KR102390662B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Compound and organic light emitting device including 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 by reference.

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed 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, 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 the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

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

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

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 are 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, each independently N or CR,

At least one of X ₁ to X ₃ is N,

R is 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,

R ₁ and R ₂ are the same as or different from each other and are 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; , may combine with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocycle,

a and b are each an integer from 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 to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using the compound, high color purity and/or lifespan characteristics may be improved in the organic light emitting device.

In particular, the electron transport ability is excellent due to the triazine in the structure of the present invention. The electron transport ability is further improved by the nitrogen atom contained in the linker. An intra-charge-transfer state is formed by transferring a charge from the portion having the n-type property of the triazine-linker to the portion having the p-type property. When a material having these properties is used as a dopant in the light emitting layer of an organic light emitting device, it has remarkable effects on both hole transport and electron transport, thereby exhibiting low voltage, high efficiency, and long lifespan. In particular, the compound of the present invention increases the rate and speed at which excitons generated from triplets move to singlets by reverse intersystem transition (RISC), thereby reducing the time the excitons stay in the triplets, so the efficiency and lifespan of the organic light-emitting device This further increases the advantage.

1 and 2 show 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 Formula 1 above.

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

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

As used herein, 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 it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, 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 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 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 preferable that it has 1-10 carbon atoms. Specific examples include a methyl group; ethyl group; Profile 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 is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, 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; There is a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 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 ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine 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 a 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 is 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; vinyl dimethyl silyl group; propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; There is a phenylsilyl group, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, 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 preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms. Specifically, the monocyclic aryl group includes a phenyl group; biphenyl group; It may be a terphenyl group, and the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms, and more specifically, it is preferable 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, but is not limited thereto.

As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. 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.

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 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, that is, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S. The number of carbon atoms is not particularly limited, but preferably has 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; acrydyl group; pyridazinyl group; pyrazinyl group; quinolinyl group; quinazolinyl group; quinoxalinyl group; phthalazinyl group; pyrido pyrimidyl group; pyrido pyrazinyl group; pyrazino pyrazinyl group; isoquinolinyl group; indolyl group; carbazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiazolyl group; benzocarbazolyl group; benzothiophene group; dibenzothiophene group; benzofuranyl group; a phenanthroline group; isoxazolyl group; thiadiazolyl group; There is a phenothiazinyl group and a dibenzofuranyl group, but is 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 an exemplary embodiment of the present specification, X ₁ to X ₃ are N.

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

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

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

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

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

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

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

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

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

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

In an 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 substituted or unsubstituted with any one or more selected from a nitrile group, a haloalkyl group, and an alkyl group.

In an 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, and an alkyl group.

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

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

In an exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently represents 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 C 6 to C 30 aryl group, or a substituted or unsubstituted C 3 to C 30 hetero It is an aryl group.

In an exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently represents a substituted or unsubstituted C 6 to C 30 aryl group.

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

In an 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 an 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 an unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

In an 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 am.

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

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

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

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

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

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

In an 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 unsubstituted 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 an 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 an 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 C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted heterocycle.

In an 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, combined with an adjacent group to form a heterocycle,

the aryl group; Or a heteroaryl group, or a heterocyclic ring formed by bonding with an adjacent group is 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 from the group consisting of It is substituted or unsubstituted with one or more selected substituents.

In an 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 substituted or unsubstituted with an aryl group, or combined with an adjacent group to form a substituted or unsubstituted heterocycle.

In an 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 C 3 to C 30 heteroaryl group unsubstituted or substituted with an aryl group, or combined with an adjacent group to form a heterocyclic ring substituted or unsubstituted with an aryl group.

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

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

In an 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, a fluorene group, a carbazole group, a benzocarbazole group, a dibenzofuran group, or a 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 substituted or unsubstituted 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 an 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, a fluorene group, a carbazole group, a benzocarbazole group, a dibenzofuran group, or a 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 an 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 dibenzothiophene gi,

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

In an 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 an 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 an 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 an 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 an 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 having 6 to 30 carbon atoms, or a benzocarbazole group unsubstituted or substituted by an aryl group having 6 to 30 carbon atoms.

