KR20210116214A - 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 including the same. By including the organic electroluminescent compound according to the present application, it is possible to provide the organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristics and/or power efficiency.

Description

Organic electroluminescent compound and organic electroluminescent device comprising same

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

BACKGROUND ART An electroluminescent device (EL device) is a self-luminous display device, and has an advantage in that a viewing angle is wide, contrast is excellent, and a response speed is fast. [Appl. Phys. Lett. 51, 913, 1987].

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

In the prior art, 4,4'-N,N'-dicarbazole-biphenyl (CBP) was most widely known as a phosphorescent host material. Recently, Bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) ( Balq) has been used as a host material to develop high-performance organic electroluminescent devices.

However, conventional materials have advantages in terms of luminescent properties, but have the following disadvantages: (1) Low glass transition temperature and low thermal stability, which deteriorates during high-temperature deposition under vacuum and reduces device lifespan. (2) In organic EL devices, power efficiency = [(π/voltage) × current efficiency], so power efficiency is inversely proportional to voltage. Although the current efficiency (cd/A) is higher than that of the light emitting device, there is no significant advantage in terms of power efficiency (lm/w) because the driving voltage is also quite high. (3) In addition, when used in an organic electroluminescent device, it is not satisfactory in terms of operating life, and the luminous efficiency is still required to be improved.

Various materials or concepts have been proposed for the organic layer of an organic electroluminescent device in order to improve luminous efficiency, driving voltage, and/or lifetime, but they are not satisfactory for practical use.

Korean Patent Application Laid-Open No. KR2014-0055137A and Korean Patent Application Laid-Open No. KR2015-0126340A disclose fused carbazole derivatives, but the development of organic electroluminescent materials for improving OLED performance is still required.

Korean Patent Publication No. 10-2014-0055137 (published on May 09, 2014) Korean Patent Publication No. 10-2015-0126340 (published on November 11, 2015)

An object of the present application is, firstly, to provide an organic electroluminescent compound effective for manufacturing an organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristics and/or power efficiency, and secondly, to provide an organic electroluminescent compound comprising the organic electroluminescent compound To provide an organic electroluminescent device.

A compound having an aryl moiety may exhibit high stability when used in an electrical device. The present inventors have found by having the compound of the phenanthrene series have a higher HOMO, LUMO and the triplet energy gap (E _T) than any of the anthracene-based compound, by introducing a compound of the phenanthrene series to the organic EL device thus As a result, it was confirmed that the stability was higher than when the anthracene-based compound was introduced. This may be explained by Clar's rule. That is, the higher stability seems to be due to the low bridge conjugation of the phenanthrene structure compared to the anthracene structure and the influence of steric hindrance. More specifically, the present inventors have completed the present invention by discovering that the organic electroluminescent compound represented by the following Chemical Formula 1 achieves the above object.

[Formula 1]

In Formula 1,

Ring A is selected from the following formulas;

X is NR ₁₁ , CR ₁₂ R ₁₃ , O or S;

each R ₁ is independently hydrogen, deuterium, halogen or cyano;

R ₁₁ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered)heterocyclo alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

R ₁₂ and R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3 -7 membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; may combine with each other to form a ring;

R ₂₁ is -L ₁ -Ar ₁ , and when R ₂₁ is plural, each R ₂₁ may be the same as or different from each other;

L ₁ is each 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 (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) )heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

a is an integer from 1 to 4, b is an integer from 1 to 10, and when a and b are an integer of 2 or more, each R ₁ and each R ₂₁ may be the same as or different from each other;

* is a fusion position with a 5-membered ring containing X;

가 아니다.However, when X is NR ₁₁ , the A ring is

is not

By using the organic electroluminescent compound according to the present application, it is possible to manufacture an organic electroluminescent device having a low driving voltage, high luminous efficiency, excellent lifespan characteristics and/or high power efficiency.

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

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present application is described in greater detail below, but it is for illustrative purposes only and should not be construed as limiting the scope of the present application.

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

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, if necessary. For example, the organic electroluminescent material may include 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 or an electron injection material.

The organic electroluminescent material of the present application may include at least one compound represented by Formula 1 above. Although not limited thereto, the compound of Formula 1 may include 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/or an electron injection layer. etc. may be included. Although not limited thereto, the compound of Formula 1 may be included in at least one of the layers constituting the hole transport zone. When the compound of Formula 1 is included in the hole transport layer, the hole auxiliary layer, or the light emission auxiliary layer of the hole transport zone, it may be included as a hole transport material, a hole auxiliary material, or a light emission auxiliary material. In addition, although not limited thereto, when included in the emission layer, the compound of Formula 1 may be included as a host material. Here, the host material may be a host material of a blue, green or red light emitting organic electroluminescent device.

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

As used herein, "(C1-C30)alkyl" means a straight-chain or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl and the like. 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, more preferably 2 to 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbut-2-enyl. 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, more preferably 2 to 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" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, and preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7, preferably 5 to 7, ring skeleton atoms, and the group consisting of B, N, O, S, Si and P, preferably O , S and means a cycloalkyl containing one or more heteroatoms selected from the group consisting of N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. As used herein, “(C6-C30)aryl(ene)” refers to a monocyclic or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, and may be partially saturated. The number of carbon atoms in 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, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azulenyl , tetramethyldihydrophenanthrenyl, and the like. More specifically, examples of the aryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl , benzo [c] phenanthryl, benzo [g] chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl , 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [a] fluorenyl, benzo [b] fluorenyl, benzo [c] fluorenyl, dibenzo fluorenyl, 2 -biphenylyl, 3-biphenylyl, 4-biphenylyl, 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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9 -Fluorantenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl , m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4"-t-butyl-p-terphenyl-4-yl, 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, 11,11-dimethyl-1-benzo [a] fluorenyl, 11,11-dimethyl-2-benzo [a] fluorenyl, 11,11-dimethyl-3-benzo [a] fluorenyl, 11, 11-dimethyl-4-benzo [a] fluorenyl, 11,11-dimethyl-5-benzo [a] fluorenyl, 11,11-dimethyl-6-benzo [a] fluorenyl, 11,11- Dimethyl-7-benzo [a] fluorenyl, 11,11-dimethyl-8-benzo [a] fluorenyl, 11,11-dimethyl-9-benzo [a] fluorenyl, 11,11-dimethyl- 10-benzo[a] fluorenyl, 11,11-dimethyl-1- benzo[b] fluorenyl, 11,11-dimethyl-2-benzo[b] fluorenyl, 11,11-dimethyl-3-benzo[b] fluorenyl, 11,11-dimethyl-4-benzo[ b] fluorenyl, 11,11-dimethyl-5-benzo[b] fluorenyl, 11,11-dimethyl-6-benzo[b] fluorenyl, 11,11-dimethyl-7-benzo[b] Fluorenyl, 11,11-dimethyl-8-benzo[b] fluorenyl, 11,11-dimethyl-9-benzo[b] fluorenyl, 11,11-dimethyl-10-benzo[b] fluorenyl nyl, 11,11-dimethyl-1-benzo [c] fluorenyl, 11,11-dimethyl-2-benzo [c] fluorenyl, 11,11-dimethyl-3-benzo [c] fluorenyl, 11,11-dimethyl-4-benzo [c] fluorenyl, 11,11-dimethyl-5-benzo [c] fluorenyl, 11,11-dimethyl-6-benzo [c] fluorenyl, 11, 11-dimethyl-7-benzo [c] fluorenyl, 11,11-dimethyl-8-benzo [c] fluorenyl, 11,11-dimethyl-9-benzo [c] fluorenyl, 11,11- Dimethyl-10-benzo [c] fluorenyl, 11,11-diphenyl-1-benzo [a] fluorenyl, 11,11-diphenyl-2-benzo [a] fluorenyl, 11,11- Diphenyl-3-benzo [a] fluorenyl, 11,11-diphenyl-4-benzo [a] fluorenyl, 11,11-diphenyl-5-benzo [a] fluorenyl, 11,11 -diphenyl-6-benzo [a] fluorenyl, 11,11-diphenyl-7-benzo [a] fluorenyl, 11,11-diphenyl-8-benzo [a] fluorenyl, 11, 11-diphenyl-9-benzo [a] fluorenyl, 11,11-diphenyl-10-benzo [a] fluorenyl, 11,11-diphenyl-1-benzo [b] fluorenyl, 11 , 11-diphenyl-2-benzo [b] fluorenyl, 11,11-diphenyl-3-benzo [b] fluorenyl, 11,11-diphenyl-4-benzo [b] fluorenyl, 11,11-diphenyl-5-benzo [b] fluorenyl, 11,11-diphenyl-6-benzo [b] fluorenyl, 11,11-diphenyl-7-benzo [b] fluorenyl , 11,11-diphenyl-8-benzo [b] fluorenyl, 11,11-diphenyl-9-benzo [b] fluorenyl, 11,11-diphenyl-10-benzo [b] fluorene Neil, 11,11-dife Nyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,11-diphenyl-3-benzo [c] fluorenyl, 11,11- Diphenyl-4-benzo [c] fluorenyl, 11,11-diphenyl-5-benzo [c] fluorenyl, 11,11-diphenyl-6-benzo [c] fluorenyl, 11,11 -diphenyl-7-benzo [c] fluorenyl, 11,11-diphenyl-8-benzo [c] fluorenyl, 11,11-diphenyl-9-benzo [c] fluorenyl, 11, 11-diphenyl-10-benzo [c] fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl- 9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9, 10-dihydro-4-phenanthrenyl etc. are mentioned.

