KR20200031510A - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.

Description

An organic electroluminescent compound and an organic electroluminescent device comprising the same {ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

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

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

An organic electroluminescent device (OLED) is a device that converts electric energy into light by applying electricity to an organic light emitting material, and 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 includes a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, if necessary can do. Materials used for the organic layer are hole injection materials, hole transport materials, hole auxiliary materials, light emitting auxiliary materials, electron blocking materials, light emitting materials (including host and dopant materials), electron buffer materials, hole blocking materials, electrons depending on the function It can be divided into a delivery material, an electron injection material, and the like. In such an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode to the emission layer by applying a voltage, and excitons having high energy are formed by recombination of holes and electrons. By this energy, the light-emitting organic compound is brought into an excited state, and the excitation state of the light-emitting organic compound is returned to the ground state, thereby emitting energy as light and emitting light.

The light-emitting material of the organic electroluminescent device is the most important factor for determining the light-emitting efficiency of the device, the light-emitting 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 emission color, and there are also yellow or orange light emitting materials. In addition, the light-emitting material may be divided into a host material and a dopant material in terms of functionality. It is preferable that the host material serving as a solid solvent and an energy transporter has high purity and a suitable molecular weight to enable vacuum deposition. In addition, it is preferable that the glass transition temperature and the thermal decomposition temperature are high to have thermal stability, high electrochemical stability for long life, and easy to form an amorphous thin film.

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- and large-sized OLED panels, it is urgent to develop materials that are superior to conventional light-emitting materials. .

On the other hand, U.S. Patent Publication No. 6,706,423 discloses a compound containing indole as a luminescent material, but still needs to be developed to improve the performance of the OLED.

U.S. Patent Publication No. 6,706,423 (issued on March 16, 2004)

An object of the present application is to provide an organic electroluminescent compound that is effective in manufacturing an organic electroluminescent device having characteristics of low driving voltage, high luminous efficiency and / or long life, and has good thermal stability.

Compounds having a low glass transition temperature (Tg) may reduce charge mobility in thin films and degrade OLED device performance. Accordingly, the present inventors, as a result of diligent research, have a planar main core, which can help pi-pi stacking in a vacuum deposition layer, resulting in fast charge mobility and low molecular weight. A new organic electroluminescent compound having a higher Tg and providing excellent morphological stability has been developed. Specifically, 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 Chemical Formula 1,

A ₁ to A ₁₁ are each independently N or CR ₁ ;

X ₁ is N, NR ₃ or CR ₄ , X ₂ is N or C, provided that at least one of X ₁ and X ₂ includes N;

R ₁ , R ₃ , R _4, Ar ₁ and Ar 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 di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tree (C6-C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; Two or more adjacent R ₁ may be connected to each other to form a ring; When there are multiple R _{1 s} , each R ₁ may be the same or different from each other;

L ₁ is each independently a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-30 membered) heteroarylene, Or a substituted or unsubstituted (C3-C30) cycloalkylene.

The organic electroluminescent compound according to the present application can provide an organic electroluminescent device having good thermal stability and, simultaneously or alternatively, characteristics of low driving voltage, high luminous efficiency and / or long life.

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

The present application will be described in more detail below, but it is for illustrative purposes and should not be construed to limit the scope of the present application.

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

As used herein, "organic electroluminescent material" means a material that can be used in an organic electroluminescent device, and may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material is a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material (including host material and dopant material), an electron buffer material, a hole blocking material, Electron transfer materials, electron injection materials, and the like.

