KR20200101838A - 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. The organic electroluminescent device having high luminous efficiency and/or high power efficiency can be manufactured by including the organic electroluminescent compound according to the present invention.

Description

An organic electroluminescent compound and an organic electroluminescent device containing the same TECHNICAL FIELD [ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

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

An electroluminescent device (EL device) is a self-luminous display device, and has the advantage of having a wide viewing angle, excellent contrast, and fast 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 [see Appl. Phys. Lett. 51, 913, 1987].

An organic electroluminescent device is a device that converts electrical energy into light by applying electricity to an organic light-emitting material, and generally has a structure including an anode (anode) and a cathode (cathode), and an organic material layer therebetween. The organic material layer of the organic electroluminescent device is a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer (including host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, and electron injection. It may include a layer and the like. The material used for the organic material layer is a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. Can be divided. In such an organic electroluminescent device, holes are injected from the anode and electrons from the cathode to the emission layer by applying a voltage, and excitons with high energy are formed by recombination of the holes and electrons. The organic light-emitting compound is excited by this energy, and the excited state of the organic light-emitting compound returns to a ground state, and energy is emitted as light to emit light.

The luminous material of an organic electroluminescent device is the most important factor in determining the luminous efficiency of the device. The luminous material must have high quantum efficiency and high mobility of electrons and holes, and the formed light emitting material layer must be uniform and stable. These light-emitting materials are divided into blue, green, or red light-emitting materials according to the light-emitting color, and there are also yellow or orange light-emitting materials. Further, the light emitting material may be classified into a host material and a dopant material in terms of functionality. Recently, the development of high-efficiency and long-life organic electroluminescent devices has emerged as an urgent task. In particular, considering the level of EL characteristics required by medium-to-large OLED panels, it is urgent to develop materials that are very superior to existing light-emitting materials. . To this end, desirable properties of a solid solvent and a host material serving as an energy carrier must have high purity and an appropriate molecular weight to enable vacuum deposition. In addition, thermal stability must be secured due to high glass transition ionicity and thermal decomposition temperature, high electrochemical stability is required for long life, easy to form amorphous thin film, and good adhesion to materials of other adjacent layers, whereas interlayer movement is not Shouldn't.

In addition, there is a need to develop a material that has good thermal stability in a hole transport layer, a buffer layer, an electron transport layer, and the like, and can improve the performance of an organic electroluminescent device, such as driving voltage, luminous efficiency, and lifetime characteristics.

Korean Patent Publication No. 2016-0076881 discloses an example in which a condensed phenanthrene-based compound is used as an electron transport auxiliary layer and a host compound.

Korean Patent Application Publication No. 2016-0076881 (published on July 1, 2016)

An object of the present invention is to firstly provide an organic electroluminescent compound capable of manufacturing an organic electroluminescent device having high luminous efficiency and/or high power efficiency, and secondly, an organic electroluminescent compound containing the organic electroluminescent compound It is to provide the device.

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,

Y ₁ and Y ₂ are each independently O or S;

Each L ₁ is independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;

Ar ₁ is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered ) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di( C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted A fused ring group of a cyclic (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, or -N(Ar ₄ )(Ar ₅ ); Adjacent substituents may be linked to each other to form a ring;

Ar ₄ and Ar ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl , Or a substituted or unsubstituted (3-30 membered) heteroaryl;

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, Or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; Adjacent substituents may be linked to each other to form a ring;

a is an integer of 0 to 4, and when a is an integer of 2 or more, each of -L ₁ -Ar ₁ may be the same or different from each other.

By including the organic electroluminescent compound according to the present invention, an organic electroluminescent device having high luminous efficiency and/or high power efficiency can be manufactured.

1 is a representative formula of an organic electroluminescent compound according to the present application.

Hereinafter, the present application will be described in more detail, but this is for illustrative purposes and should not be construed as a way to limit the scope of the present application.

The present application 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 material.