As used herein, "(3-30 membered) heteroaryl (ene)" refers to an aryl group having 3 to 30 ring skeleton atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P. it means. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein includes a form in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, monocyclic heteroaryl such as pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzo Thiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidi nyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuro Pyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl , benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinox Salinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolephenazinyl, imida and fused ring heteroaryls such as crude pyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imi Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imida Zopyridinyl, 3-pyridinyl, 4-pyridinyl, 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-qui Nolyl, 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-carba Zolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarba Zolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl , 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3 -acridinyl, 4-acridinyl, 9-acridinyl , 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1- Yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methyl Pyrrol-4-yl, 3-methylpyrrol-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-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1 ,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[ 1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho- [1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho -[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naph To-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7- Naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10 -naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl , 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofura nyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-na Pho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3- Naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6 -naphtho- [1,2-b] -benzothiophenyl, 7-naphtho- [1,2-b]-benzothiophenyl, 8-naphtho- [1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl , 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothio Phenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzo Thiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]- Benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b] -benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d] Pyrimidinyl, 6-benzofuro [3,2-d] pyrimidinyl, 7-benzofuro [3,2-d] pyrimidinyl, 8-benzofuro [3,2-d] pyrimidinyl, 9 -benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3 ,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d] Pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[ 3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl , 8-benzothio [3,2-d] pyrazinyl, 9-benzothio [3,2-d] pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluoro Renyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. are mentioned. As used herein, “halogen” includes F, Cl, Br and I atoms.

Also, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative position of a substituent, respectively. Ortho (ortho) indicates that two substituents are adjacent to each other, and for example, when the substituents are at positions 1 and 2 in a benzene substituent, it is referred to as an ortho position. Meta indicates that two substituents are at positions 1 and 3, for example, when a substituent is at positions 1 and 3 in a benzene substituent, it is referred to as a meta position. Para (para) indicates that two substituents are at positions 1 and 4, for example, when the substituents are at positions 1 and 4 in a benzene substituent, it is referred to as a para position.

In addition, 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), and two or more substituents among the substituents are connected It includes those substituted with a group. For example, "a substituent to which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be a heteroaryl or may be interpreted as a substituent in which two heteroaryls are connected. Substituents of substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted silyl, and substituted amino in the formulas herein are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (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 unsubstituted or substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with one or more of (C1-C30)alkyl and (3-30 membered)heteroaryl; 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- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30) arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And at least one selected from the group consisting of (C1-C30)alkyl (C6-C30)aryl, according to one embodiment of the present application, the substituents are each independently (C1-C6)alkyl, (C6-C20)aryl, at least one of (5-15 membered)heteroaryl, di(C6-C12)arylamino and (C1-C6)alkyl(C6-C15)aryl, unsubstituted or substituted with one or more (C6-C15)aryl. Specifically, the substituents are each independently methyl, phenyl, naphthyl, biphenyl, phenanthrenyl, benzophenanthrenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, diphenyltriazinyl, phenylnaph It may be one or more of tiltriazinyl, phenylcarbazolyl and diphenylamino.

In Formula 1, ring A is selected from the following formulas.

According to another aspect of the present application, ring A is selected from the following formulas.

According to another aspect of the present application, ring A is selected from the following formulas.

According to another aspect of the present application, ring A is selected from the following formulas.

In Formula 1, X is NR ₁₁ , CR ₁₂ R ₁₃ , O or S.

where R ₁₁ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one embodiment of the present application, R ₁₁ is a substituted or unsubstituted (C6-C15)aryl, or a substituted or unsubstituted nitrogen-containing (5-15 membered)heteroaryl. According to another aspect of the present application, R ₁₁ is (C6-C15)aryl substituted with at least one of nitrogen-containing (5-15 membered)heteroaryl and di(C6-C12)arylamino; a nitrogen-containing (5-15 membered)heteroaryl substituted with at least one of (C6-C20)aryl and (5-15 membered)heteroaryl. According to another aspect of the present application, _{substituted or unsubstituted (3-30 membered) heteroaryl of R 11} to R ₁₃ are each independently substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolyl, Substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxali nyl, substituted or unsubstituted indenopyridyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuro pyrimidinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. Specifically, R ₁₁ is phenyl substituted with diphenyltriazinyl or diphenylamino; naphthyl substituted with diphenyltriazinyl or phenylnaphthyltriazinyl; phenyl, naphthyl, biphenyl, phenanthrenyl, benzophenanthrenyl, dibenzofuranyl, dibenzothiophenyl and phenylcarbazolyl, triazinyl, quinazolinyl, quinoxalinyl or benzoquinoc salinyl, and the like.

In addition, R ₁₂ and R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino is; They can combine with each other to form a ring. According to an aspect of the present application, R ₁₂ and R ₁₃ are each independently methyl, ethyl or propyl.

