KR20200134148A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, and to an organic light-emitting device comprising the same, wherein the organic light-emitting device is capable of improving high color purity and/or service life properties by using the compound.

Description

Compound and organic light-emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention claims the benefit of the filing date of Korean Patent No. 10-2019-0059531 filed with the Korean Intellectual Property Office on May 21, 2019, the entire contents of which are incorporated herein.

The present specification relates to a 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.

The external quantum efficiency (EQE; ηext) of the light-emitting material used in the light-emitting material layer can be calculated by the following equation.

(η _{S /T} is the exciton/triplet ratio, Γ is the charge balance factor; Φ is the radial quantum efficiency; η _{out -coupling} is the light-extraction efficiency (out) -coupling efficiency)) The exciton generation efficiency (η _S/T ) is the rate at which the generated excitons are converted into light, and in the case of a fluorescent material, it has a limiting value of 0.25. In theory, when holes and electrons meet to form excitons, the singlet exciton in the form of a paired spin and the triplet exciton in the form of an unpaired spin are formed according to the arrangement of the spins. It is produced in a ratio of 1:3. In fluorescent materials, only singlet excitons participate in light emission, and 75% of the remaining triplet excitons do not participate in light emission. The charge balance factor (γ) refers to the balance between holes and electrons forming excitons, and generally has a value of '1' assuming 100% 1:1 matching. Radiation quantum efficiency (Φ) is a value related to the luminous efficiency of a light-emitting material, and in a host-dopant system, it depends on photoluminescence (PL) of the dopant. Light-extraction efficiency (η _out-coupling ) is the ratio of light extracted to the outside among the light emitted from a luminescent material. In general, when a thin film is formed by thermally depositing an isotropic type of light-emitting material, individual light-emitting molecules do not have a certain orientation and exist in a disordered state. Light-extraction efficiency in such a random orientation state is generally assumed to be a value of 0.2. Therefore, when the four elements shown in Equation 1 are combined, the maximum luminous efficiency of an organic light-emitting diode using a fluorescent material is only about 5%. Phosphorescent materials have been developed to solve the low efficiency of fluorescent materials. This is because phosphorescent materials have a light-emitting mechanism that converts both singlet energy and triplet energy into light. However, metal complex compounds commonly used as phosphorescent materials are not only expensive, but also have a very short lifespan, so there is a limit to commercialization. In particular, in the case of a blue phosphorescent material, required luminous efficiency and reliability are not met. Accordingly, in a fluorescent material satisfying reliability, development of a material capable of increasing luminous efficiency by increasing quantum efficiency is required.

US Patent Application Publication No. 2004-0251816

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

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L is a substituted or unsubstituted N-containing monocyclic heteroarylene group,

A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

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

At least one of X ₁ to X ₃ is N,

R is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or , Can be combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted hetero ring,

a and b are each an integer of 0 to 4,

When a or b is plural, the substituents in parentheses are the same as or different from each other.

In addition, the present invention is 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 compound.

The 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 compound, high color purity and/or lifespan characteristics may be improved in the organic light emitting device.

In particular, the structure of the present invention has excellent electron transport capability due to triazine. The electron transport ability is further improved by the nitrogen atom contained in the linker. Charges are transferred from the portion having the n-type property of the triazine-linker to the portion having the p-type property to form an intra-charge-transfer state. When a material having such a property is used as a dopant for an emission layer of an organic light-emitting device, it has a remarkable effect on both hole transfer and electron transfer, thereby exhibiting characteristics of low voltage, high efficiency, and long life. In particular, the compound of the present invention increases the rate and speed at which the excitons generated in the triplet move to the singlet by the reverse interphase transfer (RISC), so that the time that the excitons stay in the triplet decreases, so the efficiency and lifespan of the organic light emitting device There is a further increasing advantage of this.

1 and 2 illustrate 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 compound represented by Chemical Formula 1.

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; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with 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 no substituent. 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 heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

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 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; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenalenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group or the like, 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, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group 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, that is, 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, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrole group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyrido pyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazolyl group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline; Isoxazolyl group; Thiadiazolyl group; There may be a phenothiazinyl group and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group except that it is divalent.

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 ₂ are N, and X ₂ is CCN.