As used herein, the "organic electroluminescent compound" refers to a compound that can be used in an organic electroluminescent device, and may be included in any material layer constituting the organic electroluminescent device, if necessary.

As used herein, "organic electroluminescent material" refers to a material that can be used for an organic electroluminescent device, may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material is a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, It may be an electron transport material, an electron injection material, or the like.

As used herein, "(C1-C30)alkyl" refers to a straight or branched chain alkyl having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, and preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(C6-C30)aryl (ene)" refers to a monocyclic or fused cyclic radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated, and includes a spiro structure. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15. As an example of the aryl, specifically, phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, binapthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, di Phenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl , Pyrenyl, tetracenyl, perylenyl, chrysenyl, benzocrycenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl ( cumenyl) spiro[fluoren-fluoren]yl, spiro[fluorene-benzofluoren]yl, azulenyl, and the like. More specifically, the aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-kumenyl Menyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl , p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluore Nyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl , 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9 -Phenanthryl, 1-Chrysenyl, 2-Chrycenyl, 3-Chrycenyl, 4-Chrysenyl, 5-Chrycenyl, 6-Chrycenyl, benzo[c]phenanthryl, benzo[g]Chrycenyl, 1- Triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl Can be mentioned.

As used herein, "(3-30 membered) heteroaryl (ene)" has 3 to 30 ring skeleton atoms, and includes one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge It means an aryl group to say, and it is preferable that the number of ring skeleton atoms is 5 to 25 here. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein includes one or more heteroaryl groups or aryl groups linked to a heteroaryl group by a single bond. Specific examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl , Tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, and monocyclic heteroaryls such as pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzo Furanyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, Benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazolyl, phenanthridinyl, benzodioc Fused ring heteroaryl such as solyl, indolizidine, acridinyl, silafluorenyl, and germaneflowrenyl. More specifically, the heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl , 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizydinyl, 2-indorizidinyl, 3-indolizedinyl, 5-indolizedinyl, 6-indolizedinyl, 7- Indolizinyl, 8-indolizinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2 -Isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3 -Benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl , 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2- Quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, aza Carbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl -8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8 -Phenantridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxa Zolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrole- 5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl -3-Indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4- t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl , 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl , 2-germafluorenyl, 3-germafluorenyl, and 4-germafluorenyl.

"Halogen" herein includes F, Cl, Br and I atoms.

In addition, "ortho (o)", "meta (m)", "para (p)" refers to the substitution position of all substituents, and the ortho position refers to a compound in which the position of the substituent is immediately adjacent. For example, in the case of benzene, it means the 1st and 2nd digits, and the meta-position represents the next substitutional position of the immediate neighboring substitutional position, for example, in the case of benzene, it means 1st and 3rd digits, and the para position Is the next substitution position of the meta position, for example, in the case of benzene, it means 1 to 4 digits.

As used herein, "a ring formed by linking with adjacent substituents" refers to a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or combination thereof formed by linking or fusion of two or more adjacent substituents. Means, and preferably, a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic, or a combination thereof may be used. In addition, the formed ring may contain one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. According to an example of the present application, the number of ring skeleton atoms is (5-20 members), and according to another example of the present application, the number of ring skeleton atoms is (5-15 members). For example, the fused ring is, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or Unsubstituted fluorene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted indole ring, substituted or unsubstituted indene ring, substituted or unsubstituted benzene ring, or It may be in the form of a substituted or unsubstituted carbazole ring.