In Formula 1, R ₂₁ is -L ₁ -Ar ₁ . When R ₂₁ is plural, each R ₂₁ may be the same as or different from each other.

Here, L ₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene. According to an aspect of the present application, L ₁ is each independently a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5-15 membered)heteroarylene. According to another aspect of the present application, _{each L 1} is independently a single bond, (C6-C15) arylene unsubstituted or substituted with one or more (C6-C15) aryl, or unsubstituted (5-15 membered) hetero is arylene. According to another aspect of the present application, L ₁ is each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naph thylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted fluorenylene, or substituted or unsubstituted pyridylene. Specifically, _{each L 1} may independently be a single bond, phenylene, naphthylene, biphenylene, phenyl substituted with phenyl, pyridylene, or the like.

In addition, Ar ₁ is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3- 7 membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to an aspect of the present application, Ar ₁ is each independently hydrogen, a substituted or unsubstituted nitrogen-containing (5-15 membered) heteroaryl, or a substituted or unsubstituted amino. According to another aspect of the present application, Ar _One Each independently hydrogen; (5-15 membered)heteroaryl substituted with one or more of (C6-C15)aryl, (5-15 membered)heteroaryl and (C1-C6)alkyl(C6-C15)aryl; or (C6-C15)aryl, (5-15 membered)heteroaryl and (C1-C6)alkyl(C6-C15)aryl substituted amino. According to another aspect of the present application, _{substituted or unsubstituted (3-30 membered) heteroaryl of Ar 1} is each independently a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted substituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indenopyridyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuropyrimidinyl , substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. Specifically, Ar ₁ are each independently hydrogen; triazinyl, quinazolinyl, quinoxalinyl or benzoquinoxalinyl, substituted with one or more of phenyl, naphthyl, biphenyl, phenanthrenyl, dimethylfluorenyl, dibenzofuranyl and dibenzothiophenyl; amino substituted with one or more of phenyl, naphthyl, biphenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl and phenylcarbazolyl; and the like.

In Formula 1, a is an integer of 1 to 4, b is an integer of 1 to 10, and when a and b are integers of 2 or more, each R ₁ and each R ₂₁ may be the same or different from each other.

According to one embodiment of the present application, R ₁₁ is a substituted or unsubstituted (C6-C15)aryl, or a substituted or unsubstituted nitrogen-containing (5-15 membered)heteroaryl; L ₁ is each independently a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5-15 membered)heteroarylene; Each Ar ₁ is independently hydrogen, a substituted or unsubstituted nitrogen-containing (5-15 membered) heteroaryl, or a substituted or unsubstituted amino.

According to another embodiment of the present application, R ₁₁ is (C6-C15)aryl substituted with one or more of nitrogen-containing (5-15 membered)heteroaryl and di(C6-C12)arylamino; a nitrogen-containing (5-15 membered)heteroaryl substituted with at least one of (C6-C20)aryl and (5-15 membered)heteroaryl, and L ₁ is each independently a single bond, one or more (C6-C15)aryl is an unsubstituted (C6-C15)arylene, or an unsubstituted (5-15 membered)heteroarylene, Ar ₁ are each independently hydrogen; (5-15 membered)heteroaryl substituted with one or more of (C6-C15)aryl, (5-15 membered)heteroaryl and (C1-C6)alkyl(C6-C15)aryl; or (C6-C15)aryl, (5-15 membered)heteroaryl and (C1-C6)alkyl(C6-C15)aryl substituted amino.

In the present formula, when adjacent substituents are linked to each other to form a ring, or when two adjacent substituents are linked to each other to form a ring, the ring is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, It may be an aromatic ring or a combination thereof. In addition, the ring formed may comprise one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from nitrogen, oxygen and sulfur. According to one aspect of the present application, the number of ring skeleton atoms is (5 to 20 members), and according to another aspect of the present application, the number of ring skeleton atoms is (5 to 15 members). For example, the fused ring may be 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 acyclic 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 substituted Or it may be in the form of an unsubstituted carbazole ring.

In the formula herein, heterocycloalkyl and heteroaryl(ene) may each independently include one or more heteroatoms selected from B, N, O, S, Si and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (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 substituents selected from the group consisting of amino may be bonded.

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

The compound of Formula 1 according to the present application may be prepared by a synthetic method known to those skilled in the art, for example, as shown in Schemes 1 to 7 below.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

[Scheme 5]

[Scheme 6]

[Scheme 7]

In Schemes 1 to 7, X, R ₁ , L ₁ , Ar ₁ and a are the same as defined in Formula 1, and Hal is halogen.

Although exemplary synthesis examples of the present invention represented by Formula 1 have been described above, these are all Suzuki cross-coupling reaction, Wittig reaction, Miyaura borylation reaction, Ullmann reaction, Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H- mont-mediated etherification reaction, 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 It will be readily understood by those skilled in the art that the reaction proceeds even if other substituents defined in Formula 1 are combined in addition to the substituents specified in the specific synthesis examples.

The hole transport band of the present application may be composed of one or more layers from the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer, and a hole auxiliary layer, and each of the layers may consist of one or more layers.

According to one aspect of the present application, the hole transport zone includes a hole transport layer. In addition, the hole transport zone may include a hole transport layer, and may further include one or more layers of a hole injection layer, an electron blocking layer, and a hole auxiliary layer.

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

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

The organic electroluminescent compound of Formula 1 of the present application includes the light emitting layer, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emission auxiliary layer, the electron transport layer, the electron buffer layer, the electron injection layer, the interlayer (interlayer), the hole blocking layer and It may be included in one or more layers of the electron blocking layer. In some cases, preferably, it may be included in the light emitting layer. When used in the light emitting layer, the organic electroluminescent compound of Formula 1 of the present application may be included as a host material. Preferably, the light emitting layer may further include one or more dopants. If necessary, the organic electroluminescent compound herein can be used as a co-host material. That is, the light emitting layer may further include an organic electroluminescent compound other than the organic electroluminescent compound (first host material) of Formula 1 of the present application as a second host material. In this case, the weight ratio of the first host material to the second host material is in the range of 1:99 to 99:1. When two or more materials are included in one layer, they may be mixed and deposited to form a layer, or may be separately and simultaneously co-deposited to form a layer.

In one embodiment of the present application, when the organic electroluminescent compound of Formula 1 of the present application is included in the emission layer, the emission layer may further include a compound represented by Formula 2 below.

[Formula 2]

In Formula 2,

X ₁ and Y ₁ are each independently -N=, -NR ₇ -, -O- or -S-, with the proviso that any one of _{X 1} and Y ₁ is -N=, and the other of _{X 1 and Y 1} one is -NR ₇ -, -O- or -S-;

R' is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

R ₂ to R ₇ 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 a fused ring group of an unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono - or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30) Alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) hetero arylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be linked with adjacent substituents to form a ring;

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

f is 1, g and h are each independently 1 or 2, i is an integer from 1 to 4, and when g to i are an integer of 2 or more, each of R ₂ to R ₄ may be the same or different from each other. .

