KR20210110233A - Polycyclic aromatic compound and organoelectroluminescent device using the same - Google Patents

Abstract

The present invention relates to a polycyclic aromatic derivative compound that can be used in various organic layers in an organic light emitting device, and an organic light emitting device with high efficiency and long lifespan, which has remarkably improved luminous efficiency by including the same.

Description

Polycyclic aromatic compound and organic light emitting device using the same {Polycyclic aromatic compound and organoelectroluminescent device using the same}

The present invention relates to a polycyclic aromatic derivative compound and a high-efficiency, long-life organic light-emitting device with remarkably improved luminous efficiency using the same.

In an organic light emitting device, electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in a light emitting layer to form excitons, and the excitons release energy It is a self-luminous device that emits light while emitting light, and such an organic light-emitting device has a low driving voltage, high luminance, wide viewing angle, and fast response speed, and is in the spotlight as a next-generation light source because of its advantages that it can be applied to a full-color flat panel light emitting display. .

In order for such an organic light emitting device to exhibit the above characteristics, the structure of the organic layer in the device is optimized, and the material constituting each organic layer is a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an electron blocking material. It should be preceded by a stable and efficient material, but it is still necessary to develop a stable and efficient organic layer structure and each material for an organic light emitting device.

As such, the structure of the device capable of improving the light emitting characteristics of the organic light emitting device and the development of a new material supporting it are continuously required.

Accordingly, an object of the present invention is to provide an organic light emitting compound capable of implementing an organic light emitting device with high efficiency and long lifespan by being employed in the organic layer of the device, and an organic light emitting device including the same.

The present invention provides an organic light emitting compound represented by the following [Formula A-1] to [Formula A-2] in order to solve the above problems.

[Formula A-1] [Formula A-2]

In addition, the compound represented by the [Formula A-1] to [Formula A-2] according to the present invention is characterized in that it necessarily contains at least one of the following [Structural Formula Cy] and/or [Structural Formula Cy-Q3].

[Structural formula Cy] [Structural formula Cy-Q3]

More specific structures and definitions of each substituent of the [Formula A-1] to [Formula A-2], [Structural formula Cy] and [Structural formula Cy-Q3], and [Formula A-1] to [Formula A-2] ], the specific polycyclic aromatic compound according to the present invention embodied in ] will be described later.

In addition, the present invention includes a first electrode, a second electrode opposite to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is [Formula A-1] to [Formula A-1] A-2] provides an organic light emitting device comprising at least one specific polycyclic aromatic compound implemented as.

The polycyclic aromatic derivative compound according to the present invention can be employed in the organic layer in the device to realize a high efficiency and long life organic light emitting device.

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

The present invention is included in an organic light emitting device, and relates to a polycyclic aromatic derivative compound represented by the following [Formula A-1] to [Formula A-2], structurally including at least one cyclic ring in the following skeleton structure It is characterized in that, through this, it is possible to implement an organic light emitting device of high efficiency and, in particular, a long lifespan with significantly improved lifespan characteristics.

[Formula A-1] [Formula A-2]

The compound represented by [Formula A-1] to [Formula A-2] according to the present invention is characterized in that it necessarily includes at least one of the following [Structural Formula Cy] and/or [Structural Formula Cy-Q3].

[Structural formula Cy] [Structural formula Cy-Q3]

In the [Formula A-1] to [Formula A-2],

(i) X is B, P, P=O, P=S or Al, and according to a preferred embodiment of the present invention, may be B, and structurally high efficiency through a polycyclic aromatic derivative compound containing boron (B) And it is characterized in that it can implement a long-life organic light emitting device.

(ii) Y is NR ₁ , CR ₂ R ₃ , O, S, Se, SiR ₄ R ₅ and a single bond, and a plurality of Ys are the same as or different from each other.

(iii) Z is N or CR ₆ , where R ₆ may be the following [Structural Formula Cy-Q3] as described below, and a plurality of Zs are the same or different, and at least two of the plurality of Zs are CR _{In the} case of 6, two adjacent R ₆ may be bonded to the following [Structural Formula Cy].

(iv) Q ₁ and Q ₂ are the same as or different from each other, and are each selected from the following [Structural Formula 1] and [Structural Formula 2].

[Structural Formula 1] [Structural Formula 2]

In the [Structural Formula 1] to [Structural Formula 2],

Q ₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms.

A is N, CR ₇ or SiR ₈ , a plurality of A are the same as or different from each other and not connected to each other, V is NR ₉ , O, S or Se, and n is an integer from 1 to 10.

Here, two adjacent ones of A and V in [Structural Formula 1] may be bonded to the following [Structural Formula Cy], and two adjacent ones of V and R in [Structural Formula 2] may be bonded to the following [Structural Formula Cy] .

_{In addition, the atoms constituting the Q 3} ring in [Structural Formula 2], that is, two adjacent atoms among C, N, or Si may be bonded to the following [Structural Formula Cy].

[Structural formula Cy]

In the [Structural Formula Cy],

L is a substituted or unsubstituted aliphatic chain or a heteroaliphatic chain.

