KR20190121739A - Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent device having excellent current efficiency and luminous efficiency can be manufactured by using the organic electroluminescent compound of the present invention.

Description

Organic electroluminescent compound and organic electroluminescent device including the same {Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same}

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.

Among the display elements, an electroluminescent device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

The most important factor that determines the luminous efficiency in the organic electroluminescent device is the light emitting material. Fluorescent materials are widely used as luminescent materials to date, but development studies of phosphorescent luminescent materials are widely conducted in that phosphorescent luminescent materials can theoretically improve emission efficiency up to four times compared to fluorescent luminescent materials due to the mechanism of electroluminescence. It is becoming. To date, the iridium (III) complex is widely known as a phosphorescent material, and bis (2- (2'-benzothienyl) -pyridinate-N, C-3 ') iridium (acetylacetonate) for each RGB ) [(acac) Ir (btp) ₂ ], tris (2-phenylpyridine) iridium [Ir (ppy) ₃ ] and bis (4,6-difluorophenylpyridinato-N, C2) picoline Materials such as Toyridium (Firpic) are known.

In the prior art, 4,4'-N, N'-dicarbazole-biphenyl (CBP) was the most widely known phosphorescent host material. Recently, Batocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate), which Pioneer et al. In Japan have been used as materials for hole blocking layers ( He developed a high-performance organic electroluminescent device using Balq) as a host material.

However, existing materials have advantages in terms of luminescence properties, but have the following disadvantages: (1) The glass transition temperature is low and the thermal stability is low, which deteriorates during the high temperature deposition process under vacuum, and the lifetime of the device is reduced. (2) The power efficiency is inversely proportional to the voltage in the relationship of power efficiency = [(π / voltage) × current efficiency] in the organic electroluminescent device, but the organic electroluminescent device using the phosphorescent host material is an organic electroluminescent device using the fluorescent material. The current efficiency (cd / A) is higher than that of the light emitting device, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w). (3) In addition, when used in an organic electroluminescent element, it is not satisfactory in terms of operating life, and the luminous efficiency is still required to be improved.

On the other hand, the organic electroluminescent device has a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer in order to increase the efficiency and stability thereof. At this time, selection of a compound included in the hole transport layer or the like is recognized as a means for improving device characteristics such as hole transport efficiency, light emission efficiency, and life time to the light emitting layer.

In this regard, copper phthalocyanine (CuPc), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB), N, N as hole injection and transfer material in organic electroluminescent devices '-Diphenyl-N, N'-bis (3-methylphenyl)-(1,1'-biphenyl) -4,4'-diamine (TPD), 4,4', 4 "-tris (3-methylphenyl Phenylamino) triphenylamine (MTDATA) has been used, but the organic electroluminescent device has a problem of deterioration of quantum efficiency and lifespan when such materials are used. This is because thermal stress is generated between the anode and the hole injection layer, and the lifetime of the device is drastically reduced due to the thermal stress.In addition, the organic material used in the hole injection layer has a very high hole mobility. As a result, the hole-electron charge balance between holes and electrons is broken, resulting in low quantum efficiency (cd / A). It becomes.

Korean Unexamined Patent Publication No. 2012-0029446, WO 2013-065589 and WO 2007-119800 disclose amine derivatives having benzofluorene-based substituents as compounds for organic electroluminescent devices. .

However, the benzofluorene-based substituents in the above document are all benzo [a] fluorene or benzo [c] fluorene-based substituents, and amine derivatives having benzo [b] fluorene-based substituents are not specifically disclosed. .

Korean Laid-Open Patent Publication KR 2012-0029446 A (Published March 26, 2012) International Publication WO 2013-065589 A1 (published May 10, 2013) International Publication WO 2007-119800 A1 (published Oct. 25, 2007)

An object of the present invention is to provide an organic electroluminescent compound excellent in current efficiency and luminous efficiency and an organic electroluminescent device comprising the same.

As a result of earnest research to solve the above technical problem, the present inventors have found that the organic electroluminescent compound represented by the following Chemical Formula 1 achieves the above-mentioned object, and completed the present invention.

[Formula 1]

In Chemical Formula 1,

Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl; Ar ₁ and Ar ₂ may be fused to form a ring;

Ar ₅ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl;

L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;

L ₂ is substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl,- N (R ₁₁ ) (R ₁₂ ), —Si (R ₁₃ ) (R ₁₄ ) (R ₁₅ ), —S (R ₁₆ ), —O (R ₁₇ ), cyano, nitro, or hydroxy; May be linked to an adjacent substituent to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic rings are replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;

R ₁₁ to R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; May be linked to an adjacent substituent to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic ring are one or more heteroatoms selected from nitrogen, oxygen and sulfur. May be substituted;

n and m are each independently an integer of 0 to 1, provided that n and m cannot be 0 at the same time;

a is an integer of 1 to 3, and when a is an integer of 2 or more, each R ₁ may be the same or different;

b is an integer from 1 to 6, and when b is an integer of 2 or more, each R ₂ may be the same or different;

The heteroaryl (ene) comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;

The heterocycloalkyl includes one or more heteroatoms selected from O, S and N.