In Formula 2, X ₁ and Y ₁ are each independently -N=, -NR ₇ -, -O- or -S-, with the proviso _{that any one of X 1} and Y ₁ is -N=, and X ₁ and the other of _{Y 1 is -NR 7} -, -O- or -S-. In addition, according to another aspect of the present application _{, any one of X 1} and Y ₁ may be -N=, and the other may be -O- or -S-. For example, X ₁ may be -N= and Y ₁ may be -O-, X ₁ may be -O- and Y ₁ may be -N=, or X ₁ may be -S- and Y ₁ may be -N=. In Formula 2, R' is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl. According to an aspect of the present application, R' is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, R' is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-20 membered)heteroaryl, for example, unsubstituted phenyl, unsubstituted unsubstituted biphenyl, unsubstituted naphthyl, methyl-substituted fluorenyl, methyl-substituted benzofluorenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, spiro[fluorene-fluorene ]yl, spiro[fluorene-benzofluoren]yl, or unsubstituted pyridyl.

In Formula 2, R ₂ to R ₇ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6 -C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3 -30 membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be linked to adjacent substituents to form a ring. According to an aspect of the present application, R _{2 To} R ₇ are each independently hydrogen, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (3-25 membered) heteroaryl, or a substituted or unsubstituted It may be mono- or di- (C6-C25) arylamino, or may be connected to an adjacent substituent to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, and the formed alicyclic or A carbon atom of the aromatic ring may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur. According to another aspect of the present application, R ₂ to R ₇ are each independently hydrogen, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, a substituted or unsubstituted di(C6-C18)arylamino, substituted or unsubstituted mono- or di-(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino Or, they may be connected to each other to form a substituted or unsubstituted (C3-C25) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring is at least one selected from nitrogen and sulfur. may be replaced by a heteroatom, and the heteroaryl may include one or more heteroatoms selected from B, N, O, S, Si and P. Specifically, R', R ₅ and R ₆ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyri dill, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted Benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted Benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl. For example _{, at least one of R 5} and R ₆ is each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p- biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or It may be at least one selected from the group consisting of substituted or unsubstituted benzofluorenyl. For example, R' can be phenyl, biphenyl, or pyridyl; R ₂ and R ₃ may be hydrogen; R ₄ may be hydrogen or phenyl; R ₅ and R ₆ are each independently substituted phenyl, naphthyl, biphenyl, phenanthrenyl, dimethyl fluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorenyl, terphenyl , spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl, dibenzofuranyl substituted or unsubstituted with phenyl, carbazolyl substituted with phenyl, or benzonaphthofuranyl; The substituent of the substituted phenyl is phenyl substituted with one or more of deuterium, methyl and tert-butyl; anthracenyl; fluoranthenyl; phenylfluorenyl; cyclohexyl; pyridyl substituted with phenyl; phenoxazine; and phenyl-substituted benzimidazolyl.

In Formula 2, f is 1 or 2, preferably 1; g and h are each independently 1 or 2, preferably 1; i is an integer of 1 to 4, preferably 1 or 2. When g to i are an integer of 2 or more, each of R ₂ to R ₄ may be the same as or different from each other.

In Formula 2, L' is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene. According to an aspect of the present application, L' is a single bond, or a substituted or unsubstituted (C6-C18)arylene. According to another aspect of the present application, L' is a single bond or an unsubstituted (C6-C12)arylene. For example, L' may be a single bond or unsubstituted phenylene.

The compound represented by Formula 2 may be specifically exemplified as the following compound, but is not limited thereto.

In another embodiment of the present application, when the organic electroluminescent compound of Formula 1 of the present application is included in the emission layer, the emission layer may further include a compound represented by Formula 3 below.

[Formula 3]

In Formula 3,

HAr is substituted or unsubstituted, nitrogen-containing (3-20 membered) heteroaryl;

L ₂ is each independently a substituted or unsubstituted (C6-C30)arylene;

Ar ₂ is each independently a substituted or unsubstituted (C6-C30)aryl, or Formula 4 below, provided that _{at least one Ar 2} is Formula 4;

[Formula 4]

Y is O, S, CR ₄₁ R ₄₂ , N-* or NR ₄₃ ;

R ₄₁ to R ₄₃ are each independently a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl, or R ₄₁ and R ₄₂ may be bonded to each other to form a ring; ;

R ₃₁ to R ₃₈ are each independently a position connected to _{L 2 ;} 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 substituted (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 (C3-C30) a fused ring group of an aliphatic ring of (C6-C30) and an aromatic ring of -L ₄ -N(Ar ₃ )(Ar ₄ ); may be joined with adjacent substituents to form a ring;

L ₄ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₃ and Ar ₄ are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl;

d is an integer from 1 to 3, and when d is an integer of 2 or more, each ((L ₂ ) _e -Ar ₂ ) may be the same as or different from each other;

e is an integer from 0 to 2, and when e is 2, each L ₂ may be the same or different from each other,

* indicates a position connected to _{L 2 .}

In Formula 3, HAr is a substituted or unsubstituted, nitrogen-containing (3-20 membered) heteroaryl. According to one aspect of the present application, HAr is a substituted or unsubstituted, nitrogen-containing (3-15 membered) heteroaryl. According to another aspect of the present application, HAr is an unsubstituted nitrogen-containing (5-15 membered) heteroaryl. Specifically, HAr is pyridyl, pyrimidinyl, triazinyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pyridopyrazinyl, benzoquinazolinyl, benzoquinoxalinyl, benzofuropyrimidinyl etc.

In Formula 3, L ₂ is each independently a substituted or unsubstituted (C6-C30)arylene. According to an aspect of the present application, L ₂ is each independently a substituted or unsubstituted (C6-C20)arylene. According to another aspect of the present application, L ₂ is each independently an unsubstituted (C6-C20)arylene. Specifically, L ₂ may each independently be phenylene, naphthylene, biphenylene, benzophenanthrenylene, or the like.

In Formula 3, Ar ₂ is each independently a substituted or unsubstituted (C6-C30)aryl, or Formula 4, provided that at least one of _{Ar 2 is Formula 4.} According to an aspect of the present application, Ar ₂ is each independently (C6-C12) aryl substituted with (5-15 membered) heteroaryl substituted with (C6-C30) aryl; (C6-C30)aryl substituted with di(C6-C12)arylamino; unsubstituted (C6-C30)aryl; or Formula 4. Specifically, Ar ₂ is each independently phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, chrysenyl, benzophenanthrenyl unsubstituted or substituted with phenyl , phenyl substituted with phenylquinoxalinyl, phenyl substituted with diphenylamino, etc., or may be of Formula 4.

In Formula 4, Y is O, S, CR ₄₁ R ₄₂ , N-* or NR ₄₃ , and * represents a position connected to _{L 2 .}

In Formula 4, R ₄₁ to R ₄₃ are each independently a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl, or R ₄₁ and R ₄₂ are bonded to each other to form a ring can form. According to one embodiment of the present application, R ₄₁ to R ₄₃ are each independently a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl, or R ₄₁ and R ₄₂ are bonded to each other to form a ring. According to another aspect of the present application, R ₄₁ to R ₄₃ are each independently unsubstituted (C1-C6)alkyl, or unsubstituted (C6-C12)aryl, or R ₄₁ and R ₄₂ are bonded to each other to form a ring. can be formed Specifically, R ₄₁ to R ₄₃ may be each independently methyl, phenyl, or the like, or R ₄₁ and R ₄₂ may be bonded to each other to form a fluorene ring.