W is selected from -CR ₁₄ R ₁₅ -, _{-CR 16} =, -C≡, -SiR ₁₇ R ₁₈ -, -SiR ₁₉ = and -Si≡, a plurality of Ws are the same or different from each other, and W is L It is connected to adjacent atoms of by saturated or unsaturated bonds.

Adjacent substituents in [Structural Formula Cy] may be combined with each other or W to further form an alicyclic or aromatic monocyclic or polycyclic ring.

(v) the R, R ₁ to R ₉ and R ₁₄ to R ₁₉ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to 50 aryl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 2 to C 50 heteroaryl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkylamine having 1 to 30 carbon atoms group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, As any one selected from a halogen group and the following [Structural formula Cy-Q3], wherein R, R ₁ to R ₉ and R ₁₄ to R ₁₉ may be each of the following [Structural formula Cy-Q3].

[Structural formula Cy-Q3]

In the [Structural Formula Cy-Q3],

L, W and Q ₃ are the same as the definitions in [Structural Formula 2] and [Structural Formula Cy], respectively, and when R, R ₁ to R ₉ and R ₁₄ to R ₁₉ are each [Structural Formula Cy-Q3], L , W and Q ₃ means to be bound to any one of.

R' is hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyltioxy group having 1 to 30 carbon atoms, A substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C1-C30 alkylamine group It is selected from an alkylsilyl group of 30, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, and m is an integer of 1 to 10.

Wherein R, R', R ₁ to R ₉ and R ₁₄ to R ₁₉ may be bonded to each other or connected to an adjacent substituent to form an alicyclic, aromatic monocyclic or polycyclic ring, and the formed alicyclic, aromatic A carbon atom of the monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, O, Se, Si, B, P and Al.

In addition, each of R ₂ and R ₃ , R ₄ and R ₅ may be connected to each other to form an alicyclic, aromatic monocyclic or polycyclic ring.

As such, the compounds represented by [Formula A-1] to [Formula A-2] according to the present invention are Q ₁ and Q _{2 defined by [Structural Formula 1] or [Structural Formula 2] combined with [Structural Formula Cy]} , when a plurality of Z is bonded to [Structural Formula Cy], R, R ₁ to R ₉ and R ₁₄ to R ₁₉ are [Structural Formula Cy] through [Structural Formula Cy] and/or It is characterized in that it necessarily contains at least one [Structural Formula Cy-Q3].

According to an embodiment of the present invention, Q ₃ is a 5-membered ring or a 6-membered monocyclic ring, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms composed of 2 to 5 polycyclic rings, or a substituted or unsubstituted It may be an aromatic heterocyclic ring having 2 to 50 carbon atoms.

According to one embodiment of the present invention, when A in [Structural Formula 1] is CR _{7 , R 7} is connected to each other and is represented by a ring represented by [Structural Formula Cy].

According to an embodiment of the present invention, in the [Structural Formula Cy] and [Structural Formula Cy-Q3], W is -CR ₁₄ R ₁₅ - _{, -CR 16} =, -C≡, -SiR ₁₇ R ₁₈ -, -SiR ₁₉ = and -Si≡, in the case of any one selected from, R ₁₄ to R ₁₉ are a substituted or unsubstituted C 1 to C 30 alkyl group, substituted or unsubstituted C 6 to C 50 aryl except for hydrogen and deuterium group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C6 A 30 aryloxy group, a substituted or unsubstituted C 1 to C 30 alkylthioxy group, a substituted or unsubstituted C 5 to C 30 arylthioxy group, a substituted or unsubstituted C 1 to C 30 alkylamine group, substituted or Select from an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group do.

As such, [Formula A-1] to [Formula A-2] according to the present invention are organic by necessarily including at least one cyclic ring structure having a characteristic structure while having various skeleton structures according to the definition of the skeleton structure and substituents. Various organic layers of the light emitting device satisfy the desired conditions, thereby realizing the organic light emitting device with high efficiency and long life.

Meanwhile, in the present invention, the term 'substituted or unsubstituted' means that each of the substituents defined above is deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, cyclo having 3 to 24 carbon atoms. Alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C1-C24 heterocycloalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 aryl It is substituted with 1 or 2 or more substituents selected from the group consisting of an amino group, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms, It means that two or more of the substituents are substituted with a connected substituent, or do not have any substituents.

In addition, the carbon number range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 10 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 30 carbon atoms', etc., considers the portion in which the substituent is substituted. It refers to the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted. For example, a phenyl group substituted with a butyl group at the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

In addition, in the present invention, the meaning that adjacent groups are bonded to each other to form a ring means that adjacent groups can be bonded to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and 'adjacent substituents' The substituent may refer to a substituent substituted on an atom directly connected to the substituted atom, a substituent positioned closest to the steric structure to the substituent, or another substituent substituted with the atom in which the substituent is substituted. 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 substituents'.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. 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-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, 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-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present invention, the alkenyl group includes a straight or branched chain, and may be further substituted by other substituents, specifically, a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-bute Nyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group , 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl -1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present invention, the alkynyl group also includes a straight or branched chain, and may be further substituted by other substituents, and may include ethynyl, 2-propynyl, and the like, but is limited thereto. it doesn't happen

In the present invention, the cycloalkyl group includes a monocyclic or polycyclic ring, and may be further substituted by another substituent, and the polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group, and the other ring group is a cycloalkyl group. may be, but may be other types of ring groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present invention, the heterocycloalkyl group includes a heteroatom such as O, S, Se, N or Si, and also includes monocyclic or polycyclic, and may be further substituted by other substituents, and polycyclic means heterocyclo The alkyl group refers to a group directly connected or condensed with another ring group, and the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like.

