KR20220063718A - Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present application as a single host material, or comprising a specific combination of compounds according to the present application as a plurality of host materials, it is possible to produce an organic electroluminescent device having higher luminous efficiency.

Description

An organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same

The present invention relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same.

Eastman Kodak's Tang et al. first developed a TPD/Alq3 double-layer low-molecular organic electroluminescent device (OLED) consisting of a light emitting layer and a charge transport layer in 1987. reached Currently, the organic electroluminescent device mainly uses a phosphor having excellent luminous efficiency in realizing a panel. For long-term use and high resolution of the display, an OLED having high luminous efficiency is required.

Meanwhile, Korean Patent Application Laid-Open No. 2019-0033218 discloses an imidazole derivative or a pyrrole derivative compound, but does not specifically disclose a specific compound claimed herein. In addition, there is a need to develop a light emitting material having more improved performance, such as high luminous efficiency and/or improved lifetime characteristics, compared to the specific compound disclosed in the above patent document.

Korean Patent Publication No. 2019-0033218 (published on March 29, 2019)

It is an object of the present application to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. Another object of the present application is to provide an improved organic electroluminescent material capable of providing an organic electroluminescent device having improved luminous efficiency characteristics. Another object of the present application is to provide an organic electroluminescent device having improved luminous efficiency and/or lifetime characteristics by including a compound of a specific combination as a host material.

The present inventors have completed the present invention by discovering that the compound represented by the following formula (1) achieves the above object. The compound represented by Formula 1 of the present application may be applied to an organic electroluminescent device as a single host material or as a plurality of host materials in combination with one or more compounds represented by Formula 2 and/or 3 of the present application.

[Formula 1]

Formula 1 is fused with Formula 11 to form a ring, wherein any two adjacent ones of X ₁ to X ₄ become a carbon atom at the a position and a nitrogen atom at the b position in Formula 11;

Among X ₁ to X ₄ , those not fused with Formula 11 are each independently NR _{1 ,} CR ₂ R ₃ , O, S, P, or P=O;

[Formula 11]

L ₁ and L ₂ are each independently a single bond, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or a substituted or unsubstituted (C6-C30) ) is arylene;

Ar ₁ and Ar ₂ are each independently hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, a substituted or unsubstituted (3-30 membered) heteroaryl, or -N-(Ar ₃ )(Ar ₄ ); provided that, except when both Ar ₁ and Ar ₂ are hydrogen;

Ring A is absent, substituted or unsubstituted (C6-C30) arene, and when ring A is not present, -L ₂ -Ar ₂ is connected to either the x position or the y position, and -(R ₄ ) _c is connected to the other of the x position and the y position;

R ₁ to R ₃ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, R ₂ and R ₃ may be connected to each other to form a spiro ring;

R ₄ and R ₅ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(Ar ₃ )(Ar ₄ ); adjacent R ₄ or adjacent R ₅ may be linked to each other to form a ring;

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

c and d are each independently an integer of 1 to 3, and when a plurality of R ₄ and R ₅ are present, each R ₄ and each R ₅ may be the same or different from each other;

e is an integer of 1 or 2, and when two Ar ₁ are present, each Ar ₁ may be the same as or different from each other.

The organic electroluminescent compound according to the present disclosure exhibits suitable performance for use in organic electroluminescent devices. In addition, by including the compound according to the present application as a single host material or a specific combination of the compound according to the present application as a plurality of host materials, the luminous efficiency and/or lifespan characteristics are improved compared to the conventional organic electroluminescent device. A light emitting device can be obtained.

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

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present application is described in more 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 the 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, an electron injection material, or the like.

As used herein, "a plurality of organic electroluminescent materials" means an organic electroluminescent material comprising a combination of two or more compounds that can be included in any organic material layer constituting the organic electroluminescent device, and is included in the organic electroluminescent device. It can refer to both the material before (eg, before deposition) and after it is included (eg, after deposition). For example, the plurality of organic electroluminescent materials may include one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Two or more compounds that may be included in the above layers may be combined. These two or more compounds may be included in the same layer or different layers through methods used in the art, mixed vapor deposition or co-deposition, or may be deposited separately.

As used herein, the term "plural types of host materials" means a host material including a combination of two or more compounds that can be included in any light emitting layer constituting an organic electroluminescent device, before being included in the organic electroluminescent device (for example, For example, it may refer to both a material before deposition) and after being included (eg, after deposition). As an example, the plurality of types of host materials of the present application is a combination of two or more types of host materials, and may optionally further include a conventional material included in the organic electroluminescent material. Two or more types of compounds included in the plurality of types of host materials of the present application may be included in one light emitting layer or may be included in different light emitting layers, respectively. For example, the two or more kinds of host materials may be mixed vapor deposition or co-evaporation, or may be deposited separately.