As used herein, "(C1-C30) alkyl (ren)" means a straight or branched chain alkyl (ren) having 1 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 1 to 20 carbon atoms, more preferably It is 1-10. Specific examples of the alkyl include methyl, ethyl, n -propyl, isopropyl, n -butyl, isobutyl and tert -butyl. As used herein, "(C2-C30) alkenyl" means a straight or branched chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20 carbon atoms, more preferably 2 to 20 carbon atoms. 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. As used herein, "(C2-C30) alkynyl" means a straight or branched chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20 carbon atoms, more preferably 2 to 20 carbon atoms. 10. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. As used herein, "(C3-C30) cycloalkyl (ren)" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, and preferably 3 to 20 carbon atoms, more preferably 3 to 3 carbon atoms. Seven. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7 ring skeleton atoms, preferably 5 to 7, and is a group consisting of B, N, O, S, Si and P, preferably O , S and N means a cycloalkyl containing one or more heteroatoms selected from the group consisting of, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "(C6-C30) aryl (ren)" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated. The number of carbons of the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzoflu Orenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, perylene, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. . More specifically, examples of the aryl include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, benzanthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, naphthacenyl group, pyrenyl group, 1-cristenyl group, 2-cristenyl group, 3-cristenyl group, 4 -Crysenyl group, 5-Crysenyl group, 6-Crysenyl group, benzo [c] phenanthryl group, benzo [g] cristenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-tri Phenylenyl group, 4-triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, benzofluorenyl group, dibenzofluorene Neil group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-terphenyl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2- Diary, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-quaterphenyl group, 3-fluoranthenyl group, 4-fluoranthenyl group, 8- Luoranthenyl group, 9-fluoranthenyl group, benzofluoranthenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5 -Xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 4'-methylbiphenylyl group, 4 "-t- Butyl-p-terphenyl-4-yl group, 9,9-dimethyl-1-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-dimethyl-3-fluorenyl group, 9,9 -Dimethyl-4-fluorenyl group, 9,9-diphenyl-1-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-3-fluorenyl group, 9, And 9-diphenyl-4-fluorenyl groups.

As used herein, "(3-30 membered) heteroaryl (ren)" is aryl having 3 to 30 ring skeleton atoms and comprising one or more heteroatoms selected from the group consisting of B, N, O, S, Si and P. Means The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system fused with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein also includes a form in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and includes a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, iso Quinolinyl, cynolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazineyl, Phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. It must include heteroaryl ring systems. More specifically, examples of the heteroaryl include 1-pyrroleyl group, 2-pyrrrolyl group, 3-pyrrrolyl group, pyrazinyl group, 2-pyridinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5- Pyrimidinyl group, 6-pyrimidinyl group, 1,2,3-triazine-4-yl group, 1,2,4-triazine-3-yl group, 1,3,5-triazine-2-yl group, 1 -Imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7 -Indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group , 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group , 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group Group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7 -Benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-qui Teal group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquine group Teal group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazolyl-1-yl group, Azacarbazolyl-2-yl group, azacarbazolyl-3-yl group, azacarbazolyl-4-yl group, azacarbazolyl-5-yl group, azacarbazolyl-6-yl group, azacar Zolyl-7-yl group, azacarbazolyl-8-yl group, azacarbazolyl-9-yl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridyl group Nyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3 -Acridinyl group, 4-acridinyl group, 9-acridinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3 -Furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl group, 2-methylpyrrole-5-yl group , 3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group, 2-t-butylpyrrole-4-yl group, 3- (2-phenylpropyl) pyrrole-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2- t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t- Butyl-3-indolyl group, 4-t-butyl-3-indolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzo Thiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-silafluorenyl group, 2-silafluorenyl group, 3-silafluorenyl group, 4-silafluore And a nil group, a 1-germa fluorenyl group, a 2-germa fluorenyl group, a 3-germa fluorenyl group, and a 4-germa fluorenyl group. “Halogen” as used herein includes F, Cl, Br and I atoms.

Also, “ortho (o-)”, “meta (m-)”, and “para (p-)” are each prefixes indicating the relative positions of the substituents. Ortho (ortho) indicates that two substituents are adjacent to each other. For example, when the substituents are in positions 1 and 2 in a benzene substituent, they are called ortho positions. The meta indicates that the two substituents are in the 1,3 position, for example, the meta position when the substituent is in the 1, 3 position in the benzene substituent. Para indicates that two substituents are in the 1,4 position, for example, when a substituent is 1, 4 in the benzene substituent, it is called a para position.