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

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

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

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

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

In the exemplary embodiment of the present specification, L is a substituted or unsubstituted N-containing monocyclic heteroarylene group.

In the exemplary embodiment of the present specification, L is a substituted or unsubstituted N-containing monocyclic heteroarylene group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L is an N-containing monocyclic heteroarylene group.

In the exemplary embodiment of the present specification, L is an N-containing monocyclic heteroarylene group, and is unsubstituted or substituted with any one or more selected from deuterium, nitrile group, haloalkyl group, and alkyl group.

In the exemplary embodiment of the present specification, L is a divalent pyridine group, a divalent pyrimidine group, or a divalent triazine group, and the divalent pyridine group, a divalent pyrimidine group, or a divalent triazine group is deuterium, It is unsubstituted or substituted with any one or more selected from a nitrile group, a haloalkyl group, and an alkyl group.

In the exemplary embodiment of the present specification, L is a divalent pyridine group substituted or unsubstituted with any one or more selected from deuterium, a nitrile group, a haloalkyl group, and an alkyl group.

In the exemplary embodiment of the present specification, L is a divalent pyridine group unsubstituted or substituted with any one or more selected from deuterium, a nitrile group, a haloalkyl group having 1 to 10 carbon atoms, and an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, L is substituted or unsubstituted with any one or more selected from deuterium, nitrile group, CF ₃ , methyl group, ethyl group, propyl group, isopropyl group, butyl group, and terbutyl group. It is a divalent pyridine group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or It is an unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, an alkyl group, an aryl group, or a heteroaryl group.

In the exemplary embodiment of the present specification, A ₁ and A 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.

In the exemplary embodiment of the present specification, A ₁ and A 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 group having 3 to 30 carbon atoms. It is an aryl group.

In the exemplary embodiment of the present specification, A ₁ and A 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.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or Unsubstituted terphenyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthrene group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorene group, substituted or unsubstituted carbazole group, substituted Or an unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

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

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted dibenzofuran group to be.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted Substituted or unsubstituted with a heteroaryl group, a substituted or unsubstituted phosphine oxide group, or a substituted or unsubstituted silyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or non-substituted It is unsubstituted or substituted with a cyclic heteroaryl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is substituted or unsubstituted with deuterium, nitrile group, halogen group, or substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is substituted or unsubstituted with an alkyl group.

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

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, or a dibenzofuran group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, or a dibenzofuran group, and the phenyl group is a methyl group, an ethyl group, a propyl group, an isopropyl group , Unsubstituted or substituted with a butyl group, a terbutyl group, a pentyl group, or a hexyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently substituted or provided with any one or more selected from a methyl group, an ethyl group, a propyl group, an isopropyl group, and a terbutyl group. A cyclic phenyl group; Biphenyl group; Or a dibenzofuran group.

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

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C1-C10 alkyl group; 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, or combined with an adjacent group to form a substituted or unsubstituted heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group; Or a heteroaryl group, or combined with an adjacent group to form a heterocycle,

The aryl group; Or a heteroaryl group, or a heterocycle formed by bonding with an adjacent group is in the group consisting of deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group It is unsubstituted or substituted with one or more selected substituents.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group; Or a substituted or unsubstituted heteroaryl group with an aryl group, or combined with an adjacent group to form a substituted or unsubstituted heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group, or combined with an adjacent group to form a heterocycle substituted or unsubstituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group. .

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, Fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, It is unsubstituted or substituted with one or more substituents selected from the group consisting of a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, Fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group is an aryl group. Substituted or unsubstituted.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a benzocarbazole group, a dibenzofuran group, or a dibenzothiophene And

The carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group is unsubstituted or substituted with an aryl group.

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

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

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

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

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; It is a carbazole group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, or a benzocarbazole group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

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

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

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

In the exemplary embodiment of the present specification, R ₁ and R ₂ form a substituted heterocycle by bonding with an adjacent group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form a substituted N-containing heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form a substituted N-containing bicyclic heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form an N-containing bicyclic heterocycle substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form an N-containing bicyclic heterocycle substituted with a deuterated aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form an N-containing bicyclic heterocycle substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form an N-containing bicyclic heterocycle substituted with a deuterated aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form an N-containing bicyclic heterocycle substituted with a phenyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form an N-containing bicyclic heterocycle substituted with a deuterated phenyl group.