In Formula 4, R ₃₁ to R ₃₈ are each independently a position connected to _{L 2 ;} 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 substituted (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 (C3-C30) a fused ring group of an aliphatic ring of (C6-C30) and an aromatic ring of -L ₄ -N(Ar ₃ )(Ar ₄ ); It may be linked with an adjacent substituent to form a ring. According to an aspect of the present application, R ₃₁ to R ₃₈ are each independently a position connected to _{L 2 ;} hydrogen or substituted or unsubstituted (C6-C20)aryl; It may be linked with an adjacent substituent to form a ring. According to another aspect of the present application, R ₃₁ to R ₃₈ are each independently a position connected to _{L 2 ;} hydrogen or unsubstituted (C6-C18)aryl; It may be linked with an adjacent substituent to form a ring. For example, R ₃₁ to R ₃₈ are each independently a position connected to _{L 2 ;} hydrogen, phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl and the like; It may be linked with an adjacent substituent to form a benzene ring.

L ₄ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene.

wherein Ar ₃ and Ar ₄ are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, or substituted or unsubstituted (C3-C30) aliphatic A fused ring group of a ring and an aromatic ring of (C6-C30), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl.

In Formula 3, d is an integer of 1 to 3, and when d is an integer of 2 or more, each ((L ₂ ) _e -Ar ₂ ) may be the same as or different from each other. For example, d may be 2 or 3, and each ((L ₂ ) _e -Ar ₂ ) may be the same or different from each other.

In Formula 3, e is an integer of 0 to 2, and when e is 2, each L ₂ may be the same as or different from each other.

The compound represented by Formula 3 may be specifically exemplified as the following compound, but is not limited thereto.

As a dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants may be used, and a phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present application 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). , in some cases, preferably, may be an ortho-metalation complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases, more preferably, ortho-metalated iridium complex compounds.

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

[Formula 101]

In Formula 101,

L is selected from the following structures 1 to 3;

[Structure 1] [Structure 2] [Structure 3]

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium and/or 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; It may be linked with adjacent substituents to form a ring, for example, together with pyridine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothieno pyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; It may be linked with adjacent substituents to form a ring, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzo together with benzene furan, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;

R ₂₀₁ to R ₂₂₀ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted cyclic (C6-C30)aryl; may be linked with adjacent substituents to form a ring;

s is an integer from 1 to 3.

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

The organic electroluminescent device according to 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 and second electrodes may be an anode and the other may be a cathode. The organic layer includes a light emitting layer, and is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission 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 floors. Each of the above layers may further consist of several layers.

Each of the first electrode and the second electrode may 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-sided emission type. Also, the hole injection layer may be further doped with a p-dopant, and the electron injection layer may be further doped with an n-dopant.

According to one aspect of the present application, the organic electroluminescent device of the present application may further include an azine-based compound as one or more of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material in addition to the organic electroluminescent compound of the present application.

At least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound may be further included in the organic layer.

In addition, in the organic electroluminescent device of the present application, the organic material layer is one or more metals selected from the group consisting of group 1, group 2, 4th period transition metal, 5th period transition metal, lanthanum series metal, and organometal of d-transition element, Alternatively, it may further include one or more complex compounds containing these metals.

In addition, the organic electroluminescent device of the present application may emit white light by further including at least one light emitting layer including a blue, red, or green light emitting compound known in the art in addition to the compound of the present application. In addition, if necessary, it may further include a yellow or orange light emitting layer.

In the organic electroluminescent device of the present application, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer on the inner surface of at least one of the pair of electrodes (hereinafter, these are referred to as "surface layers") ) is preferred. Specifically, it is preferable to arrange a chalcogenide (including oxide) layer of silicon and aluminum on the surface of the anode on the side of the light emitting medium layer, and a metal halide layer or metal oxide layer on the surface of the cathode on the side of the light emitting medium layer. Drive stabilization of an organic electroluminescent element can be obtained by the said surface layer. Preferred examples of the chalcogenide include SiO _X (1≤X≤2), AlO _X (1≤X≤1.5), SiON, SiAlON, and the like, and preferred examples of the metal halide include LiF, MgF ₂ , CaF ₂ , fluoride and rare earth metals, and preferred examples of the metal oxide include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

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. In the hole injection layer, a plurality of layers may be used for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and for each layer, two compounds may be used simultaneously. A hole transport layer or an electron blocking layer may also be used in a plurality of layers.

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 for each layer at the same time. A plurality of layers may be used for the hole blocking layer or the electron transporting layer, and a plurality of compounds may be used for each layer.

The light emitting auxiliary layer is located between the anode and the light emitting layer or between the cathode and the light emitting layer. When used for a purpose or located between the cathode and the light emitting layer, it may be used to facilitate injection and/or transfer of electrons or to block overflow of holes. In addition, the hole auxiliary layer is located between the hole transport layer (or hole injection layer) and the light emitting layer, and may exhibit an effect of smoothing or blocking the transport rate (or injection rate) of holes, and thus charge balance (charge balance) ) can be controlled. In addition, the electron blocking layer is positioned between the hole transport layer (or hole injection layer) and the light emitting layer, and blocks the overflow of electrons from the light emitting layer to trap excitons in the light emitting layer to prevent light emission leakage. When the hole transport layer includes two or more layers, the additionally included layer may be used as the hole auxiliary layer or the electron blocking layer. The hole auxiliary layer and the electron blocking layer have an effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

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 a pair of electrodes. In this way, since the electron transport compound is reduced to an anion, it is easy to inject and transfer electrons from the mixed region to the luminescent medium. In addition, since the hole transport compound is oxidized to a cation, it is easy to inject and transport holes from the mixed region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device emitting white light having two or more light emitting layers can be manufactured by using a reducing dopant layer as a charge generating layer.

The organic electroluminescent material according to an example of the present application may be used as a light emitting material for a white organic light emitting device (White Organic Light Emitting Device). The white organic EL device is a side-by-side method, a stacking method, depending on the arrangement of R (red), G (green) or YG (yellow green), B (blue) light emitting units , or various structures such as a color conversion material (CCM) method have been proposed. In addition, the organic electroluminescent material according to an example of the present application may be used in an organic electroluminescent device including quantum dots (QD).

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, ink jet printing, spin coating, dip coating, flow coating, etc. Any one of the wet film-forming methods can be applied. When the first host compound and the second host compound of the present application are formed into a film, a co-deposition or mixed vapor deposition is performed.

In the case of the wet film forming method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, which solvent dissolves or disperses the material forming each layer. may be used, and any one may be used as long as there is no problem in the film-forming property.

In addition, by using the organic electroluminescent device of the present application, a display device, for example, a display device for a smartphone, tablet, notebook, PC, TV or vehicle, or a lighting device, for example, an outdoor or indoor lighting device is manufactured. it is possible to do

Hereinafter, for a detailed understanding of the present application, a method for preparing a compound according to the present application and physical properties thereof are shown for a representative compound of the present application. However, the present invention is not limited to the following examples.