As used herein, "(C1-C30)alkyl" means a straight-chain or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein it is preferably 1 to 10 carbon atoms, and 1 to 6 carbon atoms. more preferably. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl and the like. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, preferably 3 to 20 carbon atoms, and 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 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S and cycloalkyl containing one or more heteroatoms selected from N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. As used herein, "(C6-C30) arene" refers to an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. 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 aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, di Benzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluoren]yl, azulenyl, tetramethyldihydrophenanthrenyl, and the like. 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- fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p- tert -butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4" -tert -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] flu Orenyl, 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, 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-di Phenyl-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] fluorenyl, 11 , 11-diphenyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,1 1-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-di Hydro-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, and the like.

As used herein, "(3-50 membered) heteroaryl (ene)" is an aryl group having 3 to 50 ring skeleton atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P or an arylene group. The number of hetero atoms 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 or heteroarylene 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, di Benzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidi nyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzo Pyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, Benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, Benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolephenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl , and fused ring heteroaryls such as dimethylbenzoperiimidinyl, 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-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7 -yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7 -Phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-arc Lidinyl, 2-oxazolyl, 4-oxa Zolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrole-3- Yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methyl Pyrrol-5-yl, 2- tert -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- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -Butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzo Thiophenyl, 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]-benzofuran yl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzo Furanyl, 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-naphtho-[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]-benzofuranyl, 9-naphtho-[2 ,1-b]- Benzofuranyl, 10-naphtho-[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]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2 ,1-b]-benzothiophenyl, 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] pyra Zinyl, 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-silafluoro Renyl, 4-silafluorenyl, 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 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 substituted with a linked group It also includes being For example, "a substituent to which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as one heteroaryl substituent or two heteroaryl substituents connected. As used herein, substituted alkyl, substituted alkenyl, substituted aryl, substituted arene, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl , substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, fused ring group of substituted aliphatic and aromatic rings, substituted mono- or di-alkylamino, substituted mono- or di- Alkenylamino, substituted alkylalkenylamino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted mono- or di-heteroarylamino, substituted alkylheteroarylamino, substituted alkenylaryl The substituents of amino, substituted alkenylheteroarylamino and substituted arylheteroarylamino are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo (C1-C30). )alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl , (3-7 membered) heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, deuterium and (C6-C30)aryl unsubstituted or substituted with one or more (3-30 membered) (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1) unsubstituted or substituted with one or more of heteroaryl, deuterium and (3-30 membered) heteroaryl -C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring group, amino , mono- or di- (C1-C30)alkylamino, mono- or di- (C2-C30)alkenylamino, (C1-C30)alkyl(C2-C30)alkenylamino, mono- or di- (C6 -C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di- (3-30 membered)heteroarylamino, (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)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6- at least one selected from the group consisting of C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. According to one aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C20)alkyl; (C5-C25)cycloalkyl; (5-25 membered) heteroaryl unsubstituted or substituted with (C6-C25)aryl; (C6-C25)aryl unsubstituted or substituted with deuterium, (C1-C10)alkyl and/or (C6-C18)aryl; and mono- or di- (C6-C25)arylamino. According to another aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C10)alkyl; (C5-C20)cycloalkyl; (5-20 membered) heteroaryl unsubstituted or substituted with (C6-C18) aryl; (C6-C20)aryl unsubstituted or substituted with deuterium, (C1-C6)alkyl and/or (C6-C18)aryl; and at least one selected from the group consisting of di(C6-C18)arylamino. For example, the substituent may be deuterium; cyano; methyl; cyclohexyl; phenyl unsubstituted or substituted with one or more selected from the group consisting of deuterium, methyl and tert -butyl; naphthyl; biphenyl; anthracenyl; fluoranthenyl; fluorenyl substituted with phenyl; pyridyl unsubstituted or substituted with phenyl; phenyl-substituted benzimidazolyl; phenoxazine; dibenzofuranyl; And it may be at least one selected from the group consisting of diphenylamino.

As used herein, the ring formed by connecting with adjacent substituents means a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination ring formed by connecting or fusion of two or more adjacent substituents. do. The ring may be preferably a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic or a combination thereof, even more preferably (C6-C18)aryl and ( It may be a (5-25 membered) monocyclic or polycyclic aromatic ring unsubstituted or substituted with one or more of 3-20 membered heteroaryl. 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 N, O and S. For example, the ring may be a benzene ring, a cyclopentane ring, an indane ring, a fluorene ring, a phenanthrene ring, an indole ring, a xanthene ring, or the like.

