KR20220013315A - 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 represented by chemical formula 2': Ar_11(L_11-HAr)_e or chemical formula 2": Ar_11(L_11-HAr)_e, a plurality of host materials comprising at least one first host compound and at least one second host compound, and an organic electroluminescent device including the same. By including the organic electroluminescent compound or a compound of a specific combination according to the present application as a host material, it is possible to provide the organic electroluminescent device having improved driving voltage, luminous efficiency, power efficiency and/or lifespan characteristics.

Description

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

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

Eastman Kodak's Tang et al. first developed a TPD/Alq3 double-layer low-molecular green 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. OLEDs having high luminous efficiency and/or long lifespan are required for long-term use and high resolution of the display.

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. Accordingly, there is a continuous need to develop an organic electroluminescent device having improved performance, for example, improved driving voltage, luminous efficiency, power efficiency, and/or lifespan characteristics compared to the previously disclosed organic electroluminescent device.

Meanwhile, Korean Patent Laid-Open Publication No. 2012-0104067 discloses a compound in which a nitrogen-containing heteroaryl is bonded to a benzonaphthothiophene moiety, but does not specifically disclose a host material of a specific combination claimed herein.

Korean Patent Publication No. 2012-0104067 (published on September 20, 2012)

It is an object of the present application to provide compounds of novel structures suitable for use as organic electroluminescent materials. Another object of the present application is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, high power efficiency and/or excellent lifespan characteristics by including a plurality of host materials including a compound of a specific combination. .

As a result of intensive research to solve the above technical problem, the present inventors have completed the present invention by discovering that the organic electroluminescent compound represented by the following Chemical Formula 2' or Chemical Formula 2" achieves the above-described object. In addition, 1 A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula (1), and the second host compound is represented by the following formula (2) Phosphorus, a plurality of types of host materials, has been found to achieve the above object, thereby completing the present invention.

[Formula 2']

In Formula 2',

Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl;

L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₁₁ is each independently any one of Formulas 3 to 5;

[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,

Y ₂ is O or S;

R ₂₀ to R ₂₉ are hydrogen or deuterium;

e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;

* indicates a position connected to L ₁₁ ;

However, when HAr is substituted triazinyl, the substituents of triazinyl are each independently deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, fluoranthenyl, cry senyl, carbazolyl, and combinations thereof, and when there are two substituents, they are the same as or different from each other.

[Formula 2"]

In Formula 2",

Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl , a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl;

L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₁₁ is each independently any one of Formulas 3 to 5;

[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,

Y ₂ is O or S;

R ₂₁ to R ₂₄ and R ₂₆ to R ₂₉ are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

R ₂₀ and R ₂₅ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;

* indicates a position connected to L ₁₁ .

[Formula 1]

In Formula 1,

X ₁ and Y ₁ are each independently -N=, -NR ₅ -, -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 ₅ -, -O- or -S-;

R ₁ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

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

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

R ₂ to 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, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₃ -N(Ar ₃ )(Ar ₄ ); adjacent substituents may be linked to each other to form a ring;

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

[Formula 2]

In Formula 2,

each HAr is independently a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl;

L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₁₁ is each independently any one of Formulas 3 to 5;

[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,

Y ₂ is O or S;

R ₂₀ to R ₂₉ 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 an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₃ -N(Ar ₃ )(Ar ₄ );

e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;

* indicates a position connected to L ₁₁ ;

In Formulas 1 and 3 to 5,

L ₃ is each independently 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; (C6-C30) is a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.

The organic electroluminescent compound according to the present disclosure exhibits suitable performance for use in organic electroluminescent devices. In addition, by including a plurality of types of host materials according to the present application, an organic electroluminescent device having a low driving voltage, high luminous efficiency, high power efficiency and/or excellent lifespan characteristics compared to a conventional organic electroluminescent device is provided, It is possible to manufacture a display device or a lighting device using the same.

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 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 transporting material, an electron injecting material, or the like.

As used herein, the term "plural kinds of organic electroluminescent materials" means an organic electroluminescent material in which two or more types of compounds that can be included in any layer constituting an organic electroluminescent device are combined, before being included in the organic electroluminescent device ( For example, it may refer to both a material before deposition) and after being 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 types of compounds may be included in the same layer or different layers, mixed vapor deposition or co-deposition, or may be deposited separately.

As used herein, "a plurality of types of host materials" means an organic electroluminescent material in which two or more types of host materials are combined, and before (eg, before deposition) and after being included in an organic electroluminescent device (eg, for example) , after deposition) may mean all of the materials. The plurality of types of host materials of the present application may be included in any light emitting layer constituting the organic electroluminescent device, and two or more kinds of compounds included in the plurality of types of host materials may be included in one light emitting layer, respectively, in different light emitting layers. may be included. When two or more types of host materials are included in one layer, for example, the layer may be mixed and vapor-deposited, or the layer may be separately and simultaneously co-deposited to form the layer.

