KR102192497B1 - 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 including the same. When the organic electroluminescent compound of the present invention is used, an organic electroluminescent device having excellent current efficiency and light emission efficiency can be manufactured.

Description

An organic electroluminescent compound and an organic electroluminescent device comprising the same

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

Among display devices, an electroluminescent device (EL device) is a self-luminous display device and has an advantage in that it has a wide viewing angle, excellent contrast, and a high response speed. In 1987, Eastman Kodak Co., Ltd. first developed an organic EL device using a low-molecular aromatic diamine and aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining luminous efficiency in an organic electroluminescent device is a light-emitting material. Fluorescent materials have been widely used as luminescent materials until now. However, due to the mechanism of electroluminescence, phosphorescent luminescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescent materials. Has become. Until now, iridium (III) complex series are widely known as phosphorescent materials, and for each RGB, bis(2-(2'-benzothienyl)-pyridinato-N,C-3') iridium (acetylacetonate ) [(acac)Ir(btp) ₂ ], tris(2-phenylpyridine)iridium [Ir(ppy) ₃ ] and bis(4,6-difluorophenylpyridinato-N,C2)picolinei Materials such as toiridium (Firpic) are known.

In the prior art, 4,4'-N,N'-dicarbazole-biphenyl (CBP) was most widely known as a host material for phosphorescence. Recently, Bathocuproine (BCP) and aluminum (III) bis(2-methyl-8-quinolinate) (4-phenylphenolate), which were used as materials for hole blocking layers by Japanese pioneers and the like Balq) has been used as a host material to develop high-performance organic electroluminescent devices.

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

Meanwhile, the organic electroluminescent device has a multilayer 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. In this case, 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 lifetime 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 materials 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), etc. have been used, but when these materials are used, the quantum efficiency and lifetime of the organic electroluminescent device are deteriorated, because when the organic electroluminescent device is driven at a high current, , This is because a thermal stress occurs between the anode and the hole injection layer, and the life of the device is drastically reduced by this thermal stress, and the organic material used for the hole injection layer has very high hole mobility. Therefore, the hole-electron charge balance is broken, and the quantum efficiency (cd/A) is lowered.

Korean Patent Publication No. KR 2012-0029446, International Publication No. WO 2013-065589, and International Publication No. WO 2007-119800 disclose an amine derivative having a benzofluorene-based substituent as a compound for an organic electroluminescent device. .

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

Korean Patent Application Publication KR 2012-0029446 A (published on March 26, 2012) International Patent Publication WO 2013-065589 A1 (published on May 10, 2013) International Patent Publication WO 2007-119800 A1 (published on October 25, 2007)

An object of the present invention is to provide an organic electroluminescent compound having excellent current efficiency and light emission efficiency, and an organic electroluminescent device including the same.

As a result of intensive research in order to solve the above technical problem, the present inventors have completed the present invention by discovering that the organic electroluminescent compound represented by the following formula (1) achieves the above object.

[Formula 1]

In Formula 1,

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-30 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 (5-30 membered)heteroaryl;

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

L ₂ is a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5-30 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 (5-30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl,- Is N(R ₁₁ )(R ₁₂ ), -Si(R ₁₃ )(R ₁₄ )(R ₁₅ ), -S(R ₁₆ ), -O(R ₁₇ ), cyano, nitro, or hydroxy; It is connected with an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is replaced by 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 membered) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; It is connected with an adjacent substituent to form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is one or more heteroatoms selected from nitrogen, oxygen, and sulfur. Can 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 of 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) includes one or more heteroatoms selected from B, N, O, S, P(=O), 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 being able to manufacture an organic electroluminescent device having excellent current efficiency and light emission efficiency.

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

Hereinafter, the present invention will be described in more detail, but this is for illustration 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.

The organic electroluminescent compound represented by Formula 1 will be described in more detail as follows.

Specific examples of "alkyl" described in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As specific examples of "alkenyl" herein, 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, and at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, Preferably, it means a cycloalkyl containing one or more heteroatoms selected from O, S and N, and examples include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran. As used herein, "aryl (ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon, for example, phenyl, biphenyl, terphenyl, naphthyl, binapthyl, phenylnaphthyl, naphthylphenyl, flu Orenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl, chrysenyl , Naphthacenyl, and fluoranthenyl. In the present application, "(5-30 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(=O), Si and P It means an aryl group containing an atom. 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 includes a form in which one or more heteroaryl or aryl groups are linked 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 , Triazolyl, tetrazolyl, furazanyl, pyridyl, bipyridyl, pyrazinyl, pyrimidyl, and single ring heteroaryl such as pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuran Il, dibenzothiophenyl, naphthofuranyl, naphthothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxa Zolyl, isoindoleyl, indolyl, indolinyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazyl, phenanthridinyl, And fused ring heteroaryl such as benzodioxolyl. "Halogen" herein includes F, Cl, Br and I atoms.

