method of preparing the intermediate A7, except that the intermediate A14 was used instead of the intermediate A6 (9.7 g, yield 90%, MS: [M+H] ⁺ = 560).

Preparation Example 2-7: Synthesis of Intermediate B5

1) Preparation of intermediate B4

The intermediate B4 was prepared in the same manner as the method of preparing the intermediate A6, except that intermediate B3 was used instead of the intermediate A3 (19.1 g, yield 84%, MS:[M+H] ⁺ = 335).

2) Preparation of intermediate B5

The intermediate B5 was prepared in the same manner as the method of preparing the intermediate A7, except that intermediate B4 was used instead of the intermediate A6 (19.5 g, yield 90%, MS:[M+H] ⁺ = 379).

Preparation Example 2-8: Synthesis of Intermediate B7

1) Preparation of intermediate B6

The intermediate B6 was prepared in the same manner as the method of preparing the intermediate A, except that intermediate B3 and [1,1'-biphenyl]-3-ylboronic acid were used instead of the intermediate A3 and the phenylboronic acid ( 23.3 g, yield 83%, MS:[M+H] ⁺ = 411).

2) Preparation of intermediate B7

The intermediate B7 was prepared in the same manner as the method of preparing the intermediate A7, except that intermediate B6 was used instead of the intermediate A6 (24.0 g, yield 93%, MS: [M+H] ⁺ =455).

Preparation Example 2-9: Synthesis of Intermediate B9

1) Preparation of intermediate B8

Intermediate B8 was prepared in the same manner as in the method of preparing Intermediate A6 except for using Intermediate B3 and dibenzofuran-4-ylboronic acid instead of Intermediate A3 and phenylboronic acid (11.5 g, yield 79%). , MS:[M+H] ⁺ = 425).

2) Preparation of intermediate B9

The intermediate B9 was prepared in the same manner as the method of preparing the intermediate A7, except that intermediate B8 was used instead of the intermediate A6 (11.2 g, yield 88%, MS:[M+H] ⁺ =469).

Preparation Example 2-10: Synthesis of Intermediate B11

1) Preparation of intermediate B10

Intermediate B10 in the same manner as the method of preparing Intermediate A6, except for using Intermediate B3 and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid instead of Intermediate A3 and phenylboronic acid. Was prepared (12.3 g, yield 80%, MS:[M+H] ⁺ = 451).

2) Preparation of intermediate B11

The intermediate B11 was prepared in the same manner as the method of preparing the intermediate A7, except that intermediate B10 was used instead of the intermediate A6 (11.6 g, yield 86%, MS:[M+H] ⁺ =495).

Preparation Example 2-11: Synthesis of Intermediate B13

1) Preparation of intermediate B12

The intermediate B12 was prepared by the same method as the method of preparing the intermediate A6, except that intermediate B3 and (9-phenyl-9H-carbazol-3-yl) boronic acid were used instead of the intermediate A3 and the phenylboronic acid. (11.0 g, yield 81%, MS:[M+H] ⁺ = 500).

2) Preparation of intermediate B13

The intermediate B13 was prepared in the same manner as the method for preparing the intermediate A7, except that intermediate B12 was used instead of the intermediate A6 (10.3 g, yield 86%, MS:[M+H] ⁺ =544).

Preparation Example 2-12: Synthesis of Intermediate B15

1) Preparation of intermediate B14

The intermediate B14 was prepared in the same manner as the method of preparing the intermediate A6, except for using the intermediate B3 and phenanthrene-2-ylboronic acid instead of the intermediate A3 and the phenylboronic acid (12.6 g, yield 85%, MS:[M+H] ⁺ = 435).

2) Preparation of intermediate B15

The intermediate B15 was prepared in the same manner as the method of preparing the intermediate A7, except that intermediate B14 was used instead of the intermediate A6 (12.4 g, yield 89%, MS:[M+H] ⁺ =479).

Synthesis example

Synthesis Example 1: Preparation of Compound 1

In a nitrogen atmosphere, intermediate A5 (7.0 g, 14 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (3.9 g, 14 mmol) were dissolved in 210 ml of tetrahydrofuran and potassium carbonate (6.0 g, 43 mmol) was dissolved in 60 mL of water and added, bis(tri- t -butylphosphine)palladium(0) (0.07 g, 0.1 mmol) was added, followed by heating and stirring for 7 hours. After completion of the reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with dichlorobenzene and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using tetrahydrofuran and dichlorobenzene. The resulting solid was filtered and dried to prepare compound 1. (6.1 g, 63%, MS: [M+H]+ = 671).

According to the preparation method of Synthesis Example 1, the following compounds 2 to 27 were prepared. The structure, shape, yield and MS are shown in Table 1 below.