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 and sec-butyl. As used herein, "(C2-C30) alkenyl" means a straight or branched chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20, more preferably 2 to It is 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 It is 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 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, 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, diphenylfluorenyl, benzoflu Orenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobi fluorenyl, 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, p- tert -butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 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-fluorene nyl, 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, 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] flu Orenyl, 11,11-dimethyl-10-benzo [c] fluorenyl, 11,11-diphenyl-1-benzo [a] fluorenyl, 11,11-diphenyl-2-benzo [a] flu Orenyl, 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] fluorenyl , 11,11-diphenyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,11-diphenyl-3-benzo [c] fluorene nyl, 11,11-diphenyl-4-benzo [c] fluorenyl, 11,11-diphenyl-5-benzo [c] fluorenyl, 11,11-diphenyl-6-benzo [c] flu Orenyl, 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)" is 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 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, 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, benzotriazolephenazine, imidazo and fused ring heteroaryls such as pyridine, chromenoquinazolinyl, thiochromenoquinazolinyl, 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-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- 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-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 Neil, 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]-benzothio Phenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzo Thiophenyl, 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] 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-sila Fluorenyl, 3-silafluorenyl, 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 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 interpreted as a single heteroaryl substituent or as a substituent in which two heteroaryl substituents are connected. substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted nitrogen containing heteroaryl, substituted cycloalkyl, substituted alkoxy, Substituents of substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted aliphatic and aromatic ring fused ring groups 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 of (C1-C30)alkyl and (C6-C30)aryl; substituted with one or more of deuterium, cyano, (C1-C30)alkyl, (C3-C30)cycloalkyl, tri(C1-C30)alkylsilyl, (C6-C30)aryl and (3-30 membered)heteroaryl; unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30); 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) arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C20)alkyl; (C6-C25)cycloalkyl; (5-25 membered)heteroaryl unsubstituted or substituted with one or more (C6-C25)aryl; substituted with one or more of deuterium, cyano, (C1-C20)alkyl, (C6-C25)cycloalkyl, tri(C1-C20)alkylsilyl, (C6-C25)aryl and (5-25 membered)heteroaryl; unsubstituted (C6-C25)aryl; mono- or di- (C6-C25)arylamino; mono- or di- (5-25 membered) heteroarylamino; and (C6-C25)aryl (5-25 membered)heteroarylamino. According to another aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C10)alkyl; (C6-C18)cycloalkyl; (5-20 membered)heteroaryl unsubstituted or substituted with one or more (C6-C18)aryl; substituted with one or more of deuterium, cyano, (C1-C10)alkyl, (C6-C18)cycloalkyl, tri(C1-C10)alkylsilyl, (C6-C15)aryl and (5-20 membered)heteroaryl; unsubstituted (C6-C25)aryl; di(C6-C18)arylamino; and (C6-C18)aryl (5-20 membered)heteroarylamino. Specifically, the substituents are each independently deuterium; cyano; methyl; cyclohexyl; substituted or unsubstituted phenyl; naphthyl; phenylnaphthyl; biphenyl; methylfluorenyl; dimethyl fluorenyl; diphenylfluorenyl; phenanthrenyl; anthracenyl; fluoranthenyl; terphenyl; chrysenyl; triphenylenyl; spirobifluorenyl; pyridyl substituted with phenyl; phenyl-substituted benzimidazolyl; triazinyl substituted with one or more selected from the group consisting of phenyl and naphthyl; benzothiophenyl; dibenzothiophenyl; dibenzofuranyl unsubstituted or substituted with phenyl and/or biphenyl; phenyl-substituted or unsubstituted carbazolyl; naphthooxazolyl substituted with phenyl; diphenylamino; dibiphenylamino; phenylbiphenylamino; phenyldibenzothiofuranylamino; and phenyldibenzothiophenylamino, and the like, and the substituent of the substituted phenyl may be one or more of deuterium, cyano, methyl, tert -butyl, naphthyl, trimethylsilyl, carbazolyl and cyclohexyl.

In the present formula, when connected to adjacent substituents to form a ring, the ring is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or these formed by connecting two or more adjacent substituents. It may be a ring of a combination of The ring formed may also contain one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. According to 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).

In the formula herein, heteroaryl, heteroarylene and heterocycloalkyl may each independently comprise 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 selected from the group consisting of amino may be bonded.

According to the present application, there is provided an organic electroluminescent device comprising an organic electroluminescent compound of Formula 2' or Formula 2". Here, the organic electroluminescent compound of Formula 2' or Formula 2" may be included in the emission layer or the electron transport layer. have.

The compound represented by Formula 2' will be described in more detail as follows.

[Formula 2']

In Formula 2',

Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl;

L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₁₁ is each independently any one of Formulas 3 to 5;

[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,

Y ₂ is O or S;

R ₂₀ to R ₂₉ are hydrogen or deuterium;

e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;

* indicates a position connected to L ₁₁ ;

However, when HAr is substituted triazinyl, the substituents of triazinyl are each independently deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, fluoranthenyl, cry senyl, carbazolyl, and combinations thereof, and when there are two substituents, they are the same as or different from each other.

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

The compound represented by Formula 2" will be described in more detail as follows.

[Formula 2"]

In Formula 2",

Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl , a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl;

L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₁₁ is each independently any one of Formulas 3 to 5;

[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,

Y ₂ is O or S;

R ₂₁ to R ₂₄ and R ₂₆ to R ₂₉ are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

R ₂₀ and R ₂₅ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;

* indicates a position connected to L ₁₁ .

