KR102225906B1 - Hetero cyclic 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 {HETERO CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0118157 filed with the Korean Intellectual Property Office on October 4, 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 by 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 multilayer 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. When it falls back to the ground, it glows.

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.

The present specification provides a 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,

Two 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, the present specification is an organic light emitting device 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 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 the heterocyclic compound, it is possible to improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light emitting device.

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

Hereinafter, 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 positioned "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 substituent 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; Nitrile group; Halogen 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 heteroyl substituted with an aryl group; a group D, an aryl group substituted with an alkyl group, and the like.

In the present specification, the halogen group may be F, Cl, Br, I, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. 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 a straight chain, branched chain, or cyclic chain. Although the number of carbon atoms of the alkoxy group is not particularly limited, 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, 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 refers to 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 preferable that it has 6-20 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 located 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 the ortho position in 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, 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 including 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 other than carbon and one or more heteroatoms, 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 heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, 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, the heteroarylene group means that the heteroaryl group has 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 above.

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 the 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; An aryl group unsubstituted or substituted with an alkyl group; Or a heteroaryl group unsubstituted or substituted with an alkyl group or 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 group; 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 group; Quinoline group; Or the benzimidazole group is unsubstituted or substituted with deuterium, 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 group; 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 group; Quinoline group; Or the benzimidazole group is a deuterium, 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 deuterium or a phenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms; A dibenzofuran group unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms; A dibenzothiophene group unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms; Or a carbazole group unsubstituted or substituted with deuterium or 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 unsubstituted or substituted with deuterium; Biphenyl group unsubstituted or substituted with deuterium; Dibenzofuran group unsubstituted or substituted with deuterium; Dibenzothiophene group unsubstituted or substituted with deuterium; Or deuterium or a carbazole group unsubstituted or substituted with a phenyl 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 deuterium; 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 heteroarylene group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L ₁ is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, and a divalent dibenzofuran. Group, a divalent dibenzothiophene group, a divalent carbazole group, a divalent pyridine group, a 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 containing any one or more of N, O, or S having 3 to 30 carbon atoms.

In an 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; Benzothiazole group; 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 unsubstituted or substituted with deuterium, 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 an 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; Benzothiazole group; 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 deuterium, 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, dibenzoti It is unsubstituted or substituted with any one or more of an ofene group, a carbazole group, a pyridine group, a pyrimidine group, and a triazine.

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; A substituted or unsubstituted benzothiazole group; Or a substituted or unsubstituted fluorene group.

In the exemplary embodiment of the present specification, Z is a phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a methyl group; A biphenyl group unsubstituted or substituted with deuterium, a phenyl group, or a methyl group; A terphenyl group unsubstituted or substituted with deuterium, a phenyl group, or a methyl group; A phenanthrene group unsubstituted or substituted with deuterium, a phenyl group, or a methyl group; Triphenylene group unsubstituted or substituted with deuterium, phenyl group, or methyl group; Dibenzofuran group unsubstituted or substituted with deuterium, phenyl group, or methyl group; Dibenzothiophene group unsubstituted or substituted with deuterium, phenyl group, or methyl group; Carbazole group unsubstituted or substituted with deuterium, phenyl group, or methyl group; A benzothiazole group unsubstituted or substituted with deuterium, a phenyl group, or a methyl group; Or a fluorene group unsubstituted or substituted with deuterium, a phenyl group, or a methyl group.

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

In an 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.

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 provided 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 at least one additional host 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 includes from 70:30 to 30:70, even more specifically 50:50.

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 above. 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 evaporating. 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 anode 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 compounds), poly[3,4-(ethylene-1,2-dioxy) compounds] (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 that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is 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.

The hole transport material is 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 emissive 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, And pyrimidine derivatives, but are not limited thereto.

Dopant materials 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, 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 aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

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 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, has 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 is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, 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 light emitting layer. Known materials 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 emission layer, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.

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 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 the same 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 following reaction scheme, various types 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.