In the description of "substituted or unsubstituted" as used herein, 'substitution' means that a hydrogen atom in one functional group is replaced by another atom or another functional group (ie, a substituent). As used herein, substituted (C1-C30) alkyl (ren), substituted (C6-C30) aryl (ren), substituted (3-30 membered) heteroaryl (ren), substituted (C3-C30) cycloalkyl (Ren), 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 mono- or di- (C1-C30) alkylamino, substituted mono- or di- (C6-C30) arylamino, and 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 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (3-30 membered) heteroaryl substituted or unsubstituted with one or more (C6-C30) aryl, one or more (3-30 won) (C6-C30) aryl, unsubstituted or substituted with roaryl, 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, mono- or di- (C6-C30) unsubstituted or substituted with one or more (C1-C30) alkyl Arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) Arylboronil, di (C1-C30) alkylboronil, (C1-C30) alkyl (C6-C30) arylboronil, (C6-C30) ar (C1-C30) alkyl, and (C1- C30) alkyl (C6-C30) aryl. According to one aspect of the present application, the substituents are each independently one or more of (C1-C20) alkyl, (C6-C25) aryl and (3-25 membered) heteroaryl. According to another aspect of the present application, the substituents are each independently one or more of (C1-C10) alkyl, (C6-C18) aryl and (5-20 membered) heteroaryl. For example, the substituents may each independently be one or more of methyl, phenyl, naphthyl, biphenyl and dibenzofuranyl.

In the present application, a ring formed in connection with an adjacent substituent is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or combination of two or more adjacent substituents. Meaning, and may be a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic or a combination of these. Further, the formed ring may include one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S.

In the formulas herein, heteroaryl (ren) and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si and P. Further, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 members) 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 Mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl One or more selected from the group consisting of amino may be bound.

In Formula 1, A ₁ to A ₁₁ are each independently N or CR ₁ . According to one aspect of the present application, A ₁ to A ₁₁ are each independently CR ₁ .

R 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 Mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) aryl Amino; Two or more adjacent R ₁ may be connected to each other to form a ring. When there are multiple R _{1 s} , each R ₁ may be identical to or different from each other. According to one aspect of the present application, R ₁ is each independently hydrogen, deuterium, unsubstituted (C1-C20) alkyl, unsubstituted (C6-C25) aryl, or unsubstituted (5-25 membered) heteroaryl ; Two adjacent R ₁ may be connected to each other to form a ring. According to another aspect of the present application, R ₁ are each independently hydrogen; Two adjacent R ₁ may be connected to each other to form a ring. The ring is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or combinations thereof, preferably an unsubstituted (5-25 membered) monocyclic or polycyclic alicyclic May be a ring of a group, aromatic or combinations thereof, and may include one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S, , For example, it may be a benzene ring, pyridine ring, benzofuran ring, benzothiophene ring and the like.

는 결합되는 치환기에 따라, 각각 단일 결합 또는 이중 결합을 나타낸다. 예를 들면, X₂가 N이면, X₂와 연결된

는 단일 결합이고, X₁이 N이면, X₁과 연결된

는 이중 결합이다.In Formula 1, X ₁ is N, NR ₃ or CR ₄ , X ₂ is N or C, provided that at least one of X ₁ and X ₂ includes N. Specifically, when X ₂ is N, X ₁ is N, NR ₃ or CR ₄ , and when X ₂ is C, X ₁ is N or NR ₃ . For example, when X ₂ is N, X ₁ may be N or CR ₄ , and when X ₂ is C, X ₁ may be NR ₃ . In Chemical Formula 1,

Represents a single bond or a double bond, depending on the substituent to be bonded, respectively. For example, if X ₂ is N, connected to X ₂

Is a single bond, and when X ₁ is N, connected to X ₁

Is a double bond.

R ₃ and R ₄ 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 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 mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6- C30) arylamino, or may be connected to adjacent substituents to form a ring. According to an aspect of the present application, R ₃ and R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 won) Heteroaryl. According to another aspect of the present application, R ₃ and R ₄ are each independently hydrogen, deuterium, unsubstituted (C1-C10) alkyl, unsubstituted (C6-C18) aryl, or unsubstituted (5-20 membered) ) Heteroaryl. For example, R ₃ may each independently be phenyl, and R ₄ may each independently be hydrogen.