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

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

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

In an 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.

In an 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 having 6 to 30 carbon atoms.

In an 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 having 6 to 30 carbon atoms.

In an 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 phenyl group.

In an exemplary embodiment of the present specification, the 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 substitutable hydrogen is replaced with deuterium.

In an 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, this means that other components may be further included rather than excluding other components unless otherwise stated.

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

The organic light emitting device of the present invention includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more 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, but 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 stacked in this order is exemplified. The compound of the present invention is preferably contained in the light emitting layer (3).

In an exemplary embodiment of the present invention, the light emitting layer includes the compound.

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

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

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

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

[Formula A]

In the formula A,

XX1 and XX2 are the same as or different from each other and are 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 may be combined with a group to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocycle,

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

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

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

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

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

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

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

In one 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 pyreng

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

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

In an 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, the hole transport layer, or the hole injection and transport layer may include the compound of Formula 1 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 may contain the compound of Formula 1 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 using 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 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, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. can be deposited to form an anode, and 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 is formed thereon, and then a material that can be used as a cathode thereon It can be prepared by vapor deposition. 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 generally preferred 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, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto.

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

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

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

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining 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 compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the dopant material include an aromatic compound, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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. As the styrylamine compound, a substituted or unsubstituted A compound in which at least one arylvinyl group is substituted with an arylamine, one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is 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 them to the light emitting layer. Do. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

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 with respect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals 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-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the 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 complex, and the like, but is not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side 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 for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

A method of preparing the compound of Formula 1 and manufacturing an organic light emitting device using the same will be described in detail in Examples below. However, the following examples are intended to illustrate 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 by those skilled in the art by appropriately selecting known starting materials for the type and number of substituents. As 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.

By appropriately combining the preparation formulas described in the Examples of the present specification and the intermediates 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 refluxed under the conditions of dissolving 1,4-dioxane 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 refluxed for 12 hours in a condition of dissolving tetrahydrofuran and water under reflux reaction for intermediate b (3.60 g, yield: 90%) was synthesized.

Synthesis Example 1. (Synthesis of Compound 1)

Intermediate b (1.31 g, 2.83 mmol), 12-phenyl-5,12-dihydroindole [3,2-a] carbazole (0.94 g, 2.83 mmol) and cesium carbonate (2.80 g, 8.49 mmol) were dissolved in 10 ml of The mixture added to dimethylformamide was refluxed for 3 hours. After completion of the reaction, extraction with dichloromethane, drying over MgSO ₄ , and evaporating the solvent was purified by column chromatography (dichloromethane/hexane (1:1)) to prepare compound 1 (1.80 g, yield: 82%) did

MS (APCI) m/z 777.36 [(M+H) ⁺ ].

Synthesis Example 2. (Synthesis of Compound 2)

11-(phenyl-d5)-11,12-dihydroindolo instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol) in Synthesis Example 1 Compound 2 (1.52 g, 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 (1.31 g, 2.83 mmol).

MS (APCI) m/z 670.26 [(M+H) ⁺ ].

Synthesis Example 3. (Synthesis of Compound 3)

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

MS (APCI) m/z 665.23 [(M+H) ⁺ ].

Synthesis Example 4. (Synthesis of Compound 4)

11-(phenyl-d5)-11,12-dihydroindolo instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol) in Synthesis Example 1 Compound 4 (1.32 g, 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 (1.54 g, yield: 68%) was prepared in the same manner except for using carbazole and using intermediate f instead of intermediate b (1.31 g, 2.83 mmol).

MS (APCI) m/z 799.34 [(M+H) ⁺ ].

Synthesis Example 6. (Synthesis of Compound 6)

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

MS (APCI) m/z 789.29 [(M+H) ⁺ ].

Synthesis Example 7. (Synthesis of Compound 7)

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

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 (1.56 g, yield: 64%) was prepared in the same manner except for using carbazole and using intermediate i instead of intermediate b (1.31 g, 2.83 mmol).