In addition, in the description of "substituted or unsubstituted" herein, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. In the present application L ₁ , Ar ₁ , Ar ₄ , Ar ₅ , R ₁ , and R ₂ , substituted (C1-C30)alkyl, substituted (2-C30)alkenyl, substituted (C6-C30)aryl (ene ), substituted (3-30 membered) heteroaryl (ene), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted tri(C1-C30) alkylsilyl, substituted di( C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tri(C6-C30)arylsilyl, substituted (C3-C30) aliphatic The fused ring group of the ring and the aromatic ring of (C6-C30), and the substituents of substituted (C1-C30)alkyl (C6-C30)arylamino are each independently deuterium, halogen, cyano, carboxyl, nitro, hydride Roxy, (C1-C30)alkyl, halo (C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3) -C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or Unsubstituted (5-30 membered) heteroaryl, (5-30 membered) heteroaryl substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl , Di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, (C1-C30 ) Alkyl substituted or unsubstituted mono- or di- (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxy Carbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, At least one selected from the group consisting of (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl is preferred, and for example, substituted or unsubstituted phenyl, substituted Or beach It may be a substituted m-biphenyl, or a substituted or unsubstituted triazinyl.

Hereinafter, an organic electroluminescent compound according to an embodiment will be described.

The organic electroluminescent compound according to an embodiment is represented by Formula 1 below.

[Formula 1]

In Formula 1,

Y ₁ and Y ₂ are each independently O or S;

Each L ₁ is independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;

Ar ₁ is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered ) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di( C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted A fused ring group of a cyclic (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, or -N(Ar ₄ )(Ar ₅ ); Adjacent substituents may be linked to each other to form a ring;

Ar ₄ and Ar ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl , Or a substituted or unsubstituted (3-30 membered) heteroaryl;

R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, Or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; Adjacent substituents may be linked to each other to form a ring;

a is an integer of 0 to 4, and when a is an integer of 2 or more, each of -L ₁ -Ar ₁ may be the same or different from each other.

For example, Y ₁ and Y ₂ may be both O or S.

For example, each of L ₁ may be independently a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene, preferably a single bond , A substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5-18 membered) heteroarylene, for example, a single bond, or phenylene, naphthylene, or pyridylene. I can.

For example, Ar ₁ is each independently hydrogen, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-25 membered) heteroaryl, -N (Ar ₄ ) (Ar ₅ ), or Adjacent substituents may be linked to each other to form a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof. Preferably, Ar ₁ is each independently hydrogen, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-18 membered) heteroaryl, -N (Ar ₄ ) (Ar ₅ ), or Adjacent substituents may be connected to each other to form a substituted or unsubstituted (5-25 membered) monocyclic or polycyclic aromatic or a combination thereof, for example, hydrogen, substituted or unsubstituted phenyl, substituted Or unsubstituted naphthylenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl , -N (Ar ₄ ) (Ar ₅ ) or adjacent Ar ₁ may be connected to each other to form a substituted or unsubstituted fused ring.

For example, Ar ₄ and Ar ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C2-C10) alkenyl, substituted or unsubstituted (C6- C25) aryl, or may be a substituted or unsubstituted (5-25 membered) heteroaryl, preferably substituted or unsubstituted (C6-C18) aryl or substituted or unsubstituted (5-18 membered) heteroaryl May be, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl , It may be a substituted or unsubstituted carbazolyl.

For example, R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted Is a cyclic (5-25 member) heteroaryl; Adjacent R ₁ , adjacent R _2, or adjacent R ₁ and R ₂ may be connected to each other to form a ring. Preferably, R ₁ and R ₂ are each independently a substituted or unsubstituted (C6-C18)aryl or a substituted or unsubstituted (5-18 membered) heteroaryl; Adjacent R ₁ , adjacent R ₂ or adjacent R ₁ and R ₂ may be linked to each other to form a ring, for example, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl, or substituted or It may be unsubstituted carbazolyl.

In one embodiment, R ₁ is adjacent to each other, the adjacent R ₂ R ₁ and R ₂ to each other or adjacent to each other are connected to form a structure as described below, in the case of forming the ring may form a spiro structure with a core of the formula (I).

In the above structure, * is a point of connection with the core of Formula 1.

The organic electroluminescent compound of Formula 1 according to an example may be represented by any one of Formulas 2 to 4 below.