The organic electroluminescent compound according to the present invention has an advantage of manufacturing an organic electroluminescent device having excellent current efficiency and luminous efficiency.

1 shows a basic skeleton of an organic electroluminescent compound of the present application.

Hereinafter, the present invention will be described in more detail, but this is for explanation and should not be construed as a method of limiting the scope of the present invention.

The present invention relates to an organic electroluminescent compound represented by Chemical Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the organic electroluminescent compound.

Hereinafter, the organic electroluminescent compound represented by Chemical Formula 1 will be described in more detail.

Specific examples of "alkyl" described in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl and the like. Specific examples of "alkenyl" herein include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. Examples of “alkynyl” herein include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. Examples of “cycloalkyl” herein include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7 ring skeleton atoms, at least one heteroatom selected from the group consisting of B, N, O, S, P (= 0), Si and P, Preferred are cycloalkyls comprising at least one heteroatom selected from O, S and N, for example tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "aryl (ene)" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon, for example phenyl, biphenyl, terphenyl, naphthyl, vinaphthyl, phenylnaphthyl, naphthylphenyl, flu Orenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, peryllenyl, chrysenyl , Naphthacenyl, fluoranthenyl and the like. As used herein, "(5- to 30-membered) heteroaryl (ene)" has 5 to 30 ring skeleton atoms, and at least one hetero selected from the group consisting of B, N, O, S, P (= 0), Si and P An aryl group containing an atom is meant. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl (ene) herein also includes a form in which one or more heteroaryl or an aryl group is connected to a heteroaryl group by a single bond. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazyl, pyridyl, bipyridyl, pyrazinyl, pyrimidyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuran Dibenzothiophenyl, naphthofuranyl, naphthothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxa Zolyl, isoindoleyl, indolyl, indolinyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenantridinyl, Fused ring heteroaryl such as benzodioxolyl. "Halogen" herein includes F, Cl, Br and I atoms.

"Substituted" in the description of "substituted or unsubstituted" described in the present invention means that the hydrogen atom is replaced by another atom or another functional group (ie a substituent) in a certain functional group. In Ar ₁ to Ar ₅ , L ₁ to L ₂ , R ₁ and R ₂ , and R ₁₁ to R ₁₇ of Formula 1, substituted alkyl (lene), substituted aryl (lene), substituted heteroaryl (ene), substituted Substituents of cycloalkyl, substituted heterocycloalkyl, and substituted aralkyl are each independently deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl, (3-30 membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri ( C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) Alkynyl, cyano, di (C1-C30) alkylamino, di (C6-C30) arylamino unsubstituted or substituted with (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) arylamino, Di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl , D (C1- C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxy means one or more selected from the group consisting of, each independently (C1-C30) alkyl, (C6-C21) aryl, (C6-C12 It is preferably one or more selected from the group consisting of (5-21 membered) heteroaryl unsubstituted or substituted with) aryl, and di (C6-C21) arylamino.

According to an embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of the following Formulas 2 to 4, preferably, the compound represented by Formula 1 may be represented by the following Formula 2 or 3 have.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, Ar ₁ to Ar ₅ , L ₁ to L ₂ , R ₁ and R ₂ , a and b are the same as defined in Formula 1 above.

In Formulas 1 to 4, Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, Ar ₁ and Ar ₂ Can fuse to form a ring; Preferably substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5- to 21 membered) heteroaryl, Ar ₁ and Ar ₂ may be fused to form a ring; More preferably, it is a substituted or unsubstituted (C6-C21) aryl, wherein the substituent of (C6-C21) aryl is (C6-C30) alkyl, (C1-C10) alkyl substituted or unsubstituted (C6 Or one or more selected from the group consisting of (5-21 membered) heteroaryl unsubstituted or substituted with (C6-C12) aryl, and Ar ₁ and Ar ₂ may be fused to form a ring. have. Specifically, Ar ₁ to Ar ₄ may be each independently phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or benzofluorenyl, each of which is independently (C1-C4) alkyl, phenyl, In the group consisting of naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, isoquinolinyl, quinazolinyl, 9-phenylcarbazolyl, dibenzothiophenyl and dibenzofuranyl It may be substituted with one or more selected, Ar ₁ and Ar ₂ may be fused to form a ring.