As used herein, heteroaryl, heteroarylene, and heterocycloalkyl 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 (3-30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1 -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30 ) alkyl (C6-C30) arylamino, 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, and substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino One or more may be combined.

The plurality of host materials of the present disclosure include a first host material and a second host material, wherein the first host material includes a compound represented by Formula 1, and the second host material includes a compound represented by Formula 2 or 3 including compounds. According to an aspect of the present application, the compound represented by Formula 1 and the compound represented by Formula 2 or 3 are different from each other.

Formula 1 is fused with Formula 11 to form a ring, and in this case, any two adjacent ones of X ₁ to X ₄ become a carbon atom at the a position and a nitrogen atom at the b position of the following Formula 11, respectively. For example, X ₁ and X ₂ , X ₂ and X ₃ , and/or X ₃ and X ₄ may be a carbon atom at the a position in Formula 11 and a nitrogen atom at the b position in Formula 11, respectively. In Formula 1, those not fused with Formula 11 among X ₁ to X ₄ are each independently NR _{1 ,} CR ₂ R ₃ , O, S, P, or P=O. According to an aspect of the present application, those not fused with Formula 11 among X ₁ to X ₄ are each independently CR ₂ R ₃ , S or O.

R ₁ to R ₃ 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, Or a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, R ₂ and R ₃ may be connected to each other to form a spiro ring. According to an aspect of the present application, R ₁ to R ₃ are each independently hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted ( 5-25 membered) heteroaryl, and R ₂ and R ₃ may be connected to each other to form a spiro ring. According to another aspect of the present application, R ₂ and R ₃ are each independently hydrogen, unsubstituted (C1-C10)alkyl, or unsubstituted (C6-C18)aryl, which may be connected to each other to form a spiro ring. can For example, R ₂ and R ₃ may each independently be hydrogen, methyl, phenyl, or the like, and R ₂ and R ₃ may be connected to each other to form a spiro fluorene ring.

In Formulas 1 and 11, L ₁ and L ₂ are each independently a single bond, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or a substituted or unsubstituted (C6-C30)arylene. According to an aspect of the present application, L ₁ and L ₂ are each independently a single bond, or a substituted or unsubstituted (C6-C25)arylene. According to another aspect of the present application, L ₁ and L ₂ are each independently a single bond, or an unsubstituted (C6-C18)arylene. For example, L ₁ and L ₂ are each independently a single bond, phenylene, biphenylene, or the like.

In Formulas 1 and 11, Ar ₁ and Ar ₂ are each independently hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, a substituted or unsubstituted (3-30 membered) heteroaryl, or -N-(Ar ₃ )(Ar ₄ ); However, the case where Ar ₁ and Ar ₂ are both hydrogen is excluded. According to one aspect of the present application, Ar ₁ and Ar ₂ are each independently hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, Ar ₁ and Ar ₂ are each independently hydrogen; (C6-C18)aryl unsubstituted or substituted with deuterium; or (5-20 membered)heteroaryl unsubstituted or substituted with one or more of deuterium, (C6-C18)aryl, and 5-20 membered)heteroaryl. For example, Ar ₁ and Ar ₂ are each independently hydrogen, deuterium-substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, substituted triazinyl, phenyl-substituted quinazolinyl, phenyl-substituted quinoxalinyl, etc. may be, The substituent of the substituted triazinyl may be any two selected from the group consisting of phenyl unsubstituted or substituted with deuterium, biphenyl, and dibenzofuranyl.

In Formula 11, ring A is absent or is a substituted or unsubstituted (C6-C30) arene. When the A ring is not present, -L ₂ -Ar ₂ is connected to either the x position or the y position, and -(R ₄ ) _c is connected to the other of the x position or the y position. According to one aspect of the present application, ring A is absent, or is a substituted or unsubstituted (C6-C25) arene. According to another embodiment of the present application, ring A is absent or is an unsubstituted (C6-C18) arene. For example, the A ring may be absent or may be a benzene ring or the like.

In Formulas 1 and 11, R ₄ and R ₅ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(Ar ₃ )(Ar ₄ ); It may be connected to adjacent R ₄ or adjacent R ₅ to form a ring. According to an aspect of the present application, R ₄ and R ₅ are each independently hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, R ₄ and R ₅ are each independently hydrogen or unsubstituted (C6-C20)aryl. For example, R ₄ and R ₅ may each independently be hydrogen, phenyl, or the like.

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

In Formulas 1 and 11, c and d are each independently an integer of 1 to 3, and when a plurality of R ₄ and R ₅ are present, each R ₄ and each R ₅ are the same as or different from each other. can do.

In Formula 1, e is an integer of 1 or 2, and when two Ar ₁ are present, each Ar ₁ may be the same or different from each other.

