KR20200097584A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic light-emitting device including the same. More particularly, the present invention provides an organic electroluminescent device having a low driving voltage and remarkably improved current efficiency and life. The compound is represented by chemical formula 1.

Description

Organic compound and organic electroluminescent device containing the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic compound and an organic electroluminescent device including the same, and more particularly to an organic compound for a hole transport auxiliary layer of an organic electroluminescent device and an organic electroluminescent device including the same.

The organic electroluminescent device (OLED) has a simple structure and various advantages in the manufacturing process compared to other flat panel display devices such as conventional liquid crystal display devices (LCD), plasma display panels (PDP), and field emission displays (FED). High luminance and viewing angle characteristics are excellent, response speed is fast, and driving voltage is low, so it is actively developed and commercialized to be used as a light source for flat panel displays such as wall-mounted TVs or backlights of displays, lighting, and billboards.

The first organic EL device was reported (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, 913 pages, 1987) by Eastman Kodak's CW Tang and others. When a voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form an electron-hole pair of excitons, which are converted into light by transferring the energy of the excitons to the light emitting material.

More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and at least one organic layer between the two electrodes. At this time, the organic electroluminescent device is a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) or an electron from the anode. It is stacked in the order of an electron injection layer (EIL), and may further include a hole transport auxiliary layer or a hole blocking layer (HBL) before and after the emission layer in order to increase the efficiency of the emission layer.

The reason why the organic electroluminescent device has a multilayered thin film structure is to stabilize the interface between the electrode and the organic material, and to increase the luminous efficiency.

In particular, in the case of organic compounds used as materials for multi-layered thin films, the difference in the speed of movement of holes and electrons is large according to each characteristic, so that holes and electrons are effectively transferred to the light emitting layer only when a hole transport layer and an electron transport layer containing an appropriate compound are used. And, since the density of holes and electrons is balanced, luminous efficiency can be excellently improved.

For this reason, the characteristics of the organic compound components included in each layer of the organic thin film layer not only greatly affect the driving voltage, luminous efficiency, luminance, and lifetime of the device, but also affect the efficiency or lifetime of the finally produced display. Therefore, it is considered important to use a specific organic material suitable for a multilayer structure in an organic electroluminescent device.

Accordingly, studies on components included in each layer of the organic thin film layer are actively being conducted.

(Patent Document 1) KR 10-2014-0133572 A1

An object of the present invention is to provide a novel organic compound and an organic electroluminescent device including the same.

Another object of the present invention is that it has a HOMO energy level that facilitates hole transport, has a high LUMO energy level that can block electrons, has excellent hole transport properties, and can be used as a material for a hole transport layer or an electron blocking layer of an organic electroluminescent device. It is intended to provide a new compound that is present.

Another object of the present invention is to provide an organic electroluminescent device having significantly improved voltage, luminous efficiency and lifetime characteristics by using a hole transport layer or an electron blocking layer including a novel organic compound.

Another object of the present invention is to provide an organic electroluminescent device suitable for AM-OLED by using the organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

here,

l is an integer from 0 to 4,

L ₁ to L ₃ are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 5 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, a substituted or unsubstituted C 3 to It is selected from the group consisting of 20 cycloalkylene groups and substituted or unsubstituted heterocycloalkylene groups having 3 to 20 carbon atoms,

R ₀ is each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 heteroalkyl groups, substituted or unsubstituted aralkyl groups having 6 to 30 carbon atoms, substituted or unsubstituted aryl groups having 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted unsubstituted Heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a heteroalkenyl group having 1 to 20 carbon atoms of the ring,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,

At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted naphthyl group,

Ar ₃ and Ar ₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number of 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,

When the L ₁ to L ₃ , R ₀ and Ar ₁ to Ar ₄ are substituted, hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, Alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 carbon atoms, aryl group having 5 to 30 carbon atoms, carbon number A heteroaryl group having 2 to 30, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and aryloxy having 6 to 30 carbon atoms It is substituted with a substituent selected from the group consisting of groups, and when substituted with a plurality of substituents, they are the same as or different from each other.

In addition, the present invention is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the one or more organic material layers contains a compound represented by Formula 1 above. Device.

For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, and the like. However, the structure of the organic electroluminescent device is not limited thereto, and may include a smaller number of organic material layers.