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

A plurality of host materials according to an aspect herein include a first host material including a compound represented by Formula 1, and a second host material including a compound represented by Formula 2, and It may be included in the light emitting layer of the organic electroluminescent device according to the embodiment.

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

In Formula 1, X ₁ and Y ₁ are each independently -N=, -NR ₅ -, -O- or -S-, with the proviso that any one of X ₁ and Y ₁ is -N=, X ₁ and the other of Y ₁ is -NR ₅ -, -O- or -S-. According to an aspect of the present application, any one of X ₁ and Y ₁ is -N=, and the other is -O- or -S-. That is, X ₁ is -N= and Y ₁ is -O-, X ₁ is -N= and Y ₁ is -S-, X ₁ is -O- and Y ₁ is -N=, or X ₁ is -S - and Y ₁ may be -N=.

In Formula 1, R ₁ 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 ₁ 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 ₁ is a substituted or unsubstituted (C6-C30)aryl, or a substituted (5-20 membered)heteroaryl. For example, R ₁ is unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, methyl-substituted fluorenyl, methyl-substituted benzofluorenyl, unsubstituted dibenzofuranyl, unsubstituted cyclic dibenzothiophenyl, spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, unsubstituted pyridyl, and the like.

In Formula 1, L ₁ 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 ₁ is a single bond, or a substituted or unsubstituted (C6-C18)arylene. According to another aspect of the present application, L ₁ is a single bond, or an unsubstituted (C6-C12)arylene. For example, L ₁ may be a single bond, unsubstituted phenylene, unsubstituted naphthylene, or the like.

In Formula 1, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl. According to an aspect of the present application, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3-20 membered)heteroaryl. According to another aspect of the present application, Ar ₁ and Ar ₂ are each independently deuterium, (C1-C6)alkyl, (C6-C25)aryl, (3-20 membered)heteroaryl, (C3-C7)cycloalkyl and (C6-C25)aryl unsubstituted or substituted with one or more of (C1-C6)alkyl(C6-C12)aryl; or (3-20 membered)heteroaryl which is unsubstituted or substituted with one or more of (C6-C12)aryl and (5-15 membered)heteroaryl. For example, Ar ₁ and Ar ₂ are each independently a substituted phenyl, naphthyl, biphenyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorene nyl, terphenyl, spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl unsubstituted or substituted with phenyl, dibenzofuranyl unsubstituted or substituted with phenyl or pyridyl, substituted with phenyl carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzofuropyridyl, and the like; 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; phenoxazinyl; and phenyl-substituted benzimidazolyl.

In Formula 1, R ₂ to R ₅ 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 (C6-C30) aromatic ring, or -L ₃ -N(Ar ₃ )(Ar ₄ ); Adjacent substituents may be connected to each other to form a ring. According to an aspect of the present application, R ₂ to R ₅ are each independently hydrogen, or a substituted or unsubstituted (C6-C12)aryl. According to another aspect of the present application, R ₂ to R ₅ are each independently hydrogen or unsubstituted (C6-C12)aryl. For example, R ₂ and R ₃ may be hydrogen, and R ₄ may be hydrogen, phenyl, or the like.

In Formula 1, a is 1; b and c are each independently 1 or 2, preferably 1; d is an integer of 1 to 4, preferably 1 or 2. When b to d are an integer of 2 or more, each of R ₂ to R ₄ may be the same as or different from each other.

According to an aspect of the present application, Chemical Formula 1 may be represented by one or more 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, R ₁ to R ₄ , Ar ₁ , Ar ₂ , L ₁ , and a to d are the same as defined in Formula 1.

The compound represented by Formula 2 will be described in more detail as follows.

In Formula 2, HAr is each independently a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl. According to one aspect of the present application, each HAr is independently a substituted or unsubstituted nitrogen-containing (5-15 membered) heteroaryl. According to another aspect of the present application, HAr are each independently deuterium; (C1-C6)alkyl; (C6-C20)aryl unsubstituted or substituted with one or more of deuterium, (C1-C6)alkyl and (C6-C12)aryl; (5-15 membered) heteroaryl unsubstituted or substituted with (C6-C12)aryl; It is a nitrogen-containing (5-15 membered) heteroaryl unsubstituted or substituted with one or more of (C1-C6)alkyl(C6-C20)aryl. For example, each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquina Jolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or Unsubstituted benzoisoquinolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted triazanaphthyl , substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl, and the like, wherein the substituents are deuterium, methyl, phenyl, phenyl substituted with one or more deuterium, naphthylphenyl, naph Tyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, phenanthrenyl, fluoranthenyl, terphenyl, chrysenyl, triphenylenyl, phenylpyridyl, dibenzofuranyl, dibenzothio It may be at least one of phenyl and phenylcarbazolyl.

In Formula 2, L ₁₁ 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 ₁₁ 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 embodiment of the present application, each L ₁₁ is independently a single bond, (C6-C12) aryl-substituted or unsubstituted (C6-C15) arylene, or unsubstituted (5-15 membered) heteroarylene to be. For example, each L ₁₁ may independently be a single bond, phenylene, naphthylene, biphenylene, phenyl substituted phenylene, dibenzofuranylene, or the like.