In the present invention, the aryl group may be monocyclic or polycyclic, and examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group and an anthracenyl group. , phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention is limited only to these examples it's not going to be

In the present invention, the heteroaryl group is a heterocyclic group containing heteroatoms, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, Bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyrido Pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzo Furanyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc., but are not limited thereto .

In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, but is not limited thereto.

In the present invention, the silyl group refers to a silyl group substituted with alkyl or a silyl group substituted with aryl, and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxyphenylsilyl. , diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like.

In the present invention, the _{amine group may be -NH 2} , an alkylamine group, an arylamine group, etc., the arylamine group means an amine substituted with an aryl, the alkylamine group means an amine substituted with an alkyl, and an arylamine group Examples of these include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the aryl group in the arylamine group may be a monocyclic aryl group, and It may be a cyclic aryl group, and 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. In addition, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present invention, the aryl group in the aryloxy group and the arylthioxy group is the same as the above-described aryl group, and specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenane and a toryloxy group, a 9-phenanthryloxy group, and the like, and the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

More specifically, the polycyclic aromatic derivative compound represented by [Formula A-1] to [Formula A-2] according to the present invention may be any one selected from the following [Compound 1] to [Compound 218], through which The substituent may be clearly identified, but the range of [Formula A-1] to [Formula A-2] according to the present invention is not limited thereby.

As can be seen in the above specific compound, a cyclic ring structure having a characteristic structure while forming a polycyclic aromatic skeleton structure including B, P, P=O, P=S, Al, etc. is necessarily included, and a substituent can be introduced to synthesize an organic light emitting material having intrinsic properties of the skeleton structure and substituents, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer used in the manufacture of an organic light emitting device , a material satisfying the conditions required by each organic layer can be prepared by introducing a substituent used for the , hole blocking layer material, etc.

In addition, another aspect of the present invention relates to an organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the [Formula A- 1] to [Formula A-2] may include at least one organic light emitting compound according to the present invention.

That is, the organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween, and according to the present invention [Formula A-1] to [Formula A-2], except that the organic light emitting compound of the device is used for the organic layer of the device, it can be manufactured using a conventional device manufacturing method and material.

The organic layer of the organic light emitting device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers, and the preferred organic layer structure of the organic light emitting device according to the present invention will be described in more detail in the following Examples.

Hereinafter, an embodiment of the organic light emitting device according to the present invention will be described in more detail.

The organic light emitting device according to the present invention includes an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode, and if necessary, may further include a hole injection layer between the anode and the hole transport layer, and also between the electron transport layer and the cathode It may further include an injection layer, in addition to that, it is also possible to further form an intermediate layer of one or two layers, a hole blocking layer or an electron blocking layer may be further formed, and an organic layer having various functions according to the characteristics of the device. may further include.

First, the organic light emitting device according to the present invention is characterized in that it contains an anthracene derivative represented by the following [Formula C] as a host compound in the light emitting layer.

[Formula C]

In the [Formula C],

R ₂₁ to R ₂₈ are the same as or different from each other, and are the same as defined for R in [Formula A-1] to [Formula A-2].

Ar ₉ and Ar ₁₀ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted Unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms Oxy group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted It may be any one selected from an arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms.

L ₁₃ is a single bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, preferably a single bond, or It may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, k is an integer of 1 to 3, but when k is 2 or more, each L ₁₃ is the same as or different from each other.

In addition, Ar ₉ of the [Formula C] is characterized in that it is a substituent represented by the following [Formula C-1].

[Formula C-1]

In the [Formula C],

R ₃₁ to R ₃₅ are the same or different, and are the same as defined for R in [Formula A-1] to [Formula A-2], and combine with neighboring substituents to form a saturated or unsaturated ring have.

The [Formula C] employed in the organic light emitting device according to the present invention may be any one specifically selected from the following [Formula C1] to [Formula C57].

In addition, the organic light emitting device according to the present invention may further include a hole transport layer, an electron blocking layer, etc., respectively, it is characterized in that the compound represented by the following [Formula D] is included in the hole transport layer, the electron blocking layer, etc., respectively.

[Formula D]

In the above [Formula D],

R ₄₁ to R ₄₃ are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C number A 7 to 50 arylalkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, and a halogen group any one selected from

L ₃₁ to L ₃₄ are the same as or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

Ar ₃₁ to Ar ₃₄ are the same as or different from each other, and are each independently any one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

n is an integer of 0 to 4, when n is 2 or more, _{each aromatic ring including R 43} is the same or different from each other, and m ₁ to m ₃ are an integer of 0 to 4, and when they are each 2 or more each R ₄₁ , R ₄₂ , or R ₄₃ is the same as or different from each other.