According to a preferred embodiment of the present invention, the organic material layer is a hole transport layer or an electron blocking layer, and the hole transport layer or the electron blocking layer may be characterized in that it contains the compound represented by Formula 1.

In the present specification, “halogen group” is fluorine, chlorine, bromine or iodine.

In the present invention, “alkyl” refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

In the present invention, "alkylthio" means the above-described alkyl group bonded through a sulfur linkage (-S-).

In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and dimethylfluorenyl, but are not limited thereto.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, and R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include. Examples of the alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "alkoxy" may be a straight chain, branched chain or cyclic chain. Although the number of carbon atoms of the alkoxy is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present invention, "aralkyl" refers to an aryl-alkyl group in which aryl and alkyl are as described above. Preferred aralkyls include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl and naphthalenylmethyl. Bonding to the parent moiety is made through alkyl.

In the present invention, "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, "alkylamino group" means an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, "aralkylamino group" refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, "heteroarylamino group" refers to an aryl group having 6 to 30 carbon atoms and an amine group substituted with a heterocyclic group.

In the present invention, "heteroaralkyl group" refers to an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, but are not limited thereto.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se Is substituted with a hetero atom such as. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylene group" refers to a divalent group having two bonding positions in the aryl group. Except that each of these is a divalent group, the description of the aryl group described above may be applied. For example, it may be phenylene, biphenylene, naphthylene, anthracenylene, or fluorenylene.

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

In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present invention, 　“adjacent 　 groups are bonded to each other to form a ring” means 　adjacent 　 groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these.

In the present specification, “alicyclic compound” has the same meaning as “aliphatic hydrocarbon ring”, and refers to a ring consisting of only carbon and hydrogen atoms as a non-aromatic ring.

In the present specification, “hetero-alicyclic compound” refers to an alicyclic compound including at least one heteroatom by substitution of one or more carbons of the “aliphatic hydrocarbon ring” with a hetero atom.

In the present specification, examples of the "aromatic hydrocarbon ring" include a phenyl group, a naphthyl group, an anthracenyl group, and the like, but are not limited thereto.

In the present specification, "aliphatic heterocycle" refers to an aliphatic ring including one or more of heteroatoms.

In the present specification, "aromatic heterocycle" refers to an aromatic ring including at least one heteroatom.

In the present specification, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocycle, and an aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted. , Two or more substituents may be the same or different from each other. The substituent is hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, carbon number Aralkyl group having 6 to 30, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, carbon number It may be substituted with one or more substituents selected from the group consisting of an arylamino group having 6 to 30, an aralkylamino group having 6 to 30 carbon atoms, and a hetero arylamino group having 2 to 24 carbon atoms, but is not limited to the above examples.

The present invention relates to a novel organic compound, has a HOMO energy level that facilitates hole transport, has a high LUMO energy level capable of blocking electrons, has excellent hole transport characteristics, and has excellent hole transport properties, and a hole transport layer or electron blocking of an organic electroluminescent device Can be used as a layer material.

In addition, by using the hole transport layer or the electron blocking layer including the novel organic compound, it is possible to provide an organic electroluminescent device in which most device characteristics such as voltage, current efficiency, and lifespan are remarkably improved.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. However, the present invention may be implemented in various different forms and is not limited to the embodiments described herein.

The organic compound according to the present invention is a light emitting layer material and has excellent low crystallinity and chemical stability, charge mobility, and interfacial properties with an electrode or an adjacent layer.

Accordingly, it is possible to significantly improve the voltage, luminous efficiency, and lifetime characteristics of the organic electroluminescent device.

Specifically, the compound represented by the following formula 1 is as follows:

[Formula 1]

here,

l is an integer from 0 to 4,

L ₁ to L ₃ are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 5 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, a substituted or unsubstituted C 3 to It is selected from the group consisting of 20 cycloalkylene groups and substituted or unsubstituted heterocycloalkylene groups having 3 to 20 carbon atoms,

R ₀ is each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 heteroalkyl groups, substituted or unsubstituted aralkyl groups having 6 to 30 carbon atoms, substituted or unsubstituted aryl groups having 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted unsubstituted Heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a heteroalkenyl group having 1 to 20 carbon atoms of the ring,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,

At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted naphthyl group,

Ar ₃ and Ar ₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number of 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,

When the L ₁ to L ₃ , R ₀ and Ar ₁ to Ar ₄ are substituted, hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, Alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 carbon atoms, aryl group having 5 to 30 carbon atoms, carbon number A heteroaryl group having 2 to 30, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and aryloxy having 6 to 30 carbon atoms It is substituted with a substituent selected from the group consisting of groups, and when substituted with a plurality of substituents, they are the same as or different from each other.