The "deuterated" means that a replaceable hydrogen is substituted with deuterium.

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

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 a member is in contact with the other member, but also the case where another member exists between the two members.

The organic light-emitting device of the present invention 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 compound.

For example, the structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting 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 shows a first electrode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7), an electron injection layer (8) and a second electrode ( 4) The structure of the organic light emitting device in which these are sequentially stacked is illustrated. The compound of the present invention is preferably contained in the light emitting layer (3).

In one embodiment of the present invention, the emission layer includes the compound.

In an exemplary embodiment of the present invention, the emission layer includes the compound as a dopant of the emission layer.

In an exemplary embodiment of the present invention, the emission layer may include the compound as a dopant for the emission layer, and may further include an additional dopant.

In an exemplary embodiment of the present invention, the emission layer may include the compound as a dopant for the emission layer, and may further include an additional fluorescent dopant.

In one embodiment of the present invention, the light emitting layer may use a carbazole-based organic compound as a host compound, but is not limited thereto.

In one embodiment of the present invention, the emission layer includes a host and a dopant in a mass ratio of 95:5 to 10:90.

In an exemplary embodiment of the present invention, the emission layer includes a host and a dopant in a mass ratio of 95:5 to 30:70.

In an exemplary embodiment of the present invention, the emission layer includes a compound represented by the following Formula A as a host.

[Formula A]

In the formula A,

XX1 and XX2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent Can be combined with a group to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted hetero ring,

L101 is each independently a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

x1 is an integer of 0 to 8, and when x1 is 2 or more, XX1 is the same as or different from each other,

x2 is an integer of 0 to 8, and when x2 is 2 or more, XX2 is the same as or different from each other,

m101 is an integer of 1 to 10, and when m101 is 2 or more, L101 is the same as or different from each other.

In the exemplary embodiment of the present specification, L101 is a substituted or unsubstituted arylene group.

In the exemplary embodiment of the present specification, L101 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L101 is an arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present invention, L101 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent anthracene group, a substituted Or an unsubstituted divalent phenanthrene group, a substituted or unsubstituted divalent triphenylene group, a substituted or unsubstituted divalent fluorene group, or a substituted or unsubstituted divalent pyrene group.

In an exemplary embodiment of the present invention, L101 is a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent fluorene group, or a divalent. It's a pyrengi.

In the exemplary embodiment of the present specification, L101 is a divalent biphenyl group.

In the exemplary embodiment of the present specification, L101 is a phenylene group.

In the exemplary embodiment of the present specification, XX1 and XX2 are hydrogen.

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

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 contains the compound of Formula 1 I can.

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 compound of Formula 1 above.

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

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

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

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 organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer including the compound of Formula 1 thereon to form an anode. 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 metal and oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (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. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., 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 light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Dopant materials include aromatic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic 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 The arylamine is a compound in which at least one arylvinyl group is substituted, 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, 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, and a material having high mobility for electrons is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used 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 hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum 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 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.

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

When 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 compounds of Formula 1 described in the present specification can be prepared.

Intermediate Synthesis Example 1. (Synthesis of Intermediate b)

5-bromo-2-fluoronicotinonitrile (5.00 g, 25.00 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-ratio ( 1,3,2-dioxaborolane) (7.50 g, 30.00 mmol), [bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.10 g, 1.50 mmol) and potassium acetate ( 7.30 g, 75.00 mmol) was dissolved in 1,4-dioxane under reflux reaction to synthesize intermediate a (7.30 g, yield: 65%).

Intermediate a (3.00, 12.10 mmol), 2,4-bis(4-(tert-butyl)phenyl)-6-chloro-1,3,5-triazine (4.14 g, 10.90 mmol), potassium carbonate (4.90 g , 21.90 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.30 g, 0.30 mmol) were dissolved in tetrahydrofuran and water for 12 hours under reflux reaction, and intermediate b (3.60g, yield: 90%) Was synthesized.