In the above preparation formula, _{the definitions of Y, Z, L 1} and X ₁ to X ₃ are the same as in Chemical Formula 1.

If the preparation formula described in the examples of the present specification and the intermediates are appropriately combined based on common technical knowledge, all of the heterocyclic compounds of Formula 1 described in the present specification can be prepared.

Manufacturing Example 1

Preparation Example 1-1: Synthesis of Intermediate A4

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 5 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 of 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 (2-chloro-6-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. (43.9 g, yield 71%; MS:[M+H] ⁺ =329)

3) Preparation of intermediate A3

Intermediate A2 (43.9 g, 133 mmol) was dissolved in 550 ml of DMF in a nitrogen atmosphere in a round bottom flask, and NBS (24.0 g, 135 mmol) was added 5 times at 0°C, followed by stirring at room temperature for 2.5 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 of the solvent. This was used for column chromatography to obtain an intermediate A3 (41.3 g, yield 76%; MS:[M+H] ⁺ =407)

4) Preparation of intermediate A4

Intermediate A3 (41.3 g, 102 mmol) and calcium carbonate (42.2 g, 305 mmol) were dissolved in 90 mL of N-methyl-2-pyrrolidone, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, and the filter was performed 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 A4. (30.3 g, yield 77%; MS:[M+H] ⁺ =387)

Preparation Example 1-2: Synthesis of Intermediate B4

1) Preparation of intermediate B1

Intermediate B1 was prepared in the same manner as in the method of preparing Intermediate A1, except that dibenzofuran-4-ol was used instead of dibenzothiophen-4-ol (52.1 g, yield 73%, MS: [M+H ] ⁺ = 263).

2) Preparation of intermediate B2

The intermediate B2 was prepared in the same manner as the intermediate A2, except that intermediate B1 was used instead of intermediate A1 (46.9 g, yield 76%, MS:[M+H] ⁺ = 313).

3) Preparation of intermediate B3

Intermediate B3 was prepared in the same manner as the method of preparing Intermediate A3, except that Intermediate B2 was used instead of Intermediate A2 (42.9 g, yield 73%, MS:[M+H] ⁺ = 391).

4) Preparation of intermediate B4

The intermediate B4 was prepared in the same manner as the method of preparing the intermediate A4, except that the intermediate B3 was used instead of the intermediate A3 (27.0 g, yield 66%, MS:[M+H] ⁺ = 371).

Preparation Example 2-1: Synthesis of Intermediate A6

1) Preparation of intermediate A5

In a nitrogen atmosphere, intermediate A4 (20.0 g, 62 mmol) and phenylboronic acid (6.3 g, 52 mmol) were dissolved in 560 ml of tetrahydrofuran, and potassium carbonate (21.4 g, 155 mmol) was added to 100 mL of water. After melting and adding, tetrakis-(triphenylphosphine)palladium (0.93 g, 1.8 mmol) was added, followed by heating and stirring for 7 hours. The temperature was lowered 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 the intermediate A5 (15.7 g, yield 79%, MS: [M +H] ⁺ = 385).

2) Preparation of Intermediate A6

In a nitrogen atmosphere, chemical intermediate A6 (15.7 g, 41 mmol), bis(pinacolato)diboron (10.9 g, 43 mmol) and potassium acetate (8.0 g, 82 mmol) were mixed, added to 300 ml of dioxane, and stirred while Heated. In a refluxed state, bis(dibenzylidineacetone)palladium (0.71g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.5 mmol) were added, followed by heating and stirring for 11 hours. After the reaction was completed, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure and recrystallized with ethyl acetate, the intermediate A6 was prepared (15.2 g, yield 78%, MS:[M+H] ⁺ =474).

Preparation Example 2-2: Synthesis of Intermediate A8

1) Preparation of intermediate A7

Intermediate A7 was prepared in the same manner as in the method of preparing Intermediate A5, except that (phenyl-d5) boronic acid was used instead of phenylboronic acid (12.0 g, yield 80%, MS: [M+H] ⁺ = 390 ).