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently a substituent represented by the following Formula 2 or Formula 3:

[Formula 2]

[Chemical Formula 3]

here,

* Means the part to be joined,

n is an integer from 0 to 7,

m is an integer from 0 to 5,

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,

When the R ₁ and R ₂ are substituted, hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, 6 to 30 carbon atoms Aralkyl group, C 5 to C 30 aryl group, C 2 to C 30 heteroaryl group, C 3 to C 30 heteroarylalkyl group, C 3 to C 30 cycloalkyl group, C 1 to C 20 heterocycloalkyl group, C 1 to C It is substituted with a substituent selected from the group consisting of a cycloalkenyl group of 20 and a heteroalkenyl group having 1 to 20 carbon atoms, and when substituted with a plurality of substituents, they are the same or different from each other.

The compound represented by Formula 1 may be selected from the group consisting of compounds represented by the following Formulas 4 to 9:

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

here,

o and s are the same as or different from each other, and each independently an integer of 0 to 7,

p is an integer from 0 to 5,

q is an integer from 0 to 4,

R ₃ to R ₆ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted It is selected from the group consisting of an aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms,

The substituents of L ₁ to L ₃ and Ar ₁ to Ar ₄ are as defined in Chemical Formula 1.

Ar ₃ and Ar ₄ 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 anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl Group consisting of a (pyrene) group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzosilol group Is selected from

When the phenyl, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl (pyrene) group, fluorenyl group, carbazolyl group, dibenzothiophenyl group, dibenzofuranyl group, dibenzosilol group are substituted, hydrogen, Deuterium, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, an aryl group having 5 to 30 carbon atoms, a carbon number A heteroaryl group having 2 to 30, a heteroarylalkyl group having 3 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 1 to 20 carbon atoms, a cycloalkenyl group having 1 to 20 carbon atoms, and a heteroal having 1 to 20 carbon atoms It is substituted with a substituent selected from the group consisting of a kenyl group, and when substituted with a plurality of substituents, they are the same as or different from each other.

The compound represented by Formula 1 may be selected from the group consisting of the following compounds:

The compound of Formula 1 of the present invention may be usefully used as a material for a hole transport layer or an electron blocking layer.

Specifically, the organic compound is a light emitting layer material and has excellent low crystallinity and chemical stability, charge mobility, and interfacial properties with an electrode or an adjacent layer. Due to these characteristics, when the organic compound is used as a material for an organic light emitting device, it may exhibit equivalent or excellent characteristics in most device characteristics such as voltage, current efficiency, and life.

The present invention provides an organic electroluminescent device including the compound represented by Chemical Formula 1.

The organic compound of the present invention can be usefully used as a material for a hole transport auxiliary layer.

In addition, the present invention relates to a material for a light-emitting layer comprising the organic compound.

In addition, the present invention is an organic electroluminescent device in which an organic thin film layer comprising at least one layer or a plurality of layers including a light emitting layer is stacked between a cathode and an anode,

The organic thin film layer is a hole transport auxiliary layer between the first electrode and the emission layer.

The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and a hole blocking layer is further stacked if necessary. Can be.

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention has a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, a light emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked. And, preferably, an electron blocking layer (EBL) between the anode and the emission layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the emission layer. In addition, a hole blocking layer (HBL) may be further included between the cathode and the emission layer.

In the method of manufacturing an organic light emitting diode according to the present invention, first, an anode is formed by coating a material for an anode on a substrate surface in a conventional manner. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness. In addition, as a material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer is formed on the anode surface by vacuum thermal evaporation or spin coating with a hole injection layer (HIL) material in a conventional manner. Materials for the hole injection layer include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenyl). Amino) phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris Examples include (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer is formed by vacuum thermal evaporation or spin coating of the compound of the present invention on the surface of the hole injection layer.