[Chemical Formula 2] [Chemical Formula 3]

[Formula 4]

In Formulas 2 to 4,

Y ₁ , Y ₂ , R ₁ , R ₂ , L ₁ , Ar ₁ , and a are the same as defined in Formula 1;

Ar ₂ , Ar ₃ , and Ar ₆ are the same as those of Ar ₁ ;

Y ₃ is O, S, -N(L ₂ -Ar ₇ ), or -C(Ar ₈ )(Ar ₉ );

L ₂ is the same as the definition of L ₁ above;

Ar ₇ is the same as the definition of Ar ₄ above;

Ar ₈ and Ar ₉ are each independently substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl;

b to d are each independently an integer of 1 to 4, e is an integer of 1 or 2, and when b to e are each an integer of 2 or more, each of Ar ₂ , Ar ₃ , Ar ₆ , and -L ₁ -Ar ₁ may be the same as or different from each other.

For example, Ar ₂ and Ar ₃ are each independently hydrogen, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-25 membered) heteroaryl, -N(Ar ₄ )(Ar ₅ ), or adjacent substituents are connected to each other to form a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or a combination thereof, preferably hydrogen, substituted or unsubstituted Substituted (C6-C18) aryl, substituted or unsubstituted (5-18 membered) heteroaryl, -N (Ar ₄ ) (Ar ₅ ), or substituted or unsubstituted (5-25 connected to each other with an adjacent substituent) Circle) of monocyclic or polycyclic aromatic or a combination thereof, for example, hydrogen, substituted or unsubstituted pyridinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted triazinyl , -N (Ar ₄ ) (Ar ₅ ), for example, substituted or unsubstituted diarylamine, or adjacent substituents are fused to each other to form a substituted or unsubstituted fluorene ring or a substituted or unsubstituted carbazole ring have.

For example, Ar ₆ is each independently hydrogen, substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic group connected to each other with an adjacent substituent , An aromatic or a combination thereof may form a ring, preferably hydrogen, unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5-25 membered) monocyclic ring connected to each other with an adjacent substituent Alternatively, a polycyclic aromatic or a combination thereof may be formed, and for example, hydrogen, substituted or unsubstituted phenyl, or adjacent substituents may be fused to each other to form a substituted or unsubstituted fluorene ring.

For example, L ₂ may be a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 member) heteroarylene, preferably a single bond, a substituted or unsubstituted It may be a (C6-C18) arylene, or a substituted or unsubstituted (5-18 membered) heteroarylene, and for example, it may be a single bond, or phenylene or pyridylene.

For example, Ar ₇ may be a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5-25 membered) heteroaryl, and preferably, a substituted or unsubstituted (C6-C18)aryl Or it may be a substituted or unsubstituted (5-18 membered) heteroaryl, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted It may be pyridinyl, substituted or unsubstituted pyrimidinyl.

Ar ₁ , Ar ₄ , Ar ₅ , R ₁ , and R ₂ according to an example may each independently be selected from any one of the substituents listed in Group 1 below.

[Group 1]

According to an example, the organic electroluminescent compound of Formula 1 may be more specifically exemplified as the following compounds, but is not limited thereto.

The compound that may be represented by Formula 1 according to the present application may be prepared as shown in Schemes 1 and 2 below, but is not limited thereto, and may be prepared by a synthetic method known to those skilled in the art.

[Scheme 1]

[Scheme 2]

In Reaction Schemes 1 and 2, the definition of each substituent is as defined in Formulas 1 to 4.

As described above, an exemplary synthesis example of a compound that may be represented by Formula 1 has been described according to an example, but these are all Buchwald-Hartwig cross coupling reaction, Suzuki cross-coupling reaction, Bromination reaction, organolithium reaction, and Phosphine-mediated reductive It will be readily understood by those skilled in the art that the reaction proceeds even if other substituents defined in Formulas 1 to 4 are bonded to each other in addition to the substituents specified in the specific synthesis examples based on the cyclization reaction.

The present application may provide an organic electroluminescent material including the organic electroluminescent compound of Formula 1 and an organic electroluminescent device including the organic electroluminescent material.