In Formula 2, Ar ₁₁ is each independently any one of Formulas 3 to 5 below.

[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5, Y ₂ is O or S.

In Formulas 3 to 5, R ₂₀ to R ₂₉ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkyl Silyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6 -C30) arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L ₃ -N(Ar ₃ )(Ar ₄ ). According to an aspect of the present application, R ₂₀ to R ₂₉ are each independently hydrogen, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5-15 membered)heteroaryl. According to another aspect of the present application, R ₂₀ To R _{29 They} are each independently hydrogen; (C6-C20)aryl unsubstituted or substituted with one or more of deuterium, cyano, (C6-C12)aryl and (5-15 membered)heteroaryl; or (5-15 membered)heteroaryl unsubstituted or substituted with (C6-C12)aryl. For example, R ₂₀ to R ₂₉ are each independently hydrogen, phenyl, phenyl substituted with one or more deuterium, phenyl substituted with cyano, naphthylphenyl, phenyl substituted with dibenzothiophenyl, naphthyl, phenylnaphthyl , biphenyl, biphenyl substituted with one or more cyano, phenanthrenyl, pyridyl, pyridyl substituted with phenyl, isoquinolyl, carbazolyl substituted with phenyl, dibenzofuranyl, dibenzothiophenyl, etc. .

In Formula 2, e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other.

In Formulas 3 to 5, * represents a position connected to L ₁₁ .

In Formulas 1 and 3 to 5, L ₃ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene.

In Formulas 1 and 3 to 5, Ar ₃ and Ar ₄ are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted A fused ring group of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30), a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.

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 2 may be one or more selected from the following compounds, but is not limited thereto.

At least one of the compounds H1-1 to H1-136 and at least one of the compounds C-1 to C-127 may be combined to be used in an organic electroluminescent device.

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, Korean Patent Application Laid-Open No. 10-2017-0022865 (published on Mar. 02, 2017), Korean Patent Application Laid-Open No. 10 -2017-0051198 (published on May 11, 2017), may be manufactured with reference to Korean Patent Application Laid-Open No. 10-2018-0094572 (published on August 24, 2018), but is not limited thereto.

The compound represented by Formula 2 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 to 3, but is not limited thereto.

[Scheme 1]

[Scheme 2]

[Scheme 3]

In Schemes 1 to 3, Y ₂ , R ₂₀ to R ₂₉ , L ₁₁ , HAr and e are the same as defined in Formula 2, and Hal is a halogen atom.

Although exemplary synthesis examples of the compound represented by Formula 2 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 2 are combined in addition to the substituents specified in .

The organic electroluminescent device according to the present application includes an anode, a cathode, and at least one organic material layer between the anode and the cathode, wherein the organic material layer is a first organic electroluminescent material as a compound represented by Formula 1, and a second organic material layer The electroluminescent material may include a plurality of organic electroluminescent materials including the compound represented by Formula 2 above. According to an aspect of the present application, the organic electroluminescent device according to the present application includes an anode, a cathode, and at least one light emitting layer between the anode and the cathode, and the light emitting layer is a compound represented by Formula 1 and Formula 2 It may contain a compound that is

The light emitting layer includes a host and a dopant, the host includes a plurality of host materials, and the compound represented by Formula 1 is a first host compound among the plurality of host materials, and the compound represented by Formula 2 may be included as the second host compound among the plurality of types of host materials. Here, the weight ratio of the first host compound to the second host compound is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more preferably from about 30:70 to about 70:30 , more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

The light emitting layer herein may be a single layer as a layer that emits light, or may be a plurality of layers in which two or more layers are stacked. In the plurality of host materials of the present disclosure, both the first and second host materials may be included in one layer, and the first and second host materials may be included in different light emitting layers, respectively. According to one aspect of the present application, the doping concentration of the dopant compound with respect to the host compound of the emission layer may be less than 20% by weight.

The organic electroluminescent device of the present application 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 injection layer, an interlayer, an electron buffer layer, a hole blocking layer and an electron blocking layer. It may further include one or more floors. According to one aspect of the present application, the organic electroluminescent device of the present application includes an amine compound in addition to a plurality of host materials of the present application, among a hole injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emitting auxiliary material, and an electron blocking material. It may further include one or more. In addition, according to one aspect of the present application, the organic electroluminescent device of the present application may further include a 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 a plurality of host materials of the present application. can

A plurality of types of host materials according to the present disclosure 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, a plurality of host materials according to an example may be used in an organic electroluminescent device including quantum dots (QDs).

A hole injection layer, a hole transport layer, 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 electron blocking layer, and two compounds may be used in each layer at the same time. In addition, the hole injection layer may be doped with a p-dopant. 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, thereby preventing light emission leakage. A plurality of layers may be used for the hole transport layer or the electron blocking layer, and a plurality of compounds may be used for each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, 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. In addition, the electron injection layer may be doped with an n-dopant.

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 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, 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; 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.

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, nozzle printing, slot coating, It may be formed by any one of a wet film forming method such as spin coating, dip coating, flow coating, or the like.