According to an aspect of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-4 below.

[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

In Formulas 1-1 to 1-4, X ₁ , X ₂ , X ₄ , L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₄ , R ₅ , c, d and e are defined in Formula 1 and same.

The compound represented by Formula 1 may be one or more selected from the following compounds, but is not limited thereto.

The compound represented by Formula 1 according to the present application may be prepared by a synthetic method known to those skilled in the art, for example, may be prepared with reference to the following Schemes 1 and 2, but is not limited thereto.

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, the definition of each substituent is as defined in Formula 1.

Although exemplary synthesis examples of the present invention represented by Formula 1 have been described above, these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Specific synthesis examples based on 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 other than the substituents specified in are bonded.

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 be included in the emission layer, and when included in the emission layer, the compound of Formula 1 may be included as a host material. 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 about 1:99 to about 99:1. When two or more types of 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.

The present application provides a plurality of host materials including a first host material and a second host material, wherein the first host material includes at least one compound represented by Formula 1, and the second host material includes the following Formula It includes at least one of a compound represented by 2 and a compound represented by Formula 3 below.

[Formula 2] [Formula 3]

In Formula 2,

X and Y are each independently -N=, -NR ₁₆ -, -O- or -S-, with the proviso that either one of X and Y is -N= and the other of X and Y is -NR ₁₆ - , -O- or -S-;

R ₆ is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

R ₇ to R ₁₁ and R ₁₆ 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)aryl Silyl, 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 (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, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C6-C30)aryl (3-30 membered)heteroarylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino Or, it may be connected to an adjacent substituent to form a ring,

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

m and f are each independently 1 or 2, g is an integer from 1 to 4; When a plurality of R ₇ to R ₉ are present, each R ₇ to each R ₉ may be the same as or different from each other.

In Formula 3,

T ₁ is a single bond, O or S,

L _a and L _b are each independently a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene,

Ar _a and Ar _b are each independently, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, 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, or substituted or unsubstituted tri(C6 -C30) arylsilyl,

R ₁₂ to R ₁₅ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -50 membered) heteroaryl, 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, fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring group, 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 (C1-C30)alkyl(C6-C30)arylamino, 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, substituted or unsubstituted mono- or di - (C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3-30 membered)heteroarylamino is; It may be linked with an adjacent substituent to form a ring,

h and k are each independently an integer of 1 to 4; i and j are each independently an integer of 1 to 3, and when a plurality of R ₁₂ to R ₁₅ are present, each R ₁₂ to each R ₁₅ may be the same as or different from each other.

In Formula 2, according to an aspect of the present application, any one of X and Y may be -N=, and the other may be -O- or -S-. For example, X may be -N= and Y may be -O- or -S-, or X may be -O- or -S- and Y may be -N=.

In Formula 2, according to one aspect of the present application, R ₆ is a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another embodiment of the present application, R ₆ is unsubstituted (C6-C18)aryl, or unsubstituted (5-20 membered)heteroaryl. For example, R ₆ may be phenyl, biphenylyl, pyridyl, or the like.

In Formula 2, according to an aspect of the present application, R ₇ to R ₁₁ and R ₁₆ are each independently hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3-25 membered) heteroaryl. According to another aspect of the present application, R ₇ to R ₉ are each independently hydrogen, or a substituted or unsubstituted (C6-C18)aryl; R ₁₀ and R ₁₁ are each independently a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. For example, R ₇ to R ₉ may each independently be hydrogen or phenyl; R ₁₀ and R ₁₁ are each independently substituted or unsubstituted phenyl, naphthyl, biphenylyl, phenanthrenyl, dimethyl fluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorene nyl, terphenyl, spirobifluorenyl, (C22)aryl, benzothiophenyl, dibenzothiophenyl, dibenzofuranyl unsubstituted or substituted with phenyl or pyridyl, carbazolyl substituted with phenyl, benzofuropyri dill, benzonaphthofuranyl, benzonaphthothiophenyl, and the like. Substituents of said substituted phenyl are phenyl substituted with one or more deuterium, cyclohexyl, pyridyl substituted with phenyl, phenoxazinyl, diphenylamino, phenyl substituted with one or more methyl, phenyl substituted with tert -butyl, anthra It may be at least one selected from the group consisting of senyl, fluoranthenyl, phenylfluorenyl, and phenyl-substituted benzimidazole.

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

In Formula 2, according to an aspect of the present application, m, f, and g are each independently an integer of 1.

In Formula 3, according to an aspect of the present application, L _a and L _b are each independently a single bond, or a substituted or unsubstituted (C6-C25)arylene. According to another aspect of the present application, L _a and L _b are each independently a single bond or an unsubstituted (C6-C18)arylene. For example, L _a and L _b may each independently be a single bond, naphthylene, biphenylene, or the like.