The organic electroluminescent material may be formed of the organic electroluminescent compound of the present application alone, or may further include conventional materials included in the organic electroluminescent material. When two or more types of materials are included in one layer, a layer may be formed by mixed deposition, or co-deposited separately at the same time to form a layer. The organic electroluminescent material according to an example may include one or more compounds represented by Formula 1 above. For example, the compound of Formula 1 may be included as a hole transport layer (HTL) material of an organic electroluminescent device.

The organic electroluminescent material of the present application may further include a host compound in addition to the organic electroluminescent compound of Formula 1 above. Preferably, the organic electroluminescent material may further include one or more dopants.

One or more phosphorescent or fluorescent dopants may be used as the dopant included in the organic electroluminescent material of the present disclosure, and phosphorescent dopants are preferred. The phosphorescent dopant material applied herein is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases is preferable. Specifically, it may be an ortho-metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, more preferably, an ortho-metalized iridium complex It can be a compound.

As the dopant, a compound represented by Formula 101 below may be used, but the present invention is not limited thereto.

[Formula 101]

In Chemical Formula 101,

L is selected from the following structures 1 or 2;

[Structure 1] [Structure 2]

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6 -C30)aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₀ to R ₁₀₃ may form a substituted or unsubstituted fused ring by linking adjacent substituents to each other, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzo Thienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline can be formed;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6 -C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₄ to R ₁₀₇ are adjacent substituents connected to each other to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted di Benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine can be formed;

R ₂₀₁ to R ₂₁₁ are each independently hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted ( C6-C30)aryl, and adjacent substituents may be linked to each other to form a substituted or unsubstituted fused ring;

s is an integer of 1 to 3.

Specifically, specific examples of the dopant compound are as follows, but is not limited thereto.

Hereinafter, an organic electroluminescent device to which the aforementioned organic electroluminescent compound or organic electroluminescent material is applied will be described.

An organic electroluminescent device according to an embodiment includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode.

The compound represented by Formula 1 herein may be included in one or more layers constituting an organic electroluminescent device. According to an example, the organic material layer includes an emission layer, a hole transport layer, and/or a hole auxiliary layer including the organic electroluminescent compound according to the present application. For example, when the compound of Formula 1 is included in the emission layer, it may be included as a host material. Here, the host material may be a host material of a green or red light-emitting organic electroluminescent device. In addition, when the compound of Formula 1 is included in the hole transport layer and/or the hole auxiliary layer, it may be included as a hole transport material and/or a hole auxiliary material, respectively. The emission layer, the hole transport layer, and/or the hole auxiliary layer may include, for example, the organic electroluminescent compound of the present application alone, or a mixture of at least two types of organic electroluminescent compounds, and included in the organic electroluminescent material. It may further include conventional materials.

In addition, the organic material layer may include a hole injection layer, a light emission auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer and an electron buffer layer, in addition to the emission layer, the hole transport layer, and the hole auxiliary layer. One or more selected layers may be further included, and each layer may be additionally composed of several layers. In addition, the organic material layer may further include one or more compounds selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds, and group 1, 2, period 4 transition metal, period 5 transition metal, lanthanum series One or more metals selected from the group consisting of metals and organometallics of d-transition elements, or one or more complex compounds containing such metals may be further included.

The organic electroluminescent material according to an example may be used as a light emitting material for a white organic light emitting device. The white organic electroluminescent device is a side-by-side method or a stacking method according to the arrangement of R (red), G (green) or YG (yellow green), B (blue) light emitting units. , Or a color conversion material (CCM) method, and various structures have been proposed. In addition, the organic electroluminescent material according to an example may be used for an organic electroluminescent device including a quantum dot (QD).

One of the first electrode and the second electrode may be an anode (anode) and the other may be a cathode (cathode). In this case, the first electrode and the second electrode may each be formed of a transparent conductive material, or may be formed of a transflective or reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a double-side emission type.