MS (APCI) m/z 862.30 [(M+H) ⁺ ]

Synthesis Example 9. (Synthesis of Compound 9)

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

MS (APCI) m/z 803.27 [(M+H) ⁺ ]

Synthesis Example 10. (Synthesis of Compound 10)

11-(phenyl-d5)-11,12-dihydroindolo instead of 12-phenyl-5,12-dihydroindolo[3,2-a]carbazole (0.94g, 2.83mmol) in Synthesis Example 1 Compound 10 (1.17 g, yield: 56%) was prepared in the same manner except that [2,3-a] carbazole was used, and intermediate k was used 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 (1.41 g, yield: 62%) was prepared in the same manner except that carbazole was used and intermediate l was used instead of intermediate b (1.31 g, 2.83 mmol).

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 (1.55 g, yield: 68%) was prepared in the same manner except that carbazole was used and intermediate m was used instead of intermediate b (1.31 g, 2.83 mmol).

MS (APCI) m/z 806.32 [(M+H) ⁺ ]

Synthesis Example 13. (Synthesis of Compound 13)

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

MS (APCI) m/z 665.23 [(M+H) ⁺ ].

Synthesis Example 14. (Synthesis of Compound 14)

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

MS (APCI) m/z 777.98 [(M+H) ⁺ ].

Example 1

The light emitting area of ITO (indium tin oxide) glass was patterned to have a size of 3 mm × 3 mm, and then washed. After the substrate is mounted in a vacuum chamber, the base pressure is set to 1x10 ^-6 torr, and HT-1 is formed as a hole injection layer on the anode, ITO, to a thickness of 100 Å, but compound A-1 is used at a doping concentration of 25 wt%. doped. Then, as a hole transport layer, HT-1 was formed to a thickness of 600 Å, and 1,3-bis (N-carbazolyl) benzene (mCP) was formed to a thickness of 50 Å. did Next, as a light emitting layer, compound 1 of Synthesis Example 1 was used as a dopant in m-CBP as a host, and deposited so as to have a weight ratio of 8:2, and diphenyl [4- (triphenylsilyl) phenyl] phosphine as an 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 diode.

Example 2

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 2 was used instead of Compound 1.

Example 3

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 3 was used instead of Compound 1.

Example 4

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 4 was used instead of Compound 1.

Example 5

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 5 was used instead of Compound 1.

Example 6

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 6 was used instead of Compound 1.

Example 7

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 7 was used instead of Compound 1.

Example 8

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 8 was used instead of Compound 1.

Example 9

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 9 was used instead of Compound 1.

Example 10

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 10 was used instead of Compound 1.

Example 11

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 11 was used instead of Compound 1.

Example 12

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 12 was used instead of Compound 1.

Example 13

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 13 was used instead of Compound 1.

Example 14

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Compound 14 was used instead of Compound 1.

Comparative Example 1

Under the same process conditions as in Example 1, an organic light emitting diode was manufactured except that Comparative Compound 1 was used instead of Compound 1.

[Comparative compound 1]

Comparative Example 2

An organic light emitting diode was manufactured under the same process conditions as in Example 1, except that Comparative Compound 2 was used 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 except that Comparative Compound 3 was used instead of Compound 1.

[Comparative compound 3]

Comparative Example 4

Under the same process conditions as in Example 1, an organic light emitting diode was manufactured except that Comparative Compound 4 was used instead of Compound 1.

[Comparative compound 4]

Comparative Example 5

Under the same process conditions as in Example 1, an organic light emitting diode was manufactured except that Comparative Compound 5 was used instead of Compound 1.

[Comparative compound 5]

Comparative Example 6

Under the same process conditions as in Example 1, an organic light emitting diode was manufactured except that Comparative Compound 6 was used instead of Compound 1.