A carbon atom of the aromatic ring to which R _{41 to R 43} is not bonded is bonded to hydrogen or deuterium.

In addition, _{at least one of Ar 31} to Ar ₃₄ is a substituent represented by the following [Formula E].

[Formula E]

In the [Formula E],

R ₅₁ to R ₅₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C number 2 to 30 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C5 to C30 cycloalkenyl group, substituted or unsubstituted A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C6 to C30 arylox Group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C5 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C1C group Any one selected from an arylamine group of 5 to 30, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group , they may each be linked to each other to form a ring.

Y is a carbon atom or a nitrogen atom, and Z is a carbon atom, an oxygen atom, a sulfur atom or a nitrogen atom.

Ar ₃₅ to Ar ₃₇ are the same as or different from each other, and are each independently any one selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms.

When Z is an oxygen atom or a sulfur atom, Ar ₃₇ is not present _{, when Y and Z are nitrogen atoms, only one of Ar 35} , Ar ₃₆ and Ar ₃₇ is present, and when Y is a nitrogen atom and Z is a carbon atom, Ar ₃₆ is does not exist.

However, one of R ₅₁ to R ₅₄ and Ar ₃₅ to Ar ₃₇ is a single bond connected to one of the linking groups _{L 31} to L ₃₄ in [Formula D].

The [Formula D] employed in the organic light emitting device according to the present invention may be any one specifically selected from the following [Formula D1] to [Formula D79].

In addition, the [Formula D] employed in the organic light emitting device according to the present invention may be any one specifically selected from the following [Formula D101] to [Formula D145].

In addition, the organic light emitting device according to the present invention may further include a hole transport layer, an electron blocking layer, etc., respectively, it is characterized in that the compound represented by the following [Formula F] is included in the hole transport layer, the electron blocking layer, etc., respectively.

[Formula F]

In the [Formula F],

R ₆₁ to R ₆₃ are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C number 2 to 30 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C5 to C30 cycloalkenyl group, substituted or unsubstituted A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C6 to C30 arylox Group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C6 to C30 group A 6 to 30 arylamine group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, a substituted or unsubstituted C1 to C30 alkylgermanium group, Any one selected from a substituted or unsubstituted C1-C30 arylgermanium group, a cyano group, a nitro group, and a halogen group.

Ar ₅₁ to Ar ₅₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted C 6 to C 40 aryl group, or a substituted or unsubstituted C 2 to C 30 heteroaryl group.

The [Formula F] employed in the organic light emitting device according to the present invention may be any one specifically selected from the following [Formula F1] to [Formula F33].

Meanwhile, a detailed structure of an organic light emitting diode according to an embodiment of the present invention, a manufacturing method thereof, and each organic layer material will be described as follows.

First, an anode is formed by coating a material for an anode electrode on a substrate. Here, as the substrate, a substrate used in a conventional organic light emitting device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handling and water resistance is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on the anode electrode, and then a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer. .

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, and as a specific example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] can be used.

In addition, the hole transport layer material is also not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1- Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (?-NPD), etc. can be used.

Then, a hole auxiliary layer and a light emitting layer are sequentially stacked on the hole transport layer, and a hole blocking layer is selectively deposited on the light emitting layer by a vacuum deposition method or a spin coating method to form a thin film. The hole blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifetime and efficiency of the device are reduced when holes are introduced into the cathode through the organic light emitting layer. . In this case, the hole blocking material used is not particularly limited, but has an electron transport ability and has an ionization potential higher than that of a light emitting compound, and typically BAlq, BCP, TPBI, etc. may be used.

Materials used for the hole blocking layer include, but are not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and the like.

After depositing an electron transport layer on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer is formed, and a cathode forming metal is vacuum thermally deposited on the electron injection layer to form a cathode electrode. An organic light emitting diode according to an embodiment is completed.

Here, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

The electron transport layer material serves to stably transport electrons injected from the cathode, and a known electron transport material may be used. Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10- Materials such as olate: Bebq2), ADN, and oxadiazole derivatives PBD, BMD, BND, etc. may be used.

In addition, each of the organic layers may be formed by a monomolecular deposition method or a solution process, wherein the deposition method evaporates a material used as a material for forming each layer through heating in a vacuum or low pressure state. It refers to a method of forming a thin film, and the solution process mixes a material used as a material for forming each layer with a solvent, and uses it inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating It refers to a method of forming a thin film through a method such as, for example.

In addition, the organic light emitting diode according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a device for flat panel lighting of a single color or a white color, and a device for a flexible lighting device of a single color or a white color.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereby.