A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. For the hole injection layer, a plurality of layers may be used for the purpose of lowering a hole injection barrier (or a hole injection voltage) from an anode to a hole transport layer or an electron blocking layer, and two compounds may be used simultaneously for each layer. Also, the hole injection layer may be doped with p-dopant. The electron blocking layer is located between the hole transport layer (or the hole injection layer) and the emission layer, and blocks overflow of electrons from the emission layer to confine excitons in the emission layer to prevent leakage of light. A plurality of layers may be used for the hole transport layer or the electron blocking layer, and a plurality of compounds may be used for each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer or an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. In the electron buffer layer, a plurality of layers may be used for the purpose of controlling electron injection and improving interfacial properties between the light emitting layer and the electron injection layer, and two compounds may be used simultaneously for each layer. A plurality of layers may be used for the hole blocking layer or the electron transport layer, and a plurality of compounds may be used for each layer. In addition, the electron injection layer may be doped with n-dopant.

The light emitting auxiliary layer is a layer positioned between the anode and the light emitting layer, or between the cathode and the light emitting layer, and when the light emitting auxiliary layer is positioned between the anode and the light emitting layer, it facilitates injection and/or transmission of holes or It may be used for blocking overflow, and when the light emitting auxiliary layer is positioned between the cathode and the light emitting layer, it may be used to facilitate injection and/or transmission of electrons or to block overflow of holes. In addition, the hole auxiliary layer is located between the hole transport layer (or the hole injection layer) and the light emitting layer, and may exhibit an effect of smoothing or blocking a hole transfer rate (or injection rate), and accordingly, a charge balance ) Can be adjusted. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer may be used as a hole auxiliary layer or an electron blocking layer. The light emission auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

In the organic electroluminescent device of the present application, on the inner surface of at least one of the pair of electrodes, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer" It is desirable to place ). Specifically, it is preferable to provide a silicon and aluminum chalcogenide (including oxide) layer on the surface of the anode 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. Stabilization of driving of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide include SiO _X (1≤X≤2), AlO _X (1≤X≤1.5), SiON, SiAlON, etc., and preferred examples of the metal halide are 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.

Further, in the organic electroluminescent device of the present application, it is also preferable 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. 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, it is possible to manufacture an organic electroluminescent device emitting white light having two or more light emitting layers by using the reducing dopant layer as a charge generating layer.

The formation of each layer of the organic electroluminescent device of the present application is a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, etc., ink jet printing, nozzle printing, slot coating, Any one of wet film forming methods such as spin coating, dip coating, and flow coating can be applied.

In the case of wet film formation, 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., and the solvent is dissolved or dispersed in the material forming each layer. It can be made, and any one may be used as long as there is no problem with the film forming property.

In addition, the present application may provide a display device using the compound represented by Chemical Formula 1. That is, it is possible to manufacture a display device or a lighting device by using the compound of the present application. Specifically, manufacturing a display device, such as a smart phone, tablet, notebook, PC, TV or vehicle display device, or a lighting device, for example, an outdoor or indoor lighting device using the compound of the present application It is possible.

Hereinafter, for a detailed understanding of the present application, a method for preparing a compound according to the present application will be described by taking the synthesis method of the representative compound or intermediate compound of the present application as an example.

[Example 1] Synthesis of Compound C-3

Synthesis of compound 1-1

Catechol (20 g, 181.7 mmol), α,α-dichlorodiphenylmethane (43 g, 181.7 mmol), and 454 mL of toluene were added to a 1 L round bottom flask (RBF), and stirred at 100° C. for 27 hours. , The reaction mixture was cooled to room temperature and concentrated by distillation. The obtained mixture was purified by column chromatography to obtain compound 1-1 (41 g, 82%).

Synthesis of compound 1-2

Compound 1-1 (20 g, 73.0 mmol) and 730 mL of dimethylformamide (DMF) were added to 1L RBF, stirred at room temperature for 10 minutes, and then N-bromosuccinimide (NBS) (13.6 g , 76 mmol) and reacted at room temperature for 24 hours. When the reaction was completed, the reaction mixture was distilled and the obtained solid was purified by column chromatography to obtain compound 1-2 (24.4 g, 95%).