2) Preparation of intermediate A8

Intermediate A8 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate A7 was used instead of Intermediate A5 (11.2 g, yield 75%, MS:[M+H] ⁺ = 482).

Preparation Example 2-3: Synthesis of Intermediate A10

1) Preparation of Intermediate A9

Intermediate A9 was prepared in the same manner as in the method of preparing Intermediate A5, except that [1,1'-biphenyl]-3-ylboronic acid was used instead of phenylboronic acid (14.1 g, yield 80%, MS:[ M+H] ⁺ = 461).

2) Preparation of Intermediate A10

Intermediate A10 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate A9 was used instead of Intermediate A5 (12.9 g, yield 76%, MS:[M+H] ⁺ = 553).

Preparation Example 2-4: Synthesis of Intermediate A12

1) Preparation of intermediate A11

Intermediate A11 was prepared in the same manner as in the method of preparing Intermediate A5, except that [1,1'-biphenyl]-4-ylboronic acid was used instead of phenylboronic acid (14.8 g, yield 83%, MS:[ M+H] ⁺ = 461).

2) Preparation of intermediate A12

Intermediate A12 was prepared in the same manner as the method of preparing Intermediate A6 except for using Intermediate A11 instead of Intermediate A5 (14.0 g, yield 79%, MS:[M+H] ⁺ = 553).

Preparation Example 2-5: Synthesis of Intermediate A14

1) Preparation of intermediate A13

Intermediate A13 was prepared in the same manner as the method of preparing Intermediate A5, except that dibenzofuran-3-ylboronic acid was used instead of phenylboronic acid (6.8 g, yield 79%, MS:[M+H] ⁺ = 475).

2) Preparation of intermediate A14

Intermediate A14 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate A13 was used instead of Intermediate A5 (6.4 g, yield 76%, MS:[M+H] ⁺ = 567).

Preparation Example 2-6: Synthesis of Intermediate A16

1) Preparation of intermediate A15

Intermediate A15 was prepared in the same manner as in the method of preparing Intermediate A5, except that (9-phenyl-9H-carbazol-4-yl) boronic acid was used instead of phenylboronic acid (7.7 g, yield 78%, MS :[M+H] ⁺ = 550).

2) Preparation of intermediate A16

Intermediate A16 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate A15 was used instead of Intermediate A5 (7.2 g, yield 80%, MS:[M+H] ⁺ = 642).

Preparation Example 2-7: Synthesis of Intermediate A18

1) Preparation of intermediate A17

Intermediate A4 (7.0 g, 18.1 mmol), 9H-carbazole (3.0 g, 18.1 mmol) and cesium carbonate (11.8 g, 36.1 mmol) were dissolved in 140 mL of toluene, and bis(dibenzylidineacetone)palladium (0.31 g, 0.5 mmol) and Zantfos (0.31 g, 0.5 mmol) were added, followed by heating and stirring for 8 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 A17 (6.1 g, yield 71%, MS:[M+H] ⁺ = 474).

2) Preparation of intermediate A18

Intermediate A18 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate A17 was used instead of Intermediate A5 (5.8 g, yield 80%, MS:[M+H] ⁺ = 566).

Preparation Example 2-8: Synthesis of Intermediate B6

1) Preparation of intermediate B5

The intermediate B5 was prepared in the same manner as the intermediate A5, except that intermediate B4 was used instead of intermediate A4 (16.9 g, yield 85%, MS:[M+H] ⁺ = 369).

2) Preparation of intermediate B6

Intermediate B6 was prepared in the same manner as in the method of preparing Intermediate A6, except that Intermediate B5 was used instead of Intermediate A5 (17.1 g, yield 81%, MS:[M+H] ⁺ = 461).

Preparation Example 2-9: Synthesis of Intermediate B8

1) Preparation of intermediate B7

Intermediate B7 was prepared in the same manner as in the method of preparing Intermediate A5 except for using Intermediate B4 and (phenyl-d5) boronic acid instead of Intermediate A4 and phenylboronic acid (12.3 g, yield 81%, MS: [M +H] ⁺ = 374).