In the description of "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. 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 (ene), substituted aryl (ene), substituted heteroaryl (ene), substituted The substituents of cycloalkyl, substituted heterocycloalkyl, and substituted aralkyl are each independently deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl, (C6-C30) aryl substituted or unsubstituted (3-30 membered) heteroaryl, (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)aryl, carboxyl, nitro and hydroxy, and each independently (C1-C30)alkyl, (C6-C21)aryl , (C6-C12) aryl substituted or unsubstituted (5-21 membered) heteroaryl, and di(C6-C21) arylamino is preferably at least one selected from the group consisting of.

According to an aspect of the present invention, the compound represented by Formula 1 may be represented by any one of the following Formulas 2 to 4, and 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 a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, and Ar ₁ and Ar ₂ Can fuse to form a ring; Preferably substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5-21 membered) heteroaryl, and 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 the (C6-C21)aryl is (C1-C30)alkyl, (C1-C10)alkyl substituted or unsubstituted (C6 -C21) aryl, and (C6-C12) aryl substituted or unsubstituted (5-21 membered) may be one or more selected from the group consisting of heteroaryl, Ar ₁ and Ar ₂ may be fused to form a ring have. Specifically, Ar ₁ to Ar ₄ may each independently be phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or benzofluorenyl, and these are each 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, and Ar ₁ and Ar ₂ may be fused to form a ring.

Ar ₅ is a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-30 membered)heteroaryl; Preferably, they are 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 it may be a (6-21) membered heteroaryl unsubstituted or substituted with (C1-C10)alkyl or (C6-C18)aryl containing a heteroatom 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; It may be substituted or unsubstituted with phenyl, carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, or dibenzofuranyl.

L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene; Preferably, they are 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 (5-18 membered) heteroarylene which contains a nitrogen atom as a hetero atom and is unsubstituted or substituted with (C1-C10)alkyl. Specifically, L ₁ is a single bond, phenyl or pyrimidyl.

L ₂ is a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene; Preferably, they are 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 which contains an oxygen atom as a hetero atom and is unsubstituted or substituted with (C1-C10)alkyl. Specifically, L ₂ is (C1-C4) alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, or dibenzofuranyl.

The 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 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, or It is connected with an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur. Can be; The 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 membered ) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; It is connected with an adjacent substituent to form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is 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 ), and R ₁₁ and R ₁₂ are each independently substituted or unsubstituted (C6-C21)aryl. More preferably, R ₁ and R ₂ are each independently hydrogen; Unsubstituted (C6-C18)aryl; Unsubstituted (6-18 membered) heteroaryl containing a nitrogen atom as a heteroatom; 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.

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

Wherein 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 of 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 a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a 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 a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5-21 membered) heteroarylene; The R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C21) aryl, a 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; Wherein 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 of 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) includes 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 (C6-C21) aryl substituent is (C1 -C30) alkyl, (C1-C10) alkyl substituted or unsubstituted (C6-C21) aryl, and (C6-C12) aryl substituted or unsubstituted (5-21 membered) selected from the group consisting of heteroaryl May be one or more, and 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 it may be a (6-21) membered heteroaryl unsubstituted or substituted with (C1-C10)alkyl or (C6-C18)aryl containing a heteroatom selected from N, O and S; L ₁ is a single bond; (C6-C18)arylene unsubstituted or substituted with (C1-C10)alkyl; Or (5-18 membered) heteroarylene which contains a nitrogen atom as a heteroatom and is unsubstituted or substituted with (C1-C10)alkyl; L ₂ is unsubstituted (C1-C10)alkylene; (C6-C18)arylene unsubstituted or substituted with (C1-C10)alkyl; Or (6-21 membered) heteroarylene which contains an oxygen atom as a hetero atom and is substituted or unsubstituted with (C1-C10)alkyl; R ₁ and R ₂ are each independently hydrogen; Unsubstituted (C6-C18)aryl; Unsubstituted (6-18 membered) heteroaryl containing a nitrogen atom as a heteroatom; 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 Formula 1 may be more specifically exemplified as the following compounds, but is not limited thereto.

The organic electroluminescent compound according to the present invention may be prepared by a synthesis method known to those skilled in the art, for example, as shown in Schemes 1 and 2 below.

[Scheme 1]

[Scheme 2]

In addition, the present invention provides an organic electroluminescent material comprising the 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, or may further include conventional materials included in the organic electroluminescent material.