Synthesis example 1. [Compound 28] of synthesis

(1) [Intermediate A- 1] of synthesis

[A-1a] [A-1]

[Intermediate A-1] was obtained from [Intermediate A-1a] by using the same method presented in the synthesis method of the patent document (Chinese Patent Publication No. CN110551154). (Yield 65.3%)

MS (ESI) calcd for Chemical Formula: C ₁₂ H ₄ D ₅ BrCl (Pos)271.99, found 271.9

(2) [Intermediate A- 2] of synthesis

[A-2a] [A-2]

[Intermediate A-2] was obtained from [Intermediate A-2a] using the same method presented in the synthesis method of the patent document (Chinese Patent Publication No. CN110551154) except that hexachloroethane was used instead of iodine. (yield 73.6%)

MS (ESI) calcd for Chemical Formula: C ₁₂ H ₃ D ₅ BrCl ₂ (Pos)305.95, found 305.9

(3) [Intermediate A- 3] of synthesis

[A-3a] [A-3b] [A-3]

[Intermediate A-3] was obtained from [Intermediate A-3b] obtained through [Intermediate A-3a] using the same method presented in the synthesis method of the patent document (US Patent Publication No. US2020/172558). (yield 90.1%)

MS (ESI) calcd for Chemical Formula: C ₃₄ H ₂₉ D ₅ Cl ₂ NS (Pos)305.95, found 305.9

(4) [Intermediate A- 4] of synthesis

[A-4a] [A-4b] [A-4]

[Intermediate A-4 from [Intermediate A-4a] and [Intermediate A-4b] using the same method presented in the synthesis method of published literature (Tetrahedron, 2014, vol. 70, # 32, p. 4754 - 4759). ] was obtained. (Yield 83.1%)

MS (ESI) calcd for Chemical Formula: C ₂₆ H ₃₆ N (Pos)362.29, found 362.2

(5) [Intermediate A- 5] of synthesis

[A-3] [A-4] [A-5]

[Intermediate A-3], [Intermediate A-4] (1 eq), Fu catalyst (0.02 eq), sodium tert-butoxide (2 eq), toluene (10 mL/g) were added to the reactor, and then 6 hours while stirring at reflux. After cooling to room temperature, water and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. It was purified by silica gel chromatography to obtain [Intermediate A-5]. (Yield 87.6%)

MS (ESI) calcd for Chemical Formula: C ₆₀ H ₆₃ D ₅ ClN ₂ S (Pos)888.51, found 888.5

(6) [Compound 28] of synthesis

[A-5] [28]

After [Intermediate A-5] and tertiary butylbenzene (10 mL/g) were added to the reactor, a 1.7 M tertiary butyllithium pentane solution (3 eq) was added dropwise at -78 °C. After the temperature was raised to 60 °C, the mixture was stirred for 2 hours, and then nitrogen was blown at 60 °C to completely remove pentane. After cooling to -78 °C, boron tribromide (2 eq) was added dropwise. After raising the temperature to room temperature, stirring for 2 hours, and then cooling to 0 ℃, N,N- diisopropylethylamine (2 eq) was added dropwise. After raising the temperature to 120°C, the mixture was stirred for 12 hours. After cooling to room temperature, 10% sodium acetate aqueous solution and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. Purification by silica gel chromatography gave [Compound 28]. (yield 15.6%)

MS (ESI) calcd for Chemical Formula: C ₆₀ H ₆₁ D ₅ BN ₂ S (Pos)862.54, found 862.5

Synthesis example 2. [Compound 29] of synthesis

(1) [Intermediate B- 1] of synthesis

[B-1a] [B-1b] [B-1c] [B-1]

[Intermediate B-1d] was obtained from [Intermediate B-1c] obtained through [Intermediate B-1a] and [Intermediate B-1b] using the same method as for the synthesis of [Intermediate A-3]. (yield 91.3%)

MS (ESI) calcd for Chemical Formula: C ₃₇ H ₃₈ Cl ₂ NS (Pos)598.21, found 598.2

(2) Synthesis of [Intermediate B-2]

[B-2a] [B-2b] [B-2]

[Compound B-2] was obtained from [Intermediate B-2b] obtained through [Intermediate B-2a] using the same method presented in the synthesis method of the patent document (US Patent Publication No. US2020/172558). (Yield 83.8%)

MS (ESI) calcd for Chemical Formula: C ₃₆ H ₄₅ N ₂ (Pos)505.36, found 505.3

(3) [Compound 29] of synthesis

[B-1] [B-2] [B-3] [29]

[Compound 29] was obtained from [Intermediate B-3] obtained through [Intermediate B-1] and [Intermediate B-2] by using the same method as in Synthesis Example 1 above. (Yield 13.3%)

MS (ESI) calcd for Chemical Formula: C ₇₃ H ₇₉ BN ₃ S (Pos)1040.61, found 1040.6

Synthesis example 3. [Compound 30] of synthesis

[C-1] [C-2] [C-3] [30]

Using the same method as the synthesis method of Synthesis Example 1, [Compound 30] was obtained from [Intermediate C-3] obtained through [Intermediate C-2]. (yield 14.9%)

MS (ESI) calcd for Chemical Formula: C ₇₇ H ₈₇ BN ₃ S (Pos)1096.67, found 1096.6

Synthesis example 4. [Compound 31] of synthesis

(1) [Intermediate D- 1] of synthesis

[D-1a] [D-1b] [D-1]