Ar ₅ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl; Preferably substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, or substituted or unsubstituted (5-21 membered) heteroaryl. More preferably, Ar ₅ is unsubstituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, (6-21 membered) heteroaryl or di (C6-C18) arylamino; Or (6-21) membered heteroaryl unsubstituted or substituted with (C1-C10) alkyl or (C6-C18) aryl, including heteroatoms selected from N, O and S. Specifically, Ar ₅ is (C1-C4) alkyl; Phenyl, biphenyl, naphthyl, phenanthrenyl or fluorenyl, unsubstituted or substituted with (C1-C4) alkyl, phenyl, carbazolyl, diphenyltriazinyl, phenylbenzimidazolyl or diphenylamino; Carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, or dibenzofuranyl, unsubstituted or substituted with phenyl.

L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene; Preferably a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5-21 membered) heteroarylene. More preferably, L ₁ is a single bond; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; Or a (5-18 membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl containing a nitrogen atom as a heteroatom. Specifically, L ₁ is a single bond, phenyl or pyrimidyl.

L ₂ is substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene; Preferably substituted or unsubstituted (C1-C20) alkylene, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5-21 membered) heteroarylene. More preferably, L ₂ is unsubstituted (C1-C10) alkylene; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; Or (6-21 membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl containing an oxygen atom as a heteroatom. Specifically, L ₂ is (C 1 -C 4) alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, or dibenzofuranyl.

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5-30 member ) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -N (R ₁₁ ) (R ₁₂ ), -Si (R ₁₃ ) (R ₁₄ ) (R ₁₅ ), -S (R ₁₆ ), -O (R ₁₇ ), cyano, nitro, or hydroxy, or May be linked to an adjacent substituent to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic rings are replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be; R ₁₁ to R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5-30 member ) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; May be linked to an adjacent substituent to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic ring are one or more heteroatoms selected from nitrogen, oxygen and sulfur. Can be substituted. Preferably, R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-21 membered) Heteroaryl or -N (R ₁₁ ) (R ₁₂ ), wherein R ₁₁ and R ₁₂ are each independently a substituted or unsubstituted (C6-C21) aryl. More preferably, R ₁ and R ₂ are each independently hydrogen; Unsubstituted (C6-C18) aryl; Unsubstituted (6- to 18-membered) heteroaryl containing a nitrogen atom as a hetero atom; Or -N (R ₁₁ ) (R ₁₂ ); R ₁₁ and R ₁₂ are each independently unsubstituted (C6-C18) aryl. Specifically, R ₁ and R ₂ are hydrogen, phenyl, pyridyl, pyrimidyl, diphenylamino or phenylnaphthylamino.

N and m are each independently an integer of 0 to 1, provided that n and m cannot be 0 at the same time.

A is an integer of 1 to 3, and when a is an integer of 2 or more, each R ₁ may be the same or different; Preferably a is 1.

B is an integer from 1 to 6, and when b is an integer of 2 or more, each R ₂ may be the same or different; Preferably b is 1.

According to an embodiment of the present invention, in Formulas 1 to 4, Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5-21 membered) heteroaryl , Ar ₁ and Ar ₂ may be fused to form a ring; Ar ₅ is substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, or substituted or unsubstituted (5-21 membered) heteroaryl; L ₁ is a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5-21 membered) heteroarylene; L ₂ is substituted or unsubstituted (C1-C20) alkylene, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5-21 membered) heteroarylene; R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-21 membered) heteroaryl, Or -N (R ₁₁ ) (R ₁₂ ); R ₁₁ and R ₁₂ are each independently a substituted or unsubstituted (C6-C21) aryl; N and m are each independently an integer of 0 to 1, provided that n and m cannot be 0 at the same time; A is an integer of 1 to 3, and when a is an integer of 2 or more, each R ₁ may be the same or different; B is an integer from 1 to 6, and when b is an integer of 2 or more, each R ₂ may be the same or different; The heteroaryl (ene) comprises one or more heteroatoms selected from N, O and S.

According to another embodiment of the present invention, in Formulas 1 to 4, Ar ₁ to Ar ₄ are substituted or unsubstituted (C6-C21) aryl, wherein the substituent of (C6-C21) aryl is (C1 -C30) alkyl, (C6-C21) aryl unsubstituted or substituted with (C1-C10) alkyl, and (5-21 membered) heteroaryl unsubstituted or substituted with (C6-C12) aryl May be one or more, Ar ₁ and Ar ₂ may be fused to form a ring; Ar ₅ is unsubstituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, (6-21 membered) heteroaryl or di (C6-C18) arylamino; Or (6-21) membered heteroaryl unsubstituted or substituted with (C1-C10) alkyl or (C6-C18) aryl, including heteroatoms selected from N, O and S; L ₁ is a single bond; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; Or a (5- to 18-membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl containing a nitrogen atom as a heteroatom; L ₂ is unsubstituted (C1-C10) alkylene; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; Or (6-21 membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl containing an oxygen atom as a heteroatom; R ₁ and R ₂ are each independently hydrogen; Unsubstituted (C6-C18) aryl; Unsubstituted (6- to 18-membered) heteroaryl containing a nitrogen atom as a hetero atom; Or -N (R ₁₁ ) (R ₁₂ ); R ₁₁ and R ₁₂ are each independently unsubstituted (C6-C18) aryl; N and m are each independently an integer of 0 to 1, provided that n and m cannot be 0 at the same time; A is 1; B is 1.