The organic electroluminescent device according to the present invention comprises: a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, and the organic material layer may include one or more organic electroluminescent compounds of Formula 1 above.

One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer includes an emission layer, and may further include at least one layer 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 emission 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 contain a known light-emitting material or contain 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 emission layer, one or more dopants may be further included therein. Further, a second host material may be further included, and in this case, a weight ratio of the first host material and the second host material is in the range of 1:99 to 99:1.

As the known host material or the second host material, it is particularly preferable in terms of luminous efficiency to be selected from the group consisting of compounds represented by the following formulas 5 to 7.

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 3 to 5,

Cz is 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 (3-30 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 (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-30 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 at the same time; R ₃₁ to R ₃₃ are each independently a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (5-30 membered) heteroaryl, and R ₃₂ And R ₃₃ may 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, each (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.

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

The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following Chemical Formulas 8 to 10.

[Formula 8]

[Formula 9]

[Formula 10]

In 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 may form a fused ring between adjacent substituents 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 are an aryl group, fluorene 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 an integer of 1 to 3, and when o or p is an integer of 2 or more, each R ₁₀₀ may be the same as or different from each other; d is an integer of 1 to 3.

A specific example of the phosphorescent dopant material is as follows.

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

In addition, the organic electroluminescent device of the present invention includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, the organic material layer including an emission layer, and the emission layer may include the composition for an organic electroluminescent device of the present invention.

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

In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic electroluminescent compound of Formula 1, a group 1, group 2, period 4, period 5 transition metal, a lanthanide metal, and an organic metal of a d-transition element One or more metals or complex compounds selected from the group may be further included, and further, the organic material layer may further include an emission layer and a charge generation layer.

In addition, the organic material layer may simultaneously include at least one organic light emitting layer including a blue, red, or green light emitting compound in addition to the organic EL compound to form an organic EL device emitting white light.

In the organic electroluminescent device of the present invention, on at least one inner surface of a pair of electrodes, a single layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as “surface layer”) It is preferable to arrange the above. Specifically, it is preferable to arrange a chalcogenide (including oxide) layer of metals of silicon and aluminum on the anode surface on the side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer on the surface of the cathode on the side of the light-emitting medium layer. Do. This makes it possible to achieve stabilization of 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 metal halide include LiF, MgF ₂ , CaF ₂ , fluoride Rare earth metals and the like, and preferred examples of metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In addition, in the organic electroluminescent device of the present invention, it is also possible to arrange a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant on at least one surface of the pair of electrodes thus prepared. desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it becomes easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferable 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 can be manufactured by using the reducing dopant layer as a charge generation layer.

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

In the case of the wet film formation 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, etc., provided that the material of each layer is dissolved or dispersed. It can be either.

Hereinafter, for a detailed understanding of the present invention, an organic electroluminescent compound according to the present invention, a method of manufacturing the same, and luminescence characteristics of the device will be described with reference to the representative compound of the present invention.

[Example 1] Preparation of Compound C-1

Preparation of compound 1-1

Compound 6-bromoindanone (50 g, 237 mmol), phthalaldehyde (35 g, 261 mmol) and 600 mL of ethyl alcohol were added to the reaction vessel and refluxed for 3 hours. The reaction solution was cooled to 0°C, 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), hypophosphorous acid (25 mL, 243 mmol, 50% aqueous solution), and 800 mL of acetic acid were added to the reaction vessel, followed by stirring 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, the precipitated solid was filtered, and washed with cold methyl alcohol to obtain compound 1-2 (41.5g, 92%).

Preparation of compound 1-3

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

Preparation of compound C-1

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

In the reaction vessel, compound 2-1 (10g, 31 mmol), dibiphenyl-4-ylamine (9.9g, 31mmol), palladium(II) acetate (0.25g, 1.24mmol), tri-t-butylphosphine (1mL) , 3.1mmol 50% xylene solution), sodium t-butoxide (4.5g, 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. Moisture was removed with anhydrous magnesium sulfate. Distilled under reduced pressure and purified by column chromatography to obtain compound C-43 (10.8g, 62%). The 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]fluoren-11-one (41.5 g, 181 mmol) and 550 mL of tetrahydrofuran were added to the reaction vessel, and the reaction solution was cooled to 0° C. to obtain 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 ammonium chloride solution, diluted with ethyl acetate, and washed with water. Moisture was removed with anhydrous magnesium sulfate. Distilled under reduced pressure and purified by column chromatography to obtain 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 the reaction vessel, and nitrogen conditions were made. 3 mL of Eaton's reagent was slowly added dropwise. After stirring at room temperature for 2 hours, distilled water was added to terminate the reaction, followed by extraction with methylene chloride. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. After that, it was purified by column chromatography to obtain compound 3-2 (38.9 g, 70%).