A light emitting layer is formed by vacuum thermal evaporation or spin coating on the surface of the hole transport auxiliary layer with a light emitting layer (EML) material in a conventional manner. At this time, as a single light-emitting material or a light-emitting host material among the light-emitting layer materials used, tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ), etc. may be used for green, and Alq ₃ , CBP (4, 4'-N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicarbazole-biphenyl), PVK(poly(n-vinylcabazole), poly(n-vinylcarbazole)), ADN( 9,10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalen-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene , 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl) anthracene, 3-tert-butyl -9,10-di (naphth-2 days) anthracene), E3, DSA (distyrylarylene, distyrylarylene), or a mixture of two or more thereof may be used, but the present invention is not limited thereto.

In the case of a dopant that can be used with a light emitting host among the light emitting layer materials, IDE102 and IDE105 available from Idemitsu, and as a phosphorescent dopant, tris(2-phenylpyridine)iridium(III)( Ir(ppy)3), iridium(III)bis[(4,6-difluorophenyl)pyridinato-N,C-2′]picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084]), platinum (II) octaethyl porphyrin (PtOEP), TBE002 (Cobion), and the like can be used.

An electron transport layer is formed by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material on the surface of the light emitting layer in a conventional manner. At this time, the electron transport layer material to be used is not particularly limited, and preferably tris(8-hydroxyquinolinolato)aluminum (Alq ₃ ) may be used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer, it is possible to prevent the phenomenon that triplet excitons or holes are diffused into the electron transport layer. .

The hole blocking layer may be formed by vacuum thermal evaporation and spin coating on the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but is preferably (8-hydroxyquinolinola). To) lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF, and the like may be used.

An electron injection layer is formed by vacuum thermal evaporation or spin coating on the surface of the electron transport layer with an electron injection layer (EIL) material in a conventional manner. In this case, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the electron injection layer material used.

A negative electrode is formed by vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer in a conventional manner.

At this time, the negative electrode materials used are lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) and the like can be used. In addition, in the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

A capping layer (CPL) may be formed on the surface of the negative electrode by the composition for forming a capping layer of the present invention.

Hereinafter, a method for synthesizing the compounds will be described below with a representative example. However, the method for synthesizing the compounds of the present invention is not limited to the method illustrated below, and the compounds of the present invention may be prepared by the method illustrated below and a method known in the art.

<Synthesis Example 1-Preparation of Compound 1>

[Synthesis Example 1-1: Preparation of Intermediate 1-1]

2-Bromo-9H-fluorenone (42.0 g, 0.16 mol) was dissolved in 400 mL of anhydrous tetrahydrofuran in a flask dried by heating in a 1 L flask under a nitrogen stream.

After stirring at -10°C or less, 0.5M 2-naphthalene magnesium bromide (320 mL, 0.16 mol) was added dropwise, and the temperature was raised to 70°C, followed by stirring. After the reaction for 12 hours, it was cooled to room temperature, and a saturated aqueous ammonium chloride solution was added thereto and stirred.

The organic layer was extracted and washed 3 times with water. The extracted solution was treated with MgSO4 to remove residual moisture, concentrated under reduced pressure, and purified by column chromatography to obtain 33.3 g of Intermediate 1-1 in 67% yield.

[Synthesis Example 1-2: Preparation of Intermediate 1-2]

2-bromo-9-(naphthalen-2-yl)-9H-fluoren-9-ol (25.0. g, 81.1 mmol) and 625 mL of benzene were added to a 1L flask, stirred at 0 °C or less, and then sulfuric acid (43.2 mL). , 0.81 mol) was slowly added dropwise. After the dropwise addition, the temperature was increased to 120° C. and stirred. The reaction was terminated after 3 hours. After adding 2M NaOH, the ethyl acetate layer was extracted using ethyl acetate and water.

The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, and purified by column chromatography to obtain 19.5 g of Intermediate 1-2 in 53.9% yield.

[Synthesis Example 1-3: Preparation of Intermediate 1-3]

2-bromo-9-(naphthalen-2-yl)-9-phenyl-9H-fluorene (19.0 g, 42.5 mmol), 9,9-dimethyl-9H-fluorene-2 in a 250 mL flask under nitrogen stream -Amine (10.67 g, 50.96 mmol), sodium tert butoxide (8.16 g, 84.94 mmol) tris(dibenzylideneacetone)dipalladium(0) (0.78 g, 0.849 mmol), tri-tert-butylphosphine 50% Toluene solution (0.8 mL, 3.39 mmol) and 190 mL of toluene were added and stirred to reflux.

After completion of the reaction, the toluene layer was extracted using 50 mL of water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, and purified using a column chromatography method to obtain 20.1 g of Compound 3 in 82.2% yield.