[Intermediate D-1] was obtained from [Intermediate D-1b] obtained through [Intermediate D-1a] using the same method as for the synthesis of [Intermediate A-3]. (yield 84.5%)

MS (ESI) calcd for Chemical Formula: C ₃₁ H ₃₄ ClFNS (Pos)506.21, found 506.2

(2) [Intermediate D- 2] of synthesis

[D-1] [D-2a] [D-2]

[Intermediate D-1], [Intermediate D-2a] (1 eq), cesium carbonate (2 eq), and DMF (10 mL/g) were added to the reactor and stirred under reflux for 15 hours. After cooling to room temperature, water and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. It was purified by silica gel chromatography to obtain [Intermediate D-2]. (Yield 58.6%)

MS (ESI) calcd for Chemical Formula: C ₄₁ H ₄₇ ClNOS (Pos)636.31, found 636.3

(3) [Compound 31] of synthesis

[D-2] [31]

[Compound 31] was obtained from [Intermediate D-2] using the same method as for the synthesis of [Intermediate A-3]. (yield 10.2%)

MS (ESI) calcd for Chemical Formula: C ₄₁ H ₄₅ BNOS (Pos)610.33, found 610.3

Synthesis example 5. [Compound 32] of synthesis

(1) [Intermediate E- 1] of synthesis

[E-1a] [E-1b] [E-1c] [E-1]

[Intermediate E-1] was obtained from [Intermediate E-1c] obtained through [Intermediate E-1a] and [Intermediate E-1b] by using the same method as for the synthesis of [Intermediate A-3]. (yield 93.1%)

MS (ESI) calcd for Chemical Formula: C ₃₁ H ₃₄ Cl ₂ NO ₂ (Pos)636.31, found 636.3

(2) [Intermediate E- 2] of synthesis

[E-2a] [E-2b] [E-2]

[Intermediate E-2] was obtained from [Intermediate E-2b] obtained through [Intermediate E-2a] by using the same method as for the synthesis of [Intermediate B-2]. (Yield 87.4%)

MS (ESI) calcd for Chemical Formula: C ₃₈ H ₃₃ N ₂ O (Pos)533.26, found 533.2

(3) [Compound 32] of synthesis

[E-1] [E-2] [E-3] [32]

Using the same method as in Synthesis Example 1, [Compound 32] was obtained from [Intermediate E-3] obtained through [Intermediate E-1] and [Intermediate E-2]. (Yield 7.4%)

MS (ESI) calcd for Chemical Formula: C ₆₉ H ₆₃ BN ₃ O ₃ (Pos)992.50, found 992.5

Example 1 to 15: manufacture of organic light emitting device

The light emitting area of the ITO glass was patterned to have a size of 2 mm × 2 mm and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1 × 10 ^-7 torr, and then DNTPD (700 Å) and [Formula G] (250 Å) were formed on the ITO in this order. [Formula E-1] and [Formula E-2] as the host and dopant of the light emitting layer, after mixing the compounds shown in [Table 1] in a weight ratio (98:2) to form a film (250 Å), and then [Formula E-1] and [Formula E-2] An organic light emitting device was prepared by forming a film in the order of 300 Å and [Formula E-1] as an electron injection layer in a 1:1 ratio of 5 Å and Al (1000 Å). The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[DNTPD] [Formula G]

[Formula E-1] [Formula E-2]

comparative example 1 to 3

In the device structure of the above example, an organic light emitting device was prepared in the same manner except that the host compound and dopant compound described in Comparative Examples 1 to 3 of Table 1 were used instead of the compound according to the present invention in the light emitting layer. The luminescence characteristics were measured at 0.4 mA. The structures of BH1, BH2, BD1, and BD2 used in Comparative Examples 1 to 3 are as follows.

[BH1] [BH2]

[BD1] [BD2]

For the organic light emitting devices manufactured according to Examples 1 to 15 and Comparative Examples 1 to 3, voltage, external quantum efficiency, and lifetime were measured, and the results are shown in Table 1 below.

host dopant Voltage (V) External quantum efficiency (%) Lifetime (LT97) Example 1 BH1 compound 28 3.5 9.48 214 Example 2 BH1 compound 29 3.5 10.45 235 Example 3 BH1 compound 30 3.5 10.49 242 Example 4 BH1 compound 31 3.5 8.66 190 Example 5 BH1 compound 32 3.5 12.77 233 Example 6 BH1 compound 33 3.5 9.24 205 Example 7 BH1 compound 34 3.5 9.21 257 Example 8 BH1 compound 35 3.5 9.58 225 Example 9 BH1 compound 36 3.5 9.15 196 Example 10 BH1 compound 40 3.5 10.94 230 Example 11 BH1 compound 97 3.5 9.55 214 Example 12 BH1 compound 98 3.5 9.26 204 Example 13 BH1 compound 130 3.5 9.67 208 Example 14 BH1 compound 131 3.5 11.01 247 Example 15 BH1 compound 132 3.5 9.77 208 Comparative Example 1 BH1 BD1 3.5 7.81 125 Comparative Example 2 BH1 BD2 3.5 8.03 128 Comparative Example 3 BH2 BD1 3.8 6.84 61

As can be seen in [Table 1], the organic light emitting device employing the compound according to the present invention as a dopant material in the light emitting layer is a device employing a compound that contrasts with the characteristic structure of the compound according to the present invention (comparison Compared to Examples 1 to 3), it has excellent light emitting characteristics such as significantly improved lifespan characteristics and external quantum efficiency.