Synthesis of compound C-3

N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (6.8 g, 19.4 mmol), tris(dibenzylideneacetone) in 500 mL RBF ) Dipalladium (0) (Pd ₂ (dba) ₃ ) (710 mg, 0.776 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (637 mg, 1.55 mmol), sodium tert -butoxide (NaOtBu) (2.8 g, 29 mmol), and 144 mL of toluene were added, followed by heating to 100°C. After dissolving Compound 1-2 in 50 mL of toluene, it was added dropwise to the reaction mixture and reacted for 3 hours. When the reaction is over, the reaction mixture is cooled to room temperature, the organic layer is extracted with dichloromethane, the remaining moisture in the organic layer is removed with MgSO ₄ and dried, and the reaction mixture is purified by column chromatography to obtain compound C-3 (1 g, 8%). Got it.

[Example 2] Synthesis of Compound C-1

N-phenyl-[1,1'-biphenyl]-4-amine (10 g, 19.4 mmol), Pd ₂ dba ₃ (1.5 g, 1.64 mmol), s-phos (1.3 g, 3.3 mmol) in 500 mL RBF ), NaOtBu (5.9 g, 61 mmol), and 310 mL of toluene were added and heated to 100°C. After dissolving Compound 1-2 in 100 mL of toluene, it was added dropwise to the reaction mixture and reacted for 3 hours. When the reaction is over, the reaction mixture is cooled to room temperature, the organic layer is extracted with dichloromethane, the remaining moisture in the organic layer is removed with MgSO ₄ and dried, and the reaction mixture is purified by column chromatography to obtain compound C-1 (7.5 g, 35%). Got it.

Hereinafter, for detailed understanding of the present application, a method of manufacturing an organic electroluminescent device including the organic electroluminescent compound of the present application and device characteristics will be described.

[Device Examples 1 and 2] Fabrication of an organic electroluminescent device using the organic electroluminescent compound according to the present invention

An organic electroluminescent device was manufactured using the organic electroluminescent compound according to the present application. First, the transparent electrode ITO thin film (10Ω/□) obtained from the glass for an organic electroluminescent device (manufactured by Geomatech) was subjected to ultrasonic cleaning by sequentially using acetone and isopropane alcohol, and then stored in isopropane alcohol before use. I did. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, insert HI-1 into the cell in the vacuum evaporation equipment, exhaust until the degree of vacuum in the chamber reaches 10 ^-6 torr, and then apply current to the cell. By evaporation, a first hole injection layer having a thickness of 80 nm was deposited on the ITO substrate. Subsequently, HI-2 was put into another cell in the vacuum deposition equipment, and a second hole injection layer having a thickness of 5 nm was deposited on the first hole injection layer by evaporating by applying a current to the cell. Subsequently, HT-1 was put into a cell in a vacuum evaporation equipment, and a current was applied to the cell to evaporate to deposit a first hole transport layer having a thickness of 10 nm on the second hole injection layer. The second hole transport layer material of Table 1 was added to another cell in the vacuum deposition equipment, and a second hole transport layer (hole auxiliary layer) having a thickness of 30 nm was deposited on the first hole transport layer by evaporation by applying a current to the cell. . After forming the hole injection layer and the hole transport layer, compound H-1 was added as a host thereon, and D-1 material was added to another cell, and dopant was doped in an amount of 10% by weight relative to the deposition rate of the light emitting layer. A light emitting layer having a thickness of 40 nm was deposited on the hole transport layer. Subsequently, ET-1 and EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the emission layer. Subsequently, as an electron injection layer, EI-1 was deposited to a thickness of 2 nm, and an Al cathode was deposited to a thickness of 800 nm using another vacuum deposition equipment to prepare an OLED.