In Formula 1, Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted (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 mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) ) Alkyl (C6-C30) arylamino. According to an aspect of the present application, Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted ( 5-25 membered) heteroaryl, substituted or unsubstituted mono- or di- (C1-C20) alkylamino, substituted or unsubstituted mono- or di- (C6-C25) arylamino, or substituted or unsubstituted (C1-C20) alkyl (C6-C25) arylamino. According to another aspect of the present application, Ar ₁ is each independently unsubstituted (C6-C18) aryl; (C6-C18) aryl and (3-20 membered) heteroaryl substituted or unsubstituted (5-20 membered) heteroaryl; And di (C6-C18) arylamino unsubstituted or substituted with one or more (C1-C6) alkyl. According to another aspect of the present application, Ar ₂ is each independently hydrogen, deuterium, unsubstituted (C6-C18) aryl, or unsubstituted (5-20 membered) heteroaryl. For example, Ar ₁ is each independently phenyl; Biphenyl; Pyridyl unsubstituted or substituted with phenyl; Pyrimidinyl unsubstituted or substituted with one or more phenyl; Triazinyl substituted with one or more of phenyl, biphenyl, naphthyl and dibenzofuranyl; Quinazolinyl substituted with phenyl; Quinoxalinyl substituted with phenyl; Carbazolyl; Dibenzofuranyl; Benzoquinazolinyl substituted with phenyl; Benzoquinoxalinyl substituted with phenyl; Dimethylfluorenylphenylamino, and the like. For example, Ar ₂ may each independently be hydrogen, deuterium, phenyl, pyridyl, and the like.

In Chemical Formula 1, L ₁ is each independently a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) ) Heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene. According to an aspect of the present application, L ₁ is each independently a single bond, substituted or unsubstituted (C6-C25) arylene, or substituted or unsubstituted (5-25 membered) heteroarylene. According to another aspect of the present application, L ₁ is each independently a single bond, unsubstituted (C6-C18) arylene, or (C6-C10) aryl substituted or unsubstituted (5-20 membered) heteroarylene. to be. For example, L ₁ is each independently a single bond, phenylene, naphthylene, biphenylene, pyridylene, pyrimidineylene substituted with phenyl, triazinylene substituted with phenyl, quinazolinylene, quinoxalinylene, Benzoquinazolinylene, benzoquinoxalinylene, and the like.

The compound represented by Formula 1 may be represented by any one of the following Formulas 2 to 8.

[Formula 2] [Formula 3]

[Formula 4] [Formula 5]

[Formula 6]                        [Formula 7]

[Formula 8]

In Chemical Formulas 2 to 4, Y ₁ is NR ₅ , O, S, CR ₆ R ₇ . According to one aspect of the present application, Y ₁ is O or S.

In the above formulas 5 to 7, T ₁ to T ₄ are each independently CR ₈ or N.

In Formulas 2 to 8, R ₁ , R ₂ , and R ₅ to R ₈ 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 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 mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or Substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino. When R ₁ , R ₂ and R ₈ are each plural, each R ₁ , each R ₂ , and each R ₈ may be the same or different from each other. According to an aspect of the present application, R ₁ , R ₂ , and R ₅ to R ₈ are each independently hydrogen, deuterium, unsubstituted (C1-C20) alkyl, unsubstituted (C6-C25) aryl, or unsubstituted It is (3-25 won) heteroaryl. According to an aspect of the present application, R ₁ , R ₂ , and R ₅ to R ₈ are each independently hydrogen or deuterium. For example, R ₁ , R ₂ , and R ₅ to R ₈ may each independently be hydrogen.

In the above formulas 2 to 8, a is each independently an integer of 1 or 2, b and c are each independently an integer of 1 to 4, d is an integer of 1 to 3, and each R ₁ and each R ₂ may be the same or different from each other.

In Formulas 2 to 8, A ₁ to A ₁₁ , X ₁ , X ₂ , L ₁ , Ar ₁ and Ar ₂ are as defined in Formula 1.

The compound represented by Formula 1 may be represented by any one of the following Formulas 11 to 13.

[Formula 11]       [Formula 12]

[Formula 13]

In Formulas 11 to 13, A ₁ to A ₁₁ , R ₃ , L ₁ , Ar ₁ and Ar ₂ are as defined in Formula 1.

The compound represented by Formula 1 may be exemplified as the following compounds, but is not limited thereto.

The organic electroluminescent compounds herein can be prepared by synthetic methods known to those skilled in the art. For example, the organic electroluminescent compound of the present application may be synthesized as shown in the following reaction schemes, but is not limited thereto.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Reaction Scheme 4]

[Scheme 5]

[Scheme 6]

[Scheme 7]

[Scheme 8]

[Scheme 9]

[Scheme 10]

In Reaction Schemes 1 to 10, A ₁ to A ₁₁ , X ₁ , X ₂ , R ₁ , R ₂ , R ₅ , L ₁ , Ar ₁ and Ar ₂ are the same as defined in Chemical Formulas 1 to 8.