Synthesis Example 1. (Synthesis of Compound 1)

Intermediate b (1.31g, 2.83mmol), 12-phenyl-5,12-dihydroindole[3,2-a]carbazole (0.94g, 2.83mmol) and cesium carbonate (2.80g, 8.49mmol) in 10ml The mixture added to dimethylformamide was refluxed for 3 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO _4, and evaporated to evaporate the solvent, and the obtained material was purified by column chromatography (dichloromethane/hexane (1:1)) to prepare compound 1 (1.80g, yield: 82%). I did.

MS (APCI) m/z 777.36 [(M+H) ⁺ ].

Synthesis Example 2. (Synthesis of Compound 2)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 11-(phenyl-d5)-11,12-dihydroindolo Compound 2 (1.52g, yield: 80%) was prepared in the same manner except that [2,3-a]carbazole was used and intermediate c was used instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 670.26 [(M+H) ⁺ ].

Synthesis Example 3. (Synthesis of Compound 3)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 5-phenyl-5,8-dihydroindolo[2,3] Compound 3 (1.51g, yield: 80%) was prepared in the same manner as -c]carbazole and intermediate d instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 665.23 [(M+H) ⁺ ].

Synthesis Example 4. (Synthesis of Compound 4)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 11-(phenyl-d5)-11,12-dihydroindolo Compound 4 (1.32g, yield: 64%) was prepared in the same manner except that [2,3-a] carbazole was used and intermediate e was used instead of intermediate b (1.31 g, 2.83 mmol).

MS (APCI) m/z 726.23 [(M+H) ⁺ ].

Synthesis Example 5. (Synthesis of Compound 5)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 9-phenyl-9H,9'H-3,3'-bi Compound 5 (1.54g, yield: 68%) was prepared in the same manner, except that carbazole was used and intermediate f was used instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 799.34 [(M+H) ⁺ ].

Synthesis Example 6. (Synthesis of Compound 6)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 11-(phenyl-d5)-11,12-dihydroindolo Compound 6 (1.88g, yield: 84%) was prepared in the same manner as using [2,3-a]carbazole, and using intermediate g instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 789.29 [(M+H) ⁺ ].

Synthesis Example 7. (Synthesis of Compound 7)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 10-(9H-carbazol-yl)-7-phenyl-7H Compound 7 (1.44g, yield: 56%) was prepared in the same manner except that -benzo[c]carbazole was used, and intermediate h was used instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 910.30 [(M+H) ⁺ ].

Synthesis Example 8. (Synthesis of Compound 8)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 9-phenyl-9H,9'H-3,3'-bi Compound 8 (1.56g, yield: 64%) was prepared in the same manner except that carbazole was used and intermediate i was used instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 862.30 [(M+H) ⁺ ]

Synthesis Example 9. (Synthesis of Compound 9)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 5-(phenyl-d5)-5,7-dihydroindolo Compound 9 (1.71g, yield: 70%) was prepared in the same manner except for using [2,3-b]carbazole and using intermediate j instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 803.27 [(M+H) ⁺ ]

Synthesis Example 10. (Synthesis of Compound 10)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 11-(phenyl-d5)-11,12-dihydroindolo Compound 10 (1.17g, yield: 56%) was prepared in the same manner except for using [2,3-a] carbazole and using intermediate k instead of intermediate b (1.31 g, 2.83 mmol).

MS (APCI) m/z 735.32 [(M+H) ⁺ ]

Synthesis Example 11. (Synthesis of Compound 11)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 9-phenyl-9H,9'H-3,3'-bi Compound 11 (1.41g, yield: 62%) was prepared in the same manner except that carbazole was used and intermediate l was used instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 806.32 [(M+H) ⁺ ]

Synthesis Example 12. (Synthesis of Compound 11)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 9-phenyl-9H,9'H-3,3'-bi Compound 12 (1.55g, yield: 68%) was prepared in the same manner except that carbazole was used and intermediate m was used instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 806.32 [(M+H) ⁺ ]

Synthesis Example 13. (Synthesis of Compound 13)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 5-phenyl-5,12-dihydroindolo[3,2] Compound 13 (1.17g, yield: 62%) was prepared in the same manner as -a]carbazole and intermediate c instead of intermediate b (1.31g, 2.83mmol).

MS (APCI) m/z 665.23 [(M+H) ⁺ ].