[Example 1] Preparation of compound C-686

Synthesis of compound 1-1

In a flask, 1-bromo-2-naphthaldehyde (20.0 g, 85.1 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-carbazole (26.2 g, 51.5 mmol), tetrakis(triphenylphosphine)palladium(0) (2.95 g, 2.55 mmol), NaOH (4.12 g, 255 mmol), tetrahydrofuran (THF) 360 mL and After adding 90 mL of H ₂ O, the mixture was stirred under reflux at 90° C. for 1.5 hours. After completion of the reaction, the mixture _{was neutralized with an aqueous NH 4} Cl solution, extracted with methylene chloride (MC), and dried over _{MgSO 4 .} Then, the resultant solid was separated by column chromatography, added with MeOH, and the resulting solid was filtered under reduced pressure to obtain compound 1-1 (20.0 g, yield: 73%).

Synthesis of compound 1-2

Compound 1-1 (19.0 g, 59.1 mmol), (methoxymethyl)triphenylphosphonium chloride (30.4 g, 88.7 mmol) and 300 mL of THF were stirred in a flask at 0° C. while stirring at 0° C. K- dissolved in THF 33.3 mL of Ot-Bu 1 M solution was added dropwise. After stirring for 3 hours _{, neutralized with NH 4} Cl, extracted with MC, and dried _{over MgSO 4 .} Thereafter, the resultant solid was separated by column chromatography, added with MeOH, and the resulting solid was filtered under reduced pressure to obtain Compound 1-2 (20.0 g, yield: 97%).

Synthesis of compound 1-3

Compound 1-2 (66.3 g, 191 mmol), 34 mL of Eaton's reagent, and 950 mL of chlorobenzene were placed in a flask and stirred under reflux at 180° C. overnight. After completion of the reaction, the mixture _{was neutralized with NaHCO 3} , extracted with MC, and dried over _{MgSO 4 .} Thereafter, the resultant solid was separated by column chromatography, added with MeOH, and the resulting solid was filtered under reduced pressure to obtain compound 1-3 (27 g, yield: 45%).

Synthesis of compound C-686

Compound 1-3 (10.0 g, 11 mmol), 2-chloro-3-phenyl-quinoxaline (7.6 g, 31.5 mmol), Cs ₂ CO ₃ (10.3 g, 31.5 mmol), dimethylaminopyridine (DMAP) in a flask (1.92 g, 0.0158 mmol) and 60 mL of dimethyl sulfoxide (DMSO) were added, followed by stirring at 100° C. for 4 hours. After completion of the reaction, H ₂ O was added to the mixture, the resulting solid was separated by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound C-686 (1.3 g, yield: 8%).

[Example 2] Preparation of compound C-700

In a flask, compound 1-3 (5.0 g, 15.8 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (6.71 g, 17.3 mmol), CuSO ₄ ( 1.0 g, 6.30 mmol), K ₂ CO ₃ (4.35 g, 31.5 mmol) and 80 mL of o-dichlorobenzene (o-DCB) were added, and the mixture was stirred under reflux at 180° C. overnight. After completion of the reaction, MeOH was added to the mixture to form a solid, which was again _{dissolved in CHCl 3} and separated by column chromatography. MeOH was added and the resulting solid was filtered under reduced pressure to obtain Compound C-700 (2.0 g, yield: 20%). got it

[Example 3] Preparation of compound C-589

Synthesis of compound 3-1

In a flask, 5-bromobenzo [b] naphtho [1,2-d] thiophene (50.0 g, 160 mmol), 4,4,4',4',5,5,5',5'-octa Methyl-2,2'-bi(1,3,2-dioxaborolane) (48.6 g, 192 mmol), PdCl ₂ (PPh ₃ ) ₂ (5.60 g, 7.98 mmol), KOAc (39.2 g, 399 mmol) ) and 800 mL of 1,4-dioxane were added, followed by stirring under reflux at 130° C. for 2 hours. After completion of the reaction, after separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound 3-1 (41.3 g, Yield: 72%).

Synthesis of compound 3-2

In a flask, compound 3-1 (40.3 g, 112 mmol), 2-bromo-5-chloro-benzaldehyde (25.8 g, 117 mmol), tetrakis(triphenylphosphine)palladium(0) (3.88 g, 3.36 mmol) ), NaOH (13.4 g, 336 mmol), 450 mL of THF and _{150 mL of H 2} O were added, followed by stirring under reflux at 130° C. for 2 hours. After completion of the reaction, neutralized with an aqueous HCl solution, extracted with EA, and dried over _{MgSO 4 .} After separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound 3-2 (26.0 g, yield: 62.3%).

Synthesis of compound 3-3

In a flask, compound 3-2 (25.0 g, 67.0 mmol), (methoxymethyl)triphenylphosphonium chloride (34.6 g, 101 mmol) and 340 mL of THF were stirred at 0°C, and K- dissolved in THF was stirred at 0°C. 101 mL of Ot-Bu 1 M solution was added dropwise. After stirring for 3 hours _{, neutralized with NH 4} Cl, extracted with MC, and dried _{over MgSO 4 .} Thereafter, the resultant solid was separated by column chromatography, added with MeOH, and the resulting solid was filtered under reduced pressure to obtain compound 3-3 (37.0 g, yield: 138%).

Synthesis of compound 3-4

In a flask, compound 3-3 (36.0 g, 89.8 mmol) was dissolved in 450 mL of MC, stirred at 0°C, and _{34 mL of BF 3} ·EtOEt was added dropwise thereto. After completion of the reaction, the mixture _{was neutralized with NaHCO 3} , extracted with MC, and dried over _{MgSO 4 .} Then, the resultant solid was separated by column chromatography, added with MeOH, and the resulting solid was filtered under reduced pressure to obtain Compound 3-4 (18.7 g, Yield: 56.5%).

Synthesis of compound C-589

Compound 3-4 (4.50 g, 12.2 mmol), N-phenyldibenzofuran-3-amine (3.32 g, 12.8 mmol), Pd ₂ (dba) ₃ (0.559 g, 0.610 mmol), s-phos ( 0.501 g, 1.22 mmol), NaOt-Bu (2.34 g, 24.4 mmol) and 60 mL of toluene were added, followed by stirring at 140° C. for 2 hours. After completion of the reaction, the reaction was cooled to room temperature, separated by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound C-589 (2.5 g, yield: 34.6%).

[Example 4] Preparation of compound C-101

Synthesis of compound 4-1

Compound 3-4 (9.0 g, 24.4 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-ratio (1,3,2- dioxaborolane) (8.05 g, 31.7 mmol), Pd ₂ (dba) ₃ (1.12 g, 1.22 mmol), s-phos (1.00 g, 2.44 mmol), KOAc (7.18 g, 73.2 mmol) and 1,4 - After adding 110 mL of dioxane, it was stirred under reflux at 130 °C for 2 hours. After completion of the reaction, after separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound 4-1 (10.0 g, Yield: 89%).