Although the exemplary synthetic examples of the present invention represented by Formula 1 have been described above, these are all Buchwald-Hartwig cross coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, Intramolecular acid-induced cyclization reaction, Pd (II) -catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN ₁ substitution reaction, SN ₂ substitution reaction, and Phosphine-mediated reductive cyclization reaction, Vilsmeier-Haack reaction, etc. It will be readily understood by those skilled in the art that the reaction proceeds even if other substituents defined in Chemical Formula 1 are combined in addition to the substituents specified in the specific synthesis examples.

The dopant that can be used in combination with the compounds herein can be one or more phosphorescent or fluorescent dopants, with phosphorescent dopants being preferred. The phosphorescent dopant is not particularly limited, but may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and preferably, iridium ( Ir), osmium (Os), copper (Cu) and platinum (Pt) may be an ortho metallized complex compound of a metal atom, and more preferably, an ortho metallized iridium complex compound.

As a dopant included in the organic electroluminescent device of the present application, a compound represented by Formula 101 may be used, but is not limited thereto.

[Formula 101]

In Chemical Formula 101,

L is selected from structures 1 or 2 below;

[Structure 1] [Structure 2]

R ₁₀₀ to R ₁₀₃ and 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, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; Can be connected to adjacent substituents to form a ring; Specifically, R ₁₀₀ to R ₁₀₃ may be linked to each other by adjacent substituents to form a ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, Can form a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline ring;

R ₁₀₄ to R ₁₀₇ may be linked to each other by adjacent substituents to form a ring, for example, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or Unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine ring;

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, or may be connected to an adjacent substituent to form a ring;

s is an integer from 1 to 3.

Specifically, a specific example of the dopant is as follows, but is not limited thereto.

The compound represented by Formula 1 herein may be included in one or more layers constituting the organic electroluminescent device, for example, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, It may be included in one or more layers selected from an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. In addition, the compound represented by Formula 1 herein is not limited thereto, and may be included in the light emitting layer, and may be included in the light emitting layer as a host material.

Of the organic electroluminescent materials herein, for example, hole injection material, hole transport material, hole auxiliary material, light emitting auxiliary material, electron blocking material, light emitting material, electron buffer material, hole blocking material, electron transport material and electron injection material One or more materials may include a compound represented by Chemical Formula 1 above. The material may be a light emitting material. The light-emitting material may be composed of the compound represented by Formula 1 alone, and may further include common materials included in the organic electroluminescent material.

The organic electroluminescent device of the present application includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer includes at least one light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer and an electron blocking layer It may further include one or more layers selected from the layers.

Each of the first electrode and the second electrode may be formed of a transparent conductive material, or may be formed of a semi-transmissive 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 front emission type, a back emission type, or a double-sided emission type. Further, the hole injection layer may be additionally doped with p-dopant, and the electron injection layer may be additionally doped with n-dopant.

The organic electroluminescent device of the present application may include the compound represented by Chemical Formula 1, and may further include conventional materials included in the organic electroluminescent material. The organic electroluminescent device including the organic electroluminescent compound of the present application represented by Formula 1 may exhibit high luminous efficiency and / or long life characteristics.

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 using the compound of the present application. Specifically, it is possible to manufacture a display device, for example, a smart phone, a tablet, a notebook, a PC, a TV or a 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, representative compounds of the present application are shown, and methods for preparing the compounds according to the present application and their physical properties are shown. However, the present application is not limited to the following examples.

 [Synthesis Preparation Example 1] Preparation of compound C-15

compound 1-1 Manufacturing

After adding 100 g (0.709 mol) of 1-fluoro-2-nitrobenzene to the reaction vessel, 90.4 g (0.709 mol) of 2-chloroaniline, 59.7 g (1.063 mol) of potassium hydroxide, and 800 mL of dimethyl sulfoxide, 150 Stir at 3 ° C. for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed by rotary evaporation. After that, purification was performed by column chromatography to obtain 62 g of Compound 1-1 (yield: 35%).

compound 1-2 Manufacturing

To the reaction vessel, 72 g (0.290 mol) of compound 1-1 , 326.6 g (1.448 mol) of stannous chloride dihydrate, and 1400 mL of ethanol were added, followed by stirring at 70 ° C for 2 hours. After the reaction was completed, the mixture was slowly cooled to 0 ° C and neutralized with an aqueous sodium hydroxide solution. After neutralization, it was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed by rotary evaporation. After that, purification was performed by column chromatography to obtain 53 g of compound 1-2 (yield: 63%).