In Formula 3, according to an aspect of the present application, Ar _a and Ar _b are each independently a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5-25 membered)heteroaryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. According to another aspect of the present application, Ar _a and Ar _b are each independently (C6-C25)aryl unsubstituted or substituted with cyano and/or (C1-C6)alkyl, or unsubstituted tri(C6-C6- C18) arylsilyl. For example, Ar _a and Ar _b are each independently phenyl, naphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, terphenyl, triphenylenyl, unsubstituted or substituted with cyano or methyl; It may be triphenylsilyl and the like.

In Formula 3, according to an aspect of the present application, R ₁₂ to R ₁₅ are each independently hydrogen, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl. According to another aspect of the present application, R ₁₂ to R ₁₅ are each independently hydrogen, unsubstituted (C1-C10)alkyl, unsubstituted (C6-C18)aryl, or (C6-C18)aryl substituted (5-25 won) Heteroaryl. For example, R ₁₂ and R ₁₅ may each independently be hydrogen, methyl, phenyl, or carbazolyl substituted with phenyl, and R ₁₃ and R ₁₄ may each independently be hydrogen.

In Formula 3, according to one aspect of the present application, h to k are each independently an integer of 1.

The compound represented by Formula 2 or 3 may be one or more selected from the following compounds, but is not limited thereto.

At least one of the compounds C-1 to C-95 and at least one of the compounds H-1 to H-171 may be combined to be used in an organic electroluminescent device.

Each of the compounds represented by Formulas 2 and 3 according to the present application may be prepared by a synthetic method known to those skilled in the art. For example, the compound represented by Formula 2 may be prepared with reference to Korean Patent Application Laid-Open Nos. 2017-0022865 (published on Mar. 2, 2017) and No. 2018-0099487 (published on Sep. 5, 2018). The compound represented by Formula 3 may be prepared with reference to Japanese Patent Publication No. 3139321 (published on February 26, 2001), 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). , optionally, it 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 used, but is not limited thereto.

[Formula 101]

In Formula 101,

L is any one 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; Adjacent two or more of R ₁₀₀ to R ₁₀₃ may be connected to each other to form a ring, for example, together with pyridine, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, or 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; Adjacent two or more of R ₁₀₄ to R ₁₀₇ may be connected to each other to form a substituted or unsubstituted ring, for example, together with benzene, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted substituted or unsubstituted dibenzofuran, 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; two or more of R ₂₀₁ to R ₂₂₀ may be connected to each other to form a substituted or unsubstituted 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 present application provides an organic electroluminescent device including the organic electroluminescent compound represented by Formula 1 or a plurality of host materials according to the present application. 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. According to 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.

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 at least one metal selected from the group consisting of group 1, group 2, 4th period transition metal, 5th period transition metal, lanthanide series metal, and d-transition element organometal, 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, on the inner surface of at least one of the pair of electrodes, at least one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter, 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 in each layer, two compounds may be used at the same time. 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 transport 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 positioned between the hole transport layer (or hole injection layer) and the light emitting layer, and may have 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 located 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 light-emitting auxiliary layer, the hole auxiliary layer or the electron blocking layer has 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 light emitting medium. In addition, since the hole transport compound is oxidized to a cation, it is easy to inject and transport holes from the mixing 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, by using the reducing dopant layer as a charge generating layer, it is possible to manufacture an organic electroluminescent device emitting white light having two or more light emitting layers.

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, inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. Any one of the wet film forming methods of 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 the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, the solvent in which the material forming each layer is dissolved or dispersed. It can be, 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-8

1) Synthesis of compound 1-1

In a flask, 2-bromo-1- (bromomethyl) -4-chlorobenzene (30 g, 105.49 mmol), 1H-benzo [d] imidazole-2-thiol (15.8 g, 105.49 mmol), CuI (502 mg, 2.637 mmol), L-proline (607 mg, 5.274 mmol), Cs ₂ CO ₃ (85 g, 263.72 mmol), and N,N-dimethylformamide (DMF) 530 mL were added and dissolved, and then at 130° C. It was refluxed for 6 hours. After the reaction was completed, the mixture was added dropwise to methanol, and the resulting solid was filtered to obtain compound 1-1 (24.9 g, yield: 89%).