The organic electroluminescent compound of Chemical Formula 1 may be exemplified more specifically as the following compound, but is not limited thereto.

The organic electroluminescent compounds according to the invention can be prepared by synthetic methods known to those skilled in the art, for example as shown in Schemes 1 and 2 below.

Scheme 1

Scheme 2

The present invention also provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the material.

The material may be composed of the organic electroluminescent compound of the present invention alone, and may further include conventional materials included in the organic electroluminescent material.

The organic electroluminescent device according to the present invention comprises a first electrode; Second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer may include at least one organic electroluminescent compound of Chemical Formula 1.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may include a light emitting layer, and may further include one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.

The organic electroluminescent compound of the present invention may be included in one or more of the light emitting layer and the hole transport layer. When used in the hole transport layer, the organic electroluminescent compound of the present invention may be included as a hole transport material. When used in the light emitting layer, the organic electroluminescent compound of the present invention may be included as a host material.

When the organic electroluminescent compound of the present invention is included as a hole transport material, the light emitting layer may include a known light emitting material or may include a compound of the present invention other than the compound of the present invention used as the hole transport material as a light emitting material. have. The known light emitting material may be a known host material, and may further include one or more dopants. The known host material may be a known fluorescent or phosphorescent host material.

In addition, when the organic electroluminescent compound of the present invention is included as a host material (first host material) of the light emitting layer, it may further include one or more dopants. In addition, a second host material may be further included, wherein the weight ratio of the first host material to the second host material is in the range of 1:99 to 99: 1.

Particularly preferred from the viewpoint of luminous efficiency is selected from the group consisting of compounds represented by the following formulas (5) to (7) as the known host material or the second host material.

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 5,

Cz has the following structure,

R ₂₁ to R ₂₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) Heteroaryl or R ₂₅ R ₂₆ R ₂₇ Si-, and R ₂₅ to R ₂₇ are each independently substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; L ₄ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene; M is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl; Y ₁ and Y ₂ are —O—, —S—, —N (R ₃₁ ) —, —C (R ₃₂ ) (R ₃₃ ) —, and Y ₁ and Y ₂ are not present simultaneously; R ₃₁ to R ₃₃ are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, and R ₃₂ And R ₃₃ can be the same or different; h and i are each independently an integer of 1 to 3, j, k, l and r are each independently an integer of 0 to 4, and when h, i, j, k, l or r is an integer of 2 or more, (Cz-L ₄ ), each (Cz), each R ₂₁ , each R ₂₂ , each R ₂₃ or each R ₂₄ may be the same or different.

Specifically, preferred examples of the host material are as follows.

The dopant is preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) is preferable. More preferred is an ortho metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferred is an ortho metallized iridium complex compound.

The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following formulas (8) to (10).

[Formula 8]

[Formula 9]

[Formula 10]

In Chemical Formulas 8 to 10, L is selected from the following structures;

R ₁₀₀ is hydrogen or substituted or unsubstituted (C1-C30) alkyl; R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ are each independently hydrogen, deuterium, halogen, halogen substituted or unsubstituted (C1-C30) alkyl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₂₀ to R ₁₂₃ form a fusion ring adjacent to each other to form quinoline; R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C1-C30) aryl; When R ₁₂₄ to R ₁₂₇ is an aryl group, fluorine can be formed by forming a fused ring with an adjacent group; R ₂₀₁ to R ₂₁₁ are each independently hydrogen, deuterium, halogen, or halogen substituted or unsubstituted (C1-C30) alkyl; o and p are each independently integers of 1 to 3, and when o or p are each an integer of 2 or more, each of R ₁₀₀ may be the same or different from each other; d is an integer of 1 to 3.

Specific examples of the phosphorescent dopant material are as follows.

The present invention further provides a composition for producing an organic electroluminescent device. The composition comprises a compound of the present invention as a host material or hole transport layer material.

In addition, the organic electroluminescent device of the present invention comprises a first electrode; Second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer may include the organic electroluminescent device composition of the present invention.

The organic electroluminescent device of the present invention includes an organic electroluminescent compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.

In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic electroluminescent compound of Chemical Formula 1, Group 1, Group 2, 4-cycle, 5-cycle transition metal, lanthanum series metal and organic metal of d-transition element One or more metal or complex compounds selected from the group may be further included, and further, the organic material layer may further include a light emitting layer and a charge generating layer.