Experimental example

Experimental Example 1

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,300Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following HI-A was thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer. Subsequently, only the HT-A material was thermally vacuum deposited to a thickness of 800 Å, and the HT-B compound was sequentially vacuum deposited to a thickness of 500 Å to form a hole transport layer. Subsequently, the compound 1 prepared in Synthesis Example 1 as the first host of the light emitting layer and H1 as the second host were vacuum-deposited at a weight ratio of 40:60, and 6% by weight of GD of the sum of the weights of the two hosts to a thickness of 350Å. Subsequently, as a hole blocking layer, the following ET-A was vacuum deposited to a thickness of 50 Å. Subsequently, as an electron transport and injection layer, the following ET-B and Liq were thermally vacuum deposited to a thickness of 250 Å at a ratio of 1:1, and then LiF was vacuum deposited to a thickness of 30 Å. An organic light-emitting device was manufactured by depositing aluminum to a thickness of 1000 Å on the electron transport and injection layer to form a cathode.

Experimental Examples 2 to 15, Comparative Examples 1 and 2

Organic light-emitting devices of Experimental Examples 2 to 15 and Comparative Examples 1 and 2 were manufactured using the same method as in Experimental Example 1, except that the host material was changed as shown in Table 2 below.

By applying a current to the organic light emitting device prepared in Experimental Examples 1 to 15 and Comparative Examples 1 and 2, voltage, efficiency, and life (T95) were measured, and the results are shown in Table 2 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and T95 means the time from the current density 50 mA/cm ² until the initial luminance decreases to 95%.

First host
matter @ 10mA / cm ² @ 50mA / cm ²
Voltage
(V) efficiency
(cd/A) life span
(T95, hr) Experimental Example 1 Compound 1 4.3 69 95 Experimental Example 2 Compound 3 4.3 70 100 Experimental Example 3 Compound 4 4.1 68 104 Experimental Example 4 Compound 7 4.3 71 95 Experimental Example 5 Compound 8 4.3 69 97 Experimental Example 6 Compound 11 4.2 72 99 Experimental Example 7 Compound 12 4.3 70 101 Experimental Example 8 Compound 15 4.2 72 97 Experimental Example 9 Compound 16 4.2 75 93 Experimental Example 10 Compound 18 4.1 70 89 Experimental Example 11 Compound 19 4.2 73 95 Experimental Example 12 Compound 21 4.2 72 92 Experimental Example 13 Compound 22 4.1 76 91 Experimental Example 14 Compound 24 4.2 75 93 Experimental Example 15 Compound 26 4.2 72 90 Comparative Example 1 Compound C1 4.4 62 65 Comparative Example 2 Compound C2 4.4 55 60

As shown in Table 2, it can be seen that in the case of an organic light-emitting device manufactured using the compound of the present specification as a host of the emission layer, compared to the organic light-emitting devices of Comparative Examples 1 and 2, excellent performance in terms of efficiency and lifetime have. In particular, the organic light emitting device according to Experimental Examples 1 to 15 has an efficiency of up to 20% and a lifespan of about 36% to 60% compared to the organic light emitting device according to Comparative Example 1 using compound C1, which is a commonly used phosphorescent host material. As it increased, it was confirmed that it is a compound having high efficiency and long life. In addition, when comparing Experimental Examples 1 to 7 and Experimental Examples 8 to 15, it can be seen that the efficiency and life trends are different depending on the skeleton structure.

1: substrate
2: first electrode
3: organic material layer
4: second electrode
5: light emitting layer

Claims (8)

Heterocyclic compound represented by the following Formula 1:
[Formula 1]

In Formula 1,
X ₁ to X ₃ are the same as or different from each other, and each independently CH or N,
2 or more of X ₁ to X ₃ are N,
Y is O or S,
R is hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Z is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L ₁ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar ₁ and Ar 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,
n is an integer from 0 to 8, and when n is plural, R is the same as or different from each other. The method according to claim 1, wherein the formula 1 is a heterocyclic compound represented by the following formula 2 or 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3, R, Z, X ₁ to X ₃ , Ar ₁ , Ar _2, L ₁ and n are as defined in Formula 1. The method of claim 1, wherein Z is A heterocyclic compound that is 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. The method of claim 1, wherein Ar ₁ and Ar ₂ 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 heterocyclic compound having 3 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of N, O and S. The heterocyclic compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided 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 of the organic material layers includes the heterocyclic compound of any one of claims 1 to 5 Phosphorus organic light emitting device. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes a host and a dopant in a mass ratio of 99:1 to 70:30. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound as a host of the emission layer.

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