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, the first and second host compounds of the present application can be formed by the methods listed above, and can often be formed by a co-deposition or mixed vapor deposition process. The co-deposition is a method of mixing two or more materials by putting two or more materials into each individual crucible source, evaporating the materials by applying an electric current to both cells at the same time, and performing mixed deposition. After mixing, a current is applied to one cell to evaporate the material, and mixed deposition is performed. In addition, when the first and second host compounds are present in the same layer or in different layers in the organic electroluminescent device, the two host compounds may be individually formed. For example, after depositing the first host compound, the second host compound may be deposited.

The present application uses the organic electroluminescent compound represented by Formula 2' or Formula 2", or a display device using a plurality of host materials including the compound represented by Formula 1 and the compound represented by Formula 2 That is, it is possible to manufacture a display device or a lighting device using the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present application, or using a plurality of host materials. Specifically, a display device, for example, a white organic light emitting device (White Organic Light Emitting Device), a display device for a smartphone, tablet, notebook, PC, TV or vehicle, or a lighting device, for example, for outdoor or indoor use It is possible to manufacture a lighting device.

Hereinafter, for a detailed understanding of the present application, for a detailed understanding of the present application, a method for preparing a compound according to the present application, a method for preparing a compound according to the present application, physical properties thereof, and characteristics of an OLED including a plurality of host materials of the present application will be described. However, the following Examples only describe the properties of an OLED including a compound according to the present application and a plurality of host materials according to the present application for a detailed understanding of the present application, and the present application is not limited to the following examples.

[Synthesis Example 1] Preparation of compound H1-27

1) Synthesis of compound 1

In a flask, dibenzofuran-2-amine (20 g, 144.7 mmol), 2-bromo dibenzofuran (23.8 g, 96.47 mmol), Pd(OAc) ₂ (1.1 g, 4.82 mmol), 2-dicyclohexyl Phosphino-2',6'-dimethoxybiphenyl (S-Phos) (3.9 g, 9.65 mmol), NaOt-Bu (13.9 g, 144.7 mmol) and 485 mL of o-xylene were added, and 3 hours at 160 °C. stirred for a while. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 1 (4.9 g, yield: 10%).

2) Synthesis of compound H1-27

In a flask, put compound 1 (4.9 g, 12.76 mmol), compound 2 (4.2 g, 14.0 mmol), Pd(dba ₃ ) ₂ (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol) and 65 mL of o-xylene were added and stirred at 160° C. for 2 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-27 (5.6 g, yield: 68.3%). .

[Synthesis Example 2] Preparation of compound H1-46

In a flask, compound 3 (25 g, 74.48 mmol), compound 2 (42.58 g, 81.93 mmol), Pd(OAc) ₂ (0.16 g, 7.5 mmol), P(t-Bu) ₃ (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol) and 284.09 mL of o-xylene were added, and the mixture was stirred at 160° C. for 2 hours. After completion of the reaction, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-46 (23.4 g, yield: 50%). .

[Synthesis Example 3] Preparation of compound H1-43

In a flask, compound 4 (20 g, 56.96 mmol), compound 2 (18.8 g, 57.13 mmol), Pd(OAc) ₂ (0.13 g, 5.7 mmol), P(t-Bu) ₃ (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol) and 227.27 mL of o-xylene were added, and the mixture was stirred at 160° C. for 2 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-43 (12.5 g, yield: 34%). .

[Synthesis Example 4] Preparation of compound H1-123

1) Synthesis of compound 5

In a flask, 3-aminobiphenyl (54 g, 319 mmol), 3-bromobiphenyl (70 g, 301 mmol), Pd(OAc) ₂ (0.33 g, 1.47 mmol), tricyclohexylphosphine (0.84 g, 2.8 mmol), NaOt-Bu (57 g, 593 mmol) and 280 mL of toluene were added and stirred at 95° C. for 8 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 5 (60.23 g, yield: 85%).

2) Synthesis of compound H1-123

In a flask, compound 5 (60.23 g, 187.5 mmol), compound 2 (60 g, 182.33 mmol), Pd(OAc) ₂ (0.41 g, 1.83 mmol), S-phos (1.74 g, 4.23 mmol), NaOt-Bu ( 26.23 g, 272 mmol) and 300 mL of xylene were added and stirred at 110° C. for 10 hours. After completion of the reaction, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-123 (36.9 g, yield: 33%). .

[Synthesis Example 5] Preparation of compound H1-136

1) Synthesis of compound 6

Dibenzofuran-2-amine (29.24 g, 159.7 mmol), 2-bromodibenzothiophene (40 g, 152.7 mmol), Pd(OAc) ₂ (0.17 g, 0.75 mmol), tricyclohexylphosphine in a flask (0.43 g, 1.45 mmol), NaOt-Bu (29.22 g, 304 mmol) and 250 mL of toluene were added and stirred at 95°C for 8 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 6 (17.12 g, yield: 86%).

2) Synthesis of compound H1-136

In a flask, compound 6 (17.12 g, 46.89 mmol), compound 2 (15 g, 45.58 mmol), Pd(OAc) ₂ (0.05 g, 0.22 mmol), S-phos (0.22 g, 0.535 mmol), NaOt-Bu ( 6.56 g, 68.2 mmol) and 75 mL of xylene were added and stirred at 110° C. for 10 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-136 (10.2 g, yield: 34%). .