[Synthesis Example 1-4: Preparation of Compound 1]

In a 250 mL flask under a nitrogen stream, N-(9,9-dimethyl-9H-fluoren-2-yl)-9-(naphthalen-2-yl)-9-phening-9H-fluoren-2-amine (10.0 g, 17.37 mmol), 2-bromo-1,1'-biphenyl (4.45 g, 19.1 mmol), sodium tert butoxide (3.34 g, 34.74 mmol) tris(dibenzylideneacetone)dipalladium(0) ( 0.32 g, 0.3474 mmol), tri-tert-butylphosphine 50% toluene solution (0.33 mL, 1.389 mmol) and 100 mL of toluene were added and stirred to reflux.

After completion of the reaction, a toluene layer was extracted using toluene and water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, purified by column chromatography, and recrystallized with dichloromethane/methanol to obtain 7.65 g of Compound 1 in 60.5% yield.

<Synthesis Example 2-Preparation of Compound 2>

In a 250 mL flask under a nitrogen stream, N-(9,9-dimethyl-9H-fluoren-2-yl)-9-(naphthalen-2-yl)-9-phening-9H-fluoren-2-amine (10.0 g, 17.37 mmol), 4-bromo-1,1'-biphenyl (4.45 g, 19.1 mmol), sodium tert butoxide (3.34 g, 34.74 mmol) tris(dibenzylideneacetone)dipalladium(0) ( 0.32 g, 0.3474 mmol), tri-tert-butylphosphine 50% toluene solution (0.33 mL, 1.389 mmol) and 100 mL of toluene were added and stirred to reflux.

After completion of the reaction, a toluene layer was extracted using toluene and water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, purified by column chromatography, and recrystallized with dichloromethane/methanol to obtain 8.25 g of Compound 2 in 63.5% yield.

<Example 1: Preparation of an organic electroluminescent device using Synthesis Example 1 (Compound 1) as a hole transport layer material>

A substrate in which Ag alloy as a light-reflecting layer and ITO (10 nm) as an anode of an organic light emitting device were sequentially stacked was patterned by dividing into a cathode, an anode region, and an insulating layer through a photo-lithograph process. The surface was treated with O2:N2 plasma for the purpose of increasing the work-function of the anode (ITO) and descum. On it, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed with a thickness of 100 Å as a hole injection layer (HIL). Subsequently, Synthesis Example 1 (Compound 1) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1000 Å. N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9'-fluorene]-2'-yl)phenyl) di as an electron blocking layer (EBL) on the hole transport layer (HTL) Benzo[b,d]furan-4-amine is formed to a thickness of 150 Å, and α,β-ADN is deposited as a host material capable of forming Blue EML as a light emitting layer (EML) on the electron blocking layer (EBL). While being doped with N1,N1,N6,N6-tetrakis(4-(1-silyl)phenyl)pyrene-1,6-diamine as a dopant, a light emitting layer was formed with a thickness of 200 Å.

On it, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and LiQ in a weight ratio of 1:1 By mixing, an electron transport layer (ETL) was deposited to a thickness of 360 Å, and magnesium (Mg) and silver (Ag) were deposited as a cathode to a thickness of 160 Å in a 9:1 ratio. N4,N4'-diphenyl-N4,N4'-bis(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]- as a capping layer on the negative electrode 4,4'-diamine was deposited to a thickness of 63 to 65 nm. An organic electroluminescent device was manufactured by attaching a seal cap on the capping layer (CPL) with a UV-curable adhesive to protect the organic electroluminescent device from O2 or moisture in the atmosphere.

<Example 2>

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Synthesis Example 2 (Compound 2) was used instead of Synthesis Example 1 (Compound 1) as the hole transport layer in Example 1.

<Comparative Example 1>

In the hole transport layer in Example 1, instead of Synthesis Example 1 (Compound 1), NPB(N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1' An organic electroluminescent device was manufactured in the same manner as in Example 1, except that -biphenyl]-4,4'-diamine) was used.