[Device Comparative Example 1] Fabrication of an organic electroluminescent device not in accordance with the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that HT-1 was used as the second hole transport material (hole auxiliary material).

The driving voltage, current efficiency, power efficiency, external quantum efficiency, and color coordinate results based on 1,000 nits luminance of the organic electroluminescent devices of Device Examples 1 and 2 and Device Comparative Example 1 prepared as described above are shown in Table 1 below.

Referring to Table 1, when the organic electroluminescent compound according to the present invention is used as a material for the second hole transport layer of an organic electroluminescent device, a device using a conventional hole transport material in terms of current efficiency, power efficiency, and external quantum efficiency. It can be seen that all are superior to Comparative Example 1, and accordingly, it can be expected that the organic electroluminescent device according to an example has high luminous efficiency.

The compounds used in Device Examples 1 and 2 and Device Comparative Example 1 are shown in Table 2 below.

Claims (8)

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

In Formula 1,
Y ₁ and Y ₂ are each independently O or S;
Each L ₁ is independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene;
Ar ₁ is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered ) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di( C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted A fused ring group of a cyclic (C3-C30) aliphatic ring and an (C6-C30) aromatic ring, or -N(Ar ₄ )(Ar ₅ ); Adjacent substituents may be linked to each other to form a ring;
Ar ₄ and Ar ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl , Or a substituted or unsubstituted (3-30 membered) heteroaryl;
R ₁ and R ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, Or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; Adjacent substituents may be linked to each other to form a ring;
a is an integer of 0 to 4, and when a is an integer of 2 or more, each of -L ₁ -Ar ₁ may be the same or different from each other. The organic electroluminescent compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 2 to 4:
[Chemical Formula 2] [Chemical Formula 3]

[Formula 4]

In Formulas 2 to 4,
Y ₁ , Y ₂ , R ₁ , R ₂ , L ₁ , Ar ₁ , and a are the same as defined in claim 1;
Ar ₂ , Ar ₃ , and Ar ₆ are the same as those of Ar ₁ ;
Y ₃ is O, S, -N(L ₂ -Ar ₇ ), or -C(Ar ₈ )(Ar ₉ );
L ₂ is the same as the definition of L ₁ above;
Ar ₇ is the same as the definition of Ar ₄ above;
Ar ₈ and Ar ₉ are each independently substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6-C30)aryl;
b to d are each independently an integer of 1 to 4, e is an integer of 1 or 2, and when b to e are each an integer of 2 or more, each of Ar ₂ , Ar ₃ , Ar _6, and -L ₁ -Ar ₁ may be the same as or different from each other. The organic electroluminescent compound of claim 1, wherein Ar ₁ , Ar ₄ , Ar ₅ , R ₁ , and R ₂ are each independently selected from any one of the substituents listed in Group 1 below.
[Group 1]

The method of claim 1, wherein L ₁ , Ar ₁ , Ar ₄ , Ar ₅ , R ₁ , and R ₂ are substituted (C1-C30)alkyl, substituted (C2-C30)alkenyl, substituted (C6- C30) aryl (ene), substituted (3-30 membered) heteroaryl (ene), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted tri (C1-C30) alkylsilyl , Substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tri(C6-C30)arylsilyl, substituted (C3) The fused ring group of the aliphatic ring of -C30) and the aromatic ring of (C6-C30), and the substituents of substituted (C1-C30)alkyl(C6-C30)arylamino are each independently deuterium, halogen, cyano, Carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30) )Alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 member)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6- C30) aryl substituted or unsubstituted (5-30 membered) heteroaryl, (5-30 membered) heteroaryl substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri( C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkyl Amino, mono- or di- (C6-C30) arylamino unsubstituted or substituted with (C1-C30)alkyl, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30) ) Arylboronyl, (C6-C30) ar (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) at least one selected from the group consisting of aryl, an organic electroluminescent compound. The organic electroluminescent compound of claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent compound is included in at least one of an emission layer, a hole transport layer, and a hole auxiliary layer.

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