[Synthesis Example 6] Preparation of compound H1-85

In a flask, compound 2 (5.0 g, 15.2 mmol), di([1,1'-biphenyl]-4-yl)amine (4.9 g, 15.2 mmol), Pd(OAc) ₂ (0.2 g, 0.8 mmol), P(t-Bu) ₃ (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol) and 76 mL of xylene were added, and the mixture was stirred at 160° C. for 5 hours. After the reaction was completed, it was cooled to room temperature, and the precipitated solid was washed with distilled water and methanol. After separation by column chromatography, compound H1-85 (5.5 g, yield: 59%) was obtained.

[Synthesis Example 7] Preparation of compound H1-51

In a flask, compound 2 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane- 2-yl)phenyl]amine (6.8 g, 13 mmol), Pd(OAc) ₂ (0.3 g, 1 mmol), S-Phos (0.9 g, 2 mmol), Cs ₂ CO ₃ (11.5 g, 35 mmol) , o-xylene 60mL, EtOH 15mL and distilled water 15mL were put, and the mixture was stirred under reflux at 150℃ for 3 hours. After completion of the reaction, the reaction was cooled to room temperature, washed with distilled water, the organic layer was extracted with ethyl acetate, the residual moisture was removed with magnesium sulfate, dried, and separated by column chromatography for compound H1-51 (2.2 g, yield: 27 %) was obtained.

[Synthesis Example 8] Preparation of compound H1-68

In a flask was placed compound 7 (4.8 g, 11.34 mmol), N-(4-bromophenyl)-N-phenyl-[1,1′-biphenyl]-4-amine (5 g, 12.47 mmol), Pd(PPh) ₃ ) ₄ (0.4 g, 0.34 mmol), Na ₂ CO ₃ (3.0 g, 28.35 mmol), toluene 57 mL, ethanol 14 mL and distilled water 14 mL were added, and the mixture was stirred at 120° C. for 4 hours. After the reaction was completed, the mixture was added dropwise to methanol and the resulting solid was filtered off. The resulting solid was purified by column chromatography to obtain compound H1-68 (1.4 g, yield: 20.0%).

[Synthesis Example 9] Preparation of compound H1-15

1) Synthesis of compound 8

In a flask, put compound 2 (10.0 g, 30.3 mmol), [1,1'-biphenyl]-3-amine (6.7 g, 39.4 mmol), Pd(OAc) ₂ (0.34 g, 1.5 mmol), P(t- Bu) ₃ (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol) and 150 mL of xylene were added, and the mixture was stirred at 160° C. for 6 hours. After the reaction was completed, the reaction was washed with distilled water, the organic layer was extracted with ethyl acetate, dried over magnesium sulfate, the solvent was removed by a rotary evaporator, and the mixture was separated by column chromatography to obtain compound 8 (10.8 g, yield: 36%).

2) Synthesis of compound H1-15

Compound 8 (5.0 g, 10.8 mmol), 3-bromo dibenzofuran (3.2 g, 12.9 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol) in a flask ), NaOt-Bu (2.0 g, 21.6 mmol) and o-xylene (60 mL) were added, and the mixture was stirred at 160°C for 6 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-15 (1.45 g, yield: 21%). .

[Synthesis Example 10] Preparation of compound C-2

11-Chlorobenzo [b] naphtho [2,3-d] thiophene (3.6 g, 13.4 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (6.4 g, 14.77 mmol), Pd ₂ (dba) ₃ (613 mg, 0.67 mmol), 2- 70 mL of o-xylene was added to dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (550 mg, 1.34 mmol) and K ₃ PO ₄ (7.1 g, 33.5 mmol) After that, the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through silica gel. The organic layer was distilled under reduced pressure and recrystallized from o-xylene to obtain compound C-2 (3.0 g, yield: 41.3%).

[Synthesis Example 11] Preparation of compound C-57

11-Chlorobenzo [b] naphtho [2,3-d] furan (1.4 g, 5.5 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1) ,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (2.7 g, 6.1 mmol), Pd ₂ (dba) ₃ (252 mg, 0.275 mmol), S-Phos (225 mg, 0.55 mmol) and K ₃ PO ₄ (2.9 g, 13.75 mmol) was added with 30 mL of o-xylene, followed by stirring under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through silica gel. The organic layer was distilled under reduced pressure and recrystallized from o-xylene to obtain compound C-57 (0.9 g, yield: 30%).

[Device Examples 1 and 2] Preparation of a red light-emitting OLED in which a compound according to the present invention is deposited as a host

An OLED according to the present invention was 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 in the substrate holder of the vacuum deposition equipment, put the compound HI-1 of Table 3 into a cell in the vacuum deposition equipment, and put the compound HT-1 of Table 3 into another cell, and then the two materials 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 by evaporation at different rates. 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-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 compound of Table 1 as a host in a cell in the vacuum deposition equipment, and putting 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 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 3 wt%. Subsequently, compound ETL-1 and compound EIL-1 were evaporated at a rate of 1:1 in each of two other cells to deposit an electron transport layer with a thickness of 35 nm on the emission layer. 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. .