Preparation of compound C-71

In the reaction vessel, 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, and 20 mL of distilled water was added, followed by stirring at 120? for 3 hours. After the reaction was completed, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Then, it was purified by column chromatography to obtain compound C-71 (7.6 g, 71%). The physical properties of Compound C-71 are shown in Table 1 below.

[Example 4] Preparation of Compound C-89

Preparation of compound C-89

In the reaction vessel, compound 1-3 (5g, 15.4 mmol), 9-phenyl-9H,9'H-3,3'-bicarbazole (6.6g, 16.2mmol), copper iodide (1.47 g, 7.73mmol), Diaminocyclohexane (3.7 mL, 30.9 mmol), potassium phosphate (9.85 g, 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. Moisture was removed with anhydrous magnesium sulfate. Distilled under reduced pressure and purified by column chromatography to obtain 4.8 g (47%) of C-89. The 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 330 mL of tetrahydrofuran were added to the reaction vessel, and the temperature was lowered to -78°C after making nitrogen conditions. 50 mL (2.5 M, 115 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring at -78°C for 2 hours, 11H-benzo[B]fluoren-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. When the reaction was completed, 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, the solvent was removed by a rotary evaporator, and purified by column chromatography to obtain 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 lowered to 0°C. Etons catalyst (2.4 ml, 2.2 mmol) was added thereto, and the reaction temperature was raised to room temperature. After stirring for an additional 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 by a rotary evaporator and purified by column chromatography to obtain compound 5-2 (55 g, 71%).

compound C-125 Manufacture of

In the reaction vessel, 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, and 17 ml of distilled water was added, followed by stirring at 120? for 3 hours. After the reaction was completed, the mixture was washed with distilled water and the organic layer was extracted with methylene chloride (MC). After drying the extracted organic layer with magnesium sulfate, the solvent was removed by a rotary evaporator. After that, it was purified by column chromatography to obtain compound C-125 (8.4 g, 80%). The physical properties of Compound C-125 are shown in Table 1 below.

[Device Example 1] Fabrication of an OLED device using the organic electroluminescent compound according to the present invention

An OLED device having a structure using the light emitting material of the present invention was manufactured. First, the transparent electrode ITO thin film (10Ω/□) obtained from OLED glass (manufactured by Geomatech) was subjected to ultrasonic cleaning by sequentially using acetone and isopropane alcohol, and then stored in isopropane alcohol and used. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, 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 degree of vacuum in the chamber reached 10E ^-6 torr, and then the cell was evaporated by applying a current to the ITO substrate. A hole injection layer having a thickness of 60 nm was deposited thereon. Subsequently, C-1 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. In one cell of the vacuum evaporation equipment, compound H-1 of the following [Table 2] was put as a host, and D-1 as a dopant was added to the other cell, and then the two materials were evaporated at different rates to form the host and the entire dopant. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping with a dopant of 15% by weight. Then, in one cell as an electron transport layer on the light-emitting layer, and then in one cell as an electron transport layer on the light-emitting layer, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1 -Phenyl-1H-benzo[d]imidazole was added, and lithium quinolate was added to another cell, and then the two materials were evaporated at the same rate and doped with 50% weight to deposit an electron transport layer of 30 nm. Subsequently, lithium quinolate was deposited to a thickness of 2 nm as an electron injection layer, and then an Al anode was deposited to a thickness of 150 nm using another vacuum deposition equipment to fabricate an OLED device. For each material, 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 Example 2] Fabrication of an OLED device using the organic light emitting compound according to the present invention

Use C-71 as the hole transport layer and as a host An OLED device was manufactured in the same manner as in Example 1, except that the compounds H-2 and H-3 of Table 2 were used.

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

[Device Example 3] Fabrication of an OLED device using the 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 a hole transport layer.

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

[Device Example 4] Fabrication of an OLED device using the 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 hosts.

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 devices using conventional light emitting materials

An OLED device was manufactured in the same manner as in Example 1, except that the compound T-1 of Table 2 below was deposited to a thickness of 20 nm as a 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 devices using conventional light emitting materials

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 hosts.

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 luminous properties of the compounds for organic electronic materials developed in the present invention exhibit superior properties compared to conventional materials. In addition, the device using the compound for an organic electronic material according to the present invention has excellent light emitting characteristics and good lifespan characteristics.