In addition, the organic material layer may simultaneously include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic electroluminescent compound to form an organic light emitting device that emits white light.

In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a halogenated metal layer and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. Specifically, it is preferable to dispose a chalcogenide (containing oxide) layer of a metal of silicon and aluminum on the anode surface of the light emitting medium layer side and a metal halide or metal oxide layer on the cathode surface of the light emitting medium layer side. Do. This can stabilize driving. Preferred examples of the chalcogenide include SiO _X (1 ≦ _X ≦ ₂ ), AlO _X (1 ≦ _X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

For the formation of each layer of the organic light emitting device of the present invention, any one of a dry film forming method such as vacuum deposition, sputtering, plasma and ion plating, or a wet film forming method such as spin coating, dipping and flow coating can be applied. .

In the case of the wet film forming method, a thin film is formed by dissolving or dispersing the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, and the like, provided that the solvent is one in which the material of each layer is dissolved or dispersed. Any may be sufficient.

Hereinafter, for the detailed understanding of the present invention, the organic electroluminescent compound according to the present invention, a method for preparing the same, and the light emission characteristics of the device will be described.

Example 1 Preparation of Compound C-1

Preparation of Compound 1-1

Into the reaction vessel, compound 6-bromoindanone (50 g, 237 mmol), phthalaldehyde (35 g, 261 mmol) and 600 mL of ethyl alcohol were added and refluxed for 3 hours. The reaction solution was cooled to 0 ° C., and the precipitated solid was filtered and washed with cold methyl alcohol to obtain compound 1-1 (47 g, 64%).

Preparation of Compound 1-2

Iodine (13.5 g, 53.2 mmol), hypophosphoric acid (25 mL, 243 mmol, 50% aqueous solution) and acetic acid 800 mL were added to the reaction vessel, and the mixture was stirred at 100 ° C. for 30 minutes. Compound 1-1 was slowly added dropwise thereto, followed by stirring overnight. The reaction solution was cooled to room temperature, and the precipitated solid was filtered and washed with cold methyl alcohol to obtain compound 1-2 (41.5 g, 92%).

Preparation of Compound 1-3

Compound 1-2 (39 g, 132 mmol), potassium hydroxide (37 g, 660 mmol), potassium iodide (2.2 g, 13.3 mmol), benzyltriethylammonium chloride (1.5 g, 6.6 mmol), distilled water 700 mL, dimethyl sulfoxide in a reaction vessel 700 mL was added and stirred at room temperature for 15 minutes. Methyl iodide (37 g, 330 mmol) was added thereto and stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate and washed with distilled water. The extracted organic layer was dried over magnesium sulfate and the solvent was removed with a rotary evaporator. Then purified by column chromatography to give compound 1-3 (33 g, 77%).

Preparation of Compound C-1

Compound 1-3 (10 g, 31 mmol), dibiphenyl-4-ylamine (9.9 g, 31 mmol), palladium (II) acetate (0.25 g, 1.24 mmol), tri-t-butylphosphine (1 mL) in the reaction vessel , 3.1 mmol 50% xylene solution), sodium t-butoxide 4.5 g (46.5 mmol), and 150 mL of o-xylene were added and refluxed for 1 hour. The reaction solution cooled to room temperature was diluted with ethyl acetate and washed several times with water. Water was removed with anhydrous magnesium sulfate. Distillation under reduced pressure and purification by column chromatography gave Compound C-1 (9.6 g, 55%). Physical properties of compound C-1 are shown in Table 1 below.

Example 2 Preparation of Compound C-43

Preparation of Compound 2-1

Compound 2-1 was prepared by proceeding in the same manner as in the synthesis of 1-1 to 1-3 of Example 1, except that 5-bromoindanone was used instead of 6-bromoindanone.

Preparation of Compound C-43

Compound 2-1 (10 g, 31 mmol), dibiphenyl-4-ylamine (9.9 g, 31 mmol), palladium (II) acetate (0.25 g, 1.24 mmol), tri-t-butylphosphine (1 mL) in the reaction vessel , 3.1 mmol 50% xylene solution), sodium t-butoxide (4.5 g, 46.5 mmol) and 150 mL of o-xylene were added and refluxed for 1 hour. The reaction solution cooled to room temperature was diluted with ethyl acetate and washed several times with water. Water was removed with anhydrous magnesium sulfate. Distillation under reduced pressure and purification by column chromatography gave Compound C-43 (10.8 g, 62%). Physical properties of compound C-43 are shown in Table 1 below.

Example 3 Preparation of Compound C-71

Preparation of Compound 3-1

11H-benzo [b] fluorene-11-one (41.5 g, 181 mmol) and tetrahydrofuran 550 mL were added to the reaction vessel, and the reaction solution was cooled to 0 ° C. to phenylmagnesium bromide (78 mL, 235 mmol, 3M diethyl ether). Solution) was slowly added dropwise. The reaction solution was stirred at room temperature for 1 hour. The reaction was sorted with an aqueous solution of ammonium chloride, diluted with ethyl acetate, and washed with water. Water was removed with anhydrous magnesium sulfate. Distillation under reduced pressure and purification by column chromatography to give the compound 3-1 (56g, 99%).