[Comparative Example 1] Preparation of a red light-emitting OLED in which a conventional compound is deposited as a host

OLEDs were manufactured in the same manner as in Device Examples 1 and 2, except that Compound A of Table 3 was used as a host of the emission layer.

The driving voltage, luminous efficiency, power efficiency and luminous color of the organic electroluminescent devices of Examples 1 and 2 and Comparative Example 1 prepared as described above based on 1,000 nit luminance are shown in Table 1 below.

[Table 1]

From Table 1 above, the organic electroluminescent device including the organic electroluminescent compound according to the present application as a host exhibited luminous efficiency equivalent to that of the organic electroluminescent device of Comparative Example 1, and excellent driving voltage and power efficiency characteristics compared to Comparative Example 1. You can verify that it is provided. An organic electroluminescent device including a host material according to the present disclosure may have advantages in terms of lifetime characteristics.

In the organic electroluminescent compound represented by Formula 2' and the organic electroluminescent compound represented by Formula 2" according to the present application, the LUMO energy level, HOMO energy level, and triplet energy of the parent nucleus were respectively measured and shown in Table 1-1 below. it was

[Table 1-1]

* The structure was optimized by applying the background sets of B3LYP and 6-31G(d), which are hybrid DFT: Density Functional Theory, with Gaussian 16, Gaussian's quantum chemistry calculation program, and TD-DFT (time dependent DFT) ) was used to calculate the triplet state.

Referring to Table 1-1, the parent nucleus of the organic electroluminescent compound (introducing a substituent to R ₂₀ or R ₂₅ ) represented by Formula 2" according to the present invention is represented by Formula 2' used in Device Examples 1 and 2 It can be seen that the displayed organic electroluminescent compounds C-2 and C-57 have similar energy levels to the parent nuclei. Through this, even when the organic electroluminescent compound of Formula 2" is used as a host material, the device Examples 1 and 2 It can be expected to have similar device characteristics to

[Device Examples 3 to 5] Preparation of a red light emitting OLED in which a plurality of types of host materials according to the present invention are deposited as a host

In depositing the light emitting layer, each of the first host compound and the second host compound described in Table 2 below as hosts were put in two cells, and after putting compound D-39 in another cell, the two host materials were mixed in a 1:1 ratio. An OLED was manufactured in the same manner as in Device Examples 1 and 2, except that deposition was carried out by evaporating at a rate and simultaneously evaporating the dopant material at different rates, thereby doping the dopant in an amount of 3 wt% with respect to the total amount of the host and dopant. did

Table 2 below shows the driving voltage, luminous efficiency, and emission color based on 1,000 nit luminance of the organic electroluminescent devices of Device Examples 3 to 5 prepared as described above.

[Table 2]

Previously, when the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present application was used as a single host in Device Examples 1 and 2, it was confirmed that an OLED having excellent luminous efficiency, driving voltage and power efficiency characteristics was provided. In addition, from Table 2 above, the organic electroluminescent device including a plurality of types of host materials according to the present application as a host is higher than when the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present application is used as a single host. It can be confirmed that more excellent driving voltage, luminous efficiency and/or power efficiency characteristics are provided. The organic electroluminescent device including a plurality of types of host materials according to the present disclosure may have advantages in lifespan characteristics.

Although not limited by theory, the light emitting layer is made into an electron-dominant system by using the compound of Formula 2 as the second host, and the compound of Formula 1, which is an amine compound, is used as the first host to provide a large number of holes to exciton to be provided in abundance. In addition, without being limited by theory, it was possible to lower the HOMO barrier between the hole transport layer/emission layer due to the high HOMO energy level of the first host. As a result, characteristics of low driving voltage, high power efficiency, and long life can be obtained.

The compounds used in Device Examples 1 to 5 and Comparative Example 1 are shown in Table 3 below.

[Table 3]

[Device Example 6] Preparation of blue light emitting OLED in which the compound according to the present invention is deposited as an electron transport layer

OLEDs according to the invention were prepared. 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 isopropyl alcohol and stored for use. Next, after mounting the ITO substrate on the substrate holder of the vacuum deposition equipment, the compound HI-1 described in Table 5 as the first hole injection compound was put into the cell in the vacuum deposition equipment, and the compound HT- After adding 1 , the two substances were evaporated at different rates to give compound HI-1 and A hole injection layer was deposited by doping the compound HI-1 to a thickness of 10 nm in an amount of 3 wt% with respect to the total amount of the 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-3 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 5 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 BH host compound shown in Table 5 below as a host in two cells in the vacuum deposition equipment, and putting compound BD as a dopant in another cell, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously A light emitting layer with a thickness of 20 nm was deposited on the hole transport layer by evaporating at different rates and doping the dopant in an amount of 3 wt% with respect to the total amount of the host and the dopant. Subsequently, compound BF was deposited to a thickness of 5 nm as an electron buffer layer on the light emitting layer. Then, as an electron transport layer on the light emitting layer Compound C-2 and compound EIL-1 of Table 5 were deposited to a thickness of 30 nm in a 50:50 weight ratio. 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.