Claims (18)

A compound represented by any one of the following [Formula A-1] to [Formula A-2], and comprising at least one structure represented by the following [Structural Formula Cy] and [Structural Formula Cy-Q3]:
[Formula A-1] [Formula A-2]

[Structural formula Cy] [Structural formula Cy-Q3]

In the [Formula A-1] to [Formula A-2],
(i) X is B, P, P=O, P=S or Al;
(ii) Y is NR ₁ , CR ₂ R ₃ , O, S, Se, SiR ₄ R ₅ And any one selected from a single bond (a plurality of Y is the same or different from each other),
(iii) Z is N or CR ₆ (a plurality of Zs are the same or different), and when two or more of the plurality of Zs are CR ₆ , two adjacent R ₆ may be bonded to the following [Structural Formula Cy], ,
(iv) Q ₁ and Q ₂ are the same as or different from each other, and are each selected from the following [Structural Formula 1] and [Structural Formula 2],
[Structural Formula 1] [Structural Formula 2]

In the [Structural Formula 1] to [Structural Formula 2],
Q ₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms,
A is N, CR ₇ or SiR ₈ ,
V is NR ₉ , O, S or Se,
n is an integer from 1 to 10,
Two adjacent ones of A and V in [Structural Formula 1] may be combined with the following [Structural Formula Cy],
In [Structural Formula 2], two adjacent V and R may be combined with the following [Structural Formula Cy],
_{Among the atoms constituting the Q 3} ring in [Structural Formula 2], two adjacent atoms may be bonded to the following [Structural Formula Cy],
[Structural formula Cy]

In the [Structural Formula Cy],
L is a substituted or unsubstituted aliphatic chain or heteroaliphatic chain,
W is selected from -CR ₁₄ R ₁₅ -, _{-CR 16} =, -C≡, -SiR ₁₇ R ₁₈ -, -SiR ₁₉ = and -Si≡ (a plurality of Ws are the same or different from each other),
W is connected to adjacent atoms of L by a saturated bond or an unsaturated bond,
Adjacent substituents in [Structural Formula Cy] may be combined with each other or W to further form an alicyclic or aromatic monocyclic or polycyclic ring,
(v) the R, R ₁ to R ₉ and R ₁₄ to R ₁₉ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to 50 aryl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 2 to C 50 heteroaryl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkylamine having 1 to 30 carbon atoms group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, Any one selected from a halogen group and the following [Structural Formula Cy-Q3],
[Structural formula Cy-Q3]

In the [Structural Formula Cy-Q3],
L, W and Q ₃ are each the same as the definitions in [Structural Formula 2] and [Structural Formula Cy], and when R and R ₁ to R ₂₇ are each [Structural Formula Cy-Q3], of L, W and Q ₃ bound to any one
R' is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyltioxy group having 1 to 30 carbon atoms, A substituted or unsubstituted C5 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C5 to C30 arylamine group, a substituted or unsubstituted C1 to C1 It is selected from an alkylsilyl group of 30, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group,
m is an integer from 1 to 10,
Wherein R, R', R ₁ to R ₉ and R ₁₄ to R ₁₉ may be bonded to each other or connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic group A carbon atom of the monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, O, Se, Si, B, P and Al,
Each of R ₂ and R ₃ , R ₄ and R ₅ may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring. According to claim 1,
Wherein Q ₃ is a monocyclic 5-membered ring or 6-membered ring, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms composed of 2 to 5 polycyclic rings, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 50 carbon atoms A compound characterized in that it is a ring. According to claim 1,
When A in [Structural Formula 1] is CR ₇ , R ₇ is connected to each other and is represented by a ring represented by [Structural Formula Cy]. According to claim 1,
In the [Structural Formula Cy] and [Structural Formula Cy-Q3],
When W is any one selected from -CR ₁₄ R ₁₅ -, _{-CR 16} =, -C≡, -SiR ₁₇ R ₁₈ -, -SiR _{19 = and -Si≡,}
Wherein R ₁₄ to R ₁₉ are a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted A heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyltioxy group having 1 to 30 carbon atoms, A substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C1-C30 alkylamine group A compound, characterized in that selected from an alkylsilyl group of 30, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group. According to claim 1,
The [Formula A-1] to [Formula A-2] is a compound, characterized in that any one selected from the following [Compound 1] to [Compound 218]:

A first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode,
The organic light emitting device comprising at least one compound represented by the [Formula A-1] to [Formula A-2] according to claim 1 in which the organic layer. 7. The method of claim 6,
The organic layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
At least one of the layers comprises an organic light emitting compound represented by the [Formula A-1] to [Formula A-2]. 7. The method of claim 6,
The light emitting layer is an organic light emitting device comprising an anthracene derivative represented by the following [Formula C] as a host compound:
[Formula C]