Preparation of Compound 3-2

Compound 3-1 (28 g, 90.3 mmol), 4-bromotriphenylamine (88 g, 271 mmol) and methylene chloride (MC) (600 mL) were added to a reaction vessel, and nitrogen conditions were prepared. 3 mL of Eaton's reagent was slowly added dropwise. After stirring for 2 hours at room temperature, distilled water was added to terminate the reaction, and extracted with methylene chloride. The extracted organic layer was dried over magnesium sulfate and the solvent was removed with a rotary evaporator. Then purified by column chromatography to give compound 3-2 (38.9 g, 70%).

Preparation of Compound C-71

Compound 3-2 (10 g, 16.27 mmol), 2-naphthylboronic acid (3.4 g, 19.5 mmol), tetrakis (triphenylphosphine) palladium (0.7 g, 0.65 mmol), potassium carbonate (5.6) g, 40.7 mmol), 60 mL of toluene and 20 mL of ethanol were added thereto, and 20 ml of distilled water was added thereto, followed by stirring at 120 ° C for 3 hours. After the reaction, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed with a rotary evaporator. Then purified by column chromatography to give the compound C-71 (7.6 g, 71%). Physical properties of compound C-71 are shown in Table 1 below.

Example 4 Preparation of Compound C-89

Preparation of Compound C-89

Compound 1-3 (5 g, 15.4 mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (6.6 g, 16.2 mmol), copper iodide (1.47 g, 7.73 mmol), Diaminocyclohexane (3.7mL, 30.9mmol), potassium phosphate (9.85g, 46.4 mmol) and 100 mL of o-xylene were added and refluxed for 2 hours. The reaction solution cooled to room temperature was diluted with ethyl acetate and washed several times with water. Water was removed with anhydrous magnesium sulfate. Distillation under reduced pressure and purification by column chromatography gave 4.8 g (47%) of C-89. Physical properties of compound C-89 are shown in Table 1 below.

Example 5 Preparation of Compound C-125

Preparation of Compound 5-1

Dibenzofuran (21 g, 127 mmol) and tetrahydrofuran 330 mL were added to the reaction vessel, nitrogen was made, and the temperature was decreased to -78 ° C. To this was slowly added 50 mL (2.5 M, 115 mmol) of n-butyllithium. After stirring at −78 ° C. for 2 hours, 11H-benzo [B] fluorene-11-one (26 g, 115 mmol) dissolved in 330 mL of tetrahydrofuran was slowly added dropwise. After the dropwise addition, the reaction temperature was gradually raised to room temperature and stirred overnight. After the reaction, an ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, and extracted with methylene chloride (MC). The organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain a compound 5-1 (44 g, 96%).

Preparation of Compound 5-2

Compound 5-1 (44 g, 110 mmol), 4-bromotriphenylamine (89 g, 276 mmol) and 550 mL of methylene chloride (MC) were added to the reaction vessel, and the temperature was reduced to 0 ° C. Etons catalyst (2.4 ml, 2.2 mmol) was added thereto, and the reaction temperature was raised to room temperature. After further stirring for 3 hours, an aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with methylene chloride (MC). The organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain a compound 5-2 (55 g, 71%).

compound C-125 Manufacture

Compound 5-2 (10 g, 14.1 mmol), 2-naphthalenylboronic acid (2.6 g, 15.6 mmol), tetrakis (triphenylphosphine) palladium (0.8 g, 0.71 mmol), potassium carbonate ( 4.7 g, 34.1 mmol), 70 mL of toluene and 17 mL of ethanol were added thereto, and 17 ml of distilled water was added thereto, followed by stirring at 120 ° C for 3 hours. After the reaction was washed with distilled water and the organic layer was extracted with methylene chloride (MC). The extracted organic layer was dried over magnesium sulfate and the solvent was removed with a rotary evaporator. Then purified by column chromatography to give the compound C-125 (8.4 g, 80%). Physical properties of compound C-125 are shown in Table 1 below.