2) Preparation of intermediate B8

The intermediate B8 was prepared in the same manner as the intermediate A6, except that intermediate B7 was used instead of intermediate A5 (12.0 g, yield 78%, MS:[M+H] ⁺ = 466).

Preparation Example 2-10: Synthesis of Intermediate B10

1) Preparation of intermediate B9

Intermediate B9 was prepared in the same manner as the method of preparing Intermediate A5 except for using Intermediate B4 and [1,1'-biphenyl]-3-ylboronic acid instead of Intermediate A4 and phenylboronic acid (14.4 g, yield 80%, MS:[M+H] ⁺ = 445).

2) Preparation of intermediate B10

Intermediate B10 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate B9 was used instead of Intermediate A5 (13.8 g, yield 80%, MS:[M+H] ⁺ = 537).

Preparation Example 2-11: Synthesis of Intermediate B12

1) Preparation of intermediate B11

Intermediate B11 was prepared in the same manner as in the method of preparing Intermediate A5 except for using Intermediate B4 and [1,1'-biphenyl]-4-ylboronic acid instead of Intermediate A4 and phenylboronic acid (14.9 g, yield 83%, MS:[M+H] ⁺ = 445).

2) Preparation of intermediate B12

The intermediate B12 was prepared in the same manner as the intermediate A6 except for using the intermediate B11 instead of the intermediate A5 (14.5 g, yield 81%, MS:[M+H] ⁺ = 537).

Preparation Example 2-12: Synthesis of Intermediate B14

1) Preparation of intermediate B13

Intermediate B13 was prepared in the same manner as the method of preparing Intermediate A5 except for using Intermediate B4 and dibenzothiophen-4-ylboronic acid instead of Intermediate A4 and phenylboronic acid (7.1 g, yield 80%, MS: [M+H] ⁺ = 475).

2) Preparation of intermediate B14

Intermediate B14 was prepared in the same manner as in the method of preparing Intermediate A6, except that Intermediate B13 was used instead of Intermediate A5 (6.3 g, yield 74%, MS:[M+H] ⁺ = 567).

Preparation Example 2-13: Synthesis of Intermediate B16

1) Preparation of intermediate B15

Intermediate B15 was prepared in the same manner as in the method of preparing Intermediate A5 except for using Intermediate B4 and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid instead of Intermediate A4 and phenylboronic acid ( 6.2 g, yield 68%, MS:[M+H] ⁺ = 485).

2) Preparation of intermediate B16

The intermediate B16 was prepared in the same manner as the intermediate A6, except that intermediate B15 was used instead of intermediate A5 (5.7 g, yield 77%, MS:[M+H] ⁺ = 577).

Preparation Example 2-14: Synthesis of Intermediate B18

1) Preparation of intermediate B17

Intermediate B17 was prepared in the same manner as in the method of preparing Intermediate A5 except for using Intermediate B4 and (9-phenyl-9H-carbazol-3-yl) boronic acid instead of Intermediate A4 and phenylboronic acid (7.0 g , Yield 70%, MS:[M+H] ⁺ = 534).

2) Preparation of intermediate B18

Intermediate B18 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate B17 was used instead of Intermediate A5 (6.9 g, yield 84%, MS:[M+H] ⁺ = 626).

Preparation Example 2-15: Synthesis of Intermediate B20

1) Preparation of intermediate B19

Intermediate B19 was prepared in the same manner as the method of preparing Intermediate A17, except that Intermediate B4 was used instead of Intermediate A4 (6.0 g, yield 70%, MS:[M+H] ⁺ = 458).

2) Preparation of intermediate B20

Intermediate B20 was prepared in the same manner as the method of preparing Intermediate A6, except that Intermediate B19 was used instead of Intermediate A5 (5.8 g, yield 80%, MS:[M+H] ⁺ = 550).