In the [Formula C],
R ₂₁ to R ₂₈ are the same as or different from each other, and are the same as defined in R of claim 1 [Formula A-1] to [Formula A-2],
Ar ₉ and Ar ₁₀ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted Unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms Oxy group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted Any one selected from an arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,
L ₁₃ is a single bond, or any one selected from a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C2-C20 heteroarylene group,
k is an integer of 1 to 3, but when k is 2 or more, each L ₁₃ is the same as or different from each other. 9. The method of claim 8,
Ar ₉ of the [Formula C] is an organic light emitting device, characterized in that the substituent represented by the following [Formula C-1]:
[Formula C-1]

In the [Formula C],
R ₃₁ to R ₃₅ are the same or different, and are the same as defined in R of claim 1 [Formula A-1] to [Formula A-2], and combine with neighboring substituents to form a saturated or unsaturated ring can be formed 9. The method of claim 8,
The [Formula C] is an organic light emitting device, characterized in that any one selected from the following [Formula C1] to [Formula C57]:

8. The method of claim 7,
The hole transport layer and the electron blocking layer is an organic light emitting device, characterized in that it comprises a compound represented by the following [Formula D], respectively:
[Formula D]

In the above [Formula D],
R ₄₁ to R ₄₃ are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C number A 7 to 50 arylalkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, and a halogen group Any one selected from
L ₃₁ to L ₃₄ are the same or different from each other, and each independently is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms; ,
Ar ₃₁ to Ar ₃₄ are the same as or different from each other, and are each independently selected from a substituted or unsubstituted C 6 to C 50 aryl group and a substituted or unsubstituted C 2 to C 50 heteroaryl group,
n is an integer of 0 to 4, and when n is 2 or more, _{each aromatic ring including R 43} is the same as or different from each other,
m ₁ to m ₃ are an integer of 0 to 4, and when they are each 2 or more, each of R ₄₁ , R ₄₂ , or R ₄₃ is the same as or different from each other,
A carbon atom of the aromatic ring to which R _{41 to R 43} is not bonded is bonded to hydrogen or deuterium. 12. The method of claim 11,
At least one of Ar ₃₁ to Ar ₃₄ is an organic light emitting device, characterized in that a substituent represented by the following [Formula E]:
[Formula E]

In the [Formula E],
R ₅₁ to R ₅₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C number 2 to 30 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C5 to C30 cycloalkenyl group, substituted or unsubstituted A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C6 to C30 arylox Group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C5 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C1C group Any one selected from an arylamine group of 5 to 30, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group , they can each be linked to each other to form a ring,
Y is a carbon atom or a nitrogen atom, Z is a carbon atom, an oxygen atom, a sulfur atom or a nitrogen atom,
Ar ₃₅ to Ar ₃₇ are the same or different from each other, and each independently is any one selected from a substituted or unsubstituted C5 to C50 aryl group and a substituted or unsubstituted C3 to C50 heteroaryl group,
When Z is an oxygen atom or a sulfur atom, Ar ₃₇ is not present _{, when Y and Z are nitrogen atoms, only one of Ar 35} , Ar ₃₆ and Ar ₃₇ is present, and when Y is a nitrogen atom and Z is a carbon atom, Ar ₃₆ is does not exist,
However, one of R ₅₁ to R ₅₄ and Ar ₃₅ to Ar ₃₇ is a single bond connected to one of the linking groups _{L 31} to L ₃₄ in [Formula D]. 12. The method of claim 11,
The [Formula D] is an organic light emitting device, characterized in that any one selected from the following [Formula D1] to [Formula D79]:

12. The method of claim 11,
The [Formula D] is an organic light emitting device, characterized in that any one selected from the following [Formula D101] to [Formula D145]:

8. The method of claim 7,
The hole transport layer and the electron blocking layer are each organic light emitting device comprising a compound represented by the following [Formula F]:
[Formula F]

In the [Formula F],
R ₆₁ to R ₆₃ are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C number 2 to 30 alkenyl group, substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C5 to C30 cycloalkenyl group, substituted or unsubstituted A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, or a substituted or unsubstituted C6 to C30 arylox Group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C6 to C30 group A 6 to 30 arylamine group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, a substituted or unsubstituted C1 to C30 alkylgermanium group, Any one selected from a substituted or unsubstituted aryl germanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,
Ar ₅₁ to Ar ₅₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted C 6 to C 40 aryl group, or a substituted or unsubstituted C 2 to C 30 heteroaryl group. 16. The method of claim 15,
The [Formula F] is an organic light emitting device, characterized in that any one selected from the following [Formula F1] to [Formula F33]:

8. The method of claim 7,
At least one layer selected from each of the layers is an organic light emitting device, characterized in that formed by a deposition process or a solution process. 7. The method of claim 6,
The organic light emitting device may include a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; and monochromatic or white flexible lighting devices; An organic light emitting device, characterized in that used for any one selected from.