[Production Example 1] Fabrication of OLED Device Using Organic Electroluminescent Compound According to the Present Invention

An OLED device having a structure using the light emitting material of the present invention was produced. First, the transparent electrode ITO thin film (10 microseconds / square) obtained from the glass for OLED (made by GeoMatec) was ultrasonically cleaned using acetone and isopropane alcohol sequentially, and after putting into the iso propane alcohol and storing it. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N1, N1 '-([1,1'-biphenyl] -4,4'-diyl) bis (N1- ( Naphthalen-1-yl) -N4, N4-diphenylbenzene-1,4-diamine) was added and evacuated until the vacuum in the chamber reached 10E ^-6 torr. A hole injection layer having a thickness of 60 nm was deposited thereon. Subsequently, C-1 was put into another cell in the vacuum deposition equipment, and a 20 nm-thick hole transport layer was deposited on the hole injection layer by applying a current to the cell and evaporating it. After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. In one cell of the vacuum deposition equipment, compound H-1 shown in Table 2 below was added as a host, and D-1 was added as a dopant in another cell, and then the two materials were evaporated at different rates to form the entire host and dopant. The light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping the dopant to 15% by weight. Subsequently, one cell as the electron transporting layer on the light emitting layer, followed by 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1 in one cell as the electron transporting layer on the light emitting layer -Phenyl-1H-benzo [d] imidazole was added, and another cell was charged with lithium quinolate, and the two materials were evaporated at the same rate to be doped at 50% by weight to deposit an electron transport layer of 30 nm. Subsequently, lithium quinolate was deposited to a thickness of 2 nm with an electron injection layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition apparatus to manufacture an OLED device. Each compound was used by vacuum sublimation purification under 10E- ⁶ torr.

As a result, a current of 3.5 mA / cm ² flowed, and green light emission of 1500 cd / m ² was confirmed.

Device Preparation Example 2 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

C-71 is used as the hole transport layer and as the host An OLED device was manufactured according to the same method as Example 1 except for using the compounds H-2 and H-3 of the following [Table 2].

As a result, a current of 14.0 mA / cm ² flowed, and blue light emission of 700 cd / m ² was confirmed.

Device Preparation Example 3 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that C-89 was deposited to a thickness of 20 nm as the hole transport layer.

As a result, 1.9 mA / cm ² of current flowed, and green light emission of 900 cd / m ² was confirmed.

Device Fabrication Example 4 OLED Device Fabrication Using Organic Light Emitting Compound According to the Present Invention

An OLED device was manufactured in the same manner as in Example 1, except that C-125 was used as the hole transport layer and H-2 and H-3 were used as the host.

As a result, a current of 25.0 mA / cm ² flowed, and blue light emission of 1200 cd / m ² was confirmed.

Comparative Example 1 Fabrication of OLED Device Using Conventional Light-Emitting Material

An OLED device was manufactured in the same manner as in Example 1, except that Compound T-1 of the following [Table 2] was deposited to a thickness of 20 nm as the hole transport layer.

As a result, a current of 26.1 mA / cm ² flowed, and green light emission of 9800 cd / m ² was confirmed.

 Comparative Example 2 Fabrication of OLED Device Using Conventional Light-Emitting Material

An OLED device was manufactured in the same manner as in Example 1, except that T-1 was used as the hole transport layer and H-2 and H-3 were used as the host.

As a result, a current of 141.2 mA / cm ² flowed, and blue light emission of 2800 cd / m ² was confirmed.

 It was confirmed that the luminescent properties of the compounds for organic electronic materials developed in the present invention showed superior characteristics compared to the conventional materials. In addition, the device using the compound for an organic electronic material according to the present invention is excellent in light emission characteristics and good life characteristics.

Claims (7)

An organic electroluminescent compound represented by Formula 1 below.
[Formula 1]