Claims (7)

An organic electroluminescent compound represented by the following formula (1).
[Formula 1]

In Formula 1,
Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, wherein at least one of Ar ₁ and Ar ₂ is substituted or Unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, (C6-C30)aryl substituted with dibenzofuranyl or dibenzothiophenyl, dibenzofuranyl or dibenzothiophene Substituted with one (5-30 membered) heteroaryl, or Ar ₁ and Ar ₂ are each substituted or unsubstituted (C6)aryl, and they are linked to each other to form a substituted or unsubstituted carbazole ring;
Ar ₅ is substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5-30 membered)heteroaryl;
L ₁ is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene, provided that L ₁ is a substituted or unsubstituted anthracenylene. Except for cases;
L ₂ is a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene;
R ₁ is each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 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; It is connected with an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur. Can be;
R ₂ is each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 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 (5-30 membered) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; It is connected with an adjacent substituent to form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is one or more heteroatoms selected from nitrogen, oxygen, and sulfur. Can 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, and when 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 of 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) includes at least one heteroatom selected from B, N, O, S, P(=O), Si and P;
The heterocycloalkyl includes one or more heteroatoms selected from O, S and N. The method of claim 1, wherein Ar ₁ to Ar ₅ , L ₁ , L ₂ , R ₁ , R ₂ , and R ₁₁ to R ₁₇ at substituted alkyl (ene), substituted aryl (ene), substituted heteroaryl (ene), Substituents of substituted cycloalkyl, substituted heterocycloalkyl, and substituted aralkyl are each independently deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl , (C6-C30) aryl substituted or unsubstituted (3-30 membered) heteroaryl, (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) An organic electroluminescent compound which is at least one selected from the group consisting of alkyl, di(C1-C30)alkyl(C6-C30)aryl, carboxyl, nitro and hydroxy. The organic electroluminescent compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of the following 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 method of claim 1, wherein Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5-21 membered) heteroaryl, wherein at least _one of Ar ₁ and Ar ₂ One is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, (C6-C21)aryl substituted with dibenzofuranyl or dibenzothiophenyl, or dibenzofuranyl or (5-21 membered) heteroaryl substituted with dibenzothiophenyl, or Ar ₁ and Ar ₂ are each substituted or unsubstituted (C6) aryl, and these are linked to each other to form a substituted or unsubstituted carbazole ring;
Ar ₅ is a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, or a substituted or unsubstituted (5-21 membered) heteroaryl;
Wherein L ₁ is a single bond, a substituted or unsubstituted (C1-C21) arylene, or a substituted or unsubstituted (5-21 membered) heteroarylene, provided that L ₁ is a substituted or unsubstituted anthracenylene Except where;
L ₂ is a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsubstituted (C6-C21)arylene, or a substituted or unsubstituted (5-21 membered) heteroarylene;
The R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C21) aryl, a 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;
Wherein n and m are each independently an integer of 0 to 1, provided that 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;
Wherein 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 of 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, an organic electroluminescent compound. The method 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 one or more selected from the group consisting of substituted or unsubstituted (C6-C21)aryl, and (C6-C12)aryl substituted or unsubstituted (5-21 membered) heteroaryl, and Ar ₁ and Ar ₂ At least one of them is (C6-C21)aryl substituted with dibenzofuranyl or dibenzothiophenyl, or Ar ₁ and Ar ₂ are each substituted or unsubstituted (C6)aryl, and these are linked to each other to be substituted or unsubstituted Form a carbazole 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 it may be a (6-21) membered heteroaryl unsubstituted or substituted with (C1-C10)alkyl or (C6-C18)aryl containing a heteroatom selected from N, O and S;
L ₁ is a single bond; (C6-C18)arylene unsubstituted or substituted with (C1-C10)alkyl; Or (5-18 membered) heteroarylene containing a nitrogen atom as a heteroatom and substituted or unsubstituted with (C1-C10)alkyl, provided that L ₁ is a substituted or unsubstituted anthracenylene ;
L ₂ is unsubstituted (C1-C10)alkylene; (C6-C18)arylene unsubstituted or substituted with (C1-C10)alkyl; Or (6-21 membered) heteroarylene which contains an oxygen atom as a hetero atom and is unsubstituted or substituted with (C1-C10)alkyl;
R ₁ and R ₂ are each independently hydrogen; Unsubstituted (C6-C18)aryl; Unsubstituted (6-18 membered) heteroaryl containing a nitrogen atom as a heteroatom; Or -N(R ₁₁ )(R ₁₂ );
R ₁₁ and R ₁₂ are each independently unsubstituted (C6-C18)aryl;
Wherein n and m are each independently an integer of 0 to 1, provided that 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, an organic electroluminescent compound. The organic electroluminescent compound of claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

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