Synthesis Example 14. (Synthesis of Compound 14)

In Synthesis Example 1, instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol), 5-phenyl-5,8-dihydroindolo[2,3] Compound 14 (1.23g, yield: 56%) was prepared in the same manner as -c] carbazole was used.

MS (APCI) m/z 777.98 [(M+H) ⁺ ].

Example 1

After patterning so that the light emitting area of the ITO (indium tin oxide) glass had a size of 3 mm × 3 mm, it was washed. After mounting the substrate in a vacuum chamber, make the base pressure 1x10 ^-6 torr, and then form HT-1 with a thickness of 100Å as a hole injection layer on the anode ITO, but compound A-1 with a doping concentration of 25% by weight. Doped. Subsequently, HT-1 was formed to a thickness of 600 Å as a hole transport layer, and 1,3-bis (N-carbazolyl) benzene (1,3-bis (N-carbazolyl) benzene (mCP)) was formed to a thickness of 50 Å. I did. Next, the compound 1 of Synthesis Example 1 was used as a dopant on m-CBP as a host as a light emitting layer, and deposited so that the weight ratio was 8:2, and diphenyl[4-(triphenylsilyl)phenyl]phosphine was used as the electron transport layer. Oxide (diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide )(TSPO1, 5 nm)/ 2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H -Benzimidazole) (2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) )(TPBi, 20 nm was deposited as an electron injection layer. LiF was formed to a thickness of 10 Å, and Al was sequentially formed to a thickness of 800 Å as a cathode to fabricate an organic light emitting device.

Example 2

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 2 instead of Compound 1.

Example 3

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 3 instead of Compound 1.

Example 4

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 4 instead of Compound 1.

Example 5

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 5 instead of Compound 1.

Example 6

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 6 instead of Compound 1.

Example 7

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 7 instead of Compound 1.

Example 8

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 8 instead of Compound 1.

Example 9

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 9 instead of Compound 1.

Example 10

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 10 instead of Compound 1.

Example 11

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 11 instead of Compound 1.

Example 12

Under the same process conditions as in Example 1, only using Compound 12 instead of Compound 1 was used to manufacture an organic light-emitting device.

Example 13

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 13 instead of Compound 1.

Example 14

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 14 instead of Compound 1.

Comparative Example 1

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 1 instead of Compound 1.

[Comparative compound 1]

Comparative Example 2

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by using only Comparative Compound 2 instead of Compound 1.

[Comparative compound 2]

Comparative Example 3

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 3 instead of Compound 1.

[Comparative compound 3]

Comparative Example 4

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 4 instead of Compound 1.

[Comparative compound 4]

Comparative Example 5

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 5 instead of Compound 1.

[Comparative compound 5]

Comparative Example 6

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by using only Comparative Compound 6 instead of Compound 1.

[Comparative compound 6]

Voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light emitting devices prepared in Examples 1 to 14 and Comparative Examples 1 to 6, respectively, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the lifetime (T95) means the time until the initial luminance at 3,000 nit decreases to 95%.

Voltage (V) (@10mA/cm ² ) Efficiency (cd/A) (@10mA/cm ² ) Life (T95, hr) Example 1 4.3 46.8 240 Example 2 4.3 46.2 280 Example 3 4.4 45.6 264 Example 4 4.6 47.8 226 Example 5 4.5 47.2 296 Example 6 4.5 45.2 280 Example 7 4.2 42.2 342 Example 8 4.4 40.8 326 Example 9 4.3 40.2 318 Example 10 4.5 42.0 330 Example 11 4.2 44.8 232 Example 12 4.4 46.4 260 Example 13 4.6 45.6 250 Example 14 4.2 44.8 208 Comparative Example 1 5.0 32.6 160 Comparative Example 2 5.0 29.8 184 Comparative Example 3 5.2 34.4 180 Comparative Example 4 5.0 32.6 172 Comparative Example 5 5.1 33.8 158 Comparative Example 6 5.2 36.4 158

As shown in Table 1, Examples 1 to 14 in which the compound of Formula 1 of the present invention was used as a dopant for the light emitting layer of an organic light emitting device were excellent in low voltage, high efficiency and long life compared to Comparative Examples 1 to 6. Characteristics.