In Chemical Formula 1,
Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, wherein Ar ₁ and Ar ₂ are fused to be substituted or not provided. Form a substituted carbazole ring, or at least one of Ar ₁ and Ar ₂ is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, dibenzofuranyl or dibenzothiophene (C6-C30) aryl substituted with one or (5- to 30-membered) heteroaryl substituted with dibenzofuranyl or dibenzothiophenyl;
Ar ₅ is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl;
L ₁ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;
L ₂ is substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5- to 30-membered) heteroarylene;
Each R ₁ is independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -N (R ₁₁ ) (R ₁₂ ), —Si (R ₁₃ ) (R ₁₄ ) (R ₁₅ ), —S (R ₁₆ ), —O (R ₁₇ ), cyano, nitro, or hydroxy; May be linked to an adjacent substituent to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic rings are replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;
Each R ₂ is independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -N (R ₁₁ ) (R ₁₂ ), —Si (R ₁₃ ) (R ₁₄ ) (R ₁₅ ), —S (R ₁₆ ), —O (R ₁₇ ), cyano, nitro, or hydroxy;
R ₁₁ to R ₁₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; May be linked to an adjacent substituent to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic ring are one or more heteroatoms selected from nitrogen, oxygen and sulfur. May be substituted;
n and m are each independently an integer of 0 to 1, provided that when n and m cannot be 0 at the same time, n is 0 and m is 1, at least one of R ₁ and R ₂ is hydrogen or deuterium Not;
a is an integer of 1 to 3, and when a is an integer of 2 or more, each R ₁ may be the same or different;
b is an integer from 1 to 6, and when b is an integer of 2 or more, each R ₂ may be the same or different;
The heteroaryl (ene) comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;
The heterocycloalkyl includes one or more heteroatoms selected from O, S and N. The method of claim 1, wherein in Ar ₁ to Ar ₅ , L ₁ , L ₂ , R ₁ , R ₂ , and R ₁₁ to R ₁₇ , substituted alkyl (lene), substituted aryl (lene), substituted heteroaryl (lene), Substituents of substituted cycloalkyl, substituted heterocycloalkyl, and substituted aralkyl are each independently (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl unsubstituted or substituted with deuterium, halogen, or halogen. (3-30 membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30 Alkynyl, cyano, di (C1-C30) alkylamino, di (C6-C30) arylamino unsubstituted or substituted with (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) arylamino , Di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) Alkyl, di (C1-C30) alkyl (C6- C30) at least one organic electroluminescent compound selected from the group consisting of aryl, carboxyl, nitro and hydroxy. The organic electroluminescent compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, Ar ₁ to Ar ₅ , L ₁ , L ₂ , R ₁ , R ₂ , a and b are the same as defined in claim 1. The compound of claim 1, wherein Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5- to 21-membered) heteroaryl, wherein Ar ₁ and Ar ₂ are fused to each other. To form a substituted or unsubstituted carbazole ring, or at least one of Ar ₁ and Ar ₂ is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, dibenzofuranyl or (C6-C21) aryl substituted with dibenzothiophenyl or (5-21 membered) heteroaryl substituted with dibenzofuranyl or dibenzothiophenyl;
Ar ₅ is substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, or substituted or unsubstituted (5-21 membered) heteroaryl;
L ₁ is a single bond, a substituted or unsubstituted (C1-C21) arylene, or a substituted or unsubstituted (5-21 membered) heteroarylene;
L ₂ is substituted or unsubstituted (C1-C20) alkylene, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5-21 membered) heteroarylene;
R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-21 membered) heteroaryl, Or -N (R ₁₁ ) (R ₁₂ );
R ₁₁ and R ₁₂ are each independently a substituted or unsubstituted (C6-C21) aryl;
N and m are each independently an integer of 0 to 1, provided that when n and m cannot be 0 at the same time, n is 0 and m is 1, at least one of R ₁ and R ₂ is hydrogen Not;
A is an integer of 1 to 3, and when a is an integer of 2 or more, each R ₁ may be the same or different;
B is an integer from 1 to 6, and when b is an integer of 2 or more, each R ₂ may be the same or different;
Wherein said heteroaryl (ene) comprises one or more heteroatoms selected from N, O and S. The compound of claim 1, wherein Ar ₁ to Ar ₄ are substituted or unsubstituted (C6-C21) aryl, wherein the substituent of (C6-C21) aryl is (C1-C30) alkyl, (C1-C10) alkyl It may be at least one selected from the group consisting of (C6-C21) aryl unsubstituted or substituted with (C6-C12) aryl, and (5-21 membered) heteroaryl unsubstituted or substituted with, wherein Ar ₁ and Ar ₂ is fused to form a substituted or unsubstituted carbazole ring, or at least one of Ar ₁ and Ar ₂ is (C6-C21) aryl substituted with dibenzofuranyl or dibenzothiophenyl;
Ar ₅ is unsubstituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, (6-21 membered) heteroaryl or di (C6-C18) arylamino; Or (6-21) membered heteroaryl unsubstituted or substituted with (C1-C10) alkyl or (C6-C18) aryl, including heteroatoms selected from N, O and S;
L ₁ is a single bond; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; Or a (5- to 18-membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl containing a nitrogen atom as a heteroatom;
L ₂ is unsubstituted (C1-C10) alkylene; (C6-C18) arylene unsubstituted or substituted with (C1-C10) alkyl; Or (6-21 membered) heteroarylene unsubstituted or substituted with a (C1-C10) alkyl containing an oxygen atom as a heteroatom;
R ₁ and R ₂ are each independently hydrogen; Unsubstituted (C6-C18) aryl; Unsubstituted (6- to 18-membered) heteroaryl containing a nitrogen atom as a hetero atom; Or -N (R ₁₁ ) (R ₁₂ );
R ₁₁ and R ₁₂ are each independently unsubstituted (C6-C18) aryl;
N and m are each independently an integer of 0 to 1, provided that when n and m cannot be 0 at the same time, n is 0 and m is 1, at least one of R ₁ and R ₂ is hydrogen Not;
A is 1;
B is 1, the organic electroluminescent compound. The organic electroluminescent compound of claim 1, wherein the compound represented by Chemical Formula 1 is selected from the group consisting of the following compounds.

The organic electroluminescent element containing the organic electroluminescent compound of Claim 1.

Images