2) Synthesis of compound C-8

Compound 1-1 (5 g, 18.36 mmol), Compound A (9.5 g, 22.03 mmol), Pd ₂ dba ₃ (840 mg, 0.918 mmol), Xantphos (1 g, 1.836 mmol), and K ₃ PO ₄ ( 9.7 g, 45.90 mmol) was dissolved in 150 mL of o-xylene, and then refluxed at 180° C. for 6 hours. After cooling to room temperature, distilled water was added. It was extracted with methylene chloride (MC) and dried over magnesium sulfate. It was distilled under reduced pressure and separated by column chromatography to obtain compound C-8 (3.6 g, yield: 36%).

[Example 2] Preparation of compound C-31

Compound 1-1 (5 g, 18.36 mmol), Compound B (7.8 g, 22.03 mmol), Pd ₂ dba ₃ (840 mg, 0.918 mmol), Xantphos (1 g, 1.836 mmol), and K ₃ PO ₄ ( 9.7 g, 45.90 mmol) was dissolved in 150 mL of o-xylene, and then refluxed at 180° C. for 6 hours. The mixture was cooled to room temperature and distilled water was added thereto. It was extracted with methylene chloride (MC) and dried over magnesium sulfate. It was distilled under reduced pressure and separated by column chromatography to obtain compound C-31 (1.1 g, yield: 13%).

[Example 3] Preparation of compound C-83

1) Synthesis of compound 1-2

In a flask, 2-bromo-4-chlorobenzoylchloride (45 g, 177.2 mmol), 2-mercaptobenzoimidazole (20.5 g, 136.31 mmol), CuI (1.3 g, 6.81 mmol), L-proline (1.57) g, 13.63 mmol), and Cs ₂ CO ₃ (22.2 g, 22.2 mmol) were dissolved in 150 mL of o-xylene, and then refluxed at 110° C. for 20 hours. The mixture was cooled to room temperature and distilled water was added thereto. It was extracted with methylene chloride (MC) and dried over magnesium sulfate. After distillation under reduced pressure and separation by column chromatography, compound 1-2 (18.9 g, yield: 46%) was obtained.

2) Synthesis of compound 1-3

In the first flask, 2-iodobiphenyl (18.6 mL, 105.64 mmol) and Mg powder (2.57 g, 105.64 mmol) were dissolved in 40 mL of tetrahydrofuran (THF), and then refluxed at 60° C. for 3 hours. In the second flask, compound 1-2 (23.3 g, 81.26 mmol) was dissolved in 40 mL of THF, added to the reaction mixture in the first flask, and refluxed at 60° C. for 15 hours. The mixture was cooled to room temperature and distilled water was added thereto. It was extracted with methylene chloride (MC) and dried over magnesium sulfate. It was distilled under reduced pressure and separated by column chromatography to obtain compound 1-3 (25 g, overyield).

3) Synthesis of compound 1-4

Compound 1-3 (25 g), 20 mL of triflic acid, and 50 mL of MC were dissolved in a flask and refluxed at 60°C for 15 hours. After cooling to room temperature, distilled water was added. It was extracted with methylene chloride (MC) and dried over magnesium sulfate. It was distilled under reduced pressure and separated by column chromatography to obtain compound 1-4 (5 g, yield: 15%).

4) Synthesis of compound C-83

compound 1-4 (100 mg, 0.23 mmol), compound A (122 mg, 0.28 mmol), Pd ₂ dba ₃ (11 mg, 0.012 mmol), xanthos (13 mg, 0.023 mmol), and K ₃ PO ₄ ( 124 mg, 0.58 mmol) was dissolved in 150 mL of o-xylene, and then refluxed at 180° C. for 6 hours. The mixture was cooled to room temperature and distilled water was added thereto. It was extracted with methylene chloride (MC) and dried over magnesium sulfate. It was distilled under reduced pressure and separated by column chromatography to obtain compound C-83 (100 mg, yield: 61%).

Hereinafter, the luminous efficiency characteristics of the OLED according to the present application will be looked at. However, the following examples only describe the characteristics of the OLED according to the present application for a detailed understanding of the present application, and the present application is not limited to the following examples.

[Device Example 1] Preparation of a green light emitting OLED comprising the compound according to the present application

An OLED device according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (Giomatec) substrate was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropanol and stored before 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 into 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, as a first hole transport layer, compound HT-1 was deposited on the hole injection layer to a thickness of 80 nm. Then, the compound HT-4 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 30 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-8 as a host in one cell in the vacuum deposition equipment, and putting compound D-130 as a dopant in another cell, at the same time, the dopant material is evaporated at different rates so that the dopant is applied to the total amount of the host and the 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 10 wt%. Then, 35 nm of compound ETL-1 : EIL-1 as an electron transport layer was deposited on the light emitting layer in a weight ratio of 40:60. Then, as an electron injection layer, compound EIL-1 was deposited to a thickness of 2 nm on the electron transport layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED device. did For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Comparative Example 1] Preparation of OLED containing a conventional compound as a host

A 40 nm thick light emitting layer was deposited on the second hole transport layer using CBP as a host as a light emitting material and Compound D-130 as a dopant, and Compound Balq was deposited to a thickness of 5 nm as a hole blocking layer. Then, on the hole blocking layer An OLED device was manufactured in the same manner as in Device Example 1, except that 30 nm of the compound ETL-1 : EIL-1 was deposited as an electron transport material in a weight ratio of 40:60.