Synthesis of compound C-101

In a flask, compound 4-1 (5.0 g, 10.9 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.22 g, 10.9 mmol), tetrakis ( Triphenylphosphine) palladium (0) (0.627 g, 0.543 mmol), K ₂ CO ₃ (3.75 g, 27.2 mmol), toluene 50.0 mL, EtOH 25.0 mL and H ₂ O 25.0 mL were added, and then at 140° C. for 2 hours. while stirring at reflux. After completion of the reaction, the solution was diluted by adding water, extracted with EA, and dried over _{MgSO 4 .} After separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound C-101 (3.0 g, Yield: 43.0%).

[Example 5] Preparation of compound C-715

Synthesis of compound 5-1

In a flask, 4-chloronaphtho[1,2-b]benzofuran (50.0 g, 198 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2 '-Ratio (1,3,2-dioxaborolane) (65.3 g, 257 mmol), Pd ₂ (dba) ₃ (9.06 g, 9.89 mmol), s-phos (8.13 g, 19.8 mmol), KOAc ( 58.3 g, 399 mmol) and 1000 mL of 1,4-dioxane were added and stirred under reflux at 130° C. for 3 hours. After completion of the reaction, after separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound 5-1 (51.2 g, yield: 75%).

Synthesis of compound 5-2

In a flask, compound 5-1 (50.2 g, 146 mmol), 2-bromo-5-chloro-benzaldehyde (33.6 g, 153 mmol), tetrakis(triphenylphosphine)palladium(0) (5.06 g, 4.38 mmol) ), NaOH (17.5 g, 438 mmol), 500 mL of THF and _{250 mL of H 2} O were added, followed by stirring under reflux at 130° C. for 2 hours. After completion of the reaction _{, neutralized with NH 4} Cl aqueous solution, extracted with EA, and dried over _{MgSO 4 .} After separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound 5-2 (36.0 g, yield: 69.1%).

Synthesis of compound 5-3

In a flask, 5-2 (36.0 g, 100.9 mmol), (methoxymethyl)triphenylphosphonium chloride (51.9 g, 151.3 mmol) and 500 mL of THF are stirred at 0 °C and K-Ot dissolved in THF is stirred. 151.3 mL of -Bu 1 M solution was added dropwise. After stirring for 3 hours _{, neutralization with NH 4} Cl, extraction with EA, and drying _{over MgSO 4 .} Thereafter, the resultant solid was separated by column chromatography, added MeOH, and the resulting solid was filtered under reduced pressure to obtain compound 5-3 (38.0 g, yield: 98%).

Synthesis of compound 5-4

Compound 5-3 (37.0 g, 96.1 mmol) was dissolved in MC 550 mL in a flask, stirred at 0° C., and _{251 mL of BF 3} EtOEt was added dropwise thereto. After completion of the reaction, the mixture _{was neutralized with NaHCO 3} , extracted with MC, and dried over _{MgSO 4 .} Thereafter, the resultant solid was separated by column chromatography, added with MeOH, and the resulting solid was filtered under reduced pressure to obtain compound 5-4 (13.6 g, yield: 40.1%).

Synthesis of compound C-715

In a flask, compound 5-4 (4.80 g, 13.6 mmol), N-phenyldibenzofuran-3-amine (3.7 g, 14.3 mmol), Pd ₂ (dba) ₃ (0.559 g, 0.680 mmol), s-phos ( 0.501 g, 1.36 mmol), NaOt-Bu (2.61 g, 27.2 mmol) and 70 mL of o-xylene were added and stirred at 190° C. for 1.5 hours. After completion of the reaction, the mixture was cooled to room temperature, separated by column chromatography, added MeOH, and the resulting solid was filtered under reduced pressure to obtain compound C-715 (3.9 g, yield: 49.8%).

[Example 6] Preparation of compound C-13

Synthesis of compound 6-1

Compound 5-4 (9.0 g, 25.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-ratio (1,3,2- dioxaborolane) (8.43 g, 33.2 mmol), Pd ₂ (dba) ₃ (1.17 g, 1.28 mmol), s-phos (1.05 g, 2.55 mmol), KOAc (7.50 g, 76.5 mmol) and 1,4 - After adding 130 mL of dioxane, it was stirred under reflux at 130 °C for 3 hours. After completion of the reaction, after separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound 6-1 (10.5 g, Yield: 92.7%).

Synthesis of compound C-13

Compound 6-1 (5.0 g, 11.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.03 g, 11.3 mmol), tetrakis(triphenylphosphine)palladium in a flask (0) (0.650 g, 0.563 mmol), K ₂ CO ₃ (3.88 g, 28.1 mmol), toluene 30 mL, EtOH 10 mL, and H ₂ O 10 mL were added, followed by stirring under reflux at 130° C. for 2 hours. After completion of the reaction, it was filtered and dried. After separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound C-13 (2.5 g, Yield: 40.3%).

[Example 7] Preparation of compound C-220

Compound 4-1 (4.7 g, 10.2 mmol), 2-chloro-4- (dibenzo [b,d] furan-1-yl) -6-phenyl-1,3,5-triazine (3.84 g) in a flask , 10.7 mmol), tetrakis(triphenylphosphine)palladium(0) (0.589 g, 0.51 mmol), K ₂ CO ₃ (3.52 g, 25.5 mmol), toluene 30.0 mL, EtOH 10.0 mL and H ₂ O 10.0 mL After adding, the mixture was stirred under reflux at 140 °C for 2 hours. After completion of the reaction, the solution was diluted by adding water, extracted with EA, and dried over _{MgSO 4 .} After separation by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain Compound C-220 (3.6 g, yield: 53.8%).

[Device Manufacturing Example 1] Preparation of a red light emitting OLED according to the present application

OLEDs comprising a compound according to the present disclosure were prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass (Giomatec) substrate for OLED was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropyl alcohol and stored for use. Next, after mounting the ITO substrate on the substrate holder of the vacuum deposition equipment, compound HI-1 is put into one cell in the vacuum deposition equipment, compound HT-1 is put into another cell, and the two materials are evaporated at different rates. A hole injection layer was deposited by doping the compound HI-1 to a thickness of 10 nm in an amount of 3 wt% based on the total amount of the compound HI-1 and the compound HT-1. Then, the compound HT-1 was put into a cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a first hole transport layer having a thickness of 80 nm on the hole injection layer. Then, the compound HT-2 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. After putting compound C-686 as a host in one cell in the vacuum deposition equipment and compound D-39 as a dopant in another cell, the two materials were evaporated at different rates to give the dopant for the total amount of host and dopant. A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by doping in an amount of 3 wt%. Then, on the light emitting layer, a 35 nm-thick electron transport layer was deposited on the light emitting layer by using compound ETL-1 :compound EIL-1 as an electron transport material in a weight ratio of 50:50. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED. . For each material, each compound was purified by vacuum sublimation under ^{10 -6 torr.}

[Device Manufacturing Example 2] Preparation of a red light emitting OLED according to the present application

An OLED was manufactured in the same manner as in Device Preparation Example 1 except that Compound C-700 was used as a host of the light emitting layer.

[Comparative Example] Preparation of OLED containing a comparative compound as a host

An OLED was manufactured in the same manner as in Device Preparation Example 1 except that CBP was used as a host of the light emitting layer.