Synthesis example

Synthesis Example 1: Preparation of Compound 1

In a nitrogen atmosphere, intermediate A5 (5.0 g, 10.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.8 g, 10.5 mmol) were dissolved in 150 ml of tetrahydrofuran and potassium carbonate (4.4 g, 31.5 mmol) was dissolved in 50 mL of water and added, bis(tri- t -butylphosphine)palladium(0) (0.11 g, 0.2 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. (3.8 g, 62%, MS: [M+H]+ = 582).

According to the preparation method of Synthesis Example 1, the following compounds 2 to 33 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 put 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 washing 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 prepared ITO transparent electrode, the following HI-A was thermally vacuum deposited to a thickness of 500Å 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 vacuum-deposited to a thickness of 500 Å to sequentially form a hole transport layer and an electron blocking layer. Subsequently, the compound 1 prepared from Synthesis Example 1 as the first host of the emission layer, H1 as the second host, and the phosphorescent dopant GD were vacuum-deposited to a thickness of 350Å at a weight ratio of 47:47:6. Subsequently, an ET-A material was vacuum deposited as a hole blocking layer on the emission layer to a thickness of 50 Å, and an ET-B material and LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron transport layer having a thickness of 250 Å. Lithium pyride (LiF) having a thickness of 10 Å was sequentially deposited on the electron transport layer, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light-emitting device.

Experimental Examples 2 to 25 and Comparative Example 1

The organic light emitting devices of Experimental Examples 2 to 25 and Comparative Example 1 were manufactured using the same method as in Experimental Example 1, except that the first host material was changed as shown in Table 1 below.

By applying a current to the organic light emitting device prepared in Experimental Examples 1 to 25 and Comparative Example 1, voltage, efficiency, and lifetime (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 until the initial luminance decreases to 95% at the current density of 50 mA/cm ^2.

First host
matter @ 10mA / cm ² @ 50mA / cm ² Voltage
(V) efficiency
(cd/A) life span
(T95, hr) Experimental Example 1 Compound 1 4.6 54.7 95 Experimental Example 2 Compound 2 4.6 54.6 104 Experimental Example 3 Compound 4 4.7 54.5 100 Experimental Example 4 Compound 5 4.7 55.2 98 Experimental Example 5 Compound 7 4.7 53.5 95 Experimental Example 6 Compound 9 4.6 56.0 96 Experimental Example 7 Compound 10 4.6 54.4 98 Experimental Example 8 Compound 11 4.7 58.0 90 Experimental Example 9 Compound 13 4.6 54.4 93 Experimental Example 10 Compound 14 4.4 52.6 102 Experimental Example 11 Compound 15 4.6 55.1 98 Experimental Example 12 Compound 16 4.5 54.2 94 Experimental Example 13 Compound 17 4.5 55.6 87 Experimental Example 14 Compound 18 4.5 55.5 102 Experimental Example 15 Compound 19 4.5 55.7 96 Experimental Example 16 Compound 20 4.6 56.2 92 Experimental Example 17 Compound 22 4.5 59.1 88 Experimental Example 18 Compound 24 4.5 57.2 93 Experimental Example 19 Compound 25 4.5 55.0 98 Experimental Example 20 Compound 27 4.6 56.3 96 Experimental Example 21 Compound 28 4.5 56.0 90 Experimental Example 22 Compound 30 4.5 56.4 95 Experimental Example 23 Compound 31 4.4 57.1 100 Experimental Example 24 Compound 32 4.5 56.2 98 Experimental Example 25 Compound 33 4.5 58.7 85 Comparative Example 1 Compound C1 4.9 40.1 65

As shown in Table 2 above, in the case of an organic light-emitting device manufactured using the heterocyclic compound according to an exemplary embodiment of the present specification as a host of the emission layer, compared to the organic light-emitting device of Comparative Example 1, excellent in terms of voltage, efficiency, and lifetime. We could see what it shows performance

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,
Two 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 substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, which is a heterocyclic compound. 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 heterocyclic compound having 3 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S. The heterocyclic compound of 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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