Specifically, from Table 1, the compound containing the heteroarylene linker of Formula 1 of the present invention has excellent effects of low voltage, high efficiency and long life compared to the compound not containing the heteroarylene linker of Comparative Compounds 1 to 6 Confirmed.

Example 15

After patterning so that the light emitting area of the ITO (indium tin oxide) glass had a size of 3 mm × 3 mm, it was washed. After mounting the substrate in a vacuum chamber, the base pressure is 1x10 ^-6 torr, and then the HT-1 is formed to a thickness of 100 Å as a hole injection layer on the anode ITO, but the compound A-1 is doped with 25% by weight. Doped with concentration. Subsequently, HT-1 was formed to a thickness of 600 Å as a hole transport layer, and 1,3-bis (N-carbazolyl) benzene (mCP) was formed to a thickness of 50 Å. Next, the compound 1 and the fluorescent dopant compound-D were deposited to a weight ratio of 79:20:1 using m-CBP as a light emitting layer as a dopant, and diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide as an electron transport layer. (TSPO1, 5 nm)/2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi, 20 nm) was deposited as an electron injection layer. LiF was formed to a thickness of 10 Å, and Al was sequentially formed to a thickness of 800 Å as a cathode to fabricate an organic light emitting device.

[Compound-D]

Example 16

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Compound 3 instead of Compound 1.

Example 17

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Compound 6 instead of Compound 1.

Example 18

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Compound 14 instead of Compound 1.

Comparative Example 7

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by using only Comparative Compound 1 instead of Compound 1.

Comparative Example 8

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by using only Comparative Compound 3 instead of Compound 1.

Voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light-emitting devices prepared in Examples 15 to 18 and Comparative Examples 7 and 8, respectively, and the results are shown in Table 2 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the lifetime (T95) means the time until the initial luminance at 3,000 nit decreases to 95%.

Voltage (V)
(@10mA/cm ² ) Efficiency (cd/A) (@10mA/cm ² ) Life (T95, hr) Example 15 4.4 47.0 310 Example 16 4.5 7.0 340 Example 17 4.5 47.0 358 Example 18 4.1 45.8 246 Comparative Example 7 5.1 30.0 148 Comparative Example 8 5.3 32.0 168

As shown in Table 2, the compound of Formula 1 of the present invention exhibited superior properties compared to Comparative Examples 7 and 8 in Examples 15 to 18 in which the compound of Formula 1 was used as a dopant for the emission layer of an organic light-emitting device. Specifically, from Table 2, the compound containing the heteroarylene linker of Formula 1 of the present invention has excellent effects in terms of voltage, efficiency and life compared to the compound not containing the heteroarylene linker of Comparative Compounds 1 to 6 Confirmed. In addition, comparing Tables 1 and 2, compared to Examples 1, 3, 6, and 14 in which the compound of Formula 1 was used alone as the dopant material of the emission layer of the organic light-emitting device, Examples 15 to 18 using a fluorescent dopant at the same time. It was confirmed that the efficiency and lifetime of the organic light emitting device were improved. On the other hand, when comparing the results of Comparative Examples 1 and 3 with Comparative Examples 7 and 8, it could not be confirmed that the efficiency and lifespan were improved in Comparative Examples 7 and 8 despite the simultaneous use of the fluorescent dopant.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: electron injection layer

Claims (8)

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

In Formula 1,
L is a substituted or unsubstituted N-containing monocyclic heteroarylene group,
A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
X ₁ to X ₃ are the same as or different from each other, and each independently N or CR,
At least one of X ₁ to X ₃ is N,
R is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or , Can be combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted hetero ring,
a and b are each an integer of 0 to 4,
When a or b is plural, the substituents in parentheses are the same as or different from each other. The compound of claim 1, wherein L is an N-containing monocyclic heteroarylene group, and is substituted or unsubstituted with any one or more selected from deuterium, nitrile group, haloalkyl group, and alkyl group. The method according to claim 1, wherein A ₁ and A 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. compound. The compound of claim 1, wherein R ₁ and R ₂ are combined with an adjacent group to form a substituted heterocyclic group. The 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 contains the compound of any one of claims 1 to 5 Light-emitting element. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound as a dopant of the emission layer, and further includes an additional fluorescent dopant.

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