[Comparative Example 2] Manufacture of blue light emitting OLED in which a conventional compound is deposited as an electron transport layer

An OLED was manufactured in the same manner as in Device Example 6 except that Compound A was used instead of Compound C-2 shown in Table 5 as an electron transport layer.

The driving voltage, luminous efficiency, luminous color and external quantum efficiency based on 1,000 nit luminance of the organic electroluminescent device of Example 6 and Comparative Example 2 prepared as described above are shown in Table 4 below.

[Table 4]

From Table 4, the organic electroluminescent device including the compound according to the present application as an electron transport layer has superior driving voltage, luminous efficiency and/or external compared to the organic electroluminescent device of Comparative Example 2 including the conventional compound as an electron transport layer. It can be confirmed that quantum efficiency characteristics are provided.

The compounds used in Device Example 6 and Comparative Example 2 are shown in Table 5 below.

[Table 5]

Claims (14)

An organic electroluminescent compound represented by the following formula 2':
[Formula 2']

In Formula 2',
Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl;
L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁₁ is each independently any one of Formulas 3 to 5;
[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,
Y ₂ is O or S;
R ₂₀ to R ₂₉ are hydrogen or deuterium;
e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;
* indicates a position connected to L ₁₁ ;
However, when HAr is substituted triazinyl, the substituents of triazinyl are each independently deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, fluoranthenyl, cry senyl, carbazolyl, and combinations thereof, and when there are two substituents, they are the same as or different from each other. An organic electroluminescent compound represented by the following formula (2):
[Formula 2"]

In Formula 2",
Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl , a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl;
L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁₁ is each independently any one of Formulas 3 to 5;
[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,
Y ₂ is O or S;
R ₂₁ to R ₂₄ and R ₂₆ to R ₂₉ are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R ₂₀ and R ₂₅ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;
* indicates a position connected to L ₁₁ . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 2 . The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 2' is selected from the following compounds.

The organic electroluminescent compound according to claim 2, wherein the compound represented by Formula 2" is selected from the following compounds.

A plurality of host materials including at least one first host compound and at least one second host compound, wherein the first host compound is represented by Formula 1 below, and the second host compound is represented by Formula 2 below wherein a plurality of species of host material:
[Formula 1]

In Formula 1,
X ₁ and Y ₁ are each independently -N=, -NR ₅ -, -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 ₅ -, -O- or -S-;
R ₁ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
L ₁ is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R ₂ to 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, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₃ -N(Ar ₃ )(Ar ₄ ); adjacent substituents may be linked to each other to form a ring;
a is 1, b and c are each independently 1 or 2, d is an integer of 1 to 4, and when b to d are an integer of 2 or more, each R ₂ to R ₄ may be the same or different from each other, ;
[Formula 2]

In Formula 2,
each HAr is independently a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl;
L ₁₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁₁ is each independently any one of Formulas 3 to 5;
[Formula 3] [Formula 4] [Formula 5]

In Formulas 3 to 5,
Y ₂ is O or S;
R ₂₀ to R ₂₉ 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 an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L ₃ -N(Ar ₃ )(Ar ₄ );
e is 1 or 2, and when e is 2, each (L ₁₁ -HAr) may be the same as or different from each other;
* indicates a position connected to L ₁₁ ;
In Formulas 1 and 3 to 5,
L ₃ is each independently 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; (C6-C30) is a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl. 8. The substituted heteroaryl of claim 7, wherein said substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted nitrogen containing heteroaryl, substituted cycloalkyl, substituted Substituents of alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted aliphatic and aromatic ring fused ring groups 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 of (C1-C30)alkyl and (C6-C30)aryl; substituted with one or more of deuterium, cyano, (C1-C30)alkyl, (C3-C30)cycloalkyl, tri(C1-C30)alkylsilyl, (C6-C30)aryl and (3-30 membered)heteroaryl; unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30); 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) arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; And (C1-C30) alkyl (C6-C30) at least one selected from the group consisting of aryl, a plurality of types of host material. The method according to claim 7, wherein Chemical Formula 1 is represented by one or more of the following Chemical Formulas 1-1 to 1-4, a plurality of host materials:
[Formula 1-1] [Formula 1-2]

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

In Formulas 1-1 to 1-4,
R ₁ to R ₄ , Ar ₁ , Ar ₂ , L ₁ and a to d are as defined in claim 7. The method according to claim 7, wherein R ₁ , Ar ₁ and Ar ₂ of Formula 1 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 pyridyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxali nyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyridyl, 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 An unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl, a plurality of types of host materials. According to claim 7, wherein HAr of Formula 2 is each independently a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted Isoquinolyl, substituted or unsubstituted benzoisoquinolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted A plurality of types of host material, which is a substituted triazanaphthyl, a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl. The plurality of host materials according to claim 7, wherein the compound represented by Formula 1 is at least one selected from the following compounds.

The plurality of host materials according to claim 7, wherein the compound represented by Formula 2 is at least one selected from the following compounds.

An organic electroluminescent device comprising an anode, a cathode, and at least one light emitting layer between the anode and the cathode, wherein at least one of the light emitting layers comprises a plurality of kinds of the host material according to claim 7.

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