compound 2-1 Manufacturing

After adding 60 g (0.450 mol) of oxindole, 105 mL (1.350 mol) of N, N-dimethylformamide, 126 mL (1.350 mol) of phosphorus oxychloride, and 1200 mL of 1,2-dichloroethene to the reaction vessel, Stirred at 50 ° C. for 12 hours. After the reaction, the mixture was cooled to room temperature and neutralized with an aqueous potassium carbonate solution. After neutralization, the mixture was extracted with ethyl acetate, and the extracted organic layer was dried over magnesium sulfate, and then the solvent was removed by rotary evaporation. Thereafter, purification was performed by column chromatography to obtain 35 g of compound 2-1 (yield: 43%).

compound 2-2 Manufacturing

Compound 2-1 32.5 g (0.181 mol), phenylboronic acid 33.1 g (0.271 mol), tetrakis (triphenylphosphine) palladium (O) 10.5 g (0.009 mol), potassium carbonate 48 g (0.452 mol) ), 880 mL of toluene, 220 mL of ethanol, and 220 mL of distilled water were added, followed by stirring at 130 ° C. for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed by rotary evaporation. After that, purification by column chromatography gave 38.3 g of a compound 2-2 (yield: 95%).

compound 3-1 Manufacturing

To the reaction vessel, 20.7 g (95.0 mmol) of compound 1-2 , 21 g (95.0 mmol) of compound 2-2 , 21.7 g (114.0 mmol) of sodium disulfite, and 320 mL of N, N-dimethylformamide were added, followed by addition of 180 mL. Stir for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed by rotary evaporation. After that, purification was performed by column chromatography to obtain 19.5 g of compound 3-1 (yield: 40%).

compound 3-2 Manufacturing

19 g (45.2 mmol) of compound 3-1 in reaction vessel, 1.0 g (4.52 mmol) of palladium (II) acetate, 3.3 g (9.04 mmol) of tricyclohexylphosphine tetrafluoroborate, 44.2 g of cesium carbonate (135.6 mmol) , And N, N-dimethylacetamide 230 mL was added, followed by stirring at 130 ° C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed by rotary evaporation. Thereafter, the mixture was purified by column chromatography to obtain 3.5 g of compound 3-2 (yield: 20%).

compound C-15 Manufacturing

In the reaction vessel, compound 3-2 2.7 g (7.0 mmol), 2-chloro-4-phenylquinazoline 1.7 g (7.0 mmol), tris (dibenzylideneacetone) dipalladium (0) 0.32 g (0.35 mmol), tri -0.32 mL (0.70 mmol) of tert -butylphosphine, 1.7 g (18.0 mmol) of sodium tert -butoxide, and 135 mL of o-xylene were added, followed by stirring at 120 ° C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed by rotary evaporation. Then, purified by column chromatography to obtain 2.7 g of Compound C-15 (yield: 65%).

The physical properties of the synthesized compound are summarized in Table 1 below.

[Table 1]

H-NMR data for compound C-15

Hereinafter, for the detailed understanding of the present invention, properties of the organic electroluminescent device including the compound of the present application will be described. However, the following examples merely describe the characteristics of the OLED according to the present application for a detailed understanding of the present application, and the present application is not limited to the following examples.

[Device Manufacturing Example 1] OLED production including the compound according to the present application

An OLED device comprising the compound according to the present application was prepared. First, the transparent electrode ITO thin film (10 Ω / □) obtained from the glass for OLED (manufactured by Geomatech Co., Ltd.) was subjected to ultrasonic cleaning using acetone, ethanol and distilled water sequentially, and then stored in isopropanol for use. Next, after mounting the ITO substrate on the substrate holder of the vacuum deposition equipment, put compound HI-1 in the cell in the vacuum deposition equipment and evacuate until the vacuum in the chamber reaches 10 ^-6 torr, and then apply a current to the cell Then, a first hole injection layer having a thickness of 80 nm was deposited on the ITO substrate by evaporation. Subsequently, compound HI-2 was put into another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a 5 nm thick second hole injection layer on the first hole injection layer. Subsequently, Compound HT-1 was put into a cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate to deposit a 10 nm thick first hole transport layer on the second hole injection layer. Compound HT-2 was put in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate to deposit a 60 nm thick second hole transport layer on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. In a cell in a vacuum deposition apparatus, a compound described as a host material is put in Table 2 below as a host, and compound D-39 is added as a dopant in another cell. A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by doping. Subsequently, in another cell, the compound ET-1 and the compound EI-1 were evaporated at a rate of 1: 1 to deposit a 35 nm thick electron transport layer on the light emitting layer. Subsequently, after compound EI-1 was deposited as an electron injection layer on the electron transport layer to a thickness of 2 nm, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to produce an OLED. .