[Comparative compound 6]

By applying a current to the organic light emitting diodes prepared in Examples 1 to 14 and Comparative Examples 1 to 6, voltage, efficiency, and lifetime (T95) were measured, respectively, and the results are shown in Table 1 below. At this time, the voltage and the 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 nits decreases to 95%.

Voltage (V) (@10mA/cm ² ) Efficiency (cd/A) (@10mA/cm ² ) Lifetime (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 using the compound of Formula 1 of the present invention as a dopant for the emission layer of the organic light emitting diode were superior in low voltage, high efficiency, and long life compared to Comparative Examples 1 to 6. characteristics were shown.

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 containing no heteroarylene linker of Comparative Compounds 1 to 6 confirmed that.

Example 15

The light emitting area of ITO (indium tin oxide) glass was patterned to have a size of 3 mm × 3 mm, and then washed. After mounting the substrate in a vacuum chamber and making the base pressure 1x10 ^-6 torr, 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 wt% Doped with concentration. Then, as a hole transport layer, HT-1 was formed to a thickness of 600 Å, and 1,3-bis(N-carbazolyl)benzene (mCP) was formed to a thickness of 50 Å. Next, m-CBP, a host, as a light emitting layer, was deposited as a dopant, Compound 1, and a fluorescent dopant, Compound-D, in a weight ratio of 79:20:1, 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 diode.

[Compound-D]

Example 16

Under the same process conditions as in Example 15, an organic light emitting diode was manufactured except that Compound 3 was used instead of Compound 1.

Example 17

Under the same process conditions as in Example 15, an organic light emitting diode was manufactured except that Compound 6 was used instead of Compound 1.

Example 18

Under the same process conditions as in Example 15, an organic light emitting diode was manufactured except that Compound 14 was used instead of Compound 1.

Comparative Example 7

Under the same process conditions as in Example 15, an organic light emitting diode was manufactured except that Comparative Compound 1 was used instead of Compound 1.

Comparative Example 8

Under the same process conditions as in Example 15, an organic light emitting device was manufactured except that Comparative Compound 3 was used instead of Compound 1.

By applying a current to the organic light emitting diodes prepared in Examples 15 to 18 and Comparative Examples 7 and 8, voltage, efficiency, and lifetime (T95) were measured, respectively, and the results are shown in Table 2 below. At this time, the voltage and the 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 nits decreases to 95%.

Voltage (V)
(@10mA/cm ² ) Efficiency (cd/A) (@10mA/cm ² ) Lifetime (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, Examples 15 to 18, in which the compound of Formula 1 of the present invention was used as a dopant in the emission layer of an organic light emitting diode, showed superior properties compared to Comparative Examples 7 and 8. Specifically, from Table 2, the compound containing the heteroarylene linker of Formula 1 of the present invention has an excellent effect in terms of voltage, efficiency and lifespan compared to the compound containing no heteroarylene linker of Comparative Compounds 1 to 6 confirmed that. In addition, comparing Table 1 and Table 2, Examples 15 to 18 in which the fluorescent dopant was simultaneously used compared to Examples 1, 3, 6, and 14 in which the compound of Formula 1 was used alone as the dopant material of the light emitting layer of the organic light emitting device. It was confirmed that the efficiency and lifespan of the organic light emitting diode were improved. On the other hand, when comparing the results of Comparative Examples 1 and 3 and Comparative Examples 7 and 8, in Comparative Examples 7 and 8, although the fluorescent dopant was used at the same time, it could not be confirmed that the efficiency and lifespan were improved.

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)

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

In Formula 1,
L is an N-containing monocyclic heteroarylene group substituted with any one or more selected from a nitrile group, a haloalkyl group, and an alkyl group, and the N-containing monocyclic heteroarylene group may be unsubstituted or substituted with deuterium,
A ₁ and A ₂ are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms,
X ₁ to X ₃ are N,
R ₁ is an N-phenylbenzocarbazole group,
R ₂ is hydrogen or a phenyl group,
a and b are each an integer from 1 to 4,
When a is plural, the substituents in parentheses are the same as or different from each other. delete delete delete The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound of any one of claims 1 and 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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