Table 1 below shows the driving voltage, power efficiency, and emission color based on 1,000 nit luminance of the OLEDs manufactured in Example 1 and Comparative Example 1 prepared as described above.

[Table 1]

[Device Example 2] Green light emitting OLED manufacturing according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that the second hole transport layer, the light emitting layer, and the electron transport layer were deposited as follows. As the second hole transport layer, the compound HT-3 was put into another cell in the vacuum deposition equipment, evaporated by applying an electric current to the cell, and a second hole transport layer having a thickness of 60 nm was deposited on the first hole transport layer. As a light emitting layer, compound C-8 and compound H-131 as hosts were put in two cells in the vacuum deposition equipment, respectively, and compound D-130 as a dopant was put in another cell, and then the two host materials were mixed in a ratio of 1:2 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 the dopant material at different rates to dope the dopant in an amount of 10% by weight with respect to the total amount of the host and the dopant. Then, 35 nm of compound ETL-1 : EIL-1 as an electron transport layer was deposited on the light emitting layer in a weight ratio of 40:60.

[Comparative Example 2] Preparation of an organic electroluminescent device containing a conventional compound as a host

Using compound CBP alone as a host of the light emitting layer, and using compound D-130 as a dopant to deposit a light emitting layer with a thickness of 40 nm on the second hole transport layer, and on the light emitting layer, compound Balq as a hole blocking layer with a thickness of 5 nm An OLED was manufactured in the same manner as in Device Example 2 except that 30 nm of the compound ETL-1 : EIL-1 was deposited as an electron transport layer on the hole blocking layer in a weight ratio of 40:60.

As described above, the driving voltage, luminous efficiency, and emission color of the OLEDs prepared in Device Example 2 and Comparative Example 2 based on 1,000 nit luminance are shown in Table 2 below.

[Table 2]

[Device Example 3] Manufacturing of a red light emitting OLED according to the present application

An OLED was manufactured in the same manner as in Device Example 1, except that the second hole transport layer, the light emitting layer, and the electron transport layer were deposited as follows. As the second hole transport layer, 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. As a light emitting layer, the first host compound and the second host compound described in Table 3 below as hosts were put in two cells in the vacuum deposition equipment, and compound D-39 as a dopant was put into another cell, and then the two host materials were 1: A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by evaporating at a rate of 1 and simultaneously evaporating the 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 dopant. . Then, 35 nm of compound ETL - 1 : EIL - 1 as an electron transport layer was deposited on the light emitting layer at a weight ratio of 50:50.

[Comparative Example 3] Preparation of OLED comprising a comparative compound as a host

An OLED was manufactured in the same manner as in Device Example 3 except that the first host compound described in Table 3 below was used as a host for the light emitting layer.

As described above, the driving voltage, luminous efficiency, and emission color of the OLEDs prepared in Device Example 3 and Comparative Example 3 based on 1,000 nit luminance are shown in Table 3 below.

[Table 3]

From Tables 1 to 3, it can be confirmed that the OLED using the compound represented by Formula 1 of the present application as a host material has excellent driving voltage and/or luminous efficiency characteristics compared to OLEDs using the conventional compound. Furthermore, an OLED using a plurality of host materials including a compound represented by Formula 1 of the present application and a compound represented by Formula 2 or 3 of the present application has a lower driving voltage than an OLED using a conventional compound as a single host material. It can be confirmed that high luminous efficiency is exhibited.

The compounds used in the device examples and comparative examples are shown in Table 4 below.

[Table 4]

The LUMO energy level, HOMO energy level, and triplet energy of the parent nucleus structure of the compound represented by Formula 1 according to an aspect of the present application were measured, respectively, and are shown in Table 5 below.

[Table 5]

With Gaussian16, Gaussian's quantum chemistry calculation program, the structure was optimized by applying the hybrid DFT (Density Functional Theory) B3LYP and 6-31G(d) background sets, and TD-DFT (time dependent DFT) was used to calculate the triplet state.

From Table 5, it can be confirmed that all of the parent nuclei of the compound represented by Formula 1 of the present application have similar HOMO and/or triplet energy levels. For this reason, it is expected that device characteristics similar to those of the above device embodiments will appear even if another compound represented by Formula 1 of the present application is used instead of Compound C-8 .