<Experimental Example: Analysis of characteristics of an organic EL device>

Comparative Example 1 and Examples 1 by using the organic electroluminescent element prepared in 2 show the voltage, current efficiency, and lifetime characteristics of the electro-optic characteristics and 20mA / cm ² at a current of 10mA / cm ² in Table 1 below Done.

division compound Driving voltage Luminance efficiency Color coordinates life span HTL Volt Cd/m ² Cd/A lm/W CIEx CIEy T@95% Comparative Example 1 NPB 4.6 398 4.0 3.0 0.142 0.05 90 Example 1 Synthesis Example 1
(Compound 1) 4.29 667 6.7 4.9 0.139 0.0490 150 Example 2 Synthesis Example 2 (Compound 2) 4.21 565 6.6 4.9 0.139 0.049 120

From Table 1 above, it can be seen that when the compound according to the present invention is used as a material for a hole transport layer or an electron blocking layer, it can be seen that the compound of the comparative example exhibits equivalent or superior characteristics in most device characteristics, such as voltage, current efficiency, and lifespan, compared to the compound of the comparative example. .

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims are also present. It belongs to the scope of rights of

Claims (8)

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

here,
l is an integer from 0 to 4,
L ₁ to L ₃ are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 5 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, a substituted or unsubstituted C 3 to It is selected from the group consisting of 20 cycloalkylene groups and substituted or unsubstituted heterocycloalkylene groups having 3 to 20 carbon atoms,
R ₀ is each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 heteroalkyl groups, substituted or unsubstituted aralkyl groups having 6 to 30 carbon atoms, substituted or unsubstituted aryl groups having 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted unsubstituted Heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a heteroalkenyl group having 1 to 20 carbon atoms of the ring,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted naphthyl group,
Ar ₃ and Ar ₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number of 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,
When the L ₁ to L ₃ , R ₀ and Ar ₁ to Ar ₄ are substituted, hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, Alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 carbon atoms, aryl group having 5 to 30 carbon atoms, carbon number A heteroaryl group having 2 to 30, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and aryloxy having 6 to 30 carbon atoms It is substituted with a substituent selected from the group consisting of groups, and when substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 1,
The compounds Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently a substituent represented by the following Formula 2 or Formula 3:
[Formula 2]

[Chemical Formula 3]

here,
* Means the part to be joined,
n is an integer from 0 to 7,
m is an integer from 0 to 5,
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to 24 Of alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Aryl group, substituted or unsubstituted unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted 3 to carbon atoms It is selected from the group consisting of 20 cycloalkenyl groups and substituted or unsubstituted heteroalkenyl groups having 1 to 20 carbon atoms,
When the R ₁ and R ₂ are substituted, hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, 6 to 30 carbon atoms Aralkyl group, C 5 to C 30 aryl group, C 2 to C 30 heteroaryl group, C 3 to C 30 heteroarylalkyl group, C 3 to C 30 cycloalkyl group, C 1 to C 20 heterocycloalkyl group, C 1 to C It is substituted with a substituent selected from the group consisting of a cycloalkenyl group of 20 and a heteroalkenyl group having 1 to 20 carbon atoms, and when substituted with a plurality of substituents, they are the same or different from each other. The method of claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of compounds represented by the following Formulas 4 to 9:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

here,
o and s are the same as or different from each other, and each independently an integer of 0 to 7,
p is an integer from 0 to 5,
q is an integer from 0 to 4,
R ₃ to R ₆ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted It is selected from the group consisting of an aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms,
The substituents of L ₁ to L ₃ and Ar ₁ to Ar ₄ are as defined in claim 1. The method of claim 1,
Ar ₃ and Ar ₄ 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 anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl Group consisting of a (pyrene) group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzosilol group Is selected from
When the phenyl, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl (pyrene) group, fluorenyl group, carbazolyl group, dibenzothiophenyl group, dibenzofuranyl group, dibenzosilol group are substituted, hydrogen, Deuterium, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, an aryl group having 5 to 30 carbon atoms, a carbon number A heteroaryl group having 2 to 30, a heteroarylalkyl group having 3 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 1 to 20 carbon atoms, a cycloalkenyl group having 1 to 20 carbon atoms, and a heteroal having 1 to 20 carbon atoms It is substituted with a substituent selected from the group consisting of a kenyl group, and when substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of the following compounds:

A first electrode; A second electrode facing the first electrode; At least one organic material layer interposed between the first electrode and the second electrode,
The at least one organic material layer comprises at least one compound according to claim 1
Organic electroluminescent device. The method of claim 6,
The organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer.
Organic electroluminescent device. The method of claim 6,
The organic material layer is a hole transport layer or an electron blocking layer
Organic electroluminescent device.