Until the driving voltage, luminous efficiency, emission color, and light intensity based on 5,000 nit luminance of the organic electroluminescent device of the device manufacturing examples 1 and 2 prepared as described above, and the organic electroluminescent device of the comparative example fall from 100% to 95% The time taken (lifetime: T95) is shown in Table 1 below.

[Table 1]

The organic electroluminescent device using the organic electroluminescent compound according to the present application as a host showed lower driving voltage, higher luminous efficiency, and excellent lifespan characteristics than the organic electroluminescent device using the compound of Comparative Example.

[Device Preparation Examples 3 to 6] Preparation of red light emitting OLED according to the present application

An OLED device according to the present application was manufactured. First, a transparent electrode ITO thin film (10Ω/□) on a glass (Giomatec) substrate for OLED was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropyl alcohol and stored for use. Next, after mounting the ITO substrate in the substrate holder of the vacuum deposition equipment, the compound HI-1 is put into a cell in the vacuum deposition equipment, the compound HT-1 is put in another cell, and the two materials are evaporated at different rates to form the compound A hole injection layer was deposited by doping the compound HI-1 to a thickness of 10 nm in an amount of 3 wt% based on the total amount of HI-1 and compound HT-1. Then, the compound HT-1 was put into a cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a first hole transport layer having a thickness of 80 nm on the hole injection layer. Then, the compound HT-2 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. After putting the first host material and the second host material described in Table 2 below as hosts in each of the two cells in the vacuum deposition equipment, and putting compound D-39 as a dopant in another cell, the two host materials were mixed in a 1:1 ratio. A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by evaporating at a rate and simultaneously evaporating a dopant material at a different rate to dope the dopant in an amount of 3 wt% with respect to the total amount of the host and the dopant. Then, on the light emitting layer, a 35 nm-thick electron transport layer was deposited on the light emitting layer by using compound ETL-1 :compound EIL-1 as an electron transport material in a weight ratio of 50:50. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED. . For each material, each compound was purified by vacuum sublimation under ^{10 -6 torr.}

The time it takes for the driving voltage, luminous efficiency, emission color, and light intensity based on 5,000 nit luminance based on 1,000 nit luminance of the organic electroluminescent device of Device Preparation Examples 3 to 6 manufactured as described above to fall from 100% to 95% ( Lifespan: T95) is shown in Table 2 below.

[Table 2]

The organic electroluminescent device according to the present application showed a low driving voltage, high luminous efficiency, and very good lifespan characteristics.

[Table 3]

Claims (15)

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

In Formula 1,
Ring A is selected from the following formulas;

X is NR ₁₁ , CR ₁₂ R ₁₃ , O or S;
each R ₁ is independently hydrogen, deuterium, halogen or cyano;
R ₁₁ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered)heterocyclo alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;
R ₁₂ and R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3 -7 membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; may combine with each other to form a ring;
R ₂₁ is -L ₁ -Ar ₁ , and when R ₂₁ is plural, each R ₂₁ may be the same as or different from each other;
L ₁ is each 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 (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) )heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;
a is an integer from 1 to 4, b is an integer from 1 to 10, and when a and b are an integer of 2 or more, each R ₁ and each R ₂₁ may be the same as or different from each other;
* is a fusion position with a 5-membered ring containing X;
However, when X is NR ₁₁ , the A ring is

is not The substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted in said R ₁₁ to R ₁₃ , L ₁ and Ar _{1 .} The substituents of heteroarylene, substituted silyl and substituted amino are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (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 unsubstituted or substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with one or more of (C1-C30)alkyl and (3-30 membered)heteroaryl; 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- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30) arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And at least one selected from the group consisting of (C1-C30)alkyl (C6-C30)aryl, an organic electroluminescent compound. The organic electroluminescent compound according to claim 1, wherein the A ring is selected from the following formulas.

The organic electroluminescent compound according to claim 1, wherein the A ring is selected from the following formulas.

The organic electroluminescent compound according to claim 1, wherein the A ring is selected from the following formulas.

The method according to claim 1, wherein L ₁ is each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted fluorenylene, or substituted or unsubstituted pyridylene. The _{substituted or unsubstituted (3-30 membered) heteroaryl of R 11} to R ₁₃ and Ar ₁ are each independently substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinolyl, Substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinolyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxali nyl, substituted or unsubstituted indenopyridyl, substituted or unsubstituted indenopyrimidinyl, substituted or unsubstituted indenopyrazinyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted benzofuro pyrimidinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyridyl, substituted or unsubstituted benzothiopyrimidinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted An organic electroluminescent compound which is carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. The organic electroluminescent compound according to 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 10, comprising the organic electroluminescent compound in a light emitting layer or a hole transport zone. The organic electroluminescent device according to claim 11, wherein when the organic electroluminescent compound is included in the light emitting layer, the light emitting layer further comprises a compound represented by Formula 2 below.
[Formula 2]

In Formula 2,
X ₁ and Y ₁ are each independently -N=, -NR ₇ -, -O- or -S-, with the proviso that any one of _{X 1} and Y ₁ is -N=, and the other of _{X 1 and Y 1} one is -NR ₇ -, -O- or -S-;
R' is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
R ₂ to R ₇ 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 a fused ring group of an unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono - or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30) Alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) hetero arylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be linked with adjacent substituents to form a ring;
L' is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
f is 1, g and h are each independently 1 or 2, i is an integer from 1 to 4, and when g to i are an integer of 2 or more, each of R ₂ to R ₄ may be the same or different from each other. . The organic electroluminescent device according to claim 12, wherein the compound represented by Formula 2 is selected from the following compounds.

The organic electroluminescent device of claim 11, wherein when the organic electroluminescent compound is included in the light emitting layer, the light emitting layer further comprises a compound of Formula 3 below.
[Formula 3]

In Formula 3,
HAr is substituted or unsubstituted, nitrogen-containing (3-20 membered) heteroaryl;
L ₂ is each independently a substituted or unsubstituted (C6-C30)arylene;
Ar ₂ are each independently substituted or unsubstituted (C6-C30)aryl, or Formula 4 below, provided that at least one of _{Ar 2 is Formula 4;}
[Formula 4]

Y is O, S, CR ₄₁ R ₄₂ , N-* or NR ₄₃ ;
R ₄₁ to R ₄₃ are each independently a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl, or R ₄₁ and R ₄₂ may be bonded to each other to form a ring; ;
R ₃₁ to R ₃₈ are each independently a position connected to _{L 2 ;} 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 substituted (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 (C3-C30) a fused ring group of an aliphatic ring of (C6-C30) and an aromatic ring of -L ₄ -N(Ar ₃ )(Ar ₄ ); may be joined with adjacent substituents to form a ring;
L ₄ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₃ and Ar ₄ are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl;
d is an integer from 1 to 3, and when d is an integer of 2 or more, each ((L ₂ ) _e -Ar ₂ ) may be the same as or different from each other;
e is an integer from 0 to 2, and when e is 2, each L ₂ may be the same or different from each other,
* indicates a position connected to _{L 2 .} The organic electroluminescent device according to claim 14, wherein the compound represented by Formula 3 is selected from the following compounds.

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