Claims (7)

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

Formula 1 is fused with Formula 11 to form a ring, wherein any two adjacent ones of X ₁ to X ₄ become a carbon atom at the a position and a nitrogen atom at the b position in Formula 11;
Among X ₁ to X ₄ , those not fused with Formula 11 are each independently NR _{1 ,} CR ₂ R ₃ , O, S, P, or P=O;
[Formula 11]

L ₁ and L ₂ are each independently a single bond, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or a substituted or unsubstituted (C6-C30) ) is arylene;
Ar ₁ and Ar ₂ are each independently hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, a substituted or unsubstituted (3-30 membered) heteroaryl, or -N-(Ar ₃ )(Ar ₄ ); provided that, except when both Ar ₁ and Ar ₂ are hydrogen;
Ring A is absent, substituted or unsubstituted (C6-C30) arene, and when ring A is not present, -L ₂ -Ar ₂ is connected to either the x position or the y position, and -(R ₄ ) _c is connected to the other of the x position and the y position;
R ₁ to R ₃ 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, or a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, R ₂ and R ₃ may be linked to each other to form a spiro ring;
R ₄ and R ₅ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(Ar ₃ )(Ar ₄ ); adjacent R ₄ or adjacent R ₅ may be linked to each other to form a ring;
Ar ₃ and Ar ₄ are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
c and d are each independently an integer of 1 to 3, and when a plurality of R ₄ and R ₅ are present, each R ₄ and each R ₅ may be the same or different from each other;
e is an integer of 1 or 2, and when two Ar ₁ are present, each Ar ₁ may be the same as or different from each other. 2. The substituted alkyl of claim 1, wherein said substituted alkyl, substituted alkenyl, substituted aryl, substituted arene, substituted arylene, substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted The substituents of the dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted aliphatic and aromatic ring fused ring groups are each independently, deuterium, halogen, cyano, carboxyl, nitro, Hydroxy, (C1-C30)alkyl, Halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, ( C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, deuterium and (C6-C30)aryl (C6-C30)aryl, tri (C1-C30) unsubstituted or substituted with one or more of (3-30 membered)heteroaryl, deuterium and (3-30 membered)heteroaryl unsubstituted or substituted with one or more of Alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, (C3-C30) aliphatic ring and (C6-C30) a fused ring group of an aromatic ring, amino, mono- or di- (C1-C30)alkylamino, mono- or di- (C2-C30)alkenylamino, (C1-C30)alkyl ( C2-C30)alkenylamino, mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di- (3-30 membered)heteroarylamino, (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)arylphosphinyl, 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 Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4:
[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

In Formulas 1-1 to 1-4, X ₁ , X ₂ , X ₄ , L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₄ , R ₅ , c, d and e are defined in claim 1 . same as The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

A plurality of host materials including a first host material and a second host material, wherein the first host material includes at least one compound represented by Formula 1 according to claim 1, and the second host material includes A plurality of host materials comprising at least one of a compound represented by Formula 2 and a compound represented by Formula 3 below:
[Formula 2] [Formula 3]

In Formula 2,
X and Y are each independently -N=, -NR ₁₆ -, -O- or -S-, with the proviso that either one of X and Y is -N= and the other of X and Y is -NR ₁₆ - , -O- or -S-;
R ₆ is a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30 membered)heteroaryl,
R ₇ to R ₁₁ and R ₁₆ 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)aryl Silyl, 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 (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, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C6-C30)aryl (3-30 membered)heteroarylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino Or, it may be connected to an adjacent substituent to form a ring,
L ₃ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene,
m and f are each independently 1 or 2, g is an integer from 1 to 4; When a plurality of R ₇ to R ₉ is present, each R ₇ to each R ₉ may be the same as or different from each other;
In Formula 3,
T ₁ is a single bond, O or S,
L _a and L _b are each independently a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene,
Ar _a and Ar _b are each independently, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, 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, or substituted or unsubstituted tri(C6- C30) arylsilyl,
R ₁₂ to R ₁₅ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3 -50 membered) heteroaryl, 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, fused or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring group, 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 (C1-C30)alkyl(C6-C30)arylamino, 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, substituted or unsubstituted mono- or di - (C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C30)aryl (3-30 membered)heteroarylamino is; It may be linked with an adjacent substituent to form a ring,
h and k are each independently an integer of 1 to 4, i and j are each independently an integer of 1 to 3, and when a plurality of R ₁₂ to R ₁₅ are present, each R ₁₂ to each R ₁₅ may be the same as or different from each other. The host material of claim 5, wherein the compound represented by Formula 2 or 3 is selected from the following compounds.

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

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