[Comparative Example 1] OLED production comprising a compound not according to the present application

An OLED was manufactured in the same manner as in Device Manufacturing Example 1, except that the compound CBP was used as a host for the light emitting layer.

The results of the driving voltage, luminous efficiency based on the 1,000 nit luminance based on the organic electroluminescent device manufactured as described above, and the time until the drop from 100% to 95% based on the 5,000 nit luminance (life: T95) are shown in Table 2 below.

[Table 2]

From Table 2 above, the organic electroluminescent device comprising the compound according to the present application as a host material, has a lower driving voltage and / or higher luminous efficiency and / or longer life than an organic electroluminescent device comprising a conventional organic electroluminescent compound It can be confirmed that it has the characteristics of. In addition, it can be seen that the organic electroluminescent compound of the present application has a high fused structure, so that the glass transition temperature (Tg) is relatively high compared to other organic electroluminescent compounds of similar molecular weight, and thus thermal stability is good.

The compounds used in the device examples and comparative examples are shown in Table 3 below.

[Table 3]

Claims (8)

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

In Chemical Formula 1,
A ₁ to A ₁₁ are each independently N or CR ₁ ;
X ₁ is N, NR ₃ or CR ₄ , X ₂ is N or C, provided that at least one of X ₁ and X ₂ includes N;
R ₁ , R ₃ , R ₄ , Ar ₁ and Ar 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 di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tree (C6-C30) arylsilyl, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; Two or more adjacent R ₁ may be connected to each other to form a ring; When there are multiple R _{1 s} , each R ₁ may be the same or different from each other;
L ₁ is each independently a single bond, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-30 membered) heteroarylene, Or a substituted or unsubstituted (C3-C30) cycloalkylene. The substituted (C1-C30) alkyl (alkylene), the substituted (C6-C30) aryl (ren), the substituted (3-30 membered) heteroaryl (ren), and the substituted (C3-C30). ) Cycloalkyl (ren), 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 mono- or di- (C1-C30) alkylamino, substituted mono- or di- (C6-C30) aryl The substituents of amino and 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) cycloal Kenyl, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl substituted or unsubstituted (3-30 membered) heteroaryl, ( 3-30 won) substituted with heteroaryl 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, 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) arylcarbonyl, Di (C1-C30) alkylboronil, (C1-C30) alkyl (C6-C30) arylboronil, (C6-C30) ar (C1-C30) alkyl, and (C1-C30) alkyl (C6- C30) at least one organic electroluminescent compound selected from the group consisting of aryl. According to claim 1, wherein Formula 1 is represented by any one of the following Formulas 2 to 8, an organic electroluminescent compound:
[Formula 2] [Formula 3]

[Formula 4] [Formula 5]

[Formula 6] [Formula 7]

[Formula 8]

In the above formula 2 to 8
Y ₁ is NR ₅ , O, S or CR ₆ R ₇ ;
T ₁ to T ₄ are each independently CR ₈ or N;
R ₁ , R ₂ , and R ₅ to R ₈ 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) alkyl Silyl, 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 mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1) -C30) alkyl (C6-C30) arylamino;
a is each independently an integer of 1 or 2, b and c are each independently an integer of 1 to 4, and d is an integer of 1 to 3;
When R ₁ , R ₂ and R ₈ are each plural, each R ₁ , each R ₂ , and each R ₈ may be the same or different from each other;
A ₁ to A ₁₁ , X ₁ , X ₂ , L ₁ , Ar ₁ and Ar ₂ are as defined in claim 1. According to claim 1, wherein Formula 1 is represented by any one of the following Formulas 11 to 13, an organic electroluminescent compound:
[Formula 11] [Formula 12]

[Formula 13]

In the above formulas 11 to 13,
A ₁ to A ₁₁ , R ₃ , L ₁ , Ar ₁ and Ar ₂ are as defined in claim 1. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of 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, comprising the organic electroluminescent compound as a host material.

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